Bluesprucerealty.com Search Results

$549,000

A private garden setting just minutes from the heart of Middlebury, this thoughtfully cared-for home offers an appealing combination of beauty, ease and understated elegance. Surrounded by mature hedgerows and spectacular gardens, the property feels wonderfully secluded while keeping the shops, restaurants and cultural life of Middlebury close at hand. Clean lines and a fresh, uncluttered aesthetic create an inviting backdrop for everyday living. The main level is especially well designed for convenience, with all bedrooms, bathrooms and laundry together on one floor including a "bonus" room adjacent to the dining room-perfect for gear/mudroom, an office or a walk-in pantry! The primary suite offers a generous walk-in closet and its own slate patio overlooking open fields and Chipman Hill, a lovely spot for morning coffee, an afternoon in the sun or watching the landscape change at sunset. The outdoor spaces are equally inviting. An expansive deck provides plenty of room for dining and gathering with friends, while the beautifully tended gardens offer a succession of color and texture throughout the seasons. There is something particularly satisfying about a home where even the practical pleasures, grilling dinner, enjoying a summer evening outdoors or hanging freshly washed sheets in the breeze feel a little more special. A full basement provides abundant storage, complemented by two storage sheds. The home is generator-ready and equipped with both an oil-fired boiler and two heat pumps/mini-splits as well as a wood burning insert in the dining room fireplace, offering flexibility for year-round comfort. Beautifully situated, exceptionally well maintained and close to everything that makes Middlebury such a desirable place to live, this is a home that quietly rewards you every day.

3 Beds ⋅ 2 Baths ⋅ 5108596 MLS

A private garden setting just minutes from the heart of Middlebury, this thoughtfully cared-for home offers an appealing combination of beauty, ease and understated elegance. Surrounded by mature hedgerows and spectacular gardens, the property feels wonderfully secluded while keeping the shops, restaurants and cultural life of Middlebury close at hand. Clean lines and a fresh, uncluttered aesthetic create an inviting backdrop for everyday living. The main level is especially well designed for convenience, with all bedrooms, bathrooms and laundry together on one floor including a "bonus" room adjacent to the dining room-perfect for gear/mudroom, an office or a walk-in pantry! The primary suite offers a generous walk-in closet and its own slate patio overlooking open fields and Chipman Hill, a lovely spot for morning coffee, an afternoon in the sun or watching the landscape change at sunset. The outdoor spaces are equally inviting. An expansive deck provides plenty of room for dining and gathering with friends, while the beautifully tended gardens offer a succession of color and texture throughout the seasons. There is something particularly satisfying about a home where even the practical pleasures, grilling dinner, enjoying a summer evening outdoors or hanging freshly washed sheets in the breeze feel a little more special. A full basement provides abundant storage, complemented by two storage sheds. The home is generator-ready and equipped with both an oil-fired boiler and two heat pumps/mini-splits as well as a wood burning insert in the dining room fireplace, offering flexibility for year-round comfort. Beautifully situated, exceptionally well maintained and close to everything that makes Middlebury such a desirable place to live, this is a home that quietly rewards you every day.

922 Happy Valley Rd, Middlebury

$499,000

Qualified pricing - check with your agent to see if you qualify! Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

3 Beds ⋅ 3 Baths ⋅ 5108296 MLS

Qualified pricing - check with your agent to see if you qualify! Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

32 Barnes Brook Rd Unit 10.3, Middlebury

$495,000

Located in the heart of Middlebury, this home has been thoughtfully updated and improved upon by the current owners, turn-key ready for its next owner. This is a ranch style home, perfect for single-floor living. With new Quartz kitchen countertops, new appliances, new kitchen sink, and new flooring, the kitchen that once was divided by a wall now generously opens up to the living room, where a wood burning fireplace invites cozy nights. New insulation in the living room wall keeps the house warm, while a new mini-split allows cooler summers. A sweet sunroom has been finished to be year-round space with new energy efficient windows, insulation, walls and floors, and will be your favorite spot to hang out. The sunroom overlooks the spacious backyard, privately enclosed by evergreens. Down the hall are three bedrooms, all complete with new flooring. New lighting fixtures and new ceilings to eliminate popcorn were installed throughout the first floor. A full bath has two sinks, a bathtub, and stone tile detailing. Laundry is conveniently on the same floor. The finished lower level is perfect for games, office space, or additional family room. A 1/2 bath on this floor is handy, and a laundry hook-up is available. Located in the sought after Buttolph acres neighborhood, the half an acre lot allows plenty of space for gardening, pets, and outdoor enjoyment. You can easily walk to grocery stores, recreational facilities, multiple TAM trails, shops and all that Middlebury has to offer!

3 Beds ⋅ 2 Baths ⋅ 5108261 MLS

Located in the heart of Middlebury, this home has been thoughtfully updated and improved upon by the current owners, turn-key ready for its next owner. This is a ranch style home, perfect for single-floor living. With new Quartz kitchen countertops, new appliances, new kitchen sink, and new flooring, the kitchen that once was divided by a wall now generously opens up to the living room, where a wood burning fireplace invites cozy nights. New insulation in the living room wall keeps the house warm, while a new mini-split allows cooler summers. A sweet sunroom has been finished to be year-round space with new energy efficient windows, insulation, walls and floors, and will be your favorite spot to hang out. The sunroom overlooks the spacious backyard, privately enclosed by evergreens. Down the hall are three bedrooms, all complete with new flooring. New lighting fixtures and new ceilings to eliminate popcorn were installed throughout the first floor. A full bath has two sinks, a bathtub, and stone tile detailing. Laundry is conveniently on the same floor. The finished lower level is perfect for games, office space, or additional family room. A 1/2 bath on this floor is handy, and a laundry hook-up is available. Located in the sought after Buttolph acres neighborhood, the half an acre lot allows plenty of space for gardening, pets, and outdoor enjoyment. You can easily walk to grocery stores, recreational facilities, multiple TAM trails, shops and all that Middlebury has to offer!

5 Swanage Ct, Middlebury

$429,000

Exceptionally maintained and tastefully updated, this charming home is tucked away in the highly desirable Forest Ridge neighborhood of East Middlebury, where properties rarely come to market. Set on a private, beautifully landscaped lot with nearby access to the Green Mountain National Forest, Lake Dunmore, and Middlebury Snowbowl, this location offers endless opportunities for hiking, recreation, and outdoor adventure while remaining less than 10 minutes from downtown Middlebury’s restaurants, shops, and amenities. The shaded lot is thoughtfully landscaped with raised beds, perennial gardens, and a convenient storage shed for tools and equipment. A welcoming covered front porch with a built-in swing leads into a functional mudroom featuring vaulted ceilings. Inside, the spacious living room is filled with natural light from abundant windows and offers a cozy wood stove for chilly Vermont evenings, along with a convenient office nook. French doors open to the well-appointed chef’s kitchen with stainless steel appliances, ample cabinetry, and an inviting eat-in dining area. A fully screened porch extends the living space and provides the perfect spot to relax and enjoy the peaceful surroundings. A beautiful hardwood staircase leads to the upper level, where two spacious bedrooms and a full bath create a comfortable private retreat. The lower level offers additional flexibility with a finished den, guest space, or home office, while the unfinished portion is thoughtfully arranged as a workshop for the home hobbyist. Meanwhile a walkout entry boasts direct access to the concrete patio and backyard. With its exceptional maintenance, thoughtful updates, inviting outdoor spaces, peaceful setting, and spectacular East Middlebury location, this is a rare opportunity to enjoy the best of Vermont living just minutes from town. A true gem that won’t last long! *Showings begin 9/8/26*

2 Beds ⋅ 2 Baths ⋅ 5108105 MLS

Exceptionally maintained and tastefully updated, this charming home is tucked away in the highly desirable Forest Ridge neighborhood of East Middlebury, where properties rarely come to market. Set on a private, beautifully landscaped lot with nearby access to the Green Mountain National Forest, Lake Dunmore, and Middlebury Snowbowl, this location offers endless opportunities for hiking, recreation, and outdoor adventure while remaining less than 10 minutes from downtown Middlebury’s restaurants, shops, and amenities. The shaded lot is thoughtfully landscaped with raised beds, perennial gardens, and a convenient storage shed for tools and equipment. A welcoming covered front porch with a built-in swing leads into a functional mudroom featuring vaulted ceilings. Inside, the spacious living room is filled with natural light from abundant windows and offers a cozy wood stove for chilly Vermont evenings, along with a convenient office nook. French doors open to the well-appointed chef’s kitchen with stainless steel appliances, ample cabinetry, and an inviting eat-in dining area. A fully screened porch extends the living space and provides the perfect spot to relax and enjoy the peaceful surroundings. A beautiful hardwood staircase leads to the upper level, where two spacious bedrooms and a full bath create a comfortable private retreat. The lower level offers additional flexibility with a finished den, guest space, or home office, while the unfinished portion is thoughtfully arranged as a workshop for the home hobbyist. Meanwhile a walkout entry boasts direct access to the concrete patio and backyard. With its exceptional maintenance, thoughtful updates, inviting outdoor spaces, peaceful setting, and spectacular East Middlebury location, this is a rare opportunity to enjoy the best of Vermont living just minutes from town. A true gem that won’t last long! *Showings begin 9/8/26*

17 Forest Ridge Rd, Middlebury

$1,250,000

A remarkable Middlebury home where thoughtful craftsmanship, refined finishes, and effortless livability come together beautifully. Meticulously renovated in 2016/17, this distinctive home has been transformed into an elegant retreat designed equally well for gracious entertaining and comfortable everyday living. The main level offers beautifully proportioned spaces, including a spectacular dining room with custom built-in shelving, a generous living room with gas fireplace, and a sophisticated eat-in kitchen centered around a large island with seating. Quality details include a six-burner gas range, pot filler, two mudroom entrances, home work space and an inviting breakfast nook. Upstairs, the serene primary suite is a true delight, featuring a private porch with views toward the Green Mountains, an idyllic spot to welcome the sunrise. A walk-in closet and beautifully appointed custom-tile bath complete the suite, with dual vanities, a spacious walk-in shower, and luxurious soaking tub. Also on this level are a second bedroom, ¾ bath, and charming den with a cozy trundle bed, perfect for guests or an afternoon escape. The third floor reveals yet another generously sized bedroom with its own private bath, offering flexibility and privacy for family or guests. The two-car garage adds another dimension to the property. Beyond vehicle storage, the main level includes a finished area ideal for a home gym, while the upper level offers a private two-bedroom guest suite with its own bathroom and second kitchen, perfect for extended stays, visitors, or additional living space. Outside, a handsome stone wall , pergola and beautiful patio create an inviting covered outdoor living area, while the expansive, level lawn provides ample room for games, entertaining, or simply enjoying the privacy of the fenced grounds. All of this, just a stroll from Middlebury’s celebrated shops, restaurants, and college sport courts/fields. Timeless character meets exceptional craftsmanship.

5 Beds ⋅ 5 Baths ⋅ 5107309 MLS

A remarkable Middlebury home where thoughtful craftsmanship, refined finishes, and effortless livability come together beautifully. Meticulously renovated in 2016/17, this distinctive home has been transformed into an elegant retreat designed equally well for gracious entertaining and comfortable everyday living. The main level offers beautifully proportioned spaces, including a spectacular dining room with custom built-in shelving, a generous living room with gas fireplace, and a sophisticated eat-in kitchen centered around a large island with seating. Quality details include a six-burner gas range, pot filler, two mudroom entrances, home work space and an inviting breakfast nook. Upstairs, the serene primary suite is a true delight, featuring a private porch with views toward the Green Mountains, an idyllic spot to welcome the sunrise. A walk-in closet and beautifully appointed custom-tile bath complete the suite, with dual vanities, a spacious walk-in shower, and luxurious soaking tub. Also on this level are a second bedroom, ¾ bath, and charming den with a cozy trundle bed, perfect for guests or an afternoon escape. The third floor reveals yet another generously sized bedroom with its own private bath, offering flexibility and privacy for family or guests. The two-car garage adds another dimension to the property. Beyond vehicle storage, the main level includes a finished area ideal for a home gym, while the upper level offers a private two-bedroom guest suite with its own bathroom and second kitchen, perfect for extended stays, visitors, or additional living space. Outside, a handsome stone wall , pergola and beautiful patio create an inviting covered outdoor living area, while the expansive, level lawn provides ample room for games, entertaining, or simply enjoying the privacy of the fenced grounds. All of this, just a stroll from Middlebury’s celebrated shops, restaurants, and college sport courts/fields. Timeless character meets exceptional craftsmanship.

40 South St, Middlebury

$279,000

Welcome to 36 Seymour Street, Unit 1, a charming first floor 2-bedroom, 1-bath condo offering 1,024 square feet of comfortable living space in a convenient Middlebury location. Inside, you'll find a functional layout with a spacious kitchen and dining area, hardwood and tile flooring, and the added convenience of first-floor laundry. Two well-sized bedrooms provide flexibility for everyday living, or guests. An additional room could be fit up as a home office, a huge closet or some additional inside storage space. Outside, enjoy a covered porch with privacy fencing, patio, and garden space, while the unfinished basement provides additional room for storage. The low $160 monthly association fee includes landscaping, plowing, and trash removal, helping make day-to-day maintenance a little easier. The location is a standout, offering convenient access to everything Middlebury has to offer. Downtown is home to locally owned shops, restaurants, cafes, a movie theater, library, and other community amenities. Middlebury College adds arts, cultural events, and recreational opportunities to the area, while the Trail Around Middlebury provides miles of trails for walking, running, and biking. With shopping, dining, schools, recreation, and everyday necessities all nearby, this condo offers a great opportunity to enjoy the convenience and character of one of Addison County's most vibrant communities.

2 Beds ⋅ 1 Baths ⋅ 5106773 MLS

Welcome to 36 Seymour Street, Unit 1, a charming first floor 2-bedroom, 1-bath condo offering 1,024 square feet of comfortable living space in a convenient Middlebury location. Inside, you'll find a functional layout with a spacious kitchen and dining area, hardwood and tile flooring, and the added convenience of first-floor laundry. Two well-sized bedrooms provide flexibility for everyday living, or guests. An additional room could be fit up as a home office, a huge closet or some additional inside storage space. Outside, enjoy a covered porch with privacy fencing, patio, and garden space, while the unfinished basement provides additional room for storage. The low $160 monthly association fee includes landscaping, plowing, and trash removal, helping make day-to-day maintenance a little easier. The location is a standout, offering convenient access to everything Middlebury has to offer. Downtown is home to locally owned shops, restaurants, cafes, a movie theater, library, and other community amenities. Middlebury College adds arts, cultural events, and recreational opportunities to the area, while the Trail Around Middlebury provides miles of trails for walking, running, and biking. With shopping, dining, schools, recreation, and everyday necessities all nearby, this condo offers a great opportunity to enjoy the convenience and character of one of Addison County's most vibrant communities.

36 Seymour St Unit 1, Middlebury

$225,000

Exceptional redevelopment opportunity in East Middlebury for either commercial or residential uses. Bring your vision to life at 51 Ossie Road, a unique property with a long-standing history as the home of Otter East Bakery. For decades, this well-known location served as a successful food production facility, making it an excellent opportunity for entrepreneurs, investors, or business owners looking to establish or expand their operations. Situated on 0.29 acres in the heart of East Middlebury, the 2,088-square-foot building is connected to municipal water and serviced by an on-site septic system. The property also offers ample parking, a charming yard with mature apple trees, and would make a wonderful primary residence or residential rental property. Following a recent fire, the building has been fully gutted, creating a blank canvas for redevelopment into a home or rental property. Whether you’re looking to restore the existing structure, customize the space to meet your needs, or pursue a complete build-to-suit project, this property offers outstanding potential. Available as-is or as a build-to-suit opportunity, 51 Ossie Road is a rare chance to create a space tailored to your vision in a highly visible and established East Middlebury location. Property Highlights: Former home of the renowned Otter East Bakery Decades of established food production use 2,088 SF commercial building 0.29-acre lot Municipal water and on-site septic Ample on-site parking Attractive yard with mature apple trees

5104820 MLS

Exceptional redevelopment opportunity in East Middlebury for either commercial or residential uses. Bring your vision to life at 51 Ossie Road, a unique property with a long-standing history as the home of Otter East Bakery. For decades, this well-known location served as a successful food production facility, making it an excellent opportunity for entrepreneurs, investors, or business owners looking to establish or expand their operations. Situated on 0.29 acres in the heart of East Middlebury, the 2,088-square-foot building is connected to municipal water and serviced by an on-site septic system. The property also offers ample parking, a charming yard with mature apple trees, and would make a wonderful primary residence or residential rental property. Following a recent fire, the building has been fully gutted, creating a blank canvas for redevelopment into a home or rental property. Whether you’re looking to restore the existing structure, customize the space to meet your needs, or pursue a complete build-to-suit project, this property offers outstanding potential. Available as-is or as a build-to-suit opportunity, 51 Ossie Road is a rare chance to create a space tailored to your vision in a highly visible and established East Middlebury location. Property Highlights: Former home of the renowned Otter East Bakery Decades of established food production use 2,088 SF commercial building 0.29-acre lot Municipal water and on-site septic Ample on-site parking Attractive yard with mature apple trees

51 Ossie Rd, Middlebury

$539,000

This 4 bedroom, 2 bath cape is tucked into a nice, quiet Middlebury neighborhood. It's been lovingly cared for by the same family since the beginning, with many upgrades over the years including a huge primary suite over the garage. The upstairs bedrooms are all spacious and inviting, with an additional bedroom on the 1st floor. The briight living room is open to the dining room, with a glass door leading to the back deck, the perfetct place for morning coffee or bbq's. Enjoy the tranquility of this home, and also the convenience being only a few mins from town.

4 Beds ⋅ 2 Baths ⋅ 5104263 MLS

This 4 bedroom, 2 bath cape is tucked into a nice, quiet Middlebury neighborhood. It's been lovingly cared for by the same family since the beginning, with many upgrades over the years including a huge primary suite over the garage. The upstairs bedrooms are all spacious and inviting, with an additional bedroom on the 1st floor. The briight living room is open to the dining room, with a glass door leading to the back deck, the perfetct place for morning coffee or bbq's. Enjoy the tranquility of this home, and also the convenience being only a few mins from town.

160 Mead Ln, Middlebury

$410,000

Welcome to your next home,10 Case Street, a charming 3-bedroom, 2-bath home dating back to 1840. Filled with character and warmth, this home features beautiful wood floors and the timeless appeal of an older Vermont property. Outside, there is plenty of garden space to create your own outdoor retreat, whether you envision flower gardens, vegetables, entertaining areas, or simply a peaceful place to enjoy the seasons. Conveniently located in East Middlebury, this home is just a short distance from the post office, gas station, and the historic Waybury Inn, making everyday errands and local amenities easily accessible. Enjoy the close-knit feel of East Middlebury while being just minutes from everything Middlebury has to offer. A wonderful opportunity to own a historic Vermont home with character, usable outdoor space, and a convenient location!

3 Beds ⋅ 2 Baths ⋅ 5104160 MLS

Welcome to your next home,10 Case Street, a charming 3-bedroom, 2-bath home dating back to 1840. Filled with character and warmth, this home features beautiful wood floors and the timeless appeal of an older Vermont property. Outside, there is plenty of garden space to create your own outdoor retreat, whether you envision flower gardens, vegetables, entertaining areas, or simply a peaceful place to enjoy the seasons. Conveniently located in East Middlebury, this home is just a short distance from the post office, gas station, and the historic Waybury Inn, making everyday errands and local amenities easily accessible. Enjoy the close-knit feel of East Middlebury while being just minutes from everything Middlebury has to offer. A wonderful opportunity to own a historic Vermont home with character, usable outdoor space, and a convenient location!

10 Case St, Middlebury

$499,000

Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The wrap-around, covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

3 Beds ⋅ 3 Baths ⋅ 5104010 MLS

Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The wrap-around, covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

88 Brush Ln Unit 10.8, Middlebury

$187,000

OPPORTUNITY IS KNOCKING! With a little sweat equity, you can unlock the potential of this 2 bedroom, 2 bath condo being sold in an estate sale "As Is." The home features two generously sized bedrooms, a comfortable living room, and a kitchen with an island that overlooks the dining area and opens to the deck. A walk-in pantry, half bath down, and full bath up add convenience. The laundry room is located in the full basement which provides abundant storage and room for multiple uses. This property is an improvement project including flooring, painting, some trim work and heat (boiler not connected). The estate administrator has never occupied the property, so there is limited knowledge of the home. Located conveniently in a desirable college town, this condo is close to the local hospital, schools, shopping, dining, and other everyday conveniences. Although an improvement project, where do you find this price in Middlebury?? You can make this baby shine!!

2 Beds ⋅ 2 Baths ⋅ 5103821 MLS

OPPORTUNITY IS KNOCKING! With a little sweat equity, you can unlock the potential of this 2 bedroom, 2 bath condo being sold in an estate sale "As Is." The home features two generously sized bedrooms, a comfortable living room, and a kitchen with an island that overlooks the dining area and opens to the deck. A walk-in pantry, half bath down, and full bath up add convenience. The laundry room is located in the full basement which provides abundant storage and room for multiple uses. This property is an improvement project including flooring, painting, some trim work and heat (boiler not connected). The estate administrator has never occupied the property, so there is limited knowledge of the home. Located conveniently in a desirable college town, this condo is close to the local hospital, schools, shopping, dining, and other everyday conveniences. Although an improvement project, where do you find this price in Middlebury?? You can make this baby shine!!

3 Woodbridge Ln Unit 3, Middlebury

$495,000

Set on 10 private acres, this charming log home offers the perfect balance of privacy, open lawn, and wooded surroundings, creating a peaceful Vermont retreat just 10 minutes from downtown Middlebury. Inside, the warm wood interior, high ceilings, and skylights fill the home with an abundance of natural light, creating a bright and inviting atmosphere throughout. The open-concept living room, dining area, and kitchen flow seamlessly together, making the home ideal for both everyday living and entertaining. With two bedrooms one on each level, and a three-quarter bathroom on each floor, the thoughtfully designed layout provides privacy and convenience. First-floor laundry is tucked neatly into the bathroom, while the spacious landing at the top of the stairs offers flexible space for a home office, reading nook, workout area, or hobby room. The full insulated basement provides exceptional storage with the potential to suit a variety of future needs. Outside, the property features a beautiful mix of open land and woods, offering endless opportunities for gardening, recreation, hobby farming, or simply enjoying Vermont's natural beauty. A classic barn adds both character and practical storage, while the large covered front porch and concrete patio create the perfect spaces to relax, entertain, or take in the peaceful surroundings. Combining rustic charm with everyday functionality, this inviting property offers the privacy of country living while remaining just minutes from the shops, restaurants, and amenities of downtown Middlebury.

2 Beds ⋅ 2 Baths ⋅ 5103079 MLS

Set on 10 private acres, this charming log home offers the perfect balance of privacy, open lawn, and wooded surroundings, creating a peaceful Vermont retreat just 10 minutes from downtown Middlebury. Inside, the warm wood interior, high ceilings, and skylights fill the home with an abundance of natural light, creating a bright and inviting atmosphere throughout. The open-concept living room, dining area, and kitchen flow seamlessly together, making the home ideal for both everyday living and entertaining. With two bedrooms one on each level, and a three-quarter bathroom on each floor, the thoughtfully designed layout provides privacy and convenience. First-floor laundry is tucked neatly into the bathroom, while the spacious landing at the top of the stairs offers flexible space for a home office, reading nook, workout area, or hobby room. The full insulated basement provides exceptional storage with the potential to suit a variety of future needs. Outside, the property features a beautiful mix of open land and woods, offering endless opportunities for gardening, recreation, hobby farming, or simply enjoying Vermont's natural beauty. A classic barn adds both character and practical storage, while the large covered front porch and concrete patio create the perfect spaces to relax, entertain, or take in the peaceful surroundings. Combining rustic charm with everyday functionality, this inviting property offers the privacy of country living while remaining just minutes from the shops, restaurants, and amenities of downtown Middlebury.

35 N Leno Lane Ext, Middlebury

$379,000

Set on a picturesque 1.1-acre corner lot with a country feel, this beautifully maintained 1800s home offers the perfect blend of historic character, thoughtful updates, and exceptional versatility. The spacious, renovated eat-in kitchen serves as the heart of the home, featuring custom cabinetry, stainless-steel appliances, and plenty of room for gathering. The first floor also offers a generous living room with a wood stove and direct access to the backyard. A full bathroom with laundry hookups and a den with a fireplace complete the main level. Recently remodeled, the den could easily serve as a home office, formal sitting room, or playroom. Upstairs, you’ll find three bedrooms, including a spacious primary bedroom with an adjoining bonus room already equipped with plumbing beneath the floor. This flexible space offers the opportunity to create a dream walk-in closet, private nursery, home office, or future en suite bathroom. A second laundry area and three-quarter bathroom complete the upper level. Major improvements completed within the past eight years include a new roof, water heater, front deck, and extensive landscaping that has transformed the yard into a more functional outdoor space. The possibilities continue with an impressive collection of outbuildings. The attached garage offers space for three or more vehicles while still leaving room for storage or a workshop. A detached one-car garage and an additional barn with room for two more vehicles, multiple storage areas, hobby space, or potential home-business use provide incredible flexibility. Enjoy a country setting while remaining only 10 minutes from Middlebury College, Porter Medical Center, downtown Middlebury, local restaurants, shops, schools, and everyday amenities. Whether you’re looking for room to grow, space to work from home, extensive garage and workshop space, or a historic Middlebury property with endless potential, this one-of-a-kind home is ready to welcome its next owners.

3 Beds ⋅ 2 Baths ⋅ 5102314 MLS

Set on a picturesque 1.1-acre corner lot with a country feel, this beautifully maintained 1800s home offers the perfect blend of historic character, thoughtful updates, and exceptional versatility. The spacious, renovated eat-in kitchen serves as the heart of the home, featuring custom cabinetry, stainless-steel appliances, and plenty of room for gathering. The first floor also offers a generous living room with a wood stove and direct access to the backyard. A full bathroom with laundry hookups and a den with a fireplace complete the main level. Recently remodeled, the den could easily serve as a home office, formal sitting room, or playroom. Upstairs, you’ll find three bedrooms, including a spacious primary bedroom with an adjoining bonus room already equipped with plumbing beneath the floor. This flexible space offers the opportunity to create a dream walk-in closet, private nursery, home office, or future en suite bathroom. A second laundry area and three-quarter bathroom complete the upper level. Major improvements completed within the past eight years include a new roof, water heater, front deck, and extensive landscaping that has transformed the yard into a more functional outdoor space. The possibilities continue with an impressive collection of outbuildings. The attached garage offers space for three or more vehicles while still leaving room for storage or a workshop. A detached one-car garage and an additional barn with room for two more vehicles, multiple storage areas, hobby space, or potential home-business use provide incredible flexibility. Enjoy a country setting while remaining only 10 minutes from Middlebury College, Porter Medical Center, downtown Middlebury, local restaurants, shops, schools, and everyday amenities. Whether you’re looking for room to grow, space to work from home, extensive garage and workshop space, or a historic Middlebury property with endless potential, this one-of-a-kind home is ready to welcome its next owners.

118 Three Mile Bridge Rd, Middlebury

$295,000

A rare opportunity to own 4.5± acres of developable land within the Town of Middlebury. This parcel offers an excellent blend of convenience, flexibility, and future potential. Not only are the utilities either at the road or already on the property but there are views to the West. This property has a strong foundation for a variety of residential development visions.

5102034 MLS

A rare opportunity to own 4.5± acres of developable land within the Town of Middlebury. This parcel offers an excellent blend of convenience, flexibility, and future potential. Not only are the utilities either at the road or already on the property but there are views to the West. This property has a strong foundation for a variety of residential development visions.

Tbd Route 7 North, Middlebury

$499,000

Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

3 Beds ⋅ 3 Baths ⋅ 5101838 MLS

Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

44 Barnes Brook Rd Unit 10.1, Middlebury

$279,000

Welcome to this well-maintained home offering comfortable one-level living on 1.4 wooded acres in a peaceful country setting. With over 1,800 square feet of living space, this 3-bedroom, 2-bath home features a spacious layout with generously sized rooms and plenty of opportunity to make it your own. The primary suite offers a private bath and ample closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Surrounded by mature trees, the property offers a peaceful setting with space to enjoy the outdoors, whether gardening, relaxing, or simply appreciating the privacy of the wooded landscape. Whether you're a first-time homebuyer, looking to downsize, or searching for an affordable property with room to personalize over time, this home presents an excellent opportunity with all that Middlebury has to offer. Conveniently located just minutes from downtown Middlebury, shopping, dining, Middlebury College, and outdoor recreation. Don't miss your chance to make this property your own. Schedule your showing today!

3 Beds ⋅ 2 Baths ⋅ 5101809 MLS

Welcome to this well-maintained home offering comfortable one-level living on 1.4 wooded acres in a peaceful country setting. With over 1,800 square feet of living space, this 3-bedroom, 2-bath home features a spacious layout with generously sized rooms and plenty of opportunity to make it your own. The primary suite offers a private bath and ample closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Surrounded by mature trees, the property offers a peaceful setting with space to enjoy the outdoors, whether gardening, relaxing, or simply appreciating the privacy of the wooded landscape. Whether you're a first-time homebuyer, looking to downsize, or searching for an affordable property with room to personalize over time, this home presents an excellent opportunity with all that Middlebury has to offer. Conveniently located just minutes from downtown Middlebury, shopping, dining, Middlebury College, and outdoor recreation. Don't miss your chance to make this property your own. Schedule your showing today!

76 N Forty Ln, Middlebury

$237,500

Welcome to this well-maintained 3-bedroom, 1-bath condominium in beautiful Middlebury, Vermont. This location is ideal for easy access to local shops, restaurants and parks and offers low-maintenance living. Inside, you'll find a bright, functional layout featuring newer carpeting, new kitchen appliances, and a new washer & dryer creating a fresh and inviting space to call home. The three spacious bedrooms provide flexibility for guests or a home office, while the full bath is designed for everyday ease. Step outside to enjoy the newly built back deck, perfect for relaxing with your morning coffee, entertaining friends, or enjoying Vermont's changing seasons. A full basement offers abundant storage space, giving you plenty of room for seasonal gear, hobbies, or extra belongings. Conveniently located just minutes from downtown Middlebury, you'll have easy access to local shops, restaurants, parks, schools, and all the charm this vibrant Vermont community has to offer. With its recent updates, generous storage, and excellent location, this condo is a wonderful opportunity to enjoy comfortable living in the heart of Addison County.

3 Beds ⋅ 1 Baths ⋅ 5101704 MLS

Welcome to this well-maintained 3-bedroom, 1-bath condominium in beautiful Middlebury, Vermont. This location is ideal for easy access to local shops, restaurants and parks and offers low-maintenance living. Inside, you'll find a bright, functional layout featuring newer carpeting, new kitchen appliances, and a new washer & dryer creating a fresh and inviting space to call home. The three spacious bedrooms provide flexibility for guests or a home office, while the full bath is designed for everyday ease. Step outside to enjoy the newly built back deck, perfect for relaxing with your morning coffee, entertaining friends, or enjoying Vermont's changing seasons. A full basement offers abundant storage space, giving you plenty of room for seasonal gear, hobbies, or extra belongings. Conveniently located just minutes from downtown Middlebury, you'll have easy access to local shops, restaurants, parks, schools, and all the charm this vibrant Vermont community has to offer. With its recent updates, generous storage, and excellent location, this condo is a wonderful opportunity to enjoy comfortable living in the heart of Addison County.

11 Ledgewood Ct, Middlebury

$499,000

Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The wrap-around, covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

3 Beds ⋅ 3 Baths ⋅ 5100817 MLS

Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The wrap-around, covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

86 Brush Ln Unit 10.7, Middlebury

$280,000

This vintage farmhouse-style home is full of character and classic architectural details. Original woodwork, solid wood doors, hardwood floors, and a seasonal sleeping porch showcase the home's timeless appeal. The main level features a centrally located propane stove in the living room, a spacious kitchen, and a first-floor bedroom with ¾ bathroom. Upstairs, you'll find three additional bedrooms, along with a bonus room that was previously used as a laundry room and still retains its hookups. The electrical system has been updated, and a new hot water tank was installed in 2024. Perched above the road on the edge of Buttolph Acres, this corner-lot property features a welcoming front porch and a spacious fenced side yard. Sidewalks right outside the front door lead all the way to Middlebury's public schools and provide convenient access to downtown shops, restaurants, and amenities. This is a rare chance to own a classic Middlebury home at a price point that leaves room to make it your own. Comfortable to live in while you make improvements, the home offers tremendous potential for buyers with vision. Whether you're searching for your next home, your next project, or an investment opportunity, this property invites you to breathe new life into a classic home in one of Middlebury's most convenient areas. The zoning may provide added flexibility for certain residential, office, service, or lodging uses, creating even more possibilities for future owners - buyers are encouraged to explore this further.

4 Beds ⋅ 2 Baths ⋅ 5099999 MLS

This vintage farmhouse-style home is full of character and classic architectural details. Original woodwork, solid wood doors, hardwood floors, and a seasonal sleeping porch showcase the home's timeless appeal. The main level features a centrally located propane stove in the living room, a spacious kitchen, and a first-floor bedroom with ¾ bathroom. Upstairs, you'll find three additional bedrooms, along with a bonus room that was previously used as a laundry room and still retains its hookups. The electrical system has been updated, and a new hot water tank was installed in 2024. Perched above the road on the edge of Buttolph Acres, this corner-lot property features a welcoming front porch and a spacious fenced side yard. Sidewalks right outside the front door lead all the way to Middlebury's public schools and provide convenient access to downtown shops, restaurants, and amenities. This is a rare chance to own a classic Middlebury home at a price point that leaves room to make it your own. Comfortable to live in while you make improvements, the home offers tremendous potential for buyers with vision. Whether you're searching for your next home, your next project, or an investment opportunity, this property invites you to breathe new life into a classic home in one of Middlebury's most convenient areas. The zoning may provide added flexibility for certain residential, office, service, or lodging uses, creating even more possibilities for future owners - buyers are encouraged to explore this further.

89 Court St, Middlebury

$379,000

One level living is easy in this renovated condo! You will appreciate the updated wood floors throughout the entire unit. Natural light abounds in the open concept kitchen/living/dining area, and a new mini split is handy for both heat and air conditioning! The roomy kitchen has beautiful new quartz countertops, and newer appliances. A large pantry closet could house a stackable washer/dryer unit if you wanted that on the main floor. The living room leads out to a lovely deck, with beautiful plantings on a nearby ledge outcropping. It is a peaceful spot to enjoy a quiet moment at sunrise. Sunset can be enjoyed from the front of the unit. Two bedrooms and a full bath are conveniently on the main floor of the unit- with the same wood floors leading you through. A full basement is convenient for storage, and allows extra space for crafts, exercise or more finished space potential. A wood stove is on this level for an added heat source. A one car garage is in a detached structure nearby, which is handy- especially when the weather gets messy! Enjoy living a stone's throw from town and all it has to offer. The Middlebury Natural Foods Coop is minutes away, Town Hall Theater, Middlebury College and so many more fun places to see and take advantage of. It's time to simplify and enjoy the condo life!

2 Beds ⋅ 1 Baths ⋅ 5097100 MLS

One level living is easy in this renovated condo! You will appreciate the updated wood floors throughout the entire unit. Natural light abounds in the open concept kitchen/living/dining area, and a new mini split is handy for both heat and air conditioning! The roomy kitchen has beautiful new quartz countertops, and newer appliances. A large pantry closet could house a stackable washer/dryer unit if you wanted that on the main floor. The living room leads out to a lovely deck, with beautiful plantings on a nearby ledge outcropping. It is a peaceful spot to enjoy a quiet moment at sunrise. Sunset can be enjoyed from the front of the unit. Two bedrooms and a full bath are conveniently on the main floor of the unit- with the same wood floors leading you through. A full basement is convenient for storage, and allows extra space for crafts, exercise or more finished space potential. A wood stove is on this level for an added heat source. A one car garage is in a detached structure nearby, which is handy- especially when the weather gets messy! Enjoy living a stone's throw from town and all it has to offer. The Middlebury Natural Foods Coop is minutes away, Town Hall Theater, Middlebury College and so many more fun places to see and take advantage of. It's time to simplify and enjoy the condo life!

4 Overbrook Dr, Middlebury

$650,000

Nestled along the scenic banks of the Middlebury River, this beautifully updated vintage home offers a rare combination of historic character, modern comfort, and versatile living space. The main residence features three bedrooms plus a dedicated office, providing flexibility for remote work, guests, or hobbies. Enjoy peaceful mornings and relaxing evenings in the screened porch overlooking the property's lush gardens and natural surroundings. Thoughtful updates throughout preserve the home's timeless charm while enhancing everyday convenience. Upstairs there is a claw foot tub overlooking the beautiful yard, soak and listen to the river! A spacious barn adds exceptional storage, workshop, or hobby space, while the separate one-bedroom apartment presents opportunities for rental income, multigenerational living, or private guest accommodations. Surrounded by established gardens and the soothing sounds of the river, this special property offers a quintessential Vermont lifestyle with room to live, work, and entertain. As an added bonus, this property owns the land across the street ensuring a permanent buffer! Whether you're seeking a full-time residence, country retreat, or property with income potential, this riverside gem is a unique opportunity not to be missed. MOTIVATED SELLER!

4 Beds ⋅ 4 Baths ⋅ 5095929 MLS

Nestled along the scenic banks of the Middlebury River, this beautifully updated vintage home offers a rare combination of historic character, modern comfort, and versatile living space. The main residence features three bedrooms plus a dedicated office, providing flexibility for remote work, guests, or hobbies. Enjoy peaceful mornings and relaxing evenings in the screened porch overlooking the property's lush gardens and natural surroundings. Thoughtful updates throughout preserve the home's timeless charm while enhancing everyday convenience. Upstairs there is a claw foot tub overlooking the beautiful yard, soak and listen to the river! A spacious barn adds exceptional storage, workshop, or hobby space, while the separate one-bedroom apartment presents opportunities for rental income, multigenerational living, or private guest accommodations. Surrounded by established gardens and the soothing sounds of the river, this special property offers a quintessential Vermont lifestyle with room to live, work, and entertain. As an added bonus, this property owns the land across the street ensuring a permanent buffer! Whether you're seeking a full-time residence, country retreat, or property with income potential, this riverside gem is a unique opportunity not to be missed. MOTIVATED SELLER!

464 E Main St, Middlebury

$699,000

Picture yourself in a stunning retreat, where the gentle sound of a babbling river fills the air as you relax on your porch or savor a warm summer evening by the firepit. This classic Vermont farmhouse has been beautifully updated inside with a gorgeous custom kitchen complete with high end appliances that are a work of art. A 48" Italian gas range, Big Chill fridge and a handmade Moroccan brass faucet are just a few of the details! Custom cabinetry includes a bespoke island that is the center of the chef's domain. Throughout the home thoughtful design choices are around every corner. With an acceptable offer, the house can be sold mostly furnished! Wood floors throughout, and natural light is in abundance. A first floor bedroom and fully remodeled bath make one level living possible. The living and dining rooms feature built in cabinetry, and a wood burning fireplace is a focal point in the living room for cozy nights. Three additional bedrooms and another fully remodeled bath are upstairs, along with an office and large laundry room with hand stenciled floors. An attached sunporch is on the back of the home, with a cool bar for an amazing entertaining space. Walk outside and the magic begins there. Mature plantings, fruit trees, berry bushes, and open lawn space lead you back to the river. Nicely protected with a stone retaining wall, there are steps up and over to a cool riverside sitting area. From here you can cool off, sit and enjoy a cold drink, or just enjoy the soothing sounds of the river. Walking distance to the Waybury Inn for a delicious meal, or walk to the East Middlebury gorge, a beautiful and popular swimming hole. Tennis courts, library and a playground are nearby too! 8 miles (12 minutes) to the Snow Bowl for skiing in the winter. 5 miles (10 minutes) to Lake Dunmore for swimming in the summer. Enjoy the abundant hiking trails in the area as well! ALTHOUGH THIRD PARTY SITES SUCH AS ZILLOW SHOW OTHERWISE, THIS HOUSE IS NOT IN A FLOOD ZONE.

4 Beds ⋅ 2 Baths ⋅ 5094591 MLS

Picture yourself in a stunning retreat, where the gentle sound of a babbling river fills the air as you relax on your porch or savor a warm summer evening by the firepit. This classic Vermont farmhouse has been beautifully updated inside with a gorgeous custom kitchen complete with high end appliances that are a work of art. A 48" Italian gas range, Big Chill fridge and a handmade Moroccan brass faucet are just a few of the details! Custom cabinetry includes a bespoke island that is the center of the chef's domain. Throughout the home thoughtful design choices are around every corner. With an acceptable offer, the house can be sold mostly furnished! Wood floors throughout, and natural light is in abundance. A first floor bedroom and fully remodeled bath make one level living possible. The living and dining rooms feature built in cabinetry, and a wood burning fireplace is a focal point in the living room for cozy nights. Three additional bedrooms and another fully remodeled bath are upstairs, along with an office and large laundry room with hand stenciled floors. An attached sunporch is on the back of the home, with a cool bar for an amazing entertaining space. Walk outside and the magic begins there. Mature plantings, fruit trees, berry bushes, and open lawn space lead you back to the river. Nicely protected with a stone retaining wall, there are steps up and over to a cool riverside sitting area. From here you can cool off, sit and enjoy a cold drink, or just enjoy the soothing sounds of the river. Walking distance to the Waybury Inn for a delicious meal, or walk to the East Middlebury gorge, a beautiful and popular swimming hole. Tennis courts, library and a playground are nearby too! 8 miles (12 minutes) to the Snow Bowl for skiing in the winter. 5 miles (10 minutes) to Lake Dunmore for swimming in the summer. Enjoy the abundant hiking trails in the area as well! ALTHOUGH THIRD PARTY SITES SUCH AS ZILLOW SHOW OTHERWISE, THIS HOUSE IS NOT IN A FLOOD ZONE.

466 E Main St, Middlebury

$1,100,000

The classic Vermont farmhouse is on the market! This iconic property also enjoys classic Vermont mountain views- both of the Adirondacks and the Green mountains- that will complete the package. Nestled onto the landscape, the residence is perched up off the road looking west over conserved land to the Adirondacks. This property calls to you with its wrap around porch and handsome details, to come take a look inside! The adjacent barn is part garage, part barn, with a large finished room at the end that is a fully insulated, heated studio space- complete with bathroom! Used for years by the current owners who are artists, but could also be a wonderful music space, home office or even potential guest quarters. The main house has a true Vermont mudroom- big enough for all of your gear- and the way most will enter your home. Once inside you will enjoy the large, eat in kitchen with wood fireplace and built in cabinetry, that enjoys those western views. Butternut from the property was used for most of the trim in the home! The living room is adjacent, and features wood floors and a wood stove that can heat the downstairs. A front parlour serves as another living room, and currently hosts the piano for musical gatherings. An office, powder room and laundry are also on this floor. The living spaces open up to the fabulous wrap around porch where you can lounge day or night to your heart's content. The gracious stairs bring you up to four bedrooms and 2 1/2 baths- enough room for you and your guests! Located just minutes to downtown Middlebury, but your own private oasis and land for gardening or animals. Come check out this beautiful home and make it yours!

4 Beds ⋅ 5 Baths ⋅ 5091765 MLS

The classic Vermont farmhouse is on the market! This iconic property also enjoys classic Vermont mountain views- both of the Adirondacks and the Green mountains- that will complete the package. Nestled onto the landscape, the residence is perched up off the road looking west over conserved land to the Adirondacks. This property calls to you with its wrap around porch and handsome details, to come take a look inside! The adjacent barn is part garage, part barn, with a large finished room at the end that is a fully insulated, heated studio space- complete with bathroom! Used for years by the current owners who are artists, but could also be a wonderful music space, home office or even potential guest quarters. The main house has a true Vermont mudroom- big enough for all of your gear- and the way most will enter your home. Once inside you will enjoy the large, eat in kitchen with wood fireplace and built in cabinetry, that enjoys those western views. Butternut from the property was used for most of the trim in the home! The living room is adjacent, and features wood floors and a wood stove that can heat the downstairs. A front parlour serves as another living room, and currently hosts the piano for musical gatherings. An office, powder room and laundry are also on this floor. The living spaces open up to the fabulous wrap around porch where you can lounge day or night to your heart's content. The gracious stairs bring you up to four bedrooms and 2 1/2 baths- enough room for you and your guests! Located just minutes to downtown Middlebury, but your own private oasis and land for gardening or animals. Come check out this beautiful home and make it yours!

1844 Halladay Rd, Middlebury

$549,000

Built in 1813 by Timothy C. Strong, a Middlebury printer, 21 Seminary Street is an example of slow days from a different time. The property still boasts unique historical details like 25 inch wide pine flooring as well as the original staircase to the second floor. The home is currently setup as a single family with an apartment in the rear of the first floor, but is zoned to allow multiple possiblities such as a home based occupation or bed and breakfast. With a total of 5 bedrooms, 5 bathrooms and over 3600 finished square feet, there is so much opportunity to personalize a layout that best suits your wants and needs. The rear of the home is part of a newer addition that includes a 1 bedroom apartment with 3/4 bathroom, living room and office. Adjacent to the apartment is a 2 car garage that was also part of this addition. Above both is a large timber frame family or primary bedroom with vaulted ceilings, custom built ins, and a 3/4 bathroom. The property is priced well below recent appraisal at just over $150/square foot to enable the new owner to create their own vision of this historic home with exterior updates. Conveniently walkable to all of Middlebury's downtown offerings. Imagine village living at its best!

5 Beds ⋅ 5 Baths ⋅ 5091320 MLS

Built in 1813 by Timothy C. Strong, a Middlebury printer, 21 Seminary Street is an example of slow days from a different time. The property still boasts unique historical details like 25 inch wide pine flooring as well as the original staircase to the second floor. The home is currently setup as a single family with an apartment in the rear of the first floor, but is zoned to allow multiple possiblities such as a home based occupation or bed and breakfast. With a total of 5 bedrooms, 5 bathrooms and over 3600 finished square feet, there is so much opportunity to personalize a layout that best suits your wants and needs. The rear of the home is part of a newer addition that includes a 1 bedroom apartment with 3/4 bathroom, living room and office. Adjacent to the apartment is a 2 car garage that was also part of this addition. Above both is a large timber frame family or primary bedroom with vaulted ceilings, custom built ins, and a 3/4 bathroom. The property is priced well below recent appraisal at just over $150/square foot to enable the new owner to create their own vision of this historic home with exterior updates. Conveniently walkable to all of Middlebury's downtown offerings. Imagine village living at its best!

21 Seminary St, Middlebury

$470,000

This updated mid-century home features new flooring and fresh interior paint. Step outside onto the new back deck, the perfect place to entertain, relax, and take in views of your own private slice of Vermont. Set on 1.1 acres, the property offers plenty of space for a vegetable garden and complements the existing perennial plantings. The spacious home is conveniently located just minutes from Middlebury College, Porter Medical Center, and the Middlebury Natural Foods Co-op, while Burlington International Airport is only 52 minutes away. The oversized two-car garage provides ample room for vehicles, hobbies, and storage, with an additional separate workshop or storage area located at the rear. Outdoor enthusiasts will also appreciate the home's close proximity to several walking trails and recreation opportunities.

3 Beds ⋅ 2 Baths ⋅ 5090864 MLS

This updated mid-century home features new flooring and fresh interior paint. Step outside onto the new back deck, the perfect place to entertain, relax, and take in views of your own private slice of Vermont. Set on 1.1 acres, the property offers plenty of space for a vegetable garden and complements the existing perennial plantings. The spacious home is conveniently located just minutes from Middlebury College, Porter Medical Center, and the Middlebury Natural Foods Co-op, while Burlington International Airport is only 52 minutes away. The oversized two-car garage provides ample room for vehicles, hobbies, and storage, with an additional separate workshop or storage area located at the rear. Outdoor enthusiasts will also appreciate the home's close proximity to several walking trails and recreation opportunities.

95 Seminary Street Extension, Middlebury

$499,000

Looking for somewhere truly special to call home? This exceptional property offers 2,140 square feet of beautifully finished living space with 3 bedrooms, 2 baths, and breathtaking Green Mountain views from its private backyard and expansive deck. Meticulously rebuilt from top to bottom by the builder-owner, this home delivers the quality, efficiency, and peace of mind of new construction. Features include durable 2x6 wall construction, a standing seam metal roof, maintenance-free siding, new windows and doors, updated 200-amp electrical service, and FHA heating with an A-coil already installed for future air conditioning. Inside, the bright, open-concept design is filled with natural light and showcases vaulted ceilings, dramatic architectural lines, modern finishes, and a striking stone chimney centerpiece. The thoughtfully designed kitchen is perfect for entertaining, featuring extensive cabinetry, stainless steel appliances, granite and maple butcherblock countertops, a tiled backsplash, and a large center island with seating. The adjoining living and dining spaces flow seamlessly together, creating a warm and inviting atmosphere. The primary suite offers a peaceful retreat with scenic views and an updated bath, while additional bedrooms provide flexibility for guests, a home office, or family living. The fully finished lower level adds valuable living space and includes a new egress window, making it ideal for a recreation room, media room, gym, guest accommodations, or workspace. Outside, attractive stonework, cedar shake accents, vibrant siding, and an oversized detached garage enhance the home's curb appeal and functionality. The generous lot provides privacy and room to enjoy Vermont's beauty in every season. Located just minutes from Middlebury's amenities, this move-in-ready home offers an unmatched combination of craftsmanship, comfort, efficiency, and Vermont charm. The list of improvements goes on and on, but this is one property that must be seen.

3 Beds ⋅ 2 Baths ⋅ 5090473 MLS

Looking for somewhere truly special to call home? This exceptional property offers 2,140 square feet of beautifully finished living space with 3 bedrooms, 2 baths, and breathtaking Green Mountain views from its private backyard and expansive deck. Meticulously rebuilt from top to bottom by the builder-owner, this home delivers the quality, efficiency, and peace of mind of new construction. Features include durable 2x6 wall construction, a standing seam metal roof, maintenance-free siding, new windows and doors, updated 200-amp electrical service, and FHA heating with an A-coil already installed for future air conditioning. Inside, the bright, open-concept design is filled with natural light and showcases vaulted ceilings, dramatic architectural lines, modern finishes, and a striking stone chimney centerpiece. The thoughtfully designed kitchen is perfect for entertaining, featuring extensive cabinetry, stainless steel appliances, granite and maple butcherblock countertops, a tiled backsplash, and a large center island with seating. The adjoining living and dining spaces flow seamlessly together, creating a warm and inviting atmosphere. The primary suite offers a peaceful retreat with scenic views and an updated bath, while additional bedrooms provide flexibility for guests, a home office, or family living. The fully finished lower level adds valuable living space and includes a new egress window, making it ideal for a recreation room, media room, gym, guest accommodations, or workspace. Outside, attractive stonework, cedar shake accents, vibrant siding, and an oversized detached garage enhance the home's curb appeal and functionality. The generous lot provides privacy and room to enjoy Vermont's beauty in every season. Located just minutes from Middlebury's amenities, this move-in-ready home offers an unmatched combination of craftsmanship, comfort, efficiency, and Vermont charm. The list of improvements goes on and on, but this is one property that must be seen.

2801 Rte 7 S, Middlebury

$489,000

Here is a delightful opportunity to own a simply versatile property that has been carefully updated over the years. What started as a single family home has been beautifully transformed to this multi-use property. The larger section of the property includes 5 private office spaces that share a conference room and a reception area as well as a full bath and small kitchenette. The total rent for three of these office spaces currently brings in $1200 and could be even more if rents were adjusted for market rates and the two, currently empty, other offices were rented. There are two furnished studio apartments, one on each level. The 1st floor apartment is currently rented for $1150/month and is heated with both a Rinnai heater and a heated and cooled with a heat pump. It includes a dishwasher, electric stove, stacked laundry and a 3/4 bath. This unit shares a door with one of the aforementioned office spaces so it's possible you could "capture" that room for this apartment space. The second floor unit is a true studio space with a Rinnai heater, heat pump, electric stove, fridge and 3/4 bath and rents for $1400/month. There is additional income potential - rent the 2 bay garage or add that space to one of the apartment rentals and increase the rent. The property is landscaped and has an existing sign for business name display. The parking surface is paved and this property is very tidy!

5089982 MLS

Here is a delightful opportunity to own a simply versatile property that has been carefully updated over the years. What started as a single family home has been beautifully transformed to this multi-use property. The larger section of the property includes 5 private office spaces that share a conference room and a reception area as well as a full bath and small kitchenette. The total rent for three of these office spaces currently brings in $1200 and could be even more if rents were adjusted for market rates and the two, currently empty, other offices were rented. There are two furnished studio apartments, one on each level. The 1st floor apartment is currently rented for $1150/month and is heated with both a Rinnai heater and a heated and cooled with a heat pump. It includes a dishwasher, electric stove, stacked laundry and a 3/4 bath. This unit shares a door with one of the aforementioned office spaces so it's possible you could "capture" that room for this apartment space. The second floor unit is a true studio space with a Rinnai heater, heat pump, electric stove, fridge and 3/4 bath and rents for $1400/month. There is additional income potential - rent the 2 bay garage or add that space to one of the apartment rentals and increase the rent. The property is landscaped and has an existing sign for business name display. The parking surface is paved and this property is very tidy!

2337 Vt Route 7, Middlebury

$388,900

Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This two-bedroom townhome will be ready for occupancy in May 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. Step inside the open concept first-floor living area, with a generous kitchen featuring an island with seating, Energy Star appliances, and direct access to a private deck, perfect for morning coffee or evening relaxation. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze. A powder room on this level is great for guests. Upstairs, you will find 2 spacious bedrooms and a full bath. The lower level provides private garage parking, laundry room with utility space, and a handy bonus room- perfect as a mudroom, storage, or exercise room. Future community amenities will include green space, a community garden, access to trails, and more. Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Inquire for more details! Photos are "Likeness Only"

2 Beds ⋅ 2 Baths ⋅ 5088391 MLS

Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This two-bedroom townhome will be ready for occupancy in May 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. Step inside the open concept first-floor living area, with a generous kitchen featuring an island with seating, Energy Star appliances, and direct access to a private deck, perfect for morning coffee or evening relaxation. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze. A powder room on this level is great for guests. Upstairs, you will find 2 spacious bedrooms and a full bath. The lower level provides private garage parking, laundry room with utility space, and a handy bonus room- perfect as a mudroom, storage, or exercise room. Future community amenities will include green space, a community garden, access to trails, and more. Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Inquire for more details! Photos are "Likeness Only"

41 Barnes Brook Rd Unit 9.2, Middlebury

$765,000

Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The wrap-around, covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

3 Beds ⋅ 3 Baths ⋅ 5085570 MLS

Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house ventilation system. The wrap-around, covered porch entry welcomes you into the home, and is perfect for morning coffee or evening relaxing. Enter into the open concept first-floor living area, with a generous kitchen featuring an oversized island with seating and Energy Star appliances. The kitchen transitions seamlessly into spacious dining and living areas, making entertaining a breeze, and a powder room for guests is nearby. The primary suite is on the main floor- to make one-level living possible! Upstairs, you will find 2 spacious bedrooms and full bath, along with an open area for lounging, office space, or playroom. The lower level provides private garage parking, gear-friendly mudroom, storage space, and laundry room. Future community amenities will include green space, community garden, access to trails, and more. Inquire for more details! Photos are "Likeness Only"

30 Barnes Brook Rd Unit 10.4, Middlebury

$130,000

BUILD THE SOLUTION. Address the high demand for residential space in Middlebury with this fully permitted & shovel-ready parcel. Whether you're envisioning modern multi-unit apartments or an eco-village, this lot is engineered for efficiency & affordability. Permitted for up to12 Bedrooms: Ideal for a high-occupancy single-family home or large-scale multi-bedroom apartment units. Substantial Footprint: Maximize your allowable building footprint to 4,000 sq. ft., offering the potential for up to 8,000 sq. ft. of total living space. Infrastructure Ready: Tap into a municipal water supply & utilize a permitted in-ground wastewater disposal system. All essential utilities are available & easily accessible street-side. With a growing trend toward sustainable & affordable living, this site is a premier candidate for new housing opportunities featuring: community-centric designs with shared green space (Co-Housing & Eco-Villages); diverse & accessible housing models for a modern workforce (Housing Co-ops); affordable & supportive alternative to fully independent living (Congregate Living); or cost efficient & high-density living opportunities with long-term potential (Investment Property). This site is conveniently located near US Route 7, & VT Routes 116 & 125, providing easy access to essential amenities, popular attractions, & surrounding communities. Only steps away from the local bakery, store, post office, library, park, tennis court, restaurant, & bus stop.

5084490 MLS

BUILD THE SOLUTION. Address the high demand for residential space in Middlebury with this fully permitted & shovel-ready parcel. Whether you're envisioning modern multi-unit apartments or an eco-village, this lot is engineered for efficiency & affordability. Permitted for up to12 Bedrooms: Ideal for a high-occupancy single-family home or large-scale multi-bedroom apartment units. Substantial Footprint: Maximize your allowable building footprint to 4,000 sq. ft., offering the potential for up to 8,000 sq. ft. of total living space. Infrastructure Ready: Tap into a municipal water supply & utilize a permitted in-ground wastewater disposal system. All essential utilities are available & easily accessible street-side. With a growing trend toward sustainable & affordable living, this site is a premier candidate for new housing opportunities featuring: community-centric designs with shared green space (Co-Housing & Eco-Villages); diverse & accessible housing models for a modern workforce (Housing Co-ops); affordable & supportive alternative to fully independent living (Congregate Living); or cost efficient & high-density living opportunities with long-term potential (Investment Property). This site is conveniently located near US Route 7, & VT Routes 116 & 125, providing easy access to essential amenities, popular attractions, & surrounding communities. Only steps away from the local bakery, store, post office, library, park, tennis court, restaurant, & bus stop.

2 Wilmar St, Middlebury