Middlebury Real Estate

Welcome to Middlebury, a picturesque town nestled in the heart of Addison County, Vermont. Known for its vibrant community, stunning natural beauty, and rich history, Middlebury offers a unique blend of small-town charm and modern amenities.

Middlebury is home to Middlebury College, a prestigious liberal arts institution that adds a youthful energy to the town. The college campus, with its historic buildings and sprawling green spaces, is a focal point of the community and offers a wide range of cultural and educational events throughout the year.

Outdoor enthusiasts will appreciate Middlebury's proximity to the Green Mountains and the many opportunities for hiking, skiing, and exploring the great outdoors. The nearby Lake Champlain provides ample opportunities for water sports and fishing, making it a popular destination for nature lovers.

In the heart of downtown Middlebury, you'll find a vibrant arts and culture scene, with galleries, boutiques, and restaurants showcasing the best of local talent and flavors. The town's historic architecture, including the iconic Middlebury Inn, adds to its charm and character.

Whether you're looking to settle down in a close-knit community or seeking a weekend getaway in a beautiful setting, Middlebury has something for everyone. Come explore all that this charming town has to offer and discover why Middlebury is a hidden gem in Vermont's Addison County.

Newest Listings in Middlebury

$549,000

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

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

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

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

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

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

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

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

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

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

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

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

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