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

$295,000

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

3 Beds ⋅ 2 Baths ⋅ 5101940 MLS

Charming 3-bedroom home located in Middlebury. This well-maintained property is both bright and functional with a layout that has comfortable living spaces, good-sized bedrooms, storage and even a bonus room. The sunny level backyard is perfect for gardening, outdoor play and entertaining. There is also a handy shed for your lawn equipment or extra storage. Located close to schools and offering an easy commute to Middlebury College, Porter Medical Center or longer commutes to Burlington and Rutland. A great opportunity for those seeking a convenient in town location, low maintenance, with a lovely outdoor space in a neighborhood setting.

149 Rogers Rd, Middlebury

$499,000

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

$299,000

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

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

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

$299,000

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

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

$679,000

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.

464 E Main St, Middlebury

$79,500

3 Beds ⋅ 1 Baths ⋅ 5095865 MLS

Affordable living in Middlebury Mobile Home Park. This home was originally a three-bedroom and has been thoughtfully converted to a two-bedroom, creating a spacious primary bedroom. Accessibility features include a walk-in shower and a ramp for easy entry. Significant upgrades completed in 2019 include new windows, siding, hot water tank, oil tank, and additional improvements. The property offers a well-kept shed, a fenced garden space, and a large lot within the park. Mature trees and established perennials create a peaceful, inviting outdoor setting. Lot rent is $435 per month and includes septic, water, rubbish and recycling services, and snowplowing to the driveway. Park approval is required. Application is attached.

62 Lindale Cir, Middlebury

$699,000

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

$399,000

3 Beds ⋅ 1 Baths ⋅ 5093934 MLS

***NEW PRICING*** Now includes +/- .48 building lot located at 28 Kings Row. Property has tremendous potential with the ability to purchase two lots. 26 Kings has a thoughtfully designed one-level home tucked away off the town maintained cul-de-sac, offering tranquility and privacy while keeping you close to the convenience and amenities of downtown living. Located at the end of Kings Row, the property feels like a private retreat, an oasis removed from the bustle of Middlebury, yet still benefits from public utilities and local access. Hardwood floors run throughout much of the home, and the easy flow of the layout adds to its welcoming feel. It is ready for its next owner to make the most of village living. A detached barn, currently used as a studio and featuring finished space upstairs, adds flexibility and opens the door to a variety of possible uses. Whether an investor looking to maximize opportunity, or a residential user, looking for a home with added potential, this property has so much potential!

26 And 28 Kings Row, Middlebury

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