$549,000 $270 per sq.ft. Middlebury VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2037  |  Acres: 0.21
Friday Oct 3, 2025
Description: This classic village home is in a great location! Situated on South St., with sidewalks on both sides of the historical street as you head into town. You have no doubt driven by this home and admired its handsome Colonial facade many times. A brand new natural gas boiler has been installed! From the front door you enter into the living room space, with wood floors that continue throughout the home. A pellet stove makes things extra cozy, and built in bookcases line one wall of this space. A den allows for an additional living area, perfect for tv watching. A formal dining room is adjacent to the kitchen which is at the rear of the home, leading to the back yard. An office, 3/4 bathroom and laundry room/pantry round out this floor. Upstairs you will find three bedrooms and an additional 3/4 bath. The large, level lot provides space for your gardens, and is fenced in for privacy and keeping pets safe. Walk to downtown Middlebury for shopping, restaurants, library or the many events that take place all year long! Middlebury College is also within walking distance, so you can enjoy sporting events, walk the trails around the campus or check out the museum, theater or musical performances. Porter Hospital is just down the road as well. In town living at its best! See MLS Property & Listing Details & 31 images. Includes a Virtual Tour

$549,000 $429 per sq.ft. Middlebury VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1976  |  Acres: 0.5
Friday May 22, 2026
Description: 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. See MLS Property & Listing Details & 48 images.

$549,000 $151 per sq.ft. Middlebury VT Home »

5 Beds | 5 Baths |   Total Sq. Ft. 3630  |  Acres: 0.22
Thursday May 28, 2026
Description: 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! See MLS Property & Listing Details & 49 images.

$585,000 $464 per sq.ft. Middlebury VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1516  |  Acres: 0
Saturday Aug 9, 2025
Description: 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" See MLS Property & Listing Details & 8 images.

$595,000 $191 per sq.ft. Middlebury VT Home »

Waterfront on River Middlebury River
5 Beds | 4 Baths |   Total Sq. Ft. 3116  |  Acres: 0.95
Tuesday Jun 9, 2026
Description: 1840 Village Home. This great multi-generational or multi-family home has four bedrooms in the main house, an eat-in kitchen with pantry/laundry room, formal dining room, large family room with gas burning soapstone stove, office/craft room, music room/den and 3.5 baths. One bedroom apartment has large living room, walk-in closet, and full kitchen and bath. Ideal as a mother-in-law residence or income-producing apartment. Many recent upgrades including new furnace and appliances. Lots of built-ins, hardwood floors, and Vermont charm throughout. Welcoming front porches overlooking the Waybury Inn. Large, exceptional screened porch on rear of house looking out onto gardens, woods, and the Middlebury River. Large 1800s post-and-beam barn with heated workshop, concrete floor, and loft. See MLS Property & Listing Details & 37 images.

$679,000 $187 per sq.ft. Middlebury VT Home »

Price Change! Reduced by $16,000 down 2% on June 2nd 2026
5 Beds | 5 Baths |   Total Sq. Ft. 4840  |  Acres: 1.73
Wednesday May 13, 2026
Description: Perfect for anyone looking for an in-law suite, this home has a first-floor primary suite that is very spacious- giving its occupants a private space separate from the main house, including its own laundry room and office space! The generously sized mudroom entry and walk-in pantry separate this from the open concept kitchen/dining/living rooms. Flooded with natural light, the custom kitchen features granite countertops and cherry cabinetry! Sliding glass doors open up from the dining area to the expansive back deck! The soapstone wood stove in the living room sits on a custom-built stone hearth and can heat up this main level. The family room has pocket doors that can close it off from the rest of the main floor for added privacy. Upstairs are four more bedrooms and two baths! Loads of windows to enjoy the view out the back- a lovely, flat 1.73-acre parcel with stone walls, trees, lots of open space and established gardens, huge deck, pool, and plenty of sun! The partially finished basement has a large recreation room, workout room, workshop, play space, full bath AND plenty of storage. Located in East Middlebury village, down the street from the Waybury Inn, library and playground. Head up the mountain for great skiing, hiking and biking- or walk down the street to the Middlebury River to take a dip or go fishing! Less than 10 minutes into the village of Middlebury, where you'll find great restaurants, shopping, and events at Middlebury College. This house offers all of the space that you have been looking for, at the end of the road for a private setting- what more do you need?! See MLS Property & Listing Details & 51 images. Includes a Virtual Tour

$699,000 $260 per sq.ft. Middlebury VT Home »

Price Change! Reduced by $26,000 down 4% on July 8th 2026
182 Ft. of Waterfront on River Middlebury River
4 Beds | 2 Baths |   Total Sq. Ft. 2684  |  Acres: 0.6
Saturday Jun 13, 2026
Description: 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. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$699,000 $239 per sq.ft. Middlebury VT Home »

Waterfront on River Middlebury River
4 Beds | 4 Baths |   Total Sq. Ft. 2922  |  Acres: 1.82
Tuesday Jun 16, 2026
Description: 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. See MLS Property & Listing Details & 45 images. Includes a Virtual Tour

$765,000 $441 per sq.ft. Middlebury VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1938  |  Acres: 0
Thursday Mar 26, 2026
Description: 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" See MLS Property & Listing Details & 9 images.

$765,000 $441 per sq.ft. Middlebury VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1938  |  Acres: 0
Monday Apr 27, 2026
Description: 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" See MLS Property & Listing Details & 6 images.

$569,000 $387 per sq.ft. Middlesex VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1472  |  Acres: 104.79
Tuesday Jul 14, 2026
Description: This custom-built New England style Cape home has been lovingly cared for and in the same family since it was built in 1986. The home sits on an amazing 104+ acres of beautiful wooded land protecting wildlife and natural habitats. Enjoy hiking trails, hunting and exploring. The house is surrounded by gardens and peaceful landscape. Enter the open kitchen with a large dining area, surrounded by windows overlooking the perennial gardens. A cozy living room with a woodstove and one bedroom, and a full bath on the main level. Upstairs, you'll find three bedrooms, including the primary bedroom with wood floors, large closets, and another bathroom. Outside, above the stone walls, enjoy the perennial gardens, including several blueberry bushes, apple trees, and a special rose garden. Included with the home is a full-house generator, high speed internet with CV Fiber, a large wood shed, and a space for reviving the vegetable garden, which includes rhubarb and asparagus. An amazing location in Middlesex, only 15 minutes from Montpelier, where you can be surrounded by nature and stewardship for this special land. Your new home awaits! Open House Saturday 7/18 from 1-3pm. See MLS Property & Listing Details & 49 images.

$649,000 $381 per sq.ft. Middlesex VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2179  |  Acres: 16.2
Thursday May 7, 2026
Description: This must be the place--the one you've been waiting for. Set on over 16 acres in desirable Middlesex, 412 Macey Rd blends clean modern lines with warmth and character. This cedar post-and-beam contemporary is set back from the road on a peaceful parcel with mature perennial gardens and beautiful hardscaping, including a new bluestone patio. The recently updated TimberTech deck with sleek metal railings is bathed in year-round sunshine and perfect for morning coffee and long summer evenings. Enter through a spacious mudroom into the kitchen and dining area, where hardwood floors, a dramatic two-story wall of windows, and a cathedral ceiling create a bright, open feel. A Vermont Castings wood stove adds cozy ambiance. Completely remodeled in 2021, the kitchen is designed for the dedicated home cook. It features custom cabinetry, soapstone counters and sink, an oversized quarter sawn white oak island, a dual-fuel double-oven range, and vented hood. In the expansive living area, you will have plenty of space to spread out and relax, while a wall of built-in maple cabinetry (complete with window seat!) provides ample storage. Two bedrooms, each with a cold-weather heat pump, and a full bath complete the first floor. The open stairway with new cable rails leads to a lovely loft with built-in cherry and maple cabinetry; an ideal reading nook or office. The primary suite features cherry floors, two walk-in closets, a cold-weather heat pump, and multiple skylights. The luxurious en-suite bath shines with a walk-in Vermont slate shower, waterfall shower head, and soaking slipper tub. The walkout basement includes a large bonus room with numerous windows, offering excellent potential for a second living space. With modern updates including a high-speed EV charger, a heat pump hot water tank, new lighting throughout, and thoughtful improvements everywhere, this property truly covers all the bases. Don't miss the upgrades list attached! All offers due by 6pm on Monday, May 11 See MLS Property & Listing Details & 55 images.

$749,000 $499 per sq.ft. Middletown Springs VT Home »

Waterfront on Pond Unknown Pond
2 Beds | 4 Baths |   Total Sq. Ft. 1500  |  Acres: 4
Saturday Jun 13, 2026
Description: Outstanding 1840's Converted Post & Beam Barn to Home (2005). Vermont: #2 lowest crime · #1 lowest disaster risk · #1 climate migration destination 4 Acres, 3+B/3.5B, 2,100 sq. ft. Turn-key w/designer decor & fine antiques included. Private well (tested pure) + Spring Access · No Zoning. Waste water permit possible for ADU. South-facing view of valley, organic flat meadow, wood lot, raised garden beds, grape vines, stone walls, old maples. 94% of U.S. land has building or water restrictions...even in VT. This is the 6% that doesn't--and it's already built. Completed in 2005 by same design/build team behind Vermont's nationally recognized Hobbit House (-- rated top 5% of 8.1M listings by Airbnb, nearly 100 five-star reviews). Cooking: Gas stove, Cooling: 3 portable floor A/C units Heating & Domestic Water Combination Boiler: On demand. Propane boiler with radiant heat & floor heaters. (Radiant heat under slab in flex space, primary bath & mudroom.) Plus Wood Stove (works independently if required, heats entire 1st & 2nd floor). Wood: A season of stacked and dried wood protected from weather. Drilled well: with whole-house filter and water softener. Copper plumbing: Throughout. Extra full size fridge: In flex space. Appliances: All analog appliances that don't report back. Outdoor Shower: Hot & cold. Internet: Fiber Optic. Cell Service: ATT. See MLS Property & Listing Details & 24 images. Includes a Virtual Tour

$640,000 $410 per sq.ft. Monkton VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1560  |  Acres: 10.2
Tuesday Jul 7, 2026
Description: Nestled on 10.2 private acres in the rolling hills of Monkton, this beautifully maintained ranch offers the perfect blend of country living, modern updates, and room to grow. Surrounded by mountain views, open pastures, mature landscaping, and your own private pond, this property is a rare opportunity to enjoy Vermont at its finest. Inside, the home offers 3 bedrooms, 2 bathrooms, and an inviting open-concept layout where the kitchen, dining, and living spaces flow effortlessly together beneath vaulted ceilings and abundant natural light. A stunning gas fireplace creates a warm focal point in the living room, while the oversized picture window perfectly frames the surrounding countryside. First-floor living is made easy with a spacious primary suite, a first-floor laundry room with a convenient utility sink, and an attached two-car garage. A full, unfinished basement offers additional interior storage. The current owner has invested extensively in the property over the past two years, including a new roof (2026), newer rear deck, standby generator, heat pump water heater with water filtration, two heat pumps for whole-home heating/cooling, stainless steel kitchen appliances, updated vinyl plank flooring in the bathrooms and porch, extensive landscaping, and much more, providing peace of mind for years to come. Step outside and discover everything this incredible property has to offer. Grow your own food with five raised garden beds, asparagus and perennial plantings, and an established orchard featuring apple, pear, and plum trees. The private pond, chicken coop with run, oversized detached two-car garage, and expansive open land create endless possibilities for gardening, hobbies, animals, or simply enjoying the peaceful surroundings. Whether you are searching for a homestead, hobby farm, or simply a private retreat just minutes from Hinesburg and Bristol, 295 Church Road offers the space, privacy, and lifestyle that are becoming increasingly difficult to find. See MLS Property & Listing Details & 50 images.

$799,000 $275 per sq.ft. Monkton VT Home »

Price Change! Reduced by $36,000 down 5% on July 1st 2026
3 Beds | 3 Baths |   Total Sq. Ft. 2905  |  Acres: 5.5
Tuesday Jun 2, 2026
Description: This versatile 5.5-acre estate offers a rare blend of residential comfort and powerhouse commercial potential. Whether you are an entrepreneur seeking a flagship location or an investor looking for a multi-stream income property, this mixed-use gem delivers the space and infrastructure to bring your vision to life in the heart of Addison County. Ideally positioned just 10 minutes from Hinesburg, 15 minutes from Vergennes, and 25 minutes to Burlington International Airport. At the center of the property sits a well-maintained 3-bedroom, 2-bathroom home that radiates Vermont charm. The residence is designed for flexibility; it can serve as a comfortable primary home, a dedicated professional office suite, or a lucrative rental unit to offset your mortgage. Its proximity to the commercial workspace makes it an ideal setup for an owner-operator who values a thirty-second commute and the convenience of onsite quarters. The true crown jewel of this listing is the massive heated commercial warehouse. This expansive, high-clearance space is a blank canvas suited for a wide array of ventures, from professional automotive services and light manufacturing to specialized storage solutions. With reliable heating and a rugged layout, the facility ensures your business stays productive through every Vermont season. This is more than just a property; it is a strategic asset offering the freedom to grow your enterprise while enjoying the scenic beauty and community spirit of the Bristol and Monkton area. Experience the perfect synergy of work and life on this unique Vermont acreage. See MLS Property & Listing Details & 53 images.