$299,000 $222 per sq.ft. Middlebury VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1344  |  Acres: 0.25
Listed on Wednesday Jul 15, 2026
Description: 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. See Listing Details & 56 images.

Under Contract Middlebury VT Home for sale $400,000 $220 per sq.ft.

$400,000 $220 per sq.ft. Middlebury VT Home »


Price Change! Reduced by $49,000 down 12% on July 7th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 1815  |  Acres: 0.26
Listed on Monday May 4, 2026
Description: This inviting home offers a bright, comfortable layout designed for easy everyday living. The main level flows naturally between the kitchen, dining and living spaces, creating a welcoming environment for gatherings or quiet evenings at home. The updated kitchen blends the convenience of modern living with the charm and character of an older home. Upstairs, a large full bath serves the bedroom level, providing both space and functionality. Outside, the fenced-in backyard is ideal for pets, play or gardening. The garage adds valuable storage and parking. Set on a small, manageable lot the property offers quick access to town amenities and is just a short drive to the Middlebury Snow Bowl. The location is ideal for commuting to Rutland or Burlington as well. The sidewalks in front of the house make it easy to enjoy a morning walk or an evening stroll. This home delivers comfort, practicality, and a great location. See Listing Details & 33 images.

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

5 Beds | 5 Baths |   Total Sq. Ft. 3630  |  Acres: 0.22
Listed on 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 Listing Details & 49 images.

Under Contract Middlebury VT Home for sale $595,000 $191 per sq.ft.

$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
Listed on 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 Listing Details & 37 images.

Under Contract Middlebury VT Home for sale $679,000 $187 per sq.ft.

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

5 Beds | 5 Baths |   Total Sq. Ft. 4840  |  Acres: 1.73
Listed on 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 Listing Details & 51 images. Includes a Virtual Tour

$679,000 $232 per sq.ft. Middlebury VT Home »


Price Change! Reduced by $20,000 down 3% on July 27th 2026
Waterfront on River Middlebury River
4 Beds | 4 Baths |   Total Sq. Ft. 2922  |  Acres: 1.82
Listed on 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 Listing Details & 45 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
Listed on 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 Listing Details & 60 images. Includes a Virtual Tour

$1,100,000 $392 per sq.ft. Middlebury VT Home »

4 Beds | 5 Baths |   Total Sq. Ft. 2804  |  Acres: 12
Listed on Friday May 29, 2026
Description: 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! See Listing Details & 60 images. Includes a Virtual Tour

$299,000 $210 per sq.ft. Middlesex VT Home »

4 Beds | 1 Baths |   Total Sq. Ft. 1426  |  Acres: 1
Listed on Tuesday Jul 21, 2026
Description: Welcome to this cozy four bedroom one bath home with an amazing attic just waiting for your creativity. Enjoy an evening with friends in your spacious backyard. Conveniently located just minutes from Montpelier with easy access to I-89. Experience the beauty of Lake Elmore or take in a local Mountaineers Baseball game within minutes. See Listing Details & 47 images.

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

4 Beds | 2 Baths |   Total Sq. Ft. 1472  |  Acres: 104.79
Listed on 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 Listing Details & 49 images.

Under Contract Middletown Springs VT Home for sale $299,000 $161 per sq.ft.

$299,000 $161 per sq.ft. Middletown Springs VT Home »


Price Change! Reduced by $30,900 down 10% on July 21st 2026
4 Beds | 2 Baths |   Total Sq. Ft. 1855  |  Acres: 9.91
Listed on Wednesday Apr 1, 2026
Description: Circa 1850 farmhouse with detached 2-car garage on 9.9 acre lot on scenic country road. Offering a large mud room before entering the spacious kitchen and walk-in pantry. The well proportioned dining room, living room and porch complete the 1st level of this home. Upstairs you will find three bedrooms and a bath. Upgrades include windows, insulation and heating system. Less than a 30 minute drive to Manchester and most of Rutland county this is the perfect centralized location. Make an appointment today to see this lovely property. Motivated Sellers - Bring your offer!! See Listing Details & 28 images.

$325,000 $188 per sq.ft. Middletown Springs VT Home »


Price Change! Reduced by $25,000 down 8% on July 30th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 2226  |  Acres: 1
Listed on Wednesday Jul 8, 2026
Description: Tucked away near the end of historic Montvert Road in the charming town of Middletown Springs and just a short walk from the renowned Mineral Springs Park, this peaceful Vermont property offers a true storybook setting. Situated on a picturesque one-acre lot, you'll enjoy the tranquility of nature from the comfort of your own backyard. Relax on the side deck with your morning coffee or unwind in the evening while listening to the river, watching deer, birds, and other wildlife wander through the neighboring meadow. Lovingly cared for by the same family for many years, this spacious ranch is ready for its next chapter. Designed for easy one-level living, the home offers generous living space for family and guests, with additional partially finished space in the lower-level featuring a cozy fireplace, half bath, and bar, perfect for entertaining, hobbies, or a recreation room. The main level fireplace creates a warm and inviting atmosphere, while both a wood furnace and an oil furnace provide flexible heating options for Vermont's changing seasons. An attached two-car garage offers ample space for vehicles and outdoor gear, and the well-maintained two-story barn, dating back to the 1850s, presents endless possibilities for storage, a workshop, studio, or recreational space. Whether you're drawn to its timeless character or envision updating it with your own personal style, this property offers an exceptional opportunity to create your dream home in an idyllic country setting. Conveniently located less than a mile from Middletown Springs Elementary School, with school choice beginning in seventh grade, and under 30 minutes from Rutland, this home provides the perfect balance of peaceful rural living and everyday convenience. If you've been dreaming of a place where you can slow down, embrace Vermont's natural beauty, and fall asleep to the calming sounds of the Poultney River, this special property is ready to welcome you home. See Listing Details & 42 images.

$529,900 $247 per sq.ft. Milford NH Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2148  |  Acres: 0.26
Listed on Wednesday May 13, 2026
Description: This inviting 2,148± sq. ft. New England Colonial sits on a beautifully landscaped corner lot on Nashua Street, offering classic charm and endless potential. Originally a single-family home, the property can be thoughtfully restored to a 4-bedroom residence or adapted for mixed-use living with town approval. Most recently used as office space, the first floor currently includes a reception area, private offices, conference room, kitchen/breakroom, and half bath can easily become a welcoming living room, dining room, family room, or even a first-floor bedroom. Upstairs, the second floor offers two private rooms, a half bath and a large open area--ideal for creating multiple bedrooms and a full bath. With a full attic and full basement, you'll have abundant storage and room to grow. Whether you're dreaming of a spacious home filled with character or envisioning a flexible live-work setup, this property is ready for your creativity. Renovations will be needed, so a cash purchase or construction loan will be required. See Listing Details & 47 images.

Under Contract Milford NH Home for sale $549,900 $267 per sq.ft.

$549,900 $267 per sq.ft. Milford NH Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2059  |  Acres: 0.23
Listed on Wednesday Jul 8, 2026
Description: **OFFER DEADLINE MONDAY JULY 13TH 5PM** Welcome to 15 Crosby Street, a charming New Englander filled with character and warmth! Offering 4 bedrooms, 3 bathrooms, and over 2,000 square feet of living space, this home provides plenty of room to spread out and make it your own. Step inside to find spacious rooms, beautiful wide pine floors, and classic details throughout. The inviting farmer's porch is the perfect spot to enjoy your morning coffee or unwind at the end of the day. Conveniently located close to Milford's vibrant downtown, local shops, restaurants, and everyday amenities, this home offers a wonderful combination of charm, space, and location. Come see all that 15 Crosby Street has to offer! Private showings begin Thursday, July 9th. Join us for an Open House on Saturday and Sunday from 11:00 AM-1:00 PM! See Listing Details & 54 images.

$575,000 $274 per sq.ft. Milford NH Home »


Price Change! Reduced by $24,000 down 4% on June 8th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 2100  |  Acres: 0.36
Listed on Wednesday Apr 15, 2026
Description: Tucked on a corner lot just moments from downtown Milford, this charming antique home blends in-town convenience with a warm, country feel. A welcoming covered front porch sets the tone, inviting you to slow down and enjoy the character that carries throughout. The yard offers space for pets, gardening, or even a few chickens, creating a peaceful setting that feels like home the moment you arrive. Inside, the first floor features an open kitchen and living area designed for everyday living, along with a cozy den or office--perfect for quiet mornings or working from home. A first-floor bedroom and full bath add flexibility for guests or single-level living. Upstairs, you'll find three additional bedrooms and another full bath, including a primary bedroom with direct access. Looking for more space? The room over the garage (accessible from the house or the garage) is already roughed in and ready for your finishing touches--ideal for a bonus room, studio, or private retreat. With a spacious garage, workshop area, and plenty of parking, this home offers both charm and opportunity. With a little vision and care, this special property can truly shine. Schedule your showing today! See Listing Details & 41 images.

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