Bennington County VT Homes for Sale

/62
$499,900
- 4 Beds
- 2.5 Baths
- 2,240 Sq Ft
679 Middle Pownal Rd, Pownal, VT 05261

Nestled in the heart of rural Pownal, this beautifully renovated 4-bedroom, 3-bath home offers the perfect blend of modern comfort and peaceful countryside living. Set on 12.1 picturesque acres, the property features a mix of open level land and serene wooded areas, ideal for hobby farming, equestrian use, or simply enjoying nature. Inside, you'll find a spacious and thoughtfully designed layout

Erin Vincent

BISHOP WEST REAL ESTATE

(802) 636-6092

679 Middle Pownal Rd, Pownal, VT 05261
/60
$1,600,000
- 5 Beds
- 4.5 Baths
- 4,243 Sq Ft
397 Fern Hill, Dorset, VT 05251

Take a drive up Nichols Hill Road to Fern Hill and head to the very top of the long bending driveway to find a serene, picturesque artist’s retreat 3 minutes from historic Dorset Village. Refreshingly private, quiet and secluded, drenched in natural light. With broad mountain vistas of Mother Myrick and Merck Forest, the top of the property backs gently into a beautiful private forest. The entire

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 644-3043

397 Fern Hill, Dorset, VT 05251
/47
$1,500,000
- Land
- 39 Acres
- $38,890 per Acre
500 Nims Rd, Dorset, VT 05251

This Majestic and Private 38 + acre parcel located nearby the Dorset Village, is tucked away on an elevated and prepped site which just happens to be one of the most dreamy and picturesque estate quality lands offered in all of Dorset. Just a mile from the Dorset Green and perched up on a knoll with nothing less than amazing mountain views to the south, east and the north. Absolutely stunning

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 634-4776

500 Nims Rd, Dorset, VT 05251
/2
$225,000
- 6 Beds
- 2 Baths
- 2,112 Sq Ft
303-305 Gage St, Bennington, VT 05201

Low maintenance duplex in Bennington. Offering good rental history and income. 2 -3 bedroom units, newer systems, vinyl siding and more. Walking distance to town. schools and recreation.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 471-3314

303-305 Gage St, Bennington, VT 05201
/60
$1,150,000
- 3 Beds
- 3 Baths
- 2,267 Sq Ft
636 Dexter Rd, Shaftsbury, VT 05262

In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic local backroads to write “Stopping by the Woods on a Snowy Evening." The Dexter Road Farmhouse, dating back 225 years, remains a testament to the enduring charm of Vermont and the simpler rhythms of country life. Nestled at the end of a serene, tree-lined town road, this charming 1800 farmhouse captures the

Kristin Comeau

TPW Real Estate

(802) 520-1220

636 Dexter Rd, Shaftsbury, VT 05262
/4
$249,000
- 5 Beds
- 3 Baths
- 2,184 Sq Ft
137 Park St, Bennington, VT 05201

Terrific income producing property. 2 - 1 bedroom units and a 3 bedroom unit with a garage. Close to town and modern systems. Good rental history. Is in a flood zone but owner has found a good flood insurance company.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 444-8271

137 Park St, Bennington, VT 05201
/60
$1,100,000
- 4 Beds
- 2.5 Baths
- 3,215 Sq Ft
92 Coventry Ln, Manchester Center, VT 05255

Coventry House - Offered For The First Time! Built in 1972, the home was thoughtfully designed by local architect Charles "Bud" Lynch in collaboration with the owners. This custom-built home blends timeless design with natural surroundings. Offering a country kitchen, 4 bedrooms and 3+ vintage baths reflecting the 70’s era focus on color, natural materials, and open floor plans all on one level

Kristin Comeau

TPW Real Estate

(802) 424-8410

92 Coventry Ln, Manchester Center, VT 05255
/43
$699,000
- 4 Beds
- 3.5 Baths
- 5,700 Sq Ft
56 Mending Walls Rd, Manchester Center, VT 05255

Welcome to your next chapter in Manchester, Vermont.Tucked away in the sought-after Mending Walls community, this 4-bedroom, 4-bath home offers over 5,700 square feet of sun-filled space designed for both comfort and connection. Set on a private one-acre lot, it’s clean, unfurnished, and ready for you to make it your own.Inside, you’ll find warm wood floors, a chef’s kitchen with

Trent Stephens

Wohler Realty Group

(802) 215-6507

56 Mending Walls Rd, Manchester Center, VT 05255
/41
$295,000
- 5 Beds
- 2 Baths
- 1,588 Sq Ft
226 North St, Bennington, VT 05201

This beautifully detailed 1880 Victorian in Bennington's residential commercial district offers flexibility and income potential all in one. Currently operating as a successful, fully furnished Airbnb, this 5-bedroom, 2-bath property is ready for its next owner. Whether you're an investor looking for cash flow or a buyer seeking a spacious and charming single family home. The main level

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 327-7149

226 North St, Bennington, VT 05201
/13
$199,000
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
2017 East Rd, Shaftsbury, VT 05262

3 bedroom 2 bath, double wide on 1.49 acres in Shaftsbury. Offering good location, large yard, and convenient travel to town. Living room with new pellet stove, kitchen with modern appliances including newer stove and dining area. Outside a 2 car detached garage, storage sheds and front and rear porches. New carpet.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 798-5968

2017 East Rd, Shaftsbury, VT 05262
/60
$1,795,000
- 17 Beds
- 20 Baths
- 14,861 Sq Ft
3888 Vermont Route 7a, Shaftsbury, VT 05262

The historic Arlington Inn & Spa is the centerpiece of scenic Arlington, Vermont. It features a tavern, restaurant and massage spa room. There are 15 guest rooms in 3 buildings, and an antique event barn on over 3.5 beautifully landscaped acres. This unique property can easily be configured in many creative ways. It could remain as an inn with a restaurant and bar. It could become a restaurant

Vicki Wilson

Maple Leaf Realty

(802) 444-8317

3888 Vermont Route 7a, Shaftsbury, VT 05262
/38
$650,000
- 3 Beds
- 2.5 Baths
- 2,184 Sq Ft
359 Hickory Hill Rd, Bennington, VT 05201

Welcome to this beautifully updated Center Hall Colonial, privately set on 2.58 wooded acres at the end of a peaceful cul-de-sac just minutes from downtown and major highways. The three bedroom, two and half bath home is truly move in ready, offering the perfect balance of comfort, style, and privacy. Step inside to an open concept main level where the kitchen flows seamlessly into the

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 633-6530

359 Hickory Hill Rd, Bennington, VT 05201
/11
$179,900
- 4 Beds
- 2 Baths
- 2,643 Sq Ft
905 County St, Bennington, VT 05201

Recently this home was a 2 unit (up and down). The current owner has doing work to convert it into a large single family home. Currently 4 bedrooms, 2 bathrooms and many possible room configurations. Also could easily be converted back to a 2 Unit. Many possibilities to put your finishing touches on this property.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 204-5943

905 County St, Bennington, VT 05201
/4
$199,900
- 5 Beds
- 2 Baths
- 1,478 Sq Ft
32-34 Sage St, Bennington, VT 05257

Duplex in North Bennington offering 1 way street location. decent yard and 2 - 2 bedroom units. Good investment potential in a walkable and sought location. Town water and sewer.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 402-4994

32-34 Sage St, Bennington, VT 05257
/20
$750,000
- 4 Beds
- 5 Baths
- 6,650 Sq Ft
338 Main St, Bennington, VT 05201

Don't miss your opportunity to own one of the area's most prestigious properties. The "Marble Bank" is located at the intersection of US Route 7 and Vermont Route 9 and is currently the landmark Fiddlehead Gallery. This property offers unique and grand architecture to go along with its high visibility location. Downtown's redevelopment and thriving new businesses make this location even more

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 347-6655

338 Main St, Bennington, VT 05201
/21
$175,000
- Land
- 18 Acres
- $9,749 per Acre
0 U S 7, Pownal, VT 05261

Beautiful Pownal Valley views from almost wherever you stand on this 17.95 acre parcel. Zoned for commercial use along the road frontage and rural residential in back creates opportunities for different types of development.

Vicki Wilson

Maple Leaf Realty

(802) 327-8230

0 U S 7, Pownal, VT 05261
/40
$1,450,000
- 4 Beds
- 6 Baths
- 4,272 Sq Ft
1016 West Rd, Manchester Center, VT 05255

Manchester Village...an award winning architect transformed this "Sears & Roebuck" mini farmstead indo Living Art! Masterful execution of architectural detail at every turn. Circular landscaped drive ties the residence, garages, and the an impressive party barn together for year round use. The substantial covered stone porch enters the arts & crafts foyer.. with study to one side, ahead the

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 357-7462

1016 West Rd, Manchester Center, VT 05255
/4
$279,000
- 4 Beds
- 4 Baths
- 2,080 Sq Ft
123 Bradford St, Bennington, VT 05201

4 unit apartment building with great rental history and income. Front and back porches and balcony. Great location. Showings to begin 6/10/2024

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 210-1728

123 Bradford St, Bennington, VT 05201
/15
$115,000
- Land
- 2.90 Acres
- $39,655 per Acre
Lot 3 Route 11 30, Winhall, VT 05340

Spectacular West and Southerly Views over Manchester Valley and boasts a bird's eye view across to the Equinox Mountain!Located on the Manchester side of Winhall, this property is at the end of a private lane offering privacy... engineered and offering VT Waste Water and Potable Water Supply Permit: WW-2-3614, design for 3 BR single family residence. Bordered by the Green Mountain Nat'l

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 808-6197

Lot 3 Route 11 30, Winhall, VT 05340
/2
$20,000
- Land
- 3.00 Acres
- $6,667 per Acre
0 U S 7, Pownal, VT 05261

3 acre parcel located behind other parcels. Would be a great place for a hunting "camp", blind or recreation. Right of Way is from 63 Metcalfe Road, Pownal.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 210-3911

0 U S 7, Pownal, VT 05261
/2
$109,000
- Land
- 2.60 Acres
- $41,923 per Acre
0 Kesick Swamp Rd, Sunderland, VT 05250

Terrific 2.6 acre building lot in Sunderland. Located at the end of Kesick Swamp Road. Private and almost ready to go. Some site work has been done and a septic design for a 2 bedroom home has been completed, just needs permitting. Current owner will change from recreational use to Residential use, prior to closing.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 454-3023

0 Kesick Swamp Rd, Sunderland, VT 05250
/38
$475,000
- 3 Beds
- 3 Baths
- 1,710 Sq Ft
1243 Murray Hill Heights Rd Unit 43, Manchester, VT 05255

Set in the heart of Manchester’s desirable Murray Hill community, this 3-bedroom, 3-bath condo in the Heights offers over 1,700 sq. ft. of comfortable, light-filled living with breathtaking mountain views. Enjoy a spacious three-level layout that offers privacy for guests with one of bedrooms on the top floor. The main living area is perfect for relaxing or entertaining, featuring a

Julie Citron

RE/MAX Four Seasons

(802) 402-4782

1243 Murray Hill Heights Rd Unit 43, Manchester, VT 05255
/28
$85,000
- Land
- 3.75 Acres
- $22,667 per Acre
0 High Pine Dr, Arlington, VT 05250

Just a short walk to the Battenkill River and a stone's throw to the Village of Arlington, this 3.75 acre lot is already permitted for a 5BR house! Partial clearing has already been done and with some additional select clearing you can have lovely views while retaining privacy. A wonderful place for your primary residence or your Vermont getaway!

Vicki Wilson

Maple Leaf Realty

(802) 481-3309

0 High Pine Dr, Arlington, VT 05250
/39
$275,000
- 3 Beds
- 1.5 Baths
- 1,264 Sq Ft
139 Mckinley St, Bennington, VT 05201

Welcome to 139 McKinley Street in Bennington! This charming 1920 New Englander blends character and convenience in a great village location. Inside, you'll find a first-floor primary bedroom with laundry and a half bath downstairs, a cozy living room with a beautiful woodstove, and hardwood floors upstairs with easy care laminate throughout the main level.A standout feature is the

Brooke Thomson Drew

Mahar McCarthy Real Estate

(607) 437-6795

139 Mckinley St, Bennington, VT 05201
/35
$359,000
- 3 Beds
- 2 Baths
- 1,120 Sq Ft
33 Aspen Ln, Bondville, VT 05340

Minutes from Stratton Mountain, this cozy chalet offers the perfect mountain escape with timeless character and room to make it your own. Featuring a classic chalet style floor to ceiling stone fireplace and wood interior, this home exudes vintage alpine charm. There are three bedrooms, two baths and an open concept living space, providing plenty of room for gatherings or weekend getaways.

Alison Cummings

Cummings & Co

(802) 424-9210

33 Aspen Ln, Bondville, VT 05340
/16
$145,000
- 3 Beds
- 1.5 Baths
- 1,485 Sq Ft
755 Main St, Bennington, VT 05201

Many possibilities with this property located on Main Street in Bennington. Zoned village commercial but currently a 3 bedroom 1 and a half bath home. Nice kitchen, dining room, living room, main level primary with half bath, main level laundry and more. Needs some TLC. Won't qualify for first time homebuyer programs.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 444-8936

755 Main St, Bennington, VT 05201
/46
$895,000
- 5 Beds
- 2 Baths
- 2,424 Sq Ft
2 Cold Spring Rd, North Bennington, VT 05257

Welcome to 2 Cold Spring Road a cherished homestead steeped in history, beauty, and Vermont tradition. This 1785 Center Hall Colonial has been in the same family for generations and is now ready for its next chapter. With five spacious bedrooms, two full baths, and a classic layout that captures the warmth of country living, this property offers timeless charm with endless potential.Set on

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 810-8434

2 Cold Spring Rd, North Bennington, VT 05257
/60
$1,950,000
- 4 Beds
- 3.5 Baths
- 3,333 Sq Ft
1268 Myers Rd, Shaftsbury, VT 05262

Welcome to your paradise! This exquisite 30 acre estate offers extreme privacy, a custom home with architectural details throughout, a modern 1 BR guest apartment, a 2 car garage, top notch equestrian facilities, a trout and koi pond, and the list goes on and on. The winding driveway leads to a world away, as it opens to view of the exclusive estate in all of it's glory. The 3 Bedroom, 4000SF

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 441-6014

1268 Myers Rd, Shaftsbury, VT 05262
/36
$499,900
- 3 Beds
- 2 Baths
- 1,520 Sq Ft
1061 Granger Hollow Rd, North Bennington, VT 05257

Dreaming of a peaceful Vermont lifestyle? This three bedroom, 2 bath home sits on 11.5 acres of beautiful land with rolling open mountain views, a stream, mature apple trees, and an inground pool all the ingredients for your perfect retreat.Step inside to this home that has had a complete refresh. The home offers a first floor bedroom and full bath with a step in shower, making it great

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 481-3292

1061 Granger Hollow Rd, North Bennington, VT 05257
/10
$20,000
- Land
- 1.40 Acres
- $14,286 per Acre
0 Bergrucken Ln Unit 24262915, Stamford, VT 05352

1.4 Acres of Scenic Vacant Land in Bennington County, VT Located in Alpenwald VillageLooking for the perfect spot to build your dream home or vacation retreat? This 1.4-acre lot in Bennington County, Vermont offers an incredible opportunity! Located in the exclusive Alpenwald Village community, the property boasts 115 ft of road frontage on Bergrucken Ln, providing easy access while

Community Lands

0 Bergrucken Ln Unit 24262915, Stamford, VT 05352
/10
$20,000
- Land
- 1.20 Acres
- $16,667 per Acre
0 Oberdorf Rd Unit 24065553, Readsboro, VT 05350

1.2 Acres of Scenic Land for Sale in Bennington County, VTEscape to the beauty of Bennington County, Vermont, with this stunning 1.2-acre parcel of vacant land. Offering 350 ft of road frontage on Oberdorf Rd, this lot provides easy access and is nestled within the private Alpenwald Village, a peaceful community ideal for your dream home or vacation retreat. Surrounded by nature, this

Community Lands

0 Oberdorf Rd Unit 24065553, Readsboro, VT 05350
/36
$4,975,000
- 5 Beds
- 4 Baths
- 5,445 Sq Ft
527 Benson Rd, Manchester Center, VT 05255

Boorn Brook Farm combines the rich character of history and the comfort of contemporary living with complete privacy. Established in the late 1700s, the estate near Manchester Center offers stunning views of the Mt. Equinox and the Taconic Range. Surrounded by the Green Mountain National Forest, it creates a peaceful haven that balances the old and the new. For over 50 years, Marion Gould

Story Jenks LandVest, Inc/Woodstock

527 Benson Rd, Manchester Center, VT 05255
/24
$970,000
- 4 Beds
- 3.5 Baths
- 2,160 Sq Ft
10 Middle Ridge Rd, Winhall, VT 05155

Fox Chapel luxury townhome at Stratton. This four bedroom, four bathroom home is offered with the ability to skip the wait list at the Stratton Mountain Club. Renovated bathrooms and air conditioning make this the year round place to be. Prime location next to the ‘Chapel of the Snows’ and the Commons, walk to the Stratton village for ski access, dining, shopping, and resort amenities. Watch the

Christiane Carroccio TPW Real Estate

10 Middle Ridge Rd, Winhall, VT 05155
/57
$1,575,000
- 5 Beds
- 3.5 Baths
- 4,785 Sq Ft
671 West Rd, Manchester Center, VT 05255

Charming 1790 Manchester Village home with guest house and separate garage located in the heart of Manchester Village and just steps from restaurants, shops, and the Southern Vermont Arts Center. This beautifully maintained 5 bedroom, 3 1/2 bath home sits on 3.8 private acres of expansive lawn, manicured gardens, and outdoor entertaining space. The updated kitchen features a large island, a

Katherine Zilkha Four Seasons Sotheby's Int'l Realty

671 West Rd, Manchester Center, VT 05255
/43
$749,000
- 4 Beds
- 2 Baths
- 1,200 Sq Ft
86 Benson Fuller Dr, Bondville, VT 05340

Your Ultimate GetawayEscape to this idyllic Vermont retreat, where convenience meets relaxation. This spacious home offers everything you need for a fun-filled and carefree lifestyle, from outdoor entertaining to cozy indoor spaces.Step out onto the large deck and unwind by the gas fire pit table, or enjoy watching the friendly mini-golf matches below. In the cooler nights of winter,

Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

86 Benson Fuller Dr, Bondville, VT 05340
/40
$645,000
- 2 Beds
- 2 Baths
- 4,044 Sq Ft
5515 Main St, Manchester, VT 05255

Own a piece of Vermont history and enjoy the convenience of in-town living with this charming and versatile 1830s home, located right on Main Street. Zoned for mixed use (MU2), this 2 bedroom, 2 bath property with a full kitchen blends the charm of an old Vermont home with incredible work from home or business potential. Step inside to find a home full of character, enhanced by modern updates

Katherine Zilkha Four Seasons Sotheby's Int'l Realty

5515 Main St, Manchester, VT 05255
/52
$775,000
- 4 Beds
- 3.5 Baths
- 4,032 Sq Ft
77 Monument Ave, Bennington, VT 05201

Located in the prestigious Village of Old Bennington, this stately 4,000+ sq. ft. center hall Colonial sits on 1.6 beautifully landscaped acres with a year-round creek and charming footbridge. Thoughtfully maintained, it features updates including electrical, plumbing, new roofing, and rebuilt chimneys. A gracious foyer welcomes you, flanked by a formal parlor with fireplace and half bath,

Moira Spivey Four Seasons Sotheby's Int'l Realty

77 Monument Ave, Bennington, VT 05201
/53
$625,000
- 3 Beds
- 2 Baths
- 1,894 Sq Ft
190 Vt Route 11 Unit 1, Peru, VT 05152

Don't miss the opportunity to own this renovated 4 bedroom/ 2 full bath townhouse in Peru, VT. This tasteful and high end renovation will wow you. Combining the ambiance and character of a European mountain Chalet with the amenities and style of a contemporary mountain residence, this offers beautiful tiled luxury bathrooms and gourmet kitchen. The great room has vaulted wood beamed ceilings,

Robert Sabol Wohler Realty Group

190 Vt Route 11 Unit 1, Peru, VT 05152
/60
$1,825,000 Open House 8/30
- 3 Beds
- 4 Baths
- 2,872 Sq Ft
36 Beaver St, Bondville, VT 05340

Your Ultimate Vermont Mountain Retreat Awaits! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape—crafted for adventure, relaxation, and making lasting memories in every season. Whether you’re hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage, this property delivers! Plus, it's only a 10-minute

MaryKate Grey Stratton Real Estate

36 Beaver St, Bondville, VT 05340
/35
$799,000
- 3 Beds
- 2.5 Baths
- 2,230 Sq Ft
5 Linscott Rd Unit 56, Jamaica, VT 05343

This irresistible renovated Forest Farms contemporary with 3 bedrooms and 2 and a half baths has an inviting ambiance as well as appealing floor plan flow. Past the foyer with half bath is the open living concept with white oak hardwood floors. The glow and warmth of the raised hearth stone fireplace in the living area is shared from windowed dining area to bright kitchen with all new appliances,

Diana Stugger Four Seasons Sotheby's Int'l Realty

5 Linscott Rd Unit 56, Jamaica, VT 05343

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.