New Listings for Sale in Bennington County, VT

41 homes

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NEW 9 HRS AGO

ABOUT THIS HOME
New Listing for sale in Bennington County, VT:
Follow the historic "Wilbur" Half-Mile Stone Wall along River Road in Manchester, and just beyond the Wilburton Inn, you’ll discover the private entrance to Riverbend Drive. Tucked into one of Southern Vermont’s most beautiful settings, Riverbend is an exclusive community of exceptional homes on beautifully maintained 2 to 4 acre lots. 601 Riverbend Drive is a stunning 4BR/3.5BA Colonial on a private 3.05-acre lot with sweeping mountain views and a welcoming circular driveway. Designed by Ramsey Gourd and built by Keelan and Company, the home showcases exceptional craftsmanship, custom millwork, native maple floors, and thoughtful details throughout. At the heart of th

$1,450,000

4 beds3.5 baths3,551 sq ft

601 Riverbend Dr, Manchester Center, VT 05254

Exclusive community • Private entrance • Circular driveway

NEW 12 HRS AGO

ABOUT THIS HOME
New Listing for sale in Bennington County, VT:
Very well appointed 2 bedroom 1 bathroom home with new heat pumps, stainless steel appliances, oversized garage and a walk up attic. New fenced in yard on just over an acre.

$379,000

2 beds1 bath1,276 sq ft

1580 Main Rd, Stamford, VT 05352

Walk up attic • New fenced in yard • Over an acre

NEW 13 HRS AGO

ABOUT THIS HOME
New Listing for sale in Bennington County, VT:
Escape to the mountains in this charming A-frame, ideally located between the bustling town of Manchester and the area's best ski mountains. This home is your perfect base for year-round adventure, putting you just minutes from world-class skiing, hiking, mountain biking, and shopping. Inside, you'll find a comfortable layout featuring 3 bedrooms, 2 bathrooms, and a home office that can easily flex to accommodate extra guests. Cozy up by the wood-burning fireplace after a day on the slopes or soak up the sun on the inviting deck. This isn't just a home; it's a gateway to the best of Vermont. Septic system is being replaced and completion date in early October.

$425,000

3 beds2 baths1,344 sq ft

3 Kimball Hill Rd #1, Winhall, VT 05340

Inviting deck • Home office • 1.03 acre lot

ABOUT THIS HOME
New Listing for sale in Bennington County, VT:
Set on 2.5 beautiful acres, this inviting Cape-style home offers a wonderful combination of comfortable living space, character, and versatile outbuildings. The primary suite is conveniently located on the main level, with two additional bedrooms and a full bath upstairs. An attached two-car garage provides convenient parking and additional storage. The spacious living room features wide pine floors, built-in cabinetry, a fireplace, and a slider leading to the deck. The dining room continues the charm with wide pine flooring, a large window, and a built-in corner cabinet. Outside, the property offers a large barn with two stalls and an expansive workshop, along with two additional sheds for

$349,000

3 beds2 baths1,616 sq ft

57 Paran Rd, Shaftsbury, VT 05262

Expansive workshop • 2.5 acres • Large barn

OPEN SEP 5, 10AM TO 12PM

ABOUT THIS HOME
New Listing for sale in Bennington County, VT:
Where Vermont Living Feels Effortless Dorset Home, Guest Cottage, Pond & Mountain Views Settle into the beauty of Dorset with a property that feels like a true Vermont retreat. This lovingly maintained offering pairs a welcoming main residence with a separate one-bedroom cottage, 4.5 acres of open land, a private pond, and beautiful views creating a rare opportunity to enjoy space, privacy, and flexibility in one memorable setting. The main home welcomes you with a light-filled sunroom, a wonderful place to relax and enjoy the surrounding scenery. The renovated eat in kitchen with a fireplace features beautiful, leathered granite countertops, stainless steel appliances while the spa

$949,000

3 beds3 baths1,823 sq ft

40 Kelleher Rd, Dorset, VT 05251

Light filled sunroom • Guest cottage • Private pond

Property at 1376 Shaftsbury Hollow Rd, Shaftsbury, VT 05262, 2 beds, 1 bath

$469,000

2 beds1 bath1,144 sq ft

1376 Shaftsbury Hollow Rd, Shaftsbury, VT 05262

Property at 262 Timber Trail Rd, Shaftsbury, VT 05262, 3 beds, 3 baths

$685,000

3 beds3 baths3,153 sq ft

262 Timber Trail Rd, Shaftsbury, VT 05262

Property at 735 Granger Hollow Rd, North Bennington, VT 05257, 3 beds, 2.5 baths

$399,900

3 beds2.5 baths1,920 sq ft

735 Granger Hollow Rd, North Bennington, VT 05257

Property at 686 Route 30, Dorset, VT 05261, 4 beds, 3 baths

$369,000

4 beds3 baths2,000 sq ft

686 Route 30, Dorset, VT 05261

Property at 301 Beech St, Bennington, VT 05201, 2 beds, 1 bath

$189,900

2 beds1 bath462 sq ft

301 Beech St, Bennington, VT 05201

Property at 12 Hurley Ln, Bennington, VT 05201, 3 beds, 1 bath

$199,900

3 beds1 bath1,132 sq ft

12 Hurley Ln, Bennington, VT 05201

Property at 2 Bromley Ln, North Bennington, VT 05257, 4 beds, 1.5 baths

$395,000

4 beds1.5 baths1,816 sq ft

2 Bromley Ln, North Bennington, VT 05257

Property at 33 Burnt Hill Rd, Winhall, VT 05340, 3 beds, 2 baths

$599,000

3 beds2 baths1,890 sq ft

33 Burnt Hill Rd, Winhall, VT 05340

Property at 1474 Dorset West Rd, Dorset, VT 05251, 3 beds, 3 baths

$1,375,000

3 beds3 baths2,457 sq ft

1474 Dorset West Rd, Dorset, VT 05251

Property at 1141 Burgess Rd, Bennington, VT 05201, 2 beds, 1.5 baths

$345,000

2 beds1.5 baths1,750 sq ft

1141 Burgess Rd, Bennington, VT 05201

Property at 845 Bailey Hill Rd, Readsboro, VT 05350, 1 bed

$74,500

1 bed— baths586 sq ft

845 Bailey Hill Rd, Readsboro, VT 05350

Property at 4910 Vaughn Farm Rd #10, Manchester, VT 05255, 4 beds, 3.5 baths

$499,000

4 beds3.5 baths2,345 sq ft

4910 Vaughn Farm Rd #10, Manchester, VT 05255

Property at 171 Garbrooke Dr, Bennington, VT 05201, 3 beds, 2 baths

$325,000

3 beds2 baths1,688 sq ft

171 Garbrooke Dr, Bennington, VT 05201

Property at 219-221 Washington Ave, Bennington, VT 05201, 6 beds, 2 baths

$349,900

6 beds2 baths2,584 sq ft

219-221 Washington Ave, Bennington, VT 05201

Property at 134 Grapevine Ln, Pownal, VT 05261, 4 beds, 3.5 baths

$999,000

4 beds3.5 baths7,102 sq ft

134 Grapevine Ln, Pownal, VT 05261

Property at 128 Bear Mountain Camp Rd, West Rupert, VT 05776, 2 beds, 1 bath

$140,000

2 beds1 bath— sq ft

128 Bear Mountain Camp Rd, West Rupert, VT 05776

Property at 2529 Main St, Manchester, VT 05254, 5 beds, 2 baths

$995,000

5 beds2 baths3,522 sq ft

2529 Main St, Manchester, VT 05254

Property at 440 Marcia Ln, Dorset, VT 05251, 5 beds, 6.5 baths

$4,995,000

5 beds6.5 baths7,455 sq ft

440 Marcia Ln, Dorset, VT 05251

Property at 33 Stone Lodge Rd, Winhall, VT 05340, 4 beds, 3.5 baths

$2,399,000

4 beds3.5 baths4,536 sq ft

33 Stone Lodge Rd, Winhall, VT 05340

Property at 23 Loop Rd #10, Bondville, VT 05340, 3 beds, 2 baths

$595,000

3 beds2 baths1,416 sq ft

23 Loop Rd #10, Bondville, VT 05340

Property at 3542 North Rd, Sunderland, VT 05250, 3 beds, 2 baths

$989,000

3 beds2 baths1,680 sq ft

3542 North Rd, Sunderland, VT 05250

Property at 130 Morgan St, Bennington, VT 05201, 3 beds, 2 baths

$179,000

3 beds2 baths1,600 sq ft

130 Morgan St, Bennington, VT 05201

Property at 19 Winhall Condo Rd #4, Winhall, VT 05340, 2 beds, 2 baths

$345,000

2 beds2 baths960 sq ft

19 Winhall Condo Rd #4, Winhall, VT 05340

Property at 1180 North Rd, East Arlington, VT 05250, 4 beds, 2.5 baths

$489,000

4 beds2.5 baths2,240 sq ft

1180 North Rd, East Arlington, VT 05250

Property at 493 Main Rd, Stamford, VT 05352, 5 beds, 1 bath

$159,900

5 beds1 bath1,534 sq ft

493 Main Rd, Stamford, VT 05352

Property at 16B Bromley Knolls Rd Unit B, Winhall, VT 05340, 3 beds, 2 baths

$399,000

3 beds2 baths1,225 sq ft

16B Bromley Knolls Rd Unit B, Winhall, VT 05340

Property at 1944 Monument Ave, Bennington, VT 05201, 3 beds, 2.5 baths

$1,695,000

3 beds2.5 baths4,120 sq ft

1944 Monument Ave, Bennington, VT 05201

Property at 928 Main Rd, Stamford, VT 05253, 4 beds, 2 baths

$449,000

4 beds2 baths3,096 sq ft

928 Main Rd, Stamford, VT 05253

Property at 0 Stratton Gardens Rd Unit 10a, 10b,, Winhall, VT 05340

$240,000

Land10.06 acres (lot)

0 Stratton Gardens Rd Unit 10a, 10b,, Winhall, VT 05340

Property at 0 W Mountain Rd, Shaftsbury, VT 05262

$85,000

Land2.80 acres (lot)

0 W Mountain Rd, Shaftsbury, VT 05262

Property at N Pownal Rd Unit 002 232, Pownal, VT 05261

$695,000

Land117.00 acres (lot)

N Pownal Rd Unit 002 232, Pownal, VT 05261

Property at 0 Sylvan Ridge Rd Lot 25, Winhall, VT 05340

$108,000

Land1.00 acre (lot)

0 Sylvan Ridge Rd Lot 25, Winhall, VT 05340

Property at 0 Fox Ln Lot 3, Dorset, VT 05251

$245,000

Land3.00 acres (lot)

0 Fox Ln Lot 3, Dorset, VT 05251

Property at 01 Old Depot Rd, Arlington, VT 05250

$239,000

Land5.35 acres (lot)

01 Old Depot Rd, Arlington, VT 05250

Property at 0 Bergrucken Ln Unit 6-377, Stamford, VT 05352

$20,000

Land1.20 acres (lot)

0 Bergrucken Ln Unit 6-377, Stamford, VT 05352

Property at 3149 W Hill Dr, Readsboro, VT 05350, 2 beds, 1 bath

$325,000

2 beds1 bath976 sq ft

3149 W Hill Dr, Readsboro, VT 05350

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New Listings for Sale in Bennington County

There are currently 41 new listings for sale in Bennington County at a median listing price of $527K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Bennington County stay on the market for 74 days. This map is refreshed with the newest listings in Bennington County every 15 minutes.

In the past month, 47 homes have been sold in Bennington County. In addition to houses in Bennington County, there were also 39 condos, 0 townhouses, and 17 multi-family units for sale in Bennington County last month. Find your dream home in Bennington County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Bennington County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Bennington County. If you're looking to sell your home in the Bennington County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Bennington County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Copyright 2026 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Sat Aug 29 2026 on the search page

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