Pending Listings in Bennington County, VT

73 homes

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ABOUT THIS HOME
Pending Listing in Bennington County, VT:
Nestled in the woods on a generous private lot, 44 Lake Road is a contemporary Vermont retreat offering peaceful seclusion with big-sky views of Stratton Mountain. Designed to blend with its natural surroundings, this home features warm wood accents, soaring ceilings, and walls of glass that bring the outdoors in. The open main living area is ideal for apres-ski gatherings, with a spacious great room, wood-burning fireplace, and sliders that open to an expansive deck overlooking the forest and mountain vistas. Multiple levels provide excellent separation of space with comfortable bedrooms, a lofted flex area, and bonus rooms perfect for guests, recreation, or work-from-home needs. Outside,

$450,000

5 beds3 baths2,303 sq ft

44 Lake Rd, Bondville, VT 05340

Private lot • Wood accents • Soaring ceilings

CONTINGENT

ABOUT THIS HOME
Pending Listing in Bennington County, VT:
Immerse Yourself in Vermont Charm: Contemporary Home in Strattonwald! Live the Stratton dream in this stunning 3-bedroom, 2-bathroom contemporary home nestled within the Strattonwald community at Stratton Resort, VT. This impeccably designed home offers the perfect blend of modern comfort and rustic charm, ideal for your next Vermont getaway. Unwind and reconnect with a spacious living area featuring a warm and inviting wood burning fireplace, perfect for cozy evenings after a day on the slopes. The open concept layout that flows seamlessly from the living area to the fully equipped kitchen is ideal for entertaining family and friends. The lower level den/office space with 2 futons provides

$485,000

3 beds2 baths2,298 sq ft

19 Deer Run Rd, Bondville, VT 05340

Lower level den • Mudroom with laundry • Open concept layout

CONTINGENT

ABOUT THIS HOME
Pending Listing in Bennington County, VT:
Bennington VT home for sale where daily life starts on the screened front porch and wraps on the rear deck. This Cape style single family home offers 3 bedrooms, 1 bath, and 854 sq ft on one level, set on a 0.15 acre lot in town Bennington close to schools, shops, and services. Fresh white paint brightens a cozy living room with a large front window. Original hardwood floors add character and are ready for a new finish. The expanded kitchen and dining area keeps weeknights simple with older wood cabinets, white tile backsplash, included range and refrigerator, and stacked washer and dryer for true main floor convenience. Three compact bedrooms provide natural light and flexible use for slee

$170,000

3 beds1 bath854 sq ft

136 McKinley St, Bennington, VT 05201

Screened front porch • Dining area • Expanded kitchen

CONTINGENT

ABOUT THIS HOME
Pending Listing in Bennington County, VT:
This single-family home offers 1,248 sq ft of living space on a 0.26-acre lot. Featuring 3 bedrooms and 1 full bathroom, this property provides an inviting layout ideal for everyday living. Has enclosed back porch. A standout feature is the detached 1-car garage, complete with additional space for a workshop—perfect for hobbyists, storage, or small-scale projects.

$199,900

3 beds1 bath1,248 sq ft

111 Hicks Ave, Bennington, VT 05201

Enclosed back porch • Detached garage • 0.26 acre lot

CONTINGENT

ABOUT THIS HOME
Pending Listing in Bennington County, VT:
PRICE ADJUSTMENT: On a gentle rise surrounded by 7.5 acres of meadows and woodland, this Vermont style ranch subtly blends an appealing rustic charm with contemporary features. The current owners purchased the property in 2021 for family and friends and installed a new wastewater system, new furnace, new roof section, new appliances. The rough sawn clapboard exterior delineates the enduring character of the house. A fieldstone walkway introduces the central foyer with access to two wings. The focus of one is the living dining gathering area with the warmth of traditional wood paneled walls, pine flooring throughout, a stone fireplace and hearth, views from a window seat, bar entertainment n

$485,000

4 beds3 baths2,073 sq ft

2588 Vermont Route 11, Peru, VT 05152

New furnace • New appliances • Fieldstone walkway

Property at 58 Granite Cir Unit 1, Manchester, VT 05255, 2 beds, 1 bath

$299,900

2 beds1 bath996 sq ft

58 Granite Cir Unit 1, Manchester, VT 05255

Property at 150 Fillmore St, Bennington, VT 05201, 3 beds, 2 baths

$275,000

3 beds2 baths1,404 sq ft

150 Fillmore St, Bennington, VT 05201

Property at 143 Nichols Rd, Peru, VT 05152, 8 beds, 6 baths

$895,000

8 beds6 baths4,326 sq ft

143 Nichols Rd, Peru, VT 05152

Property at 14 Stone House Rd, Bondville, VT 05340, 3 beds, 4.5 baths

$1,725,000

3 beds4.5 baths4,312 sq ft

14 Stone House Rd, Bondville, VT 05340

Property at 6 Chad Cir, Bondville, VT 05340, 5 beds, 4 baths

$1,100,000

5 beds4 baths4,788 sq ft

6 Chad Cir, Bondville, VT 05340

Property at 851 Middle Pownal Rd, Pownal, VT 05261, 3 beds, 2 baths

$349,500

3 beds2 baths1,721 sq ft

851 Middle Pownal Rd, Pownal, VT 05261

Property at 2460 East Rd, Shaftsbury, VT 05262, 3 beds, 1.5 baths

$239,000

3 beds1.5 baths1,120 sq ft

2460 East Rd, Shaftsbury, VT 05262

Property at 755 Main St, Bennington, VT 05201, 3 beds, 1.5 baths

$145,000

3 beds1.5 baths1,485 sq ft

755 Main St, Bennington, VT 05201

Property at 927 Water St, North Bennington, VT 05257, 5 beds, 4 baths

$374,900

5 beds4 baths3,400 sq ft

927 Water St, North Bennington, VT 05257

Property at 231 Bergrucken Ln Unit 121-122, Readsboro, VT 05350, 3 beds, 1 bath

$360,000

3 beds1 bath1,432 sq ft

231 Bergrucken Ln Unit 121-122, Readsboro, VT 05350

Property at 19 Winhall Condo Rd #5, Winhall, VT 05340, 2 beds, 2 baths

$325,000

2 beds2 baths960 sq ft

19 Winhall Condo Rd #5, Winhall, VT 05340

Property at 308 Mending Walls Rd, Manchester Center, VT 05255, 4 beds, 3.5 baths

$775,000

4 beds3.5 baths4,508 sq ft

308 Mending Walls Rd, Manchester Center, VT 05255

Property at 318 Spring Hill Ln, Dorset, VT 05251, 7 beds, 10 baths

$4,500,000

7 beds10 baths7,422 sq ft

318 Spring Hill Ln, Dorset, VT 05251

Property at 1016 County St, Bennington, VT 05201, 2 beds, 1 bath

$249,000

2 beds1 bath900 sq ft

1016 County St, Bennington, VT 05201

Property at 55 Monument Ave, Bennington, VT 05201, 3 beds, 2.5 baths

$650,000

3 beds2.5 baths2,675 sq ft

55 Monument Ave, Bennington, VT 05201

Property at 14 Vaughn Farm Rd #4, Manchester Center, VT 05255, 3 beds, 3.5 baths

$534,900

3 beds3.5 baths1,888 sq ft

14 Vaughn Farm Rd #4, Manchester Center, VT 05255

Property at 46-48 Lower Taylor Hill Rd, Winhall, VT 05340, 2 beds, 2 baths

$420,000

2 beds2 baths1,798 sq ft

46-48 Lower Taylor Hill Rd, Winhall, VT 05340

Property at 653 Roaring Branch Rd, Arlington, VT 05250, 2 beds, 1.5 baths

$365,000

2 beds1.5 baths1,127 sq ft

653 Roaring Branch Rd, Arlington, VT 05250

Property at 61 Autumn Acres Rd, Bennington, VT 05201, 3 beds, 1 bath

$275,000

3 beds1 bath1,169 sq ft

61 Autumn Acres Rd, Bennington, VT 05201

Property at 694 Sykes Hollow Rd, Pawlet, VT 05776, 3 beds, 2.5 baths

$1,275,000

3 beds2.5 baths2,259 sq ft

694 Sykes Hollow Rd, Pawlet, VT 05776

Property at 1059 Bailey Hill Rd, Readsboro, VT 05350, 3 beds, 1 bath

$502,900

3 beds1 bath2,400 sq ft

1059 Bailey Hill Rd, Readsboro, VT 05350

Property at 2591 Chapel Rd, Bennington, VT 05201, 2 beds, 1 bath

$185,000

2 beds1 bath880 sq ft

2591 Chapel Rd, Bennington, VT 05201

Property at 693 Longview Dr, Manchester, VT 05254, 4 beds, 4 baths

$1,269,000

4 beds4 baths4,266 sq ft

693 Longview Dr, Manchester, VT 05254

Property at 92 Coventry Ln, Manchester Center, VT 05255, 4 beds, 2.5 baths

$985,000

4 beds2.5 baths3,215 sq ft

92 Coventry Ln, Manchester Center, VT 05255

Property at 3343 Main St, Manchester, VT 05254, 4 beds, 3 baths

$915,000

4 beds3 baths2,898 sq ft

3343 Main St, Manchester, VT 05254

Property at Ridge Ct Unit A6, Bondville, VT 05340, 4 beds, 3 baths

$719,000

4 beds3 baths2,118 sq ft

Ridge Ct Unit A6, Bondville, VT 05340

Property at 883 VT Route 7A, Shaftsbury, VT 05262, 4 beds, 4 baths

$199,000

4 beds4 baths3,576 sq ft

883 VT Route 7A, Shaftsbury, VT 05262

Property at 26-30 Sage St, North Bennington, VT 05257, 9 beds, 3 baths

$279,000

9 beds3 baths3,176 sq ft

26-30 Sage St, North Bennington, VT 05257

Property at 6828 Main St, Readsboro, VT 05350, 0.5 baths

$369,900

0 beds0.5 baths4,220 sq ft

6828 Main St, Readsboro, VT 05350

Property at 389 Wilcox Rd, Arlington, VT 05250, 3 beds, 2 baths

$595,000

3 beds2 baths3,475 sq ft

389 Wilcox Rd, Arlington, VT 05250

Property at 103 Norton St, Bennington, VT 05201, 4 beds, 2 baths

$339,000

4 beds2 baths1,728 sq ft

103 Norton St, Bennington, VT 05201

Property at 64 Ethans Way, Bennington, VT 05201, 2 beds, 1 bath

$89,499

2 beds1 bath746 sq ft

64 Ethans Way, Bennington, VT 05201

Property at 2288 East Rd, Bennington, VT 05201, 5 beds, 3 baths

$279,900

5 beds3 baths3,164 sq ft

2288 East Rd, Bennington, VT 05201

Property at 00 Alpendorf Ave #88, Readsboro, VT 05350

$17,000

— beds— baths— sq ft

00 Alpendorf Ave #88, Readsboro, VT 05350

Property at 00 Bergrucken Ln Unit 119-120, Readsboro, VT 05350

$27,000

— beds— baths— sq ft

00 Bergrucken Ln Unit 119-120, Readsboro, VT 05350

Property at 100 Back Nine Blf, Manchester, VT 05254

$360,000

— beds— baths— sq ft

100 Back Nine Blf, Manchester, VT 05254

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Pending Listings in Bennington County

There are currently 73 pending listings for sale in Bennington County at a median listing price of $550K. 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 86 days. This map is refreshed with the newest listings in Bennington County every 15 minutes.

In the past month, 38 homes have been sold in Bennington County. In addition to houses in Bennington County, there were also 30 condos, 1 townhouse, and 11 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 2025 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 Fri Dec 12 2025 on the search page

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