Bennington County, VT homes for sale & real estate

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50 Stratton View Rd, Winhall, VT 05340
50 Stratton View Rd, Winhall, VT 05340
50 Stratton View Rd, Winhall, VT 05340
ABOUT THIS HOME
Bennington County, VT Homes for Sale
Custom built six-bedroom home on 2 acres with spectacular views of Stratton Mountain. The kitchen has granite countertops and custom cabinets with the dining area nearby with plenty of space to accommodate a large gathering. The living area has a cathedral ceiling with large windows for an abundance of natural light and stunning year-round views of Stratton Mountain, with a lovely stone fireplace for those colder Vermont days. The main floor also boasts a sunroom with reading loft and a wet bar for après ski or warm summer nights. There are two en-suite bedrooms, each with stunning custom bath and a hot tub, sauna, fireplace, den area, and bunk room. An additional room for an at home

$1,100,000

6 beds5 baths5,298 sq ft

50 Stratton View Rd, Winhall, VT 05340

1.98 acre lot • 3 garage spots

4 Pine Rd, Bennington, VT 05201
4 Pine Rd, Bennington, VT 05201
4 Pine Rd, Bennington, VT 05201
ABOUT THIS HOME
Bennington County, VT Homes for Sale
Motivated seller of this beautifully ranch home on a dead-end road boasts 4 Bedroom. Enjoy the warmth of the sunroom during the day. The living room centered in the middle of the house has plenty of space to spread out and enjoy the pellet stove insert with a brick hearth on those cool nights. Locally crafted Cushman Style cabinet in the dining area with delightful wood cabinets in the kitchen. Enjoy the views of Mount Anthony from the concrete stamped patio for outdoor dining and relaxing. The corner lot is located on a dead-end street, This home is located within walking distance to the hospital, the Bennington Area Trail System, Close to public transportation, Downtown shopping. Southwes

$269,000

4 beds1 bath1,875 sq ft

4 Pine Rd, Bennington, VT 05201

0.34 acre lot • 2 garage spots

759 Stratton Mountain Access Rd #339, Stratton, VT 05155
759 Stratton Mountain Access Rd #339, Stratton, VT 05155
759 Stratton Mountain Access Rd #339, Stratton, VT 05155
ABOUT THIS HOME
Bennington County, VT Homes for Sale
Designed with the mountain enthusiast in mind, and located just a short walk from the Stratton Resort Village and ski slopes, this three bedroom three bath condominium offers quality and convenience. Private parking, pool, hot tub, sauna and shuttle to the slopes.

$1,100,000

3 beds3 baths1,501 sq ft

759 Stratton Mountain Access Rd #339, Stratton, VT 05155

$1,160 HOA • 2 garage spots • Community pool

224 Sycamore Ln, Shaftsbury, VT 05252
224 Sycamore Ln, Shaftsbury, VT 05252
224 Sycamore Ln, Shaftsbury, VT 05252
ABOUT THIS HOME
Bennington County, VT Homes for Sale
This 4 bedroom cape is located on a dead end street in a desirable neighborhood within the village of Shaftsbury. The updated kitchen has a small island and is open to the dining area. The living room has hardwood floors, gas fire place and built-ins along one wall. There is a washer and dryer located on the first floor in the entry hall and a full bath also on this level. There are two bedrooms on the first floor, one of which could be used as an office or den space. One bedroom on the second floor has built in dresser and both bedrooms have access to under eave storage. There is also a 3/4 bath on the second floor. The yard is fenced in and not only level lot but has raised beds for g

$299,000

4 beds2 baths1,602 sq ft

224 Sycamore Ln, Shaftsbury, VT 05252

0.37 acre lot • Garage

376 Windward Hl, Dorset, VT 05251
376 Windward Hl, Dorset, VT 05251
376 Windward Hl, Dorset, VT 05251
ABOUT THIS HOME
Bennington County, VT Homes for Sale
Welcome to 376 Windward Hill, a stunning Southern Vermont estate with breathtaking views of the Taconic and Green Mountain Ranges. Spanning 12 acres, the property features a private trout pond and tranquil waterfall, creating a serene atmosphere. Inside, the home combines timeless elegance with modern comfort. Herringbone brick and hardwood floors lead to the expansive living room, highlighted by a two-story stone fireplace. This grand space flows seamlessly into the formal dining area, which opens to a screened porch and wrap-around deck, perfect for enjoying mountain vistas. The gourmet kitchen boasts a cozy bar, ample cabinetry, a butler's pantry, and top-of-the-line appliances. The prim

$2,375,000

4 beds4.5 baths5,696 sq ft

376 Windward Hl, Dorset, VT 05251

12.67 acre lot • 3 garage spots

Property at 218 Union St, Bennington, VT 05201, 5 beds, 2 baths

$297,500

5 beds2 baths2,294 sq ft

218 Union St, Bennington, VT 05201

Property at 761 Stratton Mountain Access Rd #231, Stratton, VT 05155, 1 bed, 1 bath

$425,000

1 bed1 bath580 sq ft

761 Stratton Mountain Access Rd #231, Stratton, VT 05155

Property at 3 Stratton Ridge Rd, Winhall, VT 05340, 4 beds, 3 baths

$677,000

4 beds3 baths2,560 sq ft

3 Stratton Ridge Rd, Winhall, VT 05340

Property at 423-425 Main St, Bennington, VT 05201, 6 beds, 4 baths

$575,000

6 beds4 baths15,179 sq ft

423-425 Main St, Bennington, VT 05201

Property at 89 Field Way, Pownal, VT 05261, 2 beds, 1.5 baths

$329,000

2 beds1.5 baths1,152 sq ft

89 Field Way, Pownal, VT 05261

Property at 1677 Barnumville Rd, Manchester, VT 05255, 4 beds, 2.5 baths

$1,475,000

4 beds2.5 baths4,634 sq ft

1677 Barnumville Rd, Manchester, VT 05255

Property at 40 Jameson Flts Unit D, Manchester, VT 05255, 3 beds, 2.5 baths

$849,000

3 beds2.5 baths1,980 sq ft

40 Jameson Flts Unit D, Manchester, VT 05255

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

$225,000

3 beds2 baths1,416 sq ft

130 Beech St, Bennington, VT 05201

Property at 32-34 Sage St, Bennington, VT 05257, 5 beds, 2 baths

$225,000

5 beds2 baths1,478 sq ft

32-34 Sage St, Bennington, VT 05257

Property at 5 Stratton Ridge Rd, Winhall, VT 05340, 4 beds, 3 baths

$774,999

4 beds3 baths3,676 sq ft

5 Stratton Ridge Rd, Winhall, VT 05340

Property at 722 Main St, Bennington, VT 05201, 9 beds, 8.5 baths

$675,000

9 beds8.5 baths4,995 sq ft

722 Main St, Bennington, VT 05201

Property at 384 Riverbend Dr, Manchester, VT 05254, 4 beds, 7.5 baths

$2,750,000

4 beds7.5 baths8,586 sq ft

384 Riverbend Dr, Manchester, VT 05254

Property at 1424 West Rd, Manchester, VT 05255, 2 beds, 2.5 baths

$1,650,000

2 beds2.5 baths1,799 sq ft

1424 West Rd, Manchester, VT 05255

Property at 85 E Birch Rd #21, Stratton, VT 05155, 2 beds, 2 baths

$369,000

2 beds2 baths1,150 sq ft

85 E Birch Rd #21, Stratton, VT 05155

Property at 11 Pond View Rd, Winhall, VT 05340, 3 beds, 3 baths

$629,000

3 beds3 baths1,650 sq ft

11 Pond View Rd, Winhall, VT 05340

Property at 872 Barber Pond Rd, Pownal, VT 05261, 3 beds, 3.5 baths

$305,000

3 beds3.5 baths3,023 sq ft

872 Barber Pond Rd, Pownal, VT 05261

Property at 43 Middle Ridge Rd #311, Stratton, VT 05155, 2 beds, 2 baths

$665,000

2 beds2 baths1,036 sq ft

43 Middle Ridge Rd #311, Stratton, VT 05155

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

$799,000

3 beds3 baths2,118 sq ft

Ridge Ct Unit A6, Winhall, VT 05340

Property at 73 Cranberry Hill Rd, Winhall, VT 05340, 4 beds, 4.5 baths

$975,000

4 beds4.5 baths2,658 sq ft

73 Cranberry Hill Rd, Winhall, VT 05340

Property at 2 Lower Stratton Valley Rd, Winhall, VT 05340, 4 beds, 1.5 baths

$425,000

4 beds1.5 baths1,344 sq ft

2 Lower Stratton Valley Rd, Winhall, VT 05340

Property at Cobble Ridge Rd Unit D11, Winhall, VT 05340, 4 beds, 3.5 baths

$1,095,000

4 beds3.5 baths3,134 sq ft

Cobble Ridge Rd Unit D11, Winhall, VT 05340

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 72 Ethans Way, Bennington, VT 05201, 2 beds, 2 baths

$98,999

2 beds2 baths825 sq ft

72 Ethans Way, Bennington, VT 05201

Property at 92 Ethans Way, Bennington, VT 05201, 2 beds, 2 baths

$89,499

2 beds2 baths746 sq ft

92 Ethans Way, Bennington, VT 05201

Property at 86 Ethans Way Lot 86E, Bennington, VT 05201, 2 beds, 2 baths

$98,999

2 beds2 baths825 sq ft

86 Ethans Way Lot 86E, Bennington, VT 05201

Property at 19 Old Town Rd, Winhall, VT 05340, 5 beds, 6 baths

$2,500,000

5 beds6 baths7,625 sq ft

19 Old Town Rd, Winhall, VT 05340

Property at 405 VT Route 30, Winhall, VT 05340, 8 beds, 3.5 baths

$649,000

8 beds3.5 baths2,520 sq ft

405 VT Route 30, Winhall, VT 05340

Property at 338 Main St, Bennington, VT 05201, 4 beds, 3.5 baths

$750,000

4 beds3.5 baths6,650 sq ft

338 Main St, Bennington, VT 05201

Property at 41 / 43 Cranberry Hill Rd, Winhall, VT 05340, 4 beds, 3.5 baths

$1,150,000

4 beds3.5 baths4,478 sq ft

41 / 43 Cranberry Hill Rd, Winhall, VT 05340

Property at 708 Prospect St, Manchester, VT 05254, 5 beds, 5 baths

$1,195,000

5 beds5 baths4,321 sq ft

708 Prospect St, Manchester, VT 05254

Property at 38 Jamesons Flts, Manchester, VT 05255, 3 beds, 2.5 baths

$795,000

3 beds2.5 baths1,760 sq ft

38 Jamesons Flts, Manchester, VT 05255

Property at 162 Highland Ave, Manchester, VT 05255, 5 beds, 3 baths

$679,000

5 beds3 baths3,836 sq ft

162 Highland Ave, Manchester, VT 05255

Property at 339 S Stream Rd, Pownal, VT 05261, 5 beds, 2 baths

$55,000

5 beds2 baths2,204 sq ft

339 S Stream Rd, Pownal, VT 05261

Property at 25 Mountain Haunts Rd, Winhall, VT 05340, 6 beds, 6.5 baths

$2,999,000

6 beds6.5 baths6,650 sq ft

25 Mountain Haunts Rd, Winhall, VT 05340

Property at 527 South St, Bennington, VT 05201, 3 beds, 1.5 baths

$235,000

3 beds1.5 baths912 sq ft

527 South St, Bennington, VT 05201

Property at 263 Elm St, Shaftsbury, VT 05262, 4 beds, 2 baths

$439,000

4 beds2 baths2,368 sq ft

263 Elm St, Shaftsbury, VT 05262

Viewing page 2 of 5

Average home prices near Bennington County, VT

Cities

Wilmington homes for sale
Manchester homes for sale
$1,322,500
Stratton Mountain homes for sale
$995,000
Arlington homes for sale
$599,000
Bennington homes for sale
$269,900
Manchester Center homes for sale
$550,000
Chimney Hill homes for sale
$559,000
Dorset homes for sale
$1,582,500
North Bennington homes for sale
$225,000

Counties

Bennington County, VT real estate trends

All Home Types trends in Bennington County, VT

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$429,000

-10.6% YoY | Apr 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Apr 2025

Growth

% YoY

Bennington County, VT

$429,000

-10.6%

See more Bennington County, VT market insights

More to explore in Bennington County, VT

How to buy a house in Bennington County, VT

How much house can I afford?

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First-time homebuyer's guide

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Popular Markets in Vermont

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$1,322,500
Rutland homes for sale
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Ludlow homes for sale
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Bennington homes for sale
$269,900
Middlebury homes for sale
$695,000
Barre homes for sale
$259,950
Wilmington homes for sale
$0

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 Wed May 21 2025 on the search page

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