Bennington County, VT homes for sale & real estate

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ABOUT THIS HOME
Bennington County, VT Homes for Sale
This Charming country home is currently being used as a primary home with a vacant 2nd in-law rental home. This property could be either a single family residence with/without an in-law house or as a 2 unit multifamily with 2 separate houses, This quiet country location has 2 homes located on its 2 acres. The main home is a 3 bedroom ranch featuring a large eat-in kitchen opening into a large living room. 3 bedrooms, including an addition with a large primary with 2 closets inlcuding one whick is a large walk-in closet. A large full bath with washer/dryer hookups completes the living area. The house has a partial concrete basement under the older portion, with a crawlspace under the additio

$269,900

3 beds1 bath1,392 sq ft

196 Granger Hollow Rd, North Bennington, VT 05257

Large primary • Large eat-in kitchen • Large living room

FLOOR PLAN

ABOUT THIS HOME
Bennington County, VT Homes for Sale
Welcome to your next chapter in the charming heart of Vermont, where easy living meets thoughtful design in this beautifully crafted one-level duplex townhouse. If you've been dreaming of a home that eliminates stairs from your daily routine while still delivering style and substance, your search ends here. Step inside and discover an open floor plan that feels both spacious and inviting across 1,786 square feet of well-appointed living space. The kitchen is a true showstopper, featuring custom cabinetry and stunning wood countertops that bring warmth and character to every meal. A generous breakfast bar provides the perfect spot for morning coffee or casual entertaining with friends. Three

$575,000

3 beds2.5 baths1,786 sq ft

14 A Marisa Ln, Dorset, VT 05251

Custom cabinetry • Open floor plan • Wood countertops

ABOUT THIS HOME
Bennington County, VT Homes for Sale
'MOONLIGHT REFLECTIONS ON AN UPPER HOLLOW SANCTUARY'. .. This stunning rare estate sits on 66 secluded acres of unspoiled beauty, offering breathtaking sweeping views of two luminous ponds, where moonlight reflections shimmer across the water each evening, creating a truly magical feeling. Inside you will find a contemporary open layout anchored by a dramatic stone fireplace, perfect for cozy evenings. The main residence captures the landscape from every angle blending modern architecture seamlessly with nature. This is much more than a home, it is truly a legacy property. .. Prestigious, Private and Profoundly Peaceful and must be seen to be fully appreciated!! Beauty, solitude, quiet luxu

$5,600,000

5 beds5.5 baths4,674 sq ft

1060 Upper Hollow Rd, Dorset, VT 05251

Modern architecture • Two luminous ponds • 66 secluded acres

ABOUT THIS HOME
Bennington County, VT Homes for Sale
Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a large garage with an attached storage shed and ample paved parking.

$209,900

2 beds1 bath1,075 sq ft

1083 Main St, Bennington, VT 05201

Spacious kitchen • Versatile office • Main-level laundry

ABOUT THIS HOME
Bennington County, VT Homes for Sale
This is the ultimate modern Alpine chalet -- with the rare opportunity to also have a separate guest house on the property for income or guests! Both buildings are fully renovated, yet boast the classic detailing of mountain homes in the Alps. In the 4BR/3.5BA main house, three expansive floors offer sunny, well-appointed space for everyone. Head upstairs to join your friends and family in the open-concept European kitchen/living/dining room with expanded island optimal for entertaining -- grill and wraparound deck just outside the kitchen. The fourth bedroom -- a primary suite with en-suite bathroom -- is on this level. On the walk-out lower level, a game room with pool table and a separat

$949,000

4 beds3.5 baths5,248 sq ft

41-43 Cranberry Hill Rd, Winhall, VT 05340

Swimming pond • Sandy beach • Fully renovated

Property at 59 Garden Loop Rd, Winhall, VT 05340, 4 beds, 4.5 baths

$2,850,000

4 beds4.5 baths3,762 sq ft

59 Garden Loop Rd, Winhall, VT 05340

Property at E1 Rock Ridge Rd, Winhall, VT 05340, 4 beds, 3 baths

$899,000

4 beds3 baths3,252 sq ft

E1 Rock Ridge Rd, Winhall, VT 05340

Property at 205 County St, Bennington, VT 05201, 5 beds, 2 baths

$219,000

5 beds2 baths1,860 sq ft

205 County St, Bennington, VT 05201

Property at 142 Schenkar Rd, Pownal, VT 05261, 3 beds, 2.5 baths

$625,000

3 beds2.5 baths3,295 sq ft

142 Schenkar Rd, Pownal, VT 05261

Property at 551 W Fields Rd, Manchester, VT 05254, 6 beds, 8 baths

$10,300,000

6 beds8 baths10,993 sq ft

551 W Fields Rd, Manchester, VT 05254

Property at 99 Holly's Way, West Rupert, VT 05776, 3 beds, 2 baths

$975,000

3 beds2 baths2,403 sq ft

99 Holly's Way, West Rupert, VT 05776

Property at 6 Old Ridge Rd, Winhall, VT 05340, 5 beds, 4.5 baths

$1,100,000

5 beds4.5 baths4,453 sq ft

6 Old Ridge Rd, Winhall, VT 05340

Property at 21 Jameson Flts Unit Duplex Unit B, Manchester, VT 05255, 3 beds, 2.5 baths

$595,000

3 beds2.5 baths1,368 sq ft

21 Jameson Flts Unit Duplex Unit B, Manchester, VT 05255

Property at 233 Squires Rd, Manchester Center, VT 05255, 2 beds, 1 bath

$1,200,000

2 beds1 bath1,056 sq ft

233 Squires Rd, Manchester Center, VT 05255

Property at 924 Henderson Rd, Williamstown, MA 01267, 4 beds, 2 baths

$850,000

4 beds2 baths3,507 sq ft

924 Henderson Rd, Williamstown, MA 01267

Property at 7 Roundtree Rd, Winhall, VT 05340, 4 beds, 3.5 baths

$910,000

4 beds3.5 baths3,031 sq ft

7 Roundtree Rd, Winhall, VT 05340

Property at 14 Vaughn Farm Rd #1, Manchester Center, VT 05255, 3 beds, 2.5 baths

$495,000

3 beds2.5 baths1,848 sq ft

14 Vaughn Farm Rd #1, Manchester Center, VT 05255

Property at 3530 VT Route 346, Pownal, VT 05261, 3 beds, 2.5 baths

$249,900

3 beds2.5 baths1,810 sq ft

3530 VT Route 346, Pownal, VT 05261

Property at 773 Oberdorf Rd, Readsboro, VT 05350, 4 beds, 2 baths

$329,900

4 beds2 baths2,030 sq ft

773 Oberdorf Rd, Readsboro, VT 05350

Property at 1675 Route 9, Searsburg, VT 05363, 2 beds, 1 bath

$159,000

2 beds1 bath760 sq ft

1675 Route 9, Searsburg, VT 05363

Property at 1182 1184 East Manchester Rd, Manchester Center, VT 05255, 9 beds, 8.5 baths

$4,995,000

9 beds8.5 baths7,900 sq ft

1182 1184 East Manchester Rd, Manchester Center, VT 05255

Property at 340 Pleasant St, Bennington, VT 05201, 3 beds, 2 baths

$215,000

3 beds2 baths1,300 sq ft

340 Pleasant St, Bennington, VT 05201

Property at 935 Old Manchester Rd, Peru, VT 05152, 2 beds, 1 bath

$495,000

2 beds1 bath1,344 sq ft

935 Old Manchester Rd, Peru, VT 05152

Property at 393 Morse Hill Rd, East Dorset, VT 05253, 3 beds, 2 baths

$450,000

3 beds2 baths1,460 sq ft

393 Morse Hill Rd, East Dorset, VT 05253

Property at 121 High Meadow Rd, Winhall, VT 05340-9999, 6 beds, 4 baths

$1,399,999

6 beds4 baths3,800 sq ft

121 High Meadow Rd, Winhall, VT 05340-9999

Property at 751 Main Rd, Stamford, VT 05352, 6 beds, 5 baths

$1,900,000

6 beds5 baths5,704 sq ft

751 Main Rd, Stamford, VT 05352

Property at 262 Dwyers Camp Rd, Shaftsbury, VT 05262, 3 beds, 2 baths

$479,000

3 beds2 baths2,065 sq ft

262 Dwyers Camp Rd, Shaftsbury, VT 05262

Property at 4928 Main St #2, Manchester Center, VT 05255, 2 beds, 2 baths

$645,000

2 beds2 baths1,432 sq ft

4928 Main St #2, Manchester Center, VT 05255

Property at 60 Hilltop Rd #60, Winhall, VT 05340, 4 beds, 3 baths

$609,000

4 beds3 baths1,650 sq ft

60 Hilltop Rd #60, Winhall, VT 05340

Property at 120 Village St, East Dorset, VT 05253, 4 beds, 3.5 baths

$434,500

4 beds3.5 baths3,861 sq ft

120 Village St, East Dorset, VT 05253

Property at 288 Cedar Ln, Peru, VT 05152, 9 beds, 7 baths

$2,275,000

9 beds7 baths5,512 sq ft

288 Cedar Ln, Peru, VT 05152

Property at 32 Cassie Ln, Bennington, VT 05201, 2 beds, 2 baths

$96,406

2 beds2 baths777 sq ft

32 Cassie Ln, Bennington, VT 05201

Property at 3888-3904 VT Route 7A, Arlington, VT 05250, 17 beds, 19 baths

$1,495,000

17 beds19 baths14,861 sq ft

3888-3904 VT Route 7A, Arlington, VT 05250

Property at Ridge Rd Unit C-4, Bondville, VT 05340, 3 beds, 3 baths

$825,000

3 beds3 baths2,598 sq ft

Ridge Rd Unit C-4, Bondville, VT 05340

Property at The Maple Plan, Pownal, VT 05261, 3 beds, 2 baths

$95,999

3 beds2 baths1,001 sq ft

The Maple Plan, Pownal, VT 05261

Listing provided by Zillow

Property at 145 Oberdorf Rd, Readsboro, VT 05350, 4 beds, 2 baths

$490,642

4 beds2 baths1,708 sq ft

145 Oberdorf Rd, Readsboro, VT 05350

Property at 2167 Myers Rd, Shaftsbury, VT 05262, 3 beds, 3 baths

$1,795,000

3 beds3 baths5,228 sq ft

2167 Myers Rd, Shaftsbury, VT 05262

Property at 1629 N Mann Hill Rd, Pownal, VT 05261, 5 beds, 5.5 baths

$845,000

5 beds5.5 baths3,875 sq ft

1629 N Mann Hill Rd, Pownal, VT 05261

Property at 215 & 221 VT Route 30, Dorset, VT 05251, 6 beds, 3 baths

$1,200,000

6 beds3 baths3,340 sq ft

215 & 221 VT Route 30, Dorset, VT 05251

Property at 515 W Fields Rd, Manchester, VT 05254, 5 beds, 5.5 baths

$5,900,000

5 beds5.5 baths6,500 sq ft

515 W Fields Rd, Manchester, VT 05254

Property at 124 Elm St, Bennington, VT 05201

$950,000

— beds— baths8,888 sq ft

124 Elm St, Bennington, VT 05201

Viewing page 5 of 7

Average home prices near Bennington County, VT

Cities

Jamaica homes for sale
$470,000
Wilmington homes for sale
$444,500
Manchester homes for sale
$995,000
East Dorset homes for sale
$525,000
Stratton Mountain homes for sale
$912,500
Arlington homes for sale
$537,000
Bennington homes for sale
$249,000
Manchester Center homes for sale
$610,000
Chimney Hill homes for sale
$465,900
Dorset homes for sale
$1,155,000
South Shaftsbury homes for sale
$439,000
North Bennington homes for sale
$338,700

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)

$383,319

+10.3% YoY | Jun 2026

1 year
3 year
5 year

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

Location

Data

Jun 2026

Growth

% YoY

Bennington County, VT

$383,319

+10.3%

See more Bennington County, VT market insights

More to explore in Bennington County, VT

How to buy a house in Bennington County, VT

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Popular Markets in Vermont

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Shelburne homes for sale
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Waitsfield homes for sale
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Manchester homes for sale
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Middlebury homes for sale
$499,000
Bennington homes for sale
$249,450
Norwich homes for sale
$1,725,000

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 Wed Aug 26 2026 on the search page

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