Bennington County, VT Homes

/31
Est $514,213 Not Listed For Sale

109 Hillcrest Rd, Manchester Center, VT 05255
- 2 Beds
- 1 Bath
- 960 Sq Ft
- Built 1969
109 Hillcrest Rd, Manchester Center, VT 05255

Last Sold Summary
- 7% Above List Price
- $500/SF
- 10 Days On Market
Last Sold Price $480,000

Last Listing Agent David Halligan Four Seasons Sotheby's Int'l Realty

/29
$729,000 Under Contract
- 3 Beds
- 3.5 Baths
- 2,262 Sq Ft
253 Owls Head Hill Ln S, Dorset, VT 05251

Welcome to this beautifully maintained Cape-style home tucked away on peaceful cul-de-sac with stunning mountain views. Enjoy your morning coffee on the front porch and relaxing evenings on the spacious back deck. Inside, you will find a warm and inviting layout featuring a gorgeous newer kitchen with modern finishes and ample space for cooking, gathering, and entertaining. The thoughtful floor

Annette Gallo Real Broker LLC

253 Owls Head Hill Ln S, Dorset, VT 05251
/53
$775,000 Sold Aug 13, 2025

E12 Rock Ridge Rd, Winhall, VT 05155
- 3 Beds
- 3 Baths
- 1,842 Sq Ft
- Built 1986
Last Sold Summary
- 3% Below List Price
- $421/SF
- 7 Days On Market
Last Listing Agent Cheyanne Pugliese

E12 Rock Ridge Rd, Winhall, VT 05155

/35
Est $688,149 Not Listed For Sale

602 Barnumville Rd, Manchester Center, VT 05255
- 3 Beds
- 2 Baths
- 1,907 Sq Ft
- Built 1960
602 Barnumville Rd, Manchester Center, VT 05255

Last Sold Summary
- 6% Above List Price
- $341/SF
- 5 Days On Market
Last Sold Price $650,000

Last Listing Agent Katherine Zilkha Four Seasons Sotheby's Int'l Realty

/39
$599,000 Under Contract
- 5 Beds
- 3.5 Baths
- 2,468 Sq Ft
17 Signal Hill Rd, Winhall, VT 05340

17 Signal Hill Road offers Vermont charm in a secluded mountain setting. With over 2,400 square feet of living space, this five-bedroom, three-and-a-half-bath home has been thoughtfully maintained and move-in ready. The main level features a spacious living room with a dramatic fieldstone fireplace, vaulted ceilings, and skylights that fill the home with natural light. A loft overlooking the

Christiane Carroccio TPW Real Estate

17 Signal Hill Rd, Winhall, VT 05340
/49
$1,865,000 Sold Dec 08, 2025

380 Partridge Hill Unit 22, Manchester, VT 05254
- 3 Beds
- 4.5 Baths
- 3,874 Sq Ft
- Built 2008
Last Sold Summary
- 1% Below List Price
- $481/SF
- 5 Days On Market
Last Listing Agent Christiane Carroccio TPW Real Estate

380 Partridge Hill Unit 22, Manchester, VT 05254

/31
Est $554,114 Not Listed For Sale

373 Highland Ave, Manchester Center, VT 05255
- 4 Beds
- 1.5 Baths
- 1,830 Sq Ft
- Built 1905
373 Highland Ave, Manchester Center, VT 05255

Last Sold Summary
- 6% Above List Price
- $287/SF
- 5 Days On Market
Last Sold Price $525,000

Last Listing Agent Tatsiana Clark Four Seasons Sotheby's Int'l Realty

/30
$550,000
- 2 Beds
- 2 Baths
- 2,218 Sq Ft
1439 Main St, Manchester Center, VT 05255

Purdy School House, est. 1850 - Step into history with this lovingly preserved former schoolhouse, offering timeless character with modern comfort. Featuring 2 bedrooms, 2 baths, and a striking stone fireplace, this home blends warmth and charm. A full basement and attached one-car garage provide practical convenience. Set on 2.01 acres, the property includes a fenced dog yard and plenty of space

Richard Slocum Four Seasons Sotheby's Int'l Realty

1439 Main St, Manchester Center, VT 05255
/43
$180,367 Sold Nov 06, 2025

634 Wiley Mountain Dr, Readsboro, VT 05350
- 1 Bed
- 400 Sq Ft
- Built 1986
Last Sold Summary
- 3% Below List Price
- $451/SF
- 40 Days On Market
Current Estimated Value $177,780

Last Listing Agent Cyd Scott Cohn & Company

634 Wiley Mountain Dr, Readsboro, VT 05350

/34
Est $695,646 Not Listed For Sale

196 Ways Ln, Manchester Center, VT 05255
- 4 Beds
- 3 Baths
- 2,304 Sq Ft
- Built 1929
196 Ways Ln, Manchester Center, VT 05255

Last Sold Summary
- $303/SF
- 7 Days On Market
Last Sold Price $699,000

Last Listing Agent David Halligan Four Seasons Sotheby's Int'l Realty

/4
$190,000
- 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. Current tenants keep their units up well.

Max Squiers KW Vermont - Brenda Jones Real Estate Group

32-34 Sage St, Bennington, VT 05257
/60
$285,000 Sold Feb 18, 2026

150 Fillmore St, Bennington, VT 05201
- 3 Beds
- 2 Baths
- 1,404 Sq Ft
- Built 2000
Last Sold Summary
- 4% Above List Price
- $203/SF
- 54 Days On Market
Last Listing Agent Justine Curry Maple Leaf Realty

150 Fillmore St, Bennington, VT 05201

/17
Est $315,473 Not Listed For Sale

1581 E Manchester Rd, Manchester Center, VT 05255
- 2 Beds
- 1 Bath
- 952 Sq Ft
- Built 1952
1581 E Manchester Rd, Manchester Center, VT 05255

Last Sold Summary
- 11% Above List Price
- $299/SF
- 8 Days On Market
Last Sold Price $285,000

Last Listing Agent Patti Trudel RE/MAX

/60
$1,595,000
- 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

3888 Vermont Route 7a, Shaftsbury, VT 05262
/30
$80,000 Sold Aug 13, 2025

00 Vermont 346, Pownal, VT 05260
- Land
- 9.8 Acres
- $8,163 per Acre
Last Sold Summary
- 16% Below List Price
- 69 Days On Market
Last Listing Agent Betsy Adamovich Real Broker LLC

00 Vermont 346, Pownal, VT 05260

/40
Est $1,614,217 Not Listed For Sale

2894 West Rd, Manchester Center, VT 05255
- 3 Beds
- 6 Baths
- 3,556 Sq Ft
- Built 1970
2894 West Rd, Manchester Center, VT 05255

Last Sold Summary
- 2% Below List Price
- $464/SF
- 60 Days On Market
Last Sold Price $1,650,000

Last Listing Agent Alexandra Crowley Four Seasons Sotheby's Int'l Realty

/4
$27,999
- Land
- 2.4 Acres
- $11,666 per Acre
00 Heartwellville View Rd, Readsboro, VT 05350

Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 2.4-acre lot offers the perfect blend of privacy and convenience. Power is available at the road. Whether you're seeking a peaceful retreat or a year-round residence, this spacious lot provides ample room for gardens, recreation, and more, all within a welcoming mountain community. Don't miss this opportunity to own

Flex Realty Group Flex Realty

00 Heartwellville View Rd, Readsboro, VT 05350
/56
$405,000 Sold Dec 17, 2025

130 Clark Rd, Pawlet, VT 05761
- 4 Beds
- 2 Baths
- 2,120 Sq Ft
- Built 1790
Last Sold Summary
- 3% Above List Price
- $191/SF
- 8 Days On Market
Current Estimated Value $387,045

Last Listing Agent Scott McChesney McChesney RE, Inc.

130 Clark Rd, Pawlet, VT 05761

/20
Est $579,219 Not Listed For Sale

290 Deer Meadow Rd, Manchester Center, VT 05255
- 3 Beds
- 2.5 Baths
- 1,635 Sq Ft
- Built 1970
290 Deer Meadow Rd, Manchester Center, VT 05255

Last Sold Summary
- 7% Above List Price
- $330/SF
- 57 Days On Market
Last Sold Price $540,000

Last Listing Agent Donna Murray Varick Associates Ltd

/13
$135,000 Under Contract
- Land
- 1.36 Acres
- $99,265 per Acre
0 Stratton View Rd Unit 14, Winhall, VT 05340

Stratton View Road lives up to its name. Big Views of Stratton, just 3 minutes to Stratton access road. Minutes to the snow making pond, great for walking and a dip in. the summer. There are 3 ski resorts with in 15 minutes as well as Manchester for shopping and dining. Own your piece of Vermont.

Mike England Michael England Real Estate

0 Stratton View Rd Unit 14, Winhall, VT 05340
/44
$340,000 Sold Jan 23, 2026

989 Carpenter Hill Rd, Bennington, VT 05201
- 3 Beds
- 1 Bath
- 1,660 Sq Ft
- Built 1986
Last Sold Summary
- 7% Below List Price
- $205/SF
- 85 Days On Market
Current Estimated Value $338,480

Last Listing Agent Angela Bevin Maple Leaf Realty

989 Carpenter Hill Rd, Bennington, VT 05201

/29
Est $735,100 Not Listed For Sale

110 Highland Ave, Manchester Center, VT 05255
- 5 Beds
- 3.5 Baths
- 2,912 Sq Ft
- Built 1890
110 Highland Ave, Manchester Center, VT 05255

Last Sold Summary
- 3% Above List Price
- $246/SF
- 4 Days On Market
Last Sold Price $715,000

Last Listing Agent Jamie Luke TPW Real Estate

/39
$1,289,000
- 5 Beds
- 4.5 Baths
- 4,540 Sq Ft
84 Edward Isham Dr, Manchester Center, VT 05255

Set in a desirable neighborhood just minutes from Manchester Village, this beautifully maintained home offers expansive mountain views in both directions, abundant natural light, and exceptional living space across three finished levels. Designed for comfortable living and easy entertaining, the recently renovated kitchen features a quartz island and marble countertops and opens to inviting

Katherine Zilkha Four Seasons Sotheby's Int'l Realty

84 Edward Isham Dr, Manchester Center, VT 05255
/43
$401,000 Sold May 23, 2025

515 Hillside Dr, Pownal, VT 05261
- 3 Beds
- 2.5 Baths
- 2,692 Sq Ft
- Built 1932
Last Sold Summary
- $149/SF
- 124 Days On Market
Current Estimated Value $393,875

Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

515 Hillside Dr, Pownal, VT 05261

/9
Est $671,385 Not Listed For Sale

207 Hillcrest Rd, Manchester Center, VT 05255
- 3 Beds
- 2.5 Baths
- 2,176 Sq Ft
- Built 1970
207 Hillcrest Rd, Manchester Center, VT 05255

Last Sold Summary
- 8% Above List Price
- $286/SF
- 7 Days On Market
Last Sold Price $622,500

Last Listing Agent Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

/33
$1,650,000 Under Contract
- 4 Beds
- 3.5 Baths
- 2,813 Sq Ft
264 French Hollow Rd, Bondville, VT 05340

Step into this newly constructed 2022 residence offering a rare sense of elevation—both literal and figurative—without sacrificing ease of access. While the home feels perched above it all, it is reached via a gentle sloping driveway, providing everyday convenience alongside breathtaking views. Sweeping, uninterrupted vistas are enjoyed from nearly every room, creating a constant connection to

Kristin Pirie Winhall Real Estate

264 French Hollow Rd, Bondville, VT 05340
/60
$534,000 Sold Nov 24, 2025

272 Oak Hill Rd, Shaftsbury, VT 05262
- 3 Beds
- 2.5 Baths
- 3,637 Sq Ft
- Built 2001
Last Sold Summary
- 24% Below List Price
- $147/SF
- 111 Days On Market
Current Estimated Value $590,121

Last Listing Agent Faith Rhodes Maple Leaf Realty

272 Oak Hill Rd, Shaftsbury, VT 05262

/40
Est $767,467 Not Listed For Sale

521 Barnumville Rd, Manchester Center, VT 05255
- 3 Beds
- 3 Baths
- 2,270 Sq Ft
- Built 1996
521 Barnumville Rd, Manchester Center, VT 05255

Last Sold Summary
- 6% Above List Price
- $319/SF
- 8 Days On Market
Last Sold Price $725,000

Last Listing Agent Tatsiana Clark Four Seasons Sotheby's Int'l Realty

/60
$629,000
- 5 Beds
- 3.5 Baths
- 3,271 Sq Ft
5408 Main St, Manchester Center, VT 05255

A great in town location offering two Homes,#5406 and #5408. The Front house is a three bedroom, two full bath home with a great front covered porch with views of Mt. Equinox. You can easily walk to all of Manchester Center's amenities. The back Cottage has two bedrooms, one and a half baths with kitchen and living area. This property is zoned as multi use which provides the owners the ability to

Robert Sabol Wohler Realty Group

5408 Main St, Manchester Center, VT 05255
/48
$296,500 Sold Nov 21, 2025

4 Rockwood St, Bennington, VT 05201
- 3 Beds
- 2 Baths
- 1,896 Sq Ft
- Built 1993
Last Sold Summary
- 1% Below List Price
- $156/SF
- 6 Days On Market
Current Estimated Value $296,910

Last Listing Agent Justine Curry Maple Leaf Realty

4 Rockwood St, Bennington, VT 05201

/29
Est $607,104 Not Listed For Sale

36 Boulder Rd, Manchester Center, VT 05255
- 4 Beds
- 1.5 Baths
- 2,512 Sq Ft
- Built 1825
36 Boulder Rd, Manchester Center, VT 05255

Last Sold Summary
- 7% Above List Price
- $225/SF
- 7 Days On Market
Last Sold Price $565,000

Last Listing Agent Susan Bellville Bellville Realty

/23
$340,000
- 3 Beds
- 2 Baths
- 1,590 Sq Ft
22 Carlen St, Manchester Center, VT 05255

Live in one and rent the other. Discover the charm and value of this affordable starter home with rental option. Located in a quiet, residential area of Manchester. This spacious ranch-style property offers a rare combination of flexibility, space, and opportunity, perfect for first-time buyers, investors, or anyone looking to create their dream home with a few finishing touches. The main level

Andy Reed Four Seasons Sotheby's Int'l Realty

22 Carlen St, Manchester Center, VT 05255
/22
$795,000 Sold Sep 17, 2025

185 Crooked Path Rd, Arlington, VT 05250
- 4 Beds
- 5.5 Baths
- 3,463 Sq Ft
- Built 2006
Last Sold Summary
- $230/SF
- 9 Days On Market
Current Estimated Value $812,646

Last Listing Agent Andrea Kaplan Four Seasons Sotheby's Int'l Realty

185 Crooked Path Rd, Arlington, VT 05250

/29
Est $565,152 Not Listed For Sale

335 Carlen St, Manchester Center, VT 05255
- 3 Beds
- 1.5 Baths
- 1,632 Sq Ft
- Built 1987
335 Carlen St, Manchester Center, VT 05255

Last Sold Summary
- 5% Above List Price
- $331/SF
- 4 Days On Market
Last Sold Price $540,000

Last Listing Agent Carrie Mathews Winhall Real Estate

/33
$295,000
- 4 Beds
- 2 Baths
- 1,792 Sq Ft
254 Union St, Bennington, VT 05201

Welcome to this well-maintained, solid income-producing two-family home located in the heart of town—just steps from shops, dining, and downtown events. Perfect for owner-occupants or savvy investors, this property combines classic charm with modern efficiency and low operating costs. Each two-bedroom unit features spacious, light-filled living areas, eat-in kitchen and comfortable bedrooms.

Cassie Barbeau Mahar McCarthy Real Estate

254 Union St, Bennington, VT 05201
/30
$290,000 Sold Jul 17, 2025

221 Grandview St, Bennington, VT 05201
- 3 Beds
- 1.5 Baths
- 1,042 Sq Ft
- Built 1948
Last Sold Summary
- 2% Below List Price
- $278/SF
- 75 Days On Market
Current Estimated Value $285,749

Last Listing Agent Angela Bevin Maple Leaf Realty

221 Grandview St, Bennington, VT 05201

/33
Est $783,864 Not Listed For Sale

208 Winter St, Manchester Center, VT 05255
- 5 Beds
- 3 Baths
- 1,172 Sq Ft
- Built 1984
208 Winter St, Manchester Center, VT 05255

Last Sold Summary
- 20% Above List Price
- $559/SF
- 3 Days On Market
Last Sold Price $655,000

Last Listing Agent Lisa Sullivan Four Seasons Sotheby's Int'l Realty

/29
$415,000
- 6 Beds
- 3 Baths
- 5,208 Sq Ft
126 Washington Ave, Bennington, VT 05201

Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Bennington. This distinctive 5,208± sq. ft. building combines residential and commercial opportunity, featuring three apartments and a ground-floor retail space. Original architectural details evoke the property’s historic character, while modern updates support comfortable living and reliable income potential.

Vicki Wilson Maple Leaf Realty

126 Washington Ave, Bennington, VT 05201
/2
$275,000 Sold Jul 22, 2025

0 Tunic Rd, Shaftsbury, VT 05262
- Land
- 138.31 Acres
- $1,988 per Acre
Last Sold Summary
- 54 Days On Market
Last Listing Agent Andy Reed Four Seasons Sotheby's Int'l Realty

0 Tunic Rd, Shaftsbury, VT 05262

/37
Est $784,791 Not Listed For Sale

173 N Ridge Run, Manchester Center, VT 05255
- 3 Beds
- 3 Baths
- 1,829 Sq Ft
- Built 1992
173 N Ridge Run, Manchester Center, VT 05255

Last Sold Summary
- 3% Below List Price
- $443/SF
- 6 Days On Market
Last Sold Price $810,700

Last Listing Agent Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

Showing Results 561 - 600, Page 15 of 18

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