Bennington County, VT Homes

/52
$685,000

$95K PRICE DROP Under Contract
- 4 Beds
- 4.5 Baths
- 3,423 Sq Ft
85 Limerick Ln Unit A & B, Arlington, VT 05250

Seller is offering a credit to buyers of $5000 towards closing costs at closing.• Battenkill River Frontage – Enjoy direct access to the Battenkill River, 8 shared acres, and a prime location just minutes from Manchester’s shopping, dining, skiing, biking, and hiking.• Spacious & Flexible – Light-filled 4-bedroom, 5-bath home with quality finishes, a private apartment, multiple

Margretta Fischer

Wohler Realty Group

85 Limerick Ln Unit A & B, Arlington, VT 05250
/15
$3,500 Per Month
- 2 Beds
- 2 Baths
- 1,250 Sq Ft
- Apartment for Rent
48 Della St, Manchester, VT 05255

Highland Farm is Manchester's newest residential living option. New construction on Highland Avenue. Elevator served two bedroom, two bathroom apartment. Large kitchen open to living/dining area. Laundry room in the unit. Individually metered utilities. Underground heated parking garage with assigned parking. Contact the owner/Realtor for additional information.

Christiane Carroccio TPW Real Estate

48 Della St, Manchester, VT 05255
/34
$450,000

Sold Feb 13, 2026

356 Elm St, Bennington, VT 05201
- 3 Beds
- 2.5 Baths
- 2,273 Sq Ft
- Built 1934
Last Sold Summary
- $198/SF
- 0 Days On Market
Current Estimated Value $467,160

Last Listing Agent Angela Bevin Maple Leaf Real Estate

356 Elm St, Bennington, VT 05201

/22
Not Listed For Sale

16 Clark Rd, Rupert, VT 05776
- 4 Beds
- 4 Baths
- 2,708 Sq Ft
- Built 1989
16 Clark Rd, Rupert, VT 05776

Last Sold Summary
- 19 Days On Market
Last Listing Agent Andrea Kaplan Four Seasons Sotheby's Int'l Realty

/3
$45,000

Pending
- Land
- 3.67 Acres
- $12,262 per Acre
0 Grapevine Ln Unit 5109674, Pownal, VT 05261

A rare land opportunity in Pownal!3.67 acres on a beautiful, peaceful road with so many possibilities. Whether you’ve been dreaming of building your own home or you’re looking for a private piece of Vermont land to enjoy for hunting, recreation, or simply having a place of your own, this property is worth taking a look at.On-site well and septic will be needed.This property hasn’t

Brooke Thomson Drew

Mahar McCarthy Real Estate

0 Grapevine Ln Unit 5109674, Pownal, VT 05261
/48
$42,000 Per Month
- 4 Beds
- 4 Baths
- 5,624 Sq Ft
- House for Rent
37 Burnt Hill Rd, Winhall, VT 05340

Now available for the 26-27 ski season! This spacious, luxurious post-and-beam mountain home has been owner-occupied for past winter weekends, and is now available as the ultimate ski rental just a 7-minute drive to Stratton's base lodge. Beginning with the property's 2-car garage-barn, enviable curb appeal extends throughout. An expansive, well-equipped chef's kitchen offers duel ranges and

Jamie Luke TPW Real Estate

37 Burnt Hill Rd, Winhall, VT 05340
/58
$1,495,000

Sold Jul 30, 2026

16 West Rd, Bennington, VT 05201
- 7 Beds
- 5.5 Baths
- 6,392 Sq Ft
- Built 1910
Last Sold Summary
- $234/SF
- 65 Days On Market
Current Estimated Value $1,456,129

Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

16 West Rd, Bennington, VT 05201

/36
Est $819,935

Not Listed For Sale

469 Laclair Rd, Shaftsbury, VT 05262
- 3 Beds
- 3.5 Baths
- 3,104 Sq Ft
- Built 2011
469 Laclair Rd, Shaftsbury, VT 05262

Last Sold Summary
- 3 Days On Market
Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.

/54
$1,895,000

$95K PRICE DROP
- 6 Beds
- 6.5 Baths
- 5,896 Sq Ft
27 Mountain View Rd, Winhall, VT 05360

Direct views of Stratton Mountain set the stage for this exceptional post-and-beam residence, offering a rare combination of luxury living, entertaining space, and rental flexibility. Handcrafted timber framing creates warmth and character throughout, while four fireplaces including a gas fireplace in the primary suite enhance the home's mountain atmosphere.Designed for gathering, the

Jamie Wylie Stratton Real Estate

27 Mountain View Rd, Winhall, VT 05360
/56
$885,000

Sold Jun 15, 2026

227 Kestrel Ct Unit 12, Manchester, VT 05254
- 4 Beds
- 4 Baths
- 2,924 Sq Ft
- Built 1986
Last Sold Summary
- 5% Above List Price
- $303/SF
- 2 Days On Market
Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.

227 Kestrel Ct Unit 12, Manchester, VT 05254

/40
Est $265,398

Not Listed For Sale

112 County Rd, Stamford, VT 05352
- 2 Beds
- 1 Bath
- 960 Sq Ft
- Built 1972
112 County Rd, Stamford, VT 05352

Last Sold Summary
- 5 Days On Market
Last Listing Agent Jacki Murano Southern Vermont Realty Group

/58
$2,399,000

New Construction $26K PRICE DROP
- 4 Beds
- 3.5 Baths
- 4,536 Sq Ft
33 Stone Lodge Rd, Winhall, VT 05340

Experience Premiere Luxury living in this newly built mountain residence with extraordinary panoramic views . Just minutes to Stratton Mountain'sTrails and move in ready, no detail has been overlooked with superior craftsmanship, energy efficiency and contemporary design. The handcrafted Timber Frame great room , defined by cathedral ceilings, wood burning stone hearth and expansive windows,

Kim Morgan-Wohler Wohler Realty Group

33 Stone Lodge Rd, Winhall, VT 05340
/31
$895,000

Sold Dec 12, 2025

73 Cranberry Hill Rd, Winhall, VT 05340
- 4 Beds
- 4.5 Baths
- 2,658 Sq Ft
- Built 1984
Last Sold Summary
- 8% Below List Price
- $337/SF
- 222 Days On Market
Current Estimated Value $934,592

Last Listing Agent Carrie Mathews Winhall Real Estate

73 Cranberry Hill Rd, Winhall, VT 05340

/31
Not Listed For Sale

6 Black Birch Rd, Winhall, VT 05340
- 3 Beds
- 2 Baths
- 1,215 Sq Ft
- Built 1968
6 Black Birch Rd, Winhall, VT 05340

Last Sold Summary
- 8 Days On Market
Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

/43
$1,050,000
- 4 Beds
- 4 Baths
- 2,380 Sq Ft
20 W Branch Rd, Winhall, VT 05340

Escape to the mountains and enjoy everything Stratton, Vermont has to offer in this fabulous 4 bedroom, 4 bath contemporary home, ideally located on a private cul-de-sac in the heart of Stratton Resort. Designed for gathering with family and friends, the home features a spacious open floor plan with a cathedral-ceiling living room, wood-burning fireplace, open kitchen and dining area, and plenty

MaryKate Grey Stratton Real Estate

20 W Branch Rd, Winhall, VT 05340
/44
$1,075,000

Sold Jul 17, 2026

5173 Route 30, Dorset, VT 05251
- 4 Beds
- 4.5 Baths
- 3,584 Sq Ft
- Built 1979
Last Sold Summary
- 2% Above List Price
- $300/SF
- 2 Days On Market
Current Estimated Value $1,047,629

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

5173 Route 30, Dorset, VT 05251

/40
Est $340,509

Not Listed For Sale

214 Pleasant St, Arlington, VT 05250
- 4 Beds
- 2 Baths
- 1,890 Sq Ft
- Built 1890
214 Pleasant St, Arlington, VT 05250

Last Sold Summary
- 17 Days On Market
Last Listing Agent Lilli West Maple Leaf Real Estate

/26
$749,000
- 3 Beds
- 2 Baths
- 976 Sq Ft
7 Wood Rock Rd, Winhall, VT 05340

A rare Stratton ownership opportunity with exceptional amenities and possibilities. The purchase presents an opportunity for the buyer to bypass the Stratton Mountain Club waiting list, subject to Club approval and payment of all associated fees.. Also included with the property is an active Stratton Mountain Homeowner Membership Bond, with the buyer responsible for the applicable transfer

Jamie Wylie Stratton Real Estate

7 Wood Rock Rd, Winhall, VT 05340
/31
$77,000

Sold Aug 04, 2026

109 Evergreen Dr, Bennington, VT 05201
- 3 Beds
- 1 Bath
- 1,508 Sq Ft
- Built 1940
Last Sold Summary
- 38% Below List Price
- $51/SF
- 164 Days On Market
Current Estimated Value $99,715

Last Listing Agent Zachary Zupan EXP Realty

109 Evergreen Dr, Bennington, VT 05201

/40
Est $1,630,551

Not Listed For Sale

82 High Meadow Rd, Winhall, VT 05340
- 6 Beds
- 5.5 Baths
- 4,551 Sq Ft
- Built 2002
82 High Meadow Rd, Winhall, VT 05340

Last Sold Summary
- 126 Days On Market
Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

/46
$1,599,000
- 6 Beds
- 5.5 Baths
- 5,568 Sq Ft
144 High Meadow Rd, Winhall, VT 05340

Expansive Stratton Mountain Resort Residence with exceptional floor plan and renovation! Featuring an upscale redesign of two top floor primary suite bathrooms, updated kitchen and expanded finished lower level, this home is ready for mountain living and endless entertaining! Designed with multiple gathering rooms and fireplaces, you'll enjoy apres ski with and an incredible open floor plan. Game

Kim Morgan-Wohler Wohler Realty Group

144 High Meadow Rd, Winhall, VT 05340
/17
$159,900

Sold Jun 05, 2026

432 South St Unit B2, Bennington, VT 05201
- 2 Beds
- 1.5 Baths
- 852 Sq Ft
- Built 1989
Last Sold Summary
- $188/SF
- 40 Days On Market
Current Estimated Value $173,053

Last Listing Agent Max Squiers KW Vermont - Brenda Jones Real Estate Group

432 South St Unit B2, Bennington, VT 05201

/9
Not Listed For Sale

78 Heartwellville View Rd, Readsboro, VT 05350
78 Heartwellville View Rd, Readsboro, VT 05350

Last Sold Summary
- 167 Days On Market
Last Listing Agent Jennifer Hovey-Densmore Deerfield Valley Real Estate

/60
$1,650,000
- 3 Beds
- 4 Baths
- 5,072 Sq Ft
36 Beaver St, Bondville, VT 05340

Your Ultimate Vermont Mountain Retreat Awaits! Luxury log home plus a 2,250 sqft guest house! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape - crafted for adventure, relaxation, and making lasting memories in every season. Whether you’re hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage,

MaryKate Grey Stratton Real Estate

36 Beaver St, Bondville, VT 05340
/36
$435,000

Sold Mar 24, 2026

1061 Granger Hollow Rd, North Bennington, VT 05257
- 3 Beds
- 2 Baths
- 2,108 Sq Ft
- Built 1990
Last Sold Summary
- 13% Below List Price
- $206/SF
- 215 Days On Market
Current Estimated Value $456,801

Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

1061 Granger Hollow Rd, North Bennington, VT 05257

/8
Not Listed For Sale

79 Heartwellville View Rd, Readsboro, VT 05350
79 Heartwellville View Rd, Readsboro, VT 05350

Last Sold Summary
- 167 Days On Market
Last Listing Agent Jennifer Hovey-Densmore Deerfield Valley Real Estate

/10
$20,000
- Land
- 1.2 Acres
- $16,667 per Acre
379 Oberdorf Rd, Readsboro, VT 05350

1.2 Acres of Scenic Land for Sale in Bennington County, VTEscape to the beauty of Bennington County, Vermont, with this stunning 1.2-acre parcel of vacant land. Offering 350 ft of road frontage on Oberdorf Rd, this lot provides easy access and is nestled within the private Alpenwald Village, a peaceful community ideal for your dream home or vacation retreat. Surrounded by nature, this

Community Lands Community Lands

379 Oberdorf Rd, Readsboro, VT 05350
/51
$490,000

Sold Sep 16, 2026

181 White Tail Run, Arlington, VT 05250
- 3 Beds
- 2 Baths
- 2,721 Sq Ft
- Built 1990
Last Sold Summary
- 3% Above List Price
- $180/SF
- 4 Days On Market
Current Estimated Value $460,328

Last Listing Agent Margretta Fischer Wohler Realty Group

181 White Tail Run, Arlington, VT 05250

/39
Est $366,137

Not Listed For Sale

744 Dunlap Farm Rd, Arlington, VT 05250
- 3 Beds
- 2 Baths
- 1,306 Sq Ft
- Built 1985
744 Dunlap Farm Rd, Arlington, VT 05250

Last Sold Summary
- 89 Days On Market
Last Listing Agent Monique Geannelis Mahar McCarthy Real Estate

/36
$198,000

$22K PRICE DROP
- Land
- 54 Acres
- $3,667 per Acre
399 Bard Rd, Bennington, VT 05201

Secluded serenity meets unmatched convenience on this sprawling 54+/- wooded acres in beautiful and historic Bennington, VT! Nestled among a lush mix of hard and softwoods teeming with wildlife, the property features a charming quarter-acre pond, perfect as a future homestead centerpiece, with your home set back just beyond the pond. Good access via a paved, town-maintained road leading to level

Curtis Trousdale Preferred Properties

399 Bard Rd, Bennington, VT 05201
/60
$899,000

Sold Dec 12, 2025

92 Coventry Ln, Manchester Center, VT 05255
- 4 Beds
- 2.5 Baths
- 3,215 Sq Ft
- Built 1972
Last Sold Summary
- 18% Below List Price
- $280/SF
- 101 Days On Market
Current Estimated Value $883,453

Last Listing Agent Kristin Comeau TPW Real Estate

92 Coventry Ln, Manchester Center, VT 05255

/24
Est $651,493

Not Listed For Sale

129 Coventry Ln, Manchester Center, VT 05255
- 3 Beds
- 2.5 Baths
- 2,426 Sq Ft
- Built 1972
129 Coventry Ln, Manchester Center, VT 05255

Last Sold Summary
- 68 Days On Market
Last Listing Agent Joseph Cajzer Josiah Allen Real Estate, Inc.

/27
$209,900

$10K PRICE DROP Under Contract
- 2 Beds
- 1 Bath
- 1,075 Sq Ft
1083 Main St, Bennington, VT 05201

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

Max Squiers KW Vermont - Brenda Jones Real Estate Group

1083 Main St, Bennington, VT 05201
/41
$248,000

Sold Mar 06, 2026

1160 Bergrucken Ln, Readsboro, VT 05350
- 2 Beds
- 1 Bath
- 816 Sq Ft
- Built 1978
Last Sold Summary
- 4% Below List Price
- $304/SF
- 11 Days On Market
Current Estimated Value $254,429

Last Listing Agent Morriah Adams BHG Masiello Brattleboro

1160 Bergrucken Ln, Readsboro, VT 05350

/32
Est $43,843

Not Listed For Sale

339 S Stream Rd, Pownal, VT 05261
- 5 Beds
- 2 Baths
- 2,204 Sq Ft
- Built 1890
339 S Stream Rd, Pownal, VT 05261

Last Sold Summary
- 115 Days On Market
Last Listing Agent Lisa Friedman Great American Dream Realty

/32
$1,795,000
- 5 Beds
- 3 Baths
- 5,287 Sq Ft
84 Frost Pond Rd, Dorset, VT 05251

**Privacy. Design. Nature. Possibility.** Tucked away on 12.3 acres, this exceptional contemporary retreat is the kind of property that makes you slow down the moment you arrive. A peaceful pond, mature woodlands, and complete privacy create an extraordinary setting, while the home's thoughtful architecture brings the beauty of the outdoors into every room.Wrapped in beautiful clear cedar

Carol O`Connor Four Seasons Sotheby's Int'l Realty

84 Frost Pond Rd, Dorset, VT 05251
/57
$1,575,000

Sold Oct 21, 2025

671 West Rd, Manchester Center, VT 05255
- 5 Beds
- 3.5 Baths
- 4,785 Sq Ft
- Built 1790
Last Sold Summary
- $329/SF
- 8 Days On Market
Current Estimated Value $1,805,735

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

671 West Rd, Manchester Center, VT 05255

/27
Est $200,683

Not Listed For Sale

731 Main St, Bennington, VT 05201
- 2 Beds
- 1.5 Baths
- 1,155 Sq Ft
- Built 1900
731 Main St, Bennington, VT 05201

Last Sold Summary
- 7 Days On Market
Last Listing Agent Dana Haley Real Broker LLC

/37
$995,000
- 4,724 Sq Ft
1594 Vermont Route 7a, Shaftsbury, VT 05262

Welcome to a truly unique and versatile property situated on 5 beautiful acres, offering a rare combination of residential comfort, business potential, and rental income. The main residence is a spacious 2,100 square foot home seamlessly connected to a large, fully equipped garage. This garage is a dream for automotive professionals or hobbyists, featuring two vehicle lifts, a high-ceilinged

Kelley Mccarthy Mahar McCarthy Real Estate

1594 Vermont Route 7a, Shaftsbury, VT 05262
/25
$1,200,000

Sold Jul 30, 2026

12 Beattie Ln, Manchester, VT 05254
- 3 Beds
- 2.5 Baths
- 2,736 Sq Ft
- Built 1996
Last Sold Summary
- $439/SF
- 4 Days On Market
Current Estimated Value $1,021,454

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

12 Beattie Ln, Manchester, VT 05254

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