Windham County, VT Homes

/24
$285,000 Sold Jun 12, 2025

730 Hubbard Hill Rd, Halifax, VT 05342
- 2 Beds
- 2 Baths
- 1,324 Sq Ft
- Built 1971
Last Sold Summary
- 4% Above List Price
- $215/SF
- 8 Days On Market
Last Listing Agent Stephanie Wilde

730 Hubbard Hill Rd, Halifax, VT 05342

/38
Est $474,729 Not Listed For Sale

95 Davis Dr, Wilmington, VT 05363
- 4 Beds
- 2 Baths
- 1,296 Sq Ft
- Built 1967
95 Davis Dr, Wilmington, VT 05363

Last Sold Summary
- 11% Below List Price
- $413/SF
- 15 Days On Market
Last Sold Price $535,000

Last Listing Agent Monique White Deerfield Valley Real Estate

/39
$869,000 Under Contract
- 5 Beds
- 3.5 Baths
- 4,626 Sq Ft
6 Brumms Way, Dover, VT 05356

Located directly across from the ski-home trail in Bears Crossing, this 2011-built home offers unbeatable access. Designed with quality and function in mind, this lodge-style retreat blends rustic charm with thoughtful modern comfort. The lot provides exceptional convenience to Mount Snow via the ski-home trail and direct shuttle service to and from the base area. Ski from the trail right to the

Adam Palmiter Berkley & Veller Greenwood/Dover

6 Brumms Way, Dover, VT 05356
/43
$229,300 Sold May 02, 2025

129 Morningside Commons, Brattleboro, VT 05301
- 2 Beds
- 2 Baths
- 1,139 Sq Ft
- Built 1998
Last Sold Summary
- $201/SF
- 28 Days On Market
Current Estimated Value $275,757

Last Listing Agent Zachary Zupan EXP Realty

129 Morningside Commons, Brattleboro, VT 05301

/38
Est $330,110 Not Listed For Sale

21 Look Rd, Wilmington, VT 05363
- 5 Beds
- 3 Baths
- 1,776 Sq Ft
- Built 1963
21 Look Rd, Wilmington, VT 05363

Last Sold Summary
- 32% Above List Price
- $141/SF
- 115 Days On Market
Last Sold Price $250,000

Last Listing Agent Steve Goldfarb Deerfield Valley Real Estate

/37
$289,000 Under Contract
- 2 Beds
- 1 Bath
- 936 Sq Ft
2378 Deer Park Rd, West Halifax, VT 05358

Set back from the road, this charming rustic cabin on 10 acres is the perfect retreat for those seeking tranquility. Enter a warm, inviting open layout with a cozy wood stove. One-level living also includes two generous bedrooms and a full bath. You have spacious front and back decks to look out onto your acres of woods. Follow a trail up to a unique, spectacular glass treehouse that is calming

Kristen Ziter Taylor Brattleboro Area Realty

2378 Deer Park Rd, West Halifax, VT 05358
/55
$479,000 Sold Aug 22, 2025

1 Dorr Fitch Rd, Dover, VT 05356
- 4 Beds
- 3 Baths
- 2,566 Sq Ft
- Built 1900
Last Sold Summary
- $187/SF
- 1 Day On Market
Current Estimated Value $483,715

Last Listing Agent Donald Koelsch Deerfield Valley Real Estate

1 Dorr Fitch Rd, Dover, VT 05356

/23
Est $532,136 Not Listed For Sale

2 Ives Rd, Wilmington, VT 05363
- 4 Beds
- 3 Baths
- 1,200 Sq Ft
- Built 1960
2 Ives Rd, Wilmington, VT 05363

Last Sold Summary
- 4% Above List Price
- $425/SF
- 159 Days On Market
Last Sold Price $510,000

Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

/17
$2,495,000
- Land
- 2.36 Acres
- $1,057,203 per Acre
4 Gold Medal Cir, Stratton, VT 05343

This lot is only one mile from the Stratton Mountain Resort's Sun Bowl base area. The lot has views of Stratton's ski trails. The Powers Subdivision has 11 lots in total and 2.71 acres of common land. Additionally, there is 69 acres of conservation land making this community very private. Build your 4-bedroom dream home right here in one of the best planned communities in southern Vermont. Lot #4

Andrew King Stratton Real Estate

4 Gold Medal Cir, Stratton, VT 05343
/30
$1,000,000 Sold Jan 30, 2026

585 Pleasant Valley Rd, Jamaica, VT 05343
- Land
- 108 Acres
- $9,259 per Acre
Last Sold Summary
- 20% Below List Price
- 293 Days On Market
Current Estimated Value $1,013,711

Last Listing Agent Britt Wohler

585 Pleasant Valley Rd, Jamaica, VT 05343

/31
Est $374,127 Not Listed For Sale

962 Chapel Hill Rd, Whitingham, VT 05361
- 3 Beds
- 2 Baths
- 1,963 Sq Ft
- Built 1988
962 Chapel Hill Rd, Whitingham, VT 05361

Last Sold Summary
- 9% Above List Price
- $174/SF
- 7 Days On Market
Last Sold Price $342,000

Last Listing Agent Jacki Murano Southern Vermont Realty Group

/23
$419,000
- 3 Beds
- 1 Bath
- 1,024 Sq Ft
1528 Townshend Rd, Grafton, VT 05146

The Storybook Cottage is a fully renovated 1940s Cape set on over two acres along the peaceful South Branch Saxtons River, just south of historic Grafton Village. Thoughtfully scaled yet rich in character, this three bedroom home offers a warm and inviting layout with pine floors, a living room anchored by a wood stove. Nearly the entire interior has been rebuilt with new Rockwool insulation and

Andie Fusco Four Seasons Sotheby's Int'l Realty

1528 Townshend Rd, Grafton, VT 05146
/28
$460,000 Sold May 01, 2025

70 Tyler St, Brattleboro, VT 05301
- 4 Beds
- 1.5 Baths
- 2,051 Sq Ft
- Built 1920
Last Sold Summary
- $224/SF
- 0 Days On Market
Current Estimated Value $485,273

Last Listing Agent Karen Hoppe Berkley & Veller Greenwood Country

70 Tyler St, Brattleboro, VT 05301

/31
Est $21,752 Not Listed For Sale

1124 Chapel Hill Rd, Whitingham, VT 05361
1124 Chapel Hill Rd, Whitingham, VT 05361

Last Sold Summary
- 9% Above List Price
- 64 Days On Market
Last Sold Price $20,000

Last Listing Agent Curtis Trousdale Preferred Properties

/23
$474,900
- 3 Beds
- 2.5 Baths
- 1,548 Sq Ft
28 Lightning Ledge Way, Wilmington, VT 05363

Private 2004 country chalet in the Chimney Hill community just outside the village of Wilmington. Hiking trails, snowmobile trail access, and convenient nearby snowmobile trailer parking, make this super convenient for the outdoorsy. This home sits on a rare double lot, just up from the beautifully renovated Chimney Hill clubhouse, Lake Whitingham, and Mount Snow ski resort, affording year round

Adam Palmiter Berkley & Veller Greenwood/Dover

28 Lightning Ledge Way, Wilmington, VT 05363
/44
$359,350 Sold Sep 26, 2025

399 Laurel Lake Rd, Jacksonville, VT 05342
- 2 Beds
- 3 Baths
- 1,696 Sq Ft
- Built 1930
Last Sold Summary
- 10% Below List Price
- $212/SF
- 17 Days On Market
Current Estimated Value $407,565

Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

399 Laurel Lake Rd, Jacksonville, VT 05342

/26
Est $238,614 Not Listed For Sale

2815 Burrington Hill Rd, Whitingham, VT 05361
- 1 Bed
- 1 Bath
- 700 Sq Ft
- Built 1982
2815 Burrington Hill Rd, Whitingham, VT 05361

Last Sold Summary
- 4% Above List Price
- $329/SF
- 6 Days On Market
Last Sold Price $230,000

Last Listing Agent Jacki Murano Southern Vermont Realty Group

/32
$2,100,000
- 7 Beds
- 4 Baths
- 4,256 Sq Ft
121 Fannie Hill Dr, Wilmington, VT 05363

Stunning contemporary chalet completely renovated in 2016 and located adjacent to the base of the Hermitage Club private ski resort. This gorgeous home sits on a private lot with direct snowmobile trail access, easy access to the ski trails, and direct to the clubhouse. Just a short drive into the village of Wilmington and the area's tremendous lakes. Thanks to the complete overhaul and

Adam Palmiter Berkley & Veller Greenwood/Dover

121 Fannie Hill Dr, Wilmington, VT 05363
/34
$405,000 Sold May 23, 2025

47B Suntec Loop, Dover, VT 05356
- 3 Beds
- 3 Baths
- 1,768 Sq Ft
- Built 1982
Last Sold Summary
- 10% Below List Price
- $229/SF
- 131 Days On Market
Last Listing Agent Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

47B Suntec Loop, Dover, VT 05356

/12
Est $245,197 Not Listed For Sale

2027 Burrington Hill Rd, Whitingham, VT 05361
2027 Burrington Hill Rd, Whitingham, VT 05361

Last Sold Summary
- 4% Above List Price
- 262 Days On Market
Last Sold Price $235,000

Last Listing Agent Kristen Breeden Southern Vermont Realty Group

/33
$19,500
- 1 Bed
- 1 Bath
- 589 Sq Ft
102, Qtr 4 Grand Summit Way Unit 102, Qtr 4, Dover, VT 05356

Trailside! Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Own this deeded quartershare property for 1 week every 28 days, on a rotating basis. This 1-of-a-kind, end-unit, slopeside 1-bedroom, 1 full bath unit has sleeping space for 4, and looks out over the Sundance Base Lodge and the Sundance Express, the new 6-person chairlift. Open-concept kitchen/dining room, and a

Donna Brown Skihome Realty

102, Qtr 4 Grand Summit Way Unit 102, Qtr 4, Dover, VT 05356
/11
$153,000 Sold Aug 25, 2025

41 Old Depot Rd, Putney, VT 05346
- Land
- 4.53 Acres
- $33,775 per Acre
Last Sold Summary
- 4% Below List Price
- 33 Days On Market
Current Estimated Value $549,826

Last Listing Agent Victoria Woods Brattleboro Area Realty

41 Old Depot Rd, Putney, VT 05346

/29
Est $534,911 Not Listed For Sale

960 Holbrook Rd, Jacksonville, VT 05342
- 3 Beds
- 2 Baths
- 2,600 Sq Ft
- Built 1968
960 Holbrook Rd, Jacksonville, VT 05342

Last Sold Summary
- 2% Above List Price
- $202/SF
- 14 Days On Market
Last Sold Price $525,000

Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

/2
$370,000
- 5 Beds
- 4 Baths
- 3,002 Sq Ft
10 Birge St, Brattleboro, VT 05301

Invest in your own home town! Full tenant roster with the easy access to laundry across the street, grocery stores, train and The Moover. Right in the heart of things with little yard to maintain! Consider as an investment in your portfolio or decide to live in one unit and have the others pay your mortgage! Good way to start, retire or increase your portfolio! Owner is a licensed appraiser.

Christine Lewis Brattleboro Area Realty

10 Birge St, Brattleboro, VT 05301
/37
$370,000 Sold Feb 12, 2026

3298 Houghtonville Rd, Grafton, VT 05146
- 4 Beds
- 2 Baths
- 2,400 Sq Ft
- Built 1890
Last Sold Summary
- 6% Below List Price
- $154/SF
- 44 Days On Market
Current Estimated Value $401,448

Last Listing Agent Alison Cummings Cummings & Co

3298 Houghtonville Rd, Grafton, VT 05146

/40
Est $432,742 Not Listed For Sale

656 Allard Rd, Whitingham, VT 05361
- 4 Beds
- 2 Baths
- 2,000 Sq Ft
- Built 1949
656 Allard Rd, Whitingham, VT 05361

Last Sold Summary
- 12% Above List Price
- $192/SF
- 56 Days On Market
Last Sold Price $385,000

Last Listing Agent Craig Ruggless EXP Realty

/16
$19,999
- Land
- 1 Acre
- $19,999 per Acre
0 Hunter Brook Rd, South Newfane, VT 05351

Beautiful creekside property in Newfane, ideal for camping, fishing, or RVing. The western boundary line follows Hunter Brook, which turns like a horseshoe at this location and almost meets the eastern boundary: Hunter Brook Road. As a result the property naturally divides itself into two sides, each with its own strengths and weaknesses.The northeastern side is larger, more private, and

David White OwnerEntry.com

0 Hunter Brook Rd, South Newfane, VT 05351
/26
$520,000 Sold Sep 25, 2025

18 Old Town Rd, West Dover, VT 05356
- 3 Beds
- 1.5 Baths
- 2,145 Sq Ft
- Built 1981
Last Sold Summary
- 5% Below List Price
- $242/SF
- 15 Days On Market
Current Estimated Value $592,355

Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

18 Old Town Rd, West Dover, VT 05356

/33
Est $269,599 Not Listed For Sale

754 Allard Rd, Whitingham, VT 05361
- 2 Beds
- 1 Bath
- 936 Sq Ft
- Built 1963
754 Allard Rd, Whitingham, VT 05361

Last Sold Summary
- 12% Above List Price
- $256/SF
- 21 Days On Market
Last Sold Price $240,000

Last Listing Agent Jon Tourville

/36
$529,000
- 3 Beds
- 2.5 Baths
- 2,044 Sq Ft
11 Dutchman Ln Unit 4A, Wilmington, VT 05363

This 3-bedroom plus loft, 2.5-bath end unit townhouse is in Powderhorn Village. The entrance boasts a mudroom, leading to a dining area adjacent to a fully equipped kitchen, complemented by a convenient powder room and living space with a wood-burning fieldstone fireplace. Access to an oversized deck and a bonus room with a hot tub and a private shower. Ascend to the second floor to find the

Jennifer Hovey-Densmore Deerfield Valley Real Estate

11 Dutchman Ln Unit 4A, Wilmington, VT 05363
/39
$475,000 Sold Apr 23, 2025

101 Washington St, Brattleboro, VT 05301
- 5 Beds
- 2.5 Baths
- 2,823 Sq Ft
- Built 1905
Last Sold Summary
- $168/SF
- 121 Days On Market
Current Estimated Value $507,824

Last Listing Agent Thomas Dahlin Berkley & Veller Greenwood Country

101 Washington St, Brattleboro, VT 05301

/32
Est $243,260 Not Listed For Sale

329 Deer Hill Rd, Whitingham, VT 05361
- 2 Beds
- 1 Bath
- 952 Sq Ft
- Built 1968
329 Deer Hill Rd, Whitingham, VT 05361

Last Sold Summary
- 6% Above List Price
- $241/SF
- 6 Days On Market
Last Sold Price $229,900

Last Listing Agent Jon Tourville

/48
$415,000 Under Contract
- 6 Beds
- 2 Baths
- 2,048 Sq Ft
58-60 Frost Place, Brattleboro, VT 05301

This turnkey income generator is now move in ready! One side is vacant and ready for your plans, the other has a successful Airbnb rental history and was completely renovated in 2018. Brand new hot water heater, dishwasher, garbage disposal, and toilet have just been installed. Both have in-unit washer & dryer. Enter through the thoughtfully crafted mudrooms with generous built-in storage. The

Lily Gautot Greenwald Realty Group

58-60 Frost Place, Brattleboro, VT 05301
/22
$89,900 Sold Jan 23, 2026

2 Wagon Dr, Brattleboro, VT 05301
- 2 Beds
- 2 Baths
- 910 Sq Ft
- Built 1977
Last Sold Summary
- $99/SF
- 6 Days On Market
Last Listing Agent Christine Lewis Brattleboro Area Realty

2 Wagon Dr, Brattleboro, VT 05301

/39
Est $595,530 Not Listed For Sale

3358 Vt Route 100, Whitingham, VT 05361
- 5 Beds
- 5 Baths
- 3,300 Sq Ft
- Built 1900
3358 Vt Route 100, Whitingham, VT 05361

Last Sold Summary
- 1% Below List Price
- $182/SF
- 118 Days On Market
Last Sold Price $599,000

Last Listing Agent Jacki Murano Southern Vermont Realty Group

/30
$315,000 Under Contract
- 3 Beds
- 1.5 Baths
- 1,674 Sq Ft
119 Newton Hill Rd, Vernon, VT 05354

You have waited long enough and now you get to take advantage of this great deal. Three bedrooms, standing seam roof, lots of natural light, natural woodwork throughout, two car detached garage, 3.5 acres - all on a cul-de-sac road in Vernon. This well-loved home is looking for someone for its next chapter. Many thoughtful features like the laundry is just off the kitchen for maximum convenience,

Jim Bellville Bellville Realty

119 Newton Hill Rd, Vernon, VT 05354
/32
$267,500 Sold Apr 21, 2025

38 Pine Tree Hill, Londonderry, VT 05148
- 2 Beds
- 1 Bath
- 864 Sq Ft
- Built 1966
Last Sold Summary
- 28% Below List Price
- $310/SF
- 117 Days On Market
Current Estimated Value $289,146

Last Listing Agent Jacki Murano Southern Vermont Realty Group

38 Pine Tree Hill, Londonderry, VT 05148

/29
Est $525,275 Not Listed For Sale

55 Reed Hill Rd, Jacksonville, VT 05342
- 5 Beds
- 3 Baths
- 2,732 Sq Ft
- Built 1840
55 Reed Hill Rd, Jacksonville, VT 05342

Last Sold Summary
- 11% Below List Price
- $216/SF
- 35 Days On Market
Last Sold Price $590,000

Last Listing Agent Leslie Fraser Four Seasons Sotheby's Int'l Realty

/15
$69,000
- Land
- 3.58 Acres
- $19,274 per Acre
Lot 4 Ghastly Job Way, Wilmington, VT 05363

3.58 acres east of Wilmington village. This property is ready to build on, site work has commenced; tree clearing and partial driveway installed, fully engineered, survey, and Sate of Vermont Wastewater Permit for the construction of a three bedroom home. This parcel offers a great location, close to Lake Raponda for swimming, near Molly Stark State Park for hiking and minutes to Lake Whitingham

Monique White Deerfield Valley Real Estate

Lot 4 Ghastly Job Way, Wilmington, VT 05363
/19
$400,000 Sold Dec 15, 2025

48 Landing Ln, Wilmington, VT 05363
- 4 Beds
- 2 Baths
- 2,056 Sq Ft
- Built 2003
Last Sold Summary
- 20% Below List Price
- $195/SF
- 52 Days On Market
Current Estimated Value $406,534

Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

48 Landing Ln, Wilmington, VT 05363

Showing Results 321 - 360, Page 9 of 18

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