Pending Listings in Windham County, VT

138 homes

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ABOUT THIS HOME
Pending Listing in Windham County, VT:
69 Grove Street is a pleasant 2 unit home just a short walk from vibrant downtown. Each unit features 2 bedrooms, bath, living room and kitchen with wide board flooring and replacement windows. The first floor unit has a covered front porch, pantry and W & D hookups in the basement. The second floor apartment has an additional room (office), W & D hookups, decking and a rear staircase. Recent improvements include a new boiler, full attic insulation and new oil tanks. Tenant pays for Heat, Electric, Water & Sewer.

$245,000

4 beds2 baths2,148 sq ft

69 Grove St, Brattleboro, VT 05301

5,227 sq ft lot • Built 1880 • Listed 110 days

CONTINGENT

ABOUT THIS HOME
Pending Listing in Windham County, VT:
Great location for primary or vacation home. Near Burbee Pond in Windhame. 2.6 acres and possibly small commercial. 4 Plus bedrooms with one full bath and a half bath on main floor. Home is ready for your improvements. Close to ski resorts!

$250,000

5 beds1.5 baths1,504 sq ft

1614 Burbee Pond Rd, Windham, VT 05359

2.6 acre lot • Garage • Built 1950

CONTINGENT

ABOUT THIS HOME
Pending Listing in Windham County, VT:
Discover this exceptional and private 12+ acre parcel, nestled along a quiet dead-end road and filled with natural beauty. Sun-drenched and serene, the property features a picturesque open meadow framed by timeless stone walls, creating an idyllic setting for your dream home. Thoughtfully prepared for construction, the property already includes many valuable improvements: a State of Vermont wastewater permit with an approved septic design for a three-bedroom residence, a drilled well producing an impressive 15 gallons per minute, 200-amp electrical service installed on-site, and fiber-optic internet available at the road. With generous road frontage and two access points, the gently sloping

$189,000

Land12.39 acres (lot)

712 Stimpson Hill Rd Lot 9, Whitingham, VT 05361

Open meadow • Wastewater permit

CONTINGENT

ABOUT THIS HOME
Pending Listing in Windham County, VT:
Nestled along Pine Acres Road in Townshend Vermont, this property offers a breathtaking vista of Stratton Mountain, located just 20 miles down the valley. The land spans approximately seven wooded acres, gently sloping at an elevation of around 1,200 feet, providing an ideal setting for constructing your dream retreat amidst the serene Vermont countryside. Conveniently situated about 20 minutes from Interstate 91 and the charming town of Brattleboro, this location also places you within a half-hour's drive of several renowned ski resorts, including Mount Snow and Stratton, with Magic and Bromley just a bit further. This is a unique opportunity to claim your own piece of Vermont, where natur

$80,000

Land7.10 acres (lot)

8 Pine Acers Ln, Townshend, VT 05359

Listed 29 days

CONTINGENT

ABOUT THIS HOME
Pending Listing in Windham County, VT:
Nestled along desirable Winhall Hollow Road in South Londonderry, this beautiful undeveloped Vermont property offers a rare opportunity to create a private mountain retreat, recreational getaway, or explore future development potential. The land features a picturesque blend of gently rolling open meadow and mature forest, with power available along the road and an old seasonal camp already in place. Ideally situated just minutes from the Stratton Mountain access road, the property provides convenient access to Stratton, Bromley, and Magic Mountain, making it an exceptional four-season location for skiing, hiking, biking, and outdoor recreation. Whether you're envisioning a secluded homesite

$450,000

Land83.07 acres (lot)

1888 Winhall Hollow Rd, South Londonderry, VT 05155

Mature forest • Recreational getaway • Power available

Property at 185 Valley View Rd, West Dover, VT 05356

$139,000

Land5.00 acres (lot)

185 Valley View Rd, West Dover, VT 05356

Property at 0 Happy Haven Rd Lot 45, Wilmington, VT 05363

$115,000

Land5.00 acres (lot)

0 Happy Haven Rd Lot 45, Wilmington, VT 05363

Property at Worden Rd, Jamaica, VT 05343

$99,000

Land6.40 acres (lot)

Worden Rd, Jamaica, VT 05343

Property at 0 Clayton Ln, Jamaica, VT 05343

$2,500

Land7,840 sq ft (lot)

0 Clayton Ln, Jamaica, VT 05343

Property at 2 North St Lot 2, Dover, VT 05431

$99,000

Land10.04 acres (lot)

2 North St Lot 2, Dover, VT 05431

Property at 11 Crescent Dr, Brattleboro, VT 05301, 2 beds, 1 bath

$16,900

2 beds1 bath672 sq ft

11 Crescent Dr, Brattleboro, VT 05301

Property at 270 Castle Hill Rd, Jamaica, VT 05343, 3 beds, 2 baths

$250,000

3 beds2 baths1,224 sq ft

270 Castle Hill Rd, Jamaica, VT 05343

Property at 1892 US RT 5, East Dummerston, VT 05346, 2 beds, 1 bath

$224,900

2 beds1 bath1,017 sq ft

1892 US RT 5, East Dummerston, VT 05346

Property at 106 Coolidge Hwy Unit 6-276, Guilford, VT 05301, 4 beds, 2.5 baths

$235,000

4 beds2.5 baths2,572 sq ft

106 Coolidge Hwy Unit 6-276, Guilford, VT 05301

Property at 23 Main St, Saxtons River, VT 05154, 4 beds, 4 baths

$200,000

4 beds4 baths5,340 sq ft

23 Main St, Saxtons River, VT 05154

Property at 3380 Under The Mountain Rd, South Londonderry, VT 05155, 4 beds, 2 baths

$295,000

4 beds2 baths1,024 sq ft

3380 Under The Mountain Rd, South Londonderry, VT 05155

Property at 373 Vermont Route 30, Newfane, VT 05345, 3 beds, 1.5 baths

$199,000

3 beds1.5 baths1,655 sq ft

373 Vermont Route 30, Newfane, VT 05345

Property at 255 Fitts Rd, Wardsboro, VT 05355, 3 beds, 1 bath

$399,000

3 beds1 bath1,440 sq ft

255 Fitts Rd, Wardsboro, VT 05355

Property at 7 High Top Rd Unit B-117, Wilmington, VT 05363, 3 beds, 2 baths

$479,999

3 beds2 baths1,410 sq ft

7 High Top Rd Unit B-117, Wilmington, VT 05363

Property at 13 Winding Hill Rd, Brattleboro, VT 05301, 2 beds, 2 baths

$115,000

2 beds2 baths1,222 sq ft

13 Winding Hill Rd, Brattleboro, VT 05301

Property at 138 Wantastiquet Dr, Brattleboro, VT 05301, 3 beds, 2 baths

$415,000

3 beds2 baths1,934 sq ft

138 Wantastiquet Dr, Brattleboro, VT 05301

Property at 90 Wilsons Woods Rd, Brattleboro, VT 05301, 3 beds, 1.5 baths

$335,000

3 beds1.5 baths1,550 sq ft

90 Wilsons Woods Rd, Brattleboro, VT 05301

Property at 1018 S Hill Rd, Jamaica, VT 05343, 2 beds, 1 bath

$189,500

2 beds1 bath893 sq ft

1018 S Hill Rd, Jamaica, VT 05343

Property at 157 Newfane Hill Rd, Newfane, VT 05345, 3 beds, 2.5 baths

$575,000

3 beds2.5 baths2,950 sq ft

157 Newfane Hill Rd, Newfane, VT 05345

Property at 412 Hall Ranch Rd, Grafton, VT 05146, 3 beds, 3 baths

$975,000

3 beds3 baths2,200 sq ft

412 Hall Ranch Rd, Grafton, VT 05146

Property at 179 Hillwinds N, Brattleboro, VT 05301, 4 beds, 2.5 baths

$599,000

4 beds2.5 baths3,576 sq ft

179 Hillwinds N, Brattleboro, VT 05301

Property at 12 Autumn Gem Dr, Dummerston, VT 05301, 3 beds, 2 baths

$325,000

3 beds2 baths1,232 sq ft

12 Autumn Gem Dr, Dummerston, VT 05301

Property at 410 School St, Westminster, VT 05158, 3 beds, 1 bath

$375,000

3 beds1 bath1,852 sq ft

410 School St, Westminster, VT 05158

Property at 2766 Windham Hill Rd, West Townshend, VT 05359, 3 beds, 3 baths

$524,000

3 beds3 baths— sq ft

2766 Windham Hill Rd, West Townshend, VT 05359

Property at 9 Village Dr, Brattleboro, VT 05301, 2 beds, 1 bath

$59,000

2 beds1 bath744 sq ft

9 Village Dr, Brattleboro, VT 05301

Property at 1309 Putney Rd, Brattleboro, VT 05301, 5 beds

$495,000

5 beds— baths3,882 sq ft

1309 Putney Rd, Brattleboro, VT 05301

Property at 36 Paul's Rd Unit 6-259, Guilford, VT 05301, 4 beds, 1.5 baths

$330,000

4 beds1.5 baths2,189 sq ft

36 Paul's Rd Unit 6-259, Guilford, VT 05301

Property at 9 Burt St, Bellows Falls, VT 05101, 4 beds, 1.5 baths

$355,000

4 beds1.5 baths2,532 sq ft

9 Burt St, Bellows Falls, VT 05101

Property at 126 Oak Grove Ave, Brattleboro, VT 05301, 5 beds, 5 baths

$425,000

5 beds5 baths3,439 sq ft

126 Oak Grove Ave, Brattleboro, VT 05301

Property at 82 Oak Grove Ave, Brattleboro, VT 05301, 3 beds, 2 baths

$350,000

3 beds2 baths1,521 sq ft

82 Oak Grove Ave, Brattleboro, VT 05301

Property at 2416 Stage Rd, Guilford, VT 05301, 4 beds, 2.5 baths

$699,000

4 beds2.5 baths2,353 sq ft

2416 Stage Rd, Guilford, VT 05301

Property at 47 Old Depot Rd, Putney, VT 05346, 3 beds, 2 baths

$369,000

3 beds2 baths1,000 sq ft

47 Old Depot Rd, Putney, VT 05346

Property at 10 Riverfront Dr, Bellows Falls, VT 05101, 2 beds, 2 baths

$275,000

2 beds2 baths1,440 sq ft

10 Riverfront Dr, Bellows Falls, VT 05101

Property at 206 Smith Rd, Jamaica, VT 05343, 4 beds, 2 baths

$89,900

4 beds2 baths1,902 sq ft

206 Smith Rd, Jamaica, VT 05343

Property at 87 Orchard St #87, Brattleboro, VT 05301, 4 beds, 3.5 baths

$359,000

4 beds3.5 baths2,800 sq ft

87 Orchard St #87, Brattleboro, VT 05301

Property at 0 Hunter Brook Rd, Marlboro, VT 05344

$65,000

Land20.80 acres (lot)

0 Hunter Brook Rd, Marlboro, VT 05344

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Pending Listings in Windham County

There are currently 138 pending listings for sale in Windham County at a median listing price of $479K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Windham County stay on the market for 75 days. This map is refreshed with the newest listings in Windham County every 15 minutes.

In the past month, 65 homes have been sold in Windham County. In addition to houses in Windham County, there were also 98 condos, 0 townhouses, and 19 multi-family units for sale in Windham County last month. Find your dream home in Windham County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Windham County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Windham County. If you're looking to sell your home in the Windham County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Windham County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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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 Fri Sep 04 2026 on the search page

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