Windham County, VT homes for sale & real estate

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48 Upper Highlands Loop, Dover, VT 05356
48 Upper Highlands Loop, Dover, VT 05356
48 Upper Highlands Loop, Dover, VT 05356
ABOUT THIS HOME
Windham County, VT Homes for Sale
Unique opportunity to own an updated and woodsy chalet just up from the slopes of Mt Snow, yet also with direct snowmobile trail access. This 5 bedroom, 2 bath home has been tastefully renovated while maintaining the charm and character befitting a Vermont retreat ski home. The interior features an open concept living space with vaulted great room, wood burning fireplace, natural woodwork and great light thanks to large windows, a kitchen off one side with live edge breakfast bar and stainless appliances, ample dining space open to the large front deck for outdoor enjoyment or potential future hot tub apres ski, there is a main floor bedroom and full updated bath, a second floor loft bedroo

$650,000

5 beds2 baths1,530 sq ft

48 Upper Highlands Loop, Dover, VT 05356

0.86 acre lot • Car-dependent

771 Stratton Mountain Access Rd #261, Stratton, VT 05155
771 Stratton Mountain Access Rd #261, Stratton, VT 05155
771 Stratton Mountain Access Rd #261, Stratton, VT 05155
ABOUT THIS HOME
Windham County, VT Homes for Sale
771 Stratton Mountain Access Rd, Stratton, VT 05155 Long Trail House is Stratton’s #1 location for owners who wish to combine personal use with an optional rental offset when not in residence. Walk to Village shops, restaurants and ski lifts. The floor plan for Long Trail House #261 is one of the largest of the 2 bedroom layouts. Master bedrooms has nice views of the Village Common. Great light in living room with extra windows due to corner location. Nice large deck. Owners storage closet and ski locker. Sold furnished.

$609,000

2 beds2 baths916 sq ft

771 Stratton Mountain Access Rd #261, Stratton, VT 05155

$942 HOA • Garage • Car-dependent

1845 Hatch School Rd, Halifax, VT 05358
1845 Hatch School Rd, Halifax, VT 05358
1845 Hatch School Rd, Halifax, VT 05358
ABOUT THIS HOME
Windham County, VT Homes for Sale
Stunning Contemporary Farmhouse with Expansive Grounds & Ultimate Privacy. Nestled in the heart of nature, this beautifully designed contemporary farmhouse offers the perfect blend of modern comfort and rustic charm. Set on a sprawling property with open fields, mature maple trees, and two serene ponds. Stone walls, a stone barn, and an orchard add to the picturesque landscape. The home features an open-concept layout with abundant natural light pouring in from windows throughout the home. The great room boasts soaring 10+ foot ceilings and a striking two-sided gas fireplace, creating a warm and inviting atmosphere. The spacious eat-in kitchen, with its stainless steel appliances and

$1,338,000

4 beds3.5 baths3,400 sq ft

1845 Hatch School Rd, Halifax, VT 05358

99 acre lot • 3 garage spots • Car-dependent

26 Spring Hill Rd, Dover, VT 05356
26 Spring Hill Rd, Dover, VT 05356
26 Spring Hill Rd, Dover, VT 05356
ABOUT THIS HOME
Windham County, VT Homes for Sale
This spectacular Post & Beam home is located just off the 13th hole of the Mount Snow Golf Course just minutes from the Mount Snow ski area. Nestled in a quiet community, with tremendous curb appeal, enjoy year round enjoyment thanks to the adjacent course, for obvious summer fun, but also snowshoeing and hiking in the winter. The interior of the home is about as good as it gets when looking for your retreat in the mountains. Beautiful rustic post and beam interior with exposed wood and joinery, a 3 story great room with large windows for natural light, a floor to ceiling stone fireplace with highly efficient wood stove insert, radiant heat in the wood flooring throughout, a large che

$1,499,000

5 beds4.5 baths4,965 sq ft

26 Spring Hill Rd, Dover, VT 05356

1.02 acre lot • 2 garage spots • Car-dependent

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32 Shattarack Rd Unit B5, Stratton, VT 05155
32 Shattarack Rd Unit B5, Stratton, VT 05155
32 Shattarack Rd Unit B5, Stratton, VT 05155
ABOUT THIS HOME
Windham County, VT Homes for Sale
Ski-in, ski-out Slopeside Townhouse! This meticulously remodeled offers everything you need for an exceptional mountain lifestyle. Inside, you’ll find your choice of two ensuite primary bedrooms, along with two additional spacious bedrooms, providing ample room and privacy for family and guests. Two bedrooms are enhanced with custom-built-ins, blending functionality with stylish design. The banisters and stairs have been replaced, adding a modern touch that complements the home’s elegant aesthetic. The bathrooms have been entirely gutted and renovated, featuring radiant heated floors that provide cozy comfort on even the coldest mornings. Radiant heat extends to the main floor,

$998,500

4 beds3.5 baths2,070 sq ft

32 Shattarack Rd Unit B5, Stratton, VT 05155

$1,095 HOA • Community pool • Car-dependent

Property at 83B Greenspring Rd, Dover, VT 05356, 3 beds, 3.5 baths

$725,000

3 beds3.5 baths2,400 sq ft

83B Greenspring Rd, Dover, VT 05356

Property at 19 Village East Rd, Wilmington, VT 05363, 4 beds, 3 baths

$895,000

4 beds3 baths2,546 sq ft

19 Village East Rd, Wilmington, VT 05363

Property at 15 Mill Rd, Dover, VT 05356, 4 beds, 3.5 baths

$570,000

4 beds3.5 baths2,604 sq ft

15 Mill Rd, Dover, VT 05356

Property at 3 Lower Highlands Rd Lot 52 ( adjoining lot is 35), Dover, VT 05356, 5 beds, 3.5 baths

$649,000

5 beds3.5 baths3,112 sq ft

3 Lower Highlands Rd Lot 52 ( adjoining lot is 35), Dover, VT 05356

Property at 43 Upton Rd, Dover, VT 05356, 6 beds, 4.5 baths

$2,000,000

6 beds4.5 baths4,950 sq ft

43 Upton Rd, Dover, VT 05356

Property at 7224 Rte 100, Wardsboro, VT 05355, 3 beds, 1.5 baths

$345,000

3 beds1.5 baths1,100 sq ft

7224 Rte 100, Wardsboro, VT 05355

Property at 30 Water St, Jamaica, VT 05343, 3 beds, 1 bath

$215,000

3 beds1 bath636 sq ft

30 Water St, Jamaica, VT 05343

Property at 9 Cooper Hill Rd, Dover, VT 05356, 4 beds, 2 baths

$625,000

4 beds2 baths1,900 sq ft

9 Cooper Hill Rd, Dover, VT 05356

Property at 37 Pleasantview Ln, Wilmington, VT 05363, 4 beds, 3.5 baths

$875,000

4 beds3.5 baths3,553 sq ft

37 Pleasantview Ln, Wilmington, VT 05363

Property at 24 Antler Loop, Dover, VT 05356, 3 beds, 2 baths

$495,000

3 beds2 baths1,943 sq ft

24 Antler Loop, Dover, VT 05356

Property at 131,133,141 Green St, Brattleboro, VT 05301, 11 baths

$1,305,000

— beds11 baths7,660 sq ft

131,133,141 Green St, Brattleboro, VT 05301

Property at 141 Green St, Brattleboro, VT 05301, 6 beds, 4 baths

$540,000

6 beds4 baths2,904 sq ft

141 Green St, Brattleboro, VT 05301

Property at 5 Alpine Loop Rd, Dover, VT 05356, 4 beds, 3 baths

$625,000

4 beds3 baths2,346 sq ft

5 Alpine Loop Rd, Dover, VT 05356

Property at 27 Haymaker Ln Unit 9H, Wilmington, VT 05363, 2 beds, 2 baths

$429,000

2 beds2 baths1,127 sq ft

27 Haymaker Ln Unit 9H, Wilmington, VT 05363

Property at 32 Circle View Dr, Dover, VT 05356, 4 beds, 3.5 baths

$749,000

4 beds3.5 baths3,360 sq ft

32 Circle View Dr, Dover, VT 05356

Property at 1614 Burbee Pond Rd, Windham, VT 05359, 5 beds, 1.5 baths

$250,000

5 beds1.5 baths1,504 sq ft

1614 Burbee Pond Rd, Windham, VT 05359

Property at 4173 & 4137 Sweet Pond Rd, Guilford, VT 05301, 4 beds, 1 bath

$349,000

4 beds1 bath1,723 sq ft

4173 & 4137 Sweet Pond Rd, Guilford, VT 05301

Property at 1324 Middle Rd, Dummerston, VT 05301, 7 beds, 7.5 baths

$2,999,000

7 beds7.5 baths8,718 sq ft

1324 Middle Rd, Dummerston, VT 05301

Property at 58 Buckboard Dr, Dover, VT 05356, 3 beds, 2.5 baths

$675,000

3 beds2.5 baths2,720 sq ft

58 Buckboard Dr, Dover, VT 05356

Property at 7 Deepwood Park, Brattleboro, VT 05301, 3 beds, 2 baths

$159,000

3 beds2 baths1,392 sq ft

7 Deepwood Park, Brattleboro, VT 05301

Property at 189 Shady Pines Park, Westminster, VT 05158, 2 beds, 1 bath

$50,000

2 beds1 bath924 sq ft

189 Shady Pines Park, Westminster, VT 05158

Property at 6738 Vt Route 100, Wardsboro, VT 05360, 3 beds, 2 baths

$299,000

3 beds2 baths1,512 sq ft

6738 Vt Route 100, Wardsboro, VT 05360

Property at 53 N Main St, Wilmington, VT 05363, 5 beds, 3 baths

$639,000

5 beds3 baths5,424 sq ft

53 N Main St, Wilmington, VT 05363

Property at 793 Grassy Brook Rd, Brookline, VT 05345, 3 beds, 2.5 baths

$645,000

3 beds2.5 baths2,705 sq ft

793 Grassy Brook Rd, Brookline, VT 05345

Property at 587 VT Route 121 E, Grafton, VT 05146, 4 beds, 3 baths

$769,000

4 beds3 baths4,379 sq ft

587 VT Route 121 E, Grafton, VT 05146

Property at E-26 Northbrook Village Way Unit 5L, Dover, VT 05356, 2 beds, 2 baths

$449,000

2 beds2 baths1,060 sq ft

E-26 Northbrook Village Way Unit 5L, Dover, VT 05356

Property at 50 Terrace St, Brattleboro, VT 05301

$680,000

— beds— baths5,540 sq ft

50 Terrace St, Brattleboro, VT 05301

Property at 60 Forest Heights Rd, Stratton, VT 05360, 4 beds, 3.5 baths

$999,800

4 beds3.5 baths2,500 sq ft

60 Forest Heights Rd, Stratton, VT 05360

Property at 370 Fischer Ln, Jamaica, VT 05343, 6 beds, 8.5 baths

$8,950,000

6 beds8.5 baths13,393 sq ft

370 Fischer Ln, Jamaica, VT 05343

Property at 1 Pheasant Ln, Dover, VT 05356, 3 beds, 3 baths

$495,000

3 beds3 baths1,813 sq ft

1 Pheasant Ln, Dover, VT 05356

Property at 89A Sun Bowl Ridge Rd Unit 89A, Stratton, VT 05155, 4 beds, 3.5 baths

$1,800,000

4 beds3.5 baths2,698 sq ft

89A Sun Bowl Ridge Rd Unit 89A, Stratton, VT 05155

Property at 23 Brook Rd, Rockingham, VT 05154, 4 beds, 3 baths

$695,000

4 beds3 baths2,978 sq ft

23 Brook Rd, Rockingham, VT 05154

Property at 20 Newell Hl, Wardsboro, VT 05360, 4 beds, 2 baths

$379,000

4 beds2 baths2,202 sq ft

20 Newell Hl, Wardsboro, VT 05360

Property at 43 First Ln #28, Wilmington, VT 05363, 3 beds, 2 baths

$425,000

3 beds2 baths1,750 sq ft

43 First Ln #28, Wilmington, VT 05363

Property at 148B Sun Bowl Ridge Rd, Stratton, VT 05255, 4 beds, 3.5 baths

$1,750,000

4 beds3.5 baths2,698 sq ft

148B Sun Bowl Ridge Rd, Stratton, VT 05255

Property at 20 Finkel Rd, Wardsboro, VT 05355, 4 beds, 2 baths

$999,000

4 beds2 baths2,741 sq ft

20 Finkel Rd, Wardsboro, VT 05355

Viewing page 5 of 9

Average home prices near Windham County, VT

Cities

Walpole homes for sale
$722,450
Westminster homes for sale
$365,000
Putney homes for sale
$637,500
Wilmington homes for sale
$582,000
Brattleboro homes for sale
$349,000
Stratton Mountain homes for sale
$998,500
Chimney Hill homes for sale
$554,000
West Brattleboro homes for sale
$349,000
Newfane homes for sale
$293,000
Bellows Falls homes for sale
$289,500

Counties

Windham County, VT real estate trends

All Home Types trends in Windham County, VT

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$399,500

-6.0% YoY | Apr 2025

1 year
3 year
5 year

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

Location

Data

Apr 2025

Growth

% YoY

Windham County, VT

$399,500

-6.0%

See more Windham County, VT market insights

More to explore in Windham County, VT

How to buy a house in Windham County, VT

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First-time homebuyer's guide

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Copyright 2025 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 Jun 06 2025 on the search page

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