Windham County, VT homes for sale & real estate

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35 Hillcrest Ter, Brattleboro, VT 05301
35 Hillcrest Ter, Brattleboro, VT 05301
35 Hillcrest Ter, Brattleboro, VT 05301
ABOUT THIS HOME
Windham County, VT Homes for Sale
Open House August 1, 5:30-7:00 and August 2, 10-11:30. Welcome to 35 Hillcrest Terrace, a well-loved home owned by the same family for over 20 years, perfectly situated in one of Brattleboro’s most convenient neighborhoods. Just moments from Memorial Park, this charming property offers easy access to recreation, walking trails, and town amenities while providing a peaceful, residential setting. This 3-bedroom home is move-in ready yet offers plenty of potential for updates, making it the perfect opportunity to truly make it your own. The main level features a comfortable layout, filled with natural light, and opens to a delightful 3-season porch—ideal for morning coffee or eve

$299,900

3 beds2.5 baths1,025 sq ft

35 Hillcrest Ter, Brattleboro, VT 05301

0.36 acre lot • Garage • Car-dependent

NEW 18 HRS AGO

1966 Thompsonburg Rd, Londonderry, VT 05155
1966 Thompsonburg Rd, Londonderry, VT 05155
1966 Thompsonburg Rd, Londonderry, VT 05155
ABOUT THIS HOME
Windham County, VT Homes for Sale
A quiet, private sanctuary in a prime location—just minutes from all three local ski areas, Lowell Lake, and the shopping and dining of Londonderry and Manchester. This 4-bedroom retreat is ready to be loved by a new family. Enjoy newly updated bathrooms, appliances, countertops, a new chimney liner, a wood-burning fireplace, and a wood stove insert that makes the family room especially cozy on chilly winter days. It’s the perfect place to unwind after a day on the slopes, hiking, biking, golfing, or simply soaking in the fall foliage. There's room for everyone in this warm, inviting, and very private setting. The insulated, wood-heated 3-car garage with a workshop is ideal for

$529,000

4 beds2.5 baths1,864 sq ft

1966 Thompsonburg Rd, Londonderry, VT 05155

4.12 acre lot • 3 garage spots • Car-dependent

52 Spruce Lake Ests, Wilmington, VT 05363
52 Spruce Lake Ests, Wilmington, VT 05363
52 Spruce Lake Ests, Wilmington, VT 05363
ABOUT THIS HOME
Windham County, VT Homes for Sale
25 private acres with lake frontage, stunning lake & mountain scenery, and a beautifully maintained 3,300+ sq ft home w/ direct-entry 2-car garage. Located in private Spruce Lake Estates—close proximity to Mount Snow & Hermitage Club, State Parks, restaurants, shops and public transportation—this rare property offers 4-season living w/ space, privacy & frontage on a non-motorized lake w/ beach, swim platform & tennis on site. Thoughtfully designed to embrace its setting, the home offers lake & mountain views from all 3 finished levels and seamless indoor-outdoor flow. Main level features a vaulted great room w/ exposed beams, wood-burning fireplace,

$739,000

3 beds3.5 baths3,050 sq ft

52 Spruce Lake Ests, Wilmington, VT 05363

25 acre lot • 2 garage spots • Car-dependent

111 Hughes Ln, Jamaica, VT 05343
111 Hughes Ln, Jamaica, VT 05343
111 Hughes Ln, Jamaica, VT 05343
ABOUT THIS HOME
Windham County, VT Homes for Sale
Fully renovated in 2022, 450 ft of lake front footage on picturesque Cole Pond. Nestled on nearly 2 acres in Jamaica, VT, this stunning single family home at 111 Hughes Lane was built in 1989 and offers a peaceful retreat for its next owners. With 3 bedrooms, 3 bathrooms, and 1 half bathroom, and 4 built-in adult size bunks for comfortable sleeping of 10, Air-conditioned master bedroom and media room, dry bar and high-end appliances in this spacious home boasting a generous finished area of 3,300 sf. The property features a beautifully landscaped lot spanning over 77,972 sf. , providing ample space for outdoor activities and relaxation. Perfect for those seeking a serene and private settin

$1,499,999

3 beds3.5 baths3,300 sq ft

111 Hughes Ln, Jamaica, VT 05343

1.78 acre lot • Car-dependent

3D WALKTHROUGH

637 Wiswall Hill Rd, Townshend, VT 05353
637 Wiswall Hill Rd, Townshend, VT 05353
637 Wiswall Hill Rd, Townshend, VT 05353
ABOUT THIS HOME
Windham County, VT Homes for Sale
Discover your perfect Vermont escape in this cozy two-story cabin nestled on a sweet, level acre. Whether you're looking for a weekend getaway or a full-time residence, this home offers the ideal blend of rustic charm and everyday functionality. The lower level welcomes you into an open-concept guest or living space, with convenient access to utilities and a fenced-in shaded area—perfect for pets or outdoor play. Upstairs you'll find the heart of the home. A quaint kitchen features handmade cabinetry, a delightful greenhouse window, and a breakfast bar that opens to the vaulted-ceiling living room. Natural light floods the space through skylights and a sliding glass door, creating a w

$263,000

2 beds1 bath1,440 sq ft

637 Wiswall Hill Rd, Townshend, VT 05353

1 acre lot • Car-dependent

Property at 53 Hickory Ridge Rd S, Putney, VT 05346, 2 beds, 2 baths

$369,000

2 beds2 baths1,020 sq ft

53 Hickory Ridge Rd S, Putney, VT 05346

Property at 341 Under The Mountain Rd, Londonderry, VT 05155, 5 beds, 3 baths

$730,000

5 beds3 baths2,635 sq ft

341 Under The Mountain Rd, Londonderry, VT 05155

Property at 5704 Coolidge Hwy, Guilford, VT 05301, 3 beds, 1 bath

$249,000

3 beds1 bath1,213 sq ft

5704 Coolidge Hwy, Guilford, VT 05301

Property at 163/65 Qtr.1,89 Grand Summit Way, Dover, VT 05356, 1 bed, 2 baths

$28,500

1 bed2 baths771 sq ft

163/65 Qtr.1,89 Grand Summit Way, Dover, VT 05356

Property at 5 Camelot Dr, Wilmington, VT 05363, 3 beds, 2 baths

$249,000

3 beds2 baths1,960 sq ft

5 Camelot Dr, Wilmington, VT 05363

Property at 4B Dogwood Trl, Stratton, VT 05155, 3 beds, 3 baths

$995,000

3 beds3 baths1,900 sq ft

4B Dogwood Trl, Stratton, VT 05155

Property at 10 Crosstown Rd, Dover, VT 05356, 2 beds, 1.5 baths

$369,000

2 beds1.5 baths1,320 sq ft

10 Crosstown Rd, Dover, VT 05356

Property at 1469 Higley Hill Rd, Marlboro, VT 05363, 4 beds, 2 baths

$399,000

4 beds2 baths1,768 sq ft

1469 Higley Hill Rd, Marlboro, VT 05363

Property at 137 Stratton Arlington Rd, Wardsboro, VT 05360, 4 beds, 1.5 baths

$499,000

4 beds1.5 baths2,100 sq ft

137 Stratton Arlington Rd, Wardsboro, VT 05360

Property at 532 Sherwood Frst, Londonderry, VT 05148, 3 beds, 3 baths

$595,000

3 beds3 baths2,761 sq ft

532 Sherwood Frst, Londonderry, VT 05148

Property at 43 Bear Lair Ln, Wilmington, VT 05363, 3 beds, 2 baths

$375,000

3 beds2 baths1,152 sq ft

43 Bear Lair Ln, Wilmington, VT 05363

Property at 72 Kidder Hill Rd, Grafton, VT 05146, 4 beds, 3.5 baths

$499,000

4 beds3.5 baths3,301 sq ft

72 Kidder Hill Rd, Grafton, VT 05146

Property at 17 Tinker Hill Rd, Guilford, VT 05301, 4 beds, 2 baths

$425,000

4 beds2 baths2,445 sq ft

17 Tinker Hill Rd, Guilford, VT 05301

Property at 122,qtr 1 Grand Summit Way, Dover, VT 05356, 1 bed, 1 bath

$18,000

1 bed1 bath673 sq ft

122,qtr 1 Grand Summit Way, Dover, VT 05356

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 55 Crosstown Rd, Dover, VT 05356, 4 beds, 3 baths

$750,000

4 beds3 baths2,160 sq ft

55 Crosstown Rd, Dover, VT 05356

Property at 10 Taylor St, Rockingham, VT 05101

$125,000

— beds— baths1,968 sq ft

10 Taylor St, Rockingham, VT 05101

Property at 321 Leonard Rd, Dummerston, VT 05301, 3 beds, 2 baths

$499,000

3 beds2 baths1,568 sq ft

321 Leonard Rd, Dummerston, VT 05301

Property at 452 Sherwood Frst, Londonderry, VT 05148, 5 beds, 3 baths

$499,000

5 beds3 baths2,600 sq ft

452 Sherwood Frst, Londonderry, VT 05148

Property at 1176 E Dover Rd, Wardsboro, VT 05355, 2 beds, 1.5 baths

$645,000

2 beds1.5 baths1,530 sq ft

1176 E Dover Rd, Wardsboro, VT 05355

Property at 442 McMillan Rd, Whitingham, VT 05361, 4 beds, 2 baths

$469,000

4 beds2 baths— sq ft

442 McMillan Rd, Whitingham, VT 05361

Property at 150 Williams St, Londonderry, VT 05148, 3 beds, 2.5 baths

$369,000

3 beds2.5 baths1,304 sq ft

150 Williams St, Londonderry, VT 05148

Property at 159 Westminster Rd, Putney, VT 05346, 4 beds, 3.5 baths

$735,000

4 beds3.5 baths4,540 sq ft

159 Westminster Rd, Putney, VT 05346

Property at 28 Cheney Brook Rd, Dover, VT 05356, 3 beds, 2 baths

$679,000

3 beds2 baths1,500 sq ft

28 Cheney Brook Rd, Dover, VT 05356

Property at 43 First Ln #25, Wilmington, VT 05363, 2 beds, 2 baths

$339,500

2 beds2 baths1,240 sq ft

43 First Ln #25, Wilmington, VT 05363

Property at 225 Church Ave, Westminster, VT 05101, 6 beds, 2 baths

$389,000

6 beds2 baths2,787 sq ft

225 Church Ave, Westminster, VT 05101

Property at 112 Robin Hill Rd, Townshend, VT 05353, 2 beds, 1 bath

$335,000

2 beds1 bath1,659 sq ft

112 Robin Hill Rd, Townshend, VT 05353

Property at 85 Browns Rd, Newfane, VT 05345, 2 beds, 2 baths

$795,000

2 beds2 baths2,190 sq ft

85 Browns Rd, Newfane, VT 05345

Property at 41 Two Brook Dr, Wilmington, VT 05363, 4 beds, 4 baths

$979,000

4 beds4 baths3,420 sq ft

41 Two Brook Dr, Wilmington, VT 05363

Property at 4E Trailside Village Way Unit H21, Dover, VT 05356, 3 beds, 3 baths

$687,500

3 beds3 baths1,400 sq ft

4E Trailside Village Way Unit H21, Dover, VT 05356

Property at 33D White Oaks Loop #38, Dover, VT 05356, 3 beds, 3 baths

$515,000

3 beds3 baths2,016 sq ft

33D White Oaks Loop #38, Dover, VT 05356

Property at 204 Meetinghouse Ln, Brattleboro, VT 05301, 4 beds, 2 baths

$579,000

4 beds2 baths2,656 sq ft

204 Meetinghouse Ln, Brattleboro, VT 05301

Property at 505 Smith Rd, Halifax, VT 05358, 2 beds, 1 bath

$224,000

2 beds1 bath550 sq ft

505 Smith Rd, Halifax, VT 05358

Property at 136 Woodsman Ext, Dover, VT 05356, 4 beds, 4 baths

$1,989,000

4 beds4 baths4,000 sq ft

136 Woodsman Ext, Dover, VT 05356

Property at 133 Howes Loop, Wilmington, VT 05363, 4 beds, 3.5 baths

$1,225,000

4 beds3.5 baths4,503 sq ft

133 Howes Loop, Wilmington, VT 05363

Property at 516 Rockingham Hill Rd, Rockingham, VT 05154, 5 beds, 3.5 baths

$789,000

5 beds3.5 baths2,968 sq ft

516 Rockingham Hill Rd, Rockingham, VT 05154

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Average home prices near Windham County, VT

Cities

Walpole homes for sale
$999,500
Westminster homes for sale
Putney homes for sale
$587,450
Wilmington homes for sale
$450,000
Brattleboro homes for sale
$342,000
Stratton Mountain homes for sale
$845,000
Chimney Hill homes for sale
$499,000
West Brattleboro homes for sale
$334,500
Jacksonville homes for sale
$344,000
Newfane homes for sale
$343,450
Bellows Falls homes for sale
$315,000

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)

$342,000

-7.3% YoY | Jun 2025

1 year
3 year
5 year

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

Location

Data

Jun 2025

Growth

% YoY

Windham County, VT

$342,000

-7.3%

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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Popular Markets in Vermont

Burlington homes for sale
$630,745
Stowe homes for sale
$899,000
Woodstock homes for sale
$987,500
Montpelier homes for sale
$459,000
Brattleboro homes for sale
$339,000
South Burlington homes for sale
$710,000
Shelburne homes for sale
$684,500
Waterbury homes for sale
$350,000
Manchester homes for sale
$1,247,500
Rutland homes for sale
$277,000
Ludlow homes for sale
$529,000
Bennington homes for sale
$272,000
Barre homes for sale
$285,000
Middlebury homes for sale
$675,000
Norwich homes for sale
$1,027,000

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 Wed Jul 30 2025 on the search page

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