Windham County, VT homes for sale & real estate

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570 Rockingham Rd, Rockingham, VT 05101
570 Rockingham Rd, Rockingham, VT 05101
570 Rockingham Rd, Rockingham, VT 05101
ABOUT THIS HOME
Windham County, VT Homes for Sale
What a great opportunity! This property in its heyday was a thriving Gift Shop and small campground, the owners lived on premises in a charming dormered cape. It has since fallen in disrepair but offers endless opportunity to the right person! The house is a three bedroom cape with a small attached studio apartment and a two car garage with a level, sunny, and private yard. The Gift Shop is almost 2,000 sq ft. includes a bathroom, office space and garage. Lots of window and high ceilings, it could be adapted for many different uses, artist studio, workshop, the possibilities are endless. The property is being sold "AS IS".

$220,000

3 beds2 baths2,262 sq ft

570 Rockingham Rd, Rockingham, VT 05101

5 acre lot • 2 garage spots • Car-dependent

6878 Streeter Rd Unit 9&10, Wardsboro, VT 05360
6878 Streeter Rd Unit 9&10, Wardsboro, VT 05360
6878 Streeter Rd Unit 9&10, Wardsboro, VT 05360
ABOUT THIS HOME
Windham County, VT Homes for Sale
Excellent opportunity to be close to everything Vermont has to offer and still feel secluded. This off grid efficient home is so easy to live in, get to and enjoy. IF you'd like to be on grid you're only about 7 power poles away. This offering is for currently combined 2 buildable lots which were subdivided many years ago. There is wonderful access to the woods for all activities. You can move right in and take advantage of the 2 batteries, 2 generators, propane wood stove set up on the thermostat, washer, 12 volt refrigerator, on demand never ending hot water (the seller Loves taking Long Long Hot showers), stained glass, custom metal work, air conditioning, an oversized garage with attach

$425,000

1 bed1 bath700 sq ft

6878 Streeter Rd Unit 9&10, Wardsboro, VT 05360

8.15 acre lot • 2 garage spots • Car-dependent

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12 Conifer Ln, Wilmington, VT 05363
12 Conifer Ln, Wilmington, VT 05363
12 Conifer Ln, Wilmington, VT 05363
ABOUT THIS HOME
Windham County, VT Homes for Sale
Welcome to 12 Conifer Lane, your private 3 bedroom 3 bath escape in beautiful Southern Vermont. Built with quality construction and a 5 star energy rating, this home is move-in ready and should provide years of stress free ownership. The feeling inside is comfortable and cozy. Cathedral ceilings in the open concept living and dining room are anchored by the wood burning fireplace, making it a great place to unwind and relax after a day on the slopes or at the lake. The large open kitchen is a great space to prepare your meals and includes a breakfast bar, energy star stainless steel appliances, and granite countertops. An ensuite primary bedroom along with another half bath and laundry room

$630,000

3 beds2.5 baths2,100 sq ft

12 Conifer Ln, Wilmington, VT 05363

3.7 acre lot • $67 HOA • 2 garage spots

8577 VT Route 30 Unit H, Jamaica, VT 05343
8577 VT Route 30 Unit H, Jamaica, VT 05343
8577 VT Route 30 Unit H, Jamaica, VT 05343
ABOUT THIS HOME
Windham County, VT Homes for Sale
Welcome to The Willows! Where convenience, comfort, and value come together in this well-appointed 2 bedroom, 1 bathroom condominium. Set privately back from Route 30, this thoughtfully maintained unit offers peaceful surroundings just two minutes from Strattons Access Road and within easy reach of Jamaica State Park and the West River. Ideal for first-time homebuyers or those looking to purchase their first vacation property, this condo is a rare opportunity to enjoy Vermonts outdoor lifestyle without the burden of high carrying costs or extensive maintenance. It is being offered furnished (excluding personal items) and features a cozy wood stove for added warmth. Enjoy the simplicity of c

$205,000

2 beds1 bath844 sq ft

8577 VT Route 30 Unit H, Jamaica, VT 05343

1 acre lot • $293 HOA • Car-dependent

3730 Route 100, Wardsboro, VT 05355
3730 Route 100, Wardsboro, VT 05355
3730 Route 100, Wardsboro, VT 05355
ABOUT THIS HOME
Windham County, VT Homes for Sale
Property is being sold "as is where is" and does need some TLC. The house is set back off the road quite a bit for total privacy and there is a pond on the property. There is a one car garage, a full daylight basement, and a sun room.

$450,000

4 beds3.5 baths2,575 sq ft

3730 Route 100, Wardsboro, VT 05355

10 acre lot • Garage • Car-dependent

Property at 115/17 Qtr.4,89 Grand Summit Way, Dover, VT 05356, 1 bed, 2 baths

$32,000

1 bed2 baths709 sq ft

115/17 Qtr.4,89 Grand Summit Way, Dover, VT 05356

Property at 673 Route 121 E, Grafton, VT 05146, 5 beds, 2.5 baths

$639,000

5 beds2.5 baths3,000 sq ft

673 Route 121 E, Grafton, VT 05146

Property at 29 Canal St, Brattleboro, VT 05301, 18 beds, 8 baths

$745,000

18 beds8 baths4,932 sq ft

29 Canal St, Brattleboro, VT 05301

Property at 601 Bellows Falls Rd, Putney, VT 05346, 3 beds, 2 baths

$849,000

3 beds2 baths2,216 sq ft

601 Bellows Falls Rd, Putney, VT 05346

Property at 3 Mill Rd, Dover, VT 05356, 4 beds, 2.5 baths

$499,000

4 beds2.5 baths2,060 sq ft

3 Mill Rd, Dover, VT 05356

Property at 3432 US Route 5, Westminster, VT 05158, 4 beds, 1.5 baths

$365,000

4 beds1.5 baths2,115 sq ft

3432 US Route 5, Westminster, VT 05158

Property at 63A Sun Bowl Ridge Rd Unit 63A, Stratton, VT 05255-9847, 4 beds, 3.5 baths

$1,750,000

4 beds3.5 baths2,698 sq ft

63A Sun Bowl Ridge Rd Unit 63A, Stratton, VT 05255-9847

Property at 16A Snow Tree Ln Unit Cedars 1, Dover, VT 05356, 3 beds, 2.5 baths

$539,000

3 beds2.5 baths2,150 sq ft

16A Snow Tree Ln Unit Cedars 1, Dover, VT 05356

Property at 21 Howard St, Brattleboro, VT 05301, 3 beds, 3 baths

$495,000

3 beds3 baths2,400 sq ft

21 Howard St, Brattleboro, VT 05301

Property at 61 E Country Club Rd, Dover, VT 05356-0527, 3 beds, 2.5 baths

$350,000

3 beds2.5 baths1,440 sq ft

61 E Country Club Rd, Dover, VT 05356-0527

Property at 759 Stratton Mountain Access Rd #339, Stratton, VT 05155, 3 beds, 3 baths

$1,050,000

3 beds3 baths1,501 sq ft

759 Stratton Mountain Access Rd #339, Stratton, VT 05155

Property at 343 Haystack Rd, Wilmington, VT 05363, 7 beds, 5 baths

$529,000

7 beds5 baths2,978 sq ft

343 Haystack Rd, Wilmington, VT 05363

Property at 6940 Coolidge Hwy, Guilford, VT 05301, 3 beds, 2.5 baths

$525,000

3 beds2.5 baths2,023 sq ft

6940 Coolidge Hwy, Guilford, VT 05301

Property at 301 Maple St, Brattleboro, VT 05301, 4 beds, 2 baths

$650,000

4 beds2 baths3,090 sq ft

301 Maple St, Brattleboro, VT 05301

Property at 23 Summit Meadows Cir, Dover, VT 05356, 5 beds, 4 baths

$599,000

5 beds4 baths3,023 sq ft

23 Summit Meadows Cir, Dover, VT 05356

Property at 2779 Pikes Falls Rd, Jamaica, VT 05343, 3 beds, 1 bath

$415,000

3 beds1 bath1,338 sq ft

2779 Pikes Falls Rd, Jamaica, VT 05343

Property at 4 L Trailside Village Way Unit H34, Dover, VT 05356, 4 beds, 4 baths

$799,000

4 beds4 baths1,575 sq ft

4 L Trailside Village Way Unit H34, Dover, VT 05356

Property at 6 G Northbrook Village Way #23, Dover, VT 05356, 2 beds, 2 baths

$439,000

2 beds2 baths1,040 sq ft

6 G Northbrook Village Way #23, Dover, VT 05356

Property at 14H Trailside Village Way Unit K24, Dover, VT 05356, 2 beds, 2 baths

$499,000

2 beds2 baths1,200 sq ft

14H Trailside Village Way Unit K24, Dover, VT 05356

Property at 14 Clark Ave, Brattleboro, VT 05301, 8 beds, 4 baths

$600,000

8 beds4 baths3,910 sq ft

14 Clark Ave, Brattleboro, VT 05301

Property at 47 Adams St, Westminster, VT 05158, 3 beds, 1.5 baths

$185,000

3 beds1.5 baths1,664 sq ft

47 Adams St, Westminster, VT 05158

Property at 5 Black Bear Ln Unit 5 F, Dover, VT 05356, 2 beds, 2 baths

$374,000

2 beds2 baths1,250 sq ft

5 Black Bear Ln Unit 5 F, Dover, VT 05356

Property at 70 Worden Ln, Townshend, VT 05359, 3 beds, 1.5 baths

$330,000

3 beds1.5 baths1,602 sq ft

70 Worden Ln, Townshend, VT 05359

Property at 6795 Vt Route 100, Londonderry, VT 05148, 4 beds, 2 baths

$425,000

4 beds2 baths2,460 sq ft

6795 Vt Route 100, Londonderry, VT 05148

Property at 22 Chestnut St, Brattleboro, VT 05301, 6 beds, 4 baths

$544,400

6 beds4 baths3,000 sq ft

22 Chestnut St, Brattleboro, VT 05301

Property at 696 S Wardsboro Rd, Wardsboro, VT 05355-4415, 4 beds, 1.5 baths

$385,000

4 beds1.5 baths1,404 sq ft

696 S Wardsboro Rd, Wardsboro, VT 05355-4415

Property at 412 Western Ave, Brattleboro, VT 05301, 3 beds, 2.5 baths

$315,000

3 beds2.5 baths2,014 sq ft

412 Western Ave, Brattleboro, VT 05301

Property at 151 Holland Rd, Dover, VT 05341, 4 beds, 2.5 baths

$999,000

4 beds2.5 baths2,520 sq ft

151 Holland Rd, Dover, VT 05341

Property at 29A Maple Hill Loop, Dover, VT 05356, 3 beds, 3.5 baths

$399,000

3 beds3.5 baths1,500 sq ft

29A Maple Hill Loop, Dover, VT 05356

Property at 56 Shattarack Rd Unit D6, Stratton, VT 05155, 3 beds, 3.5 baths

$995,000

3 beds3.5 baths1,800 sq ft

56 Shattarack Rd Unit D6, Stratton, VT 05155

Property at 49 High Point Dr Unit A122, Stratton, VT 05155, 3 beds, 3 baths

$650,000

3 beds3 baths2,341 sq ft

49 High Point Dr Unit A122, Stratton, VT 05155

Property at 47 Ives Rd, Wilmington, VT 05363, 5 beds, 3.5 baths

$625,000

5 beds3.5 baths2,240 sq ft

47 Ives Rd, Wilmington, VT 05363

Property at 18 Dover Green Rd, Dover, VT 05356, 3 beds, 2 baths

$399,000

3 beds2 baths1,200 sq ft

18 Dover Green Rd, Dover, VT 05356

Property at 141 W Ridge Rd, Stratton, VT 05155, 6 beds, 5 baths

$4,300,000

6 beds5 baths4,715 sq ft

141 W Ridge Rd, Stratton, VT 05155

Property at 85 E Birch Rd #21, Stratton, VT 05155, 2 beds, 2 baths

$369,000

2 beds2 baths1,150 sq ft

85 E Birch Rd #21, Stratton, VT 05155

Property at 121 Dover Hill Rd, Dover, VT 05341, 3 beds, 2 baths

$635,000

3 beds2 baths3,000 sq ft

121 Dover Hill Rd, Dover, VT 05341

Viewing page 3 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 Sat Jun 07 2025 on the search page

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