Windham County, VT Homes

/33
$1,760,000
- 4 Beds
- 3.5 Baths
- 2,698 Sq Ft
89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360

Trailside!!! Ski in, ski out!! The very best Ski Direct Access at Stratton!! Most popular of luxury townhomes---offering an enlarged patio with Hot Tub, Open and Sunny, Four Bedrooms plus a Den Floorplan, Single Car Garage! Fully Furnished. Hardwood Flooring, floor to ceiling stone, wood burning fireplace! Enjoy this outstanding trailside location. And as an added benefit, the Stratton Training

Edwin Kevil Stratton Real Estate

89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360
/30
$1,400 per month
- 2 Beds
- 1 Bath
- 1,000 Sq Ft
- Condo for Rent
210 Elliot St Unit 3, Brattleboro, VT 05301

210 Elliot St Unit 3, Brattleboro, VT 05301
/34
$200,000 Sold Oct 17, 2025

533 Pratt Bridge Rd, Jamaica, VT 05343
- 3 Beds
- 2 Baths
- 2,613 Sq Ft
- Built 1970
Last Sold Summary
- 27% Below List Price
- $77/SF
- 25 Days On Market
Current Estimated Value $236,326

Last Listing Agent Mike England Michael England Real Estate

533 Pratt Bridge Rd, Jamaica, VT 05343

/32
Est $472,927 Not Listed For Sale

476 Edie Ln, Jamaica, VT 05343
- 3 Beds
- 3 Baths
- 1,800 Sq Ft
- Built 1988
476 Edie Ln, Jamaica, VT 05343

Last Sold Summary
- 5% Above List Price
- $249/SF
- 40 Days On Market
Last Sold Price $449,000

Last Listing Agent Carrie Mathews Winhall Real Estate

/79
$275,000
- Land
- 22.32 Acres
- $12,321 per Acre
81 Parish Hill Rd Unit 26, Newfane, VT 05345

Tucked away in the quiet hills of South Newfane, Vermont, this property presents an excellent opportunity to own a secluded off-grid retreat with endless potential. Spanning 22.32 acres of mixed timberland, the land offers both natural beauty and outdoor recreation, while the cabin provides a comfortable base that is already well on its way to completion.The cabin itself measures 715 square feet

Chad Bruyette Whitetail Properties Real Estate

81 Parish Hill Rd Unit 26, Newfane, VT 05345
/18
$22,000 per month
- 3 Beds
- 2 Baths
- 2,255 Sq Ft
- House for Rent
378 Tuttle Hill Rd, Londonderry, VT 05155

Get ahead of the '26-'27 ski season with this turnkey mountain modern gem. Fully renovated with attention to detail, this cheerful, sunny Scandinavian Modern space welcomes and inspires. 15 minutes to Stratton Base, 14 minutes to Bromley Village, and 10 minutes to Magic Mountain, you are in the middle of it all, with your choice to either explore or stick to your home mountain. The main floor

Jamie Luke TPW Real Estate

378 Tuttle Hill Rd, Londonderry, VT 05155
/54
$1,743,600 Sold Sep 30, 2025

1324 Middle Rd, Brattleboro, VT 05301
- 7 Beds
- 7.5 Baths
- 8,718 Sq Ft
- Built 2005
Last Sold Summary
- 50% Below List Price
- $200/SF
- 274 Days On Market
Current Estimated Value $1,756,171

Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

1324 Middle Rd, Brattleboro, VT 05301

/24
Est $241,023 Not Listed For Sale

1751 Rockingham Rd, Rockingham, VT 05143
- 2 Beds
- 1.5 Baths
- 1,120 Sq Ft
- Built 1989
1751 Rockingham Rd, Rockingham, VT 05143

Last Sold Summary
- 34% Above List Price
- $161/SF
- 14 Days On Market
Last Sold Price $180,000

Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

/8
$275,000 Under Contract
- Land
- 34.53 Acres
- $7,964 per Acre
0 W Hill Rd, Jamaica, VT 05343

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 3 is 34.53 acres, and is mostly forested near the access road. A driveway would need to be

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/38
$2,000 per month
- 3 Beds
- 1 Bath
- 2,200 Sq Ft
- Condo for Rent
197 Western Ave Unit 2 - Upstairs, Brattleboro, VT 05301

Available December 1Spacious and sun-filled 3-bedroom apartment with an additional office, offering room to live, work, and relax. Enjoy a full dining room, large kitchen, comfortable living room, and your own private porch—perfect for morning coffee or unwinding at the end of the day.This home features new windows, clean carpeting, and excellent natural light from every direction. You’ll

197 Western Ave Unit 2 - Upstairs, Brattleboro, VT 05301
/59
$360,000 Sold Sep 26, 2025

45 Dorr Fitch Rd, West Dover, VT 05356
- 5 Beds
- 3.5 Baths
- 2,800 Sq Ft
- Built 1968
Last Sold Summary
- 14% Below List Price
- $129/SF
- 10 Days On Market
Current Estimated Value $412,684

Last Listing Agent Rich Caplan Deerfield Valley Real Estate

45 Dorr Fitch Rd, West Dover, VT 05356

/14
Not Listed For Sale

5 Lahar Rd, Marlboro, VT 05351
5 Lahar Rd, Marlboro, VT 05351

Last Sold Summary
- 9 Days On Market
Last Sold Price $140,000

Last Listing Agent Jamie Watson BHG Masiello Keene

/11
$495,000 Under Contract
- Land
- 68.89 Acres
- $7,185 per Acre
0 W Hill Rd, Jamaica, VT 05343

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 4 is 68.89 acres and is the largest of the five parcels for sale. This lot has a solid woods

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/11
$1,700 per month
- 1 Bed
- 1 Bath
- 300 Sq Ft
- Apartment for Rent
4 Elliot St Unit 2, Brattleboro, VT 05301

Corner apartment in downtown Brattleboro in the National is located on the corner of Elliot and Main Street. This one-bedroom apartment is in a secure building, laundry facilities on site, with parking down the street in the parking garage. Pets are welcome with an extra pet fee.

Peggy Winchester ACORN REAL ESTATE GROUP LLC

4 Elliot St Unit 2, Brattleboro, VT 05301
/10
$82,000 Sold Jan 07, 2026

0 Old Ledge Rd Unit 4950217, Westminster, VT 05346
- Land
- 5 Acres
- $16,400 per Acre
Last Sold Summary
- 9% Below List Price
- 928 Days On Market
Last Listing Agent Christine Lewis Brattleboro Area Realty

0 Old Ledge Rd Unit 4950217, Westminster, VT 05346

/36
Est $517,071 Not Listed For Sale

208 Shady Ln, West Wardsboro, VT 05360
- 3 Beds
- 2.5 Baths
- 2,050 Sq Ft
- Built 2006
208 Shady Ln, West Wardsboro, VT 05360

Last Sold Summary
- 5% Below List Price
- $265/SF
- 5 Days On Market
Last Sold Price $542,500

Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

/12
$999,000
- Land
- 12.2 Acres
- $81,885 per Acre
Higley Hill Rd, Wilmington, VT 05363

Looking for Vermont land with privacy, natural beauty, and development potential? This 12.2-acre parcel in Windham County offers a peaceful escape tucked into the woods, ideal for buyers seeking recreational land, a homestead site, or a rural retreat. With 250 ft of road frontage on Higley Hill Rd, the property is easily accessible while still offering seclusion.The terrain is wooded and

Community Lands Community Lands

Higley Hill Rd, Wilmington, VT 05363
/33
$1,600 per month
- 2 Beds
- 1 Bath
- 1,250 Sq Ft
- Condo for Rent
92 Prospect St Unit 1, Brattleboro, VT 05301

Close to downtown Brattleboro.2 bedroom, beautiful wood floors, Covered porch, pantry, non-working fireplace, 2 parking spaces.Heat, Hot Water, Dumpster on site, Plowing included in rent. Tenants pay all utilities - Electricity/Cable/Internet.$1600/month - First and security deposit required.

92 Prospect St Unit 1, Brattleboro, VT 05301
/46
$480,000 Sold Oct 28, 2025

28 Dover Green Rd, Dover, VT 05356
- 4 Beds
- 2 Baths
- 2,092 Sq Ft
- Built 1975
Last Sold Summary
- 4% Below List Price
- $229/SF
- 29 Days On Market
Current Estimated Value $475,505

Last Listing Agent Kim Meeker Southern Vermont Realty Group

28 Dover Green Rd, Dover, VT 05356

/40
Not Listed For Sale

965 Western Ave, Brattleboro, VT 05301
- 4 Beds
- 3 Baths
- 2,358 Sq Ft
- Built 1840
965 Western Ave, Brattleboro, VT 05301

Last Sold Summary
- $157/SF
- 55 Days On Market
Last Sold Price $370,000

Last Listing Agent Kate Barry EXP Realty

/7
$195,000 Under Contract
- Land
- 15.27 Acres
- $12,770 per Acre
0 W Hill Rd, Jamaica, VT 05343

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 2 is 15.27 acres and is the first parcel found on the left side of the newly built 20 foot

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/11
$1,550 per month
- 1 Bed
- 1 Bath
- 524 Sq Ft
- House for Rent
722 Vermont 30, Townshend, VT 05353

Single Family home located in Townshend, newly renovated with fresh paint and flooring. All rooms have natural light and plenty of windows to enjoy the nature right outside the window. This home has a large private yard, just minutes from shopping.

Peggy Winchester ACORN REAL ESTATE GROUP LLC

722 Vermont 30, Townshend, VT 05353
/60
$535,000 Sold Jun 20, 2025

78 Pond Loop Unit M-2, Wilmington, VT 05363
- 5 Beds
- 2.5 Baths
- 2,800 Sq Ft
- Built 1968
Last Sold Summary
- 8% Below List Price
- $191/SF
- 200 Days On Market
Current Estimated Value $578,368

Last Listing Agent Sigrid Pickering Chimney Hill Realty

78 Pond Loop Unit M-2, Wilmington, VT 05363

/24
Not Listed For Sale

30 Styles Branch Rd Unit 307, Stratton, VT 05360
- 4 Beds
- 3.5 Baths
- 1,178 Sq Ft
- Built 1979
30 Styles Branch Rd Unit 307, Stratton, VT 05360

Last Sold Summary
- $581/SF
- 7 Days On Market
Last Sold Price $685,000

Last Listing Agent Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

/15
$650,000 Under Contract
- Land
- 51.93 Acres
- $12,517 per Acre
0 W Hill Rd, Jamaica, VT 05343

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very unique, and

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/21
$2,100 per month
- 2 Beds
- 1.5 Baths
- 1,100 Sq Ft
- Condo for Rent
238 Fairview St Unit 238 Fairview Street, Brattleboro, VT 05301

This is a completely renovated three story furnished duplex built in 1932 with a renter on the other side. The renovation included removing the traditional kitchen and dining room, opening up the first floor space to include a galley kitchen with a marble island, a cozy sitting area with a propane stove, a half bath, and a comfortable living room space. The second floor has a small laundry room,

238 Fairview St Unit 238 Fairview Street, Brattleboro, VT 05301
/22
$69,000 Sold Oct 03, 2025

1051 Maple Hill Ln, Whitingham, VT 05342
- Land
- 10.01 Acres
- $6,893 per Acre
Last Sold Summary
- 3 Days On Market
Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

1051 Maple Hill Ln, Whitingham, VT 05342

/17
Est $478,725 Not Listed For Sale

38 Summit Meadows Cir, Dover, VT 05356
- 4 Beds
- 3 Baths
- 1,309 Sq Ft
- Built 1984
38 Summit Meadows Cir, Dover, VT 05356

Last Sold Summary
- 1% Above List Price
- $363/SF
- 12 Days On Market
Last Sold Price $475,000

Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

/26
$599,000
- 4 Beds
- 3 Baths
- 2,600 Sq Ft
10 Grouse Ln Unit 10A, Dover, VT 05356

Owners open to offers! Stunning Post and Beam style townhome overlooking spectacular views of Mount Snow and Haystack ski trails with the sunsets in the west beyond. This private end unit features an amenity rich location thanks to direct VAST snowmobile trail access, hiking and biking trails in the summer, as well as easy access to the Mount Snow golf course which is directly through the

Adam Palmiter Berkley & Veller Greenwood/Dover

10 Grouse Ln Unit 10A, Dover, VT 05356
/6
$1,700 per month
- 2 Beds
- 1 Bath
- 671 Sq Ft
- Apartment for Rent
1889 Vermont 30 Unit 1, Townshend, VT 05353

First Floor 2 bedroom apartment with natural light, close to town and is available now. Off street parking and a yard make the location ideal. Apartment is not furnished

Peggy Winchester ACORN REAL ESTATE GROUP LLC

1889 Vermont 30 Unit 1, Townshend, VT 05353
/29
$21,000 Sold Sep 26, 2025

282Qtr.4 89 Grand Summit Way, Dover, VT 05356
- 1 Bath
- 332 Sq Ft
- Built 1998
Last Sold Summary
- 7% Below List Price
- $63/SF
- 40 Days On Market
Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

282Qtr.4 89 Grand Summit Way, Dover, VT 05356

/30
Est $608,493 Not Listed For Sale

79 Wilmington Heights, Wilmington, VT 05363
- 4 Beds
- 3 Baths
- 2,200 Sq Ft
- Built 1987
79 Wilmington Heights, Wilmington, VT 05363

Last Sold Summary
- 9% Below List Price
- $305/SF
- 97 Days On Market
Last Sold Price $670,000

Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

/58
$425,000 Under Contract
- 2 Beds
- 2 Baths
- 1,012 Sq Ft
34 Snow Tree Ln Unit K, West Dover, VT 05356

Brand new, thoughtfully renovated and offering arguably the most direct, front-facing views of Mount Snow in the Snowtree community, this exceptional two-bedroom, two-bath condominium sits right at the base of the resort with true mountain presence from nearly every angle. Unlike many units with partial or filtered views, this residence enjoys unobstructed views straight up the slopes, watch

Erica Reynolds Southern Vermont Realty Group

34 Snow Tree Ln Unit K, West Dover, VT 05356
/4
$1,950 per month
- 2 Beds
- 1 Bath
- 1,000 Sq Ft
- Townhouse for Rent
995 Western Ave Unit 100, Brattleboro, VT 05301

This 2-bedroom apartment is just being renovated and is freshly painted. Amenities include an eat-in kitchen, new dishwasher and refrigerator, pantry, new or refinished flooring throughout, new bathroom, new windows, large screened porch, 1/2 garage plus parking for a second car in the driveway, separate entrance, and a large backyard with room to garden. Mowing, snow removal and heat are

995 Western Ave Unit 100, Brattleboro, VT 05301
/36
$625,000 Sold Aug 20, 2025

31 Joan's Ridge Rd, West Dover, VT 05356
- 5 Beds
- 3 Baths
- 2,223 Sq Ft
- Built 2012
Last Sold Summary
- 4% Below List Price
- $281/SF
- 126 Days On Market
Current Estimated Value $684,317

Last Listing Agent Jennifer Hovey-Densmore Deerfield Valley Real Estate

31 Joan's Ridge Rd, West Dover, VT 05356

/30
Not Listed For Sale

30 Styles Branch Rd Unit 309, Stratton, VT 05360
- 5 Beds
- 4 Baths
- 2,088 Sq Ft
- Built 1979
30 Styles Branch Rd Unit 309, Stratton, VT 05360

Last Sold Summary
- $244/SF
- 9 Days On Market
Last Sold Price $510,000

Last Listing Agent Stephen Coombs Stratton Real Estate

/51
$585,000
- 3 Beds
- 2 Baths
- 1,814 Sq Ft
1886 Winhall Hollow Rd, South Londonderry, VT 05155

Exceptional property tucked amidst nature with views toward Magic. Whether you're a weekend warrior looking to enjoy everything the Green Mountains have to offer or looking for a year round residence with great schools, this property offers an optimal location- convenient to Stratton, Bromley and Magic Mountains as well as Burr and Burton Academy and Floodbrook School. Gourmet kitchen with gas

Kim Morgan-Wohler Wohler Realty Group

1886 Winhall Hollow Rd, South Londonderry, VT 05155
/8
$1,700 per month
- 1 Bed
- 1 Bath
- 400 Sq Ft
- Apartment for Rent
4 Elliot St Unit 3, Brattleboro, VT 05301

The National, featuring this 1 Bedroom apartment with bright sunlit rooms, amazing hardwood floors and views of downtown. Coin operated Laundry is on site and off-street parking is available in the parking garage. The building is pet friendly

Peggy Winchester ACORN REAL ESTATE GROUP LLC

4 Elliot St Unit 3, Brattleboro, VT 05301
/36
$230,000 Sold Apr 23, 2025

1457 Rockingham Rd, Town of Rockingham, VT 05101
- 4 Beds
- 1 Bath
- 1,600 Sq Ft
- Built 1825
Last Sold Summary
- 49% Below List Price
- $144/SF
- 329 Days On Market
Current Estimated Value $259,820

Last Listing Agent Glenn Olney Barrett and Valley Associates Inc.

1457 Rockingham Rd, Town of Rockingham, VT 05101

/26
Not Listed For Sale

1 Wildwood Dr, West Brattleboro, VT 05301
- 2 Beds
- 1 Bath
- 962 Sq Ft
- Built 1977
1 Wildwood Dr, West Brattleboro, VT 05301

Last Sold Summary
- $82/SF
- 12 Days On Market
Last Sold Price $79,000

Last Listing Agent Victoria Woods Brattleboro Area Realty

Showing Results 41 - 80, Page 2 of 18

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