Windham County VT Homes for Sale

/33
$319,000
- 3 Beds
- 2 Baths
- 1,310 Sq Ft
1829 W Jamaica Rd, Jamaica, VT 05343

Vermont Charming! Tucked away along a peaceful river in Jamaica, Vermont this charming cape offers the perfect blend of privacy, character and convenience just 4 miles from Stratton Mountain Resort. With three bedrooms and one and three quarters baths, the home has been thoughtfully maintained and updated while preserving its classic New England charm. Recent upgrades to the kitchen and bathrooms

Alison Cummings

Cummings & Co

(802) 471-3958

1829 W Jamaica Rd, Jamaica, VT 05343
/31
$359,000
- 3 Beds
- 1.5 Baths
- 1,152 Sq Ft
410 Tallwood Cir, Londonderry, VT 05148

This cute Sherwood Forest house is ready for the next owners! Nicely renovated over the past several years, this 3 bedroom, 1 and a half bath chalet is located in the heart of Vermont ski country. In between Londonderry and Bromley, minutes from Manchester or Stratton and Magic ,this central location allows for access to all that makes Vermont special! Enjoy the open living area after a day of

Alison Cummings

Cummings & Co

(802) 392-0721

410 Tallwood Cir, Londonderry, VT 05148
/60
$4,950,000
- 4 Beds
- 8 Baths
- 16,736 Sq Ft
1950 Collins Rd, Brattleboro, VT 05301

Exceptional 177+ Acre Estate with Luxury Log Home, Event Venue & Craft Beverage Facilities. Experience unmatched luxury and opportunity on this remarkable 177+ acre estate. Featuring an 8,000+ sq ft timber frame log home, a 7,100 sq ft finished event venue, and on-site winery, craft brewery, and champagne-making facilities, this turn-key property is ideal as a private residence, retreat, or

Margretta Fischer

Wohler Realty Group

(802) 317-7158

1950 Collins Rd, Brattleboro, VT 05301
/60
$849,000
- 5 Beds
- 4.5 Baths
- 3,840 Sq Ft
42 Blackberry Ln, Jamaica, VT 05343

Welcome to "Sweet Berry Farm", a charming Vermont homestead blending 1850s character with a spacious modern addition. Set on 5.7 private acres in Jamaica, this property offers abundant natural beauty—mature apple trees, blueberry and blackberry bushes and vibrant seasonal gardens. The expanded farmhouse provides exceptional space for living and entertaining. The main floor features an open living

MaryKate Grey Stratton Real Estate

42 Blackberry Ln, Jamaica, VT 05343
/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
/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
/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
/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
/51
$550,000
- 3 Beds
- 2 Baths
- 1,814 Sq Ft
1886 Winhall Hollow Rd, South Londonderry, VT 05155

Optimal Location, Competitively priced, Exceptional property tucked amidst nature with views toward Magic. Offering Main Residence and a large oversized detached garage/ barn with upstairs finished space and plenty of space for snow mobiles, ATVs and all your mountain vehicles and outdoor toys. Whether you're a weekend warrior looking to enjoy everything the Green Mountains have to offer or

Kim Morgan-Wohler Wohler Realty Group

1886 Winhall Hollow Rd, South Londonderry, VT 05155
/41
$899,000
- 4 Beds
- 4 Baths
- 3,200 Sq Ft
9 Windham Way, Dover, VT 05356

This upgraded new style Greenspring townhome has direct views of Mount Snow and door to door shuttle service to and from the unit and the base area. A well updated 4+ bedroom, 4 bath unit with lots of bonus space, many recent updates and unique features. These include an open concept great room with vaulted ceiling, sunny exposure and sunset/ski trail views, wood burning fireplace unique against

Adam Palmiter Berkley & Veller Greenwood/Dover

9 Windham Way, Dover, VT 05356
/35
$899,900
- 4 Beds
- 3.5 Baths
- 2,272 Sq Ft
12 Encore Place, Dover, VT 05356

Mountain Modern Living with unmatched ski views of Mount Snow. Discover the perfect blend of luxury and nature in this 3 year young contemporary home ideally situated to capture breathtaking unobstructed views of Carinthia. This thoughtfully designed 4 bedroom home offers an open concept floor plan while still offering privacy and cozy spaces that highlight the beauty of the alpine landscape.

Heidi Zizza Four Seasons Sotheby's Int'l Realty

12 Encore Place, Dover, VT 05356
/37
$690,000
- 5 Beds
- 3 Baths
- 2,635 Sq Ft
341 Under the Mountain Rd, Londonderry, VT 05148

Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly

Andy Reed Four Seasons Sotheby's Int'l Realty

341 Under the Mountain Rd, Londonderry, VT 05148
/54
$695,000
- 6 Beds
- 3 Baths
- 2,740 Sq Ft
1161 Little Pond Rd, Londonderry, VT 05148

Set along a quintessential Vermont country road just moments from the pristine waters of Lowell Lake, this versatile property offers the rare opportunity to enjoy peaceful rural living with flexible multi-family potential. Surrounded by natural beauty and year-round recreation, the setting is both private and convenient to all that Londonderry has to offer. The home features approximately 2,700

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

1161 Little Pond Rd, Londonderry, VT 05148
/60
$650,000
- 4 Beds
- 4 Baths
- 2,978 Sq Ft
23 Brook Rd, Saxtons River, VT 05154

Includes 1-Year Home Warranty. A Distinctive Country Retreat on 6.8± private acres in the heart of the historic village of Saxtons River. This idyllic country estate offers year-round views, exquisite perennial gardens, & two beautifully integrated wings—the timeless Cape & the charming Carriage House. Inside of the Cape wing is a sunlit eat-in kitchen, KraftMaid cherry cabinetry & Silestone

Isabella Luhrs BHG Masiello Keene

23 Brook Rd, Saxtons River, VT 05154
/60
$795,000
- 4 Beds
- 3.5 Baths
- 3,212 Sq Ft
104 Juniper Ridge Rd, Brattleboro, VT 05301

Welcome to Juniper Ridge! Where you will find superior craftsmanship, a private haven, and neighbors only one can dream of. As you enter the foyer of this custom built home, you'll feel its character & elegance with vaulted ceilings, arched doorways, terracotta tile and balconies lined with bookshelves. The home was built with attention to the flow, energy and natural light. The kitchen has

Kristen Ziter Taylor Brattleboro Area Realty

104 Juniper Ridge Rd, Brattleboro, VT 05301
/60
$549,000
- 2 Beds
- 2 Baths
- 850 Sq Ft
794 White Rd, Windham, VT 05359

Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out—new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam

Erica Reynolds Southern Vermont Realty Group

794 White Rd, Windham, VT 05359
/46
$625,000
- 5 Beds
- 3.5 Baths
- 2,520 Sq Ft
143 Hillwinds Rd, Brattleboro, VT 05301

Welcome to Hillwinds and this lovely colonial. With 200 acres of conserved land and trails behind and a wonderful meadow view in the front, this house truly feels a part of the landscape. The main house has four bedrooms and two and a half baths and invites you to step right into your new life in this well cared for and lovingly maintained home. The gardens are in, the drive paved and the garden

Christine Lewis Brattleboro Area Realty

143 Hillwinds Rd, Brattleboro, VT 05301
/31
$619,000
- 4 Beds
- 4 Baths
- 3,354 Sq Ft
556 Sawmill Rd, Wardsboro, VT 05355

Set on a private one-acre lot in Wardsboro, this well-designed 4-bedroom, 4-bathroom home with an attached garage offers over 3,000 square feet of living space and the perfect blend of comfort, style, and refined Vermont living. Ideally located just 12 minutes from Mount Snow and 20 minutes from Stratton Mountain Resort, the property is perfectly positioned for year-round enjoyment — from winter

Kim Meeker Southern Vermont Realty Group

556 Sawmill Rd, Wardsboro, VT 05355
/30
$698,000
- 4 Beds
- 3 Baths
- 2,600 Sq Ft
10 Grouse Ln, Dover, VT 05356

Welcome to your perfect Vermont getaway! This spacious 4 bedroom, 3 bathroom townhome is ideally located adjacent to the Mount Snow Golf Course, offering year-round enjoyment. Just a short drive to both Mount Snow and The Hermitage Club, you'll have easy access skiing, golfing, dining, and all that Southern Vermont has to offer.Step inside to find a warm and inviting interior, highlighted by

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

10 Grouse Ln, Dover, VT 05356
/55
$525,000
- 3 Beds
- 2 Baths
- 1,888 Sq Ft
57 Oak Ln, Jamaica, VT 05343

This charming saltbox home, built in 1980, features three bedrooms and two bathrooms, complemented by a dining room that invites abundant sunlight. The spacious living room and family room, equipped with a wood stove, create a warm and inviting atmosphere. The large kitchen offers ample space for culinary endeavors, while the full unfinished basement presents opportunities for customization. Set

Mike England Michael England Real Estate

57 Oak Ln, Jamaica, VT 05343
/43
$625,000
- 5 Beds
- 3 Baths
- 2,600 Sq Ft
15 Bills Rd, West Wardsboro, VT 05360

This spacious five-bedroom, three-bath Cape-style home offers a wonderful Vermont retreat, ideally located just minutes from the Stratton Mountain Resort Sun Bowl and the scenic Grout Pond Recreation Area, and only about 10 minutes from Mount Snow Resort. With immediate access to nearby snowmobile trails, it’s perfectly suited for year-round outdoor enthusiasts. Nicely landscaped yard with

Jennifer Hovey-Densmore Deerfield Valley Real Estate

15 Bills Rd, West Wardsboro, VT 05360
/50
$565,000
- 3 Beds
- 2 Baths
- 1,944 Sq Ft
3148 Route 11, Londonderry, VT 05148

Looking for a piece of Vermont to call your own? Look no further then this beautiful home looking for new owners to love and enjoy it like the current owners have. Perfectly situated in Londonderry, Vermont near Bromley, Stratton, Okemo, and Magic Mountains. The sellers have done updates to the home and property but have left spots for the new owners to still put their own finishing touches on

Erin Kendall EXP Realty

3148 Route 11, Londonderry, VT 05148
/41
$539,000
- 4 Beds
- 3 Baths
- 2,948 Sq Ft
196 Powder Mill Rd, Londonderry, VT 05148

Mountain Escape with Multi-Generational Potential in Powder Mill Welcome to your mountain retreat in the heart of Vermont’s ski country! This spacious home in the desirable Powder Mill community has been thoughtfully updated with brand new kitchen cabinets, gleaming granite countertops, stainless steel appliances, and fresh carpet and flooring throughout. The flexible layout offers room for

Katie Ladue Gilbert BHHS Verani Upper Valley

196 Powder Mill Rd, Londonderry, VT 05148
/26
$579,000
- 3 Beds
- 2 Baths
- 2,360 Sq Ft
68 Ellis Brook Rd, Dover, VT 05341

Gorgeous updated chalet on a private 2-acre parcel with mountain views and easy access to Mount Snow. Nestled in the desirable Dover Hills, this charming country retreat offers privacy befitting a year-round getaway, yet is just a short drive to the Mount Snow ski resort. Ample parking off a paved road, generous lawn space for play or pets, a garden shed, and excellent sun exposure complete the

Adam Palmiter Berkley & Veller Greenwood/Dover

68 Ellis Brook Rd, Dover, VT 05341
/60
$599,000
- 5 Beds
- 2.5 Baths
- 3,000 Sq Ft
673 Vermont 121, Grafton, VT 05146

Historic Charmer, this c. 1830 farmhouse has been loved and stewarded by its current owners for half a century. It is time to pass this amazing vintage home on to another lucky family. The house has original features including 2 fireplaces, curved plaster walls and beautiful honey colored wide pine floors. The first floor offers an eat-in- kitchen, formal dining room, spacious sunny living room

Janet Lucier Barrett & Valley Assoc. Inc

673 Vermont 121, Grafton, VT 05146
/29
$649,000
- 4 Beds
- 2 Baths
- 2,000 Sq Ft
152 Main St, Grafton, VT 05146

Newly renovated home located in the heart of Grafton Village! This home features 4 spacious bedrooms, and 2 full baths. Large primary bedroom suite located on the first floor of the home with working fireplace and private bathroom. Brand new kitchen with all new cabinetry, quartz countertops and stainless steel appliances. Original hardwood floors, moldings and original doors. All brand new

Derek Greene Derek Greene

152 Main St, Grafton, VT 05146
/35
$599,000
- 4 Beds
- 3 Baths
- 2,775 Sq Ft
4448 Route 100, Wardsboro, VT 05355

This four-bedroom, three-bathroom home with additional office or bonus room space can be yours! Offering a spacious family room with fireplace, a cozy den off the garage entry. A formal dining room in addition to kitchen that allows for another sitting area with plenty of wall space to decorate. The location is set back off Route 100, so very minimal road noise yet the highway is always

Julie Lowe Lowe's Real Estate, LLC

4448 Route 100, Wardsboro, VT 05355
/39
$575,000
- 3 Beds
- 2 Baths
- 1,957 Sq Ft
256 Potter Rd, Wardsboro, VT 05355

Built with a decade of love and care, this custom 3-bedroom, 2-bath hybrid timber frame home showcases quality craftsmanship and a deep connection to nature. Designed with natural materials to harmonize with the surrounding landscape, this inviting home offers peace and comfort both inside and out. Fall asleep to the soothing sound of the river that flows the length of the property. The main

Jennifer Hovey-Densmore Deerfield Valley Real Estate

256 Potter Rd, Wardsboro, VT 05355
/32
$559,000
- 3 Beds
- 3 Baths
- 2,080 Sq Ft
9 Greer Ct, Wilmington, VT 05363

Charming 2007 home with recent renovations nestled in the Chimney Hill community just a short drive from the Mount Snow ski resort, country village of Wilmington, and nearby lakes and amenities. This home sits on a private dead end parcel and has unique privacy and curb appeal. Inside you are treated to a large vaulted great room with expansive windows, exposed natural wood ceilings, and great

Adam Palmiter Berkley & Veller Greenwood/Dover

9 Greer Ct, Wilmington, VT 05363
/60
$549,000
- 2 Beds
- 2 Baths
- 2,016 Sq Ft
35 Upper Bartonsville Rd, Chester, VT 05143

Looking for a turn key Vermont retreat to call your own? This beautiful home built in 2009 and complete with a newer barn, chicken coop, treehouse, and storage shed could be what you have been dreaming of. Conveniently located just a short drive to 91, not far to the Vast trail access for snowmobiling, and near to many Vermont mountains for skiing or snowboarding. The warm and welcoming home

Erin Kendall EXP Realty

35 Upper Bartonsville Rd, Chester, VT 05143
/48
$644,000
- 3 Beds
- 2.5 Baths
- 2,329 Sq Ft
774 Stratton Arlington Rd, Stratton, VT 05360

Charming Log Cabin Compound Near Stratton and Mount SnowEscape to this quintessential Vermont retreat nestled on 1.2 private acres just minutes from Grout Pond, the Green Mountain National Forest, and a short drive to both Stratton and Mount Snow Resorts.The main log home offers three bedrooms and two baths with a warm, inviting open-concept living space. A stone fireplace anchors the

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

774 Stratton Arlington Rd, Stratton, VT 05360
/40
$525,000
- 3 Beds
- 2 Baths
- 1,977 Sq Ft
1355 Whitneyville Rd, Halifax, VT 05301

Welcome to this charming country log home set on 30.6 private acres at the peaceful end of the road. Thoughtfully positioned to capture its surroundings, the home sits just high enough to enjoy pleasant views and beautiful mountain sunsets, best experienced from the inviting covered porches and open deck. Inside, the open-concept main level features abundant windows and cathedral ceiling creating

Leslie Fraser Four Seasons Sotheby's Int'l Realty

1355 Whitneyville Rd, Halifax, VT 05301
/21
$489,000
- 3 Beds
- 2 Baths
- 2,003 Sq Ft
12 Lilla Ln, Wilmington, VT 05363

Beautiful woodsy contemporary chalet located just down from the Chimney Hill Clubhouse in Wilmington. This charming home has nearby access to the country village of Wilmington, Lake Whitingham, is a short drive to the Mt Snow ski resort, and has nearby to one of the best hiking areas in Southern Vermont, thanks to the community adjacent Green Mountain National Forest. It sits nestled on a private

Adam Palmiter Berkley & Veller Greenwood/Dover

12 Lilla Ln, Wilmington, VT 05363
/31
$1,750,000
- 4 Beds
- 3.5 Baths
- 2,698 Sq Ft
148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360

148B Sun Bowl Ridge Rd., Stratton Mountain, VT 05155, Solstice 148B Ski in, ski out directly from your private garage on a Stratton ski trail that has full snowmaking coverage. This home is in one of the most exclusive trailside communities in all of the Northeast! It has an open and sunny floorplan with large windows and a sliding glass door to the private patio with fire pit and hot tub.

Andrew King Stratton Real Estate

148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360
/15
$67,500
- Land
- 3.5 Acres
- $19,286 per Acre
0 Dover Rd Unit 5054979, Newfane, VT 05345

Welcome to your future home in the heart of a picturesque Vermont village! These exquisite land lots, thoughtfully designed by the architect-owner, offer a unique opportunity to build your dream home in a setting that perfectly captures the quintessential charm of small-town Vermont. Each lot is meticulously planned to adhere to the timeless "Vermont Vernacular" style, ensuring that your new home

Keith Nowak Four Seasons Sotheby's Int'l Realty

0 Dover Rd Unit 5054979, Newfane, VT 05345
/30
$749,000
- Land
- 2.57 Acres
- $291,440 per Acre
Lot 3 Old Mill Ln, Wilmington, VT 05363

Bring your own builder and discover an exceptional opportunity to own a 2.57 acre parcel of land located in an exclusive private neighborhood adjacent to the renowned private ski resort, The Hermitage Club in Wilmington, Vermont. This premium lot is the perfect canvas for creating your dream mountain retreat with custom homes to be crafted by your own builder or the Wadsworth Design Build. Enjoy

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

Lot 3 Old Mill Ln, Wilmington, VT 05363
/22
$539,000
- Land
- 2.88 Acres
- $187,153 per Acre
309 Vermont Route 100, Dover, VT 05356

Prime Investment Opportunity – Near Mount Snow Ski Resort!An exceptional development opportunity awaits just half a mile from Mount Snow Ski Resort. This level lot with stunning mountain views is ideally situated close to all area recreation – skiing, snowboarding, hiking, biking, and more.Plans for 8 units / 24 bedroomsTown sewer availableMost permits secured – only waiting on

Rich Caplan Deerfield Valley Real Estate

309 Vermont Route 100, Dover, VT 05356
/20
$995,000
- 3 Beds
- 3.5 Baths
- 1,800 Sq Ft
56 Shattarack Rd Unit D6, Stratton, VT 05360

Rare opportunity to own an exceptional ski-out/ski-back Slopeside unit at Stratton. This newly renovated 3-bedroom plus loft, 3.5-bathroom townhome offers spacious accommodations in a prime location that is both private and highly convenient. The expanded kitchen features elegant stone countertops and stainless steel appliances, perfect for both everyday meals and entertaining. The wood-burning

Kim Morgan-Wohler Wohler Realty Group

56 Shattarack Rd Unit D6, Stratton, VT 05360
/5
$139,000
- Land
- 8.52 Acres
- $16,315 per Acre
0 Higley Hill, Dover, VT 05356

Fantastic eastern views of New Hampshire mountains & valleys. A roadway, power & phone already exists for 4 dramatic view lots. Pick the one you want! Family & friends will enjoy ski area resort & local amenities nearby, while Brattleboro & CT River Valley resources are just down the hill. Truly majestic sites! Package lot offers considered. Appointment is required to walk the property.

Michael Purcell Berkley & Veller Greenwood/Dover

0 Higley Hill, Dover, VT 05356
/2
$89,900
- 4 Beds
- 2 Baths
- 1,902 Sq Ft
203 Smith Rd, Jamaica, VT 05343

Looking for a project? Featuring a drilled well, existing septic, electric, and driveway, you have a good start for a new build, renovation or a combination of the two. The cabin has been added onto many times, making room for a growing family. The land is mostly level, with some nice plantings and the house sits back a little distance from the neighbors. The well is being shared, electric is run

Christine Lewis Brattleboro Area Realty

203 Smith Rd, Jamaica, VT 05343

Showing Results 1 - 40, Page 1 of 9

Vermont Windham County

How to Buy a Home How to Finance a Home How to Sell a Home

Windham County Types of Homes for Sale

Windham County Real Estate Listings

More About Living in Windham County

Homes for Sale in Nearby Zip Codes

Homes for Sale in Nearby Cities

Homes for Sale in Nearby Counties

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage