Windham County VT Homes for Sale

/56
$350,000
- 6 Beds
- 4.5 Baths
- 3,042 Sq Ft
2072 N Main St, Londonderry, VT 05148

Rare Mixed-Use Opportunity in Downtown Londonderry, VT – Live, Work, or Invest! Unlock the full potential of this versatile and beautifully situated property in the heart of Londonderry’s vibrant downtown district. With major West River frontage, expansive lawn space, and prime visibility on North Main Street, this unique listing offers endless possibilities — perfect for residential, commercial,

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 441-6058

2072 N Main St, Londonderry, VT 05148
/10
$185,000
- Land
- 8 Acres
- $23,125 per Acre
4441 Vt Route 30, Jamaica, VT 05343

Discover the potential of this serene and wooded 8.0± acre parcel, offering a peaceful setting and natural beauty just minutes from the heart of Jamaica Village. Currently being subdivided from a larger tract, the lot features a 5 Bedroom Wastewater Permit pending state approval and a survey in progress to finalize boundaries—laying the foundation for your future plans. An existing electric

Trent Stephens

Wohler Realty Group

(802) 808-6056

4441 Vt Route 30, Jamaica, VT 05343
/14
$120,000
- Land
- 2.07 Acres
- $57,971 per Acre
191 Pingree Park Ln, Londonderry, VT 05148

Discover this hidden gem in Londonderry. River frontage on pristine Utley Brook with headwaters flowing from the Green Mountain National Forest create a serene setting minutes from downtown. Full time residence or vacation home, you choose! Ready to build. Completely engineered- State and Town permits for a 4 bedroom home in place including septic permits, well and house placement, updated

Alison Cummings

Cummings & Co

(802) 848-6904

191 Pingree Park Ln, Londonderry, VT 05148
/18
$130,000
- Land
- 2.19 Acres
- $59,361 per Acre
192 Pingree Park Ln, Londonderry, VT 05148

Discover this hidden gem in Londonderry. River frontage on pristine Utley Brook with headwaters flowing from the Green Mountain National Forest create a serene setting minutes from downtown. Full time residence or vacation home, you choose! Ready to build. Completely engineered- State and Town permits for a 4 bedroom home in place including septic permits, well and house placement, updated

Alison Cummings

Cummings & Co

(802) 444-8158

192 Pingree Park Ln, Londonderry, VT 05148
/37
$395,000
- 4 Beds
- 2 Baths
- 2,400 Sq Ft
3298 Houghtonville Rd, Grafton, VT 05146

Classic 1800s Farmhouse in Charming Grafton, VermontLocated in Houghtonville, a beautiful part of historic Grafton, this mid-19th century farmhouse offers a rare opportunity to restore and reimagine a true Vermont original. With strong bones and timeless character, the home features wide plank floors, vintage woodwork, and a traditional layout that reflects its heritage. Typical of this

Alison Cummings

Cummings & Co

(802) 317-7411

3298 Houghtonville Rd, Grafton, VT 05146
/60
$620,000
- 3 Beds
- 2 Baths
- 2,700 Sq Ft
121 Dover Hill Rd, Dover, VT 05341

Price reduced! Discover this Vermont countryside retreat offering an unbeatable blend of equestrian haven, homestead, and ski getaway, all on 5 private acres in desirable Dover. Enjoy perennial gardens bursting with color, abundant raspberry canes, and asparagus beds for beauty and bounty year-round. Step inside to vaulted ceilings, hardwood floors, and custom inlay bookshelves that add warmth

Nick Sicard EXP Realty

121 Dover Hill Rd, Dover, VT 05341
/41
$8,950,000
- 6 Beds
- 10 Baths
- 13,393 Sq Ft
370 Fischer Ln, Jamaica, VT 05343

Accessible, but miles from the everyday. Camp Endo’s mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark

Dia Jenks LandVest, Inc/Woodstock

370 Fischer Ln, Jamaica, VT 05343
/46
$210,000
- Land
- 30 Acres
- $6,977 per Acre
184 Schoolhouse Rd, Jamaica, VT 05343

Jamaica, Vermont’s hidden gem! Experience this wonderful 30.1+/- acre forested parcel with views of the local mountains. The land gently slopes to the southeast, perfect for solar, but better yet, utility lines are located along much of the frontage! Bounded on two sides by classic stone walls, there is a woods road that travels through the property making exploration easy. Jamaica has NO local

Curtis Trousdale Preferred Properties

184 Schoolhouse Rd, Jamaica, VT 05343
/15
$775,000
- Land
- 52 Acres
- $14,924 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

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/11
$595,000
- Land
- 69 Acres
- $8,637 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

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/8
$320,000
- Land
- 35 Acres
- $9,267 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

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/7
$235,000
- Land
- 15 Acres
- $15,390 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
/42
$829,000
- 5 Beds
- 2.5 Baths
- 3,102 Sq Ft
1410 Haven Hill Rd, South Londonderry, VT 05155

This beautiful Timber frame home on an 8.1 acre lot is located a few miles from the base of Stratton, Bromley, and Magic Mountain making it a versatile investment. Whether a seasonal prospect or primary home, being next door to Gale Meadow Pond provides a wonderful destination to walk, hike, fish, or just paddle. This home has a private, beautiful yard with its own pond, stream, and firepit just

Amy Carson Lowe's Real Estate, LLC

1410 Haven Hill Rd, South Londonderry, VT 05155
/40
$720,000
- 3 Beds
- 3.5 Baths
- 1,800 Sq Ft
134 Ellis Brook Rd, Dover, VT 05356

This stunningly renovated 3-bedroom, 3.5-bathroom vacation home with carport, completed in 2021, offers exceptional comfort and style in Dover Hills, near Mount Snow. The remodel includes a brand-new kitchen, bathrooms, flooring, and furniture throughout. Notable upgrades feature an additional 3/4 bathroom, a fully finished basement, and upgraded plumbing, electrical systems, and roof. Modern

Jennifer Hovey-Densmore Deerfield Valley Real Estate

134 Ellis Brook Rd, Dover, VT 05356
/31
$556,000
- 3 Beds
- 2 Baths
- 1,522 Sq Ft
174 Whites Hill Rd, Dover, VT 05356

Nestled amidst over 20 acres of pristine land, this Moosehead log home offers the perfect blend of privacy and breathtaking views. Imagine living without the burden of an electric bill, as this property is equipped with a complete solar power system and a backup generator, ensuring you have all the modern conveniences while embracing a sustainable lifestyle.Whether you're working remotely

Regina Perrotto Skihome Realty

174 Whites Hill Rd, Dover, VT 05356
/20
$525,000
- 3 Beds
- 2.5 Baths
- 1,120 Sq Ft
4 Sunnyside Rd, West Dover, VT 05356

Location, location, location! This beautifully renovated ski chalet sits just a mile south of the Mount Snow ski resort with public shuttle service to and from the mountain. The home is far more private than you would expect from the small lot size, but that means less to maintain, and more downtime, not upkeep. Thanks to great proximity to amenities you also can easily get to nearby restaurants,

Adam Palmiter Berkley & Veller Greenwood/Dover

4 Sunnyside Rd, West Dover, VT 05356
/33
$550,000
- 3 Beds
- 2 Baths
- 1,688 Sq Ft
19 Titus Farm Rd, Wilmington, VT 05363

The epitome of a Vermont country home, yet just outside the village of Wilmington, down the road from Lake Raponda, and a short drive the Mount Snow ski resort. This lovely 5+ acre property has a beautiful gurgling brook running through it, gorgeous stone work including old walls and an old stone bridge, trails through the pastoral setting, fire pit area, perennial gardens, and utter privacy.

Adam Palmiter Berkley & Veller Greenwood/Dover

19 Titus Farm Rd, Wilmington, VT 05363
/33
$995,000
- 3 Beds
- 2 Baths
- 1,620 Sq Ft
19 Village Lodge Rd Unit 407, Stratton, VT 05155

Rare opportunity to own in the heart of the Stratton Mountain Village! Come home to the Landmark community. Located attached to the iconic "Clocktower" at Stratton, Vermont. This homes boasts three spacious bedrooms and two full bathrooms with amazing mountain views and southern exposure. Enjoy the cozy gas burning fireplace after a hard day skiing or riding. Landmark provides ski lockers, an

Timothy Mich Doddridge Stratton Real Estate

19 Village Lodge Rd Unit 407, Stratton, VT 05155
/26
$529,000
- 4 Beds
- 2.5 Baths
- 1,864 Sq Ft
1966 Thompsonburg Rd, South Londonderry, VT 05155

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

Wilkie Bushby TPW Real Estate

1966 Thompsonburg Rd, South Londonderry, VT 05155
/37
$730,000
- 5 Beds
- 3 Baths
- 2,275 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
/60
$695,000
- 4 Beds
- 4 Baths
- 2,978 Sq Ft
23 Brook Rd, Saxtons River, VT 05154

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 quartz countertops —all overlooking

Isabella Luhrs BHG Masiello Keene

23 Brook Rd, Saxtons River, VT 05154
/30
$579,000
- 4 Beds
- 2 Baths
- 2,656 Sq Ft
204 Meeting House Ln, Brattleboro, VT 05301

Your Dream Home Awaits on Meetinghouse Lane! Nestled in the desirable and quiet neighborhood of Meetinghouse Lane, this contemporary home offers both privacy & charm. Surrounded by mature trees, the property feels like a peaceful retreat, while still being conveniently located. A paved driveway leads to an oversized two-car garage, connected to the house by a convenient breezeway. The expansive

Desiree Stango Berkley & Veller Greenwood Country

204 Meeting House Ln, Brattleboro, VT 05301
/60
$555,000
- 3 Beds
- 2 Baths
- 2,100 Sq Ft
22 Lower Howe's Rd Unit A89, Wilmington, VT 05363

Section A - end of the road, low on the Hill, this Chalet style home has a lot of desirable features you have been looking for, including a mudroom entry with custom live edge bench, ski, coat and storage racks, three levels of living space, view rail deck, fire pit, family room, laundry, bunk room and full bath on ground level, 2 bedrooms, a full bath and cathedral ceiling open concept living,

Sigrid Pickering Chimney Hill Realty

22 Lower Howe's Rd Unit A89, Wilmington, VT 05363
/25
$549,000
- 4 Beds
- 3 Baths
- 2,100 Sq Ft
30B Queen Anne's Way, Dover, VT 05356

Beautiful Kingswood townhome with direct snowmobile trail access and shuttle service to the Mount Snow ski resort. This unique 4 bedroom townhome is located towards the lower side of the development where each unit has more privacy. easy access to trails, and great parking. The unit features an open concept living space with vaulted ceiling, a wood burning fireplace, mounted tvs in the living

Adam Palmiter Berkley & Veller Greenwood/Dover

30B Queen Anne's Way, Dover, VT 05356
/41
$579,000
- 4 Beds
- 3 Baths
- 2,948 Sq Ft
196 Powder Mill Rd, Londonderry, VT 05148

Mountain Escape with Multi-Generational Potential in Powder MillWelcome 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

Katie Ladue Gilbert KW Vermont Woodstock

196 Powder Mill Rd, Londonderry, VT 05148
/35
$549,000
- 3 Beds
- 2 Baths
- 2,136 Sq Ft
8 Lilla Ln, Wilmington, VT 05363

Welcome to this beautifully updated 3-bedroom, 2-bathroom home nestled on a serene wooded lot in the Chimney Hill community. Set back from the road for added privacy, this home offers a perfect blend of comfort and style. As you step inside, a spacious two-room addition, currently used by the seasonal owners for additional sleeping, expands the living space to over 2,100 square feet. The

Patricia Fitzpatrick Skihome Realty

8 Lilla Ln, Wilmington, VT 05363
/41
$574,000
- 3 Beds
- 3 Baths
- 2,704 Sq Ft
4138 W Hill Rd S, Jamaica, VT 05343

This three-bedroom, three-bath custom-built log home is situated on 2.37 acres in a tranquil mountain setting just minutes from skiing. Built with double tongue-and-groove log construction, the cozy home provides the warm wood interior one would expect. The open-concept main level focuses on the fieldstone hearth, wood stove, and beautiful oak floors. A covered porch in the front of the home

Patricia Fitzpatrick Skihome Realty

4138 W Hill Rd S, Jamaica, VT 05343
/17
$625,000
- 4 Beds
- 2 Baths
- 1,900 Sq Ft
9 Cooper Hill Rd, Dover, VT 05341

Welcome to your own private sanctuary, tucked away on six stunning acres of unspoiled natural beauty. This inviting 4-bedroom, 2-bathroom home offers the perfect balance of rustic charm and modern comfort, creating an ideal retreat for those seeking peace, privacy, and outdoor adventure.Surrounded by lush woods and open space, the property features a serene private pond, the soothing sounds

Carrie Mathews Winhall Real Estate

9 Cooper Hill Rd, Dover, VT 05341
/35
$629,000
- 3 Beds
- 2.5 Baths
- 2,033 Sq Ft
64 Gleason Farm Ln, Jamaica, VT 05343

Nestled on nearly 2 flat acres, this beautifully maintained South-facing New England Cape Cod farmhouse is a rare find in the mountains. Located on a private dead-end road, the home offers peaceful seclusion while being just a short drive to Stratton Mountain for skiing and tubing in the winter and Jamaica State Park for hiking and stunning waterfalls in the warmer months. With only one owner,

Carrie Mathews Winhall Real Estate

64 Gleason Farm Ln, Jamaica, VT 05343
/39
$599,000
- 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
$549,000
- 3 Beds
- 2.5 Baths
- 2,000 Sq Ft
2B Queen Anne's Way Unit 2B, Dover, VT 05356

Beautiful Kingswood townhouse ideally located between Mount Snow and Hermitage Club at Haystack Mountain. This Kingswood townhouse offers the perfect mountain getaway. The open-concept living area features vaulted ceiling and a stunning three-sided wood-burning fireplace with custom stone surround and wood mantle creating a warm, inviting atmosphere. Enjoy the well-appointed kitchen with center

Monique White Deerfield Valley Real Estate

2B Queen Anne's Way Unit 2B, Dover, VT 05356
/29
$625,000
- 4 Beds
- 2 Baths
- 2,137 Sq Ft
72 Colonial Ridge Rd, Dover, VT 05356

This turnkey mountain retreat is ready for you to enjoy! Nestled in the serene Dover Hills, this home is ideally located near Mount Snow, snowmobile trails, shopping, and dining. Featuring four inviting bedrooms and a game room on the lower level, there’s plenty of space for everyone to relax. Cozy up in front of the wood-burning fireplace or breathe in the fresh mountain air while soaking in the

Michelle O'Neil Deerfield Valley Real Estate

72 Colonial Ridge Rd, Dover, VT 05356
/40
$229,900
- 1 Bed
- 2 Baths
- 848 Sq Ft
11F Snow Tree Ln Unit F, Dover, VT 05356

Be in the heart of the action at the base area of Mount Snow in this light-filled 1-bedroom, 2-bath end unit in the sought-after Snowtree community. Step out your door, stroll across the bridge and parking lot, and hop on the Magic Carpet lift—no need to drive. This well-designed end unit offers extra windows for abundant natural light, a smart floor plan, generous closet space, and two cozy

Chad Lackey Deerfield Valley Real Estate

11F Snow Tree Ln Unit F, Dover, VT 05356
/27
$550,000
- 3 Beds
- 3 Baths
- 3,148 Sq Ft
672 E Orchard St, West Brattleboro, VT 05301

You can't beat this location, overlooking the Brattleboro Country Club golf course. This home was built circa 1919, and has many cool vintage features such as retro curved metal kitchen cabinets and baths. Generous rooms include a large living room with two field-stone fireplaces, a spacious family room. This is a 3 bedroom house with 3 full bathrooms, but it's really about how you configure

John Hatton Berkley & Veller Greenwood Country

672 E Orchard St, West Brattleboro, VT 05301
/60
$649,000
- 3 Beds
- 2 Baths
- 2,731 Sq Ft
49 Tyler St, Brattleboro, VT 05301

Rare opportunity to own this iconic Queen-Anne Victorian in Brattleboro’s coveted Tyler Street neighborhood. A remarkable and extremely rare blend of country and in-town living. Extraordinary and stunning views of the Connecticut River & Mount Wantastiquet. Lovingly cared for by the same owner for the past 29 yrs. This home sits proudly on the expansive 0.85-acre corner lot, in the core of

Dan Normandeau Berkley & Veller Greenwood Country

49 Tyler St, Brattleboro, VT 05301
/51
$575,000
- 3 Beds
- 2.5 Baths
- 2,494 Sq Ft
63 Cooper Hill Rd, Dover, VT 05356

Welcome to the original Cooper family homestead, a timeless treasure nestled on the highly sought-after Cooper Hill Road. This beautifully preserved antique home seamlessly blends historic character with thoughtful modern updates. A newly added composite deck with sleek cable railing is the perfect place to take in the stunning, long-range mountain views stretching over 100 miles toward NH’s Mt.

Michelle O'Neil Deerfield Valley Real Estate

63 Cooper Hill Rd, Dover, VT 05356
/27
$559,000
- 3 Beds
- 2.5 Baths
- 2,000 Sq Ft
16 View Rd, Wilmington, VT 05363

Great Chimney Hill vacation home in Lower B section. Super layout where kitchen, counter conversers, dining room folks and living room relaxers can choose to interact as one happy group, or maintain their own separate activities. The pellet stove fireplace & vaulted ceiling in the living room make for such a relaxing space, while the steps that lead to the large loft above provides yet another

Michael Purcell Berkley & Veller Greenwood/Dover

16 View Rd, Wilmington, VT 05363
/26
$449,000
- 3 Beds
- 2 Baths
- 1,288 Sq Ft
78 Taft Brook Rd, East Dover, VT 05341

Lovely country home that is being offered for the first time by the original owners. This special spot is 2 acres just off the Taft Brook in East Dover, a short drive from the Mount Snow ski resort, village of Wilmington, and Brattleboro. Enjoy complete privacy off the quiet country road, with beautiful landscaping, perennial gardens, natural stone work, level yard space, and direct access to

Adam Palmiter Berkley & Veller Greenwood/Dover

78 Taft Brook Rd, East Dover, VT 05341
/20
$299,000
- 3 Beds
- 1 Bath
- 1,178 Sq Ft
17 Winter Ct, Brattleboro, VT 05301

Classic Ranch Style Home! Just starting out or thinking of downsizing? This could be the one! Nestled in a sweet neighborhood, this charming ranch offers easy one-level living just minutes from downtown shopping, schools, and recreation. Set on a manageable 0.2 acre lot, this home features a bright enclosed porch/bonus room perfect for morning coffee, reading, or relaxing year-round. Continuing

Liz LaVorgna Berkley & Veller Greenwood Country

17 Winter Ct, Brattleboro, VT 05301
/57
$479,000
- 4 Beds
- 2 Baths
- 1,840 Sq Ft
17 Villager Extension, Dover, VT 05356

Spacious 4-bedroom, 2-bath home located within great proximity to Mount Snow, just over 6 miles away! The inviting living room features a cathedral ceiling and wood-burning fireplace, perfect for apres-ski relaxation. A large mudroom provides ample space for all your gear, and a level driveway makes for nice access. The partially finished basement includes a game room and additional hangout

Erica Reynolds Southern Vermont Realty Group

17 Villager Extension, Dover, VT 05356

Showing Results 1 - 40, Page 1 of 11

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

Windham County New Construction Homes

More About Living in Windham County

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

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 2025 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.