Windham County VT Homes for Sale

/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
/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
/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
/60
$635,000
- 3 Beds
- 2 Baths
- 3,000 Sq Ft
121 Dover Hill Rd, Dover, VT 05341

Nestled in the tranquil countryside of Vermont, this property blends an equestrian retreat, homestead and ski getaway. Set on 5 private acres with vibrant perennial gardens, and abundant raspberry canes, it offers a serene escape for all seasons. Dover is considered the gateway to Vermont’s Green Mountain National Forest, with easy access to Grout Pond, Stratton, Glastonbury and the Somerset

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
/15
$850,000
- Land
- 52 Acres
- $16,368 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,

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/11
$665,000
- Land
- 69 Acres
- $9,653 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

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/8
$355,000
- Land
- 35 Acres
- $10,281 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
/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
/41
$795,000
- 3 Beds
- 2.5 Baths
- 2,800 Sq Ft
202 Pratt Bridge Rd, Jamaica, VT 05343

Your slice of heaven awaits! Leave your worries behind and step into a beautiful Southern Vermont home that's truly turnkey. This well-designed, fully furnished, 3 bedroom, 2.5 bath home on 1.8+/- professionally landscaped acres offers privacy and convenience to the area's premier slopes, trails and natural beauty. The heart of the home is an expansive chef’s kitchen where country cabinetry and

Geralyn Donohue Engel & Völkers Okemo

202 Pratt Bridge Rd, Jamaica, VT 05343
/19
$469,000
- 2 Beds
- 2.5 Baths
- 1,399 Sq Ft
15 Haymaker Ln Unit 6D, Wilmington, VT 05363

Beautiful condo on the side of Haystack mountain at the beautiful exclusive Hermitage Club Ski Resort. Enjoy sunrise views out your living room windows in this immaculate 2 bedroom, 2.5 bath unit. Walk in from the spacious mudroom entry to a living area with wood burning fireplace, deck overlooking the view, tremendous light and views, kitchen with breakfast bar, updated appliances, and gas

Adam Palmiter Berkley & Veller Greenwood/Dover

15 Haymaker Ln Unit 6D, Wilmington, VT 05363
/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
/42
$849,000
- 5 Beds
- 4.5 Baths
- 3,550 Sq Ft
65 Hillwinds N, Brattleboro, VT 05301

This beautiful Colonial blends timeless design with contemporary enhancements. Set on over 2 acres of landscaped grounds, the property offers a country setting just minutes from Brattleboro. Inside, the floor plan has been expanded with large, light-filled rooms & custom features. The gourmet kitchen is a showstopper, w/Quartz counters, custom cabinetry, top-tier appliances, glass tile backsplash

Robert Doyle Berkley & Veller Greenwood Country

65 Hillwinds N, Brattleboro, VT 05301
/41
$865,000
- 3 Beds
- 2.5 Baths
- 1,656 Sq Ft
2 Stratton Springs Rd Unit 2, Stratton, VT 05360

Welcome to the exceptional Resort Townhome community of Stratton Springs with private shuttle, Stratton Sports Center access and convenient location near the Stratton Mountain Resort Village and lifts. These upscale floor plans offer a multi level great room with 2 story ceilings, walls of windows with natural light and commanding fireplace. The second level gourmet kitchen and dining area

Kim Morgan-Wohler Wohler Realty Group

2 Stratton Springs Rd Unit 2, Stratton, VT 05360
/21
$450,000
- 2 Beds
- 2 Baths
- 1,060 Sq Ft
B-22 Sportscenter Village Way Unit B-22, Dover, VT 05356

Welcome to the enchanting TRAILSIDE condo, a splendid 2-bedroom, 2-bath retreat nestled in the highly sought-after Seasons on Mount Snow! Imagine cozy evenings by the crackling fieldstone wood-burning fireplace, while the open concept kitchen, living, and dining area envelop you in warmth and light. With upgraded kitchen and bathrooms, this tastefully furnished space is designed for both

Sheila Joyce-Albano Skihome Realty

B-22 Sportscenter Village Way Unit B-22, Dover, VT 05356
/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
/40
$550,000
- 4 Beds
- 2 Baths
- 1,908 Sq Ft
119 Main St, Putney, VT 05346

Built in 1798, 119 Main Street is the third oldest home in Putney. With its original beams, colonial architecture, and location on Main Street, it's a historic gem in waiting for new people to love it. The owner who resided here for many years, took pride in preserving and adding to the beautiful terraced perennial gardens throughout the large in-town lot, which is just under an acre. The

Heather Gleim CENTURY 21 North East

119 Main St, Putney, VT 05346
/41
$539,500
- 3 Beds
- 2.5 Baths
- 1,930 Sq Ft
182 Eastman Rd, Grafton, VT 05146

Tucked away on 27 +acres this well-built retreat offers 3 bedrooms and 2.5 bathrooms. The custom crafted kitchen flows to a sunny dining room and wraps to a cozy living room with fireplace and efficient wood burning stove. A first-floor bedroom and bath, makes this open concept floor plan convenient. There is an additional 3 season bonus room which opens to a screen porch for relaxing on summer

Janet Lucier Barrett & Valley Assoc. Inc

182 Eastman Rd, Grafton, VT 05146
/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
- 2,437 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
/23
$245,000
- 1 Bed
- 1 Bath
- 640 Sq Ft
9B Snow Mountain Village Unit 142, Dover, VT 05356

GORGEOUS VIEWS OF MOUNT SNOW from this bright, airy one-bedroom, top-floor, corner condo in Snow Mountain Village, just minutes to the base area! Recent updates to the building include a new roof and new skylights. The interior has been tastefully updated with wood-tone vinyl flooring, plush bedroom carpet, all new LG appliances, quartz countertop and kitchen cabinets, new bathroom vanity, new

Patricia Fitzpatrick Skihome Realty

9B Snow Mountain Village Unit 142, 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
/50
$649,000
- 3 Beds
- 3.5 Baths
- 3,191 Sq Ft
1721 Vt Route 11, Londonderry, VT 05148

Situated just above Londonderry village, this meticulously maintained home offers mountain views, great southern exposure, and a peaceful setting just minutes from local shops, dining, and outdoor recreation. The landscaped yard features perennial gardens, flowering trees, stone walls, a firepit, hot tub, and a back deck perfect for enjoying the outdoors.Inside, the main level includes an

Andie Fusco Four Seasons Sotheby's Int'l Realty

1721 Vt Route 11, Londonderry, VT 05148
/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
/32
$620,000
- 6 Beds
- 4 Baths
- 3,592 Sq Ft
1375 Sheldon Hill Rd, Wardsboro, VT 05355

Stunning unique 2024 renovated chalet with rare 2+ acre parcel and easy access to both Mount Snow and Stratton. This home exudes the vibe of a true Vermont ski retreat. Inside you are treated to a large open concept great room with vaulted ceilings, natural woodwork, and great natural light throughout thanks to large windows and transoms. There is a gas fireplace with stone hearth, upscale custom

Adam Palmiter Berkley & Veller Greenwood/Dover

1375 Sheldon Hill Rd, Wardsboro, VT 05355
/24
$599,000
- 3 Beds
- 3 Baths
- 2,625 Sq Ft
282 Pams Hill Rd, Wardsboro, VT 05355

As Vermonty as you can get! Located conveniently between Mount Snow and Stratton, for easy access to skiing, shopping, lakes, and summer fun, sits this idyllic log style chalet with tremendous personal use or rental potential. The home sits on a private parcel not far from the Snow Mountain Farms amenities including indoor pool and tennis court. There is ample parking thanks to a cul de sac

Adam Palmiter Berkley & Veller Greenwood/Dover

282 Pams Hill Rd, Wardsboro, VT 05355
/59
$549,000
- 3 Beds
- 2.5 Baths
- 2,500 Sq Ft
30 Big Bend Loop, Wilmington, VT 05363

Escape to the Green Mountains in this beautifully designed 3+ bedroom home with a spacious loft, 2 bonus rooms, and three finished levels in the sought-after Chimney Hill community, fully permitted for short-term rentals with strong income history—ideal for investors or second-home buyers looking to offset costs. Step inside the custom mudroom with built-in cubbies, bench, and closets, and enter

Chad Lackey Deerfield Valley Real Estate

30 Big Bend Loop, Wilmington, VT 05363
/40
$489,000
- 5 Beds
- 3 Baths
- 2,917 Sq Ft
3550 Coolidge Hwy, Guilford, VT 05301

This lovely property has classic character and charm with modern updates and upgrades making this a truly comfortable place to call home! There's the main house with attached garage as well as the accessory in-law suite/apartment/accessory living space for longer term guests to stay that provides privacy from your main home. There's the nicely sized barn for parking, animals or storage which

A.J. Bellville Bellville Realty

3550 Coolidge Hwy, Guilford, VT 05301
/17
$149,000
- Land
- 18 Acres
- $8,054 per Acre
461 Deer Run, Putney, VT 05346

This fantastic property has so much potential, with multiple open fields and sections that are cleared as well as the surrounding wooded areas that add privacy and shade. Currently used as a camp with a barn, work shop, garage and more. The property also features a dug well that is currently not connected, a small pond and stream and a lot of great wildlife.

Thaddeus Abare Barrett and Valley Associates Inc.

461 Deer Run, Putney, VT 05346
/27
$249,000
- 2 Beds
- 1 Bath
- 970 Sq Ft
3153 Vermont Route 100, Wardsboro, VT 05355

Charming 2-bedroom, 1-bath rustic cottage featuring a versatile 14x9 mudroom and plenty of recent upgrades. The spacious kitchen flows into a generous dining area, while the cozy living room offers a VT Castings woodstove, a side bar with stools, and warm, inviting finishes. Both bedrooms are nicely sized, with one offering sliding doors that open directly to the backyard—perfect for easy outdoor

Jennifer Hovey-Densmore Deerfield Valley Real Estate

3153 Vermont Route 100, Wardsboro, VT 05355
/29
$1,697,000
- 4 Beds
- 3 Baths
- 2,420 Sq Ft
197 Lake Raponda Rd, Wilmington, VT 05363

This vintage renovated waterfront home is being offered for the second time in 40 years. Lake Raponda allows motorized craft, with primarily private beach front, and a small local boat launch and public beach. It is located conveniently down from the Mt Snow Ski Resort, on a quiet road, affording year round enjoyment and solitude. This home has been lovingly maintained, updated, and expanded by

Adam Palmiter Berkley & Veller Greenwood/Dover

197 Lake Raponda Rd, Wilmington, VT 05363
/22
$130,000
- Land
- 10 Acres
- $12,500 per Acre
oos-65-13 Partridge Ln, Jamaica, VT 05343

Wooded 10 acre lot #17 end of road, past camp. Part of the Gleason Farm Deed of Conservation Easement for Wildlife and Forest Land Protection, granted by Patten Corp. Property being offer with Travel Trailer. Enjoy your Vermont get away.

Mike England Michael England Real Estate

oos-65-13 Partridge Ln, Jamaica, VT 05343
/35
$439,000
- 3 Beds
- 3 Baths
- 1,785 Sq Ft
401 Crane Mountain Rd, Townshend, VT 05353

Well maintained spacious log home located on 3 + acres in a beautiful country setting. Open concept living /dining area with woodburning stove, double siders open to a large wrap around deck with winter mountain views. This comfortable home offers a cozy eat - in kitchen with sweet access window to dining room. The flexible floorplan has a convenient first floor bedroom and bathroom. The second

Janet Lucier Barrett & Valley Assoc. Inc

401 Crane Mountain Rd, Townshend, VT 05353

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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.