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
/22
$1,000,000
- Land
- 67 Acres
- $14,925 per Acre
00 S Pine Banks Rd, Putney, VT 05346

Unleash the potential of this exceptional 60+ acre Vermont property, a rare offering brimming with diverse landscapes and endless possibilities. A well-maintained gravel driveway leads you into the heart of the land, complete with readily available power. Discover multiple potential building sites, each offering breathtaking views or secluded privacy, tailored to your preference. A charming

Ross Doody

Century 21 Highview Realty

(802) 499-2391

00 S Pine Banks Rd, Putney, VT 05346
/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
/25
$189,000
- 2 Beds
- 1 Bath
- 1,000 Sq Ft
22 Chestnut St Unit 1, Brattleboro, VT 05301

Welcome to 22 Chestnut Street, Unit #1 — a charming and fully furnished first-floor condo nestled in the lovely Chestnut Street neighborhood. This spacious 2-bedroom, 1-bath unit features a thoughtfully updated bathroom with a clawfoot tub and separate shower, a cozy mudroom entryway, and a sunny side porch that conveys with the unit — perfect for morning coffee or evening relaxation. The kitchen

Erica Reynolds Southern Vermont Realty Group

22 Chestnut St Unit 1, Brattleboro, VT 05301
/30
$350,000
- 2 Beds
- 2 Baths
- 1,150 Sq Ft
65 E Birch Rd Unit 57, Stratton, VT 05155

Welcome to effortless mountain living at Stratton Mountain! This beautifully maintained end-unit 2-bedroom, 2-bath condo offers the perfect blend of comfort, privacy, and convenience. Ideally located with shuttle service to the lifts on winter weekends and holidays, your ski days begin and end with ease. After a day on the slopes, enjoy a short walk to the Stratton Sports Center for a swim,

Carrie Mathews Winhall Real Estate

65 E Birch Rd Unit 57, Stratton, VT 05155
/50
$575,000 Open Sat 10AM - 1PM
- 4 Beds
- 2 Baths
- 1,658 Sq Ft
5134 Vermont 9, Brattleboro, VT 05301

Escape to this hidden gem with mountain views, 17 rolling acres,& featuring a rare blend of privacy, beauty, & income potential in the heart of southern Vermont. The contemporary main house offers clean lines, warm wood floors, & modern comforts, ideal for year-round living or a peaceful retreat. Expansive windows fill the rooms with natural light & frame the stunning surroundings. This 4

Tamara Purcell Berkley & Veller Greenwood Country

5134 Vermont 9, Brattleboro, VT 05301
/49
$625,000
- 5 Beds
- 3 Baths
- 4,226 Sq Ft
24 Bluebrook Rd, Dover, VT 05356

Nestled less than two miles from Mount Snow, this spacious 4200 sf private home features 5 Bedrooms (plus a den) and 3 Bathrooms offering the perfect blend of seclusion, convenience, and entertainment.The expansive kitchen and two dining areas will effortlessly accommodate holiday gatherings and cozy Vermont evenings. Even with a full house, the third floor primary suite provides a serene

Melissa Ellis Southern Vermont Realty Group

24 Bluebrook Rd, Dover, VT 05356
/55
$1,000,000
- 3 Beds
- 2 Baths
- 2,700 Sq Ft
580 Cross Rd, South Londonderry, VT 05155

Tucked away in a tranquil setting, this newly constructed 3-bedroom, 2-bath barn-style residence is a masterful fusion of heritage & refined elegance, situated on 5.4 pristine acres. Absorb the beauty of reclaimed exposed overhead beams, while expansive floor-to ceiling custom-crafted windows capture mountain vistas & bathe interiors in golden natural light. Large sliding doors open to the melody

Loana Sargent Wohler Realty Group

580 Cross Rd, South Londonderry, VT 05155
/51
$725,000
- 4 Beds
- 2 Baths
- 1,370 Sq Ft
98 Darby Hill Rd, Bellows Falls, VT 05101

TOTAL PRIVACY ON 96 ACRES ABUTS THE VILLAGE FOREST & THE LOCATION OF MINARD'S POND. THIS WELL CARED FOR HOME IS CLASSIC COUNTRY THROUGHOUT W/HARD WOOD, WIDE BOARD FLOORS & BEAUTIFULL WOOD CEILINGS, FULLY APPLIANCED KITCHEN & LAUNDRY ROOM, UPDATED BATHS PLUS A REAR DECK W/TREX FLOORING OFF THE FOUR SEASON SUN ROOM. A LARGE 3 BAY BARN, WORKSHOP W/ 2ND FLOOR & ATTACHED CAR PORT W/CEMENT FLOOR.

Don Chabot Town and Country Realty

98 Darby Hill Rd, Bellows Falls, VT 05101
/59
$795,000
- 3 Beds
- 3.5 Baths
- 1,730 Sq Ft
2A Townhouse Square Unit T-4, Dover, VT 05356

Experience the best of all worlds! Just 100 feet from your front door, you can hop onto a Mount Snow ski trail, or take a short walk to the newly renovated and expanded, on-site Amenities Center, featuring an indoor pool, outdoor pool, exercise room, saunas, lockers, and more. This beautifully appointed, fully furnished townhome is truly turnkey. Inside, you’ll find three fireplaces—including one

John Redd Skihome Realty

2A Townhouse Square Unit T-4, Dover, VT 05356
/59
$539,000
- 3 Beds
- 2 Baths
- 2,000 Sq Ft
16 Nutmeg Ln, West Dover, VT 05356

Step into this warm, inviting home, and you may never want to leave. Tucked away on a private road just three minutes from Mount Snow's north entrance, this sunny retreat offers winter views of the mountain and a lifestyle that feels both relaxed and rejuvenating. Situated on 3.7 combined acres (2.75 in Dover, 0.95 in Stratton), there's plenty of open lawn space for kids and pets to run free.

Richard Caplan Deerfield Valley Real Estate

16 Nutmeg Ln, West Dover, VT 05356
/26
$549,000
- 3 Beds
- 1.5 Baths
- 1,287 Sq Ft
18 Old Town Rd, West Dover, VT 05356

Amazing mountain and sunset views from this absolutely immaculate home just south of the Mount Snow ski resort. Enjoy total privacy yet easy access with gorgeous lawn space, brook, and dead end privacy. The property consists of 3 building lots totaling 3.72 acres, with a 2 car garage, garden shed, covered generator shed, and charming Cape house. The home is 3 bedrooms, 2 updated bathrooms,

Adam Palmiter Berkley & Veller Greenwood/Dover

18 Old Town Rd, West Dover, VT 05356
/44
$525,000
- 3 Beds
- 2.5 Baths
- 2,342 Sq Ft
2026 Stagecoach Rd, Grafton, VT 05146

Welcome to Silver Birches — a serene Vermont retreat nestled on 27 acres along a quiet country road, perfectly situated Grafton and Chester villages. Sprawling ranch-style home offers a fantastic floor plan with generously sized rooms and a natural flow, making it ideal as a year-round homestead or a peaceful getaway. The open-concept kitchen and dining area, complete with a cozy fireplace and

Jessica Landers Barrett and Valley Associates Inc.

2026 Stagecoach Rd, Grafton, VT 05146
/60
$589,000
- 3 Beds
- 3 Baths
- 2,772 Sq Ft
7 Grassy Brook Rd, Brookline, VT 05345

Welcome to The River House—a completely renovated, turn-key escape located directly on the scenic West River, complete with its own private beach. Whether you’re seeking a peaceful getaway, a year-round residence, or an investment property with proven short-term rental history, this home checks every box. Inside, the property has been thoughtfully updated from top to bottom: all-new flooring,

Flex Realty Group Flex Realty

7 Grassy Brook Rd, Brookline, VT 05345
/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
/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
/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
/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
/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
/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
/13
$375,000
- 2,293 Sq Ft
62 Westminster Rd, Putney, VT 05346

Outstanding owner-occupied investment opportunity! This well-maintained 4-unit multi-family property on Westminster Road offers one 1-bedroom unit and three 2-bedroom units. Located in the heart of Putney village with easy walking access to shops, restaurants, post office, library, and the renowned Yellow Barn Music Festival. This .86 acre property features a private backyard for peaceful

Lilly Gallagher Greenwald Realty Group

62 Westminster Rd, Putney, VT 05346
/38
$339,000
- 2 Beds
- 1 Bath
- 1,120 Sq Ft
154 Reed Rd, Chester, VT 05143

Nature surrounds this charming cabin-style home, tucked into the woods and overlooking a peaceful pond. Privately situated, the home features an open-concept living area with a vaulted ceiling, inviting in natural light and offering views of the water. Step outside to a brand-new deck that extends your living space outdoors. The cozy kitchen is both functional and full of character, with

Jessica Landers Barrett and Valley Associates Inc.

154 Reed Rd, Chester, VT 05143

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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.