Windham County VT Homes for Sale

/37
$449,000
- 6 Beds
- 2.5 Baths
- 3,032 Sq Ft
3458 Vt Route 30, Jamaica, VT 05343

This lovely, updated 1790 Cape blends timeless New England charm with modern functionality and post-and-beam construction. Ideally located just outside the quaint village of Jamaica, the home offers easy access to four major ski resorts—Stratton, Bromley, Magic Mountain, and Mount Snow. Step into the welcoming kitchen, where a cozy fireplace creates a perfect winter haven. A soaring cathedral

Thomas Dahlin Berkley & Veller Greenwood Country

3458 Vt Route 30, Jamaica, VT 05343
/49
$1,025,000
- 5 Beds
- 6 Baths
- 5,600 Sq Ft
10 14 Wiswall Hill Rd, Newfane, VT 05345

Welcome to an exceptional property set on 8 acres of meadow w/ stone walls, woodland, and frontage on the Smith Brook. This contemporary barn conversion was architect designed & boasts an impressive Great Room with soaring ceilings, exposed post & beams, and gas fireplace. Patio doors open onto a huge deck, offering views of the in-ground pool and serene surroundings. The dining room, crafted

Robert Doyle Berkley & Veller Greenwood Country

10 14 Wiswall Hill Rd, Newfane, VT 05345
/41
$725,000
- 3 Beds
- 3.5 Baths
- 4,219 Sq Ft
5 N Main St, Wilmington, VT 05363

Located in the heart of downtown Wilmington and just minutes from Mount Snow and Harriman Reservoir, this exceptional mixed-use property offers incredible flexibility, income potential, and style. Currently operating as a successful VRBO rental that sleeps 12, this all-season retreat includes multiple living areas, a hot tub, sauna, and a stunning vaulted post-and-beam loft with a bar, pool

Morriah Adams BHG Masiello Brattleboro

5 N Main St, Wilmington, VT 05363
/17
$201,400
- Land
- 2.80 Acres
- $71,929 per Acre
37 Fred Houghton Rd, Putney, VT 05346

Just in time! So special! This unusual offering was a beloved family complex for many years. The land is a delight of mixed hardwoods and evergreens, easy to walk and gently rolling for intrigue. Walk to "downtown" Putney for the small town energy, pop in the auto for a short drive to everything else...interstate access, NH, skiing...hospitals and services.....or tuck in at home for a

Christine Lewis Brattleboro Area Realty

37 Fred Houghton Rd, Putney, VT 05346
/51
$350,000
- 6 Beds
- 3 Baths
- 3,468 Sq Ft
31 School St, Bellows Falls, VT 05101

Attractive and well maintained 3 unit Multi-family with great in-town location. Many original features remain including wood floors, 2 marble mantles, moldings, curved walls, beautiful arches and built-ins. Unit 1 on the first floor features living room open via graceful arches to dining room, large eat-in kitchen, 2 large bedrooms,, hardwood floors, marble fireplaces. Unit 2 is on the 2nd floor

Steve Schoppmeyer BHG Masiello Brattleboro

31 School St, Bellows Falls, VT 05101
/43
$389,000
- 3 Beds
- 2 Baths
- 1,917 Sq Ft
152 Main St, Grafton, VT 05146

This charming home in Grafton is centrally located next to the MKT market, offering easy access to the post office, town offices, library, school, inn, church, and local shops. With spacious and bright rooms, the home welcomes you into a main foyer that features a living room and study as its two front rooms. A dining room adjoins the living room and leads to the kitchen at the back of the house.

Jessica Landers Barrett and Valley Associates Inc.

152 Main St, Grafton, VT 05146
/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

Richard Caplan Deerfield Valley Real Estate

309 Vermont Route 100, Dover, VT 05356
/28
$475,000
- 4 Beds
- 4 Baths
- 5,848 Sq Ft
2 Blackberry Ln, West Dover, VT 05356

Oh wow, get ready to fall head over heels for your dream home! This beauty is nestled in the perfect spot, making every day feel like a breeze! You’ll be just a hop, skip, and a jump away from Dover Elementary School—how cool is that? Plus, if you're itching for a little adventure, Mount Snow Resort is only a quick 10-minute drive, and the charming vibes of Brattleboro are just a half-hour away!

John Redd Skihome Realty

2 Blackberry Ln, West Dover, VT 05356
/13
$79,000
- Land
- 3.69 Acres
- $21,409 per Acre
0 Honeycomb Hill, Marlboro, VT 05301

On the privately maintained road of Honeycomb Hill sits this 3.69 acre lot. The wooded parcel has young tree growth and slopes gently. There are three areas that are fairly level and open and may be suitable building sites. Just 30 minutes to Mt. Snow, 25 minutes to Brattleboro and 15 minutes to Harriman Reservoir, this conveniently located parcel offers easy access to all of Southern Vermont's

Laura D'Angelo Berkley & Veller Greenwood Country

0 Honeycomb Hill, Marlboro, VT 05301
/37
$899,500
- 4 Beds
- 4 Baths
- 3,100 Sq Ft
25 Boulder Ridge Dr Unit B, Dover, VT 05356

This magnificent 4-bedroom, 4-bathroom townhouse, spanning over three tastefully designed floors, will captivate you with its elegance. The open floor plan combines contemporary aesthetics with practical design, offering a living experience par excellence. This townhouse was finished in 2021 and has the “new construction” feel. The living room, graced with hardwood flooring, a gas fireplace,

John Redd Skihome Realty

25 Boulder Ridge Dr Unit B, Dover, VT 05356
/24
$899,000
- 4 Beds
- 3 Baths
- 2,746 Sq Ft
1 Mortise Ln, West Dover, VT 05356

Stunning luxury townhome at the base of the Mount Snow ski resort. This beautiful turn key unit was built in 2016 and affords easy access to the mountain with privacy and size typically only available further away. Enjoy rustic natural woodwork with great natural light, a large open concept living space with wood floors, vaulted great room, floor to ceiling wood burning fireplace, a large open

Adam Palmiter Berkley & Veller Greenwood/Dover

1 Mortise Ln, West Dover, VT 05356
/34
$1,350,000
- 5 Beds
- 4.5 Baths
- 5,153 Sq Ft
15 Springhill Rd, Dover, VT 05356

Enjoy perfect Vermont styling in this spacious and functional home just a short drive to the Mount Snow ski resort, nearby lakes, and villages. This private location is nestled just off the Mount Snow golf course in the Deerfield Valley, and easily accessible from a paved road. The home has been fully renovated with no expense spared. Features include an open concept floor plan with expansive

Adam Palmiter Berkley & Veller Greenwood/Dover

15 Springhill Rd, Dover, VT 05356
/45
$310,000
- 2 Beds
- 1 Bath
- 1,909 Sq Ft
672 Huckle Hill Rd, Vernon, VT 05354

Charming historic home with modern updates and exceptional outdoor Living! This sweet, well-built home exudes character and curb appeal. Thoughtfully updates over the years, it features a striking standing seam metal roof, updated 200-amp electric panel, fabulous 2 story deck with low-maintenance Trex decking and a slab for a hot tub, complete with the hookup. Inside, enjoy the convenience of

Kerry Mulverhill Brattleboro Area Realty

672 Huckle Hill Rd, Vernon, VT 05354
/41
$299,000
- 4 Beds
- 1 Bath
- 1,612 Sq Ft
178 Parsons Rd, Wilmington, VT 05363

Charming Cape-style home set on 1.7 beautifully landscaped acres, featuring a detached two-car garage. The expansive yard includes established gardens, a BBQ area, a barn, and two additional sheds in need of some TLC. Located just 4 miles from downtown Wilmington, you’ll enjoy easy access to shopping, dining, and year-round outdoor activities like skiing, golfing, hiking, biking, and boating. The

Jennifer Hovey-Densmore Deerfield Valley Real Estate

178 Parsons Rd, Wilmington, VT 05363
/19
$249,000
- Land
- 30 Acres
- $8,275 per Acre
189 North St, Dover, VT 05356

Discover the perfect Vermont retreat on this 30.09 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape.Whether you

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

189 North St, Dover, VT 05356
/16
$85,000
- Land
- 10 Acres
- $8,500 per Acre
Lot 4 North St, Dover, VT 05431

Discover the perfect Vermont retreat on this 10.00 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape.Whether you

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

Lot 4 North St, Dover, VT 05431
/10
$95,000
- Land
- 10 Acres
- $9,453 per Acre
Lot 3 North St, Dover, VT 05431

Discover the perfect Vermont retreat on this 10.15 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape.Whether you

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

Lot 3 North St, Dover, VT 05431
/9
$125,000
- Land
- 10 Acres
- $12,450 per Acre
Lot 2 North St, Dover, VT 05431

Discover the perfect Vermont retreat on this 10.48 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape.Whether you

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

Lot 2 North St, Dover, VT 05431
/9
$465,000
- 7 Beds
- 4 Baths
- 3,551 Sq Ft
1950 N Main St, Londonderry, VT 05148

This is a unique, one of a kind, versatile, "blank canvas" opportunity. This is a 3 unit multi-family, fully rented/money making full time property now.. but, use your imagination, create your vision of what this premier location could be. Zoned BOTH commercial AND residential.. this property could be a fabulous restaurant with rivers edge al fresco dining or...a potential location for a new

Wilkie Bushby TPW Real Estate

1950 N Main St, Londonderry, VT 05148
/35
$225,000
- Land
- 12 Acres
- $18,160 per Acre
712 Stimpson Hill Rd, Whitingham, VT 05361

Discover this stunning and private 12+ acre parcel, bathed in sunshine and nestled on a quiet dead-end road. Featuring a beautiful open meadow framed by classic stone walls, this idyllic setting offers the perfect location for building your dream home. The property comes ready with essential infrastructure, including; State of Vermont wastewater permit with an approved septic design for a

Monique White Deerfield Valley Real Estate

712 Stimpson Hill Rd, Whitingham, VT 05361
/37
$299,000
- 3 Beds
- 2.5 Baths
- 1,200 Sq Ft
301C Vermont Route 100 Unit C, Dover, VT 05356

Charming 3-bedroom, 2.5-bath condo located just one mile from Mount Snow! This cozy mountain getaway offers views of the slopes from the living room and back deck and offers easy access to the Moover shuttle—just steps away. Inside, you’ll find a warm and welcoming space featuring new granite counter tops in the kitchen and a recently installed heat pump providing efficient heating in the winter

Chad Lackey Deerfield Valley Real Estate

301C Vermont Route 100 Unit C, Dover, VT 05356
/23
$1,150,000
- 6,442 Sq Ft
69-71 Elliot St, Brattleboro, VT 05301

Prime commercial opportunity in the heart of downtown Brattleboro. This mixed-use property features seven residential apartments on the upper levels and five ground-floor commercial units. Two retail spaces have direct frontage on Elliot Street, offering strong visibility, while three others open onto the Harmony Lot pedestrian area, a centrally located public parking and business zone. The

Erica Reynolds Southern Vermont Realty Group

69-71 Elliot St, Brattleboro, VT 05301
/28
$225,000
- 3 Beds
- 1.5 Baths
- 1,531 Sq Ft
316 Putney Rd, Brattleboro, VT 05301

Convenient Location & Low Maintenance Living! Enjoy easy access to shopping, public transportation and waterfront with scenic trails. The backyard is just the right size for enjoying nature and a little fresh air. This charming home combines classic character with practical updates featuring a standing seam roof, vinyl windows and aluminum siding. Inside, the home radiates its original charm

Kerry Mulverhill Brattleboro Area Realty

316 Putney Rd, Brattleboro, VT 05301
/45
$285,000
- 3 Beds
- 1.5 Baths
- 1,728 Sq Ft
121 Happy Haven Rd, Wilmington, VT 05363

This home offers endless potential to become your ideal retreat. Tucked away on 1.3 acres at the end of a quiet dead-end road, it provides privacy while still being conveniently close to downtown Wilmington and year-round recreation—whether you enjoy skiing, golfing, hiking, biking, or boating. The main level features an open-concept layout with a cozy living room with a wood-burning fireplace, a

Jennifer Hovey-Densmore Deerfield Valley Real Estate

121 Happy Haven Rd, Wilmington, VT 05363
/33
$249,000
- 2 Beds
- 1 Bath
- 1,000 Sq Ft
290 Old Mill Ln, Wilmington, VT 05363

“The Camp” Are you looking for that special seasonal getaway? Look no further! This charming 1-bedroom on the main level and second bedroom upstairs sleeping loft is located in the beautiful town of Wilmington. Nestled in the woods, this cozy cabin offers a unique and special Vermont experience. Enjoy the covered front porch and large deck, perfect for entertaining friends and family. Just steps

Richard Caplan Deerfield Valley Real Estate

290 Old Mill Ln, Wilmington, VT 05363
/26
$44,900
- Land
- 1.50 Acres
- $29,933 per Acre
00 E Putney Falls Rd, Putney, VT 05346

1.5 acre +/- corner lot along East Putney Falls Road and Bellows Falls Road (Route 5) with State WW permit in progress for a 3-bedroom home. Driveway access to potential building site off East Putney Falls Road. Level, wooded building area elevated from road. Power at road and adjacent to property. Close to Putney Diner, The General Store, Putney Coop and Landmark College.

Geralyn Donohue Engel & Völkers Okemo

00 E Putney Falls Rd, Putney, VT 05346
/19
$597,500
- Land
- 48 Acres
- $12,482 per Acre
111 Jockey Hollow Rd, East Dover, VT 05341

Set on 47.87 picturesque acres in East Dover, Vermont, this striking timber-framed barn offers a rare blend of craftsmanship, open land, and mountain lifestyle just minutes from Mount Snow and The Hermitage Club. With open land and sweeping mountain views, the property is ideally suited for a private estate, equestrian retreat, or recreational escape. The custom Timber Framed barn features a

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

111 Jockey Hollow Rd, East Dover, VT 05341
/55
$929,000
- 4 Beds
- 4 Baths
- 3,200 Sq Ft
45D Dover Spring Ln, Dummerston, VT 05356

Enjoy the perfect blend of comfort, convenience, and scenic beauty in this exceptional townhome located in the highly desirable Greenspring community. The private setting offers a spacious backyard, mountain views and a nearby pond. This home offers the peace and tranquility of country living while remaining just minutes from skiing and outdoor recreation.Boasting an expansive 3,200

Melissa Ellis Southern Vermont Realty Group

45D Dover Spring Ln, Dummerston, VT 05356
/16
$488,875
- 5 Beds
- 4 Baths
- 3,064 Sq Ft
176 High St, Brattleboro, VT 05301

Unique opportunity to invest in your own home and have revenue from 2 apartments. Located close to all that Brattleboro has to offer for unique shopping, art, theater and lots of dining venues. The 1st floor apartment has over 1500 square feet of living space with 2+ bedrooms and two bathrooms, its own covered porch and expansive deck. Additionally, there is a spacious eat in kitchen, large

Susan Bellville Bellville Realty

176 High St, Brattleboro, VT 05301
/52
$329,000
- 3 Beds
- 2 Baths
- 1,239 Sq Ft
3185 Higley Hill Rd, Guilford, VT 05301

Originally built for the 1980 Lake Placid Winter Olympics, this iconic A-frame was later relocated to a serene 2+ acre setting in Marlboro Vermont. Tucked away on a quiet paved road, this 3-bedroom, 2-bath home blends rustic charm with thoughtful updates, including spacious additions and featuring a large mudroom—perfect for storing winter gear after a day on the slopes. The open-concept

Chad Lackey Deerfield Valley Real Estate

3185 Higley Hill Rd, Guilford, VT 05301
/11
$75,000
- Land
- 1.80 Acres
- $41,667 per Acre
L40 Boardman Loop, Wardsboro, VT 05360

Nestled in the desirable Snow Mountain Farms West community, this 1.8-acre wooded lot offers the perfect setting to build your Vermont dream home or getaway. Gently sloping and bordered by the serene Wardsboro Brook (outside the FEMA flood zone), the property combines natural beauty with practical readiness. A state-issued wastewater permit for a 3 bedroom single family home and an individual

Andie Fusco Four Seasons Sotheby's Int'l Realty

L40 Boardman Loop, Wardsboro, VT 05360
/30
$299,000
- Land
- 58 Acres
- $5,177 per Acre
0 Vermont Route 100, Jamaica, VT 05343

Over 57 IMPRESSIVE ACRES located in a NO ZONING town close to Stratton and Mount Snow! Large tract of land with stunning views from multiple locations throughout the property! State wastewater permit already in place and on file with the State of Vermont for construction of a three bedroom home, see permit number WW-2-5317 attached. So many other options available should you want to subdivide or

Julie Lowe Lowe's Real Estate, LLC

0 Vermont Route 100, Jamaica, VT 05343
/26
$385,000
- 2 Beds
- 1 Bath
- 1,176 Sq Ft
787 Vermont 30, Newfane, VT 05345

Perfect! If you have been looking for a workshop or studio, this is the perfect set up. 30x40, this huge open building has workshop benches, heat, electricity, water hook ups. There is a potential to hook to the septic....even create a 1 bedroom apartment. On top of this great find, there is a 2 car detached garage that can be also used for storage, a workshop or just plain garage! And, it

Christine Lewis Brattleboro Area Realty

787 Vermont 30, Newfane, VT 05345
/8
$199,500
- 3 Beds
- 2 Baths
- 2,262 Sq Ft
570 Rockingham Rd, Bellows Falls, VT 05101

What a great opportunity! This property in its heyday was a thriving Gift Shop and small campground, the owners lived on premises in a charming dormered cape. It has since fallen in disrepair but offers endless opportunity to the right person! The house is a three bedroom cape with a small attached studio apartment and a two car garage with a level, sunny,and private yard. The Gift Shop is almost

Oona Madden Berkley & Veller Greenwood Country

570 Rockingham Rd, Bellows Falls, VT 05101
/32
$25,000
- Land
- 0.30 Acre
- $83,333 per Acre
0 Big Bend Loop Unit 5039354, Wilmington, VT 05363

One of a handful of single lots remaining on the Hill! Septic design needs updating, Power is at the street. The lot is buffered by common land on both sides, and there is a drop off at the back. Access is best at the left end of the property, where a gentle slope takes you to this level plateau. View with clearing and in non-leaf seasons. Build your dream home and enjoy all the amenities

Sigrid Pickering Chimney Hill Realty

0 Big Bend Loop Unit 5039354, Wilmington, VT 05363
/33
$425,000
- 1 Bed
- 1 Bath
- 700 Sq Ft
6878 Streeter Rd Unit 9&10, Wardsboro, VT 05360

Excellent opportunity to be close to everything Vermont has to offer and still feel secluded. This off grid efficient home is so easy to live in, get to and enjoy. IF you'd like to be on grid you're only about 7 power poles away. This offering is for currently combined 2 buildable lots which were subdivided many years ago. There is wonderful access to the woods for all activities. You can

Steve Goldfarb Deerfield Valley Real Estate

6878 Streeter Rd Unit 9&10, Wardsboro, VT 05360
/22
$325,000
- 3 Beds
- 1 Bath
- 1,104 Sq Ft
62 Lawton Dr, Brattleboro, VT 05301

Everything deserves a second chance, and this home found the right owner to love and recreate it in a stunning new life. Anyone who has looked at this home in the past few years, has to come back to see the shine....the fresh new look....the simplicity of move right in. Not only is this home refreshed stem to stern, it has new windows, siding, shingles, kitchen, bath.....and on and on! Tuck

Christine Lewis Brattleboro Area Realty

62 Lawton Dr, Brattleboro, VT 05301
/23
$349,000
- 2 Beds
- 1 Bath
- 941 Sq Ft
57 Hartley Hill Rd S, Putney, VT 05346

This charmingly restored 1820's brick, former one-room schoolhouse has been meticulously expanded to include two bedrooms, a kitchen and full bathroom, and sits on a tranquil 5-acre lot with a mostly open, old pasture. The property retains its historical charm with exposed hand-hewn beams in the former schoolhouse that now serves as the living/dining area. Ideal for a cozy primary residence,

Dan Normandeau Berkley & Veller Greenwood Country

57 Hartley Hill Rd S, Putney, VT 05346
/7
$499,000
- Land
- 2.00 Acres
- $249,500 per Acre
70 Overlook Dr, Dover, VT 05356

Stunning 2 acre building parcel at the prestigious Peaks at Mt Snow directly across from the ski resort. This lot affords tremendous privacy and exposure, but with amazing access and amenities including direct on call shuttle service from your door to the mountain, indoor pool, gym, clubhouse, and game courts. Paved road access, sewer, and water, means total peace of mind. Build your dream home

Adam Palmiter Berkley & Veller Greenwood/Dover

70 Overlook Dr, Dover, VT 05356
/20
$450,000
- 4 Beds
- 3.5 Baths
- 2,575 Sq Ft
3730 Route 100, Wardsboro, VT 05355

Property is being sold "as is where is" and does need some TLC. The house is set back off the road quite a bit for total privacy and there is a pond on the property. There is a one car garage, a full daylight basement, and a sun room.

Ginny Read Read Realty LTD

3730 Route 100, Wardsboro, VT 05355

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