Windham County VT Homes for Sale

/60
$695,000
- 4 Beds
- 4 Baths
- 2,978 Sq Ft
23 Brook Rd, Town of Rockingham, VT 05101

Tucked away on 6.8± acres in the charming village of Saxtons River, this exceptional property offers year-round panoramic views & breathtaking gardens. Thoughtfully designed, the floor plan features two distinct wings. The classic Cape & the Carriage House. The Cape’s main level welcomes you with an inviting entry/mudroom and powder room, leading into a beautifully renovated eat-in kitchen

Isabella Luhrs BHG Masiello Keene

23 Brook Rd, Town of Rockingham, VT 05101
/48
$495,000
- 3 Beds
- 3 Baths
- 1,813 Sq Ft
1 Pheasant Ln, Dover, VT 05356

Whether you are unwinding from a long day at the slopes of Mount Snow or you just enjoyed 18 holes at the Country Club, relax and get away with this beautiful home located in Partridge Run. This home boasts 3 bedrooms, 3 full bathrooms plus a Loft! You are welcomed upon entry by a very spacious mudroom with ample room to store your equipment for all seasons. The living, kitchen and dining areas

Tobin Twelves Skihome Realty

1 Pheasant Ln, Dover, VT 05356
/42
$379,000
- 4 Beds
- 2 Baths
- 2,202 Sq Ft
20 Newell Hill Rd, Wardsboro, VT 05355

Step into the charm of yesteryear with this spacious 1835s home that has a story to tell—yours is next! Enter through the oversized mudroom, which once served as the town post office, from the attached three-bay garage with automatic doors. This home features generous rooms throughout, starting with a large kitchen and dining area, a living room, two main-level bedrooms, and a full bath. Enjoy

Erica Reynolds Southern Vermont Realty Group

20 Newell Hill Rd, Wardsboro, VT 05355
/17
$29,000
- Land
- 1.10 Acres
- $26,364 per Acre
0 Oak Hill Rd, Wardsboro, VT 05355

Nice, wooded lot with mature trees as it's never been cut. Easy gradual grade, located in Snow Mountain Farms. Easy drive to Stratton or Mount Snow. No engineering done on this lot, selling raw land. Easy to walk and view anytime! Located on the corner of White and Oak Hill Road.

Julie Lowe Lowe's Real Estate, LLC

0 Oak Hill Rd, Wardsboro, VT 05355
/14
$54,900
- Land
- 2.67 Acres
- $20,562 per Acre
00 Loon Circle Private, Londonderry, VT 05148

Nestled in the Powder Mill neighborhood of Londonderry, VT, this expansive 2.67-acre parcel offers a prime opportunity to build your dream home in a serene, wooded setting. With a 4-bedroom wastewater permit already in place and electricity at the street, much of the groundwork has been laid for seamless development. Powder Mill boasts its own network of private hiking trails and is located

Andie Fusco Four Seasons Sotheby's Int'l Realty

00 Loon Circle Private, Londonderry, VT 05148
/35
$36,500
- 1 Bed
- 2 Baths
- 941 Sq Ft
230 Qtr.2, 89 Grand Summit Way, Dover, VT 05356

Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This one bedroom sleep 6 Valley side unit includes a Kitchen, large living room area with a queen murphy bed and queen sleeper sofa and a king bed in the private bedroom with two full bathrooms .Benefits of Grand Summit ownership include the best ski in/out mountain location available. Use of the Grand Summit amenities all

Kelly Agrillo Southern Vermont Realty Group

230 Qtr.2, 89 Grand Summit Way, Dover, VT 05356
/21
$425,000
- 3 Beds
- 2 Baths
- 1,750 Sq Ft
43 1st Ln Unit 28, Wilmington, VT 05363

Beautiful updated condo overlooking the 1st green at the Haystack Golf Club, as well as the mountains and sunsets beyond. This lovely private unit sits right on one of the best courses in New England, and is a short drive from the village of Wilmington, nearby lakes, and Mount Snow and Hermitage Club ski resorts. The interior features a large open living space with vaulted ceilings, updated vinyl

Adam Palmiter Berkley & Veller Greenwood/Dover

43 1st Ln Unit 28, Wilmington, VT 05363
/24
$28,995
- 2 Beds
- 2 Baths
- 745 Sq Ft
304/06 Qtr.2,89 Grand Summit Way, Dover, VT 05356

Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 6 unit consists of two adjoining units Studio unit (306) Queen murphy bed , kitchenette and full bathroom. Hotel unit (304) Two king beds and full bathroom. Units are located the valley side of the hotel . Lock out units has the benefit of using the unit as a whole or stay in one side and rent the other side out.

Kelly Agrillo Southern Vermont Realty Group

304/06 Qtr.2,89 Grand Summit Way, Dover, VT 05356
/21
$99,500
- Land
- 13 Acres
- $7,425 per Acre
00 Vermont 9, Marlboro, VT 05344

Mountain views in Marlboro Vermont! This 13+ acre parcel is situated in the desirable community of Marlboro where you are never far from a farmstand, sugar house, community or cultural event, or recreation. Roughed-in driveway access from a paved state road, with direct routes west taking you to lakes and skiing. Molly Stark State Park is nearby too. Head east to Brattleboro for all of the

Jacki Murano Southern Vermont Realty Group

00 Vermont 9, Marlboro, VT 05344
/18
$374,500
- Land
- 1.06 Acres
- $353,302 per Acre
12 Someday Rd, Dover, VT 05356

Located in the prestigious Someday neighborhood of West Dover,VT this 1.06-acre building lot offers a unique opportunity to create your dream home with breathtaking views of Mount Snow ski resort. The lot, which once housed the original Someday homestead as your footprint, it is now ready for its next chapter. With a permit for sewer in place for a 6-bedroom home, the property provides a head

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

12 Someday Rd, Dover, VT 05356
/15
$54,000
- Land
- 1.10 Acres
- $49,091 per Acre
0 Scandia Village Rd Unit 6 & 7, Wardsboro, VT 05360

Don't' miss this fantastic opportunity to own this perfectly located lot! Halfway to Stratton Mountain and Mount snow. Close to Grout and Summerset Ponds! Consisting of two lots. This will be ideal for your future dreams of a Vermont getaway! Just insert your imagination.

Daire Gibney Barrett and Valley Associates Inc.

0 Scandia Village Rd Unit 6 & 7, Wardsboro, VT 05360
/31
$1,750,000
- 4 Beds
- 3.5 Baths
- 2,698 Sq Ft
148 Sunbowl Ridge Rd, 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

Andrew King Stratton Real Estate

148 Sunbowl Ridge Rd, Stratton, VT 05360
/52
$999,000
- 4 Beds
- 2 Baths
- 2,741 Sq Ft
20 Finkel Rd, Wardsboro, VT 05355

Nestled on nearly 260 acres, this exquisite 18th-century solid post & beam 4 bedroom 2 bath cape offers a harmonious blend of historic charm and modern convenience. Boasting original features like fireplaces, wood flooring, and exposed beams, the home is filled with character. Spacious rooms create a perfect setting for gatherings. Recent updates include a new roof, windows, furnace & oil tank;

Jennifer Hovey-Densmore Deerfield Valley Real Estate

20 Finkel Rd, Wardsboro, VT 05355
/33
$1,000,000
- Land
- 21 Acres
- $48,309 per Acre
0 Crotty Dr, Town of Rockingham, VT 05101

Investors, developers and builders take notice! This large, lightly sloped parcel is one the last & largest undeveloped lots of land that fall within the Bellows Falls Village District. Just minutes from downtown and abutting the Minards Pond nature area, this property sits high on the hill with spectacular views available. With numerous potential building locations and town water and sewer, the

Courtney Doubleday EXP Realty

0 Crotty Dr, Town of Rockingham, VT 05101
/36
$499,000
- 3 Beds
- 3 Baths
- 2,144 Sq Ft
44 Villager Loop, Dover, VT 05356

Mountain Retreat located at 44 Villager Loop, Dover Hills, Dover, VT Very little use and never rented. Upgrades include a freshly painted exterior with a new roof and 3 mini-splits. Large mudroom entry, living room with fireplace, kitchen, dining area, 3 bedrooms, 3 baths, family room and a large deck for entertaining and relaxing. Close to the town center, restaurants, Town Park and Valley

Janet Boyd Boyd Real Estate

44 Villager Loop, Dover, VT 05356
/15
$530,000
- Land
- 30 Acres
- $17,667 per Acre
00 W Hill Rd S, Jamaica, VT 05343

Discover 30+ acres of coveted Vermont land, offering breathtaking views, open fields, stonewalls, large pond & established driveway. This unique property features an expansive, man-made pond that’s clean, deep, and perfect for paddling, swimming, or even stocking with fish. Excellent southern exposure for solar energy possibilities ,power line access adjacent to the property, this land offers

Jacki Murano Southern Vermont Realty Group

00 W Hill Rd S, Jamaica, VT 05343
/28
$499,000
- 2 Beds
- 2 Baths
- 1,040 Sq Ft
5 Northbrook Village Rd Unit A 27, Dover, VT 05356

Discover the ultimate winter retreat with this beautifully updated two-bedroom condo, perfectly situated just a short walk from the lifts and the brand-new base lodge at the Sundance face of Mount Snow. Step inside and be greeted by the warm ambiance of bamboo floors, complemented by sleek granite countertops and a stylish mosaic tile backsplash in the kitchen.The condo is part of the Seasons

Mike Masters Four Seasons Sotheby's Int'l Realty

5 Northbrook Village Rd Unit A 27, Dover, VT 05356
/40
$895,000
- 5 Beds
- 3.5 Baths
- 3,436 Sq Ft
67 Castle Hill Rd, Wilmington, VT 05363

Rare opportunity to own a meticulous 1830s vintage farmhouse, completely turn-key with extensive updates, renovations, and modern amenities. Conveniently located just outside the country village of Wilmington for shopping and great dining options, a short drive to the Mount Snow ski resort, and just up the street from the Lake Whitingham boat launch and beach areas, for true four season

Adam Palmiter Berkley & Veller Greenwood/Dover

67 Castle Hill Rd, Wilmington, VT 05363
/2
$90,000
- Land
- 1.97 Acres
- $45,685 per Acre
24 Summit Cir, West Brattleboro, VT 05301

Gorgeous building lot nestled into a prime development on a wooded hillside in Southern Vermont. The 1.97 wooded lot is minutes to downtown Brattleboro, yet private and rural!

Claire Renaud Berkley & Veller Greenwood Country

24 Summit Cir, West Brattleboro, VT 05301
/29
$25,000
- Land
- 0.60 Acre
- $41,667 per Acre
0 Upper Howes Way Unit 5008127, Wilmington, VT 05363

BUILD your dream home in this Lot in Section A! Buyer assumes responsibility for pursuing a septic plan and permit, and all costs associated with permitting and building. Lots 25 & 26 are also available and can be combined for a double or triple lot at the end of the road/world. Enjoy the wellness VT lifestyle and all the 1,200-acre resort with our exclusive member-only clubhouse located at 200'

Sigrid Pickering Chimney Hill Realty

0 Upper Howes Way Unit 5008127, Wilmington, VT 05363
/32
$25,000
- Land
- 0.56 Acre
- $44,643 per Acre
0 Upper Howes Way Unit 5008126, Wilmington, VT 05363

BUILD your Getaway Section A! Buyer assumes responsibility for pursuing a septic plan and permit, and all costs associated with permitting and building. Lots 25 & 26 are also available and can be combined for a double or triple lot at the end of the road/world. Enjoy the wellness VT lifestyle and all the 1,200-acre resort with our exclusive member-only clubhouse located at 200' with fitness,

Sigrid Pickering Chimney Hill Realty

0 Upper Howes Way Unit 5008126, Wilmington, VT 05363
/37
$1,700,000
- 4 Beds
- 4.5 Baths
- 3,808 Sq Ft
15 Stone Ridge Loop, Dover, VT 05356

A rare opportunity to have a luxurious mountain property with views, still with great proximity to Mt Snow. This stunning barn style post and beam is nestled on a private 5.97 acre parcel at the rear of the Village at Sawmill Farms. The siting affords gorgeous pastoral views over the common field of the community, views of the peak of Mount Snow, and mountains beyond, with 180 degree winter

Adam Palmiter Berkley & Veller Greenwood/Dover

15 Stone Ridge Loop, Dover, VT 05356
/31
$39,900
- 1 Bed
- 2 Baths
- 709 Sq Ft
145/47 Qtr.1,89 Grand Summit Way, Dover, VT 05356

Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 6 unit consists of two adjoining units; Studio unit (145) Queen murphy bed, kitchenette, full bathroom and a balcony. Hotel unit (147) Two queen beds, full bathroom and balcony. Units are located the mountain side of the hotel just down the hallway from the Spa, ski locker, health club and pool.. Lock out units

Kelly Agrillo Southern Vermont Realty Group

145/47 Qtr.1,89 Grand Summit Way, Dover, VT 05356
/11
$85,000
- Land
- 3.50 Acres
- $24,286 per Acre
0 Dover Rd Unit Lot 5 5004950, 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

Mike Masters Four Seasons Sotheby's Int'l Realty

0 Dover Rd Unit Lot 5 5004950, Newfane, VT 05345
/14
$85,000
- Land
- 3.04 Acres
- $27,961 per Acre
0 Dover Rd Unit Lot 4 5004949, 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

Mike Masters Four Seasons Sotheby's Int'l Realty

0 Dover Rd Unit Lot 4 5004949, Newfane, VT 05345
/13
$85,000
- Land
- 3.15 Acres
- $26,984 per Acre
0 Dover Rd Unit 5004948, 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

Mike Masters Four Seasons Sotheby's Int'l Realty

0 Dover Rd Unit 5004948, Newfane, VT 05345
/24
$74,000
- 2 Beds
- 0.5 Baths
- 414 Sq Ft
33 W River St, Londonderry, VT 05155

Rustic riverfront cabin in the heart of South Londonderry. The perfect retreat for those looking for simple living yet close to amenities. The main floor features a cozy living room, and kitchen area, complete with a propane oven and range, mini fridge, small dining table, propane stove, and electric fireplace. Off the kitchen, you will find the bathroom, complete with an electric Incinolet

Peter Cahill EXP Realty

33 W River St, Londonderry, VT 05155
/40
$1,750,000
- 7 Beds
- 7.5 Baths
- 8,364 Sq Ft
251 Pratt Bridge Rd, Jamaica, VT 05343

Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An

TG Glazer Winhall Real Estate

251 Pratt Bridge Rd, Jamaica, VT 05343
/30
$581,000
- 4 Beds
- 2 Baths
- 1,866 Sq Ft
58 Colonial Ridge Rd, Dover, VT 05356

This Wonderful Home is being offered for the first time in over 20 years. The current owners have enjoyed it, and taken care of it with upgrades and upkeep as needed. The newer paint, standing seam metal roof, deck stain, kitchen remodel including appliances, glass slider, all interior solid core doors and Rinnai heating units are all evidence to the care this home has seen. The high ceilings

Steve Goldfarb Deerfield Valley Real Estate

58 Colonial Ridge Rd, Dover, VT 05356
/13
$65,000
- Land
- 2.00 Acres
- $32,500 per Acre
585 Sawmill Rd, Stratton, VT 05360

Ready to build! Nestled in the picturesque Snow Mountain Farms development, this prime 2 acre property offers the perfect canvas for your dream home. Situated in a great neighborhood with a convenient location, it provides easy access to both Mount Snow and Stratton. The property is equipped with a wastewater permit, septic design, an already cleared building envelope, and a driveway.

Carrie Mathews Winhall Real Estate

585 Sawmill Rd, Stratton, VT 05360
/23
$585,000
- 4 Beds
- 2.5 Baths
- 2,400 Sq Ft
494 Cobb Reed Rd, Wardsboro, VT 05355

This home offers the best of a country property. The 1800's cape provides many surprisingly large rooms for family gatherings or entertaining friends. The old character of the home is evident in the wide pine floors, old fireplaces and 12 over 12 windows. With 2 bedrooms and two full baths with soaker tubs on each floor this should meet everyone's needs. There is also an exercise room in the

David Brown Berkley & Veller Greenwood Country

494 Cobb Reed Rd, Wardsboro, VT 05355
/14
$129,000
- Land
- 2.01 Acres
- $64,179 per Acre
255 Linden Way Unit 15.8, Chester, VT 05143

A very rare find! Here is your chance to own 2+/- acres of beautiful "action ready" land in the town of Chester. Situated in a woodsy setting, your new home will feel intimate and private, yet only a 15 minute walk into the town of Chester. Best of all, the under ground electric, well, septic, cable and gravel pad are existing and ready to be built on! There is a flat upper pad for your home

Daire Gibney Barrett and Valley Associates Inc.

255 Linden Way Unit 15.8, Chester, VT 05143
/15
$100,000
- 2,090 Sq Ft
211 High St, Brattleboro, VT 05301

Here's a great opportunity! Formerly a 2 unit multi-family, this is currently a shell ready for your finishing! This property will need everything ... heating, electrical, plumbing, exterior work and full interior finishing. Very convenient to downtown, some off street parking but nicely sited above the road. Please do NOT park in the driveway.

A.J. Bellville Bellville Realty

211 High St, Brattleboro, VT 05301
/6
$45,000
- Land
- 1.00 Acre
- $45,000 per Acre
0 Boardman Loop, Wardsboro, VT 05360

In the Heart of it all! This affordable acre of land is close to skiing, hiking, ponds and all the good stuff Vermont has to offer. Electric poles are across the street and the neighbors are hooked up. Starlink and Xfinity charts say they service the area for at home work, streaming or game playing. There are Covenants attached for the after midnight reading. There is a small stream on the

Christine Lewis Brattleboro Area Realty

0 Boardman Loop, Wardsboro, VT 05360
/29
$274,900
- Land
- 34 Acres
- $8,085 per Acre
0 Hillside Dr Unit Lot 46 4998188, Wilmington, VT 05363

Discover your dream property! Offering a rare opportunity to own a 34.0 acre parcel with tremendous privacy and views. Rolling topography, stonewalls, and interior network of old snowmobile/logging trails meander throughout the property. Preliminary site visit suggests at least two potential house sites near the point of entry or if you are search for higher ground travel to the mountain top

Monique White Deerfield Valley Real Estate

0 Hillside Dr Unit Lot 46 4998188, Wilmington, VT 05363
/33
$144,900
- Land
- 5.00 Acres
- $28,980 per Acre
0 Happy Haven Rd Unit 4998180, Wilmington, VT 05363

Recent soil testing indicates favorable results to support two single family homes each home with three bedrooms! This five acre parcel is located on Route 100, just north of Wilmington center. Excellent corner building parcel with great road frontage, lush and open meadow land perfect for building. Stunning mountain range views overlooking the Deerfield River. Electric, telephone, cable and

Monique White Deerfield Valley Real Estate

0 Happy Haven Rd Unit 4998180, Wilmington, VT 05363
/42
$249,000
- 3 Beds
- 2 Baths
- 1,619 Sq Ft
5 Baker Brook Rd, Newfane, VT 05362

This unique 1820's home sits pretty by a babbling brook and just oozes old-world charm. Sit on the large porch and drift away to the sounds of the stream. Featuring 3 bedrooms and an office on the main floor this could be a great family home or vacation hideaway! With close proximity to ski resorts and endless hiking and biking, this charmer is ideally located. An extra 1/2 acre is also available

Daire Gibney Barrett and Valley Associates Inc.

5 Baker Brook Rd, Newfane, VT 05362
/60
$475,000
- 2 Beds
- 2.5 Baths
- 1,537 Sq Ft
28 Greensprings Rd Unit GS U16, West Dover, VT 05356

A rare gem hitting the market after 22 years. Its design spans two levels, 2-ensuite bedrooms & 2.5 baths, providing ample space for comfort & convenience. Sold furnished, it's primed for immediate enjoyment. Nestled within the Greenspring community, this unit offers easy access to the rec center, pool, & tennis courts, just a short stroll away. The private back deck affords stunning mountain

Donald Koelsch Deerfield Valley Real Estate

28 Greensprings Rd Unit GS U16, West Dover, VT 05356
/8
$189,900
- 3 Beds
- 2 Baths
- 2,098 Sq Ft
843 Kentfield Rd, Whitingham, VT 05361

Location! Location! Location! Only 15 minutes to Wilmington and all that winter fun...Lake Whitingham and parks and ponds right around the corner...yet, a country property with ample parking for all the toys! This 1865 home has been made ready for the next level of renovation. Use it as it is currently used as a 2 family or with minor changes return it to the original cape upstairs, downstairs.

Christine Lewis Brattleboro Area Realty

843 Kentfield Rd, Whitingham, VT 05361
/20
$99,000
- Land
- 2.10 Acres
- $47,143 per Acre
0 Oak Hill Road & Maple Dr Unit H-4/H-13 4985655, Wardsboro, VT 05355

Discover an exceptional opportunity to acquire two adjoining parcels of land, spanning a combined 2.1 acres and two separate deeds, located in the highly sought-after Snow Mountain Farms Community. Lot H13 enjoys a peaceful setting on a cul-de-sac along Maple Drive, while Lot H4 is nestled amidst the serene, wooded landscape of Oak Hill. Both parcels feature an approved 4-bedroom state

Helen Nault Wohler Realty Group

0 Oak Hill Road & Maple Dr Unit H-4/H-13 4985655, Wardsboro, VT 05355

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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.