Windham County VT Homes for Sale

/20
$119,000
- Land
- 10 Acres
- $11,667 per Acre
1105 S Hill Rd, Jamaica, VT 05343

Explore this exciting wooded 10.2+/- acre lot in the desirable town of Jamaica, VT. Jamaica has NO local zoning, making for simplified development, multiple cabins, camping and more. Plenty of road frontage on a year-round town plowed and maintained road. Best of all it is paved all the way to Wardsboro eliminating the difficulties of Vermont Mud Season. Utilities are located across from the

Curtis Trousdale Preferred Properties

1105 S Hill Rd, 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
/29
$849,000
- 3 Beds
- 2 Baths
- 2,216 Sq Ft
601 Bellows Falls Rd, Putney, VT 05346

A special and unique offering of a 40 acre homestead in sought after Putney, Vermont. Set back from the road on a private drive is a 3-4 bedroom cape with full basement and attached two car garage. Special features include an observatory room, entry foyer with spacious office, quality built-ins, dormers and a swimming pond. A second building offers a rustic exterior, modern interior, wonderful

Jody Graves Berkley & Veller Greenwood Country

601 Bellows Falls Rd, Putney, VT 05346
/30
$299,000
- 4 Beds
- 2 Baths
- 1,350 Sq Ft
5 Snow Drift Ln Unit 6, Londonderry, VT 05155

Are you looking to add a little Magic to your life? Then, this is the place for you! Located just off the base area of Vermont’s beloved Magic Mountain in Londonderry, this small, welcoming condo development has just 6 units and embodies the spirit of its nearby mountain with a closeknit and friendly community. Walk to the lifts and ski home in the winter months, wander over to the base area for

Claudia Harris Mary Mitchell Miller Real Estate

5 Snow Drift Ln Unit 6, Londonderry, VT 05155
/39
$387,500
- 2 Beds
- 2 Baths
- 1,150 Sq Ft
75 E Birch Rd Unit 39, Stratton, VT 05360

Welcome to Vantage Point ! This updated and well appointed end unit is conveniently located on the second level of the middle building right behind the Stratton Fitness Center overlooking the outdoor tennis and pickleball courts. More recent upgrades are new flooring throughout, newer washer/dryer and lighting. Guest bedroom is set up for families. Winter shuttle service to the mtn base lodge.

Terry Hill Berkshire Hathaway HomeServices Stratton Home

75 E Birch Rd Unit 39, Stratton, VT 05360
/23
$350,000
- 3 Beds
- 2.5 Baths
- 1,440 Sq Ft
61 Country Club Rd, West Dover, VT 05356

Charming 3-Bedroom Condo Just Minutes from Mount Snow!Welcome to your perfect Vermont getaway! This beautifully maintained 3-bedroom, 2.5-bath condo is ideally located in Southern Vermont, just minutes from the renowned Mount Snow Ski Resort and the Mount Snow Golf Course. Whether you're an outdoor enthusiast or seeking a peaceful retreat, this property offers the best of all

Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

61 Country Club Rd, West Dover, VT 05356
/12
$1,100,000
- 3 Beds
- 3 Baths
- 1,501 Sq Ft
759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340

Designed with the mountain enthusiast in mind, and located just a short walk from the Stratton Resort Village and ski slopes, this three bedroom three bath condominium offers quality and convenience. Private parking, pool, hot tub, sauna and shuttle to the slopes.

John Sikes Stratton Real Estate

759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340
/44
$574,000
- 3 Beds
- 2.5 Baths
- 2,023 Sq Ft
6940 Coolidge Hwy, Guilford, VT 05301

Located just north of the Massachusetts border, this home with two car detached garage is conveniently just 15 minutes from both Greenfield and Brattleboro.As you step inside to the mudroom you'll enter the coziest of kitchens radiating warmth and character. Featuring a wood stove, a stunning brick hearth with beehive oven, wooden beams adding rustic charm, while a cathedral ceiling keeps the

Rebecca Seymour Brattleboro Area Realty

6940 Coolidge Hwy, Guilford, VT 05301
/59
$650,000
- 4 Beds
- 2 Baths
- 3,090 Sq Ft
301 Maple St, Brattleboro, VT 05301

How sweet it is! It is the perfect time to own this home, as the season turns to spring all the extraordinary effort in design and creating the hardscape and gardens come to life in bursts of bloom, enchanting ribbons of perfume and delightful fragrant nooks. Out back, in the private, personal space is the 24x50 salt water pool....once a swim school pool....now an oasis waiting for you to kick

Christine Lewis Brattleboro Area Realty

301 Maple St, Brattleboro, VT 05301
/38
$649,000
- 6 Beds
- 3 Baths
- 2,312 Sq Ft
10 E Village Cir, Wilmington, VT 05363

Located across the road from The Hermitage Club at Haystack Mountain, only 5 minutes to Mount Snow and just 30 to Stratton, this single-family home offers the perfect blend of rustic charm and modern comfort. Set on 1.55 acres with a large, level yard and ample road frontage, the house sits well back from the road for privacy and a peaceful setting.Inside, the fully renovated first floor

Samantha Decker Deerfield Valley Real Estate

10 E Village Cir, Wilmington, VT 05363
/19
$799,000
- 4 Beds
- 4 Baths
- 1,575 Sq Ft
4L Trailside Village Way Unit H34, Dover, VT 05356

Welcome to H34 Trailside Village Way – Slopeside Living at Its Finest! This 4 bed, 4 bath Trailside condo in Seasons on Mount Snow offers ski-in/ski-out access, an open-concept living space filled with natural light, and a stunning floor-to-ceiling fieldstone fireplace. Just a short walk to the newly renovated $2.3M Sports Center with pools, hot tubs, gym, and more. Never rented and lovingly

Jessica Bentz Four Seasons Sotheby's Int'l Realty

4L Trailside Village Way Unit H34, Dover, VT 05356
/37
$589,000
- 7 Beds
- 5 Baths
- 3,518 Sq Ft
343 Haystack Rd, Wilmington, VT 05363

This spacious home is located near outdoor recreation spots like Mount Snow and Haystack Country Club. Tucked back on 3 acres with wooded surroundings offering privacy amongst the trees. The main house offers Four bedrooms, four baths; including a large primary suite. The spacious basement has a kitchen, bath and living space with walkout access to the backyard. The three-car garage with a

Jessica Citera Cummings & Co

343 Haystack Rd, Wilmington, VT 05363
/25
$625,000
- 5 Beds
- 3.5 Baths
- 2,240 Sq Ft
47 Ives Rd, Wilmington, VT 05363

Unique spacious log home near the Hermitage Ski Club with easy access to the resort, direct snowmobile trail access, and tremendous privacy. Also just down the access road from the Mount Snow ski resort, nearby country village of Wilmington for shopping and dining, and gorgeous area lakes. This updated rustic retreat sits on a level lot with ample parking, winter exposure to the east, and a gear

Adam Palmiter Berkley & Veller Greenwood/Dover

47 Ives Rd, Wilmington, VT 05363
/37
$195,000
- 1 Bed
- 1 Bath
- 624 Sq Ft
17F Snow Tree Ln Unit F, Dover, VT 05356

This Lovely Condo is just STEPS away from Mount Snow. Walk out your door, cross a cute little bridge, and BAM! You’re at the Base Area in just minutes. This 1-bedroom unit has a great view of the slopes and is being sold fully furnished to ensure you a seamless transition into enjoying your new Vermont getaway. Enjoy a day on the slopes then walk back, relax by the fire or warm up in the hot tub

Tony Tribuno Skihome Realty

17F Snow Tree Ln Unit F, Dover, VT 05356
/18
$230,000
- 1 Bed
- 2 Baths
- 848 Sq Ft
11B Snow Tree Ln Unit Birches B, Dover, VT 05356

Amazing nearby access directly across to the magic carpet at Mount Snow! This lovely updated Snowtree condo is located at the base of the Mount Snow ski resort with easy access to the mountain, as well as convenient amenities and full maintenance for peace of mind. This unit has been renovated to be more functional for sleeping and entertainment than a typical one bedroom. There is a large living

Adam Palmiter Berkley & Veller Greenwood/Dover

11B Snow Tree Ln Unit Birches B, Dover, VT 05356
/25
$729,000
- 4 Beds
- 3 Baths
- 2,600 Sq Ft
10 Grouse Ln Unit 10A, Dover, VT 05356

Stunning Post and Beam style townhome overlooking spectacular views of Mount Snow and Haystack ski trails with the sunsets in the west beyond. This private end unit features an amenity rich location thanks to direct VAST snowmobile trail access, hiking and biking trails in the summer, as well as easy access to the Mount Snow golf course which is directly through the adjacent woods, and nearby

Adam Palmiter Berkley & Veller Greenwood/Dover

10 Grouse Ln Unit 10A, Dover, VT 05356
/20
$250,000
- 1 Bed
- 1 Bath
- 640 Sq Ft
3C Snow Mountain Village Unit 113, Dover, VT 05356

The special assessment on this unit has been paid in full! Don’t miss out on this incredible opportunity to own a cozy mountain getaway at Snow Mountain Village! This beautifully updated 1 bed, 1 bath condo offers the perfect balance of comfort and convenience. With breathtaking mountain views right from your first-floor patio, you can relax and enjoy the natural beauty of the area

Carrie Mathews Winhall Real Estate

3C Snow Mountain Village Unit 113, Dover, VT 05356
/36
$590,000
- 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
/34
$595,000
- 3 Beds
- 3 Baths
- 2,100 Sq Ft
4 Summit Meadows Ln, Dover, VT 05356

This well-maintained 3-bedroom, 2-bath home is set back from the road, offering privacy and scenic winter views of Haystack Mountain from the inviting living room with a cozy gas fireplace. The open-concept main level features a spacious mudroom with laundry, a guest bedroom, a full bath, and a bright living, dining, and kitchen area. Upstairs, you'll find two additional bedrooms and a second

Jennifer Hovey-Densmore Deerfield Valley Real Estate

4 Summit Meadows Ln, Dover, VT 05356
/42
$519,000
- 3 Beds
- 2 Baths
- 2,100 Sq Ft
38 Yeaw Rd, Dover, VT 05341

Enjoy the beauty and serenity of Vermont from this lovely 3 bedroom, 2 bath secluded country home set back off the road on 1.93 acres with a circular drive. The home features: a Primary Suite on the second level with a sitting room/office area, spa tub, oversized walk-in closet and an additional finished storage space. There are two bedrooms and a guest bathroom on the first floor along with an

Lisa Mirando Deerfield Valley Real Estate

38 Yeaw Rd, Dover, VT 05341
/33
$660,900
- 4 Beds
- 2 Baths
- 2,070 Sq Ft
239 Valley View Rd, Dover, VT 05356

This contemporary 3-bedroom plus loft, 2-bath home in Dover Hills offers both comfort and convenience. The property features a detached 2-car garage with overhead storage, an additional carport, and a wood shed. The recently remodeled kitchen boasts new cabinets, countertops, and appliances, complemented by wood floors throughout and new skylights that fill the space with natural light. A gas

Jennifer Hovey-Densmore Deerfield Valley Real Estate

239 Valley View Rd, Dover, VT 05356
/35
$649,000
- 5 Beds
- 3 Baths
- 2,223 Sq Ft
31 Joan's Ridge Rd, West Dover, VT 05356

This spacious 5-bedroom plus loft, 3-bath contemporary home is nestled in the Joan's Ridge community, just minutes from Mount Snow and the Hermitage Club. Step into a welcoming mudroom with a bench with built in boot warmer and cubbies, leading to a cozy living room with a wood-burning fireplace, a dining area, a fully equipped kitchen with island, one bedroom, a full bath and a den perfect for

Jennifer Hovey-Densmore Deerfield Valley Real Estate

31 Joan's Ridge Rd, West Dover, VT 05356
/42
$610,000
- 6 Beds
- 3.5 Baths
- 2,766 Sq Ft
624 Boyd Hill Rd, Wilmington, VT 05363

Welcome to this gorgeous, fully updated home where modern elegance meets everyday comfort! Nestled on 2 wooded acres, this home is centrally located for year-round enjoyment. Just up the road from Wards Cove Beach at Lake Whitingham, a short drive to the Village of Wilmington which is bustling with restaurants and shops and within minutes to the Mount Snow Ski Resort and The Hermitage Club. This

Patricia Fitzpatrick Skihome Realty

624 Boyd Hill Rd, Wilmington, VT 05363
/41
$674,000
- 3 Beds
- 3.5 Baths
- 2,472 Sq Ft
49 Greenspring Rd, Dover, VT 05356

Located in the desirable Greensprings neighborhood at Mount Snow Ski Resort, this spacious 3-bedroom, 4-bath townhome offers the perfect blend of mountain charm and modern comfort. The inviting interior features a soaring cathedral ceiling in the living room, anchored by a cozy wood-burning fireplace, creating the perfect après-ski retreat. A second family room adds flexibility, ideal for

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

49 Greenspring Rd, Dover, VT 05356
/27
$559,000
- 4 Beds
- 3 Baths
- 2,052 Sq Ft
69 Chapin Ln, Jamaica, VT 05343

Welcome to Sugar Chateau- Nestled in the serene landscape of Southern Vermont, this enchanting 4-bedroom log home offers the perfect blend of rustic charm and contemporary comfort. Embrace the warmth and character with exposed beams and a welcoming atmosphere. Enjoy the convenience of modern amenities in a rustic setting, featuring a recently renovated kitchen and bathrooms. Custom new Anderson

Tara van de Velde Four Seasons Sotheby's Int'l Realty

69 Chapin Ln, Jamaica, VT 05343
/48
$599,000
- 3 Beds
- 2.5 Baths
- 2,438 Sq Ft
456 Poverty Row, Whitingham, VT 05361

Lovely country setting on Poverty Row, a road name steeped in history, this builder’s home showcases quality craftsmanship and thoughtful design throughout. Set on 2.66 beautifully manicured acres with wild blueberry bushes and apple trees. Located on a paved public road, this property is less than five minutes from Lake Sadawga and Harriman Reservoir—perfect for boating, kayaking, and swimming.

Erica Reynolds Southern Vermont Realty Group

456 Poverty Row, Whitingham, VT 05361
/35
$629,000
- 3 Beds
- 2.5 Baths
- 1,882 Sq Ft
23 Joan's Ridge Rd, Dover, VT 05356

This beautifully maintained 3-bedroom, 2.5-bath contemporary home is located in the desirable Joan's Ridge community, just minutes from Mount Snow and the Hermitage Club. Step into a welcoming mudroom that leads to a cozy living room with a wood-burning fireplace, a dining area, and a fully equipped kitchen. The main level features a spacious primary ensuite bedroom for added convenience.

Jennifer Hovey-Densmore Deerfield Valley Real Estate

23 Joan's Ridge Rd, Dover, VT 05356
/29
$220,000
- 3 Beds
- 1 Bath
- 1,824 Sq Ft
14 Cherry Hill St, Bellows Falls, VT 05101

Located in the heart of Bellows Falls, Vermont, this charming 1880's home showcases classic 19th-century architecture. Set on a 0.30+/-acre lot, the property includes three bedrooms and one full bathroom. The open concept living and dining areas provide a welcoming space for gatherings, while the adjoining family room offers extra room for an office or flexible use. The full bathroom is

Rob Weltz Barrett and Valley Associates Inc.

14 Cherry Hill St, Bellows Falls, VT 05101
/16
$499,000
- 3 Beds
- 2.5 Baths
- 2,060 Sq Ft
3 Mill Rd, West Dover, VT 05356

When you picture a rustic and woodsy Vermont retreat, but with modern comforts, this is that home. Spacious chalet style home located conveniently on the MOOver shuttle route 3 miles from the Mount Snow Ski Resort. This 4 bedroom, 2.5 bath home has exposed natural woodwork throughout, a great open concept floor plan with large living room and updated gas fireplace on brick hearth, direct views of

Adam Palmiter Berkley & Veller Greenwood/Dover

3 Mill Rd, West Dover, VT 05356
/37
$365,000
- 4 Beds
- 1.5 Baths
- 2,115 Sq Ft
3432 Us Route 5, Westminster, VT 05158

A classic, stately Vermont Colonial wonderfully set on well over an acre of level land in Westminster, the oldest existing village in Vermont. This storied home was first the parsonage for the First Congregational Church, established in 1767. As was the custom of the time, the property was developed in phases. One of the first buildings was the large barn now situated behind the house, where

Bill Hickok Berkley & Veller Greenwood Country

3432 Us Route 5, Westminster, VT 05158
/27
$430,000
- 3 Beds
- 1.5 Baths
- 1,883 Sq Ft
2193 Old County Rd, West Halifax, VT 05358

This hidden gem is waiting for you. Come sit on your back deck and enjoy the view. This home has 3 bedrooms and 2 bathrooms; it sits on 10 acres of peace and quiet. If you enjoy the outdoors this offers hiking trails and access to ATV trails as well. This home also offers a full walk out basement, 2 car garage and plenty of storage in the basement, you could also finish off a room or two and

Peggy Winchester ACORN REAL ESTATE GROUP LLC

2193 Old County Rd, West Halifax, VT 05358
/40
$475,000 Open Sun 12PM - 2PM
- 3 Beds
- 2.5 Baths
- 2,800 Sq Ft
27 Grimes Hill Rd, Newfane, VT 05345

This may be the perfect house for you! Hidden from the road on 3.6+/ delightfully private acres of lawn and woods, you'll discover this truly enchanting New England home, fusing cape style with modern day convenience. The front door welcomes you from a delightful porch, offering shelter from the rain and snow. Once inside, you're greeted by a tiled mudroom entryway. Ahead is your three season

John Mcpherson Berkley & Veller Greenwood Country

27 Grimes Hill Rd, Newfane, VT 05345
/14
$1,750,000
- 4 Beds
- 3.5 Baths
- 2,698 Sq Ft
63 Sunbowl Ridge Rd Unit 63A, Stratton, VT 05360

The absolute best location in one of Stratton's most desirable communities!This four bedroom, three and one half bath townhome is located directly on the ski trail. Immaculate interior. Bright sunny interior with eastern and southern exposure. One car garage, family room, back patio with new hot tub. Private pool and hot tubs located a short walk away. Shuttle service to Stratton base area lifts

John Sikes Stratton Real Estate

63 Sunbowl Ridge Rd Unit 63A, Stratton, VT 05360
/27
$539,000
- 3 Beds
- 2.5 Baths
- 2,150 Sq Ft
16A Snow Tree Ln Unit Cedars 1, Dover, VT 05356

Rare Rare Rare! There are only 2 townhomes of this style at the desirable Snowtree development, and this particular 3 bedroom, 3 bath has been completely renovated. Walk out your private entry to the base area at Mount Snow via the convenient stream crossing bridge to access the magic carpet and tubing area, ideal for the ski season, but also any summer festivals. If someone doesn't ski they can

Adam Palmiter Berkley & Veller Greenwood/Dover

16A Snow Tree Ln Unit Cedars 1, Dover, VT 05356
/30
$399,000 Open House 5/03
- 3 Beds
- 2.5 Baths
- 1,617 Sq Ft
33 Frost Place, Brattleboro, VT 05301

Whether you're seeking a smart investment or a beautifully appointed primary residence, this exceptional offering in the heart of Brattleboro, VT, is not to be missed. Fully renovated by the current owners, this charming home offers far more than it's modest exterior suggests.Step onto the inviting screened porch — the perfect spot to unwind during warmer months or transition comfortably from the

Keith Nowak Four Seasons Sotheby's Int'l Realty

33 Frost Place, Brattleboro, VT 05301
/11
$495,000
- 3 Beds
- 3 Baths
- 2,400 Sq Ft
21 Howard St, Brattleboro, VT 05301

This beautiful Victorian home is just a short stroll from vibrant Brattleboro and has access to a huge town trail network. Nicely landscaped and has a partially fenced yard for pets or children. The house has lovely Victorian detailing and includes 3 covered porches. The formal entry has hardwood flooring, built-in bench w/mirror, period staircase, stained glass window and a 3/4 bath. The

Robert Doyle Berkley & Veller Greenwood Country

21 Howard St, Brattleboro, VT 05301
/46
$449,999
- 3 Beds
- 2 Baths
- 1,438 Sq Ft
1448 Cyrus Rd, Whitingham, VT 05361

Welcome to your perfect escape. This home has been beautifully maintained by the owners for 34 years. It has 3-bedrooms and 2-bathrooms. The homes nestled on a sprawling 15.2 acres complete with private hiking and ATV trails, a tranquil pond just steps from your front door, and breathtaking sunrise views from the porch, along with a large horse barn that has been partially converted into a

Peggy Winchester ACORN REAL ESTATE GROUP LLC

1448 Cyrus Rd, Whitingham, VT 05361

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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.