Windham County VT Homes for Sale

/48
$920,000
- 4 Beds
- 3.5 Baths
- 2,573 Sq Ft
573 Middletown Rd, Londonderry, VT 05148

Wonderful four bedroom home in the desirable town of Londonderry, Vermont. Once part of the Janeway Farm and Middletown Dairy this property has served as a primary home for many years. Spacious home has four bedrooms with three en-suite bedrooms. Land is suitable for gardens and room for play. There is a garden shed and a work shop just behind the house for any hobbies or projects. Living room

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

573 Middletown Rd, Londonderry, VT 05148
/38
$35,000
- 1 Bed
- 2 Baths
- 846 Sq Ft
103/05 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 8 unit consists of two adjoining units; Studio unit (105) Queen murphy bed and queen sleeper sofa, kitchenette and full bathroom. Hotel unit (103) Two queen beds and full bathroom. Units are located the mountain side of the hotel just above from a beautiful brook and just down the hallway from the Spa, ski locker,

Kelly Agrillo Southern Vermont Realty Group

103/05 Qtr.1,89 Grand Summit Way, Dover, VT 05356
/13
$150,000
- Land
- 4.68 Acres
- $32,051 per Acre
8559 Vt Route 30 Unit Lots 2 & 3, Jamaica, VT 05343

Waaaaait a minute! There’s buildable land just minutes from Stratton Mountain, and it’s already got septic not only approved, but basically installed?!?! I can just build my house on these 4.68 acres and enjoy all of the beauty and convenience of the area? And it's approved for 2 three bedroom houses!!! 2 miles to Stratton and 20 minutes to Manchester. I almost can’t believe this is

TG Glazer Winhall Real Estate

8559 Vt Route 30 Unit Lots 2 & 3, Jamaica, VT 05343
/34
$389,000
- 5 Beds
- 2 Baths
- 2,736 Sq Ft
5100 Vermont Route 100, Wardsboro, VT 05355

Nestled between the renowned Mount Snow and Stratton Mountain, this completely remodeled late 19th-century Colonial offers the perfect blend of historic charm and modern comfort. Meticulously renovated, the home has been torn down to the studs and reimagined with no detail overlooked. With all new windows, insulation, electrical, and plumbing, every inch of this home has been looked after with

Mike Masters Four Seasons Sotheby's Int'l Realty

5100 Vermont Route 100, Wardsboro, VT 05355
/33
$949,000
- 4 Beds
- 4 Baths
- 3,200 Sq Ft
9 Windham Way, Dover, VT 05356

This upgraded new style Greenspring townhome has direct views of Mount Snow and door to door shuttle service to and from the unit and the base area. A well updated 4+ bedroom, 4 bath unit with lots of bonus space, many recent updates and unique features. These include an open concept great room with vaulted ceiling, sunny exposure and sunset/ski trail views, wood burning fireplace with custom

Adam Palmiter Berkley & Veller Greenwood/Dover

9 Windham Way, Dover, VT 05356
/32
$549,000
- 3 Beds
- 3 Baths
- 2,139 Sq Ft
4A Junior's Way, Dover, VT 05356

This newly constructed 3-bedroom, 3-bath townhome, built in 2022, offers modern mountain living just minutes from the Mount Snow ski resort. With a convenient location, the slopes are minutes away and can easily be accessed via a short walk to the free MOOver Bus. The home boasts three levels of living, an open-concept design with a fireplace, spacious living and dining areas, a beautiful updated

Prema Fitzpatrick Skihome Realty

4A Junior's Way, Dover, VT 05356
/9
$225,000
- Land
- 0.73 Acre
- $308,219 per Acre
5 Pinnacle View Rd, Dover, VT 05356

With breathtaking views of Mount Snow, this exceptional 0.73-acre parcel is the perfect setting for your dream mountain retreat. Located in the resort district, short-term rentals are permitted, making this a prime investment opportunity or an ideal family legacy home for generations to enjoy. Just off Route 100, a one-minute drive to the lifts at Mount Snow,an Epic Pass mountain, offering

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

5 Pinnacle View Rd, Dover, VT 05356
/45
$650,000
- 3 Beds
- 3 Baths
- 2,341 Sq Ft
49 High Point Dr Unit A122, Stratton, VT 05360

Crown Point, Stratton Vermont. Enjoy this two-level, three bedroom, three bath condo. This home has an upper and lower entry, both with plenty of storage for outdoor gear. The upper level opens into the kitchen, dining area, and living room with wood burning fireplace and a small deck. The primary ensuite bedroom, with a jacuzzi tub, is also on the upper level. The lower level has a second living

Mike England Michael England Real Estate

49 High Point Dr Unit A122, Stratton, VT 05360
/18
$495,000
- 2 Beds
- 2 Baths
- 1,900 Sq Ft
106 Silver Birch Unit 17H, Dover, VT 05356

This 2 bedroom, plus bunkroom, end unit condo is located across the road from the Mt. Snow ski area. There is a shuttle to the mountain that will allow you to be free from driving and parking fees. Relax in your private hot tub after a day on the slopes or sit on this spacious deck an enjoy the view. A cozy wood-burning fireplace sets the mood for your apre' ski afternoon. On a rainy or

Regina Perrotto Skihome Realty

106 Silver Birch Unit 17H, Dover, VT 05356
/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
/25
$519,000
- 3 Beds
- 3 Baths
- 1,850 Sq Ft
19A Kingswood Rd, Dover, VT 05356

This three-bedroom plus den townhome boasts an exceptional location only steps from the Kingswood Community Center and an easy shuttle ride to Mount Snow. This townhome features 3 full bathrooms, vaulted ceilings, a wood-burning fireplace, an open-concept living/dining space, and a private deck with wooded views and outdoor hot tub. This home offers a perfect blend of comfort and convenience. The

Melissa Ellis Southern Vermont Realty Group

19A Kingswood Rd, Dover, VT 05356
/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
/6
$109,000
- Land
- 1.78 Acres
- $61,236 per Acre
0000 Wonder Ln Unit Lot 18, Jamaica, VT 05343

Prime 1.78-Acre Wooded Lot near Stratton Mountain Ski Resort and Golf Course---Nestled in a serene and private subdivision, this magnificent 1.78-acre wooded lot offers an unparalleled opportunity to build your dream home amidst Vermont's natural beauty. Located conveniently close to the renowned Stratton Mountain Ski Resort and Golf Course, this property promises year-round recreation and

Rachel Febbie EXP Realty

0000 Wonder Ln Unit Lot 18, Jamaica, VT 05343
/7
$99,000
- Land
- 2.06 Acres
- $48,058 per Acre
000 Wonder Ln Unit LOT 15, Jamaica, VT 05343

Prime 2.06-Acre Wooded Lot near Stratton Mountain Ski Resort and Golf Course---Nestled in a serene and private subdivision, this magnificent 2.08-acre wooded lot offers an unparalleled opportunity to build your dream home amidst Vermont's natural beauty. Located conveniently close to the renowned Stratton Mountain Ski Resort and Golf Course, this property promises year-round recreation and

Rachel Febbie EXP Realty

000 Wonder Ln Unit LOT 15, Jamaica, VT 05343
/39
$1,488,000
- 6 Beds
- 3 Baths
- 5,000 Sq Ft
34 E Village Cir, Wilmington, VT 05363

Stunning Rustic Retreat with Modern Comforts. Nestled in a peaceful, partially wooded lot, this property exudes character and charm. Fully renovated in 2013, it’s been meticulously maintained and offers an inviting, cozy atmosphere. Practicality meets style with a large mudroom and laundry area that includes slate and tile flooring w/ radiant heat. A massive great room has a fieldstone fireplace,

Richard Caplan Deerfield Valley Real Estate

34 E Village Cir, Wilmington, VT 05363
/16
$319,000
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
12E Dover Green Loop Unit 12E, Dover, VT 05356

Renovated townhome in the Dover Green community located just a short drive or shuttle ride south of Mount Snow. This spacious unit overlooks a pond and nice sunny exposure thanks to recent clearing, and has easy access to parking and the side yard. Inside is an open concept floor plan with vaulted great room, wood burning fireplace and brick hearth, a large eat in kitchen with new cabinets,

Adam Palmiter Berkley & Veller Greenwood/Dover

12E Dover Green Loop Unit 12E, Dover, VT 05356
/24
$650,000
- 5 Beds
- 2 Baths
- 1,530 Sq Ft
48 Upper Highlands, Dover, VT 05356

Unique opportunity to own an updated and woodsy chalet just up from the slopes of Mt Snow, yet also with direct snowmobile trail access. This 5 bedroom, 2 bath home has been tastefully renovated while maintaining the charm and character befitting a Vermont retreat ski home. The interior features an open concept living space with vaulted great room, wood burning fireplace, natural woodwork and

Adam Palmiter Berkley & Veller Greenwood/Dover

48 Upper Highlands, Dover, VT 05356
/21
$609,000
- 2 Beds
- 2 Baths
- 916 Sq Ft
771 Stratton Mountain Access Rd Unit 261, Stratton, VT 05360

771 Stratton Mountain Access Rd, Stratton, VT 05155Long Trail House is Stratton’s #1 location for owners who wish to combine personal use with an optional rental offset when not in residence. Walk to Village shops, restaurants and ski lifts. The floor plan for Long Trail House #261 is one of the largest of the 2 bedroom layouts. Master bedrooms has nice views of the Village Common. Great

Andrew King Stratton Real Estate

771 Stratton Mountain Access Rd Unit 261, Stratton, VT 05360
/58
$1,338,000
- 4 Beds
- 3.5 Baths
- 3,400 Sq Ft
1845 Hatch School Rd, Brattleboro, VT 05301

Stunning Contemporary Farmhouse with Expansive Grounds & Ultimate Privacy. Nestled in the heart of nature, this beautifully designed contemporary farmhouse offers the perfect blend of modern comfort and rustic charm. Set on a sprawling property with open fields, mature maple trees, and two serene ponds. Stone walls, a stone barn, and an orchard add to the picturesque landscape. The home features

Richard Caplan Deerfield Valley Real Estate

1845 Hatch School Rd, Brattleboro, VT 05301
/13
$749,000
- Land
- 2.57 Acres
- $291,440 per Acre
Lot 3 Old Mill Ln, Wilmington, VT 05363

Discover an exceptional opportunity to own a 2.57 acre parcel of land located in an exclusive private neighborhood adjacent to the renowned private ski resort, The Hermitage Club in Wilmington, Vermont. This premium lot is the perfect canvas for creating your dream mountain retreat with custom homes to be crafted by the Wadsworth Design Build, a leading builder in Southern Vermont. Enjoy the

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

Lot 3 Old Mill Ln, Wilmington, VT 05363
/19
$749,000
- Land
- 1.22 Acres
- $613,934 per Acre
Lot 2 Old Mill Ln, Wilmington, VT 05363

Discover an exceptional opportunity to own a 1.22-acre parcel of land located in an exclusive private neighborhood adjacent to the renowned private ski resort, The Hermitage Club in Wilmington, Vermont. This premium lot is the perfect canvas for creating your dream mountain retreat with custom homes to be crafted by the Wadsworth Design Build, a leading builder in Southern Vermont. Enjoy the

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

Lot 2 Old Mill Ln, Wilmington, VT 05363
/15
$774,000
- Land
- 3.60 Acres
- $215,000 per Acre
Lot 5 Old Mill Ln, Wilmington, VT 05363

Discover an exceptional opportunity to own a 3.6 acre parcel of land located in an exclusive private neighborhood adjacent to the renowned private ski resort, The Hermitage Club in Wilmington, Vermont. This premium lot is the perfect canvas for creating your dream mountain retreat with custom homes to be crafted by the Wadsworth Design Build, a leading builder in Southern Vermont. Enjoy the

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

Lot 5 Old Mill Ln, Wilmington, VT 05363
/36
$998,500
- 4 Beds
- 3.5 Baths
- 2,070 Sq Ft
32 Shattarack Rd Unit B5, Stratton, VT 05360

Ski-in, ski-out Slopeside Townhouse! This meticulously remodeled offers everything you need for an exceptional mountain lifestyle. Inside, you’ll find your choice of two ensuite primary bedrooms, along with two additional spacious bedrooms, providing ample room and privacy for family and guests. Two bedrooms are enhanced with custom-built-ins, blending functionality with stylish design. The

Timothy Apps Four Seasons Sotheby's Int'l Realty

32 Shattarack Rd Unit B5, Stratton, VT 05360
/33
$725,000
- 3 Beds
- 3.5 Baths
- 2,400 Sq Ft
83B Greenspring, Dover, VT 05356

Imagine stepping into a pristine mountain townhome that feels like a warm embrace, complete with modern updates and breathtaking views of the surrounding peaks. The moment you enter, a spacious mudroom welcomes you, perfectly designed to accommodate all your outdoor gear and winter jackets. This three-bedroom plus den, 3.5-bath gem boasts a sun-drenched open floor plan where the living and dining

Sheila Joyce-Albano Skihome Realty

83B Greenspring, Dover, VT 05356
/25
$895,000
- 4 Beds
- 3 Baths
- 2,546 Sq Ft
19 Village Rd E, Wilmington, VT 05363

Here is a chance to own a home directly across the street from the private Hermitage Ski Club with easy access to the resort, snowmobile trails, the Mount Snow ski resort, nearby country villages for shopping and dining, and gorgeous area lakes. This lovely renovated chalet sits on a level with ample parking thanks to a circular driveway, winter exposure to Haystack Mountain Peak, a shed for

Adam Palmiter Berkley & Veller Greenwood/Dover

19 Village Rd E, Wilmington, VT 05363
/42
$2,000,000
- 6 Beds
- 4.5 Baths
- 4,950 Sq Ft
43 Upton Rd, Dover, VT 05356

The best of both worlds... High end luxury in this Post & Beam home on a private 35+ acre wooded lot with direct ski trail views of Mount Snow, yet just over a mile to the ski area. It's nearly impossible to find this kind of privacy so near mountain. This spectacular 6 bedroom, 4.5 bath Post & Beam home was built in 2007 and no expense was spared in the construction. Features include a high end

Adam Palmiter Berkley & Veller Greenwood/Dover

43 Upton Rd, Dover, VT 05356
/22
$345,000
- 3 Beds
- 1.5 Baths
- 1,100 Sq Ft
7224 Vermont Route 100, Wardsboro, VT 05360

Lovely updated efficient chalet on 10 acres just up from the main entrance to Mount Snow. This cute home has great functional space without being overly large to maintain. The current owners have recently updated the heating system, roof, kitchen, bath, etc, to afford turn key enjoyment. Enter to a large great room with updated kitchen and breakfast bar, living room with wood stove, propane

Adam Palmiter Berkley & Veller Greenwood/Dover

7224 Vermont Route 100, Wardsboro, VT 05360
/20
$169,000
- 2 Beds
- 1 Bath
- 336 Sq Ft
181 Townshend Dam Rd, Wardsboro, VT 05355

This is a 4 acre lot with two different older mobile home trailers. Addresses are 181 and 203 Townshend Dam Road, Wardsboro. One shared drilled well, two separate septic's. One lot has a 2bedroom 1bath trailer and the other is a 1bedroom, 1bath trailer. Both are currently rented. One tenant will be moving out in January 2025, the other is occupied. This is a nice level lot with the potential to

Julie Lowe Lowe's Real Estate, LLC

181 Townshend Dam Rd, Wardsboro, VT 05355
/19
$215,000
- 3 Beds
- 1 Bath
- 636 Sq Ft
30 Water St, Jamaica, VT 05343

Discover the Acorn, a picturesque retreat nestled on the banks of the scenic West River in Jamaica, Vermont. This unique home, a beautifully converted sugar shack, offers an enchanting taste of rustic charm, perfect for those seeking a serene getaway. Ideal for nature lovers and outdoor enthusiasts, the Acorn sits close to the renowned ski resorts of Stratton Mountain and Mount Snow, providing a

Daire Gibney Barrett and Valley Associates Inc.

30 Water St, Jamaica, VT 05343
/42
$875,000
- 4 Beds
- 3.5 Baths
- 3,553 Sq Ft
37 Pleasant View Ln, Wilmington, VT 05363

Seeking an upscale but also rustic, Vermont retreat? Looking for privacy but convenience to amenities? Love a water feature and a mountain view? Need a place to host large gatherings but also cozy enough for a romantic weekend getaway? This is just the place. Tucked away on a private road sits this spacious 4 bedroom, 3.5 bath, true log home with an excellent layout over 3 finished floors. All

Jacki Murano Southern Vermont Realty Group

37 Pleasant View Ln, Wilmington, VT 05363
/30
$460,000
- 2 Beds
- 2 Baths
- 1,127 Sq Ft
27 Haymaker Ln Unit 9H, Wilmington, VT 05363

Cozy convenience on Haystack Mountain adjacent to The Hermitage Club and just a short drive to Mount Snow and downtown Wilmington. This 2 bedroom/2 bathroom unit has an open living space perfect for entertaining and highlighted by the fieldstone fireplace ambiance to warm you apres ski/hike or snowshoe. The unit is being offered furnished and ready to enjoy this season and year round with access

Cordelia Garofalo Deerfield Valley Real Estate

27 Haymaker Ln Unit 9H, Wilmington, VT 05363
/13
$180,000
- Land
- 64 Acres
- $2,795 per Acre
582 Hartley Hill Rd, Westminster, VT 05158

Near the crest of Hartley Hill, 64 acres of wooded land offers a peaceful country setting, with westerly views, ideal for a primary or a vacation home. With some selective clearing, a suitable building site could be located at the front of the lot, backed by a beautiful ridge and ample trees for future firewood. Located in Westminster, an easy commute to the village of Saxtons River, home to VT

Heidi Bernier Berkley & Veller Greenwood Country

582 Hartley Hill Rd, Westminster, VT 05158
/27
$749,000
- 4 Beds
- 3.5 Baths
- 3,360 Sq Ft
32 Circle View Dr, Dover, VT 05356

Gorgeous new construction home just completed and ready for immediate use this season. This lovely home sits just up from the Valley Trail in the heart of Dover with very easy access off a paved road, and near to the Mount Snow resort and golf course. The interior features gorgeous wood floors and exposed natural woodwork throughout, a custom kitchen with granite counters, stainless appliances,

Adam Palmiter Berkley & Veller Greenwood/Dover

32 Circle View Dr, Dover, VT 05356
/46
$2,999,000
- 7 Beds
- 7.5 Baths
- 8,718 Sq Ft
1324 Middle Rd, Brattleboro, VT 05301

Truly a rare and remarkable property. This custom home was lovingly designed and constructed in 2005 with a clear vision for bringing the Vermont scenery in, while maintaining the rustic charm befitting a country estate. The main house features gorgeous exposed timber frame construction throughout, natural wood flooring, paneling, and trim, extensive artisan stonework inside and out, including 3

Adam Palmiter Berkley & Veller Greenwood/Dover

1324 Middle Rd, Brattleboro, VT 05301
/27
$499,000
- 1 Bed
- 1 Bath
- 841 Sq Ft
19 Village Lodge Rd Unit 304, Stratton, VT 05155

It’s all about location! Landmark is located within Stratton Mountain Resorts iconic clock tower, nestled within the heart of the village. This 1 bedroom plus bonus room, 1 bath Landmark unit is at the center of all that Stratton Mountain has to offer and is walking distance to village restaurants and shops. Enjoy the ease of two parking spaces, one on the upper deck and another one in the

MaryKate Grey Stratton Real Estate

19 Village Lodge Rd Unit 304, Stratton, VT 05155
/26
$949,000
- 5 Beds
- 4.5 Baths
- 3,419 Sq Ft
37 Carinthia Rd, Dover, VT 05356

Rare opportunity to own a townhome at the base of Carinthia at Mt Snow. Stroll directly to and from the gorgeous brand new Carinthia base lodge for skiing, food, drinks, and terrain events, with easy access to the trails. This 5 bedroom, 4.5 bath townhome features open concept living space, tremendous natural light, vaulted living room with wood burning brick fireplace, a large open kitchen with

Adam Palmiter Berkley & Veller Greenwood/Dover

37 Carinthia Rd, Dover, VT 05356
/60
$159,000
- 3 Beds
- 2 Baths
- 1,392 Sq Ft
7 Deepwood Park, Brattleboro, VT 05301

Price improvement!!! Charming one level mobile home with addition in Tri Park Co-op. 3 bedrooms, 2 bathrooms, eat in kitchen, large living room, den/other room, large back deck for entertaining and BBQs and a full concrete foundation!!! Great property! Don't miss this opportunity! Seller to pay buy in fee to the park for buyer at time of closing!!!

Emily Lagerberg R.H. Thackston & Company

7 Deepwood Park, Brattleboro, VT 05301
/4
$250,000
- Land
- 1.57 Acres
- $159,236 per Acre
0 Gold Medal Cir Unit Lot 1 5023219, Stratton, VT 05155

This is lot #1 in the Powers Subdivision, which is the closest lot to Mountain Rd, giving you access to Stratton's Sunbowl entrance less than a mile away. Lot #1 is 1.57 acres and has views of Stratton Mountain. This Gold Medal Circle area of the Powers Subdivision has 11 lots, 2.71 acres of common land with a pond, and 69.06 of conservation land. Permits are in place with the State of Vermont

Ross Powers TPW Real Estate

0 Gold Medal Cir Unit Lot 1 5023219, Stratton, VT 05155
/54
$384,000
- 3 Beds
- 1.5 Baths
- 1,400 Sq Ft
24 Blackberry Lane Private, Dover, VT 05356

Just in time for ski season, this cozy and pristine Amish-built expanded 3-bedroom plus loft log cabin offers the perfect blend of rustic charm and modern comfort, located just minutes from Mount Snow. The thoughtfully designed floor plan includes a full bedroom and bath on the first level as well as laundry, a wonderful loft, and an additional sitting room with a propane stove, creating a warm

Erica Reynolds Southern Vermont Realty Group

24 Blackberry Lane Private, Dover, VT 05356
/30
$579,000
- 5 Beds
- 3 Baths
- 2,566 Sq Ft
1 Dorr Fitch Rd, Dover, VT 05356

Charming, colonial home with landscaped gardens, stonewalls, and expansive views, and located in the village. This delightful property has many updates and offers a wonderful view over a field to enjoy the beauty of the small village and great decks to enjoy the river, trees, and fields. The property has easily accessed paved town roads and a flat open driveway with parking for 5+ cars. Features

Derek Greene Derek Greene

1 Dorr Fitch Rd, Dover, VT 05356

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