Windham County VT Homes for Sale

/37
$699,000
- 3 Beds
- 3 Baths
- 1,400 Sq Ft
5Q Northbrook Village Rd Unit A33, Dover, VT 05356

One of a kind opportunity to be trailside at Mount Snow. This is a lofted 3 bedroom, 3 bath unit, and is one of the closest buildings at Seasons to the newly renovated amenities, meaning you can go to the pools, gym, hot tubs, and more, without having to get in your car on days when you take a break from skiing. Enjoy the large vaulted living space with stone floor to ceiling wood burning

Adam Palmiter Berkley & Veller Greenwood/Dover

5Q Northbrook Village Rd Unit A33, Dover, VT 05356
/38
$499,000
- 3 Beds
- 2 Baths
- 1,300 Sq Ft
156 Mountain View Rd, Wilmington, VT 05363

This charming Cape-style home offers three bedrooms and two full baths across the first two floors, featuring hardwood floors throughout and abundant natural light. Upstairs bedrooms have built in dressers. The living room boasts a cozy gas fireplace and flows seamlessly into the open-concept kitchen and dining area. A MAJOR highlight is the deeded lake rights to the picturesque Lake Raponda in

Jennifer Hovey-Densmore Deerfield Valley Real Estate

156 Mountain View Rd, Wilmington, VT 05363
/59
$375,000
- 2 Beds
- 1 Bath
- 828 Sq Ft
1171 Wickopee Hill Rd, Dummerston, VT 05301

Serenity now! Fall in love with this peaceful retreat where every element has been lovingly and artistically designed, nurtured, and enhanced to the utmost of its beautiful and natural potential. The property features TWO inviting houses, a charming barn-style garage, and stunning established gardens overflowing with flowers, fruits, and vegetables—seven fruit trees, six blueberry bushes,

Stephanie Peduzzi-Baker Brattleboro Area Realty

1171 Wickopee Hill Rd, Dummerston, VT 05301
/18
$176,500
- 2 Beds
- 1 Bath
- 888 Sq Ft
15 Lynwood Dr, Brattleboro, VT 05301

This is absolutely NOT your ordinary Mobile Home! The original steel frame is the only remaining component of the mobile home. Completely rebuilt from the floor up with wood framing, windows, doors and insulation. This fully fenced leased lot has two sheds, a 1 car garage building with tons of storage and a workshop building with its own mini-split for heat and AC. The tastefully renovated

Chris Long BHG Masiello Brattleboro

15 Lynwood Dr, Brattleboro, VT 05301
/31
$415,000
- 3 Beds
- 3.5 Baths
- 2,188 Sq Ft
195 Mann Rd Unit 12, Wilmington, VT 05363

Contemporary Townhouse on Haystack Golf Course. Beautifully situated along the 11th fairway of the Haystack Golf Course, this contemporary townhouse offers stunning mountain views and peaceful sunrises right from your private deck. The bright and airy main living level features an open-concept design with vaulted ceilings, a wood-burning fireplace, a spacious dining area, and a well-appointed

Monique White Deerfield Valley Real Estate

195 Mann Rd Unit 12, Wilmington, VT 05363
/31
$499,000
- 3 Beds
- 2 Baths
- 2,372 Sq Ft
285 Chimney Hill Rd, Wilmington, VT 05363

Contemporary retreat in the heart of Chimney Hill. Set on a double lot along a paved road offering the perfect balance of comfort, style and year round convenience. Located just minutes from Wilmington village, Lake Whitingham, Mount Snow and scenic trail that leads to the summit of Haystack Peak in the Green mountain National Forest. The bright, open concept interior is filled with natural

Monique White Deerfield Valley Real Estate

285 Chimney Hill Rd, Wilmington, VT 05363
/60
$899,000
- 5 Beds
- 4.5 Baths
- 5,000 Sq Ft
42 Blackberry Ln, Jamaica, VT 05343

Idyllic, Picturesque, Expansive, Vast Family Farm with outbuildings and Large Farmhouse! Known to some as Sweet Berry Farm the blueberries and blackberries are plentiful along with many other productive fruits trees, a grove of 20 mature apple trees with many over 30 years old, , flowers and veggies in the gardens. This location just off of Route 30 is perfect for ALL of your Vermont dreams and

Steve Goldfarb Deerfield Valley Real Estate

42 Blackberry Ln, Jamaica, VT 05343
/8
$165,000
- Land
- 1.20 Acres
- $137,500 per Acre
4769 Pikes Falls Rd, Jamaica, VT 05143

A Rare Vermont Gem:This 1.2-acre parcel offers what few can—a front-row seat to one of Southern Vermont’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this property is the equivalent of what would be Vermont’s oceanfront real estate.A wooded path leads directly from the land to the pristine falls, which are preserved by the

Rachel Febbie EXP Realty

4769 Pikes Falls Rd, Jamaica, VT 05143
/54
$365,000
- 4 Beds
- 3.5 Baths
- 3,147 Sq Ft
3523 Westminster Rd W, Putney, VT 05346

Circa 1800, this storied building began its life as a humble general store and inn, a hub of commerce, a refuge for travelers and townsfolk alike, this structure has witnessed the sweep of over two centuries. Today, it stands lovingly restored, as a primary residence—The store’s original counters and shelves (once lined with bins of dried goods and glass jars of penny candy) still remain. Many

Heidi Bernier Berkley & Veller Greenwood Country

3523 Westminster Rd W, Putney, VT 05346
/19
$299,000
- 3 Beds
- 1 Bath
- 1,500 Sq Ft
85 Crosby St, Brattleboro, VT 05301

Charming 1950s Gem! Step into timeless warmth and character with this delightful 3-bedroom, 1-bath home. This lovingly cared for home features beautiful rock maple hardwood floors, solid wood doors, and rich original woodwork that speak to its enduring craftsmanship. Recent updates blend vintage charm with modern comfort, including fresh interior and exterior paint, standing seam metal roof,

Karen Hoppe Berkley & Veller Greenwood Country

85 Crosby St, Brattleboro, VT 05301
/35
$454,000
- 4 Beds
- 2.5 Baths
- 1,374 Sq Ft
38 Snow Rd, Dover, VT 05356

Quintessential Vermont chalet with stunning southern views over rolling meadows and distant ridgelines without a neighbor in sight. Privately nestled in a serene country setting, this sweet chalet exudes warmth and character with wood flooring, a classic fieldstone wood-burning fireplace, exposed beam ceilings, and a sunlit dining area. The main level includes a thoughtfully updated kitchen with

Monique White Deerfield Valley Real Estate

38 Snow Rd, Dover, VT 05356
/39
$296,000
- 1 Bed
- 1 Bath
- 640 Sq Ft
305 Missing Link Rd, Bellows Falls, VT 05101

Tucked away on 1.3 peaceful acres with 600 feet of Connecticut River frontage, this cozy 1-bedroom, 1-bathroom cabin offers the perfect blend of privacy and convenience. With just over 600 square feet of living space, this semi-off-grid retreat features propane heat, spring water hookup, and a composting toilet ideal for simple, sustainable living. However, there is full electric service for your

Sara Zumbruski EXP Realty

305 Missing Link Rd, Bellows Falls, VT 05101
/34
$125,000
- Land
- 1.31 Acres
- $95,420 per Acre
118 Chimney Hill Rd, Wilmington, VT 05363

Brand new Quad Lot right on Chimney Hill Road! Former lots M118 & M119 have had two additional parcels added on each end to form a 1.31-Acre Lot suitable for a three-bedroom single family home. Build your dream home and live the all-season resort lifestyle. Chimney Hill Owners Association is located on 1,200 acres adjacent to the Green Mt. National Forest, with 550 acres owned in common by the

Sigrid Pickering Chimney Hill Realty

118 Chimney Hill Rd, Wilmington, VT 05363
/18
$325,000
- 3 Beds
- 1 Bath
- 1,174 Sq Ft
138 Cedar St, Brattleboro, VT 05301

Welcome to this adorable 3-bedroom, 1-bath ranch-style home nestled in one of Brattleboro's most sought-after neighborhoods! Built in 1956, this lovingly cared for gem perfectly blends classic character with modern comfort. Many recent upgrades including CertainTeed Monogram vinyl siding and trim, freshly painted interior walls and so much more. The kitchen features a sleek Whirlpool glass top

Claire Renaud Berkley & Veller Greenwood Country

138 Cedar St, Brattleboro, VT 05301
/32
$799,000
- 4 Beds
- 2 Baths
- 2,160 Sq Ft
3581 Houghtonville Rd, Grafton, VT 05146

Located in a historic district at the edge of one of southern Vermont's most beautiful and vibrant villages, this property is a true Green Mountain Dream. The sellers purchased it as a vacation home, fell in love with it and moved there full time, renovating and expanding the home to blend classic Vermont charm with a modern lifestyle. Forced to return to their former location to maintain a

Steve Stettler Four Seasons Sotheby's Int'l Realty

3581 Houghtonville Rd, Grafton, VT 05146
/23
$499,000
- 3 Beds
- 2.5 Baths
- 1,548 Sq Ft
28 Lightning Ledge Way, Wilmington, VT 05363

Private 2004 country chalet in the Chimney Hill community just outside the village of Wilmington. Hiking trails, snowmobile trail access, and convenient nearby snowmobile trailer parking, make this super convenient for the outdoorsy. This home sits on a rare double lot, just up from the beautifully renovated Chimney Hill clubhouse, Lake Whitingham, and Mount Snow ski resort, affording year round

Adam Palmiter Berkley & Veller Greenwood/Dover

28 Lightning Ledge Way, Wilmington, VT 05363
/19
$450,000
- 4 Beds
- 3.5 Baths
- 1,800 Sq Ft
16 Tenth Unit 40, Wilmington, VT 05363

Beautiful 4 bedroom, 3.5 bath townhouse just off the Hermitage Club Golf Course with easy access to trails, the village of Wilmington, lakes, and the nearby Hermitage Club Ski Area and Mount Snow. The deck overlooks the 10th green and is beyond typical driving distance, so you can enjoy the sun while watching play. This unit has been updated including new carpet, new high efficiency wood stove in

Adam Palmiter Berkley & Veller Greenwood/Dover

16 Tenth Unit 40, Wilmington, VT 05363
/53
$475,000
- 3 Beds
- 3 Baths
- 2,463 Sq Ft
1591 Higley Hill, Marlboro, VT 05344

Wonderful home on 11.2 acres in a peaceful setting on Higley Hill in Marlboro. The main level boasts a beautiful family room addition with lots of windows and a gas fireplace, galley kitchen with stainless appliances, dining area, 3/4 bath with laundry, living room with gas stove, 3/4 bath with sitting area and a primary bedroom with ensuite full bath. A loft area that can be used as a bedroom or

Jennifer Hovey-Densmore Deerfield Valley Real Estate

1591 Higley Hill, Marlboro, VT 05344
/34
$699,000
- 5 Beds
- 4 Baths
- 4,700 Sq Ft
233 Poverty Row, Whitingham, VT 05361

What a gem! This absolutely meticulously maintained 2015 farmhouse sits just up from Lake Sadawga and Harriman Reservoir on a private 2 acre parcel off a paved road. The curb appeal is beyond what most can dream of with gorgeous perennial gardens, split rail fencing, ample yard space, and total privacy. Features include a beautiful open floor plan with large living room and family room, wood

Adam Palmiter Berkley & Veller Greenwood/Dover

233 Poverty Row, Whitingham, VT 05361
/40
$809,000
- 3 Beds
- 3 Baths
- 3,606 Sq Ft
46 Scattered Timber Rd, Wilmington, VT 05363

Escape to the Green Mountains with this custom-built Moose Head Cedar Log Cabin, beautifully sited on a private wooded lot in the sought-after Chimney Hill community. Enjoy ridgeline views, peaceful surroundings, and the fresh Vermont air. Inside, the offers timeless craftsmanship and open-concept living, featuring soaring post and beam construction with vaulted ceilings, floor-to-ceiling windows

Monique White Deerfield Valley Real Estate

46 Scattered Timber Rd, Wilmington, VT 05363
/53
$1,525,000
- 3 Beds
- 3.5 Baths
- 5,105 Sq Ft
3333 Under the Mountain Rd, Londonderry, VT 05148

Perched gracefully along one of Vermont’s most storied and picturesque country roads, 3333 Under the Mountain Road is a rare and refined offering in the heart of South Londonderry. Encompassing 40 serene acres with sweeping panoramic views across sunlit valleys and distant resort ridgelines, this remarkable estate captures the very essence of elevated mountain living.The residence itself

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

3333 Under the Mountain Rd, Londonderry, VT 05148
/5
$170,000
- Land
- 16 Acres
- $10,759 per Acre
0 Hall Rd, Marlboro, VT 05363

This is a rare 15.8 acre offering located in the pastoral town of Wilmington, Vermont. Featuring wooded terrain, with the Beaver Brook running through the lower section of the property. With stone walls, power/cable/high speed internet running through the lot, and driveway frontage on Hall Rd., this property offers privacy and beauty. In addition, the land is close to Mount Snow and the

Lisa Mirando Deerfield Valley Real Estate

0 Hall Rd, Marlboro, VT 05363
/27
$995,000
- 4 Beds
- 3.5 Baths
- 3,000 Sq Ft
6B Foliage Ln, Dover, VT 05356

Stunning renovated Kingswood townhome located conveniently between Mount Snow and the Hermitage Club Resorts in Southern VT. This beautifully updated 4 bedroom, 3.5 bath townhome was built in 2006 and renovated to a bold contemporary style in 2020 by the current owners. No expense was spared at making this a true dream getaway. Upon entry you are greeted by a large, functional mudroom complete

Adam Palmiter Berkley & Veller Greenwood/Dover

6B Foliage Ln, Dover, VT 05356
/43
$1,738,000
- 5 Beds
- 4.5 Baths
- 4,300 Sq Ft
36 A or B Boulder Ridge Dr, Dover, VT 05356

The new ownership/development team at Boulder Ridge is pleased to announce the commencement of the next phase of construction at this unique location. Two minutes to the base of Mount Snow, awe-inspiring year-round views of the slopes of Mount Snow as well as the vast Deerfield Valley, combined with the distinct trails of the Hermitage Club in the distance (a 7 minute drive) are just a few of

John Redd Skihome Realty

36 A or B Boulder Ridge Dr, Dover, VT 05356
/9
$80,250
- Land
- 3.10 Acres
- $25,887 per Acre
0 E Orchard St Unit 5047716, Brattleboro, VT 05301

A rare opportunity to purchase a lot in a highly desirable Brattleboro neighborhood. This 3+ acre wooded parcel features a mature pine forest with additional hardwoods intermixed, stonewalls and even a small stream. It's the location that makes this property unique. Just up the road from the Brattleboro Country Club on a quiet street that gives quick access to all that Brattleboro and the

Bill Hickok Berkley & Veller Greenwood Country

0 E Orchard St Unit 5047716, Brattleboro, VT 05301
/34
$289,000
- 2 Beds
- 1.5 Baths
- 1,059 Sq Ft
394 Haystack Rd Unit 2, Wilmington, VT 05363

Enjoy four-season living in this inviting 2-bedroom, 1.5-bath townhome just a short walk to Haystack Golf Course. Set in a peaceful location with direct Valley Trail and snowmobile access, this well-cared-for home is part of a small HOA with low fees. The main level offers a spacious open layout featuring a cozy wood stove on a slate hearth—perfect for watching the fire roar after a day on the

Chad Lackey Deerfield Valley Real Estate

394 Haystack Rd Unit 2, Wilmington, VT 05363
/51
$989,000
- 3 Beds
- 2.5 Baths
- 3,100 Sq Ft
111 Cooper Hill Rd, Dover, VT 05341

Perched atop scenic Cooper Hill in Dover, Vermont, this welcoming 3-bedroom, 3-bath home is set on over 10 acres with sweeping Mountain views and unforgettable sunrises. The spacious open concept living area and kitchen are ideal for gathering, featuring wood floors, abundant natural light, and a cozy wood burning stove that anchors the space. A generous first floor primary suite offers comfort

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

111 Cooper Hill Rd, Dover, VT 05341
/38
$1,750,000
- 4 Beds
- 3.5 Baths
- 2,862 Sq Ft
161 Depot Rd, Williamsville, VT 05362

Perched high above the enchanting hills of Newfane, VT, lies a truly one-of-a-kind property. This meticulously crafted home offers an off-grid, private retreat with breathtaking views of the surrounding landscape. Constructed in 2003, the post and beam design incorporates wood and stone harvested from its expansive219-acre setting, showcasing a harmonious blend of nature and architecture. This

Keith Nowak Four Seasons Sotheby's Int'l Realty

161 Depot Rd, Williamsville, VT 05362
/7
$499,000
- Land
- 30 Acres
- $16,633 per Acre
Lot X Tyanoga Rd, Whitingham, VT 05361

Spectacular opportunity to own a rare waterfront building lot on Lake Sadawga in Southern Vermont. This lot sits on a private dead end corner with southern exposure, private lake frontage including an earthen dam, and easy access along this pristine, natural lake. There is additional frontage along Stimpson Hill Road. The lake offers tremendous fishing, kayaking, canoeing, water sports, and

Adam Palmiter Berkley & Veller Greenwood/Dover

Lot X Tyanoga Rd, Whitingham, VT 05361
/39
$925,000
- 4 Beds
- 4 Baths
- 3,200 Sq Ft
9D Dover Springs Ln, Dover, VT 05356

Stunning updated Greenspring unit, just across the street from the Mount Snow ski resort with stunning direct views of the ski trails. This 4 bedroom, 4 bath unit features extensive upgrades, new furnishings, and immaculate condition, to ensure turn key enjoyment. Features include an open concept great room with vaulted ceiling and wood burning two sided fireplace, sunny exposure and sunset/ski

Adam Palmiter Berkley & Veller Greenwood/Dover

9D Dover Springs Ln, Dover, VT 05356
/28
$1,395,000
- 4 Beds
- 4.5 Baths
- 3,476 Sq Ft
3B Freestyle Cir, Dover, VT 05356

Trailside luxury at the base of the Mount Snow ski resort just off the Snowdance ski trail. This spectacular 2016 unit is just about as close and turn key as you can find. Amazing convenience to the mountain thanks to direct ski trail access, affording the ability to stop by to warm up or get a bite, yet with easterly views and a size usually only found in off mountain properties. The large

Adam Palmiter Berkley & Veller Greenwood/Dover

3B Freestyle Cir, Dover, VT 05356
/5
$100,000
- 1 Bed
- 1 Bath
- 700 Sq Ft
39 Brookside Dr Unit 7, Brattleboro, VT 05301

Ready for a redo, this home is priced right for anyone who is handy with freshening, light carpentry (flooring) and other minor skills. Worth the effort to find an affordable option to renting or living with Mom! 48 hour a must for notice. This condo is located in a prime location with quick, easy access to I91 and a stones throw to the Whetstone Brook, Farmers Market and Living Memorial Park.

Christine Lewis Brattleboro Area Realty

39 Brookside Dr Unit 7, Brattleboro, VT 05301
/46
$990,500
- 3 Beds
- 4.5 Baths
- 3,318 Sq Ft
42 Sugar House Rd, West Dover, VT 05356

Tucked into the serene hills of Dover, Vermont, this custom crafted mountain home offers the ideal blend of rustic charm and modern comfort just minutes from Mount Snow and The Hermitage Club. Set on a private lot with winter views of both ski mountains, this 3-bedroom(+bonus bedroom), 4.5-bath home features an open-concept layout with soaring cathedral ceilings, exposed beams, and a stunning

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

42 Sugar House Rd, West Dover, VT 05356
/11
$250,000
- Land
- 18 Acres
- $13,889 per Acre
0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301

Tucked in the gently rolling hills of Vermont, this is a sweet spot to build your new home. Located on a class 3 privately maintained road, there are power poles the length of the road with fiber optics ready for the streamers or work at home folks. Build on the road for a short drive and utility ease, or take the secluded route and tuck away in the forest. The acreage is an educated guess and

Christine Lewis Brattleboro Area Realty

0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301
/5
$795,000
- 3 Beds
- 2 Baths
- 1,267 Sq Ft
635 Vermont Router 100 St, Stratton, VT 05360

Great short term or long term rental for investment or use by a large family. Rent one and enjoy the other. Located 1.6 miles north of Mt. Snow with direct access to VAST from this property. This home was renovated in 2014 including a new roof, windows and doors. Current owners replaced hot tub 2 years ago and a tankless water heater 3 years ago. This property is being sold with Listing #5046807.

Ginny Read Read Realty LTD

635 Vermont Router 100 St, Stratton, VT 05360
/7
$795,000
- 4 Beds
- 3 Baths
- 2,142 Sq Ft
633 Route 100, West Wardsboro, VT 05360

Great short or long term rental for investment or use by a large family. Rent one and enjoy the other. Located 1.6 miles north of Mount Snow and with direct access to VAST from this property. This home was renovated in 2014 including new ro0f, windows & doors. Current owners replaced the hot tub 1 year ago and the tankless water heater 3 years ago. Being sold furnished and ready for family,

Ginny Read Read Realty LTD

633 Route 100, West Wardsboro, VT 05360
/30
$698,000
- 4 Beds
- 3 Baths
- 2,600 Sq Ft
10 Grouse Ln, Dover, VT 05356

Welcome to your perfect Vermont getaway! This spacious 4 bedroom, 3 bathroom townhome is ideally located adjacent to the Mount Snow Golf Course, offering year-round enjoyment. Just a short drive to both Mount Snow and The Hermitage Club, you'll have easy access skiing, golfing, dining, and all that Southern Vermont has to offer.Step inside to find a warm and inviting interior, highlighted by

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

10 Grouse Ln, Dover, VT 05356
/28
$400,000
- 2,496 Sq Ft
794 Missing Link Rd, Town of Rockingham, VT 05101

Make this beautifully constructed duplex your home in the woods. Sited on 59 acres of wooded land, you can make use of the trails on foot or bike. enjoy the peace while being just a short drive from Bellows Falls. The home was built from lumber harvested from the property and lovingly built by the present owners. The majority of the land, 53 +- acres, is held in current use with a wood lot plan

John Tolosky Barrett and Valley Associates Inc.

794 Missing Link Rd, Town of Rockingham, VT 05101
/54
$1,280,000
- 2 Beds
- 2 Baths
- 1,234 Sq Ft
171 Pollard Rd, Grafton, VT 05146

Nestled in the mountains of southern Vt, Grafton is one of New England's most quaint and picturesque villages. Grafton hosts shops, galleries, museums a cheese factory and a historic inn with upscale as well as casual dining.A long private drive leads to the house which overlooks several open acres, a pond, and over 1000 acres of green mountain state forestland offering the most

Eric Scott Barrett & Valley Assoc. Inc

171 Pollard Rd, Grafton, VT 05146
/28
$480,000
- 3 Beds
- 2.5 Baths
- 1,842 Sq Ft
15D Snow Tree Ln Unit Clovers D, Dover, VT 05356

This unique townhome in the Snowtree development is located adjacent to the base area at Mount Snow. Head over via the walking bridge to access the magic carpet and tubing area, or take the Snowtree shuttle. If you don't ski you can still easily access the mountain without worrying about parking. Ideal for the ski season, but also summer festivals, hiking, biking, and more. Unlike the condos with

Adam Palmiter Berkley & Veller Greenwood/Dover

15D Snow Tree Ln Unit Clovers D, Dover, VT 05356

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