Windham County VT Homes for Sale

/6
$239,000
- Land
- 1.57 Acres
- $152,229 per Acre
2 Gold Medal Cir, Stratton, VT 05343

This lot is only one mile from the Stratton Mountain Resort's Sun Bowl base area. The lot has views of Stratton's ski trails. The Powers Subdivision has 11 lots in total and 2.71 acres of common land. Additionally, there is 69 acres of conservation land making this community very private. Build your 4-bedroom dream home right here in one of the best planned communities in southern Vermont.

Andrew King Stratton Real Estate

2 Gold Medal Cir, Stratton, VT 05343
/45
$269,000
- 3 Beds
- 1 Bath
- 1,586 Sq Ft
2277 Vermont 30, Jamaica, VT 05343

Meander down the winding private drive and “LO AND BEHOLD” an enchanting country cottage nestled on a serene 4.8 acres awaits you! This quaint 3-bedroom, 1-bath home is brimming with potential. Inside, you'll find wideboard pine flooring in the dining and living rooms, 2 woodstoves, and an additional den area. In 2024, SEVCA conducted an energy service, enhancing the home with spray foam

Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

2277 Vermont 30, Jamaica, VT 05343
/24
$279,900
- 3 Beds
- 2 Baths
- 1,183 Sq Ft
4322 Augur Hole Rd, Brattleboro, VT 05301

Super location! Easy access to Rt 9 and Rt 30 but tucked into nearly a level acre in a lovely country setting. You can tell the previous occupants loved their gardens and a bit of work would restore the blooms to full glory. The pool is a bonus but is waiting for some care to get up and running...The home has emerged from a fun loving schoolhouse filled with learning and joy to a cozy,

Christine Lewis Brattleboro Area Realty

4322 Augur Hole Rd, Brattleboro, VT 05301
/30
$139,000
- Land
- 20 Acres
- $6,915 per Acre
251 Phillips Hill Rd, West Halifax, VT 05358

Discover 20.10 acres of land in Halifax, Vermont, just a short drive to Greenfield, MA, and from skiing at Mount Snow and The Hermitage Club. This property consists of two separately deeded building lots, offering flexibility for two homes or a single retreat. Enjoy seasonal mountain views, peaceful surroundings, and direct access from a quiet country road. In the warmer months, take advantage

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

251 Phillips Hill Rd, West Halifax, VT 05358
/60
$859,000
- 4 Beds
- 3.5 Baths
- 3,212 Sq Ft
104 Juniper Ridge Rd, Brattleboro, VT 05301

Welcome to Juniper Ridge! Where you will find superior craftsmanship, a private haven, and neighbors only one can dream of. As you enter the foyer of this custom built home, you'll feel its character & elegance with vaulted ceilings, arched doorways, terracotta tile and balconies lined with bookshelves. The home was built with attention to the flow, energy and natural light. The kitchen has

Kristen Ziter Taylor Brattleboro Area Realty

104 Juniper Ridge Rd, Brattleboro, VT 05301
/60
$895,000
- 3 Beds
- 3 Baths
- 2,258 Sq Ft
266 Ursa Ridge Rd, Dummerston, VT 05301

This home is living art, tucked away at the end of the road of lovely homes & hundreds of acres ridgetop, yet only 10 minutes from downtown Brattleboro. Built by a craftsman this home is gracious & energy efficient. Building materials have been harvested from it's 51-1/2 acre woodland. Rooms are thoughtfully designed awash with natural light. Walk up the covered, stone walkway to enter the

Randi Ziter Brattleboro Area Realty

266 Ursa Ridge Rd, Dummerston, VT 05301
/27
$559,000
- 3 Beds
- 2.5 Baths
- 2,000 Sq Ft
16 View Rd, Wilmington, VT 05363

Great Chimney Hill vacation home in Lower B section. Super layout where kitchen, counter conversers, dining room folks and living room relaxers can choose to interact as one happy group, or maintain their own separate activities. The pellet stove fireplace & vaulted ceiling in the living room make for such a relaxing space, while the steps that lead to the large loft above provides yet another

Michael Purcell Berkley & Veller Greenwood/Dover

16 View Rd, Wilmington, VT 05363
/18
$319,900
- 3 Beds
- 1 Bath
- 1,323 Sq Ft
164 Chestnut St, Brattleboro, VT 05301

Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with

Christine Lewis Brattleboro Area Realty

164 Chestnut St, Brattleboro, VT 05301
/2
$79,000
- 3 Beds
- 1 Bath
- 744 Sq Ft
100 Dorr Fitch Rd, Dover, VT 05356

This manufactured home needs a complete overhaul and is being sold as-is, but is priced to sell! Having been taken over by critters, which have since been relocated, it would appear that it has to be gutted, but there is a steel frame, a dug well, and cesspool. Thanks to sewer hook up located at the street, there is great potential, as well as view potential from the rear of the property, direct

Adam Palmiter Berkley & Veller Greenwood/Dover

100 Dorr Fitch Rd, Dover, VT 05356
/35
$795,000
- 4 Beds
- 5 Baths
- 3,129 Sq Ft
20 Ray Hill Rd, Wilmington, VT 05363

Rare opportunity to own a completely remodeled and updated vintage farmhouse, completely turn key. This stunning home sits just up from the country village of Wilmington with easy access to dining and shopping, a short drive to Mount Snow, and near the amazing Lake Whitingham, for true four season enjoyment. The interior features meticulously updated open concept living areas, a chef's kitchen

Adam Palmiter Berkley & Veller Greenwood/Dover

20 Ray Hill Rd, Wilmington, VT 05363
/45
$749,000
- 2 Beds
- 1.5 Baths
- 1,600 Sq Ft
679 Burrington Hill Rd, Whitingham, VT 05361

Welcome to a truly one-of-a kind property-a modern Barndominium thoughtfully reimagined from its original barn like beginnings into a stunning architectural masterpiece. Designed by an award-winning architect and brought to life by a meticulous local builder, this home perfectly balances rustic charm with high-end sophistication. Expansive windows throughout invite in the natural beauty of the

Monica Sumner BHG Masiello Brattleboro

679 Burrington Hill Rd, Whitingham, VT 05361
/42
$415,000
- 3 Beds
- 1.5 Baths
- 2,433 Sq Ft
183 Bear Hill Rd, Dummerston, VT 05301

Discover a hidden gem nestled deep in the woods—a rustic retreat that’s entirely off-grid and 100% solar powered. Perfect for nature lovers, creative spirits, or anyone seeking serenity and self-sufficiency.This one-of-a-kind property features a charming main house with a two-bedroom loft attached, currently used for short-term rentals. The main cabin exudes classic Adirondack charm with

Kate Barry EXP Realty

183 Bear Hill Rd, Dummerston, VT 05301
/6
$100,000
- Land
- 3.20 Acres
- $31,250 per Acre
123 U S 5, Westminster, VT 05158

Beautiful flat, open, grassy lot on Rte 5, just over the Westminster town line from Putney. This lot is completely cleared! Used for hay in the past. The house site is in the front 1/3, as the back 2 Acres is a conservation area, for agricultural use only. There are two, 2.5 acre lots available for purchase as well; separately or together. This parcel is separated from the other 2 lots by two

Victoria Woods Brattleboro Area Realty

123 U S 5, Westminster, VT 05158
/14
$75,000
- Land
- 2.50 Acres
- $30,000 per Acre
123 U S 5, Westminster, VT 05158

Beautiful flat, wooded lot on Rte 5, just over the Westminster town line from Putney. There are two, 2.5 acre lots available for purchase; separately or together. Additionally, there is a 3.2 acre open, grassy lot available. This is separated from the other 2 lots by two house parcels.All 3 lots are being sold with deferral language, as they do not have state permits, however they've all had

Victoria Woods Brattleboro Area Realty

123 U S 5, Westminster, VT 05158
/50
$339,000
- 7 Beds
- 4 Baths
- 3,000 Sq Ft
89 Gates Pond Rd, Whitingham, VT 05342

This rare multi-family home presents a unique investment opportunity, featuring four well-designed units. Nestled in the charming town of Jacksonville you're just 23 minutes from the exhilarating slopes of Mount Snow ski resort. The property offers two one-bedroom units on the first floor, alongside a spacious two-bedroom unit and a generous three-bedroom unit on the second floor. Enjoy the large

Monique White Deerfield Valley Real Estate

89 Gates Pond Rd, Whitingham, VT 05342
/11
$75,000
- Land
- 1.00 Acre
- $75,000 per Acre
116 Newcomb Rd, Westminster, VT 05158

Discover the potential of this 1-acre parcel nestled in the heart of picturesque Westminster, Vermont. Set on a quiet country road and framed by mature trees, this level lot offers a tranquil setting with a brook gently meandering along the northern boundary—an ideal natural feature for those seeking peace and privacy.The property includes an existing house, a few garage bays, and

TG Glazer Winhall Real Estate

116 Newcomb Rd, Westminster, VT 05158
/5
$139,900
- Land
- 1.30 Acres
- $107,615 per Acre
00 Creamery Rd, Guilford, VT 05301

Just in time! Unbelievable! A high rolling meadow of your very own! Build the new home, the one you have been waiting for all your life, on this beautifully cared for sweet spot in the Vermont countryside community of Guilford. The boundaries are easy to find, one being right up to the edge of an old stone wall, the others marked with posts. Pick the high point and have a local view of old

Christine Lewis Brattleboro Area Realty

00 Creamery Rd, Guilford, VT 05301
/49
$1,350,000
- 5 Beds
- 3.5 Baths
- 3,516 Sq Ft
732 Under the Mountain Rd, South Londonderry, VT 05155

Londonderry’s Under the Mountain Road is one of the area’s most beautiful roads, meandering along the edge of Glebe Mountain (home to Magic Mtn) and thousands of acres of conserved land. Here you’ll find “Fairmount”, featuring one of the best panoramic views in southern Vermont overlooking the West River Valley and majestic Green Mountains between Stratton and Bromley. The 1810 farmhouse was

Claudia Harris Mary Mitchell Miller Real Estate

732 Under the Mountain Rd, South Londonderry, VT 05155
/3
$35,000
- Land
- 1.00 Acre
- $35,000 per Acre
I22 Fay Boyden Rd, Wardsboro, VT 05355

Level building lot in the Snow Mountain Farms association. Snowmobile trail access, use of indoor pool and tennis court, and easy proximity to both Mount Snow and Stratton ski resorts.

Adam Palmiter Berkley & Veller Greenwood/Dover

I22 Fay Boyden Rd, Wardsboro, VT 05355
/53
$1,625,000
- 4 Beds
- 4.5 Baths
- 4,241 Sq Ft
207 Boynton Rd, Londonderry, VT 05148

Perched on 12.70 pristine acres, this exceptional residence offers the perfect blend of refined comfort & serene seclusion. Set on a private rise w/ sweeping views, the property captures the quiet majesty of all four seasons. A tranquil pond reflects the ever-changing sky, inviting quiet mornings on the expansive deck, a coffee in hand or peaceful evenings listening to nature under the stars.

Kim Morgan-Wohler Wohler Realty Group

207 Boynton Rd, Londonderry, VT 05148
/12
$150,000
- Land
- 5.00 Acres
- $30,000 per Acre
0 Banning Rd, Putney, VT 05346

Location is key, and locations like this don't come along often. Almost at the top of Putney Mountain is this 5+/- acres of mature hard and soft woods, including red oak, birch, beech, pine and hemlock, just waiting to host your full or part time dwelling. The existing driveway, which is shared with the seller, offers access to the length of the parcel. There's a State Wastewater Permit with a

Bill Hickok Berkley & Veller Greenwood Country

0 Banning Rd, Putney, VT 05346
/37
$759,000
- 3 Beds
- 4 Baths
- 3,352 Sq Ft
183 Vacation Lodge Rd, Londonderry, VT 05148

Welcome to your mountain oasis tucked away in the scenic hills of Londonderry, Vermont. This contemporary 3-bedroom, 4-bathroom home is designed for comfort, entertaining, and enjoying every season. Whether you're looking for a relaxing retreat, a rental income opportunity, or a full-time family compound, this property offers something special for everyone.Step into a space that blends

Brian Hill Remax Summit

183 Vacation Lodge Rd, Londonderry, VT 05148
/42
$899,000
- 4 Beds
- 3 Baths
- 3,551 Sq Ft
1247 Cole Pond Rd, Jamaica, VT 05343

A once-in-a-lifetime opportunity to own a large family home on Vermonts hidden gem! Cole Pond, a spectacular private lake surrounded by mountains and nestled between five ski areas - 5 minutes from Stratton and close to Bromley, Mount Snow, Okemo and Magic. Cole Pond homes rarely come on the market, and this one is one-of-a-kind, with a lake-front lawn, walk-in access to the water (also great

Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

1247 Cole Pond Rd, Jamaica, VT 05343
/53
$989,000
- 5 Beds
- 6 Baths
- 5,600 Sq Ft
10 & 14 Wiswall Hill Rd, Newfane, VT 05345

Welcome to 2 exceptional homes set on 8 acres of meadows w/ stone walls, woodland, and frontage on the Smith Brook. The 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 from

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
$150,000
- Land
- 2.80 Acres
- $53,571 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
$315,000
- 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
$369,000
- 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
/24
$599,000
- 3 Beds
- 3 Baths
- 2,625 Sq Ft
282 Pams Hill Rd, Wardsboro, VT 05355

As Vermonty as you can get! Located conveniently between Mount Snow and Stratton, for easy access to skiing, shopping, lakes, and summer fun, sits this idyllic log style chalet with tremendous personal use or rental potential. The home sits on a private parcel not far from the Snow Mountain Farms amenities including indoor pool and tennis court. There is ample parking thanks to a cul de sac

Adam Palmiter Berkley & Veller Greenwood/Dover

282 Pams Hill Rd, Wardsboro, VT 05355
/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
/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
/59
$529,000
- 3 Beds
- 2.5 Baths
- 1,736 Sq Ft
30 Big Bend Loop, Wilmington, VT 05363

Escape to the Green Mountains in this beautifully designed 3+ bedroom home with a spacious loft, 2 bonus rooms, and three finished levels in the sought-after Chimney Hill community, fully permitted for short-term rentals with strong income history—ideal for investors or second-home buyers looking to offset costs. Step inside the custom mudroom with built-in cubbies, bench, and closets, and enter

Chad Lackey Deerfield Valley Real Estate

30 Big Bend Loop, Wilmington, VT 05363
/37
$875,000
- 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
/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

Kristen Ziter Taylor Brattleboro Area Realty

672 Huckle Hill Rd, Vernon, VT 05354
/41
$265,000
- 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
- 20 Acres
- $12,394 per Acre
189 North St, Dover, VT 05356

Discover the perfect Vermont retreat on this 20.09 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
/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
/38
$520,000
- 3 Beds
- 3 Baths
- 2,040 Sq Ft
829 Pennel Hill Rd, Halifax, VT 05342

Spacious cabin set on 16.4 acres with stream and pond. Open main living area features hardwood floors, vaulted ceilings with skylights, exposed beams, and an efficient wood stove. Updated kitchen includes stainless steel appliances and breakfast bar seating.Main level bedroom with shared en suite bathroom featuring claw foot tub and walk-in shower. Spiral staircase leads to primary suite with

Megan Quinn Southern Vermont Realty Group

829 Pennel Hill Rd, Halifax, VT 05342
/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

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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.