Windham County VT Homes for Sale

/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
/24
$26,500
- 1 Bed
- 2 Baths
- 840 Sq Ft
89 236 Qtr. 2 Grand Summit Way, Dover, VT 05356

Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Benefits of Grand Summit ownership include the best ski in/out mountain location available. Use of the Grand Summit amenities all year round including valet parking, owners private lounge, private owners library, full service spa with saunas hot tubs and outdoor heated pool, private owners only ski/golf locker rooms for year

Kelly Agrillo Southern Vermont Realty Group

89 236 Qtr. 2 Grand Summit Way, Dover, VT 05356
/42
$499,000
- 4 Beds
- 2.5 Baths
- 1,986 Sq Ft
168 Howard Rd, Jamaica, VT 05343

This loving home has seen many years of enjoyment from its current owners. Four bedrooms, two and a half baths, large open kitchen dining area with a beautiful granite island to gather around. Separate living room space with beautiful stone fireplace and half bath all on the main floor. The four bedrooms with a lovely large primary suite with private bath, cathedral ceilings will be the perfect

Julie Lowe Lowe's Real Estate, LLC

168 Howard Rd, Jamaica, VT 05343
/27
$3,125,000
- 4 Beds
- 4 Baths
- 4,333 Sq Ft
56 Coldbrook Crossing, Wilmington, VT 05363

Spectacular custom home at the base of the Hermitage Club in the Coldbrook Crossing community, adjacent to the base of Haystack mountain. This is a stunning lot overlooking the trails and sunsets beyond, with easy mountain access, snowmobile trail access, and views unimpeded by any other homes. The luxurious features include a vaulted great room with exposed natural wood beams and stone hearth

Adam Palmiter Berkley & Veller Greenwood/Dover

56 Coldbrook Crossing, Wilmington, VT 05363
/27
$359,000
- 3 Beds
- 2.5 Baths
- 1,266 Sq Ft
7271 Windham Hill Rd, West Townshend, VT 05359

Charming and meticulously maintained, this classic Vermont A-frame with a tasteful addition offers the perfect blend of character and comfort. Nestled on just under 2 acres, the home features 3 cozy bedrooms, warm wood accents, and inviting living spaces filled with natural light. Whether you're enjoying a quiet morning on the deck or taking in the peaceful surroundings, this property is a true

Carrie Mathews Winhall Real Estate

7271 Windham Hill Rd, West Townshend, VT 05359
/47
$299,000
- 3 Beds
- 1 Bath
- 1,222 Sq Ft
1082 W River Rd, Brattleboro, VT 05301

Welcome to 1082 West River Road — a peaceful, well-located gem just minutes from downtown Brattleboro. This charming home offers the perfect blend of convenience, outdoor space, and natural beauty. Set on a spacious lot with a large, open yard, there's room to garden, gather, or simply relax and enjoy the Vermont seasons. The private river access makes it easy to enjoy kayaking, swimming, or

Kate Barry EXP Realty

1082 W River Rd, Brattleboro, VT 05301
/26
$349,900
- 3 Beds
- 1.5 Baths
- 1,370 Sq Ft
749 Vermont Route 100, Wardsboro, VT 05355

This charming, updated 3-bedroom, 2-bath Cape style home sits on 0.17 acres in the heart of Vermont's ski country. Filled with natural light, the warm and inviting interior features a main-level bedroom, while two additional upstairs bedrooms are perfect for guests. After a day on the slopes, unwind by the cozy gas fireplace. Enjoy your morning coffee on the covered porch, or spend evenings

Cassandra Ehrlich BHG Masiello Brattleboro

749 Vermont Route 100, Wardsboro, VT 05355
/60
$729,000
- 3 Beds
- 2 Baths
- 2,731 Sq Ft
49 Tyler St, Brattleboro, VT 05301

Rare opportunity to own this iconic Queen-Anne Victorian in Brattleboro’s coveted Tyler Street neighborhood. A remarkable and extremely rare blend of country and in-town living. Extraordinary and stunning views of the Connecticut River & Mount Wantastiquet. Lovingly cared for by the same owner for the past 29 yrs. This home sits proudly on the expansive 0.85-acre corner lot, in the core of

Dan Normandeau Berkley & Veller Greenwood Country

49 Tyler St, Brattleboro, VT 05301
/10
$35,000
- Land
- 1.10 Acres
- $31,818 per Acre
4 Antler Loop, Dover, VT 05356

Wooded Acre Close to Skiing at Mount SnowBeautiful wooded parcel less than ten minutes from skiing at Mount Snow and all the attractions in downtown Dover.While the property's address is technically 4 Antler Loop, it's much easier to access off the end of Timberview Road, which is one street up the hill. After passing by a gorgeous home at 15 Timberview, the road swaps over from

David White OwnerEntry.com

4 Antler Loop, Dover, VT 05356
/51
$949,000
- 5 Beds
- 8 Baths
- 7,430 Sq Ft
925 Hinesburg Rd, Brattleboro, VT 05301

Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

Christine Lewis Brattleboro Area Realty

925 Hinesburg Rd, Brattleboro, VT 05301
/16
$325,000
- 2 Beds
- 2 Baths
- 1,440 Sq Ft
10 Riverfront Dr, Bellows Falls, VT 05101

This recently renovated home is located on and with gorgeous views of the Connecticut River, frontage suitable for a wharf. Two bedrooms, two full baths and a beautifully crafted stone and brick fireplace. A large, private backyard, inviting family gatherings, just minutes to I91 and Okemo Mountain.

Gale Alger Alger Real Estate Agency

10 Riverfront Dr, Bellows Falls, VT 05101
/38
$465,000
- 3 Beds
- 1.5 Baths
- 1,560 Sq Ft
660 Bonnyvale Rd, Brattleboro, VT 05301

Tucked away on a peaceful 4.3-acre lot surrounded by mature trees, this “wow—worthy” 960 sq ft modern “glass house” (with additional 600+ sq ft of lower level living) on Bonnyvale Road, offers a stylish and serene retreat. Exquisitely designed, it blends indoor ease and simplicity with an outstanding natural setting. The stand-out home features an open-concept layout filled with natural light

Kate Barry EXP Realty

660 Bonnyvale Rd, Brattleboro, VT 05301
/26
$497,500
- 4 Beds
- 3 Baths
- 1,776 Sq Ft
28 Country Club Rd, Dover, VT 05356

Beautifully updated and rustic chalet just south of Mount Snow and near the Mount Snow golf course and Valley Trail. This home sits on a wooded private lot but with amazing convenience just up from a MOOver shuttle drop off location, on a paved road, with easy access to nearby trails. Just about everything has been updated to make this a turn key property, and ready for immediate enjoyment.

Adam Palmiter Berkley & Veller Greenwood/Dover

28 Country Club Rd, Dover, VT 05356
/8
$40,000
- Land
- 5.00 Acres
- $8,000 per Acre
0 Ober Hill Rd, Townshend, VT 05353

Escape to your own private piece of Vermont with this beautiful 5-acre sloping wooded property. Located off the beaten path, yet conveniently close to route 30, you’ll find a peaceful forest of mature Oak, Ash and Pine trees. Remnants of a 1970s treehouse dwelling can be found amidst the trees, marking a fascinating era in local history. Whether you're a camping enthusiast or seeking a serene

Rebecca Hiam Southern Vermont Realty Group

0 Ober Hill Rd, Townshend, VT 05353
/35
$795,000
- 3 Beds
- 2 Baths
- 2,170 Sq Ft
27 Stearns Ave, Wilmington, VT 05363

Nestled in the heart of Vermont’s Green Mountains, check out this stunning Moosehead log home. With private, shared access to Lake Raponda just a short walk away, this inviting single-family home seamlessly blends rustic charm, modern comfort, and a serene natural setting. With 2,170 sq. ft. of living space, this 3-bedroom, 2-bath home welcomes you with warmth and tranquility from the moment you

John Redd Skihome Realty

27 Stearns Ave, Wilmington, VT 05363
/45
$295,000
- 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
/50
$469,000
- 2 Beds
- 1.5 Baths
- 1,346 Sq Ft
2194 Mowrey Rd, Jamaica, VT 05343

Diamond in the rough! Don't miss this opportunity to own a property in Jamaica, Vermont that has so much to offer! This property has been absolutely stunning in the past! Perched on a hill overlooking a private pond, fields that used to be pastures where your animals can roam and you can take in the local ridgeline view of the beautiful Green Mountains of Vermont! This is a true log home with

Julie Lowe Lowe's Real Estate, LLC

2194 Mowrey Rd, 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
/58
$859,000
- 3 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
$995,000
- 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
/60
$260,000
- 3 Beds
- 2 Baths
- 1,250 Sq Ft
111 Binney Brook Rd Unit M581, Wilmington, VT 05363

Nice location on the Hill! Featuring a fairly level lot, seasonal views from the deck, a vaulted ceiling in the living room, along with a wood-burning fireplace and adjacent dining area, which is next to the kitchen. Original wood paneling and detailing are intact, a compact galley kitchen, shower bath and two bedrooms on the main upstairs level. The lower walkout level has a bedroom, full bath

Sigrid Pickering Chimney Hill Realty

111 Binney Brook Rd Unit M581, 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
/41
$395,000
- 4 Beds
- 2 Baths
- 1,758 Sq Ft
3091 Route 121, Windham, VT 05359

Slow down and take time to soak up the charm and character of this sweet house in the beautiful town of Windham! The c. 1860 antique Country Cape is a true testament to the enduring appeal of fine craftsmanship and a life well-lived. The house sits on 12 acres, with a stream and flower-filled meadows beyond, and one of the best front porches in Windham – relax, enjoy the view, and watch the world

Claudia Harris Mary Mitchell Miller Real Estate

3091 Route 121, Windham, VT 05359
/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
/34
$334,500
- 3 Beds
- 1.5 Baths
- 1,848 Sq Ft
49 Hampshire Cir, Brattleboro, VT 05301

Cute home at the end of the cul-de-sac. Large front deck with a slider that leads into a newly refinished kitchen, dining area and living room. A half bath with laundry complete the first floor. Two bedrooms upstairs with a full bath. First floor has a door that leads out back to another large deck. The third bedroom and family room in the walkout basement. Open house Saturday 6/21/25 from

Darlene Conca Keller Williams Realty Metro-Keene

49 Hampshire Cir, Brattleboro, VT 05301
/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
/43
$435,000
- 3 Beds
- 3 Baths
- 2,356 Sq Ft
60 Lily Pond Rd, Vernon, VT 05354

Modern, contemporary 2-story home w/ unobstructed southern exposure in school-choice town of Vernon, Vermont. Built in 2010, this 3BR, 3BA home sits on a 1-acre, level lot, close to town rec. dept., as well as VAST snowmobile trail. Enter via the oversized 2-car garage (32 ft x 28 ft) or greet your guests at the formal front entry off the full-length farmer’s porch. Garage entry hall offers 2

Dan Normandeau Berkley & Veller Greenwood Country

60 Lily Pond Rd, Vernon, VT 05354
/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
/11
$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
$1,725,000
- 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

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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.