Windham County VT Homes for Sale

/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
/9
$50,000
- 2 Beds
- 1 Bath
- 924 Sq Ft
189 Shady Pines Park, Westminster, VT 05158

1981 Skyline Homette mobile home in Shady Pines Park in Westminster. Very affordable approach to housing. Convenient to Rt. 91, Bellows Falls, Putney, Walpole, Brattleboro. Buyer will need to apply to Shady Park for approval. Property is being sold "as is".

John Hatton Berkley & Veller Greenwood Country

189 Shady Pines Park, Westminster, VT 05158
/58
$675,000
- 3 Beds
- 2.5 Baths
- 2,720 Sq Ft
58 Buckboard Dr, Dover, VT 05356

Significant Price Improvement! This beautifully updated mountain retreat in the desirable Dover Hills is just 5 miles from Mount Snow and 30 minutes to Stratton. Thoughtful renovations have transformed the home with a brand-new kitchen featuring a quartz island, copper sink, high-end appliances, custom lighting, and a bar area with wine fridge and sink—perfect for après-ski entertaining. The

Erica Reynolds Southern Vermont Realty Group

58 Buckboard Dr, Dover, VT 05356
/9
$50,000
- 2 Beds
- 1 Bath
- 924 Sq Ft
189 Shady Pines Park, Westminster, VT 05158

1981 Skyline Homette mobile home in Shady Pines Park in Westminster. Very affordable approach to housing. Convenient to Rt. 91, Bellows Falls, Putney, Walpole, Brattleboro. Buyer will need to apply to Shady Park for approval. Property is being sold "as is".

John Hatton Berkley & Veller Greenwood Country

189 Shady Pines Park, Westminster, VT 05158
/22
$299,000
- 3 Beds
- 2 Baths
- 1,512 Sq Ft
6738 Vermont Route 100, Wardsboro, VT 05355

This charming 1500 square foot manufactured home, located just over 3 miles from Mount Snow Ski Resort and a 15-minute drive to Stratton Mountain Resort, offers a perfect blend of comfort and convenience for mountain enthusiasts. 3 bedrooms and 2 bathrooms, this home provides ample space for family or guests. Inside, the open-plan living area is both cozy and spacious, featuring warm wood

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

6738 Vermont Route 100, Wardsboro, VT 05355
/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
/26
$29,000
- 1 Bed
- 1 Bath
- 673 Sq Ft
215 Qtr.4, 89 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

215 Qtr.4, 89 Grand Summit Way, Dover, VT 05356
/10
$250,000
- Land
- 23 Acres
- $10,823 per Acre
184 Dupre Dr, Guilford, VT 05301

Here's a large 23.10 +/- acre parcel that's mostly wooded but with a little bit of open field and possible short range local views. Conveniently located within a few minutes of town, here's an opportunity to enjoy country living while having access to modern amenities. There's a lot of potential for the right buyer! Please respect the privacy of the other houses on the road past this land.

A.J. Bellville Bellville Realty

184 Dupre Dr, Guilford, VT 05301
/36
$85,000
- Land
- 1.31 Acres
- $64,885 per Acre
100 Chimney Hill Rd Unit M 100, Wilmington, VT 05363

Merged Triple Lot on the Hill! Recent soil tests say this looks good for a 3-bedroom home! If you've been thinking of building your Dream home, this is a great spot. Located about 1/2 way up the Hill, right off the pavement. Walk to the Clubhouse, seasonal views, about 2,100' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season tennis,

Sigrid Pickering Chimney Hill Realty

100 Chimney Hill Rd Unit M 100, Wilmington, VT 05363
/38
$85,000
- Land
- 1.09 Acres
- $77,982 per Acre
95 Chimney Hill Rd Unit M95, Wilmington, VT 05363

Triple Merged Lot on the Hill! Recent soil tests say this looks good for a 3-bedroom home! Right off the pavement about halfway up the Hill on the plateau. If you've been thinking of building your Dream home, this is a great spot. Walk to the Clubhouse, seasonal views, about 2,100' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season

Sigrid Pickering Chimney Hill Realty

95 Chimney Hill Rd Unit M95, Wilmington, VT 05363
/10
$350,000
- Land
- 7 Acres
- $49,435 per Acre
103 Schoolbus Depot Rd, Town of Rockingham, VT 05101

Located between Chester and Bellows Falls, just a mile from exit 6 off I-91, the opportunity for development awaits your ideas. Easy access, level parcel for either commercial ventures, gardens, or home. Land consists of two parcels separated by School Bus Depot Road totaling 7.08 acres. The island parcel gives excellent exposure to Route 103 for terrific signage. 103 is a high traffic corridor

Heidi Bernier Berkley & Veller Greenwood Country

103 Schoolbus Depot Rd, Town of Rockingham, VT 05101
/5
$639,000
- 5 Beds
- 3 Baths
- 5,424 Sq Ft
53 N Main St, Wilmington, VT 05363

Formerly listed in the Wilmington Town Records as a Commercial Property, however, the owners changed that designation to Residential including a one bed./one bath apartment and (2) two bedroom, one bath apartments and a 7 bedroom/7.5 half bath once an Inn. The current owner is in the process of installing egress windows in all bedrooms in the Inn. The current owner has also electrified all smoke

Ginny Read Read Realty LTD

53 N Main St, Wilmington, VT 05363
/60
$189,000
- 1 Bed
- 1 Bath
- 624 Sq Ft
17 Snow Tree Ln Unit Ledges B, Dover, VT 05356

What a GREAT SNOW Year so far! Like "The Old Days".... The snow is plentiful and the skiing is too in 2025! Amazing convenience and proximity to The Mount Snow Ski Resort! Views of the mountain. These owners have upgraded the condo to include a gas heating fireplace insert, unique and useful cabinetry and open pass through set up into the bedroom for light, air circulation, privacy and

Steve Goldfarb Deerfield Valley Real Estate

17 Snow Tree Ln Unit Ledges B, Dover, VT 05356
/30
$50,000
- Land
- 0.93 Acre
- $53,763 per Acre
0 Upper Dam Rd Unit 5019848, Wilmington, VT 05363

Double lot on top of the Hill! Recent soil tests say this looks good for a 3-bedroom home! If you've been thinking of building your getaway home, this is a great spot. Walk to the Clubhouse, seasonal views, about 2,400' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season tennis, basketball, pickleball, ice skating, pond fishing, hiking,

Sigrid Pickering Chimney Hill Realty

0 Upper Dam Rd Unit 5019848, Wilmington, VT 05363
/37
$50,000
- Land
- 0.93 Acre
- $53,763 per Acre
0 Upper Dam Rd Unit 5019824, Wilmington, VT 05363

Double lot on top of the Hill! Recent soil tests say this looks good for a 3-bedroom home! If you've been thinking of building your dream home, this is a great spot. Walk to the Clubhouse, seasonal views, about 2,400' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season tennis, basketball, pickleball, ice skating, pond fishing, hiking,

Sigrid Pickering Chimney Hill Realty

0 Upper Dam Rd Unit 5019824, Wilmington, VT 05363
/30
$25,000
- Land
- 0.53 Acre
- $47,170 per Acre
0 2 Wall Way Unit 5019786, Wilmington, VT 05363

Single Lot on top of the Hill! Walk to the clubhouse from your very own vacation home, designed by you. Survey required and septic design. Lot is unimproved but has had recent favorable soil tests. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season tennis, basketball, pickleball, ice skating, pond fishing, hiking, biking, snowmobiling, and more on our 1,200-acre

Sigrid Pickering Chimney Hill Realty

0 2 Wall Way Unit 5019786, Wilmington, VT 05363
/4
$69,900
- Land
- 1.40 Acres
- $49,929 per Acre
15 Running Sap Ln, Dover, VT 05356

Lovely wooded building site not far from the Mount Snow ski resort, nearby lakes, villages, shopping, and dining. Tremendous view potential from this end of road location, looking to the west over the ski mountains and sunsets.

Adam Palmiter Berkley & Veller Greenwood/Dover

15 Running Sap Ln, Dover, VT 05356
/9
$45,000
- Land
- 1.50 Acres
- $30,000 per Acre
00 Lawrence Davis Dr, Wilmington, VT 05363

Located at the end of a peaceful private road, this serene lot offers both privacy and convenience. The gently sloping terrain leads to a beautiful, flat clearing, ideal for building your future home. Surrounded by mature trees, the property is a nature lover’s dream. Just minutes from Mount Snow and downtown Wilmington, you'll enjoy easy access to shopping, dining, and scenic hiking trails.

Mike Masters Four Seasons Sotheby's Int'l Realty

00 Lawrence Davis Dr, Wilmington, VT 05363
/5
$89,000
- Land
- 0.21 Acre
- $423,810 per Acre
46-48 Lexington Ave, Brattleboro, VT 05301

This open, level, in-town building lot is a blank slate awaiting its next chapter. Tucked away in a small neighborhood on a dead-end street, this location offers easy accessibility to shopping, restaurants, public transportation and the interstate. Utilities are readily available, including existing hookups for town water and sewer. A unique opportunity!

Stephanie Wilde Brattleboro Area Realty

46-48 Lexington Ave, Brattleboro, VT 05301
/8
$2,250,000
0 Tenon Ln, Dover, VT 05356

A unique opportunity to purchase 14 acres in the Mount Snow base area with permits in place for the development of 38 townhouse units, all within walking distance to the Mount Snow ski resort!With the close proximity to the ski area and views of the mountain and surrounding village, this rare opportunity is a developer's dream.Permits and additional information are provided in the

Patricia Fitzpatrick Skihome Realty

0 Tenon Ln, Dover, VT 05356
/48
$1,335,000
- Land
- 4.17 Acres
- $320,144 per Acre
8 Rice Hill Rd, Dover, VT 05341

ONCE IN A LIFETIME PURCHASE What the Boston Globe described as “One of The most spectacular mountain panoramas in all of New England” Is now available for you to build your ultimate mountain home in the finest Dover neighborhood. Finding a rolling cascade of mountain ranges of one, two or three in your viewscape is outstanding. Having five or six to regale your eye as you look out 70 miles to

Lawrence Zupan EXP Realty

8 Rice Hill Rd, Dover, VT 05341
/10
$175,000
- Land
- 5.00 Acres
- $35,000 per Acre
0 Allyn Rd, Putney, VT 05346

Magical! Full of mushrooms, wildlife, beautiful stones, lovely trees and, of course, a stream of your own! Mostly bounded by stone walls, built with amazing skill and tenacity, by generations of hardworking farmers...you have to appreciate their joy in the land. Look carefully as there is a small stone foundation...the remains of?...sheep shed? shelter for the header? a get away from the

Christine Lewis Brattleboro Area Realty

0 Allyn Rd, Putney, VT 05346
/58
$769,000
- 4 Beds
- 3 Baths
- 4,379 Sq Ft
587 Vermont 121, Grafton, VT 05146

Welcome to the Woolley House, an 1818 Brick Federal-style gem nestled in the picturesque town of Grafton. This home perfectly marries historic charm with modern amenities. Original features include four Regency fireplaces, a central cooking fireplace with a crane, wide pine floors, 12-over-12 windows, and a unique hand-crank doorbell. The modern addition boasts a custom granite kitchen, three

Mendi Michael Engel & Völkers Okemo

587 Vermont 121, Grafton, VT 05146
/2
$125,000
- 2 Beds
- 1 Bath
- 1,413 Sq Ft
100 Legion Rd, Newfane, VT 05345

Take a trip back in time when it was easy to build your own home, create a light filled environment, and just sit on the deck with something to sip! Recapture the little bit of country living you are looking for by finishing the project started by someone with a dream! There is a huge kitchen with beautiful island counter top, 2 modest bedrooms, a huge living room with a cathedral ceiling for

Christine Lewis Brattleboro Area Realty

100 Legion Rd, Newfane, VT 05345
/30
$449,000
- 2 Beds
- 2 Baths
- 1,060 Sq Ft
26 Northbrook Village Way Unit 5L, Dover, VT 05356

This 2 bedroom, 2 bath, end unit is a great home base for trailside living at Seasons on Mount Snow. Midway up in the development, this unit offers the convenience of ski-on/ski-off, as well as being close enough to walk to one of the best onsite amenities center in the valley. The amenities center features a recently renovated and expanded clubhouse with an indoor pool, locker rooms, saunas,

John Redd Skihome Realty

26 Northbrook Village Way Unit 5L, Dover, VT 05356
/5
$39,000
- Land
- 1.50 Acres
- $26,000 per Acre
0 Upper Oak Hill Rd, Newfane, VT 05345

1.5 acre level building site in a neighborhood of established homes. Close to Brattleboro and skiing at Stratton. Not far from Rt 30 so easy in and out of the property.

Eric Scott Barrett & Valley Assoc. Inc

0 Upper Oak Hill Rd, Newfane, VT 05345
/5
$680,000
- Studio
- 5,540 Sq Ft
50 Terrace St, Brattleboro, VT 05301

SUPERB OPPORTUNITY to acquire one of Brattleboro’s nicest multi-family, investment properties!! Situated in one of THE BEST neighborhoods in Brattleboro, Vermont, this sweet, money-maker offers 7 units on a quiet street that is SOOO close to downtown Brattleboro. What every investor dreams of!!! Location, quality condition and build, spacious unit size, superb level, off-street parking, and

Dan Normandeau Berkley & Veller Greenwood Country

50 Terrace St, Brattleboro, VT 05301
/48
$999,800
- 4 Beds
- 3.5 Baths
- 2,500 Sq Ft
60 Forest Heights Rd, Stratton, VT 05360

Spectacular Soaring Post and Beam located on the Dover/Stratton town line. This fabulous home boasts soaring vaulted ceilings in the living room with a wall of windows bringing the view into your home complete with a cozy brick fireplace that sets the perfect ambiance. The kitchen is a chef’s delight, featuring granite countertops with eat in dining, a center island, half bath and easy access to

Richard Caplan Deerfield Valley Real Estate

60 Forest Heights Rd, Stratton, VT 05360
/41
$8,950,000
- 6 Beds
- 10 Baths
- 13,393 Sq Ft
370 Fischer Ln, Jamaica, VT 05343

Accessible, but miles from the everyday. Camp Endo’s mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark

Dia Jenks LandVest, Inc/Woodstock

370 Fischer Ln, Jamaica, VT 05343
/47
$1,800,000
- 4 Beds
- 3.5 Baths
- 2,698 Sq Ft
89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360

Trailside! Ski In, Ski Out! The very best Ski Direct Access at Stratton! Most popular of luxury townhouses--offering an enlarged patio with hot tub, open and sunny, four bedroom plus den floorplan, single car garage. Fully furnished! Hardwood flooring, floor to ceiling stone, wood burning fireplace! Enjoy this outstanding trailside location! And as an added benefit, the Stratton Training and

Edwin Kevil Stratton Real Estate

89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360

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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.