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Windham County Vermont Real Estate For Sale

Welcome to WindhamCountyVermontRealEstate.com, a Vermont Country Properties Sotheby's International Realty website, offering fine homes, condominiums, townhouses, land parcels, and commercial real estate properties throughout Windham County, Vermont, including the towns of Londonderry, Windham, Grafton, Jamaica, Stratton, Brattleboro, Rockingham, and Guilford.
 
The mission of Vermont Country Properties Sotheby's International Realty is simple: to provide buyers and sellers with the most professional real estate services available, delivered by a staff of over 50 brokers and sales associates who are experienced, reputable, and knowledgeable. We commit to the highest level of professional conduct and representation. Our marketing platform is constantly evolving and is the most comprehensive in all of Vermont, utilizing extensive web based promotion and broad based print advertising.
 
Browse our exclusive listings below or use the search navigation at the left to refine your search and access all property listings in the Windham County, Vermont area. You can also subscribe to our eListings newsletter to receive new properties that match your search in your email inbox as they are listed.
 
 

 

Exclusive Listings for WindhamCountyVermontRealEstate.com

     Hidden Meadows   ·  Stratton / South Londonderry, VT  
View Property Listing for Hidden Meadows  - Residential - Stratton / South Londonderry, Vermont (VT) An exceptional country estate in the heart of the Green Mountains. Georgian style main residence and guest house with world class amenities. The pool pavilion is worthy of the finest resort; impressive club house; sunken clay tennis courts. Sweeping landscape...
Type: Residential
Price: $4,900,000
Acres: 90.9
Square Feet: 8004
Bedrooms: 5
Baths: 7 Full, 1 Half
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     JOHNNY SEESAW'S INN & RESTAURANT   ·  Peru, VT  
View Property Listing for JOHNNY SEESAW'S INN & RESTAURANT - Commercial - Peru, Vermont (VT) This property is offered by the Phoenix Commercial Division. The oldest, continuously operating ski lodge in the country, Johnny Seesaw’s is located next to Bromley Mt. Ski Area and Stratton Mt. This quaint, New England lodge was built in 1920 by Russian...
Type: Commercial
Price: $1,495,000
Acres: 6.7
Square Feet: 18235
Bedrooms: 22
Baths: 26
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     Solstice Trailside   ·  Stratton / South Londonderry, VT  
View Property Listing for Solstice Trailside  - Condo/Townhouse - Stratton / South Londonderry, Vermont (VT) Ski-in Ski-out from this beautifully appointed trailside townhouse in Stratton's prestigious Solstice community. Stone fireplace, wood floors, open floorplan, gourmet kitchen and cathedral ceilings create a premier mountain getaway. The floorplan features...
Type: Condo/Townhouse
Price: $1,495,000
Acres: 0.5
Square Feet: 2450
Bedrooms: 4
Baths: 3 Full, 1 Half
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     North Brookwood Road   ·  Stratton / South Londonderry, VT  
View Property Listing for North Brookwood Road   - Residential - Stratton / South Londonderry, Vermont (VT) Classic Chalet at the top of prestigious North Brookwood with panoramic views and 40 yards walk to Wanderer Ski Tail. High on the ridge overlooking mountains, ski slopes and valleys, this 5 bedroom, 4&1/2 bath chalet was expanded in 1990. The master bedroom...
Type: Residential
Price: $1,395,000
Acres: 1.3
Square Feet: 3078
Bedrooms: 5
Baths: 4 Full, 1 Half
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     Mountain View Road   ·  Bondville/Winhall, VT  
View Property Listing for Mountain View Road - Residential - Bondville/Winhall, Vermont (VT) This spectacular luxury residence is the epitome of a mountain getaway. With 6500 sq.ft. of living space, designed for the ultimate in pampering every age, this home has it all. The double great rooms feature immense stone fireplaces. Cathedral ceilings and...
Type: Residential
Price: $1,389,000
Acres: 1.5
Square Feet: 6500
Bedrooms: 6
Baths: 7
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     Pearl Buck Drive   ·  Bondville/Winhall, VT  
View Property Listing for Pearl Buck Drive - Residential - Bondville/Winhall, Vermont (VT) Live and entertain in premier resort style near the top of prestigious Pearl Buck Drive. Spectacular views of Stratton Mountain, Bromley and beyond. Sit in your hot tub and enjoy the stars and snowcats grooming for tomorrow's ski day. Seven bedrooms, including...
Type: Residential
Price: $1,375,000
Acres: 3.5
Square Feet: 3100
Bedrooms: 7
Baths: 5
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     Winhall Hollow Road Farm   ·  Bondville/Winhall, VT  
View Property Listing for Winhall Hollow Road Farm - Residential - Bondville/Winhall, Vermont (VT) This magnificent Winhall property offers a rare opportunity to own one of Southern Vermont's pristine horse farms. Situated on 38.7 picturesque acres with five barns, the equestrian facilities include 25 matted box stalls, 150 x 70 indoor riding arena with...
Type: Residential
Price: $1,375,000
Acres: 38.7
Square Feet: 1517
Bedrooms: 1
Baths: 1
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     Pearl Buck Drive   ·  Bondville/Winhall, VT  
View Property Listing for Pearl Buck Drive - Residential - Bondville/Winhall, Vermont (VT) One of a kind property and custom home perched atop Pearl Buck with views to Mount Snow and direct year round views of Stratton. Unique private parcel of 14.6 mountain acres, just minutes to the resort. Many special features, gourmet kitchen, Viking, Meile...
Type: Residential
Price: $1,350,000
Acres: 14.6
Square Feet: 4330
Bedrooms: 5
Baths: 3 Full, 1 Half
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     Sugarhouse Hill Road   ·  Brattleboro, VT  
View Property Listing for Sugarhouse Hill Road - Residential - Brattleboro, Vermont (VT) Sugar House Hill exemplifies originality and international decorative arts within a most captivating Southern Vermont setting. Offering a five bedroom main residence, two bedroom guest house and additional three car barn-garage upon twenty acres, this...
Type: Residential
Price: $1,295,000
Acres: 20.5
Square Feet: 3200
Bedrooms: 5
Baths: 4
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     Priest Lane   ·  Peru, VT  
View Property Listing for Priest Lane  - Residential - Peru, Vermont (VT) In the heart of the Green Mountain National Forest, this exceptional country residence is peacefully situated against the backdrop of Styles Peak overlooking meadows, lovely stone walls, mature gardens and a trout stocked pond. Approached by a quiet tree...
Type: Residential
Price: $1,295,000
Acres: 17.4
Square Feet: 3400
Bedrooms: 4
Baths: 2 Full, 1 Half
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     Pearl Buck Drive   ·  Bondville/Winhall, VT  
View Property Listing for Pearl Buck Drive - Residential - Bondville/Winhall, Vermont (VT) Premier newly constructed residence, perched atop Pearl Buck Drive on 3.70 acres with panoramic views of the northern mountains. Exceptional crafstmanship. Located just minutes to the Stratton Resort, this exclusive property offers an expansive floorplan and...
Type: Residential
Price: $1,250,000
Acres: 3.7
Square Feet: 4978
Bedrooms: 4
Baths: 4 Full, 1 Half
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     Sunset Ridge Road (Under Contract)   ·  Bondville/Winhall, VT  
View Property Listing for Sunset Ridge Road (Under Contract) - Residential - Bondville/Winhall, Vermont (VT) This impeccable resort residence is a home for all seasons with head-on views from every room. Defined by its abundance of warm natural wood details, this finely crafted Timber Peg home offers great space and mountain atmosphere. The living room boasts a massive...
Type: Residential
Price: $1,100,000
Acres: 1.2
Square Feet: 4500
Bedrooms: 5
Baths: 3 Full, 1 Half
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     Windtree Road   ·  Stratton / South Londonderry, VT  
View Property Listing for Windtree Road  - Residential - Stratton / South Londonderry, Vermont (VT) This expansive Stratton Mountain Resort residence is in a premier location on the North Brookwood winter shuttle. Dramatically situated upon a knoll with beautiful winter views and wooded summer privacy, this custom home offers exceptionally large spaces,...
Type: Residential
Price: $1,099,000
Acres: 1.5
Square Feet: 3950
Bedrooms: 6
Baths: 4 Full, 1 Half
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     Treetop @ Stratton   ·  Stratton / South Londonderry, VT  
View Property Listing for Treetop @ Stratton - Condo/Townhouse - Stratton / South Londonderry, Vermont (VT) This Stratton Mountain Treetop Unit is literally a HOME RUN! You’ll be the envy of all with this Winterberry Heights location that is the only Treetop cluster that has direct access to The Home Run Ski Trail, a trail with snowmaking that leads to the Tamarack...
Type: Condo/Townhouse
Price: $1,089,000
Acres: 1.0
Square Feet: 2400
Bedrooms: 4
Baths: 4
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     Stone Lodge Road   ·  Bondville/Winhall, VT  
View Property Listing for Stone Lodge Road - Residential - Bondville/Winhall, Vermont (VT) This spacious, newly-built Adirondack-style lodge home features 5 gracious bedrooms, 3.5 baths and stunning views throughout. Exceptional construction is evidenced in the massive two-story great room, featuring a massive fieldstone fireplace and oak flooring....
Type: Residential
Price: $1,085,000
Acres: 1.5
Square Feet: 4500
Bedrooms: 5
Baths: 3 Full, 1 Half
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     Upper French Hollow Road   ·  Bondville/Winhall, VT  
View Property Listing for Upper French Hollow Road  - Residential - Bondville/Winhall, Vermont (VT) A warm, friendly log home on 12 acres bordered by National Forest on 2 sides, with easterly views. Very spacious home with lots of room for entertaining young and adult guests. Gourmet kitchen with Viking stove, sub-zero refrigerator, wine refrigerator, cherry...
Type: Residential
Price: $995,000
Acres: 12.1
Square Feet: 4800
Bedrooms: 4
Baths: 4 Full, 1 Half
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     Route 11   ·  Londonderry, VT  
View Property Listing for Route 11 - Residential - Londonderry, Vermont (VT) Come home to Vermont to this charming farm house. Set back off the road on 8.4 acres with circular drive and separate 2 bedroom cottage. Step outside your backdoor and hike, snowshoe or x-c ski for miles on National Forest trails! A cozy pub room with mahogany...
Type: Residential
Price: $975,000
Acres: 8.4
Square Feet: 4230
Bedrooms: 5
Baths: 6 Full, 2 Half
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     Old Ridge Road (Under Contract)   ·  Bondville/Winhall, VT  
View Property Listing for Old Ridge Road (Under Contract) - Residential - Bondville/Winhall, Vermont (VT) Featuring magnificent views of Stratton, this 5 bedroom High Meadow home has recently undergone a partial renovation. Updates include exterior stonework, exterior paint, new retaining wall, re-point chimney, new garage doors and deck work. The vaulted ceiling...
Type: Residential
Price: $950,000
Acres: 1.0
Square Feet: 3500
Bedrooms: 5
Baths: 4
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     Middle Ridge Road   ·  Stratton / South Londonderry, VT  
View Property Listing for Middle Ridge Road - Residential - Stratton / South Londonderry, Vermont (VT) This exceptional Post and Beam mountain residence, designed by Architect Jeff Barnes, is nestled in a desirable location near Stratton's Base Area, while offering a peaceful setting to escape the crowds. Double brick chimneys rise through the center of...
Type: Residential
Price: $949,000
Acres: 1.0
Square Feet: 3000
Bedrooms: 4
Baths: 3 Full, 1 Half
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     NUTMEG COUNTRY INN & BAKERY   ·  Wilmington, VT  
View Property Listing for NUTMEG COUNTRY INN & BAKERY - Commercial - Wilmington, Vermont (VT) This property is offered by the Phoenix Commercial Division. Original 1770's early American farmhouse with upgrades and additions converted to a quaint and luxurious Bed and Breakfast. Many original architectural details. 14 beautifully appointed guest rooms...
Type: Commercial
Price: $919,000
Acres: 2.1
Square Feet: 8000
Bedrooms: 14
Baths: 16
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     Wonder Lane   ·  Bondville/Winhall, VT  
View Property Listing for Wonder Lane - Residential - Bondville/Winhall, Vermont (VT) This beautifully appointed and decorated log home, situated in prestigious Wheeler Woods, enjoys winter views of Stratton Mountain. The entry level slate floor mudroom with 1/2 bath leads into the Great Room featuring a fieldstone fireplace. The open area...
Type: Residential
Price: $875,000
Acres: 1.7
Square Feet: 3400
Bedrooms: 5
Baths: 4 Full, 1 Half
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     Garden Loop Road   ·  Bondville/Winhall, VT  
View Property Listing for Garden Loop Road  - Residential - Bondville/Winhall, Vermont (VT) Panoramic mountain views & premier location in Stratton Gardens make this custom designed country home a spacious Vermont retreat for family and friends. The Main level foyer entrance opens onto the Great Room with fieldstone fireplace and deck to views. A...
Type: Residential
Price: $875,000
Acres: 1.1
Square Feet: 4800
Bedrooms: 6
Baths: 4
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     Benson Fuller   ·  Bondville/Winhall, VT  
View Property Listing for Benson Fuller - Residential - Bondville/Winhall, Vermont (VT) High ceilings, stone fireplace, wood floors and warm accents create a mountain ambiance throughout in this spacious resort residence with several bedroom suites. Designed for winter weekend warriors, the property features a great room that opens to a deck...
Type: Residential
Price: $779,000
Acres: 1.7
Square Feet: 4200
Bedrooms: 4
Baths: 5 Full, 1 Half
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     Thompsonburg Road   ·  Londonderry, VT  
View Property Listing for Thompsonburg Road - Residential - Londonderry, Vermont (VT) Fantastic property sited on 14.56 acres with big Stratton views. The inviting contemporary home features large family room, oversized master bedroom suite, two fireplaces, wrap-around deck and 2-car garage. Surrounding open meadowland is enhanced with a pristine...
Type: Residential
Price: $699,000
Acres: 14.6
Square Feet: 3700
Bedrooms: 4
Baths: 3 Full, 1 Half
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     North Branch   ·  Stratton / South Londonderry, VT  
View Property Listing for North Branch - Residential - Stratton / South Londonderry, Vermont (VT) Classic Austrian Chalet with handcrafted woodwork, renovated and redecorated to recreate European alpine elegance. Entry level has spacious tiled mudroom & large closet, family room, 2 bedrooms & shared bath, laundry/utilities room. Upper main level vaulted...
Type: Residential
Price: $695,000
Acres: 0.8
Square Feet: 1800
Bedrooms: 4
Baths: 2