17 Houses For Sale in Windsor, VT

Sort by:
New
1008 SqFt House In Juniper Terrace
$235,000Est. Payment
3 Beds | 1 Bath | 1,008 Sqft
39 Channing Drive, Windsor, VT 05089
House For Sale

This Ranch is immaculate, and you will feel excited the second you step foot in the garage. Every bit has been redone, including the roof, the windows, the floors, bathroom, kitchen, landscaping, boiler and oil tank, generator, and the wiring. Enjoy warm summer evenings on the screened in porch off the back and watch the deer, turkeys and mama bear with cubs. The neighborhood is ideal for walks and riding bikes, and you are minutes into town and Paradise Park.

2922 SqFt House In West Windsor
$415,000Est. Payment
4 Beds | 3 Baths | 2,922 Sqft
1697 Sheddsville Road, West Windsor, VT 05089
House For Sale

Bring the whole family to hunt, ski and explore. Seasonal Views of Mt. Ascutney from the wrap around porch. Just minutes from Woodstock and Quechee Gorge. This unique property located in beautiful West Windsor Vermont, is an authentic log home added on in 1990 with an enormous master suite and loft area boasts 1.5 baths, floor to ceiling fireplace, added on to the original 3 bedroom, 1bath ranch with kitchen and great room. 2 Homes are joined together to show as one from the exterior, but have separate entrances and could easily convert to 2 separate living quarters should that be your desire.

Private House With Fireplace
$450,000Est. Payment
3 Beds | 2 Baths | 2,530 Sqft
1747 Hunt Road, Windsor, VT 05089
House For Sale

Cider Hill Farm is one of Windsor's favorite hidden gems. Located just minutes from the West Windsor town line, and Windsor Village, this tranquil, secluded farm property features a three bedroom post and beam cape filled with warmth, comfort, and creative, inspiring elements. The living room has cathedral ceilings anchored by a fireplace, and sliders that step out to a private deck. The spacious, open country kitchen is the perfect place to gather and entertain friends and family. There are two cozy bedrooms on the main level, and a painter's studio that could serve as a great family room, or bedroom. There is one bedroom upstairs, with two oversized loft spaces (an easy conversion to sleeping quarters). The finished lower level could transition to a master suite, office or playroom. There is a lot of multi-functional space within a very efficient footprint. The grounds are lovely, with copious, established perennial gardens, and footpaths lacing through an everchanging palette of specialized woodland plantings. There is a separate studio/office cottage, garden and equipment sheds, apple orchards, an old cider house / barn, and a pond. Its a bird sanctuary by day, with owls to serenade you at night. This is a true working farm, with countless options and directions that one could take - retreat, artist colony, airbnb, events venue, farm to table, on and on. Come see for yourself, and experience the magic of Cider Hill Farm. For additional information, or a private showing, please contact Listing Agent, Daniel Kogut at Williamson Group Sotheby's Intl Real Estate in Woodstock. This property is offered for sale "As Is".

1600 SqFt House In Windsor Village
$199,000Est. Payment
3 Beds | 2 Baths | 1,775 Sqft
56 Union St, Windsor, VT 05089
House For Sale

In town house sits along the Mill Brook, nice backyard with koi pond, large deck and garden shed. The house has an attached one car garage and paved driveway. The main floor boast a lovely oak kitchen with slider onto the side deck, family room with pellet stove and spacious front living room. Three bedrooms and attic storage on the second floor. Lots of upgrades to the systems including a newer furnace, on-demand hot water, circuit breakers and a metal roof.

2044 SqFt House In Windsor Village
$199,000Est. Payment
4 Beds | 2 Baths | 2,044 Sqft
119 Ascutney Street, Windsor, VT 05089
House For Sale

This village home is ready to go. You'll love the hardwood floors and stone fireplace in the family room, and the room is filled with light and brand new windows. Complete with 4 bedrooms, there is room for everyone. The new boiler is a fantastic addition. You are walking distance to the pond, the school, the fairgrounds, and Paradise Park.

925 SqFt House In Windsor Village
$135,000Est. Payment
3 Beds | 1 Bath | 925 Sqft
18 Cherry Street, Windsor, VT 05089
House For Sale

Cozy, recently updated, 3-bed, 1-bath ranch in convenient Windsor location! This property offers a nice front yard and an attached covered parking area to shield you from any weather as you head inside. The open concept living area features laminate floors throughout the main level, a pellet-burning stove, spacious kitchen, and an abundance of natural sunlight. Newer appliances include an electric stove, large fridge and microwave. Down the hall from your kitchen and living room you can find the three bedrooms and shared full bath. The private backyard is a great spot to put out an outdoor dining set for the warmer Vermont months. Easy walking distance to Mill Pond and the fairgrounds, and just a short drive to Mount Ascutney + local trails, you won't want to miss checking out this wonderful home!

6232 SqFt House In Windsor Village
$995,000Est. Payment
9 Beds | 9 Baths | 6,232 Sqft
26 Main Street, Windsor, VT 05089
House For Sale

Welcome to the Snapdragon Inn! This majestic property, built in 1815, can be converted into a grand residence or continue operation as a tranquil inn. There are 9 private bedrooms that include their own ensuite baths with radiant heat. This estate includes a dining area, library, and guest lounge. Each room is filled with sunlight and warmth. This spot offers walking distance to shopping and in town activities and Paradise Park for hiking or a walk around the lake. You will quickly see how centrally located the Snapdragon Inn is to the Upper Valley amenities including the beautiful downtown areas of Hanover, NH & Woodstock, VT, I-91/89, and all of the ample skiing in the East. If you have ever dreamed of owning a quintessential Vermont inn, then look no further!

Upscale Private House
$1,150,000Est. Payment
4 Beds | 3 Baths | 4,200 Sqft
89 Silver Hill Road, West Windsor, VT 05089
House For Sale

NEW CONSTRUCTION IN 2021 AND ALMOST DONE! Pick you interior paint colors in this gracious VT country home on 8.88 acres, boasts 4,200+ sqft, 3-4 bedrooms, 2.5 baths, hand-plastered walls, high-speed Fiber Optic internet, a 2-car garage, and a stunning 18 foot beamed cathedral ceiling with a soaring New England stone fireplace in the Family Room. Exceptional craftsmanship and superior location in West Windsors horse country giving you easy access to Woodstock & Ascutney Outdoor Center recreational trails. There is a fully equipped country kitchen with custom walnut cabinetry, Kitchen Aid appliances, a 48-inch WOLF dual-fuel double oven range, and elegant Equinox VT Soapstone countertops provide generous counter space for your next dinner party. This home has a gracious open flowing floor plan with a large first-floor private master bedroom suite and spa-like bathroom (all baths have marble countertops). Quality Andersen windows, a 48-foot mahogany porch, and a private office in wainscoted Alderwood. Oversized Patio doors extend out to the rear lawn & lovely stonewalled grounds. There is a full basement, abundant attic storage, and the drilled well delivers over 50gpm with enough water for a pond. Underground utilities, upscale mechanicals, and even radiant & baseboard FHW heat. See MLS #4851737 for an additional 17.3 acres of woods and meadow to turn this into a horse property for a total of 26 acres. Be in by late June to early July 2021!

$195,000
4884 SqFt House In West Windsor
$1,800,000Est. Payment
5 Beds | 5 Baths | 4,884 Sqft
974 Cemetery Hill Road, West Windsor, VT 05089
House For Sale

White Fox Farms c. 1790 yellow clapboard farmhouse and attached red barn is set just outside the village of Brownsville on a quiet country road where it seems like more horses go by than cars. The 39 acres scale of the farm is manageable with the key Vermont features: a pond, pastures and big views of Mt. Ascutney. The five-bedroom house underwent a major renovation in 2012. The kitchen with its hand hewn beams was enlarged to include a sitting area with views over the field, and outfitted with top-flight appliances for a cook that likes to prepare meals while surrounded by family and friends. Pssstthere is a secret room, believed to be part of the Underground Railway. There are fireplaces in the living room, the two master bedrooms, the birthing room (now used as an office), dining room and paneled family room. The third level is a great place for innovative thoughts (the owner launched a business here) with a two-room study with built in book shelves and a bath. Throughout the house there is a sense of fine craftsmanship that has stood the test of time in form and function. White Fox Farm is integral to the Green Mountain Horse Association community as the 83-mile marker for the hundred-mile ride.

House In Windsor Village
$3,151Est. Payment
-- Beds | -- Baths | -- Sqft
Windsor, VT 05089
House For Sale

Bank owned foreclosure Single Family Home features great opportunity. Bank-Owned Foreclosures can offer opportunities to purchase properties at attractive prices.

House In Windsor Village
$84,600Est. Payment
3 Beds | -- Baths | 1,232 Sqft
Windsor, VT 05089
House For Sale

Located near the end of a dead end street and also near Mill Pond, this home is convenient to where you need to go! There's a nice covered front porch as well as a detached 1 car garage. The interior features 3 bedrooms, formal dining room, a nicely sized living room and character and charm throughout. This property is definitely worth checking out!

House In Windsor
$1,152Est. Payment
-- Beds | -- Baths | -- Sqft
Windsor, VT 05089
House For Sale

Bank owned foreclosure Single Family Home features great opportunity. Bank-Owned Foreclosures can offer opportunities to purchase properties at attractive prices.

House In Windsor Village
$2,100Est. Payment
-- Beds | -- Baths | -- Sqft
Windsor, VT 05089
House For Sale

Bank owned foreclosure Single Family Home features great opportunity. Bank-Owned Foreclosures can offer opportunities to purchase properties at attractive prices.

House In Windsor Village
$28,010Est. Payment
-- Beds | -- Baths | -- Sqft
Windsor, VT 05089
House For Sale

Bank owned foreclosure Single Family Home features great opportunity. Bank-Owned Foreclosures can offer opportunities to purchase properties at attractive prices.

House In Windsor
$165,680Est. Payment
-- Beds | -- Baths | -- Sqft
Windsor, VT 05089
House For Sale

Bank owned foreclosure Single Family Home features great opportunity. Bank-Owned Foreclosures can offer opportunities to purchase properties at attractive prices.

House In West Windsor
$482,000Est. Payment
-- Beds | -- Baths | -- Sqft
West Windsor, VT 05089
House For Sale

Bank owned foreclosure Single Family Home features great opportunity. Bank-Owned Foreclosures can offer opportunities to purchase properties at attractive prices.

House In Windsor
$18,717Est. Payment
-- Beds | -- Baths | -- Sqft
Windsor, VT 05089
House For Sale

Bank owned foreclosure Single Family Home features great opportunity. Bank-Owned Foreclosures can offer opportunities to purchase properties at attractive prices.