21 Houses For Sale in Windsor, VT

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$53,000Est. Payment
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191 Channing Dr, Windsor, VT 05089

House For Sale

This is the ideal spot for your dream home. Nice neighborhood location, close to Paradise Park, recreation and downtown, and just minutes to I-91

$96,000Est. Payment
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Lot #42 Paradise Drive, Windsor, VT 05089

House For Sale

This home is located at Lot #42 Paradise Drive Windsor, VT 05089 US and has been listed on Homes.com since 2 July 2020 and is currently priced at $96,000. Lot #42 Paradise Drive is within the school district(s) Mount Ascutney Unified School District with nearby schools including Windsor School. Similar properties nearby are <a href="/property/11-maple-st-windsor-vt-05089/id-700018366941/">11 Maple St</a>, <a href="/property/windsor-vt-05089/id-1000014837250/">72 Bunker Hill Ct</a>, 81 Paradise Dr, and <a href="/property/12-wayside-ln-cornish-nh-03745/id-500023914007/">12 Wayside Ln</a>.

$2,595,000Est. Payment
9 Beds | 9 Baths | 6,921 Sqft

122 Best Road, Hartland, VT 05089

House For Sale

BEST ROAD- Historically significant farmstead in a spectacular setting renovated into a modern masterpiece. The options are endless- the property can be run as a working farm, sophisticated rustic resort, family compound, event & wedding space, production facility or all of the above. There are 59 acres- a lovely mix of open pasture, orchards, fields & woodlands- with commanding views to the east and northeast. The attention to detail, quality of workmanship, and style are premium from the house to the cabins to the barns. The 5 cabins enjoy a successful rental business- although they are more contemporary small homes that are beautifully constructed. The barns and outbuildings can house any variety of animals. Currently there are sheep, goats, chickens, and seasonal horses on the farm. A wonderful 1 mile walking trail meanders through the woods/meadow, and established blueberries and fruit trees can be found throughout the property. Bring your ideas and dreams to this turnkey estate. The farm is perfectly located in a private setting with easy access to Woodstock, Vermont & Hanover, New Hampshire (home of Dartmouth College). Easy interstate access as well for guests or commerce. For more information, please contact David Donegan of Snyder Donegan Real Estate Group.

$675,000Est. Payment
4 Beds | 3 Baths | 3,602 Sqft

414 Brownsville Hartland Road, West Windsor, VT 05089

House For Sale

This beautifully built log home has a comfortable floor plan. An attached two-car garage leads into a generous mudroom for all your Vermont gear and equipment. The lovely great room offers natural light and an incredible floor-to-ceiling stone fireplace. The gourmet kitchen has ample room for gathering with the ambience of a wood fire. Pull up a stool at the soapstone counter or nestle in the booths for your Sunday coffee. Youll also enjoy the large walk-in pantry. The master bedroom has private ensuite, walk-in closet and screened porch. Three additional bedrooms, one with ensuite, a full bathroom plus laundry complete the first floor. The loft, overlooking the great room, makes a perfect office space. The large deck and screened porch provide a view of the picturesque setting year round. For more information contact Holly Hall of Snyder Donegan Real Estate Group

$199,000Est. Payment
4 Beds | 2 Baths | 2,248 Sqft

9 Dorrance St, Windsor, VT 05089

House For Sale

Lovely, well-maintained 4 bedroom, 1.5 bath, home situated on a beautifully landscaped half acre lot. Multiple special features include an eat-in kitchen, gleaming hardwood floors, propane stove in the den, fireplace in the living room and a spacious play room in the basement. You'll love the detached garage that includes a work-shop room in the back. This classic two story home is solidly built, well maintained and in move-in condition, not to mention part of a great neighborhood that is walking distance to Kennedy Pond. BONUS: Seller has a transferable share of a sun common solar array at $76 per month that off sets 100% of electric usage.

$219,900Est. Payment
3 Beds | 2 Baths | 1,376 Sqft

10 Meadow Ln, Windsor, VT 05089

House For Sale

Lovely updated one level living home in wonderful neighborhood of similar homes. Freshly painted rooms, new kitchen counters and flooring. Spacious living room with wood fireplace, hardwood floors throughout. Lovely back yard with patio area and a fenced in dog kennel. Full basement offers tons of storage space or future family room space. Large attached two car garage, paved driveway walk to main street and an easy commute to the Upper Valley.

$600,000Est. Payment
2 Beds | 2 Baths | 2,108 Sqft

515 Mountain Road, West Windsor, VT 05089

House For Sale

A rare find! 82 unencumbered acres with a pond, stream, ancient stone walls, and spectacular long range Northern to South Easterly views. The inventory of hardwoods is pristine. There is an existing farm road that brings you to multiple plateaus ready for you to create your dream. Height of land is 1500'. There is an existing, well-kept c 1980 classic A Frame with 2 BR's, 2 BA that will make a charming guest house, or a revenue producing rental property. Located on a quiet road in the heart of West Windsor's magnificent trail system. 10 minutes to I-91, 20 minutes to Woodstock Village. Easy access to skiing and recreation.

$209,000Est. Payment
3 Beds | 2 Baths | 2,100 Sqft

25 Sherwin Ave, Windsor, VT 05089

House For Sale

Located on the corner lot of a dead end street sits this charming home.Tons of potential with spacious rooms and an apartment above the heated two car garage. Newer windows, standing seam roof, and Thermopride furnace. Natural wood throughout and the three season porch add to the home's charm. With both privacy and ideal proximity to village and recreation amenities, this home is sure to please. Bring your own ideas, and make this home your own.

$189,000Est. Payment
3 Beds | 2 Baths | 1,721 Sqft

18 Pine St, Windsor, VT 05089

House For Sale

Located high on a rim of Lake Runnemede, this 1800's home sits in a quiet neighborhood in the heart of Historic Windsor. You are just minutes away from walking right into the protected land of Paradise Park, where you can safely adventure miles of trails year-round. Among many reasons to love it here is that it is one of the most active and desirable places to bird watch so you are always in for a treat when you roam Paradise. This home has plenty of originality to offer while also having some spectacular upgrades. Come see and feel the charm of this attractive and inviting home. Grand wrap around porch, high ceilings, built-ins, fireplaces, and living space in the attic. So much to fall in love with.

$40,000Est. Payment
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132 Strawberry Hl, Windsor, VT 05089

House For Sale

On the corner of a private little neighbor, this lot is in a great spot. Set off County Road, this lot is ready for your visions to come to life. Minutes from I91 yet set just outside of town. Great hiking/walking trails are within walking distance. This could be the beginning of a very adventurous and exciting time for the new owners!

$160,000Est. Payment
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101 Main St, Windsor, VT 05089

House For Sale

Diverse commercial space ready to have new owners move in and add to the long list of successful businesses that have graced these buildings. From Blacksmithing to a Point Shop and on to Plumbing, Guns, Woodworking, and so much more. If you've been thinking about having a great store front, and plenty of storage, now is the time to JUMP. Come join Windsor's growing economy, all while being 4 miles to I-91. Owner will consider seller financing.

$905,000Est. Payment
8 Beds | 5 Baths | 5,265 Sqft

1672 Hunt Road, Windsor, VT 05089

House For Sale

Kimball Brook Farm, C. 1789,has a storied history. It was once the residence of author and music critic Marcia Davenport, and is featured in her 1967 autobiography, Too Strong for Fantasy. Residents of Windsor report that Katherine Hepburn, a long-time friend of Ms. Davenports was a visitor to the farm. This spectacular home embodies rambling country elegance and provides generous amounts of room for entertaining, family gatherings and/or events. Kimball Brook is comprised of 8 bedrooms and 5 baths a total of 5,300 sq feet. There are both large formal areas and cozy spaces, which along with its 5 working fireplaces, highlight the farms classic Vermont country character. The systems and structure, including heat, water, roofing, siding, foundation, and security have all been intelligently updated with state-of-the-art systems and materials. The large antique barn is a remarkable entity, providing space for projects, animals, vehicles, or celebrations. The property is nestled in a quiet valley amidst the rolling hills of historic Windsor on 32 ac of mixed open and wooded land, overlooking a pond with views into New Hampshire. It is a very short walk (or snowshoe, or bike ride) to an 900+ acre State Wildlife Management Area that provides the many year-round, outdoor activities enjoyed by all Vermonters. Despite its privacy and tranquility, the farm remains easily accessible to local attractions, including Hanover, NH and Woodstock, VT, both within 20 minutes.

$269,000Est. Payment
3 Beds | 3 Baths | 2,400 Sqft

418 Moonrise Hill, Windsor, VT 05089

House For Sale

This single family home is a rare find with a commanding view of Mt. Ascutney, but with only a short, flat driveway to plow. The 5.8 acres consists of both fields and woods. 3 large bedrooms and 3 full baths home with an enclosed porch. There is lots of storage and a full basement. A new roof was put on about 10 years ago. New boiler last winter and an owned solar system. There is a Vermont castings wood stove inside and an outdoor boiler ( that is not currently being used). This is a potential horse property with fields and gravel roads. While the property is located at the end of a road, it is less than 2 miles from Windsor Village, school and the hospital. Easy commute to upper valley. Why pay their prices? Priced below assessment.

$396,000Est. Payment
3 Beds | 3 Baths | 2,456 Sqft

2151 Hunt Road, Windsor, VT 05089

House For Sale

It doesn't get much better than this view! Privately situated on 4.5 level acres with multiple outbuildings and a beautiful pond. This well cared for home has had the same owners for 35 years who have taken meticulous care of the property. Stand out features include a large kitchen, open concept floor plan, spacious master suite, wrap around deck, attached 2 car garage and a full walkout basement. If this wasn't enough you'll also find a 1 bedroom apartment space above the attached garage that could be converted into more living space if desired. This truly is Vermont living at its best.

$1,995,000Est. 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.

$95,000Est. Payment
2 Beds | 2 Baths | 1,210 Sqft

11 Maple Street, Windsor, VT 05089

House For Sale


$114,900Est. Payment
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Windsor, VT 05089

House For Sale

This property is Real Estate Owned, or REO. The property was foreclosed and repossessed by a lender when the owner failed to make payments. A bank is now the owner. Since banks are not in business to own homes, they are usually interested in selling foreclosed homes quickly at attractive low prices. A list price is published but reasonable offers can be submitted for consideration. Offers can be submitted through the official Listing Agent but in some cases, no agent is listed and offers can be submitted the bank owner directly.

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