36 Windsor, VT Real Estate Listings

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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.

Multi-Family Home In Windsor Village
$359,000Est. Payment
-- Beds | -- Baths | 4,057 Sqft
11 Buena Vista Ct, Windsor, VT 05089
Multi Family For Sale

Stately home with three rental apartments in a great neighborhood offers rental income for the owner occupant living in spacious owner's quarters or a straight investment property with income from four rental units. Convenient to schools and shopping on Windsor's vibrant Main Street, this property is well maintained and filled with the charm of by-gone years. 48 hours notice for showings, please.

2-Story Multi-Family Home In Windsor Village
$475,000Est. Payment
-- Beds | -- Baths | 3,592 Sqft
29 Ascutney Street, Windsor, VT 05089
Multi Family For Sale

Located in the heart of Windsor-Just steps away from schools, shopping, dining, recreation and town amenities, this stately brick home was completely restored in 2013. Currently operating as a 3-unit with excellent rental history-renovation was done carefully to preserve original features, central stairway and room layout for future conversion back to a grand main home with 3-bedroom townhouse apartment in back. All units have warm wood floors, high ceilings, natural light, plentiful storage, laundry and updated kitchens and baths. Completely updated systems including all electric service, plumbing, heating, hot water and extensive closed cell foam insulation in basement and ceilings. A rare opportunity to own a lovely, updated home in a great community whether you are looking for investment property or a primary home with income from one or two units to help with a mortgage. In-town living close to abundant outdoor recreation-Mill Pond, Lake Runnemeade, CT River, Ascutney Outdoors, Saint Gaudens National Park and so much more. Convenient to I-91 for access to Upper Valley and beyond. Just 20 minutes from Dartmouth College and Hanover, NH and under 30 minutes from Dartmouth Hitchcock Medical Center and Lebanon, NH.!!!

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".

Multi-Family Home In Windsor Village
$185,000Est. Payment
-- Beds | -- Baths | 2,662 Sqft
36 River Street, Windsor, VT 05089
Multi Family For Sale

Investment opportunity awaits. Two large units, side by side. Live in one side, and pay the mortgage with the rental income. Small yards, and parking for each unit. Nice side porches are a bonus feature. Good rental history and great neighbors.

Lot In Windsor
$74,900Est. Payment
15.1 Acres
Hoisington Hill Road, Windsor, VT 05089
Lots Land For Sale

What a Terrific 15+ Acre Getaway Lot This Is! Incredible Views of Mt Ascutney Looming Very Close By Can Be Greatly Improved with Minimal Clearing. Private Road is in Great Condition. Very Private Setting with Large Acreage Lots Only Nearby. Near Ski Areas and I-91 is Only 10 Minutes Away Providing a Super Spot for Your Getaway! South Facing Lot Could be a Great Solar Site!

Lot In West Windsor
$450,000Est. Payment
29 Acres
Cross Road, West Windsor, VT 05089
Lots Land For Sale

This is the opportunity you've been waiting for! This lovely building parcel has the rare combination of southern exposure, spectacular views, two cleared plateaus, spring-fed pond and a varied inventory of hardwoods, hemlocks and apple trees all encompassed by ancient stone walls, and accessed by a gentle approach. There is a system of interior trails and farm roads making it the ideal property for equine enthusiasts, hikers, cross country skiers and snowmobilers. Enjoy total seclusion with close proximity to paved roads. Just a 3 mile jaunt to the hiking, biking and ski trails of beautiful Mt. Ascutney. Easy access to I-91, Okemo Mountain, Historic Woodstock, Hanover, DHMC and all area recreation. 27 acres enrolled in Current Use program.

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.

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!

Multi-Family Home In Windsor Village
$195,000Est. Payment
-- Beds | -- Baths | 2,973 Sqft
47 River Street, Windsor, VT 05089
Multi Family For Sale

Nice investment opportunity or owner occupy and enjoy the benefits of extra income. Property includes house with 3 well maintained apartments, covered front porch, (5 bay garage with attached workshop and 1st & 2nd floor storage.) Two of the garage bays are rented ($50/month each). Potential extra rental income if you rent the other bays and work shop. Recent improvements include upgraded electric, replaced oil tank, all apartments interior painted, new appliances in two of the apartments, and new carpeting. Also covered storage in the car port at the back of the lot. Town water & sewer. Currently receiving 2700/month rents. Property sits in the flood plain but did not flood in Irene. Owner currently pays $2400/Year flood insurance.

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!

$4,600
Multi-Family Home In Windsor Village
$129,900Est. Payment
-- Beds | -- Baths | 1,700 Sqft
29 River Street, Windsor, VT 05089
Multi Family For Sale

Excellent location! This 2 unit makes this property a perfect investment. Well maintained property with many updates. Just a short walk from downtown, restaurants and other businesses. Plenty of outdoor space to enjoy. Fantastic opportunity to own + occupy and/or add to your investment portfolio! Showings to start Saturday 4/10/21

Multi-Family Home In Windsor Village
$199,900Est. Payment
-- Beds | -- Baths | 2,906 Sqft
1 Maple Street, Windsor, VT 05089
Multi Family For Sale

Wonderful 2 unit duplex! Both units recently renovated, with all separate utilities. This building has a nice level lot, 1 car garage, garden space one enclosed porch with potential of additional finished space! Excellent tenants, to pay the mortgage, this is a turnkey property!

Lot In West Windsor
$450,000Est. Payment
29 Acres
00 Cross Road, West Windsor, VT 05089
Lots Land For Sale

This is the opportunity youve been waiting for! This lovely building parcel has the rare combination of southern exposure, spectacular views, two cleared level fields, a spring fed pond site and a varied inventory of hardwoods, hemlocks and apple trees all encompassed by ancient stone walls, and accessed by a gentle approach. There is a system of interior trails and farm roads making it the ideal property for equine enthusiasts, hikers, cross country skiers and snowmobilers. Enjoy total seclusion with close proximity to paved roads. Just a 3-mile jaunt to the hiking, biking and ski trails of beautiful Mt. Ascutney. Easy access to I-91, Okemo Mtn., Historic Woodstock, Hanover, DHMC and all area recreation. 27 ac. enrolled in Current Use program.

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.

House In Ascutney
$399,000Est. Payment
2.84 Acres
5755 Us Route 5, Weathersfield, VT 05089
Lots Land For Sale

Not just land, but land with a septic system that is Vermont approved for 4,950 gallons a day. Think about it that is over 30 bedroom per day capacity. Great sight for development of over 55 housing or work force 1 bedroom units. Town water at the street and into 2 buildings on the property. The main building a 100 person Theater has been renovated, including an energy audit, new windows, doors, walls, insulation, pellet furnace, roof, side exits on both sides of building, State approved fire permit for commercial building and front exit handicap ramp. Septic system was enlarged and connected to the Theater building & Duplex building. Duplex needs renovation, old restaurant building needs to be torn down, small cottage needs to be renovated. Owner financing available with down payment.

Lot In Brownsville
$175,000Est. Payment
14.33 Acres
0 Brownsvillehartland Road, West Windsor, VT 05089
Lots Land For Sale

Tremendous large building lot privately situated off of paved Brownsville-Hartland Road. This 14.33 acre lot has two open building sites, mixed among existing timber, wonderful bridge crossing the year round brook that runs the entire length of the property and offers endless potential! This property offers both subdivision potential as well as convenience, with easy access to the upper valley. This is a wonderful lot, come and take a look!