Windsor VT Real Estate

Windsor  - A small town that is filled to the brim with American history. Windsor’s forefathers played key roles in the foundation of the country, the establishment of the VT constitution, and their industrious nature and determination clearly live on in this tight-knit locality. If you seek community living near the Upper Valley and immersed in a rich past, a home in Windsor, VT, may be right for you.

Windsor VT is a community that offers everything you need to keep your family happy, including the Windsor School District and the award-winning Mt. Ascutney Hospital. Real Estate in Windsor is surrounded by the allure of this historically significant town. Come find out why Windsor has great real estate values and discover the convenience of living here for yourself. Learn more about Windsor.

Windsor VT Homes for Sale

Questions about a property? Give us a call at 802.457.2244!

26 Main Street Windsor VT 05089

Windsor, VT26 Main Street

Price$995,000

Est. Mortgage: $/month

MLS Number 4851384

  • Residential Single Family
  • Construction Existing
  • Bedrooms 9
  • Bathroom 9
  • Square Feet 6,232

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!

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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29 Ascutney Street Windsor VT 05089

Windsor, VT29 Ascutney Street

Price$425,000

Est. Mortgage: $/month

MLS Number 4860908

  • Residential Single Family
  • Construction Existing
  • Bedrooms 8
  • Bathroom 3
  • Square Feet 3,592

New Price! Located in the heart of Windsor-Just steps away from schools, shopping, dining, recreation and town amenities, and 20 minutes from Dartmouth College/Hanover NH and less than 30 minutes from DHMC Lebanon, NH-this stately brick home was completely restored in 2013. Although it is currently operating as a 3-unit with excellent rental history-the extensive and thoughtful renovation was done carefully to preserve original features, central stairway and room layout for future conversion back to the grand primary home with 3-bedroom townhouse apartment if desired. 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 or space for guests-the options are many! 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. Note that .26 Ac conveys and current tax bill reflects .61 Ac Lot.

Listed by Tambrey Vutech, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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72 Harris Road Windsor VT 05089

Windsor, VT72 Harris Road

Price$275,000

Est. Mortgage: $/month

MLS Number 4872922

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,734

This elegant Cape home is tucked back off the road and is sitting on a beautiful landscaped lot. The entire downstairs has been renovated in just the last three years. It is been tastefully redone for single floor living and not a thing has been left untouched. This house is located just outside of town and is practically across the street from the Fairgrounds. The lot is level with a garden and multiple flower beds, a new shed was installed in 2019 with an attached single car carport. The upstairs has yet to see renovations and the two bedrooms are awaiting your vision. Plenty of room, plenty of head space, and plenty of possibilities up there. This home is practical and lovable.

Listed by Chelsea Bevis, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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226 Tracy Farm Road Windsor VT 05089

Windsor, VT226 Tracy Farm Road

Price$249,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4869826

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,536

Beautiful views of Mount Ascutney, quiet, private location but easily accessible to village amenities, the Upper Valley, and I-91. Open floor plan, updated windows, hardwood floors, fireplace and wood stove, wrap around deck. Large open yard, storage shed, mature hardwoods. Just over a mile from the village of Windsor.

Listed by Seth Warren, Seth Warren Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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39 Channing Drive Windsor VT 05089

Windsor, VT39 Channing Drive

Price$235,000

Est. Mortgage: $/month

Pending

MLS Number 4866511

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,008

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.

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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245 Cole Hill Road Windsor VT 05089

Windsor, VT245 Cole Hill Road

Price$235,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4871604

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,200

This home impresses as soon as you approach it. You will see the larger lot with maintained yard, the gorgeous stone patio, the Generac for powering the whole house if the power was ever to go out. Enter from the attached one car garage or side door into a mudroom. The mudroom exits out onto a backyard deck. From there enjoy a large flat backyard. Hike up the small hill and you have access to some pretty wonderful trails! Inside you can easily appreciate the hardwood floors and original trim, a built in cabinet in the dining room, and a splendid fireplace with a Harman pellet stove insert. New windows and new 3/4 bathroom. This combination, with much more, make this home not only charming but desirable.

Listed by Chelsea Bevis, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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8 Timson Avenue Windsor VT 05089

Windsor, VT8 Timson Avenue

Price$199,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4871809

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,296

Don't let the 2 bedrooms slow your search. There is an expansive addition lending the previous living room for a 3rd bedroom. This is a great starter home, within walking distance to all town amenities. Newer roof, finish able space in the basement, and a fenced in yard are a few excellent features.

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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354 Taylor Drive Windsor VT 05089

Windsor, VT354 Taylor Drive

Price$195,000

Est. Mortgage: $/month

MLS Number 4875209

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,603

Secluded wooded setting yet minutes to town. This contempory styled home offers an open concept w/vaulted ceiling, 2 br's plus den, kitchen w/pantry, 1 1/2 baths, french doors to portico deck - handicapped ramp. Immediate occupancy!

Listed by Don Chabot, Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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7 Timson Avenue Windsor VT 05089

Windsor, VT7 Timson Avenue

Price$189,000

Est. Mortgage: $/month

MLS Number 4871808

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 696

Great neighborhood, close to town, and easy to heat. This 2 bedroom Ranch with detached garage is sure to please. Many improvements have been made, including windows siding and kitchen.

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

36 River Street Windsor VT 05089

Windsor, VT36 River Street

Price$175,000

Est. Mortgage: $/month

MLS Number 4874729

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 3
  • Square Feet 2,662

PRICE JUST REDUCED! 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.

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

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Copyright 2021 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. 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. Data last updated August 2, 2021.