Welcome to Watson Realty & Associates PLC

Sign Up Today!

Get fresh listings via email, save your favorite listings, match with similar properties, and unlock additional property info.

Create Your Account

Do not fill in this field:

Already have an account? Log in

Windsor Vermont Real Estate

Windsor County
Chartered: July 6, 1761
Area: 12,650 Acres = 19.77 Square Miles
Population (US Census, 2000): 3,756
Population Density (persons per square mile): 190

Schools

Windsor Southeast Supervisory Union 802-674-2144
Windsor High School 802-674-6344
Windsor State Street School 802-674-2310

Windsor Vermont is located on the eastern side of the state, right on the border of New Hampshire. Bromley Mountain Resort is just the next town over in Brownsville, Vermont. This Southern Vermont town enjoys the company of the Connecticut River, which winds through the town and the village area. Windsor is the “Birthplace of Vermont,” and the Old Constitution House, where the constitution of the “Free and Independent Republic of Vermont” was drafted, still stands today. Windsor Vermont real estate has Vermont’s best ski resort recreation just a drive away. In an hour or less one can ski or snowboard Ascutney Mountain Resort, Suicide Six Ski Area, Killington Resort, Pico Ski Resort, Okemo Mountain Resort, Magic Mountain Ski Resort, and Stratton Mountain Ski Resort.

Windsor Regional Chamber of Commerce

26 Main Street Windsor VT 05089

Windsor, VT26 Main Street

Price$875,000

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 of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

26 Main Street Windsor VT 05089

MLS Number 4850881

  • Commercial
  • Year Built 1815
  • Acreage 1.1

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 of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

54 Ascutney Street Windsor VT 05089

Windsor, VT54 Ascutney Street

Price$535,000

Est. Mortgage: $/month

MLS Number 4910738

  • Multifamily
  • Square Feet 3,560
  • Units 6
  • Bathroom 6
  • Acreage 0.59

You will be impressed by how well cared for this 6 unit building is. There are 3-1 bedrooms, an efficiency and 2-2 bedroom units. The rents are in line with market rates, and you'll be able to take right over with smooth sailing. We have a 5 year old boiler, standing seam roof, vinyl siding, and vinyl windows. Get excited!

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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

157 Jewett Road Windsor VT 05089

Windsor, VT157 Jewett Road

Price$365,000

Est. Mortgage: $/month

MLS Number 4919003

  • Residential Single Family
  • Square Feet 1,588
  • Bathroom 2
  • Bedrooms 4
  • Construction Existing

Motivated Seller! Fantastic opportunity to live in one of Windsor's most desirable neighborhoods. Built in 2003, this bright and cheerful home has 4 bedrooms and 2 baths -including a bedroom suite on the main living level, hardwood floors, open floor plan, large & practical mudroom, large partially finished basement. Bonus room that is perfect for gaming, office space, storage. Enjoy your dinner on the back deck while your dog roams around the fenced in yard. Good size back yard, with plenty of space for hammock, swing set, above ground swimming pool. Lovely flower gardens in front yard and plenty of space for gardens in the back. Conveniently located just a couple short miles from downtown, this well maintained and ready to move into home is in the perfect "in town, but out of town" location. Less than 3 miles from elementary/high school, downtown Windsor, Interstate 91. Less than 5 miles to Mt. Ascutney Hospital. A stone's throw from Artisan's Park. Easy commute to DHMC, Dartmouth College, VA and other Upper Valley Amenities.

Listed by Rachel Brandli of Fidelity Real Estate Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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

60 State Street Windsor VT 05089

Windsor, VT60 State Street

Price$349,000

Est. Mortgage: $/month

MLS Number 4924324

  • Multifamily
  • Square Feet 3,361
  • Bathroom 4
  • Units 4
  • Acreage 0.23

Excellent opportunity to purchase an investment property with strong rental history and consistent cash flow. Four spacious units with many recent updates. The ideal location is on a tree-lined street and easy walking to local restaurants, shopping and schools. Financials available upon request. 48 hour notice needed for all showings.

Listed by Holly Hall of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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

161 Birch Heights Road Windsor VT 05089

Windsor, VT161 Birch Heights Road

Price$259,900

Est. Mortgage: $/month

MLS Number 4924759

  • Residential Single Family
  • Bedrooms 2
  • Square Feet 1,040
  • Bathroom 1
  • Construction Existing

This one-story ranch plus full basement is set on a quiet cul-de-sac, just 1 mile to the Village of Windsor. Enjoy the large yard with flower and vegetable gardens, covered porch, outdoor deck and fire pit. This home has been well maintained the same owner for over 11 years and it shows!

Listed by Barbara Ruel of Coldwell Banker LIFESTYLES - Quechee

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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

82 State Street Windsor VT 05089

Windsor, VT82 State Street

Price$249,000

Est. Mortgage: $/month

MLS Number 4924323

  • Multifamily
  • Square Feet 2,353
  • Bathroom 3
  • Units 3
  • Acreage 0.23

Unique opportunity to own a turnkey investment property with strong rental history. Three spacious units with many recent upgrades. Large deck overlooking local pond in a lovely residential area. Ample storage and garage space plus walking distance to all that Windsor has to offer. Financials available upon request. 48 hour notice required for all showings.

Listed by Holly Hall of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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

2781 US Route 5 North Windsor VT 05089

MLS Number 4923750

  • Commercial
  • Year Built 1997
  • Acreage 0.48

Tremendous Business opportunity! Zoned "Roadside Business", this former McDonalds restaurant provides countless commercial options. Building is currently empty and ready for immediate occupancy, ample parking, excellent location on Route 5 just north of the Windsor Village. Minutes to I-91, and short distance to the upper valley/Dartmouth region!

Listed by Justin Ranney of Coldwell Banker Homes Unlimited

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

2227 Rt. 5 South Windsor VT 05089

Windsor, VT2227 Rt. 5 South

Price$235,000

Est. Mortgage: $/month

Pending

MLS Number 4910200

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,662

Very Nice well landscaped Gambrel home on .57 acre. Inside you will be pleased with the well kept, recently painted interior and period trim, doors and hardware. A large dinning room and living room with a fireplace and built in bookcase's make for great entertaining for family and friends. Upstairs you will find a very large primary bedroom as well as two more along with a full bath. Out side there is a large side yard and a large lower level area for all your recreational needs. Delayed showings until May18th and 19th. Located only 30 Mins. to all the Upper Valley has to offer and just 15 mins. to Claremont.

Listed by Richard Ballou of The Clerkin Agency,P.C.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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

8/10 Foster Avenue Windsor VT 05089

Windsor, VT8/10 Foster Avenue

Price$234,500

Est. Mortgage: $/month

MLS Number 4903020

  • Multifamily
  • Square Feet 2,608
  • Bathroom 3
  • Units 2
  • Acreage 0.17

This is a great opportunity for investors or homeowners alike. Rent out one side and live in the other, or rent out both for a lucrative income property. Both units have an upstairs, downstairs, and their own separate basements with separate utilities. Units are very similar, with the main difference being #10 has 2 full baths, one upstairs and one down, while #8 has a half bath/ laundry downstairs and a full bath upstairs. Unit #10 has a laundry hookup in the upstairs bathroom as well as in the basement. Each unit has 3 bedrooms upstairs, a great pantry area off the kitchen, and a wide, winder staircase with spacious landings central to the apartment. A level, fenced in backyard with a shed make this a great home for pets, children, and gardening. Home is in close walking distance to food and shopping in downtown Windsor. Seller will consider seller-financing.

Listed by Chelsea Cary of Barrett & Valley Associates,Inc/Sprin

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Broker Reciprocity

Copyright 2022 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 16, 2022 5:41 PM EDT.