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$875,000

Est. Mortgage: $/month

MLS Number 4851384

  • Residential Single Family
  • Bathroom 9
  • Construction Existing
  • Bedrooms 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

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$
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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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3039 Route 44 Windsor VT 05089

Windsor, VT3039 Route 44

Price$485,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4926625

  • Residential Single Family
  • Construction Existing
  • Square Feet 1,398
  • Bedrooms 2
  • Bathroom 2

MNT ASCUTNEY VACATION GETAWAY! Meticulously designed & constructed contemporary sited directly on the Mountain with beautiful private views of the Vermont countryside. This home comes fully furnished and has direct access to hiking & biking and is ready for your immediate enjoyment as a second home & will be an ideal Airbnb rental. There is a great open floor plan with cathedral ceilings, tons of natural light, & pine floors throughout. The sliding glass doors open to a covered, wrap around porch & stone patio/firepit with plenty of space for entertaining, dining, and watching the sun set. The entryway mudroom has generous built-in storage with laundry and the kitchen boasts beautiful soapstone counters, self-closing drawers, and luxury Italian stainless steel gas range and dishwasher. The living room/dining room has a mounted TV and custom gas Jotul fireplace perfect for cold winter nights. The elegant first level bathroom has a huge walk-in rainfall shower with slate tiles & teak mats. There is a first level bedroom that accommodates 2 bunkbeds and the second level hosts a private master suite with walk-in closet/dressing room, 3/4 bath, & balcony. The large basement has a wide interior staircase access for easy expansion and the home is equipped with whole house air conditioning and heat pump technology. This home is a perfect getaway with Mt. Ascutney State Park & Ascutney Outdoors Center offering access to outdoor recreation year-round and is a short drive to Woodstock.

Listed by Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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148 Hewett Road Windsor VT 05089

Windsor, VT148 Hewett Road

Price$449,000

Est. Mortgage: $/month

MLS Number 4931395

  • Residential Single Family
  • Bathroom 3
  • Construction Existing
  • Bedrooms 2
  • Square Feet 1,500

Nice horse property, privately sited log home on 11.4a, southern exposure, view of Mt Ascutney. Open concept kitchen, dining & living room with pellet stove; laundry & half bath on 1st level. 2 bedroom, 2 baths up. Direct entry, attached 2 car garage. Nice 3 stall horse barn with overhang, tack room, hay loft, electric & water. Small ring, open pasture, partially fenced with good dirt road access in Windsor. Consolidated Communications DSL internet @ 25 mbps.

Listed by Dana Waters and Paula Waters, Dark Horse Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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38 Ascutney Street Windsor VT 05089

Windsor, VT38 Ascutney Street

Price$439,000

Est. Mortgage: $/month

MLS Number 4923435

  • Residential Single Family
  • Bedrooms 5
  • Square Feet 3,040
  • Bathroom 3
  • Construction Existing

Price Just Reduced, don't wait! There is always a home in every small town that everyone would love to tour. Windsor has a few gems, and this home at 38 Ascutney St. is one of them. This garden oasis, with charming wrap around porch complete with screened in sitting area and rocking chairs will be a home you cannot miss seeing. Drive in the tree and flower lined driveway to find a backyard that you never knew existed, bursting with fruit trees, and blueberry bushes, even irrigation. The pool may be closing soon for the season, but you can stargaze by the firepit. Plenty of parking with a detached 2 car garage and paved driveway. It's time to stroll through this exquisite home. First stop is the entry way with built in storage, then on to the kitchen with custom concrete countertops and plenty of space to entertain as the room leads into the gorgeous sunroom. The main level finishes off with a formal dining and living room and 3/4 bath. On the 2nd level, there are endless bedroom options, laundry and even a den. There is an attic bedroom with 1/2 bath. The home boasts the 19th century charm(think pocket doors and built ins), with modern updates (windows and newer roof on much of the home).

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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157 Jewett Road Windsor VT 05089

Windsor, VT157 Jewett Road

Price$365,000

Est. Mortgage: $/month

Pending

MLS Number 4919003

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

Motivated Seller! Easy living in this nicely maintained one-level home in one of Windsor's most desirable neighborhoods! Wonderfully located on a quiet street close to Hartland and the heart of Windsor, you're nicely tucked away, yet still very close to the hospital, schools as well as shops and restaurants. 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, Fidelity Real Estate Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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2787 Route 44 Windsor VT 05089

Windsor, VT2787 Route 44

Price$339,000

Est. Mortgage: $/month

MLS Number 4931948

  • Residential Single Family
  • Square Feet 2,586
  • Bathroom 2
  • Bedrooms 3
  • Construction Existing

A Unique Double A-Frame Home on 2.8 acres backing up to Ascutney State Park! This 3 bedroom, 2 bathroom home is within minutes to the Town of Windsor, Village of Brownsville, Ascutney Outdoors, Brownsville Butcher and Pantry, and countless outdoor recreational opportunities. The home sits surrounded by mature trees which provide a feel of cozy seclusion, and even has a koi pond! The ample yard space is great for entertaining, gardening, pets, a swing set, and potential storage. Once inside you'll see the kitchen has a convenient island, gas-range, and double door refrigerator. The kitchen flows directly into the dining and living area, with a large stone fireplace as the centerpiece. The upper floor consists of 3 nice sized bedrooms with a full bathroom. The basement has been finished, and currently being used as a rec. room/gym but the possibilities are endless. Such a wonderful location with so much to offer! OPEN HOUSE 10/8/22 1-4!

Listed by Andrew Hubbell, Vermont Real Estate Company

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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172 State Street Windsor VT 05089

Windsor, VT172 State Street

Price$329,900

Est. Mortgage: $/month

Pending

MLS Number 4929795

  • Residential Single Family
  • Square Feet 2,074
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing

Traditional craftsman style home that will leave you feeling warm and invited. Enter from the covered porch into the kitchen with plenty of workspace. The sunlight seems to find every nook and cranny, and fills both the dining room and living areas. The built ins may remind you of the age of this beauty, but the replacement windows, fireplace and modern updates remind you that you will be cozy here. Tucked up off of State Street, you may not even know that this 3 bedroom, 1.5 bathroom oasis existed. We invite you to sit on the back porch, enjoy the landscape, and think about next years gardens. Offers due by Tuesday, 9/20/2022 5pm.

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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161 Birch Heights Road Windsor VT 05089

Windsor, VT161 Birch Heights Road

Price$259,900

Est. Mortgage: $/month

Pending

MLS Number 4924759

  • Residential Single Family
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,040
  • 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, Coldwell Banker LIFESTYLES - Quechee

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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7 Fairview Avenue Windsor VT 05089

Windsor, VT7 Fairview Avenue

Price$239,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4924840

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,984
  • Construction Existing

This well maintained cape has so much to offer. Inside you'll find 3 bedrooms on the same floor and a large den on the main level, functional kitchen, formal dining room and a large pantry or storage area. With 2 three season porches the home provides tons of space. Located on a spacious level lot, walking distance to recreation areas and a short distance from downtown Windsor. Showings begin Friday 8/12 from 10:00-12:00, Saturday 8/13 10:00-12:00 and Sunday 8/14 from 12:00-2:00.

Listed by Wendie Wright, Coldwell Banker LIFESTYLES - Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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96 Cole Hill Road Windsor VT 05089

Windsor, VT96 Cole Hill Road

Price$225,000

Est. Mortgage: $/month

MLS Number 4926419

  • Residential Single Family
  • Bathroom 1
  • Bedrooms 2
  • Construction Existing
  • Square Feet 924

Set back from the road, and buffered by trees, this cozy 2BR, 1 BA home. Front deck. Eat-in kitchen with plenty of cabinets and counterspace. Nice sized living room with woodstove insert. Full bath. Basement has been started -- finish it off for a game room; potential space for an office. Primarily level yard for gardens, play area or perhaps a pool? Country living atmosphere yet close to Town for shopping, and restaurants.

Listed by Amy Messina, Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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2 Terrace Street Windsor VT 05089

Windsor, VT2 Terrace Street

Price$220,000

Est. Mortgage: $/month

MLS Number 4932066

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Square Feet 1,728
  • Bedrooms 4

Several generations have enjoyed the quiet comfort of this quaint New England home. The current owner has lived here since 1962. It's that loved! A perfect place to take in the outdoors as there are so many options for recreation to choose from. It's like the old neighborhood with youngsters riding their bikes safely on the dead end streets or walking to neighborhood Mill Pond only a kids minute from the front door. How about hopscotch in the middle of the road because there are only 2 other homes on a street where neighbors still come out and chat and lend a helping hand. It's a Town of Mayberry setting if there ever was one in today's fast paced world. The home has 4 good sized bedrooms with an option for a 1st floor bedroom or office. Natural woodwork and hardwood floors speak to an era where quality craftsmanship was a standard in home building. The "attic" is asking for someone to breath life into it by bringing heating and drywall to a space which would make a stunning primary bedroom suite with village and possibly pond views. There is so much to love about the charm, style and grandeur of this generational home. Come see all it has to offer and with a little polish, she will be stunning!

Listed by Leila Tarantelli, Keller Williams Coastal Realty/ Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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15 Fairview Terrace Windsor VT 05089

Windsor, VT15 Fairview Terrace

Price$210,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4925862

  • Residential Single Family
  • Bedrooms 3
  • Square Feet 1,270
  • Construction Existing
  • Bathroom 1

Located on a quiet cul-de-sac, walking trails, close to Mill Pond with beach access and boat launch, one mile walk to shops and restaurants. This home has been well maintained, wood floors throughout, additional 14' x 16' storage room attached to the back of the house, 2-car garage with separate attached tool shed, garden shed, full basement for laundry and crafts and more storage. The separate, sunken family room has a propane stove, the perfect cozy media room.

Listed by Barbara Ruel, Coldwell Banker LIFESTYLES - Quechee

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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

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Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. 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 October 5, 2022 2:09 AM EDT.