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
  • 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: 3.09% last updated on Oct 21, 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
  • Square Feet 3,592
  • Construction Existing
  • Bedrooms 8
  • Bathroom 3

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: 3.09% last updated on Oct 21, 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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17 Buena Vista Court Windsor VT 05089

Windsor, VT17 Buena Vista Court

Price$349,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4878716

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,998

Get ready to feel at home. Between the backyard oasis complete with above ground, hard sided pool and deck to expansive manicured lawns, the exterior is only just the beginning. We start in the mudroom entry area and wander into the gorgeously renovated kitchen with island and plenty of pantry space. Off the kitchen/dining area, you will find the hidden gem of this home with a screened porch that leads to the pool deck. Countless hours are sure to be spent out here. Continue on to the formal dining and living rooms with built ins and pocket doors to characterize the charm of this home. Family gatherings will be making a welcome comeback in these inviting spaces. With 4 large upstairs bedrooms, and 2 bathrooms, everyone will have their own space to relax. The attic office or bedroom area and the partially finished basement are a true bonus.... And, the 3 bay garage with storage above is just what you will need when Winter arrives. You do not want to miss this stately home sitting in a quaint neighborhood, within walking distance to recreation and all town amenities.

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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 Fairview Avenue Windsor VT 05089

Windsor, VT8 Fairview Avenue

Price$265,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4877034

  • Residential Single Family
  • Bathroom 3
  • Square Feet 2,688
  • Construction Existing
  • Bedrooms 4

Sellers withdrew listing before showings for reasons unrelated to this property but are ready for you to come see there beautiful property. Looking for a one of a kind house with plenty of room for the whole family, a yard to stretch out in and located in a convenient location? This is it! Inside this home you'll find the charm of a 1800 house with many modern touches. Formal entry leads you to an open concept living / dining room. Go through the spacious kitchen into a pantry leading you to the converted garage with extra living space. Relax on the three season porch! Upstairs you'll find 2 spacious bedrooms and a bonus room. Outside this house offers a in-ground pool established landscaping, expansive deck and huge corner lot offering tons of flat yard to enjoy. Walking distance to the pond and fairgrounds! Showings begin Thursday 9/16 from 12-2 appointments required. More private showings available Friday 9/17 from 4-6 or Saturday 9/18 from 12-2. All showings must be scheduled.

Listed by Wendie Wright, Coldwell Banker LIFESTYLES - Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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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2073 Route 44 Windsor VT 05089

Windsor, VT2073 Route 44

Price$245,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4876255

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

Single floor living in this well cared for, low maintenance, 3 bedroom home. On an oversized 2.2 acre lot which is about 90% open and landscaped with mature plantings. Great location at the base of Ascutney Mountain just 2.5 mi to the popular Brownsville Butcher and Pantry. Private well, Town sewer, (fee $160 quarterly). The property comes to within 50 feet of the Ascutney State Forest trailhead to the Windsor trail. EZ access to Mt. Ascutney Hosp., and both exit 8 & 9 of Route 91 for easy commute to the Upper Valley or points South. Oak flooring through most of the home. Fireplace in living room. Fresh paint. Roof, windows, siding, insulation & electrical panel all done about 20 yrs ago. Low oil useage. Easy to show.

Listed by Dana Waters and Paula Waters, Dark Horse Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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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4 Meadow Lane Windsor VT 05089

Windsor, VT4 Meadow Lane

Price$244,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4888099

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,072

This split level home just up above the village of Windsor is ready for new love. You'll be pleased to find hardwood floors, an attached garage, plenty of storage, and very little lawn or driveway to maintain. The kitchen and baths can be updated to your own taste, on your timeline. The deck off of the dining room, with new slider, leads you to a private backyard oasis, extending your entertainment space. 3 bedrooms on the main level, with one more potential on the lower level, gives you endless sleeping spaces. Warm up by one of 2 fireplaces in the home.

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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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230 Route 44 Windsor VT 05089

Windsor, VT230 Route 44

Price$225,000

Est. Mortgage: $/month

Pending

MLS Number 4884818

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,440

Cozy home in Windsor with 3 bedrooms, 1 and 3/4 bathrooms and a huge enclosed front porch just across from the Fairgrounds! Entering inside this home into the front porch is the perfect mud room and storage space. Filled with windows that line the whole front wall this room gets amazing lighting and creates a bright and sunny room to greet you into the rest of the home. Your expansive living room is inviting and comfortable with additional seating space and closet storage on one side of the room. Your kitchen includes plenty of counter space, and the updated appliances make it a great spot to cook meals for family and friends, with a great dining rooms just off the kitchen! Stairs off the dining area lead you to the upper level where there are 3 bedrooms, including the master with attached bathroom + laundry and walk in closet. The remaining two bedrooms provide the same cozy feel and round out the upper level. Call today to come check out this charming home!

Listed by Hergenrother Realty Group and Daniel Preston, KW Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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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43 River Street Windsor VT 05089

Windsor, VT43 River Street

Price$207,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4888098

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Square Feet 2,116
  • Bedrooms 4

Come see the beauty of hardwood floors, wide trim, built-ins, and high ceilings. From the moment you walk in, you are welcomed by the grand size of the rooms. You can easily see life happening within these walls. The enclosed three season porch is asking for gatherings or just a quiet drink and relaxation. The extra unfinished space off the main house is awaiting your vision and needs. Laundry hookups on the second floor conveniently join the three bedrooms and full bath. The attic space is sure to "Wow" you at the stairs. Many great upgrades made since 2014, including new boiler, hot water heater and roof. Two large outbuildings are ready for all your things, and so much more to appreciate about this property.

Listed by Chelsea Bevis, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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

Active With Contract

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: 3.09% last updated on Oct 21, 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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23 Coolidge Street Windsor VT 05089

Windsor, VT23 Coolidge Street

Price$99,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4877474

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 833

Cute 2 bedroom home with front and rear porches. Full basement, detached 1 car garage, oil FHA heat and an easy walking distance to Windsor Village amenities. Owner has completed many updates including windows and roof. Are you looking to start investing, or is this your first place to call HOME?

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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 October 27, 2021.