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!

1528 Route 5 South Windsor VT 05089

Windsor, VT1528 Route 5 South

Price$1,625,000

Est. Mortgage: $/month

MLS Number 4830038

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 7
  • Square Feet 9,352

Extraordinary opportunity to own one of the 'finest homes in the Upper Valley' formerly known as 'Gilnocky Farm' located in Windsor, the 'Birthplace of Vermont' is private yet convenient to I-91. This home built in 1810 has a wonderfully understated Federal exterior; the interior which was later renovated in the Georgian Revival style, offers 9352 sq ft of living space. Character abounds in large rooms, accented by beautiful 'wavy glass' windows complete with Indian shutters & 'pumpkin pine' floors original to the house. The subtle detail of fine craftsmanship is evident throughout. 10' ceilings, natural light, a lovely foyer, 6 fireplaces, 6 bedrooms, 7 baths, a south facing porticoed porch overlooks the 217.82 acres offering an in-ground pool, 6 car garage, stables w/ 9 stalls, 3 bay closed equipment shed, tennis court, perennials, lawns & pastures, woods and 4-5 miles of equestrian trails. Property is served by town water & sewer, enrolled in the VT current use program and conserved with Upper Valley Land Trust.

Listed by Dana Waters and Paula Waters, Dark Horse Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 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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153 Pembroke Road Windsor VT 05089

Windsor, VT153 Pembroke Road

Price$1,195,000

Est. Mortgage: $/month

MLS Number 4819544

  • Residential Single Family
  • Construction Existing
  • Bedrooms 17
  • Bathroom 21
  • Square Feet 14,000

The Windsor Mansion, sits high on Juniper Hill within the town limits of the historic hamlet of Windsor, Vermont. Built in 1902 by prominent New York lawyer Maxwell Evarts and listed on the National Register of Historic Places, it has welcomed countless distinguished guests in its storied past including Presidents Theodore Roosevelt, Woodrow Wilson, and Calvin Coolidge. The stately 17-bedroom Colonial Revival home is perched on 14 private acres replete with breathtaking views of Lake Runnemede, the Cornish Hills, and Mount Ascutney. A recent million dollar+ restoration and renovation project, though large in scale, beautifully preserved the elegant historic integrity of the original design while complementing with state-of-the-art modern amenities. Sprawling lawns with impeccably manicured gardens and an expansive deck and patio overlooking the Connecticut River Valley make it the perfect setting for entertaining friends and family. Currently the property is operating as an Inn but could also make a spectacular large family home. Only 19 miles to Hanover, NH/Dartmouth College and 16 miles to Woodstock, Vermont, Windsor Mansion is centrally located to all the best that the Upper Valley and New England have to offer.

Listed by David Donegan, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 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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1672 Hunt Road Windsor VT 05089

Windsor, VT1672 Hunt Road

Price$905,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4791655

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 5,265

Kimball Brook Farm, C. 1789, has a storied history. It was once the residence of author and music critic Marcia Davenport, and is featured in her 1967 autobiography, “Too Strong for Fantasy”. Residents of Windsor report that Katherine Hepburn, a long-time friend of Ms. Davenport's was a visitor to the farm. This spectacular home embodies rambling country elegance and provides generous amounts of room for entertaining, family gatherings and/or events. Kimball Brook is comprised of 8 bedrooms and 5 baths - a total of 5,300 sq feet. There are both large formal areas and cozy spaces, which along with its 5 working fireplaces, highlight the farm's classic Vermont country character. The systems and structure, including heat, water, roofing, siding, foundation, and security have all been intelligently updated with state-of-the-art systems and materials. The large antique barn is a remarkable entity, providing space for projects, animals, vehicles, or celebrations. The property is nestled in a quiet valley amidst the rolling hills of historic Windsor on 32 ac of mixed open and wooded land, overlooking a pond with views into New Hampshire. It is a very short walk (or snowshoe, or bike ride) to an 900+ acre State Wildlife Management Area that provides the many year-round, outdoor activities enjoyed by all Vermonters. Despite its privacy and tranquility, the farm remains easily accessible to local attractions, including Hanover, NH and Woodstock, VT, both within 20 minutes.

Listed by Seth Warren, Seth Warren Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 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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2469 US Rt. 5 North Windsor VT 05089

Windsor, VT2469 US Rt. 5 North

Price$349,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4842425

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,736

Sitting just North of the village of Windsor, this 1805 Greek Revival is sure to entice your sense of prestige and distinction. This home boasts a beautiful kitchen, front and back parlors, endless bedroom options, office space, expansive yard for gardening or playing with the kiddos, and garage/barn space that lends itself to working nicely for a business entity. With endless historic notations, including the National Historic Registry, you will feel the character and charm of years gone by, with simple touches being added by each owner. Bring your own ideas and make this one HOME.

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 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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16 Enright Avenue Windsor VT 05089

Windsor, VT16 Enright Avenue

Price$174,900

Est. Mortgage: $/month

Pending

MLS Number 4835056

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

This could be exactly what you have been waiting for! Three bedroom home located just outside of town, in a desirable neighborhood. Walking, you are just minutes from the town Fairgrounds and beautiful Kennedy Pond. Safely walk to school. The covered three season porch welcomes you as you enter the home, and the flow of the first floor makes it functional for all. Three bedrooms upstairs with a full bath. Great size lot with endless possibilities. Add a one car garage to the mix and we have the whole package ready for new owners!

Listed by Gerry Stark, RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 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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133 State Street Windsor VT 05089

Windsor, VT133 State Street

Price$174,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4843534

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

Convenient location - walk to school and town. Nice open floor plan w/ hardwood floors, bay window, 3 br's, 2 baths & enclosed porch.

Listed by Don Chabot, Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 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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667 County Road Windsor VT 05089

Windsor, VT667 County Road

Price$115,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4842514

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,596

Time for a new family to love this home, and make it their own. The lot may be small, but Paradise Park is just a short walk out your front door. With 4 bedrooms, 2 baths, and an office, this is a steal of a deal to do your own cosmetic upgrades!

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 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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59 Weston Heights Windsor VT 05089

Windsor, VT59 Weston Heights

Price$110,000

Est. Mortgage: $/month

MLS Number 4844440

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

This classic cape is located in nice neighborhood off the beaten path, but still close to all town amenities and the Upper Valley. Three to Four bedrooms, first floor bathroom, detached garage and level back yard. With some updating and cosmetics you will have a fine place to call home. Well priced and easy to show!

Listed by Judith Thompson, Walnut Hill Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 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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25.5 Union Street Windsor VT 05089

Windsor, VT25.5 Union Street

Price$95,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4838929

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 900

CHECK OUT THIS PRICE! Are you looking for your first investment? Don't miss this great opportunity. Investors take NOTICE: could be a great easy 2 bedroom rental...Easy to clean, easy to heat, easy on the eyes, easy walk around the village of Windsor, and easy on the wallet for mortgage payments. Why rent when you could own? Vinyl windows, and new siding. New roof and furnace!! New concrete pad added for a garage.

Listed by Gerry Stark, RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 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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11 Maple Street Windsor VT 05089

Windsor, VT11 Maple Street

Price$89,500

Est. Mortgage: $/month

Active With Contract

MLS Number 4788840

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,210

Affordable village home with 2 br's, 1.5 baths, applianced, eat-in kitchen and a walk to school and shopping location. Maintenance free vinyl siding and standing seam roof. Owner says sell!!!! Price reduced

Listed by Don Chabot, Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 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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31 Bridge Street Windsor VT 05089

Windsor, VT31 Bridge Street

Price$79,500

Est. Mortgage: $/month

Active With Contract

MLS Number 4842651

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,636

ESTATE SALE 3BR's, formal DR, large LR, attached shed and garage. Home needs major renovations. Conventional Financing only.

Listed by Don Chabot, Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.77% last updated on Jan 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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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 January 22, 2021.