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: 3.04% last updated on Apr 15, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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200 Estey Lane Windsor VT 05089

Windsor, VT200 Estey Lane

Price$525,000

Est. Mortgage: $/month

Pending

MLS Number 4855539

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,324

Welcome to 200 Estey Lane, where the views are tremendous, the grounds are immaculate, the garage space is endless, and the canvas is perfectly neutral. This home has it all, and it was built with a care and consideration to storage that is unlike most you've seen. As you wander the grounds, you will find established apple trees, black currants, ponds, and a special array of perennials. From inside, you can capture views of your 25 acres from many rooms, on each level, but the deck and 3 season room may just be the highlight. We will let you decide. Even the finished basement boasts with an authentic Finnish Sauna, and an in-law area with kitchen, just ready for guests. Your new home is waiting!

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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785 County Road Windsor VT 05089

Windsor, VT785 County Road

Price$299,000

Est. Mortgage: $/month

Pending

MLS Number 4850908

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,560

Pristine condition, ideal location, and a community like no other, what more could you ask for.....? Maybe...hardwood floors, cathedral ceilings, gas fireplace, window seats, attached garage, and a basement ready to be finished. It's all here, and these owners are sad to have to go. This home has a drilled well, and is on town septic, the best of both worlds. If you work in the Upper Valley, this is an easy commute down I-91.

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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1097 County Road Windsor VT 05089

Windsor, VT1097 County Road

Price$289,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4847015

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,500

This beautifully renovated cape farmhouse is full of sunshine! The property offers much more than just a gorgeous home, it has an attached garage and barn with heated workshop! Set on a two acre lot of mostly open, gently sloping lawn, the possibilities for outdoor entertainment are limitless. Updated kitchen. The floor plan flows nicely over hardwood floors. Large mudroom with propane stove, first floor laundry, and high ceilings add to the overall comfort of this home. Hand hewn post and beam barn with another garage bay adds plenty of room for whatever your life brings. The enormous loft is ready for your needs, and the fully finished, insulated, heated game room has plenty of southern windows to let that much needed sunshine in. So much to love and appreciate about this property!

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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385 Taylor Drive Windsor VT 05089

Windsor, VT385 Taylor Drive

Price$234,900

Est. Mortgage: $/month

MLS Number 4856048

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,320

This one is immaculate. The open concept is welcoming, the bedrooms are nicely arranged, and the partially finished basement is ready for even more space to enjoy. But... outside, you will find an oasis tucked away from the road. There are 3 bedrooms, including a master suite. The neighborhood will speak for itself, and you will feel right at home.

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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181 Jewett Road Windsor VT 05089

Windsor, VT181 Jewett Road

Price$199,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4854890

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,776

Join us here on Jewett Road, in one of the most desirable neighborhoods. You will be just minutes from town, easy access to I-91, and with the benefits of town utilities. This 2003 Ranch with finished basement is ready for new owners to put their touches in and enjoy it for years to come.

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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119 Ascutney Street Windsor VT 05089

Windsor, VT119 Ascutney Street

Price$199,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4853852

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,044

This village home is ready to go. You'll love the hardwood floors and stone fireplace in the family room, and the room is filled with light and brand new windows. Complete with 4 bedrooms, there is room for everyone. The new boiler is a fantastic addition. You are walking distance to the pond, the school, the fairgrounds, and Paradise Park.

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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 Fairview Avenue Windsor VT 05089

Windsor, VT16 Fairview Avenue

Price$199,000

Est. Mortgage: $/month

MLS Number 4851060

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,205

The yard is spectacular, and so is the neighborhood. There are plenty of bedroom options, and bonus rooms. This home benefits from being walking distance to the fairgrounds, the swimming pond(also amazing kayaking) and the K-12 school. It's all here, just awaiting some fresh paint colors, and a bit of TLC.

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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10 Clough Avenue Windsor VT 05089

Windsor, VT10 Clough Avenue

Price$179,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4847548

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,744

This spacious, low maintenance home in the Village of Windsor offers comfort and convenience. It has an updated kitchen, baths, appliances, hot water heater, oil tank, a new pellet stove and deck with a view of Kennedy Pond, as well as a full unfinished basement perfect for a workshop. The tri level floor plan offers a space for everyone including plenty of room for an office for remote working and a home gym or studio. The home offers a fenced in back yard for the family pet or play area for young children. Various mature berry bushes add to the appeal of this home. Sale includes 2 lawnmowers and 2 snow shovels this is walking distance to schools, the recreation center and downtown restaurants and shopping. A must see!

Listed by Jennifer Snyder, Coldwell Banker LIFESTYLES - Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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2 Day Street Windsor VT 05089

Windsor, VT2 Day Street

Price$169,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4850879

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,300

Located on a dead end street, this home has been well cared. Newly renovated kitchen, bath, and living space opens up the floor plan for comfortable living. With a den and bedroom downstairs, this home has a lot to offer. The detached two car garage has vinyl siding and storage above and the deck off the kitchen is perfect for outdoor dining. The fully fenced in yard comes in handy, as does the short walk to Kennedy pond and the fairgrounds. We look forward to showing you this wonderful opportunity.

Listed by Katie Ladue Gilbert, KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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76 Valley View Terrace Windsor VT 05089

Windsor, VT76 Valley View Terrace

Price$169,000

Est. Mortgage: $/month

Pending

MLS Number 4853385

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,302

Bare trees allow a view of the river! Enjoy mature trees on this 1.10 acre lot in a hidden gem of a neighborhood that is perfect for walking! Interior updates include new laminate flooring throughout with the exception of the bathroom, new light fixtures, paint throughout, new kitchen, dishwasher and microwave, new bathroom vanity and hot water heater & heating unit. We also added a mudroom for convenience coming in from the garage which houses the washer & dryer. Outdoor improvements include new shaker siding on one section. Imagine how cute this home will look with a coat of paint! Nature enthusiasts will love the proximity to Paradise Park with its lake and hiking trails. This home sits conveniently about a mile from the middle of our town of Windsor, VT, which is situated between Claremont and the Upper Valley. Seventeen miles to the VA in White River and 24 to DHMC that goes quickly on interstates 91 and 89. The advantages of being in town & close to the Upper Valley combined with the privacy, nature and quiet setting cannot be beaten. You have over an acre of private lawn to landscape just the way you like! We completed all the improvements named above and the new owner will want to pick up where we left off with projects that will really make it their own. Being offered as is and fully furnished and stocked as we were renting to traveling medical professionals. Being so close to town and the Upper Valley while enjoying such privacy and quiet makes this lot a treasure!

Listed by Dave White, OwnerEntry.com

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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 April 18, 2021.