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!

3652 Route 44 Windsor VT 05089

Windsor, VT3652 Route 44

Price$415,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4740732

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,986

Well maintained Dutch Colonial sited on 10.2 beautifully landscaped acres with mountain views. Step inside and enjoy the hardwood floors, exposed wood beams and open concept kitchen/dining room that allows guests to step outside onto the deck that overlooks the open fields below. A large living room with cathedral ceiling and a gas burning stove is the perfect place to gather with friends and family. First floor master bedroom with walk-in closet, full bath, laundry and two bedrooms complete the first floor. Upstairs, two additional rooms, 3/4 bath and a loft will be the perfect spot for your out-of-town guests. The lower walkout level provides a large, dry heated space for storage and a two car garage. Outside, walkout onto the plush green lawn with mature perennial gardens, hand picked stone walls, a small apple orchard, and a private little sitting spot overlooking the babbling brook. The private back yard hides the full length multi-level decks that drop down to the above ground pool and allows plenty of space for entertaining and outdoor grilling. Walk down to the lower back yard and you will find a 24x30 Post and Beam barn with electricity and hay storage above. Just a few steps away from the blueberry and raspberry patch sits a 35 year old sugar shack and small maple orchard. It is here where maple syrup and memories were made by a family who has loved and cared for this home. Less than one mile to Mt. Ascutney, 30 minutes to DHMC, and 20 minutes to GMHA.

Listed by Annette Hartley-White and Jon Merrill, Four Seasons Sotheby's Int'l Realty

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$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 2019
* 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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165 State Street Windsor VT 05089

Windsor, VT165 State Street

Price$410,000

Est. Mortgage: $/month

MLS Number 4760823

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 6
  • Square Feet 4,182

They don't build houses like this anymore. This amazing colonial revival house has been updated to like-new condition while maintaining the period charm. High ceilings, wood floors, custom built-ins, chandeliers, this house has it all. The recently remodeled kitchen features custom cabinetry reproduced in the style of existing woodwork in the house. Completely private location just minutes from the town center, and within 30 minutes of Dartmouth College and downtown Woodstock. Fabulous mountain views!

Listed by Kyle Arnold, BHG Masiello Brattleboro

$
$
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$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 2019
* 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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2151 Hunt Road Windsor VT 05089

Windsor, VT2151 Hunt Road

Price$396,000

Est. Mortgage: $/month

MLS Number 4765375

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,456

It doesn't get much better than this view! Privately situated on 4.5 level acres with multiple outbuildings and a beautiful pond. This well cared for home has had the same owners for 35 years who have taken meticulous care of the property. Stand out features include a large kitchen, open concept floor plan, spacious master suite, wrap around deck, attached 2 car garage and a full walkout basement. If this wasn't enough you'll also find a 1 bedroom apartment space above the attached garage that could be converted into more living space if desired. This truly is Vermont living at its best.

Listed by Wendie Wright, Coldwell Banker LIFESTYLES - Hanover

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 2019
* 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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418 Moonrise Hill Road Windsor VT 05089

Windsor, VT418 Moonrise Hill Road

Price$285,000

Est. Mortgage: $/month

MLS Number 4733786

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,740

Rare to find a home with great views AND a flat driveway! Near end of road setting with commanding views over your own fields of Ascutney Mountain. 3 bedroom 3 bath home with enclosed porch. 2 car under. Lots of storage. New roof about 10 yrs ago. New boiler. Owned solar system. There is a Vermont Castings wood stove, and a outdoor wood boiler not currently being used. Potential horse property. Fields and gravel roads. Great location close to Windsor Village and the Hospital. Easily commutable to the Upper Valley. Priced below assessment.

Listed by Dana Waters, Dark Horse Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 2019
* 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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3 Old Mill Pond Road Windsor VT 05089

MLS Number 4759426

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 2,581

This condo unit is located in one of the most private and scenic settings in our area. Located in the birthplace of Vermont, a charming, historic town, yet set far away from it all. This condo has new flooring, ample storage, 2 fireplaces, a skylight and pond in your backyard for non-motorized boats. Its spacious rooms are full of natural light and the back deck is overlooking the pond, and it has enough room to gather with a crowd. There are essentially 3 master suites, all with full bathrooms, and another office space on the basement level that has a shower, perfect for after using the pool. This is a special unit with an attached garage on the ground floor level, the only one of all 12 units. With so many added benefits, including the entire full basement with bar and gas fireplace and full laundry room with wash basin, this unit is sure to impress. Close proximity to Dartmouth College, Dartmouth Hitchcock and all Upper Valley Amenities. Windsor is home to a grocery store, drugstore, a bit of shopping, eateries, and a 9-hole golf course, but if you seek more, several options are but 20 minutes away. And, if skiing strikes your fancy, there are endless options all within 45 minutes away, for all levels of enthusiasts. Let this be your home away from home.

Listed by Katie Ladue Gilbert, RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 2019
* 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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221 US 5 North Route Windsor VT 05089

Windsor, VT221 US 5 North Route

Price$189,900

Est. Mortgage: $/month

MLS Number 4770133

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,152

This house has all you need to settle in and enjoy everything the area has to offer. With I-91 just seconds away, you have access to the Upper Valley in minutes, yet set off enough to listen to the quiet. This home has hardwood floors throughout, a large foyer, and a fireplace in the living room. The potential for income from an unfinished apartment space above the garage make this home a contender, and a great opportunity.

Listed by Katie Ladue Gilbert, RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 2019
* 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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3 Front Street Windsor VT 05089

Windsor, VT3 Front Street

Price$189,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4767033

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 2,800

Just over the river from NH and close to I-91, this home is just enough away from downtown to get a true neighborhood feel, but close to the schools, restaurants and Ascutney Hospital. This is a true family home. Lot of room to spread out, 3 bedrooms with a bonus room in the attic that can be used as a 4th bedroom or play room. Move in as is or this home would be incredible with some thoughtful updates! Nice size fenced in yard which is great for BBQ's, children and pets! *Subject to 3rd Party Approval

Listed by Amy Gamache, Keller Williams Realty Metropolitan-Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 2019
* 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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33 Central Street Windsor VT 05089

Windsor, VT33 Central Street

Price$149,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4773877

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,436

Fall is here, and so are the lower prices. This house is full of updates and quality renovations. You will find Quartz in the kitchen and granite in the Master Suite's bathroom. The wood stove, clawfoot tub, tile flooring and walk-ins all add to the tasteful completion of renovations. The insulation, chimney, windows, electrical and roof, and all plumbing have also been updated. The charm and quality in this home will undoubtedly bring pride and joy to just about everyone. You have to see the inside to fully appreciate everything this home has to offer.

Listed by Katie Ladue Gilbert, RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 2019
* 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 Day Street Windsor VT 05089

Windsor, VT17 Day Street

Price$129,900

Est. Mortgage: $/month

MLS Number 4785021

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 2
  • Square Feet 1,160

Located on a dead-end road, is this 2 BR / 1.5 BA Dutch Colonial-style home. Home includes a nice-sized enclosed front porch as well as a side deck. Living Room has an adjacent area which could be an open dining area. Large kitchen with dining area. First floor includes a half bath. Second floor includes two bedrooms and full bath. Full basement. Detached shed. Level land as well as sloping and somewhat steep in the back of the house. Nice location with its convenience to Kennedy Pond, downtown Windsor Village with its shops and restaurants. Short drive to I-91 Ext 9

Listed by Amy Messina, Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 2019
* 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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159 State Street Windsor VT 05089

Windsor, VT159 State Street

Price$127,900

Est. Mortgage: $/month

MLS Number 4759404

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1,514

It is officially Fall, and more than the leaves are dropping! NEW PRICE, owner says sell! This is a well maintained, updated home. It is located in town, yet set back from the main road, bringing a sense of privacy. It is a comfortable size with endless character and charm. Bring your gardening tools to put a fresh spin on the landscaped, terrace gardens. Walk into town, school, recreation center, Paradise Park and even the pond for swimming.

Listed by Katie Ladue Gilbert, RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Dec 12, 2019
* 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 A VisitAsk A QuestionMore Details

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Copyright 2019 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 December 15, 2019.