Windsor

Explore the latest real estate for sale in Windsor, Vermont. If you have any questions or if you'd like to see any of these properties in person, call 802-760-3100 or contact us online.

Create a free account to save your favorite Vermont real estate listings and get notified when similar properties become available.

1672 Hunt Road Windsor VT 05089

Windsor, VT1672 Hunt Road

Price$905,000

Est. Mortgage: $/month

MLS Number 4791655

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 8
  • Bathroom 5

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 of Seth Warren Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

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
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 2

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 of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

165 State Street Windsor VT 05089

Windsor, VT165 State Street

Price$410,000

Est. Mortgage: $/month

MLS Number 4760823

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 5

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 of BHG Masiello Brattleboro

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

26 Depot Windsor VT 05089

MLS Number 4744741

  • Commercial
  • County Windsor
  • Acreage 0.31

"Once in a lifetime," beautiful historical restaurant property "Windsor Station" for sale! Housed in classical Train Station at an active Amtrak stop in the beautiful town of Windsor VT! Ambiance of a Victorian era Depot and decorated with period railroad paraphernalia, this restaurant has a seating capacity for 84. Popular local area restaurant and bar just a short drive from Interstate 91 exits 8 or 9. Popular restaurant that attracts sight and fall foliage seekers, skiers as well as locals from the Upper Valley, Claremont and Woodstock VT areas! Unparalleled reputation for great food, craft beers and entertainment! Owners currently operate dinner only but potential for increased revenue if opened for lunch and breakfast! So much more potential with expansion to covered portion of the Depot structure or outdoor seating!

Listed by Roz Caplan of Century 21 Highview Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

2151 Hunt Road Windsor VT 05089

Windsor, VT2151 Hunt Road

Price$396,000

Est. Mortgage: $/month

MLS Number 4765375

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3

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 of Coldwell Banker LIFESTYLES - Hanover

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

418 Moonrise Hill Windsor VT 05089

Windsor, VT418 Moonrise Hill

Price$279,000

Est. Mortgage: $/month

MLS Number 4791528

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3

This single family home is a rare find with a commanding view of Mt. Ascutney, but with only a short, flat driveway to plow. The 5.8 acres consists of both fields and woods. 3 large bedrooms and 3 full baths home with an enclosed porch. There is lots of storage and a full basement. A new roof was put on about 10 years ago. New boiler last winter and an owned solar system. There is a Vermont castings wood stove inside and an outdoor boiler ( that is not currently being used). This is a potential horse property with fields and gravel roads. While the property is located at the end of a road, it is less than 2 miles from Windsor Village, school and the hospital. Easy commute to upper valley. Why pay their prices? Priced below assessment.

Listed by Jason Saphire of www.EntryOnly.com

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

3 Old Mill Pond Road Windsor VT 05089

MLS Number 4759426

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 4

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 of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

3 Old Mill Pond Windsor VT 05089

MLS Number 4759424

  • Condo
  • County Windsor
  • Bedrooms 3
  • Bathroom 4
  • 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 of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

221 US 5 North Route Windsor VT 05089

Windsor, VT221 US 5 North Route

Price$189,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4770133

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 2

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 of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

55 Main Windsor VT 05089

MLS Number 4782518

  • Commercial
  • County Windsor
  • Acreage 0.68

Downtown commercial / retail building on large level lot with plenty of onsite parking. Main building is 30X60, large windows, heated and cooled by heat pump, open span, on slab, 1/2 bath, presently utilized as a bicycle / ski retail / repair shop. An unfinished building behind the main building was formerly a car wash, has two tall drive-through doors, high ceiling, on slab, 18X36.

Listed by Seth Warren of Seth Warren Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

1-3 Central Windsor VT 05089

Windsor, VT1-3 Central Street

Price$179,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4785558

  • Multifamily Multi-Family
  • County Windsor
  • Property Type Multi-Family
  • Bathroom 4
  • Square Feet 3,531

Excellent investment property with good rental history net operating income before debt service is $31956 17.76 % cap rate

Listed by Don Chabot of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

51 State Windsor VT 05089

Windsor, VT51 State Street

Price$169,900

Est. Mortgage: $/month

MLS Number 4785589

  • Multifamily Multi-Family
  • County Windsor
  • Property Type Multi-Family
  • Square Feet 3,097
  • Acreage 0.63

Great location - ideal for owner occupied w/a 3 br apt on 2nd floor. Harvey replacement windows and buderus boiler. Great upside for additional income for investor.

Listed by Don Chabot of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

9 Day Street Windsor VT 05089

Windsor, VT9 Day Street

Price$160,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4790370

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 1

Set up and away from downtown and on a dead end street. The street is quiet and the rooms fill with southern sun. The open kitchen layout welcomes you from the mudroom and into a home with maple wood floors, tastefully painted walls and great living spaces. Upstairs you will find all three bedrooms and a brand new full bath. The master bedroom also includes attic access from a walk-in closet. The attic has ample storage space. The in-ground pool is well maintained and the back yard is entirely fenced in. This home has great potential and is a beautiful place to live.

Listed by Katie Ladue Gilbert of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

101 Main Windsor VT 05089

MLS Number 4510101

  • Commercial
  • County Windsor
  • Acreage 0.2

Diverse commercial space ready to have new owners move in and add to the long list of successful businesses that have graced these buildings. From Blacksmithing to a Point Shop and on to Plumbing, Guns, Woodworking, and so much more. If you've been thinking about having a great store front, and plenty of storage, now is the time to JUMP. Come join Windsor's growing economy, all while being 4 miles to I-91. Owner will consider seller financing.

Listed by Katie Ladue Gilbert of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

159 State Street Windsor VT 05089

Windsor, VT159 State Street

Price$127,900

Est. Mortgage: $/month

Pending

MLS Number 4759404

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 1

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 of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

11 Maple Street Windsor VT 05089

Windsor, VT11 Maple Street

Price$95,000

Est. Mortgage: $/month

MLS Number 4788840

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 2
  • Bathroom 2

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 of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

21-23 Maple Windsor VT 05089

Windsor, VT21-23 Maple Street

Price$75,500

Est. Mortgage: $/month

Active With Contract

MLS Number 4787301

  • Multifamily Multi-Family
  • County Windsor
  • Property Type Multi-Family
  • Bathroom 2
  • Square Feet 2,835

Priced to Sell! Consider this 2-unit property as an investment property. Both units are currently rented. Each unit has its own covered back porch. LR, large eat-in kitchen[s] on first floor. Two bedrooms on second floor with full bath. Convenient location to Route 5 for shopping, restaurants and a short distance to Exit 9/I-91.

Listed by Amy Messina of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

2045 Route 5 South Windsor VT 05089

MLS Number 4786552

  • Multifamily Multi-Family
  • County Windsor
  • Property Type Multi-Family
  • Square Feet 3,488
  • Acreage 2.46

Excellent potential for redevelopment, 2.46 acres , major road frontage, public water and sewer at site. Presently assessed as a 2 family, easily room for 2 more unis in the existing bldg. Past uses were a in home business, county stop restaurant, cattlemans' restaurant and the top hat. The lower rear section of the property could be used for huge garden space. Building needs total rehab but the future uses make the potential unlimited. Town assessment is $187,260. Now available for $75,000, opportunity is awaiting. Owner may consider short term financing

Listed by Don Chabot of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

282 Jewett Windsor VT 05089

Windsor, VT282 Jewett Road

Price$49,900

Est. Mortgage: $/month

MLS Number 4695880

  • Land
  • County Windsor
  • Property Type Land
  • Acreage 0.7

Come ready to build in the desirable Juniper Heights development. Let this lot be yours. Owner has already designed for a 3 bedroom, 2 bathroom Ranch style home. Town water and sewer and power is ready at street.

Listed by Katie Ladue Gilbert of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

Broker Reciprocity

Copyright 2020 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 February 18, 2020.