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Windsor VT Real Estate

Windsor, Vermont real estate provides owners with access to a rich history, outdoor recreational opportunities, and unique shops. Popular activities include hiking, biking, fishing, paddling, and snowshoeing. Browse current Windsor, Vermont real estate listings below, including single family homes, multi family homes, and land. You may also be interested in viewing real estate listings in other Vermont towns.

Homes for Sale in Windsor

Contact LindeMac Real Estate at 603-643-4900 if you have questions or would like to schedule a tour. Register to save your favorite listings and get email notifications when similar properties become available.

49 Valley View Trace Windsor VT 05089

Windsor, VT49 Valley View Trace

Price$274,900

Est. Mortgage: $/month

MLS Number 4946303

  • Residential Single Family
  • Square Feet 2,161
  • Bathroom 3
  • Bedrooms 3
  • Construction Existing

Don't miss this opportunity to buy this charming, mid-century Cape Cod home in a lovely neighborhood in Windsor. The home is perched smartly on a little hill overlooking the entry to the neighborhood. Inside, you'll find that it's loaded with built-ins, storage, and nifty mid-century details throughout. This home features large bedrooms on second floor with gleaming refinished hardwood floors with walk-in closets, with one being cedar-lined. The massive living room features a gas burning fireplace with brick hearth will be a focal point for gatherings for family and friends. The large country kitchen is bright and cheery with vintage cabinetry that remain in good shape today. Eating options include a breakfast nook and a formal dining room. The home connects to the two-car garage by a 3 season porch. All of this, situated on one of the very best lots in the neighborhood.

Listed by Ben Durant of KW Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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93 Weston Heights Windsor VT 05089

Windsor, VT93 Weston Heights

Price$192,500

Est. Mortgage: $/month

MLS Number 4946180

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,064

Warm and welcoming 3-BR Cape home is ready for new homeowners. Comfortable sized living room. Large kitchen with plenty of cabinets, counterspace and a dining area. Updated bathroom. First floor bedroom is currently being used as an office. Two bedrooms on the second floor. Full basement with an area that can potentially be finished for a rec room or perhaps a small den. The backyard is partially fenced in and there is room to plant gardens. A short drive to Kennedy Pond. Close proximity to shopping, and restaurants.

Listed by Amy Messina of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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87 Kennedy Drive Windsor VT 05089

Windsor, VT87 Kennedy Drive

Price$249,900

Est. Mortgage: $/month

Pending

MLS Number 4945412

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,215

This home has been lovingly cared for with recent additions including (but not limited to) standing seam roof, new windows, remodeled kitchen nicely combining the old with the new with lots of built-in's. Formal dining room, large living room, first floor bedroom with a remodeled full bath. Upstairs offers two bedrooms and a half bath. Basement offers a family room, laundry area. Lots of storage with an attached 1 car garage with overhead storage, carport and a spacious detached shed. Located at the end of the street giving it a park like feel on 1.5 Acres. Showings start 3/16/23

Listed by Lori Muse of Muse and Associates Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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368 Juniper Hill Road Windsor VT 05089

Windsor, VT368 Juniper Hill Road

Price$499,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4944943

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,535

This home is ready for new owners. It was custom built by a local builder in 2013. It has a spacious open concept on the main level with a half bath and wrap around covered porch for rainy nights or hot summer days. The 2nd level features an expansive primary suite with walk in closet. There are 2 other bedrooms, laundry and another full bath also on this level. The basement has been finished into a family room complete with 3/4 bath and a woodstove. This is an in town location while being just on the outskirts to have a wonderful neighborhood feel, think trick or treating with your crew. The 2 car garage is oversized and enters directly into the house. Open House Sunday 3/12/2023 from 10-1pm. Listing agent is related to the seller.

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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1670 Marton Road Windsor VT 05089

Windsor, VT1670 Marton Road

Price$324,900

Est. Mortgage: $/month

Pending

MLS Number 4943447

  • Residential Single Family
  • Bathroom 2
  • Square Feet 2,156
  • Bedrooms 3
  • Construction Existing

Affectionately named the Hanging Rock Farm, this 3 bedroom Ranch home is sited on 5.49 acres of ideal farm land. Bring your dreams of homesteading, and see all that Marton Road has to offer. Let's name a few: open concept dining and living area, heated sunroom/mudroom, expansive decks to capture the views, just a short drive on a dirt road for privacy, finished basement, workshops, frost free water, 2 sources of heat, a root cellar, a wood chute from the front yard into the basement, and even some attic space for further expansion if wanted. Showings begin on 2/19/23. Come visit during the Open House on Sunday 2/19/23 from 10am-1pm. Offers due Wednesday 2/22/23 at 5pm

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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1240 Juniper Hill Road Windsor VT 05089

Windsor, VT1240 Juniper Hill Road

Price$159,900

Est. Mortgage: $/month

Pending

MLS Number 4942699

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 825

Picture this: A unique and charming country cottage that sits on a partially wooded, level lot, with a stream running in the backyard. Standing seam roof, updated windows and a pellet stove. If this is your first home or you are looking for easy living, come see this gem at the end of Juniper. Showings begin on 2/11. Open House, Saturday 2/11 at 10am - 1pm. Offers are due Tuesday February 14th by 5pm.

Listed by Shawna Fox of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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19 Coolidge Court Windsor VT 05089

Windsor, VT19 Coolidge Court

Price$169,000

Est. Mortgage: $/month

MLS Number 4937453

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,248

Well loved, 3 bedroom, Windsor home with garage/workshop offers a quick commute to the Upper Valley and a short walk to town! This mid-century charmer is ready for your finishing touches, offering bright, sunny rooms and space for the family. Don't wait!

Listed by Heather Ashline of BH&G - The Masiello Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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480 Route 5N Windsor VT 05089

Windsor, VT480 Route 5N

Price$279,000

Est. Mortgage: $/month

MLS Number 4936596

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

This home has been in the same family for the last 54 years. Originally built in 1780, it has had some additions over the years. Situated on a parcel of 12.4 acres, it has great potential for development. The house will need some TLC. First floor has a large eat-in kitchen, dining room, living room, family room, oversize mudroom/utility room, and bedroom. An enclosed porch is the perfect spot to have your morning coffee. The upstairs does have a small second kitchenette area, and 3 bedrooms with an additional enclosed porch, which would be fabulous for summer sleeping! This is a unique and charming property with excellent usable land. The location is perfect for accessing 91, Harpoon Brewery, and the downtown shops and restaurants. Taxes are currently based on 22.4 acres. Seller is retaining 10 acres and property will transfer with 12.4 acres. Cash or Rehab loan.

Listed by Mary Paino of Coldwell Banker LIFESTYLES - Quechee

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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77 Taylor Drive Windsor VT 05089

Windsor, VT77 Taylor Drive

Price$349,000

Est. Mortgage: $/month

Pending

MLS Number 4933364

  • Residential Single Family
  • Construction Existing
  • Bedrooms 8
  • Bathroom 4
  • Square Feet 5,088

A stellar combination: single family manufactured home on its own lot, and a 3 unit building with workshops, storage for tenants, and/or covered parking. There is ample lawn for gardening, easy access to I-91 and all of the Windsor amenities on a paved road, and the heat is paid by the tenants and metered as well. There is even room to add another 1 bedroom with some ingenuity and labor. Currently 3 of the 4 units are rented, with capability for an owners unit(3 beds and laundry)in the main house, or excellent rental potential. Bring your ideas. Long standing tenants, and solar potential. ***some photos online are from before units were rented. ***sold as one, both 77/81 Taylor Drive, with two separate tax bills.

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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

77 Taylor Drive Windsor VT 05089

Windsor, VT77 Taylor Drive

Price$349,000

Est. Mortgage: $/month

Pending

MLS Number 4931491

  • Multifamily
  • Units 4
  • Bathroom 4
  • Acreage 1.93
  • Square Feet 5,088

A stellar combination: single family manufactured home on its own lot, and a 3 unit building with workshops, storage for tenants, and/or covered parking. There is ample lawn for gardening, easy access to I-91 and all of the Windsor amenities on a paved road, and the heat is paid by the tenants and metered as well. There is even room to add another 1 bedroom with some ingenuity and labor. Currently 3 of the 4 units are rented, with capability for an owners unit(3 beds and laundry)in the main house, or excellent rental potential. Bring your ideas. Long standing tenants, and solar potential. ***some photos online are from before units were rented. ***sold as one, both 77/81 Taylor Drive, with two separate tax bills.

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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

96 Cole Hill Road Windsor VT 05089

Windsor, VT96 Cole Hill Road

Price$229,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4926419

  • Residential Single Family
  • Bedrooms 2
  • Construction Existing
  • Bathroom 1
  • Square Feet 924

Set back from the road, and buffered by trees, this cozy 2BR, 1 BA home. Front deck. Eat-in kitchen with plenty of cabinets and counterspace. Nice sized living room with woodstove insert. Full bath. Basement has been started -- finish it off for a game room; potential space for an office. Primarily level yard for gardens, play area or perhaps a pool? Country living atmosphere yet close to Town for shopping, and restaurants.

Listed by Amy Messina of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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

26 Main Street Windsor VT 05089

Windsor, VT26 Main Street

Price$875,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4851384

  • Residential Single Family
  • Bathroom 9
  • Bedrooms 9
  • Construction Existing
  • 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 of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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 TourAsk A QuestionMore Details

Broker Reciprocity 

Copyright 2023 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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 March 28, 2023 7:53 PM EDT