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Windsor VT Real Estate

Situated beside the Connecticut River on the New Hampshire border, Windsor is a historic town in Windsor County, Vermont. Known as the “Birthplace of Vermont”, in 1777, the Constitution of Vermont was adopted in Windsor thus founding Vermont as a sovereign state until it eventually became part of the U.S in 1791. Today, the close-knit community of Windsor embraces its heritage with several attractions featuring its rich history. Those who reside in Windsor enjoy the peaceful atmosphere among the beautiful, rural scenery. 

Search the latest real estate in Windsor, Vermont with Maple Sweet Real Estate. Find the right property for you from a variety of listings. ‚ÄčRegister to save your favorite listings and you can get email notifications when similar properties are posted. Have an account? Log in here.

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26 Main Street Windsor VT 05089

Windsor, VT26 Main Street

Price$875,000The price has recently decreased

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 of KW Vermont Woodstock

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.3% last updated on 2022-05-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

26 Main Street Windsor VT 05089

Windsor, VT26 Main Street

Price$875,000The price has recently decreased

MLS Number 4850881

  • Commercial
  • Year Built 1815
  • Acreage 1.1

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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.3% last updated on 2022-05-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

54 Ascutney Street Windsor VT 05089

Windsor, VT54 Ascutney Street

Price$535,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4910738

  • Multifamily
  • Bathroom 6
  • Units 6
  • Square Feet 3,560
  • Acreage 0.59

You will be impressed by how well cared for this 6 unit building is. There are 3-1 bedrooms, an efficiency and 2-2 bedroom units. The rents are in line with market rates, and you'll be able to take right over with smooth sailing. We have a 5 year old boiler, standing seam roof, vinyl siding, and vinyl windows. Get excited!

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.3% last updated on 2022-05-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

8 Union Street Windsor VT 05089

Windsor, VT8 Union Street

Price$299,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4902659

  • Multifamily
  • Square Feet 5,032
  • Units 4
  • Bathroom 4
  • Acreage 0.31

Strong Cash Flow! Profitable Investment Opportunity! This multi-family property is an excellent chance for investors to add a consistent cash flowing building to their portfolio or for an onsite owner to occupy one unit and let the extra rents pay for your housing. Located in the heart of the historic town of Windsor, VT. on a generous .31 +/- acre level lot this property is a hidden gem. Each of the main units has the possible option for 2 bedrooms, full bath, separate entrances, enclosed porches, electrical meters, hot water tanks and plenty of onsite parking. Conveniently located only minutes from I91, route 12A, shopping, grocery store, restaurants and town offices. A very easy commute to the V.A. Hospital, DHMC, Dartmouth College, Washington street in Claremont and the West Lebanon, NH. shopping malls. A great property to call home or to add to your Real Estate portfolio.

Listed by Alex DeFelice of The Clerkin Agency,P.C.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.3% last updated on 2022-05-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2781 US Route 5 North Windsor VT 05089

Windsor, VT2781 US Route 5 North

Price$245,000The price has recently decreased

MLS Number 4840641

  • Commercial
  • Year Built 1997
  • Acreage 0.48

Previously used as a McDonalds restaurant; zoned "Roadside Business", allows Professional/Business Office, Public Facility, Restaurant, Retail Store/Service, Self-Service Laundry, Veterinary Hospital, and other uses as Conditional Uses. Currently empty, was previously leased by a catering business, rent $1900/mo. NNN, monthly CAM, $700. Building has former drive-thru window, now boarded over, site appears to have room for additional parking. Located in a small shopping center with a Price Chopper, Aubuchon Hardware, and Dollar General, within walking distance of downtown historic Windsor Village, on US Route 5, close to I-91 access, ski areas, local hospital. Property lies in 100-yr. flood hazard area, AE Zone, which could trigger FEMA "50% Rule", depending on renovation/fitup plans. Elevation Certificate available.

Listed by William Johnson of Big Green Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.3% last updated on 2022-05-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

19 Weston Heights Windsor VT 05089

Windsor, VT19 Weston Heights

Price$239,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4902592

  • Residential Single Family
  • Bedrooms 3
  • Construction Existing
  • Bathroom 1
  • Square Feet 1,532

Bright and sunny cape on a level open lot in a quiet cup de sac neighborhood. Hardwood floors, first floor bedroom, kitchen with cherry cabinets. Easily accessible to I-91 and the Upper Valley.

Listed by Seth Warren of Seth Warren Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.3% last updated on 2022-05-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2227 Rt. 5 South Highway Windsor VT 05089

Windsor, VT2227 Rt. 5 South Highway

Price$235,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4910200

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,662

Very Nice well landscaped Gambrel home on .57 acre. Inside you will be pleased with the well kept, recently painted interior and period trim, doors and hardware. A large dinning room and living room with a fireplace and built in bookcase's make for great entertaining for family and friends. Upstairs you will find a very large primary bedroom as well as two more along with a full bath. Out side there is a large side yard and a large lower level area for all your recreational needs. Delayed showings until May18th and 19th. Located only 30 Mins. to all the Upper Valley has to offer and just 15 mins. to Claremont.

Listed by Richard Ballou of The Clerkin Agency,P.C.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.3% last updated on 2022-05-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

8/10 Foster Avenue Windsor VT 05089

Windsor, VT8/10 Foster Avenue

Price$234,500The price has recently decreased

Est. Mortgage: $/month

MLS Number 4903020

  • Multifamily
  • Square Feet 2,608
  • Units 2
  • Bathroom 3
  • Acreage 0.17

This is a great opportunity for investors or homeowners alike. Rent out one side and live in the other, or rent out both for a lucrative income property. Both units have an upstairs, downstairs, and their own separate basements with separate utilities. Units are very similar, with the main difference being #10 has 2 full baths, one upstairs and one down, while #8 has a half bath/ laundry downstairs and a full bath upstairs. Unit #10 has a laundry hookup in the upstairs bathroom as well as in the basement. Each unit has 3 bedrooms upstairs, a great pantry area off the kitchen, and a wide, winder staircase with spacious landings central to the apartment. A level, fenced in backyard with a shed make this a great home for pets, children, and gardening. Home is in close walking distance to food and shopping in downtown Windsor.

Listed by Chelsea Cary of Barrett & Valley Associates,Inc/Sprin

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.3% last updated on 2022-05-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

9 Bridge Street Windsor VT 05089

Windsor, VT9 Bridge Street

Price$234,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4907749

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Square Feet 1,538

Wow, what an opportunity this is! Two charming homes. The Big house, has a one car garage, covered entryway that has been modified for easy access. The three season front porch is just asking for you to sit and watch the traffic. Hardwood floors and built-ins, spacious kitchen and first floor laundry make for a great place to start a new chapter. A separate driveway provides access to the guest house. Enter through a sun filled three season porch and mudroom which leads into the kitchen. This home also has three bedrooms, a full bath, dining area, and living room! The lot is level with great opportunities for flower gardens, produce beds, or fencing off for the safety and security of your loved ones as they play.

Listed by Chelsea Bevis of KW Vermont Woodstock

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.3% last updated on 2022-05-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

9 Bridge Street Windsor VT 05089

Windsor, VT9 Bridge Street

Price$234,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4910564

  • Multifamily
  • Square Feet 2,418
  • Units 2
  • Acreage 0.15

Wow, what an opportunity this is! Two charming homes. The Big house, has a one car garage, covered entryway that has been modified for easy access. The three season front porch is just asking for you to sit and watch the traffic. Hardwood floors and built-ins, spacious kitchen and first floor laundry make for a great place to start a new chapter. A separate driveway provides access to the guest house. Enter through a sun filled three season porch and mudroom which leads into the kitchen. This home also has three bedrooms, a full bath, dining area, and living room! The lot is level with great opportunities for flower gardens, produce beds, or fencing off for the safety and security of your loved ones as they play.

Listed by Chelsea Bevis of KW Vermont Woodstock

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.3% last updated on 2022-05-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

324 Old Mill Pond Road Windsor VT 05089

Windsor, VT324 Old Mill Pond Road

Price$229,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4902382

  • Land
  • Acreage 73.9
  • Utilities None
  • Water View
  • Zoning Medium Density

Waterfront parcel with extensive development possibilities in a private yet very convenient location. The 73.9 acres are comprised of mature woodlands, open meadows, and water frontage on Old Mill Pond, linked to a private smaller pond and Mill Brook. Paths traverse the land through the lush woods and sunny meadows with lots of berries to pick along the way. The town sewer and water are in locations that make access to connections easy. Old Mill Pond Road is a private way off Lowell St. and Clough Ave. A 50 ft. right-of-way exists through Old Mill Road to the subject property. This is the perfect property to build your dream waterfront home or possibly create a multi-unit development. Easy access to the interstate and only 20 minutes to Hanover NH and the Upper Valley.

Listed by Daphne Lowe and Carol Wood of Williamson Group Sothebys Intl. Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.3% last updated on 2022-05-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

6 Hall Street Windsor VT 05089

Windsor, VT6 Hall Street

Price$205,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4907913

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,608

An ideal location in a great neighborhood. This 3 Bedroom 1 bath ranch style home located is a short walk to everything, Kennedy Pond, Recreational Fields, Schools, and all downtown amenities. This home is in great condition, custom tile backsplash in kitchen, custom cabinetry, and new flooring. The expansive living room is inviting and comfortable. As a bonus, there is a partially finished basement with additional bedroom and office space. A large storage shed with power and two floors of storage for all your toys, bikes, and gardening equipment complete this cozy and efficient home.

Listed by Seth Barbiero of Bean Group / Vermont

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.3% last updated on 2022-05-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity

Copyright 2022 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 May 19, 2022.

 

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