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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

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: 6.13% last updated on 2023-01-26

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
  • Square Feet 6,232
  • 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: 6.13% last updated on 2023-01-26

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

148 Hewett Road Windsor VT 05089

Windsor, VT148 Hewett Road

Price$420,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4931395

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,500

Nice horse property, privately sited log home on 11.4a, southern exposure, view of Mt Ascutney. Open concept kitchen, dining & living room with pellet stove; laundry & half bath on 1st level. 2 bedroom, 2 baths up. Direct entry, attached 2 car garage. Nice 3 stall horse barn with overhang, tack room, hay loft, electric & water. Small ring, open pasture, partially fenced with good dirt road access in Windsor. Consolidated Communications DSL internet @ 25 mbps.

Listed by Dana Waters and Paula Waters of Dark Horse Realty

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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: 6.13% last updated on 2023-01-26

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

77 Taylor Drive Windsor VT 05089

Windsor, VT77 Taylor Drive

Price$349,000The price has recently decreased

Est. Mortgage: $/month

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

{$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: 6.13% last updated on 2023-01-26

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

77 Taylor Drive Windsor VT 05089

Windsor, VT77 Taylor Drive

Price$349,000The price has recently decreased

Est. Mortgage: $/month

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

{$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: 6.13% last updated on 2023-01-26

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

64 Main Street Windsor VT 05089

Windsor, VT64 Main Street

Price$295,000The price has recently decreased

MLS Number 4926368

  • Commercial
  • Year Built 1920
  • Square Feet 4,569
  • Acreage 0.11

For Sale or Lease!...For Sale at $325,000...Just 3.6 miles off I-91, The Newberry Bldg is just 2 doors down from the Historic Windsor House! This 4,569 sq. ft. Retail/Office Bldg can serve one or two businesses with its 2 Store Fronts, with each side having a full basement. A "Dry Basement Solution" consisting of a curtain wall-drain system was installed on the east wall of the basement to handle potential water seepage from the front foundation, and perimeter floor drain to direct such water seepage to a sump pump in the rear of the basement. Owner says there has been no water on the basement floor during his ownership. Consequently the basement has been used for dry storage. Recent upgrades include: A recently new boiler, a new roof 12 years ago and 3 new electric service entrances. The "village lot" is roughly 57' frontage x an average of 80' deep, approximately 0.11 acre. Any business wanting to be "Front &Center" in an attractive historic Vermont Town, the oldest in Vermont, should thrive in this location! Owner will consider a Lease at $9.00/sf, NNN, with the Nets estimated at $4.00/sq. ft. However, if leased, owner prefers a Lease-Purchase whereunder tenant agrees to purchase during the Initial Lease Term.

Listed by Ray Ault of Ault Commercial Realty,Inc.

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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: 6.13% last updated on 2023-01-26

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

480 Route 5N Windsor VT 05089

Windsor, VT480 Route 5N

Price$279,000The price has recently decreased

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

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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: 6.13% last updated on 2023-01-26

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

74 Union Street Windsor VT 05089

Windsor, VT74 Union Street

Price$259,900The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4937355

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,142

Nicely maintained home in town. This home offers a main level bedroom and bath with laundry, three nice sized bedrooms upstairs, and lots of room to spread out downstairs. Easy location for walking to town for a coffee or up to the pond for a swim. Separate one car garage for storage or workshop.

Listed by Dorothy Griswold 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:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

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$239,900The price has recently decreased

MLS Number 4923750

  • Commercial
  • Year Built 1997
  • Square Feet 2,450
  • Acreage 0.48

Tremendous Business opportunity! Zoned "Roadside Business", this former McDonalds restaurant provides countless commercial options. Building is currently empty and ready for immediate occupancy, ample parking, excellent location on Route 5 just north of the Windsor Village. Minutes to I-91, and short distance to the upper valley/Dartmouth region!

Listed by Justin Ranney of Coldwell Banker Homes Unlimited

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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: 6.13% last updated on 2023-01-26

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

96 Cole Hill Road Windsor VT 05089

Windsor, VT96 Cole Hill Road

Price$225,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4926419

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • 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

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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: 6.13% last updated on 2023-01-26

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

19 Coolidge Court Windsor VT 05089

Windsor, VT19 Coolidge Court

Price$169,000The price has recently decreased

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

{$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: 6.13% last updated on 2023-01-26

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

135 Main Street Windsor VT 05089

Windsor, VT135 Main Street

Price$149,000The price has recently decreased

MLS Number 4869029

  • Commercial
  • Square Feet 1,215
  • Year Built 1952

OWNER SAYS SELL!!!! Your chance to own an iconic piece of Windsor history and continue a wonderful tradition and make it your own. This Worcester Diner Car is fully equipped and ready for new owners. With over 50 seats, there is profit to be made during breakfast, lunch and dinner if you choose. Call today to set up a tour.

Listed by Katie Ladue Gilbert 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: 6.13% last updated on 2023-01-26

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

Broker Reciprocity

Copyright 2023 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. 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 January 31, 2023 6:24 AM EST.

 

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