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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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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.11% last updated on 2021-12-02

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: 3.11% last updated on 2021-12-02

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

29 Ascutney Street Windsor VT 05089

Windsor, VT29 Ascutney Street

Price$425,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4860808

  • Multifamily
  • Units 3
  • Square Feet 3,592
  • Bathroom 3
  • Acreage 0.26

New Price! Located in the heart of Windsor-Just steps away from schools, shopping, dining, recreation and town amenities, this stately brick home was completely restored in 2013. Currently operating as a 3-unit with excellent rental history-renovation was done carefully to preserve original features, central stairway and room layout for future conversion back to a grand main home with 3-bedroom townhouse apartment in back. All units have warm wood floors, high ceilings, natural light, plentiful storage, laundry and updated kitchens and baths. Completely updated systems including all electric service, plumbing, heating, hot water and extensive closed cell foam insulation in basement and ceilings. A rare opportunity to own a lovely, updated home in a great community whether you are looking for investment property or a primary home with income from one or two units to help with a mortgage. In-town living close to abundant outdoor recreation-Mill Pond, Lake Runnemeade, CT River, Ascutney Outdoors, Saint Gaudens National Park and so much more. Convenient to I-91 for access to Upper Valley and beyond. Just 20 minutes from Dartmouth College and Hanover, NH and under 30 minutes from Dartmouth Hitchcock Medical Center and Lebanon, NH.!!!

Listed by Tambrey Vutech 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: 3.11% last updated on 2021-12-02

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

29 Ascutney Street Windsor VT 05089

Windsor, VT29 Ascutney Street

Price$425,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4860908

  • Residential Single Family
  • Square Feet 3,592
  • Bedrooms 8
  • Construction Existing
  • Bathroom 3

New Price! Located in the heart of Windsor-Just steps away from schools, shopping, dining, recreation and town amenities, and 20 minutes from Dartmouth College/Hanover NH and less than 30 minutes from DHMC Lebanon, NH-this stately brick home was completely restored in 2013. Although it is currently operating as a 3-unit with excellent rental history-the extensive and thoughtful renovation was done carefully to preserve original features, central stairway and room layout for future conversion back to the grand primary home with 3-bedroom townhouse apartment if desired. All units have warm wood floors, high ceilings, natural light, plentiful storage, laundry and updated kitchens and baths. Completely updated systems including all electric service, plumbing, heating, hot water and extensive closed cell foam insulation in basement and ceilings. A rare opportunity to own a lovely, updated home in a great community- whether you are looking for investment property or a primary home with income from one or two units to help with a mortgage or space for guests-the options are many! In-town living close to abundant outdoor recreation-Mill Pond, Lake Runnemeade, CT River, Ascutney Outdoors, Saint Gaudens National Park and so much more. Convenient to I-91 for access to Upper Valley and beyond. Note that .26 Ac conveys and current tax bill reflects .61 Ac Lot.

Listed by Tambrey Vutech 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: 3.11% last updated on 2021-12-02

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 4848316

  • Commercial
  • Year Built 1920
  • Acreage 0.11

For Sale or Lease!...For Sale at $295,000...The Newbury Bldg was occupied by a popular retail business by that name in the 1950's and 60's. Just 2 doors down from the Historic Windsor House, this 4,400 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 states that During his ownership there has been no water on the basement floor. Consequently the basement floor has been used for dry storage. Recent upgrades include: A new boiler, a 10-year new roof 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! (See ML#4848319 for the Listing For Lease).

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: 3.11% last updated on 2021-12-02

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

131 Main Street Windsor VT 05089

Windsor, VT131 Main Street

Price$275,000The price has recently decreased

MLS Number 4853436

  • Commercial
  • Acreage 0.2

Remodeled Mixed Use Income Property: Restaurant/Retail on main floor, 2 residential apartments up, and storage rental to single tenant in basement. Total of 4 rental units in bldg. Gross Income $36,600 Annually. Parking in rear of bldg, via right of way over parcel north of subject. Roof is "Built-up", new in 2007, repaired in 2019. Restaurant has new grease trap in 2020.

Listed by Ray Ault of Ault Commercial Realty,Inc.

{$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: 3.11% last updated on 2021-12-02

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$265,000The price has recently decreased

MLS Number 4840641

  • Commercial
  • Year Built 1997
  • Acreage 0.48

Perfect for a drive-thru, take-out, delivery, catering type restaurant, consistent with current needs, this property was formerly a McDonald's, is currently empty, was previously leased by a catering business, rent $1900/mo. NNN, monthly CAM, $700. Building has drive-thru window, probably not enough parking for sit-down restaurant. 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. Zoned "Roadside Business", usage may be limited to restaurant/food business as a grandfathered non-conforming usage, or, another "Permitted Use" under the Windsor Zoning Regulations (see supporting documents)--"Restaurant" usage is a "Conditional Use" under the Regulations, which would require more acreage than exists here, as would other "Conditional Uses". Survey states property lies in 100-yr. flood hazard area, AE Zone. 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: 3.11% last updated on 2021-12-02

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

4 Meadow Lane Windsor VT 05089

Windsor, VT4 Meadow Lane

Price$244,900The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4888099

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,072

This split level home just up above the village of Windsor is ready for new love. You'll be pleased to find hardwood floors, an attached garage, plenty of storage, and very little lawn or driveway to maintain. The kitchen and baths can be updated to your own taste, on your timeline. The deck off of the dining room, with new slider, leads you to a private backyard oasis, extending your entertainment space. 3 bedrooms on the main level, with one more potential on the lower level, gives you endless sleeping spaces. Warm up by one of 2 fireplaces in the home.

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: 3.11% last updated on 2021-12-02

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

37 River Street Windsor VT 05089

Windsor, VT37 River Street

Price$207,500The price has recently decreased

MLS Number 4853438

  • Commercial
  • Acreage 0.22

4-Unit Apartment House plus 6 garage rental spaces generate Annual Gross Rents of $38,880. Ample on-site parking. Less than 2-block walk from downtown banks, restaurants and other businesses.

Listed by Ray Ault of Ault Commercial Realty,Inc.

{$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: 3.11% last updated on 2021-12-02

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

43 River Street Windsor VT 05089

Windsor, VT43 River Street

Price$207,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4888098

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,116

Come see the beauty of hardwood floors, wide trim, built-ins, and high ceilings. From the moment you walk in, you are welcomed by the grand size of the rooms. You can easily see life happening within these walls. The enclosed three season porch is asking for gatherings or just a quiet drink and relaxation. The extra unfinished space off the main house is awaiting your vision and needs. Laundry hookups on the second floor conveniently join the three bedrooms and full bath. The attic space is sure to "Wow" you at the stairs. Many great upgrades made since 2014, including new boiler, hot water heater and roof. Two large outbuildings are ready for all your things, and so much more to appreciate about this property.

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: 3.11% last updated on 2021-12-02

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

70 Main Street Windsor VT 05089

Windsor, VT70 Main Street

Price$195,900The price has recently decreased

MLS Number 4853428

  • Commercial
  • Year Built 1850
  • Acreage 0.05

Great downtown Historic Building, with a 2,046 sq. ft. main floor Restaurant. Current building owner invested over $150,000 in improvements in 2006, including all new electric wiring and panels, asbestos removed and certified, handicapped toilet facilities installed, office space in basement, new attic stairs, a new roof and new front awning. Additionally, a new propane furnace was installed in 2014. While there is 2,926 sq. ft. above grade, the 880 sq. ft. 2nd floor needs some renovation to bring into use. Currently leased to a new restaurant business, this property has been upgraded to yield a good income in a prime location.

Listed by Ray Ault of Ault Commercial Realty,Inc.

{$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: 3.11% last updated on 2021-12-02

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$195,000The price has recently decreased

MLS Number 4869029

  • Commercial
  • Year Built 1952

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: 3.11% last updated on 2021-12-02

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

Broker Reciprocity

Copyright 2021 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 6, 2021.

 

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