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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
  • Bathroom 9
  • Construction Existing
  • Bedrooms 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: 6.29% last updated on 2022-09-22

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
  • Square Feet 6,232
  • 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: 6.29% last updated on 2022-09-22

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

3039 Route 44 Windsor VT 05089

Windsor, VT3039 Route 44

Price$485,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4926625

  • Residential Single Family
  • Construction Existing
  • Square Feet 1,398
  • Bedrooms 2
  • Bathroom 2

MNT ASCUTNEY VACATION GETAWAY! Meticulously designed & constructed contemporary sited directly on the Mountain with beautiful private views of the Vermont countryside. This home comes fully furnished and has direct access to hiking & biking and is ready for your immediate enjoyment as a second home & will be an ideal Airbnb rental. There is a great open floor plan with cathedral ceilings, tons of natural light, & pine floors throughout. The sliding glass doors open to a covered, wrap around porch & stone patio/firepit with plenty of space for entertaining, dining, and watching the sun set. The entryway mudroom has generous built-in storage with laundry and the kitchen boasts beautiful soapstone counters, self-closing drawers, and luxury Italian stainless steel gas range and dishwasher. The living room/dining room has a mounted TV and custom gas Jotul fireplace perfect for cold winter nights. The elegant first level bathroom has a huge walk-in rainfall shower with slate tiles & teak mats. There is a first level bedroom that accommodates 2 bunkbeds and the second level hosts a private master suite with walk-in closet/dressing room, 3/4 bath, & balcony. The large basement has a wide interior staircase access for easy expansion and the home is equipped with whole house air conditioning and heat pump technology. This home is a perfect getaway with Mt. Ascutney State Park & Ascutney Outdoors Center offering access to outdoor recreation year-round and is a short drive to Woodstock.

Listed by John Bassette of Bassette Real Estate Group

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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: 6.29% last updated on 2022-09-22

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$449,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4931395

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

Well kept, privately sited log home on 11.4a, 2 bedroom 2 bath with 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: 6.29% last updated on 2022-09-22

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

38 Ascutney Street Windsor VT 05089

Windsor, VT38 Ascutney Street

Price$439,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4923435

  • Residential Single Family
  • Bedrooms 5
  • Square Feet 3,040
  • Bathroom 3
  • Construction Existing

Price Just Reduced, don't wait! There is always a home in every small town that everyone would love to tour. Windsor has a few gems, and this home at 38 Ascutney St. is one of them. This garden oasis, with charming wrap around porch complete with screened in sitting area and rocking chairs will be a home you cannot miss seeing. Drive in the tree and flower lined driveway to find a backyard that you never knew existed, bursting with fruit trees, and blueberry bushes, even irrigation. The pool may be closing soon for the season, but you can stargaze by the firepit. Plenty of parking with a detached 2 car garage and paved driveway. It's time to stroll through this exquisite home. First stop is the entry way with built in storage, then on to the kitchen with custom concrete countertops and plenty of space to entertain as the room leads into the gorgeous sunroom. The main level finishes off with a formal dining and living room and 3/4 bath. On the 2nd level, there are endless bedroom options, laundry and even a den. There is an attic bedroom with 1/2 bath. The home boasts the 19th century charm(think pocket doors and built ins), with modern updates (windows and newer roof on much of the home).

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: 6.29% last updated on 2022-09-22

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$359,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4931491

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

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

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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: 6.29% last updated on 2022-09-22

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

60 State Street Windsor VT 05089

Windsor, VT60 State Street

Price$349,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4924324

  • Multifamily
  • Units 4
  • Square Feet 3,361
  • Bathroom 4
  • Acreage 0.23

Excellent opportunity to purchase an investment property with strong rental history and consistent cash flow. Four spacious units with many recent updates. The ideal location is on a tree-lined street and easy walking to local restaurants, shopping and schools. Financials available upon request. 48 hour notice needed for all showings.

Listed by Holly Hall of Snyder Donegan Real Estate 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:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

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$325,000The price has recently decreased

MLS Number 4926368

  • Commercial
  • Square Feet 4,569
  • Year Built 1920
  • 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.

{$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: 6.29% last updated on 2022-09-22

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

5 Old Mill Pond Road Windsor VT 05089

Windsor, VT5 Old Mill Pond Road, Unit 5

Price$280,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4929032

  • Condo
  • New Contruction Existing
  • Complex Old Mill Pond Condos
  • Year Built 1989
  • Square Feet 2,145

Old Mill Pond Condominiums are an idyllic haven right in the heart of Windsor. Imagine having mountain views, pond access, and the use of an in-ground pool and tennis courts, all within walking distance of downtown Windsor. The units here have vaulted ceilings and the architectural interest that so many condominiums lack. This particular unit has an open kitchen with a large island that makes entertaining a pleasure. You and your guests can enjoy the cozy fireplace or the spacious deck with mountain views, depending on the season. But you'll appreciate the convenience of the attached garage, plentiful storage, and functional layout all year round. With three bedrooms, each with an ensuite bath plus a half bath to spare, there is plenty of room for all. If you are looking for easy living, this move-in ready unit within an impeccably maintained condo association is hard to beat! Showings will be by appointment, starting on Sunday, September 11th, 2022.

Listed by Heidi Ruth of Coldwell Banker LIFESTYLES - Hanover

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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: 6.29% last updated on 2022-09-22

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

82 State Street Windsor VT 05089

Windsor, VT82 State Street

Price$249,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4924323

  • Multifamily
  • Units 3
  • Bathroom 3
  • Square Feet 2,353
  • Acreage 0.23

Unique opportunity to own a turnkey investment property with strong rental history. Three spacious units with many recent upgrades. Large deck overlooking local pond in a lovely residential area. Ample storage and garage space plus walking distance to all that Windsor has to offer. Financials available upon request. 48 hour notice required for all showings.

Listed by Holly Hall of Snyder Donegan Real Estate 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:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

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
  • Square Feet 2,450
  • Year Built 1997
  • 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

{$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: 6.29% last updated on 2022-09-22

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

7 Fairview Avenue Windsor VT 05089

Windsor, VT7 Fairview Avenue

Price$239,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4924840

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,984
  • Construction Existing

This well maintained cape has so much to offer. Inside you'll find 3 bedrooms on the same floor and a large den on the main level, functional kitchen, formal dining room and a large pantry or storage area. With 2 three season porches the home provides tons of space. Located on a spacious level lot, walking distance to recreation areas and a short distance from downtown Windsor. Showings begin Friday 8/12 from 10:00-12:00, Saturday 8/13 10:00-12:00 and Sunday 8/14 from 12:00-2:00.

Listed by Wendie Wright of Coldwell Banker LIFESTYLES - Hanover

{$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: 6.29% last updated on 2022-09-22

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 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 September 29, 2022 3:53 AM EDT.

 

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