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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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2768 Hunt Road Windsor VT 05089

Windsor, VT2768 Hunt Road

Price$1,450,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5001669

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3

Fox Penny Farm, an established horse farm on 62 acres of open fields, trails, and woods on the Windsor/West Windsor line with westerly views of Mt Ascutney, is now offered for sale. Offering an expansive 3-bedroom 2.5 baths colonial with light-filled spaces, hardwood floors, spacious kitchen, dining room & propane fireplaced living room. Upstairs provides three large bedrooms with a primary ensuite. The lower level offers a partially finished living area with a wood stove and French doors leading to a private deck. Complete with 36x50 5-stall barn, 1000 bale hay storage heated tack room, and wash stall. Multiple run-in sheds, fenced paddocks, 100' x 200 outdoor arena, equipment shed, and workshop with woodstove, all on open flat land. Fully wired generator servicing the house, barn, and outbuildings. Easily adaptable for farming pursuits. Prime location for hiking, biking, and skiing. Easily accessible to Woodstock & the Upper Valley. A special property that must be seen to appreciate all the possibilities.

Listed by Scott Monahan and Danny Kogut of Williamson Group Sothebys Intl. Realty

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

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.89% last updated on 2024-07-11

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

3223 County Road Windsor VT 05089

Windsor, VT3223 County Road

Price$879,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 5001343

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2

Welcome to this exquisite four-bedroom, two-bathroom Colonial home, built in 1801, nestled on a sprawling 10.4-acre lot in Windsor, Vermont. This charming residence boasts maple and bamboo floors as well as original wide pine flooring, spacious bedrooms, and tiled bathrooms. The property includes a two-bedroom, one-bathroom ADU, perfect for generating rental income or accommodating guests. Enjoy the serene rural setting with level land ideal for animals, fenced pastures, and extensive perennial gardens. Outdoor amenities include a glamping site over the barn, RV hookups, an in-ground pool, and a tranquil majestic pond surround by natural iris that bloom every spring. Recent updates blend historic charm with modern appointments, maintaining the home beautifully for 30 years under the same owner. Located close to local amenities, this home offers both seclusion and convenience. Additional features include outbuildings and an animal barn, providing ample storage and versatile use. Don't miss this unique opportunity to own a piece of Vermont history with endless potential.

Listed by Kate Cassidy of Four Seasons Sotheby's Int'l Realty

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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: 6.89% last updated on 2024-07-11

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

1185 Route 5 South Windsor VT 05089

Windsor, VT1185 Route 5 South

Price$675,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4990468

  • Multifamily
  • Units 8
  • Acreage 1.44
  • Square Feet 2,768
  • Utilities None

Introducing a prime investment opportunity nestled on 1.44 acres of picturesque countryside just moments away from the convenience of town living. Whether you're a seasoned investor seeking a lucrative addition to your portfolio or a newcomer to the world of real estate investment, this 8-unit property presents an attractive proposition. With its idyllic location, modern updates, and reliable tenant base, it offers the perfect combination of rural charm and urban convenience-a truly rare find in today's market. Don't miss your chance to own a piece of country paradise with endless potential for growth and prosperity.

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: 6.89% last updated on 2024-07-11

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

25 Main Street Windsor VT 05089

Windsor, VT25 Main Street

Price$550,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4998054

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2

Built in 1796, the historic Trask House is located on beautiful Main St. in the heart of downtown Windsor. The center hall Federal sits on just under 1/2 acre and has an attached barn/garage in the back with plenty of storage. There is a private brick patio surrounded by a white picket fence and lovely landscaping. Inside, you are greeted by large open rooms with hardwood floors, high ceilings, and multiple fireplaces. The updated kitchen is open to the dining room with a wood burning stove centered between the two rooms. The dining room leads to the stunning living room with picturesque alcoves and original Federal style millwork and mantels. Across the hall are the family room and a quaint library which ultimately connects back to the kitchen. A grand center hall stair case leads upstairs to 4 good sized bedrooms, a full bath and the laundry room. The Trask House is in an ideal location just minutes from Lake Runnemede, restaurants and stores, and Mt. Ascutney Hospital. Woodstock, Hanover, and the Upper Valley are approximately 25 minutes away. The Trask House is in the National Registry of Historic Homes and has been featured in numerous books on historic homes of New England. Come take a look!

Listed by Dan Noble of Snyder Donegan 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:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.89% last updated on 2024-07-11

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

37 Morningside Drive Windsor VT 05089

Windsor, VT37 Morningside Drive

Price$445,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5001571

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

Discover your dream home nestled in a serene neighborhood! This charming 3-bedroom Cape Cod-style house sits on a spacious 1.15-acre lot adorned with delightful perennial gardens. Step inside to experience a cozy, yet spacious interior that seamlessly blends classic charm with modern comfort. The home features a thoughtfully designed layout, ideal for both relaxation and entertaining. Enjoy gatherings in the generous living areas, enclosed porch and expansive deck or retreat to the tranquil bedrooms for peace and quiet, complete with endless closet space. Convenience meets lifestyle with a one-car garage providing ample storage and parking space. Located just minutes from I-91, commuting is a breeze, while easy access to town amenities ensures you're never far from shopping, dining, and entertainment options. Don't miss your chance to own this exceptional property in a sought-after neighborhood. Schedule your private tour today and envision the possibilities of calling this house your new 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: 6.89% last updated on 2024-07-11

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

39 Huntington Drive Windsor VT 05089

Windsor, VT39 Huntington Drive

Price$399,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 4999516

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1

Welcome to this well-maintained ranch located in the highly sought-after Juniper Terrace neighborhood. This delightful home features 3 cozy bedrooms and 1 full bath, perfect for comfortable living. The inviting living area is complemented by a pellet stove, providing warmth and ambiance during the cooler months. The highlight of this home is the finished basement, offering additional living space that can be customized to suit your needs-be it a family room, home office, or recreation area. The exterior is equally impressive with a well-manicured lawn and charming curb appeal. Don't miss the opportunity to make this lovely home yours. Schedule a showing today and experience the best of Juniper Terrace living! Open House Sunday June 23, 10-12noon

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:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.89% last updated on 2024-07-11

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

2326 Route 5 N Windsor VT 05089

Windsor, VT2326 Route 5 N

Price$399,000The price has recently decreased

MLS Number 5003219

  • Commercial
  • Year Built 1900
  • Square Feet 3,427
  • Acreage 0.81
  • PricePerSqFt 116.43

This long standing Windsor staple has been the local Vet and Pet Dental for many, many years. Retirement looms for these owners, lending a vast opportunity for someone new. Consider having a wonderful commercial space complete with offices or exam rooms, plenty of parking, waiting areas, several entrances, and updated systems: roof, electrical, siding, heating, etc.. Further, you have 3 tenants paying the majority of the mortgage before even utilizing the main level for further investment or rental. Call today to discuss the endless possibilities.

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: 6.89% last updated on 2024-07-11

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

4 Old Mill Pond Road Windsor VT 05089

Windsor, VT4 Old Mill Pond Road, Unit 4

Price$390,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5000223

  • Condo
  • Square Feet 2,052
  • Bedrooms 3
  • New Contruction Existing
  • Complex Old Mill Pond

Old Mill Pond Condominiums offer an idyllic haven in the heart of Windsor. Imagine enjoying mountain views, pond access, and amenities such as an in-ground pool and tennis courts. This unit features vaulted ceilings and unique architectural elements often missing in typical condominiums. Guests can relax by the cozy fireplace or on the spacious deck with mountain views, depending on the season. Year-round convenience is assured with an attached garage, ample storage, and a functional layout. The unit includes three bedrooms, each with an ensuite bath-one of which includes a delightful jacuzzi tub. Includes an additional inviting 4th sleeping space to accommodate your guests. For those seeking easy living, this move-in ready unit within an impeccably maintained condo association is hard to beat! **delayed showings until Open House Sunday June 16th, 2024**

Listed by Julie Davis 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: 6.89% last updated on 2024-07-11

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

119 Ascutney Street Windsor VT 05089

Windsor, VT119 Ascutney Street

Price$275,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5000569

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2

OPEN HOUSE Saturday, June 15th 10-12 PM! Nestled on the edge of Windsor Village, this charming cape-style home has a well-maintained allure and picturesque appeal, inviting new homeowners to make it their own. A cobblestone chimney accents the exterior and a welcoming split rail fence adds to its quaint charm. Many new upgrades and features include a circular driveway, all new vinyl siding, new windows, and a private back patio deck. The driveway offers easy access to pull in & out, and ample parking space as well. The mudroom seamlessly connects to the kitchen, convenient for unloading your groceries, and unwind in the spacious and open concept living/dining room filled with natural light through large bay windows. Enjoy hardwood floors throughout and a classic stone fireplace could be revived for cozy evenings by the fire. The functional eat-in kitchen offers extra counter space, while a bonus room provides versatility as a den or office area. A front and back staircase ascend to four large bedrooms on the second floor, ensuring plenty of space for everyone. Outside, a large flat yard invites creativity, perfect for creating your ideal outdoor oasis, whether it's building a firepit for gatherings, playing or gardening. Walk to school, the Windsor Swim Area at Mill Pond, or explore the Windsor Fairgrounds and Paradise Park. With a short commute to Hanover, Lebanon, DHMC, and Dartmouth College, this move-in ready home offers great accessibility in one desirable package.

Listed by Tyler Hall of BHHS Verani Upper Valley

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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: 6.89% last updated on 2024-07-11

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

9 Durkee Street Windsor VT 05089

Windsor, VT9 Durkee Street

Price$199,900The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4995187

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 12
  • Bathroom 3

Let this rooming house be your next great investment. 10 rooms, and a 2 bedroom apartment. Some long term renters. Rooms still available, and new boiler just installed.

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: 6.89% last updated on 2024-07-11

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

70-74 State Street Windsor VT 05089

Windsor, VT70-74 State Street

Price$195,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4953869

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4

The Stephen Jacob House is an extremely important historic residence in a town known for its historic architecture. Built in 1784 in the Georgian/Federal style, the residence was sited on the rise of State Street from the Village of Windsor. It's commanding presence was embellished with cornice dentil detailing and possibly a Palladian window. Having been used for many purposes over the years, the house was purchased by Historic Windsor, Inc. in 2008. Recognizing its historic significance along with much original fabric intact, Historic Windsor, Inc. engaged in a massive cleanup, extensive documentation and a complete paint job with some sections reroofed with standing seam. The residence is now ready for the next phase of its life as a single family residence, up to 4 residential apartments, owner occupied business or a cultural center. All of the necessary as built architectural plans, documentation of existing materials and fabric and proposed Feasibility Plans are available. The project will require all new systems and rehab working with the extensive original fabric including interior shutters, period flooring and window and door detailing. Many original doors. The residences rich history with Stephen Jacob and its architectural significance will regain its prominence in Historic Windsor upon completion.

Listed by Wade Treadway of Wade I Treadway 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: 6.89% last updated on 2024-07-11

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

92 State Street Windsor VT 05089

Windsor, VT92 State Street

Price$189,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 5002505

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 6
  • Bathroom 2

Amazing opportunity to easily convert this 6 bedroom duplex into a single family home! Or, have a perfect in-law apartment. Great location across the street from Windsor High School and backing to Lake Runnemede! The yard has mature shade trees. With a little clearing, you may be able to have views of Lake Runnemede which is just down the hill from the house. There is a narrow strip of park land between the house and the lake. This home has strong bones, feels solid, and has level flooring which is rare for homes of this age. It is a tremendous value with so much potential - it just needs some cosmetic work to bring it up to date. There are hardwood floors under all carpeting with the exception of the 17' bedroom over the garage which is an addition. Deeded access to shared driveway. Downtown shops and restaurants are just a short .3 mile walk on sidewalks. Convenient location just 20 miles to both Lebanon and Hanover, NH. Mt. Ascutney Hospital is less than a mile. Nature enthusiasts will love easy access to the 5 miles of trails at Paradise Park just a half mile away. Neighboring Lake Runnemede is a birding hotspot with over 215 species of birds sighted and beautiful Mill Pond is just 1 mile. So many amenities for such a low price!

Listed by Lisa Friedman of Great American Dream 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:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.89% last updated on 2024-07-11

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

Broker Reciprocity 

Copyright 2024 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 July 15, 2024 5:53 PM EDT

 

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