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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. ​Register 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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1185 Route 5 South Windsor VT 05089

Windsor, VT1185 Route 5 South

Price$625,000The 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

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.79% last updated on 2024-11-07

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

26 Depot Street Windsor VT 05089

Windsor, VT26 Depot Street

Price$550,000The price has recently decreased

MLS Number 4946823

  • Commercial
  • Year Built 1900
  • Square Feet 2,888
  • Acreage 0.31
  • PricePerSqFt 190.44

Historic Masterpiece built in 1900. Windsor Station remained an active train station until the mid-sixties when the building was shuttered. In the mid-1970's a team leased the building from Central Vermont Railway and converted it into a restaurant. The restaurant changed hands in 1976 and was successfully run by the same family for 35 years. After changing hands again, the building was then abandoned in October of 2010. In April 2013 the current owner/operators rescued the then derelict property and made extensive renovations and added period decorations. Along with providing excellent food and service, they have turned the property into a thriving and successful operation. Amtrak service continues with the newly built platform alongside the building. The “Vermonter Train” runs from Washington D.C. to St. Albans-Burlington, VT passing through Baltimore, NYC, Philadelphia along the way. The Southbound train stops at Windsor Station around noon and the Northbound stops around 6pm to the delight of the diners. Step inside this epic station and it will take you back to a different era. Windsor Station Restaurant is the pulse of the Town. Excellent growth potential with lunch and brunch services. Currently in construction is a beautiful 4 acre park across the tracks and a 35 unit apt building up the street. Buyers will be asked to fill out a Prospect Package before receiving the financials. Numbers support the price. Owners are only interested in talking with Qualified Buyers.

Listed by Dick Palmer of Hospitality Consultants,LLC

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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: 6.79% last updated on 2024-11-07

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$500,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

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: 6.79% last updated on 2024-11-07

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

30 Union Street Windsor VT 05089

Windsor, VT30 Union Street

Price$430,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5018205

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

Step into timeless elegance with this grand Victorian home, beautifully situated on a charming in-town lot. This stately residence showcases stunning hardwood floors throughout, preserving its classic heritage while offering modern comforts. The spacious first-floor bedroom features an en suite bath, providing both luxury and convenience. A cozy fireplace adds warmth and character to the main living space, perfect for relaxing evenings. The home boasts a generously-sized walk-in pantry, ideal for storage and organization. An added bonus is the potential separate apartment, offering endless possibilities for rental income, guest accommodations, or an in-law suite. Completing the property is a two-car detached garage, providing ample storage and parking. This house will suit a buyer who hopes to fill it's halls, expand, or be a welcome haven for a family compound. Minutes into downtown Windsor, an easy jaunt to the K-12 school, and a stones throw away from the Recreation Center makes for flexibility if transportation is an issue. Come make this one your own!

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: 6.79% last updated on 2024-11-07

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

12 Fairview Street Windsor VT 05089

Windsor, VT12 Fairview Street

Price$430,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5020640

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

Prepare to be captivated by this picturesque 3-bedroom, 2-bath farmhouse, perfectly situated near Mill Pond and adjacent to the Windsor Fairgrounds. This enchanting home radiates charm and character, featuring stunning wood flooring and unique finishes that highlight its timeless appeal. The open floor plan seamlessly connects the Kitchen and Dining area, complete with a convenient island, leading to a spacious family room adorned with beautiful built-in cabinets-ideal for both relaxation and entertaining. Retreat to the cozy den, tucked behind elegant French doors, where a wood stove creates a warm atmosphere, or unwind in the sunroom that offers breathtaking views of the lush perennials surrounding the property. Upstairs, you'll find three generously sized bedrooms, including a massive primary suite with his and her closets, ensuring plenty of space for comfort and storage. Outside, the property boasts a charming red barn and a practical storage shed, providing ample room for all your projects and hobbies. Experience the perfect blend of country living and modern amenities in this delightful home. Don't miss your chance to make it your own!

Listed by Livian Vermont and Daniel Preston of KW 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:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.79% last updated on 2024-11-07

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$369,000The 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 4th sleeping space with a 3/4 bath and kitchenette space. For those seeking easy living, this move-in ready unit within an impeccably maintained condo association is hard to beat!

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: 6.79% last updated on 2024-11-07

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

30 Estey Lane Windsor VT 05089

Windsor, VT30 Estey Lane

Price$350,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5019666

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3

Welcome to your dream home! Nestled on 14 sun-kissed acres, this spacious 4-bedroom, 3-bathroom property offers an idyllic blend of privacy and convenience. Enjoy breathtaking countryside views from every angle, with plenty of space to roam and relax in a serene, natural setting. And bonus, there are trails, a cider house, and plenty of room for a garage or workshop space. Inside, you'll find a well-appointed layout that includes a bright and inviting living room with new woodstove, a bedroom on the main level, 2 expansive bedrooms on the 2nd level with full bathroom, and space for guests or in-laws in the finished basement. The basement has 2nd kitchen, 3/4 bathroom and sleeping spaces with private entrance. Located just minutes from I-91, you'll have easy access to the Upper Valley, while being less than 4 miles from the charming, historic town of Windsor, and a hops, skip, and a jump from West Windsor. This is more than a home-it's a peaceful retreat with modern convenience. Don't miss your chance to experience country living at its finest!

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: 6.79% last updated on 2024-11-07

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

69 Morningside Drive Windsor VT 05089

Windsor, VT69 Morningside Drive

Price$285,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5011948

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

Don't scroll past this listing without flipping through all the pictures! This turn-key 1988 ranch with a full concrete basement and attached garage in a quiet cul-de-sac neighborhood located in Windsor, Vermont is calling your name! Move right in with ease as the property is available now. Live comfortably on the main level with three bedrooms and two full bathrooms, plus the downstairs has high ceilings and represents a lot of potential future finished living space, if you need room to grow. Brand new appliances in the kitchen still have the tags on them. The private back deck leads to a side entrance to the garage and through to the basement, which conveniently connects back up to the main level. Primary suite with private bathroom. Plenty of parking for your guests. Recent upgrades include new bathroom vanities, toilets, flooring and fresh paint. Close to Interstate 91 and 15 minute commute to White River and West Lebanon where you can run errands. Easy access to the highway to zip down to Boston and New York City. Dartmouth Hitchcock Hospital with a trauma center is within 30 minutes. Close to many dining options, retail shopping, outdoor adventures on the Connecticut River, a historic downtown area, colleges, airports, breweries, distilleries, dispensaries, country clubs, golf courses, Mt. Ascutney, and all the things! Don't delay, set up a viewing today.

Listed by Krista Harness of Green Light 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: 6.79% last updated on 2024-11-07

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

10 Mckenzie Drive Windsor VT 05089

Windsor, VT10 Mckenzie Drive

Price$269,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5014358

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

Step into the timeless charm of this well-maintained 1920s single-family home, nestled in the heart of Olde Windsor. As you enter through the welcoming front patio, you're greeted by a classic entryway that leads seamlessly into a cozy living room, perfect for relaxing or entertaining. There are beautiful hardwood floors in both the entryway and the dining room, creating a warm and inviting atmosphere. Continue through the living room into the dining area to discover a well-appointed kitchen. Conveniently located on the main floor, a half bath features an integrated washer and dryer for added functionality. Just off the dining room, step out onto the back patio, where you'll enjoy serene views of the expansive backyard-an excellent space for outdoor activities and summer barbecues. Venture upstairs to find three generously sized bedrooms and a full bath. Located centrally between Mill Pond, Lake Runnenede, and the Connecticut River, this residence offers a perfect blend of tranquility and accessibility. Enjoy a short 15-minute stroll to Main Street, where a vibrant array of local restaurants awaits. This home is a rare find, combining vintage charm with modern convenience in a sought-after neighborhood. Don't miss the opportunity to make this enchanting property your own!

Listed by Livian Vermont and Chelsea Bevis of KW 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:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.79% last updated on 2024-11-07

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

12-14 State Street Windsor VT 05089

Windsor, VT12-14 State Street

Price$265,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4999035

  • Multifamily
  • Units 4
  • Acreage 0.03
  • Square Feet 2,430
  • PricePerSqFt 109.05

Rare Opportunity in the heart of Windsor, Vermont. This building contains 3 residential rental units and 1 additional unit that has been used as office space but can be converted into an additional residential unit with a permit. This originally balloon built property has had its foundation restabilized, new insulation, and almost 100% siding replaced. The first floor contains the office rental, Unit 1, Unit 2 access, and a common area/mailroom. Unit 1 contains a mudroom, kitchen/living room, bedroom, and bathroom. Unit 2, on the second floor, contains a kitchen, living room, bathroom, and two bedrooms. Unit 2 has high ceilings making the space feel open and spacious, with upgraded electrical throughout most of the building. Unit 3 is accessed by covered outdoor stairs to the third floor. This unit contains a small mudroom, kitchen/dining room, bathroom, and two bedrooms. Office space is currently an open office room with a private bathroom. Basement is dry and spacious, plenty of space for storage and/or laundry room. Seller has Lead Paint Certification. The location is right downtown! Café across the street and walking distance to shops, parking, laundry mat, school, and public transportation. Delayed showings until Thursday June 13th!

Listed by Cheryl Herrmann and Kelsey Herrmann-Satnzel of RE/MAX Group One Realtors

{$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: 6.79% last updated on 2024-11-07

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

54 Hillside Drive Windsor VT 05089

Windsor, VT54 Hillside Drive

Price$255,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5019305

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

Nestled just off the main road, this charming split-level home offers the perfect blend of privacy and convenience. Located just moments from town, you'll enjoy the peaceful setting without sacrificing easy access to local amenities. The inviting living room features a large picture window, filling the space with natural light. The adjacent kitchen includes a cozy dining area, ideal for family meals. Just a few steps up, you'll find three comfortably sized bedrooms and a full bath. The partially finished basement presents an excellent opportunity for a future rec room, home office, or gym. Outdoors, the home boasts spacious front and side yards, perfect for gardening, entertaining, or simply relaxing in your own serene environment. Whether you're starting a new chapter or looking to expand, this home offers the potential to customize and make it your own. Don't miss out on this perfect blend of privacy and proximity!

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: 6.79% last updated on 2024-11-07

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

242 Huntington Drive Windsor VT 05089

Windsor, VT242 Huntington Drive

Price$249,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5020575

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

Welcome home to this inviting 3-bedroom, 1-bath ranch-style gem nestled in one of Windsor's most sought-after neighborhoods. Step inside to find a cozy living room with a beautiful fireplace, perfect for New England winters. The kitchen opens into the dining room, and could be your chance at a fun remodel. Each bedroom provides comfort and plenty of natural light, making it a warm retreat for family or guests. Outside, enjoy a private backyard and convenient 1-car garage with extra storage. Located close to local amenities, parks, and schools, this home offers both tranquility and convenience. With its prime Windsor location, this property won't last long-schedule your showing today!

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: 6.79% last updated on 2024-11-07

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 November 11, 2024 1:12 PM EST

 

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