$326,641Average Value$212Average Price per Sq Ft8Homes For Sale
History and an outdoor lifestyle in Windsor, Vermont
Located in the shadow of Mount Ascutney and on the banks of the Connecticut River, which separates Vermont from New Hampshire, Windsor is a township of about 3,500 residents as of the 2020 census. Known as the “birthplace of Vermont,” it's where the Constitution of the Vermont Republic was signed in 1777; Vermont would become a U.S. state in 1791. Windsor remained the state capital until 1805. Now, the area is known for for a mix of outdoor recreation opportunities, shops and restaurants in its small downtown area — and for a unique fall festival. Starting in 2020, Windsor and surrounding townships saw an influx of younger residents who moved to the area during the COVID-19 pandemic to work remotely. “It’s a very doable lifestyle for a lot of people,” says Danny Kogut, an associate broker with Williamson Group Sotheby’s International Realty who has 15 years of local real estate experience. “That’s what we’re seeing lately, in the years since COVID.”
History is around every corner in the city of Windsor.
Golfers of Windsor tee it high and let it fly at John P. Larkin Country Club.
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Varied styles, older builds and expansive country lots
Homes in and around the small downtown can cost between $110,000 and $430,000, depending on size, age and level of restoration needed. Some homes in this central area date from the late 1700s or mid-1800s, while others were built in the 1930s through the 1950s. Cape Cods and ranch-style homes are tucked along Ascutney Street as it heads south out of town. Half-stories line small streets near the Connecticut River. Ranch-style homes on well-kept lawns sit amid tall trees on Huntington and Channing drives, just north of the downtown area. Many homes have outbuildings, and some offer attached garages. Out in the country, where lots can include dozens of acres of land, homes lurk among dense woods or sprawl near open farmland, and prices can range from around $820,000 to $1.3 million. Windsor holds a CAP Index Crime Score of 2, lower than the national average of 4.
New England homes line a quiet street in Windsor.
Cape Cod homes dot the landscape all across Windsor.
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Paradise Park, Mount Ascutney, many trails and river access
Outdoor recreation is a vital component of Windsor’s character. Paradise Park, in Windsor Town Forest, offers several trails around Lake Runnemede and through forests and wetlands. South of town, Mount Ascutney has undergone a volunteer-based revival. “Now there’s a J-Bar lift, a rope tow and a tubing run,” Kogut says. “All your neighbors are there volunteering.” Southeast Vermont offers a large network of trails, some of which cut through private land. “As long as you recreate responsibly, you can walk the trails through private land,” Kogut says. “It’s pretty nice to have right outside your door.” Great River Outfitters offers canoe and kayak tours and rentals on the banks of the Connecticut. The outfitter is also home to the Path of Life Sculpture Garden.
Well-maintained paths give visitors to Paradise Park easy access to Lake Runnemede in Windsor.
Windsor bikers size up the jumps at the bike park on Mount Ascutney.
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Downtown shops and eateries, Artisans Park and Brownsville Butcher & Pantry
While small, Windsor’s downtown area has more to it than many other nearby townships. Artisans Park, just north of the downtown and near Great River Outfitters, is home to Harpoon Brewery’s second location outside Boston, Silo Distillery, as well as Blake Hill Preserves and the Vermont Farmstead Cheese Company Market. Windsor Station Restaurant and Barroom serves pasta and craft cocktails in an old train depot. “The train comes right by the window every hour," Kogut says. "They left everything intact, so you really feel like you’re in a train station.” Price Chopper has groceries along U.S. Route 5. In the next town over, Brownsville Butcher & Pantry in West Windsor is a destination for its market, menu and community space in a former general store. “It’s all just community,” Kogut says. “You know everybody there.”
Residents of Windsor update their wardrobes with new threads from Cassie's Resale Boutique.
After a day of hiking and biking Mount Ascutney, Windsor residents enjoy a cold beverage from Brownsville Butcher & Pantry.
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Autumn Moon Festival and an all-season farmers market
Windsor’s Autumn Moon Festival, formerly known as Moon Dance, has been an annual event for over two decades. It fills downtown with live music, magic, educational activities, a pumpkin carving contest, kids' activities, vendors and a beer garden. The Windsor Farmers Market runs year-round, moving indoors during colder months.
Windsor School serves pre-kindergarten through 12th grade
Students in Windsor can attend Windsor Southeast Supervisory Union, of which Mount Ascutney School District is a part. Windsor School serves grades from pre-kindergarten through 12th and earns a C-plus grade from Niche. Students from other townships join Windsor School from grades nine through 12. High school seniors participate in the capstone program, in which students complete a self-directed research project and publicly exhibit their work.
Kids make friends that will last a lifetime at the Windsor School.
Students are eager to learn as soon as they walk through the doors at the Windsor School.
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Interstate 91 and Amtrak connect Windsor to surrounding areas
Interstate 91 runs near the downtown area’s western edge. U.S. Route 5 follows the river and cuts through downtown, becoming Main Street. Vermont Routes 12 and 44 are other significant roads. Claremont, New Hampshire, is about 10 miles away. Burlington International Airport is about 100 miles away. Windsor has daily Amtrak service, with the Vermonter stopping at Windsor-Mt. Ascutney Station. Mt. Ascutney Hospital is about a mile from the downtown area near I-91.
The Amtrak train makes a daily trip from Windsor to Washington D.C.
Public transportation helps Windsor residents move around the city easily.
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Written By
Ty Phelps
Photography Contributed By
Shawn Miller
Video By
Francisco de la Vera
Interested in learning more about homes in this area?
Reach out to
Susan Hickey,
an experienced agent in this area.
GreatSchools:
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On average, homes in Windsor, VT sell after 89 days on the market compared to the national average of 57 days. The median sale price for homes in Windsor, VT over the last 12 months is $290,000, up 5% from the median home sale price over the previous 12 months.
Sited on a knoll with lovely views in every direction, this spacious, sun filled Contemporary home was built to last! Using the finest materials, commercial grade mechanics, and custom millwork, this home imbues quality throughout.An impressive fireplace with a wood burning insert anchors the Great Room with sweeping walls of windows integrating indoor and outdoor spaces, and French doors
"The Plateau", originally part of the Kennedy Biscuit Co. (Nabisco) family estate, is nestled on a plateau at the end of a private road which greets you with open fields, mature trees, beautiful gardens, and a protected front-and-center view of Mt. Ascutney to the West and the Connecticut River to the East. This private peaceful setting includes an inground pool for those hot summer days, and two
Looking for an affordable way into homeownership? This ranch features 3 bedrooms and 1 full bath, this single-level home is perfect for first-time buyers or downsizers. Cozy up in the living room next to the fireplace or relax on the covered porch with your morning coffee. The easy, one-floor layout means low-maintenance living at a price that's hard to beat. Located just minutes from downtown
Come see and appreciate this recently rejuvenated and extraordinary home that includes 6 bedrooms and 4 bathrooms as well as a 2 car garage! Located just off the downtown village area, this unique property features historical charm and character with vintage woodwork, custom wood floors, high ceilings, spacious rooms and the nooks and crannies a classic home has to offer! Relax on the rear porch
Sited on a knoll with lovely views in every direction, this spacious, sun filled Contemporary home was built to last! Using the finest materials, commercial grade mechanics, and custom millwork, this home imbues quality throughout.An impressive fireplace with a wood burning insert anchors the Great Room with sweeping walls of windows integrating indoor and outdoor spaces, and French doors
Embrace the ultimate Vermont lifestyle with this 1950s ranch, perfectly situated on 6.8 sprawling acres of versatile land at 466 Esty Lane in Windsor. Combining nostalgic mid-century charm with extraordinary future potential, this property is an absolute dream for investors, developers, or anyone looking to build their ideal country homestead. The existing home offers 1,152 square feet of
Welcome to 23 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 1 bedroom, 1 bathroom, and 643 sq. ft. (13'4"x48) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient
Take a look at this rare chance to own a BRAND NEW home in the heart of Windsor. Built for efficiency, the house features a raised foundation to keep it out of the flood zone for extra peace of mind. The layout is practical and spacious, offering an open-concept first floor and large bedrooms upstairs.You are within walking distance to the Amtrak station and downtown, and our local Moover
This beautifully crafted 2024 "Incredible Tiny Home" built by Amish Artisans, is ready for its next owner. Thoughtfully designed for efficiency and comfort, the home features a convenient kitchen, a spacious bathroom, and a loft sleeping area with stairs for easy access. A mini-split system provides both heating and cooling, ensuring year-round comfort. Step outside to enjoy the well-built
Motivated seller! Price drop! A rare piece of Vermont history, thoughtfully preserved for modern living. Dating to 1790, this distinguished brick and frame Colonial stands as a testament to early New England craftsmanship — and it's ready for its next chapter. Meticulously maintained over the centuries and updated where it counts, this two-story home offers the warmth of wide-plank hardwood and
Welcome to 132 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features
Welcome to 11 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient
48.11 Acres of Spectacular Vermont Land with Panoramic Views!Discover a rare opportunity to own 48.11 acres of exceptional Vermont countryside in the heart of the Connecticut River Valley, often referred to as Vermont's "Shenandoah Valley" for its scenic beauty. This remarkable property offers breathtaking 180-degree views to the east and south, creating an unforgettable setting for a dream
welcome to this generously sized two bedroom apartment, perfect for those seeking comfort and convenience. Located on State Street, this unit offers a great in-town location, just a short walk to restaurants, schools, and shopping.The main level features a large kitchen with brand new fixtures including a breakfast bar and complemented by a separate dining room, ideal for family meals or
Newly renovated, 1-Bedroom, 1-Bath Apartment located on a secluded cul-de-sac near Hartland Four Corners, very convenient to Rte 91. Sunny entry room features large slider doors that lead out into garden area with views of Mt. Ascutney. Spacious Living Room, Galley Kitchen with Stainless-Steel refrigerator and electric stove, Large Bathroom with new vanity and extra-large Storage/Pantry. Brand
Welcome to 35 River Street, a charming home located in the heart of Windsor. This spacious property offers a flexible layout with multiple living areas, abundant natural light, and classic character throughout.The home features hardwood flooring, generous room sizes. Enjoy the comfort of a covered porch and a location close to downtown shops, restaurants, and local
Be the first to live in this beautiful brand-new 2-bedroom, 1-bath single-family home offering approximately 1,000 square feet of thoughtfully designed living space.This home features a bright, open layout with modern finishes throughout. The stylish kitchen includes contemporary cabinetry, stainless steel appliances, and ample storage, creating a functional and inviting space for
$2,900 per month
Beautiful Furnished Home with Cozy Rustic Finishes
Welcome to this warm and inviting fully furnished 3-bedroom, 1-bath home that blends rustic charm with modern comfort. The spacious open-concept kitchen and dining area features beautiful wood accents, generous cabinet storage, and a functional layout ideal for both everyday living and entertaining. The living room offers a bright and comfortable space filled with natural light—perfect for
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