Windsor Real Estate

Windsor, Ontario, is a vibrant city that beautifully blends rich history with modern living, making it an ideal destination for both residents and visitors alike. Nestled on the southern banks of the Detroit River, Windsor boasts stunning waterfront views and a close-knit community atmosphere. As the southernmost city in Canada, it enjoys a unique position, just across the river from Detroit, Michigan, allowing for a diverse cultural exchange and easy access to the bustling metropolis.

Windsor is renowned for its thriving arts scene, with numerous galleries, theaters, and music festivals that celebrate local talent and creativity. The city is also home to the beautiful Windsor Sculpture Park, where visitors can stroll along the riverfront and admire a collection of impressive outdoor art installations. For those who appreciate the great outdoors, Windsor offers an array of parks and recreational facilities, including the expansive Ojibway Prairie Complex, perfect for hiking and wildlife observation.

The city's culinary scene is equally enticing, with a variety of restaurants that reflect its multicultural heritage. From cozy cafes to fine dining establishments, Windsor’s food offerings are sure to please every palate. Additionally, the city hosts several annual events, such as the Windsor International Film Festival and the Windsor-Essex Pride Fest, which foster a sense of community and celebration.

With its affordable housing options, excellent schools, and strong local economy, Windsor is an attractive place for families, young professionals, and retirees. Whether you're looking to invest in real estate or simply explore a charming city with a welcoming spirit, Windsor is a hidden gem waiting to be discovered.

Newest Listings in Windsor

$475,000

3 Beds ⋅ 2 Baths ⋅ 5108310 MLS

Pull off County Road and the gravel goes quiet under the tires as 16.35 acres in Windsor, Vermont open in grass, timber, and sky. Hubbard Brook moves through the land with water over stone, cool in the shade and bright where the light finds it, and a snowmobile trail crosses the acreage when winter takes the fields. I-91 sits close enough that the Upper Valley is an easy reach. That is 1268 County Road before anyone touches a doorknob. Stand long enough to smell the wet bank and feel how much ground comes with the house, then go inside to the finished second floor you can use tonight: two bedrooms, two full baths, and a primary suite that takes real space. The walk-in closet is the size of a room and the laundry lives in that closet, so the suite keeps its own rhythm. The primary bath does not force a choice. A jetted tub with a built-in water warmer and a separate walk-in shower mean steam or a long soak with tile underfoot, and two electric fireplaces add a low glow on cold nights. Sellers upgraded the electrical throughout to 200 amp service, and two propane hot-air furnaces split the house by level, the larger one warming the finished floor and the smaller one waiting on the first floor. That first floor is unfinished on purpose, bare rooms and open air where the next owner can draw walls, add square footage, and let the house grow into the acreage. One honest note belongs up front: the roof and the siding both need to be replaced, and with an appropriate offer the seller will escrow funds to complete that work. More photos will follow as belongings are packed and rooms open up. What you are buying is 16.35 acres, a finished floor that works, a first floor to invent, a 200 amp panel, a drilled well with softener and sediment filter, municipal sewer, cable internet, a carport, decks, and a plan for new roof and siding. Come for the land, stay for the suite, and leave with brook sound still in your head. 1268 County Road, Windsor, VT 05089. House plus 16.35 acres.

1268 County Rd, Windsor

$275,000

3 Beds ⋅ 2 Baths ⋅ 5107190 MLS

Property being sold as-is. Opportunity knocks with the potential this home holds with a little bit of elbow grease. This 2019 three bedroom, two full bathroom manufactured home sits on 5 acres in the low tax town of Windsor. The open floorplan offers a great flow with 2 bedrooms on one end and the primary suite on the other. The seller does not have the ability to remove much from the property so the majority of the contents will convey with the sale. The electricity is also off so it will make financing this property difficult. The seller is still residing in the home, so please DO NOT drive down the driveway without an appointment. Come see how this property can work for you!

83 Miller Rd, Windsor

$299,000

2 Beds ⋅ 1 Baths ⋅ 5106677 MLS

Welcome to 319 Back Mountain Road in Windsor, Vermont, a comfortable 2-bedroom ranch situated on approximately one acre in a peaceful country setting. The home features an updated kitchen and a spacious living and dining area with plenty of natural light, creating a warm and inviting space for everyday living and entertaining. A metal roof and updated heating system add to the home's practicality and ease of ownership. A one-car garage provides convenient parking along with additional storage space. Outside, the level yard with mature trees offers plenty of room for gardening, recreation, or simply enjoying the Vermont surroundings. Located along the eastern slopes of Mount Ascutney, with its hiking trails and recreational activities. This property offers a wonderful balance of rural living and convenience, with easy access to downtown Windsor, I-91, and the area's abundant recreational opportunities. Whether you're looking for a primary residence, Vermont getaway, or a home to make your own, 319 Back Mountain Road offers an appealing opportunity in a desirable Upper Valley location.

319 Back Mountain Rd, Windsor

$279,000

2 Beds ⋅ 1 Baths ⋅ 5103442 MLS

Completely rebuilt in 2014 (except for the storage room) and set on 2.51 acres spanning both Windsor and Hartland, this 2-bedroom, 1-bath ranch offers comfortable one-level living with plenty of potential. The open-concept living, dining, and kitchen area creates a functional layout, while the attached direct-entry garage and unfinished attached space provide excellent storage or future expansion possibilities. Outside, the property features a circular driveway, a partially level yard, a small, fenced area off the garage, a larger split-rail fenced paddock with a run-in, a storage shed, and a dedicated chicken coop area, offering flexibility for gardening, hobbies, small animals, or outdoor enjoyment. Conveniently located with easy access to area amenities, this property presents a wonderful opportunity to make it your own. Easy access to I-91, 23 min to DHMC, 15 min from West Lebanon, 22 min to Woodstock, 40 min to Okemo. Open house Saturday, August 8th, 10am-12pm

15 Rt 5 N, Windsor

$125,000

5101039 MLS

Special private land offering, rare 5 acre parcel, abutting a bird sanctuary: 850 acres of protected Windsor Grasslands State of Vermont Wildlife Management area. Additional acreage is available. Perk tests, test pits done. Off a public, quiet dirt road. Lovely maples, and a brook, add to its beauty. An outstanding opportunity for those seeking rural privacy, yet minutes from downtown Windsor, Mt. Ascutney Hospital and Rt. 91 with its easy access to West Lebanon, Hanover, NH, and all the Upper Valley has to offer. Seller is a licensed VT realtor and is selling a portion of his own homestead.

000 Marton Rd, Windsor

$225,000

3 Beds ⋅ 1 Baths ⋅ 5098856 MLS

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 Windsor's shops, restaurants, K-12 school, and Kennedys Pond, this home offers small-town charm with everyday convenience. Priced to sell at $225,000: Schedule your showing today.

24 Cherry St, Windsor

$299,000

2 Beds ⋅ 1 Baths ⋅ 5096070 MLS

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 single-level living space, featuring two comfortable bedrooms, one full bathroom, and a full basement providing excellent storage or workshop space. While the house requires renovation, it boasts solid bones and a layout ready for your personal touch. For those desiring more space, the structure is suited to easily add a second-floor expansion, allowing you to maximize the footprint and capture beautiful scenic views.The true crown jewel of this property is the expansive acreage. With 6.8 total acres at your disposal, there is incredible potential to subdivide the land into two additional separate lots. Adding to this investment appeal, the land layout accommodates separate entrance possibilities for the new potential lots, ensuring future privacy and ease of access. Nature lovers will be captivated by the extensive river frontage running right along the property line, complete with idyllic spots perfect for a private summer swimming area or peaceful afternoon relaxation by the water's edge.Location is everything, and this property delivers. Nestled on a quiet, serene dirt road, you will enjoy complete peace and privacy while remaining just a short drive close to downtown Windsor's shops, dining, and historic amenities. Outdoor enthusiasts will rejoice knowing that Mount Ascutney is less than five miles away, offering fantastic alpine skiing, snowboarding, and winter recreation right in your backyard, alongside summer hiking. Whether you choose to renovate the existing ranch, expand upward, or pursue the subdivision, 466 Esty Lane offers an unmatched canvas.

466 Estey Ln, Windsor

$1,399,000

4 Beds ⋅ 4 Baths ⋅ 5095057 MLS

"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 porches: one open air and one screened-in, with views into the New Hampshire hillsides. Inside, the house is open and bright with a wonderful flow throughout. The large living room features a wood-burning fireplace and plenty of windows streaming in lots of natural light. The formal dining room, with built-in cabinets and a second wood burning fireplace, connects to the kitchen which is open to the family room. A beautiful spindle staircase with oversized steps leads you upstairs to the four bedrooms, including the primary with an ensuite bath and an attached office. The main guest/children's bedroom features a magnificent turret style sunroom taking in views of the Connecticut River, and a second set of stairs leads back down to the mudroom. The full basement offers plenty of storage and all the utilities. The large 2 story garage offers room for 4 vehicles and plenty of storage on the 2nd floor. This unique property presents a rare opportunity to own a special homestead in the Windsor area, just minutes from downtown shopping and restaurants.

145 The Plateau, Windsor

$490,000

6 Beds ⋅ 4 Baths ⋅ 5089288 MLS

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 or enjoy the private yard and great living room that overlook the nearby pond providing a peaceful retreat at the end of a long day!

2 Pine St, Windsor

$669,000

3 Beds ⋅ 3 Baths ⋅ 5085664 MLS

Tucked away at the end of a quiet dead-end street, this beautifully reimagined contemporary Craftsman offers the perfect blend of privacy, nature, and modern comfort. Set on 5.12 wooded acres with a serene beaver pond and breathtaking mountain views, this one-of-a-kind property delivers peaceful living in one of New Hampshire’s lowest tax rate towns. Completely renovated down to the studs, this 3-bedroom home features 1 full bath and 2 three-quarter baths, thoughtfully designed for easy single-level living. The open-concept layout is highlighted by vaulted ceilings, exposed post-and-beam character, and abundant natural light throughout. The stunning new kitchen is a true centerpiece, showcasing quartz countertops, Energy Star Rated appliances, a gas stove, and double ovens—perfect for both everyday living and entertaining. The spacious living area is anchored by a cozy gas fireplace, creating a warm and inviting atmosphere year-round. Enjoy the convenience of first-floor laundry and step outside to expansive side and rear decks - ideal for taking in the incredible sunrise and sunset views or hosting gatherings surrounded by nature. Additional features include a detached 2-car garage, proximity to lake for swimming and boating, and easy access to numerous nearby hiking trails. Don’t miss this rare opportunity to own a private New Hampshire retreat with modern upgrades and timeless character. ** Recently appraised in March 2026 at $715,000, this exceptional property presents immediate value and built-in equity. A rare opportunity to own a turnkey mountain retreat that perfectly balances comfort, style, and nature. **

162 Rocky Ledge Rd, Windsor

$229,000

2 Beds ⋅ 1 Baths ⋅ 5085358 MLS

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 public transit service is ready to help. The community hospital is just a shore drive as well. Whether you want a low-maintenance home for yourself or a solid rental property near major employers, this new construction is a great choice.

29 National St, Windsor

$99,000

1 Beds ⋅ 1 Baths ⋅ 5079488 MLS

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 deck--perfect for converting in to a sunroom--as well as a screened gazebo and a storage shed included in the sale. Located in a small, quiet park just 4 miles from I-91, this property offers both charm and convenience. If you've ever dreamed of owning a Tiny Home, this is your opportunity!

505 Back Mountain Rd Unit 14, Windsor

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