Windsor Homes under $500,000

Welcome to Windsor, a vibrant city nestled in the heart of Ontario, Canada. Known for its rich history, diverse culture, and friendly community, Windsor offers a unique blend of urban living and natural beauty. With its picturesque waterfront along the Detroit River, residents enjoy stunning views and abundant recreational opportunities, including parks, trails, and marinas. The city is also home to a thriving arts scene, with galleries, theaters, and music festivals that celebrate local talent.

For those seeking an affordable yet charming place to call home, Windsor presents an impressive selection of properties under $500,000. Whether you’re a first-time buyer, a growing family, or looking to downsize, Windsor’s real estate market offers something for everyone. From cozy bungalows to modern townhouses, you’ll find homes that combine comfort and style without breaking the bank.

Windsor’s neighborhoods are diverse, each with its own unique character and amenities. Families will appreciate the access to excellent schools, while young professionals will enjoy the bustling downtown area filled with shops, restaurants, and entertainment options. Additionally, the city’s strategic location provides easy access to major highways and the U.S. border, making it an ideal spot for commuters.

Investing in a home in Windsor means becoming part of a welcoming community that values connection and growth. With a lower cost of living and a variety of housing options, Windsor is not just a place to live; it’s a place to thrive. Explore the possibilities today and discover your dream home in this charming city!

Newest Windsor Homes under $500,000

$140,000

2 Beds ⋅ 1 Baths ⋅ 5113821 MLS

Affordable 2 BR village home with an attached two vehicle carport. First floor has a small front porch, living room, dining room and kitchen. The second floor has an office area, two bedrooms and a door to the rear porch. Walking distance to schools and village shops. Immediate occupancy.

155 State St, Windsor

$289,000

2 Beds ⋅ 1 Baths ⋅ 5113320 MLS

Owned waterfront on the Connecticut River! This solid 2 bedroom, 1 bath home sits on a 0.94 acre lot with direct river frontage and hill views across to New Hampshire. Built in 1947, the house shows the quality craftsmanship of its era, with original woodwork, arched doorways, and handy built ins throughout. The spacious living room features a fireplace, and the dining area looks out over the open, park like yard straight to the river. The first floor offers a bedroom and a full bathroom. The entire second floor is a long primary bedroom with plenty of room to spread out. Out back, enjoy the large deck with space for a hot tub and more great water views. A breezeway connects the house to the attached one car garage. This riverfront property offers character, privacy, and a great location. A short drive gets you to the grocery store, and Interstate 91 with Exit 8 or 9 just a few miles away for easy commuting. A rare chance to own a home right on the Connecticut River in Windsor, Vermont.

459 Rte 5 S, Windsor

$315,000

3 Beds ⋅ 1 Baths ⋅ 5113301 MLS

Classic 1930s character meets thoughtful updates at 19 Weston Heights. This 1,532-square-foot Cape retains the charm of its era, including wood floors and a traditional gable roof, while offering the comfort and convenience of an updated home. With three bedrooms and one bath, the floor plan is comfortable and manageable, and the level lot offers plenty of room for gardening, outdoor entertaining, or simply enjoying your own backyard. Located close to downtown Windsor, you’ll have easy access to groceries, local farms and markets, dining, recreation, and the town’s growing collection of amenities. Convenient access to I-91 makes travel throughout the Upper Valley or south toward Claremont easy. A wonderful opportunity to enjoy the character of an older Vermont home with everyday conveniences close at hand. The home is being offered with furnishings currently in the house.

19 Weston Hts, Windsor

$349,000

3 Beds ⋅ 2 Baths ⋅ 5113217 MLS

Open House 2:00 to 5:00 Saturday 10/10. A renovated home with character, flexibility, and a neighborhood that welcomes you with open arms. Purchased in 2022 and thoughtfully renovated throughout by the seller, a licensed real estate professional. The kitchen and dining area, once divided by a half wall, have been opened into an inviting gathering space with vinyl plank flooring and a classic farmhouse sink. New appliances, windows, furnace, hot water heater, and bathroom fixtures bring modern comfort throughout. A welcoming mudroom with built-in storage bench opens to the kitchen and dining area, while the first floor also offers a bright laundry room, bedroom, half bath, and a former bedroom now transformed into a comfortable sitting room. The original 1940s staircase leads upstairs to two bedrooms with built-in closet features and a full bath with a charming clawfoot tub. The sitting room could easily be converted back to a fourth bedroom. Outside, the enormous expanded deck wraps around the front of the home and is gated for safe outdoor enjoyment. A new retaining wall was installed along the driveway before the deck renovation, and the driveway-accessible storage area has new doors. A roomy basement and generous yard provide space for storage, hobbies, and gardening. Best of all may be the Weston Heights neighborhood. Built in the 1940s around a neighborhood loop, it retains the friendly feeling it was designed to create. Neighbors walk dogs and cats, wave, stop to chat, and know one another. Renovated for modern living while retaining its character, this inviting home is ready for its next chapter.

128 Weston Hts, Windsor

$339,000

2 Beds ⋅ 2 Baths ⋅ 5112163 MLS

This wonderful home in a quiet convenient location may be a perfect fit for you! It has been lovingly well maintained with freshly painted interior, gorgeous refinished hardwood flooring, and new brand new carpet upstairs. The many upgrades such as replacement windows and the 2 mini splits offer efficiency and versatility and the standing seam roof and vinyl siding mean low maintainance costs for you. Great back deck for outside enjoyment overlooks the level back yard which offers nice area for playspace for young or old. The large primary bedroom was previously 2 bedrooms and could easily be put back to that. Showings start Monday Oct 5 so set up your appointment soon.

6 Mckenzie Dr, Windsor

$349,000

3 Beds ⋅ 1 Baths ⋅ 5111715 MLS

If you've been waiting for a home that feels fresh, comfortable, and ready for its next chapter, this might be the one you've been looking for. Tucked into a welcoming Windsor neighborhood, this charming 3 bedroom, 1 bath home has had the updates you want and the everyday convenience you need. The kitchen is brand new, the windows have been updated, the roof is newer, and everything has been freshly painted, giving you a home that feels clean, bright, and ready to enjoy from day one. And then there's the enclosed porch. With direct entry from the carport, it is the perfect spot to kick off your shoes, drop the groceries, enjoy your morning coffee, or settle in with a good book. It is one of those spaces that quickly becomes everyone's favorite. The neighborhood is another reason to fall in love with this home. Think evening walks, bike rides with the kids, friendly neighbors, and a place where Halloween still means kids wandering the streets in search of the best candy. It's the kind of neighborhood that feels connected and comfortable. Three bedrooms give you room for family, guests, a home office, or whatever life looks like for you. Add the carport, the thoughtful updates, and the convenient Windsor location, and you have a home that checks a lot of boxes without feeling like just another house. Come take a look. You may walk in and realize you've found the one you've been waiting for.

61 Channing Dr, 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

$184,900

5106186 MLS

RECENT RENOVATIONS INCLUDE A NEW HOT WATER HEATING SYSTEM, NEW PARTIAL ROOF AND FULLY REPAINTED INTERIOR. TWO - 2BR's APARTMENTS AND ONE - 3BR's APARTMENT. ESTIMATED GROSS RENTS $5,100.00 PER MONTH. SHORT NOTICE SHOWINGS AVAILABLE. READY FOR OCCUPANCY.

153 Main St, Windsor

$109,000

1 Beds ⋅ 1 Baths ⋅ 5102391 MLS

Why keep paying rent when you can own? This one bedroom just makes sense. Nothing overwhelming to maintain. A comfortable living space, a kitchen that works, and a bedroom to relax in. Outside you've got a yard that's easy to keep up with, and just enough space to enjoy. And the location can't be beat. Near downtown Windsor, grab dinner or coffee nearby, hop on 91 in minutes, or take a stroll along the Connecticut River. This is Vermont living without the price tag or the headache. Homes like this at this price point don't sit around, so come see it before it's gone!

52 Jarvis 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

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