Windsor Homes under $500,000

Welcome to Windsor, a vibrant city that beautifully blends rich history with modern living. Nestled in the heart of southwestern Ontario, Windsor is known for its stunning waterfront views along the Detroit River, offering residents a picturesque setting that is perfect for both relaxation and recreation. With a diverse community and a plethora of cultural events, Windsor is a fantastic place to call home.

One of the city's standout features is its affordability in the housing market, particularly for homes priced under $500,000. This makes Windsor an attractive option for first-time homebuyers, families, and those looking to downsize without sacrificing quality of life. The real estate landscape is diverse, with charming bungalows, spacious family homes, and contemporary condos available, catering to various tastes and needs.

Living in Windsor means enjoying a wealth of amenities, from beautiful parks and recreational facilities to a thriving arts scene and an array of dining options. The city boasts excellent schools and healthcare facilities, making it a family-friendly environment. Plus, with easy access to major highways and the nearby U.S. border, commuting and travel are a breeze.

In Windsor, you can find your dream home without breaking the bank. With the city's ongoing development and commitment to community enhancement, investing in Windsor real estate today means securing a bright future in a city that continues to grow and thrive. Come explore Windsor, where your ideal home awaits!

Newest Windsor Homes under $500,000

$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

$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

$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

$89,900

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

$96,232

2 Beds ⋅ 2 Baths ⋅ 5050701 MLS

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 energy-efficient construction, modern appliances, and low-maintenance materials, making it perfect for easy living. Located in a peaceful and well-maintained community, this home is ideal for those looking for a move-in-ready option in a convenient location. Don’t miss out on this opportunity! Contact us today for more details or to schedule a tour. The interior is 100% complete. Home is available for showing. This property participates in the Mobile Home Infill Program (MHIP) and is open to anyone who works or lives in Vermont. The park owner is offering up $4,000 in closing costs and a waiver of the first 2 months of lot rent.

108 Cubb Ct, Windsor

$87,826

1 Beds ⋅ 1 Baths ⋅ 5050702 MLS

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 construction, modern appliances, and low-maintenance materials, making it perfect for easy living. Located in a peaceful and well-maintained community, this home is ideal for those looking for a move-in-ready option in a convenient location. Don’t miss out on this opportunity! Contact us today for more details or to schedule a tour. The interior is approximately 90% complete. Interior showings will be available beginning August 15th. This property participates in the MHIP and is open exclusively to current residents of Vermont. The park owner is offering up $4,000 in closing costs and a waiver of the first 2 months of lot rent.

23 Cubb Ct, Windsor

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