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203/205 Gray Street, Windsor
$575,000
8 Beds ⋅ 3 Baths ⋅ 202625024 MLS
A rare opportunity in Windsor, this beautifully maintained century-old side-by-side duplex combines historic character with thoughtful updates and exceptional care. Both spacious units feature new kitchens, updated bathrooms, new flooring, improved heating, an additional half bath and numerous other upgrades, all completed without sacrificing the warmth and charm of the home. Unlike many duplexes, each side truly lives like a full-sized single-family home, offering four bedrooms plus a den and loads of living space. Outside, mature landscaping creates a beautiful backyard setting, while each unit enjoys its own attractive storage shed and separate driveway, adding to the privacy and independence of each side. The condition of this property is truly impressive, making it ideal for an owner-occupier looking to live comfortably on one side while renting the other to significantly offset their mortgage. With estimated rental potential of approximately $2,400-$2,700 per month per side, it also offers excellent flexibility for investors or multi-generational living. Properties of this age, size and character are rarely found in such remarkably well-kept condition. This is one you truly need to see in person to fully appreciate.

203/205 Gray Street, Windsor
20 Gray Street, Windsor
$474,900
6 Beds ⋅ 4 Baths ⋅ 202622069 MLS
Welcome to this spacious 2.5 storey home in an incredible Windsor location, just a short walk from local shops, restaurants, schools, and everyday amenities. With nearly 3,000 sq. ft. of living space, this family home offers 6 bedrooms, 2 full bathrooms, and 2 half baths, providing plenty of room for a growing family, guests, or those looking for flexible living space. The third level is a standout feature, offering a private primary suite complete with its own ensuite bath, a comfortable retreat tucked away from the main living areas. With its generous layout and multiple entrances, there are also plenty of possibilities for the future. The lower level could potentially be converted into a second unit with the addition of a kitchen, making this an attractive option for extended family or additional income. Alternatively, the property's layout and central location could lend itself well to a home-based business, offering the opportunity to live and work in one convenient location. A metal roof and ductless heat pump add practical value, while the walkable setting puts Windsor's amenities close at hand. Whether you're looking for a large family home, a property with income potential, or space to bring your business home, this property is ready to adapt to your needs.

20 Gray Street, Windsor
122 Victoria Street, Windsor
$634,900
8 Beds ⋅ 5 Baths ⋅ 202622055 MLS
Looking for a home with room for the whole family, flexible living space, and the potential to work from home or operate a business? This property offers an incredible amount of space and versatility in a convenient Windsor location, all within walking distance of local shops, restaurants, services, and amenities. This bungalow features 8 bedrooms and 4.5 bathrooms, with a welcoming main level centred around a beautiful country-style eat-in kitchen, a bright sunroom, comfortable living room, and access to the back patio. 3 bedrooms and 2 baths are also located on this level, including one with a whirlpool tub. The lower level offers plenty of options for a growing family, extended family or guests, with a large bedroom, walk-in closet, office, cozy propane fireplace, and 3 piece bath, plus 4 additional bedrooms and 3 more 3 piece bathrooms. The home is fully accessible, with a front wheelchair ramp and lifts remaining in place for stair access. Outside, you'll find a huge paved driveway with ample parking, a large deck with wheelchair ramp, storage shed, and a lovely back walkway framed by a paver stone retaining wall. Two heat pumps provide heating and cooling, while a propane generator provides peace of mind during power outages. Formerly an 8 unit private residential care facility, the property's unique layout also presents exciting possibilities for a home-based business or future commercial use, making this much more than just a family home.

122 Victoria Street, Windsor
790 King Street, Windsor
$4,750,000
28 Beds ⋅ 202615905 MLS
Build over 100 new units while collecting immediate rental income from an existing, fully retrofitted 18-unit apartment building (former school, renovated in 2018), plus a 2-bedroom house with double garage and storage shed—all on 4.45 acres of R-4 High Density Residential land with land use approval for approximately 126 total units. Commanding sweeping views over the Town of Windsor and located just minutes from amenities, schools, shops, Highway 101, and key commuter routes to Halifax and the Annapolis Valley, this property offers a rare combination of stable cash flow today and exceptional multifamily development potential through the construction of a new 100+ unit building.

790 King Street, Windsor
257 Wiley Avenue S, Windsor
$1,290,000
7 Beds ⋅ 202611033 MLS
257 Wiley Avenue presents an excellent opportunity to acquire a well-maintained legal 11-unit residential apartment building in the growing community of Windsor, Nova Scotia. Please note, the building contains 13 units but would require a change in the development agreement through the County office. Originally constructed circa 1899 and substantially renovated in 2013, this income-producing property combines historic character with important modern upgrades and long-term investment stability. The building features wood frame construction on a solid masonry brick foundation, with a gabled asphalt-shingled roof and attractive decorative wood siding that enhances curb appeal. Interior finishes include fire-rated drywall throughout, complemented by a mix of hardwood and laminate flooring, creating durable and appealing living spaces for tenants. The property is serviced by a 400-amp electrical system and heated with electric radiant baseboard heaters throughout the building. Plumbing includes 13 full 4-piece washrooms featuring tub/shower combinations, toilets, and sinks. Additional improvements include a municipal sewer main line replacement completed in November 2025, providing added confidence for future ownership. With its strong unit count, extensive renovations, solid construction, and desirable Windsor location, 257 Wiley Avenue represents a rare opportunity for investors seeking a stable, cash-flowing multi-residential asset with long-term upside potential.

257 Wiley Avenue S, Windsor

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