Windsor NS Historical Real Estate, Homes for Sale

2 Beds ⋅ 2 Baths ⋅ 202620698 MLS

Lovingly cared for by the same family for more than the past 40 years, this charming century home is ready to welcome its next chapter. Full of character and warmth, this beautifully maintained property offers the perfect blend of historic charm and comfortable everyday living, all in the heart of Windsor. The main level features inviting living and dining spaces filled with natural light, original character details, and a warm, welcoming atmosphere. The kitchen offers plenty of cabinetry and workspace, with a convenient layout that makes everyday living and entertaining easy. Upstairs, you’ll find two comfortable bedrooms, a versatile den currently being used as a walk-in closet, and a full bathroom with the added convenience of laundry on this level. The uppermost floor is currently used primarily for storage and offers exciting potential for the future. With the right vision and exploration, this space could provide room for two additional bedrooms, a home office, studio, or other living space to suit your needs. Outside, the fully fenced backyard is private, manageable, and designed for enjoying rather than maintaining. There’s room for gardening, relaxing, entertaining, or simply enjoying a summer evening outdoors, without spending all your free time keeping up with the yard. The property also offers convenient paved parking and a welcoming front porch that adds to the home’s undeniable curb appeal. Located in the heart of Windsor, you’ll be close to local shops, restaurants, schools, recreation, and the many amenities that make this community such a wonderful place to call home. If you’re looking for a home with history, character, flexibility, and a location that lets you enjoy more of what Windsor has to offer, this one checks all the boxes. Call your agent to book your viewing today.

344 Gray Street, Windsor

$329,000

3 Beds ⋅ 2 Baths ⋅ 202617688 MLS

Character Home in Windsor. This 1935 classic offers 3 bedrooms, 1.5 bathrooms, and a wealth of historic charm on a generous lot, use your newer Napoleon fireplace insert in the winter for that cozy wood heat. Privacy is great on your back deck overlooking the sloping yard. Enjoy ultimate convenience with an incredibly walkable location close to schools, local shops, a heated public pool, and vibrant downtown restaurants. An easy 40-minute drive to Halifax and 20 minutes to New Minas makes this the perfect blend of small-town charm and city accessibility.

475 Albert Street, Windsor

$449,900

5 Beds ⋅ 202616224 MLS

Looking to expand your investment portfolio? This well-maintained fourplex in the heart of Windsor offers an incredible opportunity! Whether you're an investor seeking a solid rental property or a buyer looking to live in one unit while the other 3 help offset your mortgage, this property delivers flexibility and potential. Featuring one 2 bedroom unit and three 1 bedroom units, there's a layout to suit a variety of tenants. The property provides a spacious deck, while the yard creates an inviting outdoor space for residents to relax and unwind. Ample on-site parking ensures convenience for all tenants. Ideally located within walking distance to schools, shopping, restaurants, and everyday amenities, this is a highly desirable location that continues to attract renters. Don't miss your chance to own a fantastic multi-unit property in one of Windsor's most convenient neighbourhoods!

861-865 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

$449,900

5 Beds ⋅ 202612453 MLS

130 Gray Street represents a rare turn-key cash-flowing opportunity in Downtown Windsor. Delivered fully vacant with two separate power meters and recent capital upgrades (roof 2023, electrical, plumbing, kitchens, and baths), an investor can capture current market rents immediately without rent-control restrictions. At a $449,900 acquisition price, the property projects an 8.27% Cap Rate and over $1,000/month in net positive cash flow after debt service—backed by West Hants' long-term commuter population growth along the Highway 101 corridor. This renovated legal duplex with two power meters, separate unit entrances, features a spacious 2-bedroom, 1-bathroom unit on the main level, and a 3-bedroom, 2-bathroom unit spanning the second and third floors. Each unit boasts a brand-new kitchen, modern bathrooms, fresh flooring throughout, bright LED lighting, and dedicated in-suite laundry. The real showstopper is the upper level of Unit 130B, which offers a bonus third-story loft space. Complete with its own kitchenette, bathroom, and separate exterior entrance via a newly constructed deck, this area can easily function as a private primary suite, a guest setup, or a premium bachelor-style space. Located just steps away from local shops, festival grounds, the historic Mermaid Theatre, and public transit, while offering effortless access to Highway 101 for an easy commute. Extensive recent upgrades include a new roof (2023), replaced exterior cedar shingles front of the house, fresh interior/exterior paint, some new vinyl windows, brand-new doors with new hardware, insulated basement walls and upgraded electrical and plumbing systems. One dedicated parking space is provided for the upper unit, with abundant street parking right outside.

130 Gray Street, Windsor

$449,900

5 Beds ⋅ 3 Baths ⋅ 202612454 MLS

130 Gray Street represents a rare turn-key cash-flowing opportunity in Downtown Windsor. Delivered fully vacant with two separate power meters and recent capital upgrades (roof 2023, electrical, plumbing, kitchens, and baths), an investor can capture current market rents immediately without rent-control restrictions. At a $449,900 acquisition price, the property projects an 8.27% Cap Rate and over $1,000/month in net positive cash flow after debt service—backed by West Hants' long-term commuter population growth along the Highway 101 corridor. This renovated legal duplex with two power meters, separate unit entrances, features a spacious 2-bedroom, 1-bathroom unit on the main level, and a 3-bedroom, 2-bathroom unit spanning the second and third floors. Each unit boasts a brand-new kitchen, modern bathrooms, fresh flooring throughout, bright LED lighting, and dedicated in-suite laundry. The real showstopper is the upper level of Unit 130B, which offers a bonus third-story loft space. Complete with its own kitchenette, bathroom, and separate exterior entrance via a newly constructed deck, this area can easily function as a private primary suite, a guest setup, or a premium bachelor-style space. Located just steps away from local shops, festival grounds, the historic Mermaid Theatre, and public transit, while offering effortless access to Highway 101 for an easy commute. Extensive recent upgrades include a new roof (2023), replaced exterior cedar shingles front of the house, fresh interior/exterior paint, some new vinyl windows, brand-new doors with new hardware, insulated basement walls and upgraded electrical and plumbing systems. One dedicated parking space is provided for the upper unit, with abundant street parking right outside.

130 Gray Street, Windsor

$479,900

3 Beds ⋅ 1 Baths ⋅ 202611604 MLS

Welcome to 154 Chestnut Street, a meticulously renovated 3 bedroom, 1.5-storey residence where historic charm meets contemporary sophistication, and has stayed in the same family for over 80 years! Ideally situated within walking distance of the prestigious King’s-Edgehill School, this home impresses from the outset with its striking entry and inviting new front veranda. The interior has undergone extensive updates, including a beautifully modern bathroom featuring a custom glass shower. The main level offers a light-filled living room, a generous dining area designed for hosting, and a gourmet-inspired kitchen. Practicality is enhanced by a main-floor laundry suite and a rear sunporch that opens to a private, protected backyard with no one building behind you. Upstairs, the primary suite features an expansive walk-in closet, offering a perfect blend of luxury and convenience in the heart of Windsor.

154 Chestnut Street, 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

$399,900

3 Beds ⋅ 1 Baths ⋅ 202605584 MLS

Welcome to 125 Cottage Street, perfectly situated on a spacious lot at the end of a quiet cul-de-sac in Windsor. Ideally located next to a nursery school and minutes from Hants Community Hospital, Highway 101 and local amenities. Freshly painted and new flooring throughout. Recent high-value upgrades include an updated bathroom (2026), large and improved carport (2025) and new back deck (2025). With a new oil tank (2024) and a durable metal roof, this is an ideal find for young families or those looking to settle in historic Windsor. A large cement basement provides extra space below. The R-4 Zoning is versatile for investors or entrepreneurs. Bring your dream!

125 Cottage Street, Windsor

$875,000

202602489 MLS

Well-positioned mixed-use investment property offering current income with exceptional development potential. Located in Windsor, one of the Annapolis Valley’s fastest-growing communities. The main floor features two established commercial/retail units (approx. 3,000 sq ft), both currently occupied. A large front display window enhances visibility and street presence, making the retail/office space well-suited for a wide range of businesses. Unit 1 has a large open office/reception area, a washroom, 3 offices (one currently being used for storage, and a 4th large boardroom/office area. Unit 2 has a spacious reception area, two office spaces, and a washroom. Also on the main level, Unit 3 is a previously rented, currently undeveloped commercial/warehouse area with direct access from Stannus Street. This space includes multiple rooms and a kitchen area and offers excellent development potential. The second floor offers two, 2-bedroom residential apartments, with tenants responsible for their own heat/electricity. The entire third floor, approximately 2,000 square feet, remains undeveloped and presents a rare opportunity for expansion, such as additional residential units, subject to buyer’s plans and approvals. This property includes two PIDs, with the second PID comprising a parking lot accessible from Stannus Street, a valuable asset for both commercial and residential tenants. Situated in the center of town, with excellent exposure, this property is well-suited for investors seeking a combination of stable income, value-add potential, and long-term growth in a thriving Annapolis Valley community.

52-62 Gerrish Street, Windsor

$550,000

202602010 MLS

Exceptional development opportunity located in the heart of Windsor offering approximately 5640 square feet over two floors with approximately an additional 7900 sq ft on the basement level. Building sits on an 11 600 sq ft corner lot with road frontage on three sides. The building is serviced with municipal water & sewer. Most recently used by the Dept of Justice as a court house, facilities reflect this use. Offers are subject to approval of West Hants Municipal Council and must follow their procedures. See instructions for further details and documents.

240 King Street 19 Victoria Street, Windsor

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