Browse All Windsor NS Historical Properties for Sale

5 Beds ⋅ 202626461 MLS

Attention investors! Whether you are an investor looking for a strong income-producing property or a homeowner hoping to offset your mortgage with a rental income, this fully renovated legal duplex offers an outstanding opportunity. Complete interior renovation from top to bottom, the property features two large units; a 2 bedroom(possibly 3) 1 bath suite on the main level and a 3 bedroom, 2 bath unit spanning the 2nd and 3rd floors. Both units boast new kitchens, new bathrooms, new flooring throughout, new lighting and in unit laundry. A unique highlight is the third floor loft in the upper unit providing versatile extra living space. Complete with it's own kitchenette, bathroom and separate exterior entrance and newly constructed deck. This area is ideal for a private primary suite, guest accomodations or a self contained retreat/office/ artistic space.Enjoy the convenience of being within walking distance to local shops, coffee shops, pubs,parks,playgrounds,town swimming pool and the sports complex! With easy access to Hwy 101 this location offers excellent convenience for residents and commuters alike! With the major upgrades and improvements taken care of, this turnkey property is ready for its next owner! Whether you're expanding your portfolio or looking for a property that helps pay its own way, this versatile duplex offers an excellent opportunity in a convenient Windsor location.

130 Gray Street Unit B, Windsor

$439,900

5 Beds ⋅ 3 Baths ⋅ 202626336 MLS

Attention investors! Whether you are an investor looking for a strong income-producing property or a homeowner hoping to offset your mortgage with a rental income, this fully renovated legal duplex offers an outstanding opportunity. Complete interior renovation from top to bottom, the property features two large units; a 2 bedroom(possibly 3) 1 bath suite on the main level and a 3 bedroom, 2 bath unit spanning the 2nd and 3rd floors. Both units boast new kitchens, new bathrooms, new flooring throughout, new lighting and in unit laundry. A unique highlight is the third floor loft in the upper unit providing versatile extra living space. Complete with it's own kitchenette, bathroom and separate exterior entrance and newly constructed deck. This area is ideal for a private primary suite, guest accomodations or a self contained retreat/office/ artistic space.Could be converted back to a single family home with separate and shared living spaces.Enjoy the convenience of being within walking distance to local shops, coffee shops, pubs,parks,playgrounds,town swimming pool and the sports complex! With easy access to Hwy 101 this location offers excellent convenience for residents and commuters alike! With the major upgrades and improvements taken care of, this turnkey property is ready for its next owner! Whether you're expanding your portfolio or looking for a property that helps pay its own way ,this versatile duplex offers an excellent opportunity in a convenient Windsor location!

130 Gray Street Unit B, Windsor

$429,900

3 Beds ⋅ 2 Baths ⋅ 202625698 MLS

Welcome to 59 Tremain Crescent in Windsor! Tucked privately at the top of a paved driveway on a half-acre lot, this charming bungalow offers a peaceful setting in a popular, family-friendly subdivision. Enjoy the convenience of being within walking distance of the elementary school and local amenities, with Highway 101 access just minutes away. A welcoming front veranda leads into the sunny living room, where hardwood floors, charming built-ins and a cozy propane stove create an inviting place to gather. Thoughtful updates, including windows and heat pumps, add comfort throughout the home. The recently renovated eat-in kitchen features a large central island, beautiful backsplash, generous storage and its own heat pump-an ideal space for everyday meals and entertaining. Three bedrooms and a recently renovated bathroom are situated at the rear of the home. The sunroom offers a lovely spot to curl up with a book or enjoy your morning coffee, with access to both the attached single-car garage and the private back deck. Downstairs, the partially finished lower level provides additional space with a family room, (currently used as a bedroom), a three-piece bathroom, laundry, a workspace and ample storage. With its welcoming spaces, thoughtful updates and large private yard, this lovely home offers comfort and convenience in a sought-after Windsor neighbourhood!

59 Tremain Crescent, Windsor

$415,000

3 Beds ⋅ 1 Baths ⋅ 202624864 MLS

Looking for a home that's easy to move into and easy to live in? This sweet bungalow in central Windsor is ready for its next chapter, whether you're buying your first home or looking to simplify. The bright, open living and dining area is the heart of the home, with a large picture window that fills the space with natural light and leaves plenty of room for family meals, movie nights, or hosting friends. The kitchen has plenty of cupboard and counter space. The 3 bedrooms give you room to grow, set up a home office, or keep a guest room ready for visitors. Big-ticket items are already done. A recent electrical upgrade includes a new 200 amp service, generator panel, so you're prepared when the power goes out. There are 2 heat pumps to keep you comfortable year-round, with efficient heating in winter and cool air on summer days. Outside, the detached garage is great for parking, a workshop, or extra storage, and there's also a garden shed for tools and seasonal gear. The paved driveway has room for multiple vehicles. Out back, a private deck overlooks a spacious yard with a great spot for a fire pit, perfect for summer barbecues, gardening, or giving pets and kids room to play. All of this sits in a convenient central location, just minutes from downtown Windsor's shops, restaurants, schools, and services, with easy access to Highway 101 for commuting to the Valley or Halifax. Affordable, move-in ready, and low-maintenance, this is a smart start or a comfortable next step. Book your showing today!

122 Campbell Avenue, 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

$459,900

3 Beds ⋅ 1 Baths ⋅ 202611604 MLS

Welcome to 154 Chestnut Street, a beautifully updated 3-bedroom home where historic charm seamlessly meets contemporary sophistication—lovingly held in the same family for over 80 years! Ideally situated within walking distance of the prestigious King’s-Edgehill School, this home makes a striking first impression with its standout curb appeal and brand-new, welcoming front veranda that’s perfect for relaxing outdoors. Updated for year-round comfort, the home stays refreshingly comfortable during the summer months and holds its heat exceptionally well throughout the winter. Inside, thoughtful updates elevate the space. The main bathroom features a luxurious custom glass shower with all new plumbing. The main floor laundry room has all the plumbing intact, making it a straightforward process to convert it back into a second bathroom with laundry if desired. The main level offers a light-filled living room, a generous dining area designed for hosting, a gourmet-inspired kitchen and a quiet rear sunporch opening to a private, protected backyard with no rear neighbors. Upstairs, the primary suite includes an expansive walk-in closet, and the generous hallway at the top of the stairs leads you to the two remaining bedrooms, delivering the ideal blend of comfort and convenience. The photos truly do not speak to how beautiful this home really is. It really must be seen!!

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

240 King Street 19 Victoria 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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Browse All Windsor NS Historical Properties for Sale

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