Windsor Listings
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773-793 O'Brien Street in Windsor: Hants County Vacant Land for sale (Annapolis Valley) : MLS®# 202515545
773-793 O'Brien Street Windsor B0N 2T0 
$449,900Vacant Land- Status:
- Active
- MLS® Num:
- 202515545
Attention Developers! Explore the incredible potential of this lot on O’Brien Street in the heart of Windsor. This 2 acre property boasts a prime location in a high-traffic area, just a short stroll to all amenities, making it ideal for a range of ventures. Zoned for general commercial use, the possibilities are endless—imagine retail shops, professional offices, or a combination of these to maximize your investment. The property offers ample parking space, a valuable asset for any development. Don’t miss this chance to bring your project to life in one of Windsor’s most promising locations! More detailsListed by Royal LePage Atlantic - Valley(Windsor) and Royal LePage Atlantic (Dartmouth)- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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52-62 Gerrish Street in Windsor: Hants County Commercial for sale (Annapolis Valley) : MLS®# 202602489
52-62 Gerrish Street Windsor B0N 2T0
$875,000Commercial- Status:
- Active
- MLS® Num:
- 202602489
- Major Bus.:
- Office
- Floor Area:
- 9,522 sq. ft.
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. More detailsListed by Exit Realty Town & Country- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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125 Cottage Street in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202605584
125 Cottage Street Windsor B0N 2T0
$449,900Residential- Status:
- Active
- MLS® Num:
- 202605584
- Bedrooms:
- 3
- Bathrooms:
- 1
- Floor Area:
- 943 sq. ft.
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! More detailsListed by LPT Realty ULC- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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257 Wiley Avenue S in Windsor: Hants County Multi-Family for sale (Annapolis Valley) : MLS®# 202611033
257 Wiley Avenue S Windsor B0N 2T0
$1,290,000Multi-Family- Status:
- Active
- MLS® Num:
- 202611033
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. More detailsListed by Royal LePage Atlantic (New Minas)- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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154 Chestnut Street in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202611604
154 Chestnut Street Windsor B0N 2T0
$479,900Residential- Status:
- Active
- MLS® Num:
- 202611604
- Bedrooms:
- 3
- Bathrooms:
- 1
- Floor Area:
- 1,465 sq. ft.
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. More detailsListed by Royal LePage Atlantic - Valley(Windsor) and Royal LePage Atlantic (Dartmouth)- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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250 Gray Street in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202612123
250 Gray Street Windsor B0N 2T0
$569,999Residential- Status:
- Active
- MLS® Num:
- 202612123
- Bedrooms:
- 4
- Bathrooms:
- 2
- Floor Area:
- 1,644 sq. ft.
Step into the timeless charm of this classic Craftsman-style century home, featuring Boston headers, a grand foyer, formal dining room, and an expansive bead-board sun porch stretching the full length of the house. Rich with character, the home offers French doors, a cozy wood-insert fireplace, pantry/scullery kitchen, updated 4-piece bath, heat pumps, and upgraded electrical service. Perfectly positioned for exceptional walk-ability, you’re just steps from the curling club, library, post office, pubs, coffee shops, and ice cream parlour, with highway access only two minutes away. A detached garage/workshop with covered porch overhang adds even more versatility to this charming property. More detailsListed by Viewpoint Realty Services Inc.- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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76 Burgess Crescent in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202612140
76 Burgess Crescent Windsor B0N 2T0
$439,900Residential- Status:
- Active
- MLS® Num:
- 202612140
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 1,851 sq. ft.
Welcome to 76 Burgess Crescent, a beautifully designed 1-year-old semi-detached home offering modern style and everyday comfort in a prime location. The main floor features an open concept living room, dining area, and kitchen complete with custom cabinetry, quartz countertops, convenient main floor laundry, and a half bath. Upstairs, you’ll find a spacious primary bedroom with a walk-in closet and private ensuite bath, along with two additional generously sized bedrooms and a full main bath. Outside, enjoy a nicely tucked-in backyard perfect for relaxing or entertaining. Just Minutes away from all amenities Windsor has to offer and just 30 mins to HRM. More detailsListed by Royal LePage Atlantic - Valley(Windsor) and Royal LePage Atlantic (Dartmouth)- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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42-50 GERRISH Street in Windsor: Hants County Commercial for sale (Annapolis Valley) : MLS®# 202612432
42-50 GERRISH Street Windsor B0N 2T0
$1,650,000Commercial- Status:
- Active
- MLS® Num:
- 202612432
- Major Bus.:
- Medical
- Floor Area:
- 11,772 sq. ft.
42–50 Gerrish Street presents a mixed-use investment opportunity in the heart of Downtown Windsor, NS. The property features a combination of commercial and residential space within one of Windsor’s most established commercial corridors, surrounded by local businesses, healthcare services, and everyday amenities. The asset benefits from strong visibility, walkable access, and ample on-site parking accessed from Stannus Street, a rare feature within the downtown core. Conveniently located just minutes from Highway 101, the property offers accessibility for both tenants and customers while being positioned within a community continuing to see residential and commercial growth. More detailsListed by Holm Realty Limited- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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130 Gray Street in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202612454
130 Gray Street Windsor B0N 2T0
$489,000Residential- Status:
- Active
- MLS® Num:
- 202612454
- Bedrooms:
- 5
- Bathrooms:
- 3
- Floor Area:
- 2,147 sq. ft.
Welcome to 130A and 130B Gray Street! 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. The entire property is currently vacant, allowing you to hand-select your own tenants and set your own rental rates from day one, or Sellers are wiling to rent units prior to closing for new owners. More detailsListed by RE/MAX Nova (Halifax)- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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130 Gray Street in Windsor: Hants County Multi-Family for sale (Annapolis Valley) : MLS®# 202612453
130 Gray Street Windsor B0N 2T0
$489,000Multi-Family- Status:
- Active
- MLS® Num:
- 202612453
Welcome to 130A and 130B Gray Street! 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. The entire property is currently vacant, allowing you to hand-select your own tenants and set your own rental rates from day one, or Sellers are wiling to rent units prior to closing for new owners. More detailsListed by RE/MAX Nova (Halifax)- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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324 Wentworth Road in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202615038
324 Wentworth Road Windsor B0N 2T0
$329,900Residential- Status:
- Active
- MLS® Num:
- 202615038
- Bedrooms:
- 4
- Bathrooms:
- 1
- Floor Area:
- 1,018 sq. ft.
Located at Exit 5A in the heart of Windsor, this versatile 4-bedroom, 1-bath property offers a variety of possibilities. Currently zoned Commercial Transition and positioned directly across from local staples like Subway, A&W, and Needs, this location balances high visibility with everyday convenience and offers a straightforward, easy commute to Halifax. Inside, this move-in ready property feels fresh and inviting. It features a new coat of paint throughout, cute kitchen with stainless appliances, vinyl plank flooring, and stylish light fixtures. Whether you are searching for a cozy residential home, a solid rental investment, or a bright, accessible space for your small business, the adaptable floor plan can be opened up on either level to suit your needs. Outside, you’ll love the covered front porch for your morning coffee, and the private rear deck. With a deep gravel driveway for flexible parking and an unfinished basement for extra storage, this property is as practical as it is charming. The spacious rear lot also provides great potential for future expansion in a highly walkable, well-connected area. More detailsListed by Engel & Volkers (Wolfville) and Engel & Volkers- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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192/194 Albert Street in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202615191
192/194 Albert Street Windsor B0N 2T0
$475,000Residential- Status:
- Active
- MLS® Num:
- 202615191
- Bedrooms:
- 6
- Bathrooms:
- 4
- Floor Area:
- 2,251 sq. ft.
Looking for a turnkey investment opportunity? Welcome to 192 & 194 Albert Street, a duplex offering two side-by-side, two-storey units on a quiet, tree-lined street. Each unit features 3 above-grade bedrooms, 1.5 bathrooms, main-floor laundry, engineered hardwood flooring, heat pumps, electric baseboard heating, and all appliances are included. A large parking area at the rear provides ample space for tenants, and the roof was replaced in 2021 for added peace of mind. Ideally located within walking distance to grocery stores, the public library, and a variety of everyday amenities, this property offers both convenience and lasting rental appeal. Currently occupied by long-term tenants who are respectful, quiet, clean, and family-oriented, this is an exceptional opportunity to add a quality income property to your investment portfolio. More detailsListed by RE/MAX Nova (Halifax)- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
Data was last updated August 22, 2026 at 03:20 AM (UTC)