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
$399,900Residential- 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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154 Chestnut Street in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202611604
154 Chestnut Street Windsor B0N 2T0
$459,900Residential- Status:
- Active
- MLS® Num:
- 202611604
- Bedrooms:
- 3
- Bathrooms:
- 1
- Floor Area:
- 1,465 sq. ft.
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!! 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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790 King Street in Windsor: Hants County Multi-Family for sale (Annapolis Valley) : MLS®# 202615905
790 King Street Windsor B0N 2T0
$4,750,000Multi-Family- Status:
- Active
- MLS® Num:
- 202615905
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. More detailsListed by RE/MAX Nova (Halifax) and RE/MAX Nova- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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496 Highland Avenue in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202617287
496 Highland Avenue Windsor B0N 2T0
$569,900Residential- Status:
- Active
- MLS® Num:
- 202617287
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 1,573 sq. ft.
Welcome to 496 Highland Avenue, Windsor- a stunning brand-new home perfectly positioned at the top of a hill on a quiet dead-end street, offering modern style, quality craftsmanship and thoughtful design throughout! This beautifully finished two-storey, slab-on-grade home welcomes you with a bright, open-concept main living area, ideal for both everyday living and entertaining. The inviting living room features a sleek electric fireplace, while the dining area provides easy access to the side deck-perfect for enjoying your morning coffee or summer barbecues. The stylish kitchen is complemented by a convenient coffee bar pantry, adding both functionality and charm. A spacious mudroom with access to the attached single-car garage and a convenient two-piece powder room complete the main level. A ducted heat pump provides efficient heating and cooling throughout the home, ensuring year-round comfort. Upstairs, you'll find a well-designed layout offering two comfortable bedrooms, a full bathroom and a dedicated laundry room. The beautiful primary suite is a true retreat, featuring a spacious walk-in closet and an elegant ensuite with double vanities, a walk-in shower and a private water closet. Situated in a desirable Windsor neighbourhood close to schools, parks, shopping, and all amenities, this exceptional new construction home offers the perfect combination of contemporary finishes, practical living spaces, and a peaceful setting. Move in and enjoy the comfort and confidence that comes with brand-new construction! More detailsListed by Viewpoint Realty Services Inc.- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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Lot 29B Community Way in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202619762
Lot 29B Community Way Windsor B0N 2T0
$489,900Residential- Status:
- Active
- MLS® Num:
- 202619762
- Bedrooms:
- 2
- Bathrooms:
- 2
- Floor Area:
- 1,298 sq. ft.
Construction is officially underway! Welcome to your next chapter at the "Perfect Pear," a beautiful two-bedroom, two-bath semi-detached home in Windsor’s welcoming retirement community, "The Crossing." Step inside this single-level sanctuary and you'll instantly feel at home, discovering that downsizing truly means upsizing your lifestyle. Picture preparing meals in the gorgeous open-concept kitchen—complete with ample cupboards and a handy pantry—before hosting friends in the airy dining and living areas. The true hero of the home, however, is the sun-drenched sunroom, perfect for quiet, relaxing afternoons. At day's end, retreat to a spacious primary suite featuring double sinks, a walk-in shower, and a wonderfully roomy closet. Complete with an attached garage, an efficient ductless heat pump for year-round comfort, and the peace of mind of an 8-year Lux Home warranty, this property has it all. Located just 40 minutes from Halifax and even closer to Wolfville, it perfectly pairs everyday accessibility with the relaxed Valley lifestyle you’ve been dreaming of. More detailsListed by Engel & Volkers (Wolfville)- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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Lot 29A Community Way in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202619763
Lot 29A Community Way Windsor B0N 2T0
$489,900Residential- Status:
- Active
- MLS® Num:
- 202619763
- Bedrooms:
- 2
- Bathrooms:
- 2
- Floor Area:
- 1,298 sq. ft.
Construction is officially underway! Welcome to your next chapter at the "Perfect Pear," a beautiful two-bedroom, two-bath semi-detached home in Windsor’s welcoming retirement community, "The Crossing." Step inside this single-level sanctuary and you'll instantly feel at home, discovering that downsizing truly means upsizing your lifestyle. Picture preparing meals in the gorgeous open-concept kitchen—complete with ample cupboards and a handy pantry—before hosting friends in the airy dining and living areas. The true hero of the home, however, is the sun-drenched sunroom, perfect for quiet, relaxing afternoons. At day's end, retreat to a spacious primary suite featuring double sinks, a walk-in shower, and a wonderfully roomy closet. Complete with an attached garage, an efficient ductless heat pump for year-round comfort, and the peace of mind of an 8-year Lux Home warranty, this property has it all. Located just 40 minutes from Halifax and even closer to Wolfville, it perfectly pairs everyday accessibility with the relaxed Valley lifestyle you’ve been dreaming of. More detailsListed by Engel & Volkers (Wolfville)- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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920 King Street in Windsor: Hants County Commercial for sale (Annapolis Valley) : MLS®# 202620028
920 King Street Windsor B0N 2T0
$549,900Commercial- Status:
- Active
- MLS® Num:
- 202620028
- Major Bus.:
- Office
- Floor Area:
- 2,524 sq. ft.
Unlock the potential of this high-exposure mixed-use property in the heart of Windsor. Situated on a prominent corner lot, this GC (General Commercial) zoned property offers outstanding flexibility for investors, entrepreneurs, and developers alike. The main level features a commercial space with excellent street visibility, making it ideal for a wide variety of retail, office, or service-based businesses permitted under GC zoning. Above, you'll find a spacious 4 bedroom residential unit, creating the opportunity for rental income, owner occupancy, or a live/work lifestyle. Whether you're looking to establish your own business, expand your investment portfolio, or redevelop a prime commercial site, the possibilities here are extensive. The generous lot provides room for parking, outdoor use, or future development potential, subject to municipal approvals. Located on one of Windsor's busiest corridors, the property benefits from exceptional daily traffic exposure and is just minutes from downtown amenities, King's-Edgehill School, Highway 101, and the gateway to the Annapolis Valley. Windsor continues to experience steady growth thanks to its strategic location between Halifax and the Valley, making this an excellent opportunity to invest in an evolving community. Highlights: GC (General Commercial) zoning Commercial space plus residential apartment Corner lot offering excellent visibility Ideal for owner-operators, investors, or redevelopment High-traffic location with excellent exposure HST is applicable to the purchase price. More detailsListed by RE/MAX Nova (Halifax)- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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155 Wiley Avenue in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202620274
155 Wiley Avenue Windsor B0N 2T0
$449,900Residential- Status:
- Active
- MLS® Num:
- 202620274
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 1,344 sq. ft.
A perfectly renovated 1.5-storey in the heart of Windsor. Within walking distance to all town amenities, the Hants County Aquatic Centre, and with quick highway access, this property is positioned in a well-established neighbourhood and has been thoughtfully designed with function in mind for a variety of different buyers. Situated on a quaint corner lot, this property features a paved driveway, detached single-car garage, a landscaped lot with a privacy hedge, and is steps away from the sidewalk to enjoy your afternoon strolls around town. Inside you will find an open-concept main living space with a brand-new, crisp and clean kitchen with stainless steel appliances included. There is a formal dining space, vinyl plank flooring throughout, and the home is freshly painted. A main-floor bedroom and a beautifully modern 4 pc bath complete the main. The second level consists of a good-sized landing, the perfect place for a reading nook, two generous-sized bedrooms, with the primary including a walk-in closet. There is another fully renovated 4 pc bath, with stylish fixtures and designs throughout. The basement is unfinished but has potential to finish and is the perfect place for storage. Newer windows, siding, front and back deck, roof shingles, an updated 200 amp electrical panel, and municipal services make this property the perfect stress-free home to move into and relax. Situated on a charming street with well-kept neighbours and a bustling town under 45 minutes to HRM and Wolfville, this property boasts potential, easy living and will make a wonderful home for you. Book your viewing today! More detailsListed by Exit Realty Town & Country- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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Lot Community Way in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202620590
Lot Community Way Windsor B0N 2T0
$449,900Residential- Status:
- Active
- MLS® Num:
- 202620590
- Bedrooms:
- 2
- Bathrooms:
- 2
- Floor Area:
- 1,029 sq. ft.
Check out the newly launched Cottage Home Collection at The Crossing! If you've been dreaming of the perfect retirement, welcome to Windsor—the place everyone wants to settle down and enjoy the good life. With easy access to the highway for commuting, and hospitals and grocery stores just minutes away, golf courses in close proximity, this welcoming community proves that downsizing your space truly means upsizing your lifestyle. This charming two-bedroom, 1.5-bath cottage designed as affordable footprint homes, they don't compromise on luxury, offering beautiful "big house" finishes throughout. Picture yourself sipping your morning coffee on the covered front porch, or enjoying a peaceful evening on the covered back deck, allowing you to comfortably take in the beauty of the changing seasons. Complete with a convenient small storage garage and an energy-efficient heat pump for reliable heating and cooling all year round, these homes have everything you need. It’s time to embrace the relaxed, worry-free living you deserve! *****PID to be subdivided and lot size to be determined once subdivision is completed. This is a facsimile listing **** More detailsListed by Engel & Volkers (Wolfville)- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
Data was last updated October 20, 2026 at 03:20 AM (UTC)