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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91 Burgess Crescent in Windsor: Hants County Multi-Family for sale (Annapolis Valley) : MLS®# 202527858
91 Burgess Crescent Windsor B0N 2T0
$678,350Multi-Family- Status:
- Active
- MLS® Num:
- 202527858
Modern "Open Concept" two storey on town services and only minutes from all amenities. All doors are 36" wide. Fully finished 1 bedroom apartment. Quality laminate flooring throughout finished areas. Main unit has 2 1/2 baths, walk-in closet and en-suite in Primary Bedroom, laundry closet on second level. Plumbing fixtures through builder's samples (or an allowance as negotiated) Optional hard wood stairs to second level add $6,000 plus HST. Cabinet allowance to cover both units is $24,000.00 plus H.S,T., Lighting allowance $1,500.00 plus H.S.T. Fully landscaped lot with double wide Gravel driveway. 7 Year Atlantic New Home Warranty. Act quickly, and choose your own interior colours. Walk out Open concept Basement apartment has a huge Great Room which engulfs the kitchen, dining and living rooms, and a large primary bedroom with walk-in closet, quality cabinets includes built in H.R.V. Conveniently located near the hospital, shopping and highway. More detailsListed by Century 21 Trident Realty Ltd.- 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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549 O'Brien Street in Windsor: Hants County Commercial for sale (Annapolis Valley) : MLS®# 202603725
549 O'Brien Street Windsor B0N 2T0
$2,240,000Commercial- Status:
- Active
- MLS® Num:
- 202603725
- Major Bus.:
- Other
PRIME MIXED USE DEVELOPMENT SITE. Approved Development Agreement for 2 buildings, up to 112 residential units and 10,000 sq ft of ground-level commercial in the growing town of Windsor! Position your next project in this amenity-rich community with a vibrant downtown core, renowned King's-Edgehill School, modern West Hants Sports Complex and local hospital all within walking distance. Flanking existing retail, the site is steps to the picturesque plaza park, the Tregothic trail and walking distance to the charming local foodie scene with the Gerrish & Gray cafe, Hole in the Wall and Naked Crepe. Ski Martock and On Tree Adventure Park are only a 10-minute drive. As the desirable gateway to the Annapolis Valley. Windsor is 20 minutes to Wolfville, Acadia University and Nova Scotia's beautiful wine region, and an easy 45 minute drive to downtown Halifax. Full architectural drawing package available. More detailsListed by Engel & Volkers (Wolfville)- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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549 O'Brien Street in Windsor: Hants County Multi-Family for sale (Annapolis Valley) : MLS®# 202603724
549 O'Brien Street Windsor B0N 2T0
$2,240,000Multi-Family- Status:
- Active
- MLS® Num:
- 202603724
PRIME MIXED USE DEVELOPMENT SITE. Approved Development Agreement for 2 buildings, up to 112 residential units and 10,000 sq ft of ground-level commercial in the growing town of Windsor! Position your next project in this amenity-rich community with a vibrant downtown core, renowned King's-Edgehill School, modern West Hants Sports Complex and local hospital all within walking distance. Flanking existing retail, the site is steps to the picturesque plaza park, the Tregothic trail and walking distance to the charming local foodie scene with the Gerrish & Gray cafe, Hole in the Wall and Naked Crepe. Ski Martock and On Tree Adventure Park are only a 10-minute drive. As the desirable gateway to the Annapolis Valley. Windsor is 20 minutes to Wolfville, Acadia University and Nova Scotia's beautiful wine region, and an easy 45 minute drive to downtown Halifax. Full architectural drawing package available. More detailsListed by Engel & Volkers (Wolfville)- 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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332 Wilson Street in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202609629
332 Wilson Street Windsor B0N 2T0
$459,900Residential- Status:
- Active
- MLS® Num:
- 202609629
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 2,208 sq. ft.
Mornings begin slowly here. Coffee in the sunroom beside the warmth of the propane fireplace, natural light pouring through the windows as the backyard comes to life. In every season, this home feels bright, comfortable, and easy to enjoy. Set on a desirable, walkable street in Windsor, this bungalow offers quiet, laid back living with the convenience of a reasonable commute to Halifax. Surrounded by the beauty of the Annapolis Valley, adventure and charm exist in every direction, from Ski Martock and local wineries to walking trails, farm markets, and locally loved cafes and restaurants. The main level of the home features spacious living areas, two sizeable bedrooms, and multiple gathering spaces, including two charming fireplaces that bring warmth and character into the home. Large windows create an airy feel and allow sunlight to fill the space from morning to evening. The sunroom is truly special, offering a peaceful space to read, unwind, or gather with family and friends, with direct access to the patio. The attached garage adds everyday convenience and comfort while also providing extra storage, easy access to the home and a practical space for hobbies, tools or outdoor gear. The lower level opens up even more possibilities with its own kitchen, full bathroom, bedroom, and living area, making it ideal for multigenerational living, extended guests, or potential income use. A large utility and laundry room provides exceptional storage and functionality. Windsor itself is rich in history, culture, and community spirit. Known for the world famous Windsor Pumpkin Regatta and the Hants County Exhibition dating back to the 1700s, this charming town offers a welcoming small town feel with beautiful historic homes, walkable streets, and the Avon River Causeway Trail just moments away. This is a home that offers comfort, flexibility, and connection to community, nature and a slower pace of life. More detailsListed by EXP Realty of Canada Inc.- 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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354 Wentworth Road in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202611102
354 Wentworth Road Windsor B0N 2T0
$349,900Residential- Status:
- Active
- MLS® Num:
- 202611102
- Bedrooms:
- 2
- Bathrooms:
- 1
- Floor Area:
- 788 sq. ft.
Welcome to 354 Wentworth Road, a beautifully updated and move in ready 2 bedroom, 1 bath home offering modern comfort, convenience, and an incredible outdoor lifestyle just minutes from Windsor and seconds to Highway 101. Originally renovated from top to bottom with updates including flooring, kitchen cabinetry, windows, siding, roofing, heat pump, and more, this home features a bright open concept layout that feels both functional and inviting. Since its last sale, the property has been taken to the next level with a fully transformed backyard oasis complete with a beautifully designed fenced outdoor space perfect for entertaining, relaxing, or enjoying quiet evenings at home. Whether you’re a first time buyer, downsizer, or someone looking for a turnkey property with major charm inside and out, this one is sure to impress at $375,000. More detailsListed by Royal LePage Anchor Realty- WHITNEY PURDY
- EXIT REALTY TOWN & COUNTRY
- 1 (902) 6983883
- Contact by Email
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1802 King Street in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202611309
1802 King Street Windsor B0N 2T0
$389,900Residential- Status:
- Active
- MLS® Num:
- 202611309
- Bedrooms:
- 2
- Bathrooms:
- 2
- Floor Area:
- 1,433 sq. ft.
Welcome to 1802 King Street in Windsor, a beautifully renovated home that blends century charm with modern comfort. The updated, spacious 4 years old kitchen is ready to welcome a new family. The combined living and dining area is warm and inviting, filled with natural light and perfect for everyday living and entertaining. A large family room on the main floor offers great flexibility and could easily be used as a primary bedroom or a spacious home office. Upstairs, you will find comfortable bedrooms along with a well-designed bathroom combined with laundry for added convenience. Enjoy your morning coffee on the wraparound deck, adding to the home’s charm and functionality. Additional features include a spacious shed for all your outdoor storage needs and a new concrete driveway that easily accommodates four or more vehicles. Ideally located near schools, parks, shopping, and all amenities Windsor has to offer. A wonderful place to call home — don’t miss this opportunity! More detailsListed by RE/MAX NOVA (Windsor)- 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
$499,900Residential- 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
$599,000Residential- 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
Data was last updated June 23, 2026 at 07:20 AM (UTC)