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Windsor Properties

Windsor NS, historic family community in the Annapolis Valley

Windsor is a heritage community with a rich history and is currently experiencing a rebirth. The town is once again growing and prospering as developments and construction can been seen all over town.
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  • 543 & 549 O'Brien Street in Windsor: Hants County Commercial for sale (Annapolis Valley) : MLS®# 202507647

    543 & 549 O'Brien Street Hants County Windsor B0N 2T0
    Main Photo: 543 & 549 O'Brien Street in Windsor: Hants County Commercial for sale (Annapolis Valley)  : MLS®# 202507647
    $6,450,000
    Commercial
    Status:
    Active
    MLS® Num:
    202507647
    Major Bus.:
    Shopping Centre
    Floor Area:
    10,000 sq. ft.
    INVESTMENT OPPORTUNITY: FULLY LEASED RETAIL PLAZA AND MULTI RESIDENTIAL DEVELOPMENT LAND Maximize your investment portfolio with the combination of this four-unit, fully-leased retail plaza PLUS adjacent mixed use development site! This landmark O'Brien retail building was newly constructed in 2023 and boasts national-chain tenants, ample parking, premium street exposure, top construction methods and striking curb appeal. Tie in the adjacent mixed use parcel that already has a development agreement in place for up to 112 residential units over 2 buildings plus another 10,000 SF of ground level commercial. Perfectly positioned as the epi-centre of Nova Scotia's four season lifestyle destination, Windsor is the connector between Halifax Regional Municipality and the Annapolis Valley wine-region. Area amenities include: Hospital, Recreation Sports Complex, internationally renowned King's Edgehill School, charming downtown core, thriving foodie scene, Ski Martock, ample trail systems, waterfront park and so much more. Only 45 minutes to downtown Halifax. Be part of one of the fastest growing regions in Canada. More details
    Listed by Engel & Volkers (Wolfville)
    ZACH FRAIL
  • 549 O'Brien Street in Windsor: Hants County Commercial for sale (Annapolis Valley) : MLS®# 202507646

    549 O'Brien Street Hants County Windsor B0N 2T0
    Main Photo: 549 O'Brien Street in Windsor: Hants County Commercial for sale (Annapolis Valley)  : MLS®# 202507646
    $2,450,000
    Commercial
    Status:
    Active
    MLS® Num:
    202507646
    Major Bus.:
    Other
    PRIME MIXED USE DEVELOPMENT SITE Attention builders - Approved Development Agreement for up to 112 residential units and 10,000 SF of 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 recreation complex and local hospital all within walking distance. Flanking existing retail, the site is steps to the picturesque plaza park, a renowned location for film producers, 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. Drawing package available for 109 units. More details
    Listed by Engel & Volkers (Wolfville)
    ZACH FRAIL
  • 993 King Street in Windsor: Hants County Multi-Family for sale (Annapolis Valley) : MLS®# 202509769

    993 King Street Hants County Windsor B0N 2T0
    Main Photo: 993 King Street in Windsor: Hants County Multi-Family for sale (Annapolis Valley)  : MLS®# 202509769
    $1,242,000
    Multi-Family
    Status:
    Active
    MLS® Num:
    202509769
    One of a kind property . Spot zoned R4 to allow many uses. Presently 8 units each is the size of a single family home 6 bungalow units and a Century side by side Duplex . Each unit has 3br,LR,DR,KIT and basement for rough storage. The large century units have finished attics. Each unit pays heat and lights and has - in unit laundry. This is basically 8 3br houses. Wonderful location with Pleasant grounds and greenery. Great live in property or investment. This property has below market rents but can bring in a truck load of money. MWH says this lot can have up to 24units(see attached Zoning uses) This is a property with many uses and much opportunity. Big family or Group every one can have their on house .with R-4 Zoning B&B is allowed - Rooming house is allowed. Home for special care or residential care is allowed. One Bungalow unit can be viewed prior to offering. Cash back on closing for improvements. More details
    Listed by City St Realty
    ZACH FRAIL
  • 172, 184, 194 King Street in Windsor: Hants County Commercial for sale (Annapolis Valley) : MLS®# 202509936

    172, 184, 194 King Street Hants County Windsor B0N 2T0
    Main Photo: 172, 184, 194 King Street in Windsor: Hants County Commercial for sale (Annapolis Valley)  : MLS®# 202509936
    $849,900
    Commercial
    Status:
    Active
    MLS® Num:
    202509936
    Major Bus.:
    Other
    Floor Area:
    10,442 sq. ft.
    This commercial property is located in the charming town of Windsor. The town offers a blend of historical significance, natural beauty, and community activities, making it an attractive place for residents and visitors alike. With over 22,000 SF of land this property has endless possibilities with the commericial/residence zoning, One building with over 7,500 SF of finished space as well as an attached garage, second building has over 3,200 SF of finished space, third space is a large parking lot (8,207 SF) perfect location for business or investment opportunity. Windsor provides a welcoming and vibrant environment - Whether you're interested in exploring its historical sites, enjoying its natural beauty, or participating in local events. Close to Highway 101, only 30 minutes to Halifax. More details
    Listed by RE/MAX Nova
    ZACH FRAIL
  • 1592 Crossley Court in Windsor: Hants County Multi-Family for sale (Annapolis Valley) : MLS®# 202518317

    1592 Crossley Court Hants County Windsor B0N 2T0
    Main Photo: 1592 Crossley Court in Windsor: Hants County Multi-Family for sale (Annapolis Valley)  : MLS®# 202518317
    $749,900
    Multi-Family
    Status:
    Active
    MLS® Num:
    202518317
    Welcome to this well-maintained fourplex offering a fantastic investment opportunity with future development potential in an ideal location in Windsor. This multi-unit features four spacious 3 bedroom units, each thoughtfully designed with a large open-concept living and dining area, roomy kitchens, and a full 4 piece bath. Each unit comes equipped with a fridge, stove, and its own private power meter and panel. Three of the four units are currently tenant-occupied, while the owner-occupied unit will be vacated upon possession, opening the door for increased rental income. Electric baseboard heating is in all units and ductless heat pumps already installed in three of them. Outdoors, residents can relax and unwind with deck access and a beautiful spacious lot. A large driveway with ample parking and municipal services add to the convenience. An additional building lot provides a great opportunity to expand your portfolio by constructing a second fourplex and doubling your potential income. Located just minutes from shopping, restaurants, schools, and all amenities. Excellent for commuting with easy access to Highway 101 and only 40 minutes from Halifax! More details
    Listed by Royal LePage Atlantic - Valley(Windsor) and Royal LePage Atlantic (Dartmouth)
    ZACH FRAIL
  • 8/10 Bailey Drive in Garlands Crossing: Hants County Residential for sale (Annapolis Valley) : MLS®# 202518409

    8/10 Bailey Drive Hants County Garlands Crossing B0N 2T0
    Main Photo: 8/10 Bailey Drive in Garlands Crossing: Hants County Residential for sale (Annapolis Valley)  : MLS®# 202518409
    $685,000
    Residential
    Status:
    Active
    MLS® Num:
    202518409
    Bedrooms:
    4
    Bathrooms:
    4
    Floor Area:
    2,416 sq. ft.
    Located in a fantastic family-friendly subdivision, this versatile 2 level home is packed with features, space, and income potential all in one. The main home features tiled foyer, living room, kitchen and dining as well as two pantry closets, and the 2 piece bath with laundry. The dedicated home office/den on the is level enjoys an electric fireplace. Upstairs, here are 3 bedrooms and a four piece bath. The Primary suite has a newly renovated ensuite. The lower level houses the utilities of the home as well as a separate 1 Bedroom apartment with it's own address making this a great space for in-laws, guests, older children, or rental income. The paved driveway leads to the detached, two car garage where you'll find space for a workshop or vehicle storage on one side, and synthetic ice tiles and boards on the other side. Behind the garage is the custom covered lounge complete with a WETT certified wood stove that helps extend the outdoor living season. The home has had energy conscious upgrades that include solar panels and an EV car charger. Walking distance to the High School and just minutes to the 100 series highway. Whether you're a growing family or an investor with taste, this home checks every box. Sellers can accommodate a quick closing so you can be settled before school starts. Book your private showing with your REALTOR today and experience elevated family living with built-in investment value. More details
    Listed by RE/MAX NOVA (Windsor)
    ZACH FRAIL
  • 55 Community Way in Garlands Crossing: Hants County Residential for sale (Annapolis Valley) : MLS®# 202516439

    55 Community Way Hants County Garlands Crossing B0N 2T0
    Main Photo: 55 Community Way in Garlands Crossing: Hants County Residential for sale (Annapolis Valley)  : MLS®# 202516439
    $669,000
    Residential
    Status:
    Active
    MLS® Num:
    202516439
    Bedrooms:
    2
    Bathrooms:
    2
    Floor Area:
    1,300 sq. ft.
    Impressive ! Pride in Ownership throughout in this spacious one level living in desirable Garlands Crossing, Windsor's 55 and over sr community. A lovely open layout boasts a gourmet kitchen with high end appliances, quartz hardtop, 9 foot island and a butlers pantry. Bright living and dining rooms, nicely accented with pot lights, leading to a wonderful screened sun room and adjacent patio deck. Primary bedroom features a beautiful ensuite and walk in closet. The second bedroom/guestroom is located conveniently near main bath. You'll love the laundry convenience here as well. Double garage, lots of storage, loaded with extras, new home warranty, nicely landscaped, 10 x 12 storage shed and also has a double paved driveway. Gorgeous view with Southwest Exposure to end your days. Also features an Irrigation System and air conditioning with the efficient ductless heat pumps. Five minutes to popular Avon Valley Golf Club, 20 minutes to the city. More details
    Listed by Steve Ingram Realty Ltd.
    ZACH FRAIL
  • 931 King Street in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202517119

    931 King Street Hants County Windsor B0N 2T0
    Main Photo: 931 King Street in Windsor: Hants County Residential for sale (Annapolis Valley)  : MLS®# 202517119
    $649,900
    Residential
    Status:
    Active
    MLS® Num:
    202517119
    Bedrooms:
    5
    Bathrooms:
    4
    Floor Area:
    3,807 sq. ft.
    Welcome to this beautifully appointed 5-bedroom, 4-bath executive home, nestled on a large, private lot surrounded by mature trees. This impressive property offers the perfect blend of elegance, comfort, and functionality - ideal for today’s modern family. Step inside to a spacious layout featuring a large eat-in kitchen with granite countertops, ample cabinetry, and room for family gatherings. The open-concept family room boasts a cozy fireplace, creating a warm and inviting space to relax or entertain. A generous dining room sets the stage for memorable dinners, while the formal living room has been thoughtfully converted into a stylish home office. Upstairs, you’ll find four well-sized bedrooms and the convenience of second-floor laundry. The primary suite is a peaceful retreat with a private ensuite and plenty of closet space. The fully finished walk-out basement offers incredible potential as a nanny or in-law suite, complete with expansive living space, a fifth generously sized bedroom, two-piece bathroom and its own private entry. Enjoy the outdoors in your own backyard oasis - complete with a firepit area, perfect for summer nights and year-round entertaining. Only steps to downtown Windsor and all amenities, minutes to Highway 101,a short drive to Ski-Martock, Avon Valley Golf Course and 45 minutes to downtown Halifax or Stanfield International Airport. This is a rare opportunity to own a luxurious, move-in-ready home on a premium lot. Don’t miss it! More details
    Listed by Royal LePage Atlantic - Valley(Windsor)
    ZACH FRAIL
  • 8 Elizabeth Avenue in Garlands Crossing: Hants County Residential for sale (Annapolis Valley) : MLS®# 202506756

    8 Elizabeth Avenue Hants County Garlands Crossing B0N 2T0
    Main Photo: 8 Elizabeth Avenue in Garlands Crossing: Hants County Residential for sale (Annapolis Valley)  : MLS®# 202506756
    $640,000
    Residential
    Status:
    Active
    MLS® Num:
    202506756
    Bedrooms:
    3
    Bathrooms:
    2
    Floor Area:
    1,543 sq. ft.
    Meet the “Gala” , one of the largest of the garden home collection with 3 bedrooms and 2 full bathrooms. This property shines with its desirable layout and design. The heart of this home is an attractive, light, and bright kitchen, fully equipped with ample cupboards and plenty of counter space with beautiful quartz countertops. The layout allows for everyday functionality overlooking the dining and living area. Transition seamlessly with the great flow to the primary suite, boasting a walk-in closet with ample storage and an ensuite featuring a sleek tiled walk-in shower and ensuite laundry. Two great-size bedrooms, beautiful covered back deck with a great sized yard. Heat pump for heating and cooling ,plus an attached garage. Lux Home Warranty included! Located moments to the golf course, the hospital, groceries, and Windsor, and only 30 minutes to Halifax and even less to the desirable Wolfville. Come check out this vibrant retirement community today! Book your viewing & start enjoying the Annapolis Valley retirement lifestyle. More details
    Listed by Engel & Volkers (Wolfville) and Engel & Volkers
    ZACH FRAIL
  • 30 Lakewood Drive Extension in Newport: Hants County Residential for sale (Annapolis Valley) : MLS®# 202515140

    30 Lakewood Drive Extension Hants County Newport B0N 2A0
    Main Photo: 30 Lakewood Drive Extension in Newport: Hants County Residential for sale (Annapolis Valley)  : MLS®# 202515140
    $619,900
    Residential
    Status:
    Active
    MLS® Num:
    202515140
    Bedrooms:
    3
    Bathrooms:
    3
    Floor Area:
    2,953 sq. ft.
    Welcome to your dream home at 30 Lakewood Drive Extension! This stunning property offers the perfect combination of elegance, functionality, and fun. Boasting 3 bedrooms, 3 bathrooms, and nearly 3,000 square feet of thoughtfully designed living space, this home is ready to welcome its new family. The main level features spacious, light-filled rooms with high-end finishes throughout, including custom trim work, hard surface countertops, and beautifully crafted showers. Upstairs, you’ll find three generously sized bedrooms, and the lower level offers the flexibility to create additional living or sleeping spaces with minimal effort. Step outside to your personal oasis on a large private lot. Whether you’re looking for relaxation or recreation, this property has it all. Take a dip in the luxurious 18x36 in-ground pool, unwind in the hot tub, or host unforgettable gatherings in the gazebo. Sports enthusiasts will love the basketball court, perfect for friendly games or practice sessions. Storage and workspace are no issue with an attached two-car garage and a massive detached 24x48 garage, providing ample room for vehicles, hobbies, or projects. This home truly offers something for everyone—from cozy family evenings by the wood stove to lively summer pool parties. Don’t miss your chance to make 30 Lakewood Drive Extension your forever home. Schedule your viewing today! More details
    Listed by Keller Williams Select Realty
    ZACH FRAIL
  • 542 King Street in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202518872

    542 King Street Hants County Windsor B0N 2T0
    Main Photo: 542 King Street in Windsor: Hants County Residential for sale (Annapolis Valley)  : MLS®# 202518872
    $619,900
    Residential
    Status:
    Active
    MLS® Num:
    202518872
    Bedrooms:
    4
    Bathrooms:
    2
    Floor Area:
    2,700 sq. ft.
    Welcome to 542 King Street in Windsor- a perfect fusion of timeless Victorian charm and modern comfort! Set on a spacious and private lot in a quiet, walkable neighborhood, this 2.5-storey home captures attention with its classic four-square design, striking curb appeal and a generous covered front porch ideal for morning coffees or evening unwinding. The location is unbeatable - park the car and stroll to grocery stores, aquatic and recreation centers, the library, Mermaid Theatre, Gerrish & Gray Café, Bedard Bakery, Kings-Edgehill School, and many other nearby amenities. Inside, you’re welcomed by soaring 10-foot ceilings and an elegant staircase featuring the original newel post; all complemented by tasteful updates that add sophistication without compromising the home’s character. Over the past two years, the current owners have thoughtfully modernized the home with a complete overhaul of the heating system, basement spray foam insulation, and all new hot and cold water service. A new sewer line with a backflow prevention valve adds peace of mind, while updated designer lighting, fresh paint, new wallpaper, and custom window treatments elevate the overall aesthetic. The home is outfitted with heat pumps in almost every room, providing total climate control for year-round comfort and efficiency. Additional enhancements include newer Kohler windows, updated electrical with a GenerLink panel and plug-in for a portable generator, and refreshed bathrooms. At the back of the home, a practical rear mudroom offers custom-built storage lockers and a walk-in coat closet — perfect for everyday organization. Every improvement has been made with care, ensuring that the home’s original charm remains at the forefront while meeting the needs of modern living. Warmth and character radiate from every corner, making this a truly special generational home that must be seen to be fully appreciated. More details
    Listed by Viewpoint Realty Services Inc. and ViewPoint Realty Services Inc.(Greenwood)
    ZACH FRAIL
  • 496 Albert Street in Windsor: Hants County Residential for sale (Annapolis Valley) : MLS®# 202513852

    496 Albert Street Hants County Windsor B0N 2T0
    Main Photo: 496 Albert Street in Windsor: Hants County Residential for sale (Annapolis Valley)  : MLS®# 202513852
    $599,000
    Residential
    Status:
    Active
    MLS® Num:
    202513852
    Bedrooms:
    4
    Bathrooms:
    4
    Floor Area:
    3,309 sq. ft.
    Standing tall and elevated above Albert Street - 496 is a stately presence to behold. With its luscious gardens, oversized lots and ample sized updated home - it successfully commands attention. The paved circular driveway reminds one of the luxury and elegance of days gone by. The 3309 square feet encompasses 4 bedrooms, and 3 baths. The primary bedroom is enormous with a fully updated ensuite, walk-in closet, and Juliette balcony. Heat pumps keep you temperate in all weather. There are so many common living spaces for a large family - a huge living room on the main floor, two dining rooms, large foyer, office, basement rec room to name a few. Everywhere you sit you feel the beautifully preserved history entangled lovingly with tasteful modern updates. There are two PIDS included in this sale; the outdoor spaces are as numerous as the indoor spaces. This oasis is well placed off of the main roads but is proximal to all that gentrified Windsor has to offer - Municipal services, restaurants, boutiques, markets and more. This home must be seen to be appreciated - it is the perfect blend of character and modern updates and high end finishes! Home found...Come take a look for yourself, see how an in-town oasis can feel! More details
    Listed by Viewpoint Realty Services Inc.
    ZACH FRAIL
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Data was last updated July 30, 2025 at 11:20 AM (UTC)