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$2,950,000
3 Beds ⋅ 4 Baths ⋅ 202618029 MLS
Perched atop Chester's coveted peninsula, "Calder Stones" is an architecturally distinctive 2.5-storey coastal home designed by noted architect Syd Dumaresq in 1987, commanding sweeping east-facing views over Chester Harbour and capturing sunrise over the water along with long evening sun on the wraparound deck. Set on nearly an acre of private, landscaped grounds, the home overlooks the sailboats that have made Chester internationally famous, with views of the Golf Club, Meisners Island and the Aspotogan Peninsula, while the Yacht Club, Freda's Beach and village shops and restaurants are just moments away. A gracious foyer welcomes you into a light-filled interior of warm-toned softwood floors, built-in window seats, wainscotting and two oak staircases, with water views unfolding from nearly every room. The eat-in kitchen, with a large island and ample cupboard space, flows onto the rear deck's sun and shaded retreats. The living room is anchored by a wood-burning stone fireplace with room for formal dining, while the four-seasons room with vaulted ceilings opens onto the deck for effortless indoor-outdoor living. Upstairs, the primary suite offers its own fireplace, walk-in closet and ensuite, plus two further bedrooms, all overlooking the harbour. Main-floor laundry and a powder room complete the main level, while the partially finished lower level, with walkout to the rear yard, features a rec room and full bath with walk-in shower. Many windows and patio doors have been updated, and an expansive attic offers further storage or development potential. Cape Cod-style dormers lend old-world character, while the durable metal roof offers peace of mind against coastal storms. Central AC via a ducted heat pump, 200-amp service and 13kW generator ensure comfort year-round, and a detached double garage completes the property. Offered fully furnished, this is a rare, turnkey opportunity to own one of Chester's most prestigious residential vantage points.

20 Fredas Point Extension, Chester
$2,950,000
202617915 MLS
Visit REALTOR® website for additional information. Dreaming of owning property in Canada? Chester, Nova Scotia offers international buyers a rare opportunity in one of Atlantic Canada's most desirable coastal communities. With a population under 10,000, Chester remains exempt from Canada's foreign buyer ban until 2027, allowing eligible foreign nationals to purchase Canadian real estate. Just 40 minutes from Halifax (less than 30 minutes with the new Highway 3 twinning), this exceptional dual-property estate combines two upgraded homes offering over 6,000 sq. ft. of living space with 7 bedrooms and 7 bathrooms, all within walking distance of Chester's waterfront and village. 123 Duke Street is a beautifully restored heritage home, formerly the Casa Blanca Inn. It is currently configured as two separate residences but can easily become one grand home. It includes a self-contained 2-bedroom garden suite plus an executive upper residence with a luxurious primary suite, spa-inspired ensuite, library, gym, and spacious living areas. 121 Duke Street is a fully furnished 3-bedroom, 2-bath home on a private lot, ideal for vacation rentals or guests. Highlights include a 60-foot saltwater lap pool, multiple decks, propane fireplace, heat pumps, and games room. Both homes feature a deep drilled well, advanced drainage, Cat 6 Ethernet, buried electrical service, and a permeable driveway. Elevated above the flood zone, they offer water views and include a registered mooring in Chester's protected Front Harbour. Walk to the Chester Yacht Club, cafés, restaurants, shops, the Playhouse, and waterfront. Chester Golf Club and Sensea Nordic Spa are just minutes away. Offering proven rental income, premium infrastructure, and exceptional flexibility, this turnkey property is ideal as a luxury family compound, multi-generational retreat, or investment in one of Atlantic Canada's premier seaside communities.

121 & 123 Duke Street, Chester
$10,000,000
10 Beds ⋅ 9 Baths ⋅ 202615433 MLS
Chester – Nova Scotia’s most prestigious and storied village. Welcome to this all-encompassing, multi-generational retreat/estate; an impressive private “end of the road” 19 acres on four PID’s of ocean panorama, looking down from a hilltop on the village of Chester, the back harbour, and the islands of Mahone Bay. With over 6000 square feet of architecturally brilliant living space, and another 1500 feet of storage, spread across three gorgeous structures, step inside to discover generously proportioned principal rooms, soaring ceilings, and an effortless flow ideal for both comfortable family living and large-scale entertaining, along with sweeping views down cascading lawns to the pool and ocean beyond. Anchoring the estate is the ground floor, open kitchen dining area with adjacent living and bunk rooms. The kitchen is a masterfully designed galley arrangement of antique style cabinetry, concrete countertops, and integrated panel appliances (2 Liebherr fridge/freezers, and two Miele dishwashers). The island, featuring a 48” Viking dual-gas range and bar sink, opens the space seamlessly, with vaulted ceiling enveloping the dining room, which sports in turn hand-hewn beams and ceiling dormer windows. The dining table seats fourteen, eminently suited to festive gatherings. There are many thoughtful features, such as wide-plank walnut flooring, built-in pantry and storage spaces, and shiplap wall panelling. A further vaulted ceiling accentuates the grandeur of the living room, along with expansive two-story windows and a wood-burning fireplace. All three living, kitchen and dining rooms have multiple french door access points to patios, creating a seamless transition to the elegant outdoors. As to the young, sleeping quarters accommodate no less than eight in the bunk room, alongside a triple-sink bathroom with tiled shower and a line of closets for sleepover guests.

100 Walker Cut, Chester
$1,249,000
202614937 MLS
Rarely offered waterfront land in the village of Chester with towering elevated south easterly views of Mahone Bay Islands (Saddle, Graves, Mountain and Tancook) and the Atlantic Ocean beyond. Featuring approximately 150 feet of frontage on four acres and a mix of pastureland and wooded forest. A 200-foot break wall/wharf with an additional 50-foot wharf (right angle coverage at the end), provides an excellent deep water/safe harbour docking for a large vessel. For a potential purchase, this parcel will be under a subdivision process to be completed before the closing date. The adjacent estate is also for sale at 25 Chester Shore Road, if a larger compound is in consideration. The location is ideally suited for those that wish to live within close proximity to all that the village of Chester has to offer including fine art at the Chester Art Centre, theatre at the Chester Play House, dockside seafood chowder at the Rope Loft, latte’s at the Kiwi Café, fine dining at the Sunroom, sailing at the Chester Yacht Club, tall tales at the Fo’c’sle Tavern and sports at the Chester Tennis & Golf Clubs.

3 Chester Shore Road, Chester
$1,450,000
3 Beds ⋅ 2 Baths ⋅ 202606210 MLS
Coastal Elegance Meets Modern Comfort on Chester's Coveted Back Harbour. Experience the quintessential luxury lifestyle in this beautiful, turnkey waterfront property. Boasting great elevation from the shore, this stunning 2,116 sq. ft. Cape Cod home sits on a quiet dead-end street just a five-minute walk from the central village. The property has undergone extensive renovations to seamlessly blend classic maritime charm with exceptional modern efficiency. With 75 feet of frontage on the highly sought-after Back Harbour, the exterior is an absolute entertainer's dream. Enjoy immediate water access with six feet at low tide, a private wharf featuring EZ Dock floats, and a dedicated kayak launch. The grounds are a masterpiece of landscaping, featuring a lovely stone patio with a fire-pit and al fresco dining area, a new composite deck with elevated views, mature perennial gardens, raised vegetable beds, and a professional greenhouse. The main floor invites you inside with a beautifully appointed living and dining area, showcasing refinished original hardwood floors that flow to a refreshed country kitchen that shines with high-end appliances and updated finishes. Step into the spectacular three-season room, newly added in 2022, to enjoy your morning coffee by the propane fireplace while soaking in views of the lush yard and harbour below. Peace of mind comes standard with significant upgrades, new 2024 windows, dual heat pump systems, and fully converted high-efficiency electric boiler system. Just a short stroll from the yacht club, playhouse, and local shops, this impeccable property is ready for its next chapter.

103 Granite Street, Chester
$1,795,000
4 Beds ⋅ 5 Baths ⋅ 202515495 MLS
Visit REALTOR® website for additional information. Once home to the renowned Casa Blanca Inn, this historic Chester property blends timeless elegance with modern comfort. Thoughtfully reimagined, it offers flexibility as a private residence, boutique rental, or event space. The main level features a refined 2-bedroom suite with over 1,700 sq ft, while the upper 2-3 bedroom flat spans more than 2,500 sq ft-ideal for guests or entertaining. Just steps from the ocean and Chester's vibrant village core, this one-of-a-kind home is a rare chance to own a piece of local history with exceptional lifestyle and income potential.

123 Duke Street, Chester
$1,295,000
3 Beds ⋅ 2 Baths ⋅ 202508297 MLS
Visit REALTOR® website for additional information. Set on a private lot, this home is a fully furnished 3-bedroom, 2-bath home with stylish interior & generous outdoor living. Ideal as a getaway, full-time home, or income property. Just a short walk to downtown Chester to the yacht club & minutes from Sensea Nordic Spa. Features include a 60-foot saltwater lap pool, lush landscaping, ambient lighting, new heat pumps, a propane fireplace & designer finishes. A converted family room adds flexible space & the EcoRaster driveway provides ample, low-maintenance parking year-round. Chester offers a vibrant, year-round lifestyle with fine art, theatre, fresh seafood, artisan cafés, sailing, golf, tennis, pickleball & lively pubs. With a population under 10,000, it's exempt from Canada's foreign buyer ban-one of the few places U.S. buyers can still purchase property until 2027.

121 Duke Street, Chester