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$2,200,000
3 Beds ⋅ 4 Baths ⋅ 202620300 MLS
An exceptional opportunity awaits in the heart of the Village of Chester with this rare and remarkably private 1.6-acre property. Showcasing an expansive 269 feet of road frontage, the lawn slopes gently toward the street, offering potential water views and incredible space to breathe. Developers and visionaries will appreciate the favorable R2 zoning, which opens the door for potential lot subdivision (buyer to verify details with the Municipality of Chester). Perched at the high point of the land sits a well-maintained, three bedroom plus den, four-bathroom bungalow featuring a built-in double garage. Inside, you will find a bright, thoughtful layout filled with natural light, wide windows, and classic hardwood floors. Whether you choose to renovate the existing structure or construct your tailored architectural masterpiece, the setting provides an unbeatable backdrop. Location is everything, and this property places you just steps from vibrant village amenities, fine dining, local art galleries, the Chester Playhouse, and the Chester Yacht Club. Offered as an estate sale with limited background information available, this occupied residence presents endless potential in one of the East Coast's most desirable coastal communities. No Disclosure Statement with this Estate Sale

121 Victoria Street, Chester
$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. 7 Bed | 7 Bath | 6,058 sq ft | 0.39 ac | Outdoor Pool | Registered Mooring A rare dual-property estate in the heart of Chester village, combining two fully upgraded residences into one exceptional compound—ideal as a family retreat, multi-generational home, or turnkey vacation-rental operation. Over 6,000 sq ft of refined living, 7 bedrooms and 7 bathrooms, all within walking distance of the village centre, waterfront, and Chester Yacht Club. Just 40 minutes to Halifax (under 30 with the new Highway 3 twinning). 123 Duke St – Heritage residence (former Casa Blanca Inn): Currently two separate suites, easily converted to one grand home. Lower garden suite offers 1,700 sq ft / 2 bedrooms, ideal for rental or guests. Upper executive suite spans 2,500+ sq ft with a spacious master, spa-like ensuite, private gym, library, and living areas. 121 Duke St – Contemporary residence: 1,800 sq ft, 3 bed / 2 bath on a private flag lot. Fully furnished and rental-ready. Features a 60-ft saltwater lap pool (new liner, automatic cover), multiple decks, new heat pumps, propane fireplace, and a games room. Built for peace of mind: Deep drilled well with automatic water management, advanced sump/drainage systems (basements stayed dry through recent area flooding), buried electrical, Cat 6 wiring, and permeable Ecoraster driveway. Elevated water views, safely above the flood zone. Registered mooring buoy in protected Front Harbour included; professional property management in place. Minutes to Chester Golf Club, Sensea Nordic Spa, dining, the Playhouse, and trails. Showings require 48 hours' notice.

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
$1,190,000
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
$1,795,000
4 Beds ⋅ 5 Baths ⋅ 202515495 MLS
Visit REALTOR® website for additional information. Welcome to 123 Duke Street — a captivating property steeped in history and brimming with opportunity, nestled in the heart of Chester Village. Once home to the renowned Casa Blanca Inn, this distinguished residence masterfully blends the grandeur of its storied past with refined modern luxury. Formerly a celebrated inn known for its warmth and hospitality, this unique property has been thoughtfully reimagined as a stunning private residence or income-generating retreat. With its timeless architecture and elegant design, it offers the perfect venue for corporate events, weddings, or as a lucrative addition to your rental portfolio. Step inside to discover an ambiance where old-world charm meets contemporary comfort. The main level reveals a sophisticated 2-bedroom haven spanning over 1,700 square feet, featuring generous living spaces and tasteful finishes that pay homage to the home’s heritage. Upstairs, the expansive 2–3 bedroom flat boasts more than 2,500 square feet, offering exceptional flexibility—ideal as a luxurious residence, guest quarters, or an event showcase. Beyond its impressive interiors, the property is ideally situated just steps from the ocean in the heart of Chester—a picturesque coastal community known for its scenic harbor, vibrant cultural life, and charming boutiques. Whether you're strolling the historic waterfront, enjoying world-class sailing, or dining at one of the village’s celebrated eateries, everything you need is at your doorstep. 123 Duke Street is more than just a home—it's a rare opportunity to own a piece of Chester’s rich history, while embracing a lifestyle of comfort, sophistication, and coastal charm. Whether you envision a private sanctuary, a thriving rental, or a boutique event space, this remarkable property offers endless potential

123 Duke Street, Chester
$1,295,000
3 Beds ⋅ 2 Baths ⋅ 202508297 MLS
Visit REALTOR® website for additional information. Welcome to 121 Duke Street, a beautifully designed and fully furnished 3-bedroom, 2-bathroom home in the heart of Chester, one of Nova Scotia's most sought-after seaside villages, just 40 minutes from Halifax. Set on a private 8,238 sq ft flag lot, this 1,808 sq ft residence offers refined coastal living with strong income potential, already configured for both long-term and vacation rental use. Inside, enjoy modern comfort throughout, including new heat pumps, a propane fireplace, and designer kitchen and bath finishes. A spacious converted family room provides versatile additional living space. The turnkey offering includes appliances (refrigerator, microwave/hood combo, dishwasher, electric range, washer and dryer), with furnishings negotiable, along with a slate pool table and table tennis setup. Outdoors, the property features a 60-foot saltwater lap pool, a pool house, mature landscaping, ambient yard lighting, and a low-maintenance permeable EcoRaster driveway with ample parking and a 2-car carport. Ideally located a 10-minute walk from downtown Chester and the Chester Yacht Club, a 3-minute drive to Chester Golf Club, and 5 minutes from Sensea Nordic Spa. Enjoy year-round village amenities including the Chester Art Centre, Chester Playhouse, waterfront dining, and an active tennis and pickleball community. A rare opportunity for a seasonal getaway, full-time residence, or investment property. 48 hours' notice required for showings as the property is tenanted.

121 Duke Street, Chester