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Browse All Chester NS Properties for Sale

$549,000
2 Beds 3 Baths 202622410 MLS
CAREFREE CONDO LIVING, CHESTER. Enjoy the flexibility, comfort, and space of a detached home without any of the maintenance burdens. This meticulously maintained bungalow-style townhome in Chandler’s Cove offers effortless, one-level main living paired with a fully finished lower-level guest retreat. The light-filled main floor features an open-concept layout with gleaming hardwood floors, updated lighting, central vacuum, an efficient kitchen, and a primary suite with a private ensuite. A versatile den serves as an ideal home office or second main-floor bedroom, accompanied by a guest bathroom. Off the principal living area, step out onto a sunny, spacious back deck—perfect for outdoor dining or evening relaxation. Downstairs, the fully finished lower level provides privacy for visiting family and friends, complete with a family/media room, a third bedroom, and a private ensuite bath. Additional features include a large lower-level laundry room, plus main-floor plumbing in place should you prefer main-level laundry facilities. Beyond your doorstep, embrace everything Chester has to offer: an active community centre within Chandler's Cove Village, world-class golf, sailing at the Chester Yacht Club, live theatre, tennis, curling, the Lido outdoor saltwater pool, local cafes, fine dining, and the scenic Chester Connection Trail for hiking and cycling. A perfect balance of community, convenience, and luxury.

21 Millennium Drive, Chester

$779,900
4 Beds 4 Baths 202621609 MLS
Riverfront oasis just outside the charming town of Chester. This 4-bedroom home sits on 3.71 acres bordered by a flowing river, with income potential and space for many interests. The detached heated and wired garage holds all the toys and includes a legal apartment above — currently rented, and equally suited to an artist's or writer's studio. The main level is a showpiece: vaulted ceilings, a soaring wall of windows, and an open-concept layout with a beautiful kitchen overlooking the living area. A propane stove anchors the space, and sunlight pours in across views of the property, pool and river. Two bedrooms and a full bath complete this level — ideal for guests or a home office. The primary suite occupies the upper level with its own private bath. The walkout lower level is currently an in-law suite with a separate entrance, kitchen, living room and utility/storage area — a very functional space with many possibilities. A large wrap-around deck overlooks the private grounds: meandering river, established gardens, chicken coop, pool, surrounding trees and glimpses of Stanford Lake. Two driveways offer parking for multiple vehicles plus room for additional outbuildings. Minutes to downtown Chester — groceries, hardware, NLSC, marina, yacht club, Tancook ferry, community pool, theatre, schools, shopping and dining. SenSea Nordic Spa is just down the road. Downtown Halifax is 45 minutes away.

182 Stanford Lake Road, Chester

$498,900
3 Beds 2 Baths 202621205 MLS
Welcome to 3912 North Street, perfectly situated in the heart of charming Chester! This 3-bedroom, 2-bathroom bungalow has been extensively renovated, featuring newer siding, windows, doors, heat pumps, updated flooring, fresh paint, a modern kitchen, and much more. Step inside to a generous foyer with ample room for family gear before flowing into the bright, open-concept living, dining, and kitchen area. The kitchen is designed for entertaining, complete with extensive cabinetry, a large breakfast bar overhang, and patio doors opening to a fully fenced backyard with a stone patio—perfect for summer barbecues and gatherings. Two spacious bedrooms and a full bathroom round out the well-appointed main floor. The fully renovated lower level boasts a massive primary suite with private walkout access, a large family room, and a stylish combined bath/laundry with a relaxing soaker tub (already roughed-in for a shower). The versatile layout offers exceptional flexibility: reconfigure the main level to create an additional bedroom, or capitalize on the private walkout entrance to explore secondary suite potential. Enjoy unbeatable coastal living—walk to local grocery stores and dining, or take a quick drive to the Chester Playhouse, dockside meals at the Rope Loft, morning coffee at the Kiwi Café, sailing at the Chester Yacht Club, and rounds at the Chester Golf and Tennis Clubs. Exceptional value in a premier location—book your private viewing today!

3912 North Street, Chester

$599,900
3 Beds 3 Baths 202618268 MLS
Chester has always been one of those places people dream about calling home. The sailing, the cafés, the small-town charm, the coastline... it's easy to see why. But finding a property that gives you all of that without being right in the middle of the village? That's where this one stands apart. Set on the shores of Stanford Lake, just beyond the village limits, you'll enjoy a little more space, a day in your kayak or a little swim, and the convenience of being only minutes from everything Chester is known for. Need to head to Halifax? Highway 103 is just around the corner, making the commute surprisingly easy. This classic Cape Cod has all the right ingredients, rich hardwood floors, a welcoming propane fireplace, a formal dining room, and a comfortable family room, walk-in pantry and main floor laundry. Upstairs, the primary suite offers a walk-in closet and ensuite complete with a soaker tub, a sitting area that could double as office space, two additional bedrooms and another full bath. Then there's the basement! With its walk-out design and impressive amount of space, it could become the recreation room you've always wanted, a fourth bedroom, a home office, or even a secondary suite for extended family. Outside is every bit as inviting. The expansive back deck, complete with awning, the lakeside flagstone patio and hammock spot are easily spaces to fall in love with. The paved driveway and direct-transfer generator provide peace of mind, and the garden shed has all the makings of an incredible bunkie, studio, or hobby space. If you've been searching for a home that feels established, exceptionally cared for, and perfectly positioned to enjoy everything Chester has to offer without giving up your own piece of quiet, this one deserves your attention.

6 Stanford Lake Road, 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

$425,000
2 Beds 2 Baths 202612046 MLS
Located in the thriving seaside community of Chester, this newly rezoned residential property offers flexibility, charm, and exciting potential in one of the South Shore’s most desirable coastal markets. Strategically positioned with direct access to Highway 3 and close to marinas, boutiques, cafés, and dining, this unique property blends convenience with lifestyle appeal. An additional 7,200 sq. ft. vacant lot is included, providing extra outdoor space and future possibilities. Recently updated with new siding, a new metal roof and additional improvements, the home has been thoughtfully reimagined into a functional two-bedroom layout with flexibility for a variety of living arrangements. Heat pumps and electric baseboards ensure year round comfort. The main level features warm softwood floors, a stylish feature tile wall with built-in shelving, a spacious bedroom, full 4-piece bath, and in-unit laundry. Upstairs, vaulted ceilings with modern pot lighting create a bright and inviting second living space complete with an additional bedroom area and half bath. A separate entrance and separate electrical panel upstairs offer added versatility for buyers seeking space for extended family, guests, a home-based business, studio, rental potential or future customization potential. Whether you are searching for a year-round residence, weekend getaway, investment opportunity, or a property with flexible use options, this Chester home offers outstanding value in a high-demand coastal community. With residential zoning now in place and an additional lot included, this is a rare opportunity to secure space, updates, and long-term potential in a location people continue to fall in love with.

3760 Highway 3, Chester

$725,000
2 Beds 3 Baths 202610890 MLS
This masterfully crafted new-construction custom home is perfectly situated in the vibrant heart of Chester, Nova Scotia. Offering a seamless blend of classic South Shore architecture and modern luxury, you are a short stroll from the renowned Chester Yacht Club, Playhouse, fine dining, charming local shops, cafés and also minutes from the Chester Golf Course. Upon entering you are greeted by soaring nine-foot ceilings and expansive windows that flood the open-plan main floor with natural light. The gourmet kitchen is a chef's dream, featuring custom cabinetry, quartz countertops, high-end appliances, and a propane range. Cozy in-floor heating and a beautiful paver-stone patio that wraps around the side and back complete the main level. Thoughtful custom details continue throughout the second level, where vaulted ceilings and a bright landing with a wall of windows separate the two bedrooms. Each room is well-appointed - one facing south, the other north - and both showcase vaulted shiplap ceilings, luxurious ensuite bathrooms with custom tile showers and walk-in closets with elegant built-in shelving. Modern essentials including a fully ducted heat pump for year-round climate control and on-demand hot water ensure a high-performance, low-maintenance lifestyle. This home represents a rare opportunity to enjoy the timeless charm of village living in a residence built to the highest standards of modern quality and comfort.

69 Union Street, 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

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