Chester Real Estate | Chester Homes for Sale

202618645 MLS

A very private interior 1.75-acre lot accessible from the Fairway Lane cul-de-sac. Of the five lots, this is the only one not bordering the Chester Golf Course/road. If you love natural surroundings but want to be close to the village, this location is ideal. It is an easy walk to NS’s most walkable village. The distance is less than 2 KMs to Chester’s downtown. A subdivision survey with perc testing sites is available, showing a total of five available lots with pricing. A drilled or dug well would be the responsibility of the new owner and electrical utility will be supplied to the lot line by the vendor. Also available are the potential restrictive covenants detail, pending legal review. Shared access for the lots will be from Fairway Lane the cul-de-sac off Golf Course Road which is being levelled through Dexter Construction. A shared road agreement will be in place once the first lot has been sold. Come celebrate life in Chester where everything is possible, including fine art at Going Coastal, theatre at the Chester Playhouse, dockside seafood chowder at the Rope Loft, lattes at the Kiwi Café, fine dining at the Sunroom, sailing at the Chester Yacht Club, tall tales at the Focsle Tavern and sports at the Chester Tennis & Golf Clubs.

Fairway Lane, Chester

$629,900

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

$164,900

202618241 MLS

Oceanfront Opportunity in Chester! Build your dream coastal retreat on this exceptional 10,000 sq. ft. oceanfront lot offering 104 feet of direct Atlantic Ocean frontage. Nestled in a protected cove, this level property has already been prepared for construction, making it the perfect canvas for your future home or cottage. The lot has an approved septic system, allowing you to move forward with confidence. Enjoy breathtaking water views, easy shoreline access, and the peace and privacy of one of Nova Scotia’s most desirable coastal communities, all while being just minutes from the amenities, marina, and charm of Chester. As an added bonus, the seller is willing to include the existing motorhome with the property for an increased purchase price, providing an ideal place to stay while you build or a turnkey seasonal getaway. This is a rare opportunity to own a ready-to-build waterfront property in one of the South Shore’s most sought-after locations.

Goat Lake Road Unit Lot, Chester

$239,000

202618051 MLS

A premier building lot just shy of an acre on Golf Course Road, this corner piece also has access from the Fairway Lane cul-de-sac. Adjacent to the Chester Golf Club, it is also an easy walk to the village of Chester. A subdivision survey with perc testing sites is available, showing a total of five available lots with pricing. A drilled or dug well would be the responsibility of the new owner and electrical utility will be supplied to the lot line by the vendor. Also available is a potential restrictive covenants detail, pending legal review. Shared access for the lots will be from Fairway Lane the cul-de-sac off Golf Course Road which is being levelled through Dexter Construction. A shared road agreement will be in place once the first lot has been sold. Come celebrate life in Chester where everything is possible, including fine art at Going Coastal, theatre at the Chester Playhouse, dockside seafood chowder at the Rope Loft, lattes at the Kiwi Café, fine dining at the Sunroom, sailing at the Chester Yacht Club, tall tales at the Focsle Tavern and sports at the Chester Tennis & Golf Clubs.

Golf Course Road Unit Lot 5, Chester

$399,000

202618045 MLS

A premier building lot spanning 1.8 acres with direct frontage on the 15th fairway of the Chester Golf Club. This corner piece has access from Fairway Lane cul-de-sac, which runs north from Golf Course Road. An easy walk to the village of Chester so you can clock in your daily 10,000 steps! A subdivision survey with perc testing sites is available, showing a total of five available lots with pricing. A drilled or dug well would be the responsibility of the new owner and electrical utility will be supplied to the lot line by the vendor. Also available is a potential restrictive covenants detail, pending legal review. Shared access for the lots will be from Fairway Lane the cul-de-sac off Golf Course Road which is being levelled through Dexter Construction. A shared road agreement will be in place once the first lot has been sold. Come celebrate life in Chester where everything is possible, including fine art at Going Coastal, theatre at the Chester Playhouse, dockside seafood chowder at the Rope Loft, lattes at the Kiwi Café, fine dining at the Sunroom, sailing at the Chester Yacht Club, tall tales at the Focsle Tavern and sports at the Chester Tennis & Golf Clubs.

Fairway Lane Unit Lot 4, 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. 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

$689,000

4 Beds ⋅ 3 Baths ⋅ 202617913 MLS

Nestled in the quiet residential development of Seawinds, the quality of construction is undeniable in this German-built custom home. Located on a peaceful, paved circular road with friendly neighbours, it offers a safe environment for children and pets. You are within easy walking distance to downtown Chester, the scenic Chester Connection Trail, and the local Farmer’s Market. Truly a must-see feature, the home showcases solid mahogany windows equipped with integrated, metal retractable storm shutters, a beautiful custom beveled glass and mahogany entry door, and extra thick oak interior doors. There are 9 foot ceilings on both levels, crown mouldings, inviting dining / living room with a propane fireplace focal point. The beautifully updated kitchen features modern cabinets, new countertops, a stylish backsplash, and top-of-the-line appliances. The layout includes two spacious main-floor bedrooms, each featuring its own private ensuite bathroom. The spacious lower level features 9-foot ceilings and has been freshly painted from top to bottom. All old carpeting was replaced with high-end maple engineered hardwood flooring. This level includes a comfortable family room, two additional bedrooms, a third bathroom, and a laundry storage room. A separate walk-out entrance leads to a spacious private deck ideal for entertaining. This level could easily be converted into an independent granny suite or rental unit with the simple addition of a kitchen. The property sits on a beautifully landscaped, private lot. Exterior features include timeless wood siding, a durable newer metal roof, two large decks for outdoor entertaining, a storage shed, and a portable shelter that stays with the property. Recent mechanical upgrades include three ductless heat pumps for highly efficient heating and cooling, a brand-new water conditioner for the high-yield drilled well, and upgraded copper interior plumbing lines. Feature sheet is available.

25 Eastwind Drive, Chester

$524,900

4 Beds ⋅ 2 Baths ⋅ 202616657 MLS

Step into timeless charm with this well-cared for century old two-storey farmhouse in the desirable South Shore community of Chester Basin. Offering over 1,600 sq. ft. of living space on just under an acre, this character-filled home is surrounded by mature trees and a private backyard, creating a peaceful rural setting. Inside, you’ll find soaring 8-foot ceilings, abundant natural light, and original hardwood floors throughout much of the home. While the hardwood would benefit from refinishing, it holds excellent potential to be beautifully restored and further enhance the home’s original character. A beautiful original wood staircase leads to four bedrooms upstairs, a full bath, and a walk-up attic, while a convenient powder room is located on the main level. The kitchen offers generous storage and a functional layout ideal for everyday living and entertaining. Adjacent to it, the formal dining area features a built-in wood cabinet that adds both charm and additional storage, while the space itself provides flexibility for a fifth bedroom, home office, den, or main-floor laundry for convenient one-level living. Comfort is provided year-round with a ductless heat pump, electric baseboards, as well as a wood furnace that adds cozy farmhouse warmth. A standout feature is the expansive covered front porch, ideal for relaxing or entertaining while enjoying the peaceful surroundings. The property also includes a paved driveway, detached garage, and storage shed. Ideally located just steps from the ocean, Rails to Trails, and Croft Road playground, this home is perfect for outdoor enthusiasts. Walking distance to all amenities in Chester Basin, including bank, pharmacy, Legion, church, post office, restaurant, convenience store with gas, café, and take-out. Less than 10 minutes to the seaside village of Chester and 45 minutes to downtown Halifax.

63 Croft Road, Chester Basin

$699,000

3 Beds ⋅ 2 Baths ⋅ 202616126 MLS

Welcome to easy, one-level living in the heart of Chester. Perfect for retirees, downsizers, or anyone looking to simplify without sacrificing location, this well-maintained 3-bedroom, 1.5-bath home sits on a beautiful level corner lot with no basement to worry about and a dependable well that has never run dry. An efficient heat pump provides economical year-round comfort, while the propane fireplace creates a warm, inviting living space. The propane stove is another welcome feature for those who enjoy cooking. One of the property’s most unique features is its incredible setting. Directly across the street is Lordly Park, creating the feeling of an expansive park-like front yard without the maintenance. Enjoy mature green space and open lawns that the village maintains, making it feel like a natural extension of your own property. From here, it’s an easy stroll to downtown Chester, local shops, cafés, galleries, the Lido, Playhouse, and the Chester Yacht Club, allowing you to leave the car at home and enjoy everything this vibrant seaside community has to offer. Whether you’re relaxing on the property, throwing a ball in the park, or meeting friends downtown, this home offers a lifestyle that’s becoming increasingly hard to find.

87 Prince Street, Chester

$225,000

202616074 MLS

Build your dream home in one of Nova Scotia’s most desirable seaside communities! This exceptional building lot on Riverside Cove in Chester offers an incredible head start, with a drilled well, septic system, poured concrete foundation, and detached single garage already in place. The property also includes house plans, making it even easier to bring your vision to life. Enjoy beautiful views of Hennigar Lake while being just minutes from the charming village of Chester, renowned for its sailing, golf, beaches, boutiques, restaurants, and vibrant summer atmosphere. Whether you’re looking for a year-round residence or the ultimate seasonal retreat, this is a rare opportunity to build in a location that’s truly synonymous with Nova Scotia summer living. Your dream home starts here!

27 Riverside Cove, Chester

$199,900

202615496 MLS

Set in the coastal community of Chester Basin, this vacant lot offers the opportunity to create a home or seasonal escape in a peaceful South Shore setting. Surrounded by natural beauty and located near Chester, Mahone Bay, local marinas, golf, dining, and everyday conveniences, the property blends privacy with easy access to some of the area’s most loved amenities. As part of the Skipper Hill community, the lot includes access to the Skipper Hill Wharf, adding extra appeal for buyers who value time near the water, boating, or simply enjoying the coastal lifestyle. With Halifax approximately 40 minutes away, this location is well suited for those looking to build in a quiet seaside area without feeling disconnected.

Swallow Point Road Skipper Hill Estates Unit Lot 2, Chester Basin

$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

$347,000

202614803 MLS

Located in the desirable community of Chester Basin this sunny lot enjoys 0.73 acres and beautiful elevated ocean views. Great sought-after southern exposure ensures all day sun, and with a cleared site ready to break ground, this lot has everything in place for you to start building your dream property. Many charming seaside communities are nearby and within arms reach, including Chester Basin’s public wharf, a seaside restaurant, pharmacy, and a marina to store sailboats, all just a short drive away. The Village of Chester is where all your necessities and desired activities like Sailing, Golfing, Theatre, fine dining, shopping and delicious coffee can be enjoyed. Nearby are the lovely communities of Mahone Bay and Lunenburg, two of the South Shore’s most popular gathering hubs. Don’t miss this opportunity to call Nova Scotia’s treasured South Shore your new home!

Swallow Cove Spur Unit Lot 3-C, Chester Basin

Chester Homes for Sale

Newest Chester Homes for Sale

Sean Nykolyshyn

Search

Resources

About