THE NEIGHBOURHOOD

Chester

Nova Scotia

A Coastal Village Rich in Charm and Community

Located along the scenic Lighthouse Route, Chester is a picturesque seaside village known for its sailing culture, arts community, and relaxed lifestyle. With its stunning ocean views, heritage homes, and active community life, Chester offers the perfect mix of coastal charm and small-town sophistication.

A Brief History

Founded in the mid-1700s and officially incorporated in 1963, Chester has long been a summer haven for artists, sailors, and visitors from across Canada and beyond. Its deep natural harbour made it an early hub for shipbuilding and fishing. Today, Chester's historic character is preserved in its classic New England–style architecture, quaint inns, and cultural institutions that celebrate its rich maritime legacy.

Official Town of Chester website ->   www.chester.ca

Chester on the map

A Coastal Village Rich in Charm and Community

Chester is located on Nova Scotia’s South Shore, approximately halfway between Halifax and Lunenburg. Just over an hour’s drive from Halifax via Highway 103, it offers easy access to nearby communities like Mahone Bay and Bridgewater.

Key Location Highlights:

~70 km from Halifax (approx. 1 hr via Hwy 103)

35 minutes to Lunenburg and Mahone Bay

Ferry access to Tancook Islands

On the scenic Lighthouse Route (NS Trunk 3)

Get Outside

Experience Nature in and Around Chester, Nova Scotia

Chester, NS is a charming seaside village on Nova Scotia’s South Shore, offering the perfect base for outdoor adventure and coastal exploration. Locals and visitors alike enjoy a wide range of outdoor activities just minutes from the heart of the community. Stroll or cycle along scenic trails, explore the nearby Chester Connection Trail, or paddle through the calm waters of Mahone Bay dotted with picturesque islands.

For beach lovers, Chester provides easy access to some of the South Shore’s most beautiful coastal spots. Relax at nearby Graves Island Provincial Park, just a short drive from the village, or venture slightly farther to the soft sands of Bayswater Beach and Hirtle’s Beach—perfect for swimming, picnicking, or simply soaking up the seaside atmosphere.

Nature enthusiasts will also enjoy the region’s excellent sailing, kayaking, hiking, and golfing opportunities, as well as breathtaking drives along the iconic Lighthouse Route. Whether you're planning a relaxing weekend or looking for an active day outdoors, Chester is your gateway to the best of Nova Scotia’s coastal lifestyle.

While Chester offers the charm of a small seaside village, it still provides access to many essential services and amenities, both locally and nearby. Residents benefit from:

  • Local shops, cafés, and artisan boutiques
  • Healthcare services, including nearby clinics and access to South Shore Regional Hospital in Bridgewater
  • A vibrant arts and cultural scene
  • Excellent public and private schools in the surrounding area
  • Recreational facilities like the Chester Tennis Club and Chester Golf Club
  • Scenic parks, marinas, and walking trails

The village also hosts events year-round, such as the Chester Race Week and local farmers’ markets, all contributing to a strong sense of community and quality of life. Plus, with Bridgewater just 30 minutes away, residents enjoy convenient access to larger retail centers, sports complexes, and specialized services when needed.

Amenities

Close to everything just around the corner

  • Imperfections Cafe
  • The Jib Coffee House and Bistro
  • The Kiwi Cafe
  • Tim Hortons
  • The Jib
  • Lordly Park
  • Freda's Beach
  • Chester District School
  • Chester Area Middle School

Shop And Dine

Chester has it all

With its picturesque village atmosphere and vibrant coastal charm, Chester, NS is a beloved South Shore destination for boutique shopping, local flavor, and authentic experiences. Wander through the village’s walkable core to discover artisan studios, curated gift shops, galleries, and home décor boutiques offering truly one-of-a-kind finds.

Chester also boasts a cozy and creative food scene. From seaside cafés and bakeries to bistros and family-run restaurants, you’ll find fresh, locally inspired dishes and warm Maritime hospitality. Whether you're enjoying a coffee by the harbour or browsing local markets, Chester blends small-town charm with elevated shopping and dining—all set against the backdrop of stunning ocean views.

Search Chester, Nova Scotia Available Properties

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1-12/22

  • 149 Duke Street in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202601279

    149 Duke Street 405-Lunenburg County Chester B0J 1J0
    Main Photo: 149 Duke Street in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202601279

    149 Duke Street Chester B0J 1J0 405-Lunenburg County

    $569,000
    Residential
    Status:
    Active
    MLS® Num:
    202601279
    Bedrooms:
    4
    Bathrooms:
    2
    Floor Area:
    1,700 sq. ft.
    A CHESTER CLASSIC. For a buyer who values history and heart, this is an opportunity to restore a Chester classic and build a life inside it, one chapter at a time. With roots stretching back to the early 1900s, this home offers a rare blend of heritage and lifestyle, located in the heart of the Village, an easy walk to schools, groceries, the yacht club, theatre, shops and restaurants. The home features 9' ceilings on the main floor, twin parlours, one with a pellet stove, spacious kitchen, main floor laundry, main floor bedroom and 3 spacious bedrooms upstairs. The current owners raised their family here and now it is time for a new family to bring fresh energy, create memories and carry the legacy forward. A manageable size yard for gardens, morning coffee and summer evenings after a day on the water. If you are a renovator, designer or buyer looking beyond today, this is worth your time. More details
    Listed by Engel & Volkers (Chester)
    LISTING DETAILS

  • 211 Old Trunk 3 in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202600704

    211 Old Trunk 3 405-Lunenburg County Chester B0J 1J0
    Main Photo: 211 Old Trunk 3 in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202600704

    211 Old Trunk 3 Chester B0J 1J0 405-Lunenburg County

    $179,900
    Residential
    Status:
    Active
    MLS® Num:
    202600704
    Bedrooms:
    2
    Bathrooms:
    1
    Floor Area:
    634 sq. ft.
    WHY PAY RENT. Ideal starter home or cottage within the Chester Golf Course membership area. Currently rented so it could also be an income property. Walk to all that Chester has to offer. The level yard is sunny with space for gardens. The 2 bedroom home is compact but with a bit of work and imagination, it could be cute and contemporary. Current owner has upgraded electrical, added a heat pump, new drilled well, water conditioner, and added a metal roof. More details
    Listed by Engel & Volkers (Chester)
    LISTING DETAILS

  • Lot 3 Target Hill Road in Chester: 405-Lunenburg County Vacant Land for sale (South Shore) : MLS®# 202600257

    Lot 3 Target Hill Road 405-Lunenburg County Chester B0J 1J0
    Main Photo: Lot 3 Target Hill Road in Chester: 405-Lunenburg County Vacant Land for sale (South Shore) : MLS®# 202600257

    Lot 3 Target Hill Road Chester B0J 1J0 405-Lunenburg County

    $80,000
    Vacant Land
    Status:
    Active
    MLS® Num:
    202600257
    1.4-acre property in Chester offers the perfect blend of private natural retreat and village convenience, featuring 123 feet of frontage on the Rum Runners Trail, ideal for cycling and hiking to Mahone Bay, Lunenburg, and beyond. Imagine building your dream home on a superb, level site with ample privacy, while also enjoying the unique opportunity for regular visits to the neighbouring Sensea Spa. There is a partially cleared area at the ideal building site. It is surrounded by old growth pines, apple trees and a mix of maple and birch. Just a short walk to charming Chester village, you'll have easy access to everything from fine art at Amicus Gallery and theatre at the Chester Playhouse, to dockside seafood chowder at the Rope Loft, lattes at the Kiwi Café, sailing at the Chester Yacht Club, and sports at the Chester Tennis & Golf Clubs. More details
    Listed by Domus Realty Limited
    LISTING DETAILS

  • 18 Wilson Drive in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202529663

    18 Wilson Drive 405-Lunenburg County Chester B0J 1N0
    Main Photo: 18 Wilson Drive in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202529663

    18 Wilson Drive Chester B0J 1N0 405-Lunenburg County

    $999,900
    Residential
    Status:
    Active
    MLS® Num:
    202529663
    Bedrooms:
    4
    Bathrooms:
    3
    Floor Area:
    2,697 sq. ft.
    If you are looking for a brand new built home in Chester we have what you are looking for. This home on Wilson Drive's main floor has a spacious kitchen with a large island, a Great room with a cozy fireplace, Primary bedroom with a walk-in closet and ensuite bath. There are two more bedrooms on this level, another full bath, mudroom and laundry. Above the garage you will find a full one bedroom gueste suite. Perfect for extended family or overnight guests. This home boasts in-floor radiant heating and a double garage. A great opportunity to have a new home in Chester, close to the golf course and a short walk to amenties. More details
    Listed by Harbourside Realty Ltd.
    LISTING DETAILS

  • 48 Valley Road in Chester: 405-Lunenburg County Vacant Land for sale (South Shore) : MLS®# 202528493

    48 Valley Road 405-Lunenburg County Chester B0J 1J0
    Main Photo: 48 Valley Road in Chester: 405-Lunenburg County Vacant Land for sale (South Shore) : MLS®# 202528493

    48 Valley Road Chester B0J 1J0 405-Lunenburg County

    $899,000
    Vacant Land
    Status:
    Active
    MLS® Num:
    202528493
    DEVELOPMENT DREAM A central three-quarter acre lot on a gently sloped grade is ready for development. Pending municipal approval, the potential options are varied; two buildings with ten units each, a hotel, or subdivide into six lots and build semi-detached residences. Valley Road is designated a village commercial corridor, so multi use residential/commercial mix could also be a viable option, pending municipal approval. Bordered by Queen Street, Main Street and Valley Road, the location couldn’t be more central in the village. Various planning renditions, mock up plans and submissions to the municipality are available by request. Chester is a singular village where everything is possible, including fine art at the Captains House Gallery, 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, relaxation at the Sensea Nordic Spa, fresh produce from the Farmer’s Market, hiking and cycling on The Rum Runners Trail, and sports at the Chester Tennis, Curling & Golf Clubs; all this capped by a quick 45-minute drive to the city of Halifax thanks to Highway 103’s so-called twinning completion. More details
    Listed by Duckworth Real Estate(Chester)
    LISTING DETAILS

  • 97 Nauss Point Road in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202528543

    97 Nauss Point Road 405-Lunenburg County Chester B0J 1J0
    Main Photo: 97 Nauss Point Road in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202528543

    97 Nauss Point Road Chester B0J 1J0 405-Lunenburg County

    $1,150,000
    Residential
    Status:
    Active
    MLS® Num:
    202528543
    Bedrooms:
    5
    Bathrooms:
    3
    Floor Area:
    2,548 sq. ft.
    Welcome to this beautifully reimagined 5-bedroom, 3-bath home in the heart of Chester, NS— perfectly positioned to capture unobstructed views of Chandler’s Cove, the Chester Golf Club, and the iconic Front Harbour. This exceptional property blends modern comfort with classic coastal charm, offering an ideal retreat in one of Nova Scotia’s most sought-after seaside communities. Situated on a generous lot with room for future expansion, the home is just moments from the Chester Yacht Club, local shops, cafés, and acclaimed restaurants—making every convenience easily accessible. Inside, extensive renovations have brought the home back to its very bones: interior walls taken to the studs, new insulation, new wiring, new plumbing, and more. The result is a bright, airy interior flooded with natural light, offering both peace of mind and a fresh contemporary feel. A spacious new deck spans the back of the home, providing the perfect spot for morning coffee, sunset cocktails, or simply soaking in the spectacular views that stretch out in every direction. With a Generac generator in place, you’ll enjoy reliable comfort year-round. With its prime location, modern upgrades, and breathtaking vistas, this Chester gem is ready to welcome its next chapter. More details
    Listed by EXIT Realty Inter Lake
    LISTING DETAILS

  • 87 Prince Street in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202528323

    87 Prince Street 405-Lunenburg County Chester B0J 1J0
    Main Photo: 87 Prince Street in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202528323

    87 Prince Street Chester B0J 1J0 405-Lunenburg County

    $659,000
    Residential
    Status:
    Active
    MLS® Num:
    202528323
    Bedrooms:
    3
    Bathrooms:
    2
    Floor Area:
    1,274 sq. ft.
    CHESTER ONE LEVEL LIVING. Recently updated three bedroom home located in the heart of the village on a large corner lot across from Lordly Park. Convenient to the yacht club, live theatre, shops, and restaurants, cafes, Freda's Beach, golf, and so much more that Chester has to offer. Features of the home include open concept, living dining kitchen area, propane fireplace, efficient, heat pump for heating and cooling, main floor laundry, new flooring throughout, updated kitchen, and bathrooms. Screened private back area ready to add a hot tub. Large level treed yard with lots of room for gardens and family fun. More details
    Listed by Engel & Volkers (Chester)
    LISTING DETAILS

  • 15 Fredas Point Drive in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202525911

    15 Fredas Point Drive 405-Lunenburg County Chester B0J 1J0
    Main Photo: 15 Fredas Point Drive in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202525911

    15 Fredas Point Drive Chester B0J 1J0 405-Lunenburg County

    $5,950,000
    Residential
    Status:
    Active
    MLS® Num:
    202525911
    Bedrooms:
    4
    Bathrooms:
    4
    Floor Area:
    3,389 sq. ft.
    15 Fredas Point is more than a residence, it is an embodiment of coastal craftsmanship, elevated living, and timeless design. Perched on 1.2 acres above Chester’s Front Harbour, this private, gated estate offers 150 feet of direct ocean frontage and sweeping views of Quaker, Meisner’s, and Saddle Islands. A true Chester original, the home has been thoughtfully restored, seamlessly blending heritage charm with modern sophistication. A three-car garage with a roughed-in suite crowns the property, while a winding driveway passes through illuminated, manicured grounds that create a tranquil, resort-like ambience. Near the water, a private seating area invites quiet reflection, flowing naturally to a shared wharf that offers effortless harbour access. Inside, exposed beams, softwood floors, and wrought iron accents honour the home’s 19th-century origins, complemented by a new cedar roof, designer lighting, and fully renovated baths. The kitchen’s custom cabinetry conceals integrated appliances for a refined, cohesive aesthetic, while the primary suite captures sweeping harbour views, offering a luxurious ensuite and a serene sitting area. A property of rare distinction, 15 Fredas Point stands as a testament to Chester’s enduring beauty and the art of coastal living. More details
    Listed by Sotheby's International Realty Canada
    LISTING DETAILS

  • 59 Union Street in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202525517

    59 Union Street 405-Lunenburg County Chester B0J 1J0
    Main Photo: 59 Union Street in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202525517

    59 Union Street Chester B0J 1J0 405-Lunenburg County

    $925,000
    Residential
    Status:
    Active
    MLS® Num:
    202525517
    Bedrooms:
    3
    Bathrooms:
    3
    Floor Area:
    2,039 sq. ft.
    Located in the heart of Chester where everything is just a short stroll away – This newly built home offers an easy lifestyle in one of Nova Scotia’s most charming seaside villages. The thoughtfully designed exterior showcases the classic architecture found across the South Shore, blending seamlessly with the village aesthetic. Step inside to 9 ft. ceilings, arched doorways, and large windows that flood the home with natural light. The main level features a bright open-concept living area with expansion possibilities at the back of the home by the builder- ask listing agent for details. .High quality finishes like engineered hardwood floors, a propane fireplace, and a luxurious kitchen with quartz countertops, custom cabinetry, and Thor appliances including a propane range make this home shine!. The main-floor primary bedroom offers convenience and privacy, complete with a walk-in closet and ensuite bath with a custom tile shower. A skylit stair tower adds architectural charm, while the kitchen walkout leads to a sunny cedar deck — perfect for a morning coffee or taking in the sun. Upstairs, you’ll find two well-appointed bedrooms with high ceilings, generous closets, and a full bath with a stacked washer and dryer. The finished lower level adds extra living space with a cozy rec room and soft carpet floors — ideal for movie nights or family games. Quality features such as on demand hot water a ducted heat pump to keep the perfect temperature year round. This is your opportunity to enjoy village living at its finest at an exceptional quality home with modern amenities. More details
    Listed by Engel & Volkers (Chester)
    LISTING DETAILS

  • Lot Valley Road in Chester: 405-Lunenburg County Vacant Land for sale (South Shore) : MLS®# 202524695

    Lot Valley Road 405-Lunenburg County Chester B0J 1J0
    Main Photo: Lot Valley Road in Chester: 405-Lunenburg County Vacant Land for sale (South Shore) : MLS®# 202524695

    Lot Valley Road Chester B0J 1J0 405-Lunenburg County

    $140,000
    Vacant Land
    Status:
    Active
    MLS® Num:
    202524695
    Affordable building lot in Chester Village! This 3,600 sq. ft. corner lot is zoned Central Commercial, which permits a variety of uses including single family home, commercial building or multi-unit residential. The property has a culvert/gravel driveway already in place. Located within walking distance to grocery store, restaurants, shops, Yacht & Tennis clubs, this is a rare opportunity in one of the South Shore's most coveted communities. More details
    Listed by Partners Global Corporate Real Estate Inc.
    LISTING DETAILS

  • 3 Chester Shore Road in Chester: 405-Lunenburg County Vacant Land for sale (South Shore) : MLS®# 202519545

    3 Chester Shore Road 405-Lunenburg County Chester B0J 1J0
    Main Photo: 3 Chester Shore Road in Chester: 405-Lunenburg County Vacant Land for sale (South Shore) : MLS®# 202519545

    3 Chester Shore Road Chester B0J 1J0 405-Lunenburg County

    $1,249,000
    Vacant Land
    Status:
    Active
    MLS® Num:
    202519545
    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. More details
    Listed by Duckworth Real Estate(Chester)
    LISTING DETAILS

  • 10 Chester Hills Drive in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202519362

    10 Chester Hills Drive 405-Lunenburg County Chester B0J 1J0
    Main Photo: 10 Chester Hills Drive in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202519362

    10 Chester Hills Drive Chester B0J 1J0 405-Lunenburg County

    $449,900
    Residential
    Status:
    Active
    MLS® Num:
    202519362
    Bedrooms:
    2
    Bathrooms:
    2
    Floor Area:
    1,308 sq. ft.
    Welcome to Chester Hills, a charming new retirement community in Chester, Nova Scotia. These beautifully designed single-level homes feature 2 bedrooms and 2 modern bathrooms. Inspired by Chester’s timeless charm, each home offers elegant architectural details and high-quality finishes. Enjoy an open-concept living space with large windows and vaulted ceiling, a gourmet kitchen with quartz countertops, and a serene primary suite with a luxurious ensuite bathroom. Outside, you'll find landscaped yards and private backyard patios, perfect for enjoying the picturesque surroundings. Don't miss your chance to be a part of this exceptional community! More details
    Listed by Parachute Realty
    LISTING DETAILS
1-12/22
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Data was last updated February 2, 2026 at 01:20 AM (UTC)