Chester Homes for Sale
Chester Homes for Sale
Chester, Nova Scotia, is a charming coastal village renowned for its sailing culture, scenic harbour, and relaxed seaside lifestyle. Known for its historic homes, waterfront properties, and vibrant arts and dining scene, Chester offers a unique blend of character and coastal elegance. Residents enjoy access to beaches, boating, golf, and walking trails, all within a welcoming, close-knit community. Located within commuting distance of Halifax, Chester is ideal for buyers seeking refined coastal living, natural beauty, and long-term value in one of Nova Scotia’s most desirable seaside towns.
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15 Fredas Point Drive in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202604397
15 Fredas Point Drive Chester B0J 1J0 
$5,850,000Residential- Status:
- Active
- MLS® Num:
- 202604397
- 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 detailsListed by Sotheby's International Realty Canada- CHRIS PERKINS
- 1 (902) 2101223
- Contact by Email
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91 Driftwood Court in Garden Lots: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202600734
91 Driftwood Court Garden Lots B0J 2C0
$2,100,000Residential- Status:
- Active
- MLS® Num:
- 202600734
- Bedrooms:
- 5
- Bathrooms:
- 5
- Floor Area:
- 4,830 sq. ft.
Stunning executive 4-BR, 3 1/2 bath home with vaulted ceiling, + cottage. Ideally situated on 394 ft of oceanfront property. Designed to maximize water views it offers a seamless blend of modern convenience and costal charm. Lg open kitchen, floor to ceiling cabinets, Corian countertops, island with prep sink & seats for 4, gas range with hood, walk-in pantry. Other main floor rooms include: open concept dining & living areas with gas fireplace; an expansive primary suit; 2nd BR; main bath with in floor heat; laundry; 2PC bath. HW stairs to the 2nd level catwalk leading to 3 & 4th BR; 3rd bath, massive games room with wet bar and space for an office. Other property features: 1 BR cottage; pier with floating dock. See features sheet for more details including Russ whole-home sound system and whole home generator. More detailsListed by Royal LePage Atlantic- CHRIS PERKINS
- 1 (902) 2101223
- Contact by Email
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123 Duke Street in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202515495
123 Duke Street Chester B0J 1J0
$1,795,000Residential- Status:
- Active
- MLS® Num:
- 202515495
- Bedrooms:
- 4
- Bathrooms:
- 5
- Floor Area:
- 4,250 sq. ft.
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. More detailsListed by PG Direct Realty Ltd.- CHRIS PERKINS
- 1 (902) 2101223
- Contact by Email
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103 Granite Street in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202606210
103 Granite Street Chester B0J 1J0
$1,450,000Residential- Status:
- Active
- MLS® Num:
- 202606210
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 2,116 sq. ft.
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. More detailsListed by Engel & Volkers (Chester) and Engel & Volkers- CHRIS PERKINS
- 1 (902) 2101223
- Contact by Email
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121 Duke Street in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202508297
121 Duke Street Chester B0J 1J0
$1,295,000Residential- Status:
- Active
- MLS® Num:
- 202508297
- Bedrooms:
- 3
- Bathrooms:
- 2
- Floor Area:
- 1,808 sq. ft.
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. More detailsListed by PG Direct Realty Ltd.- CHRIS PERKINS
- 1 (902) 2101223
- Contact by Email
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97 Nauss Point Road in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202528543
97 Nauss Point Road Chester B0J 1J0
$1,150,000Residential- 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 detailsListed by EXIT Realty Inter Lake- CHRIS PERKINS
- 1 (902) 2101223
- Contact by Email
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18 Wilson Drive in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202529663
18 Wilson Drive Chester B0J 1N0
$999,900Residential- 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 detailsListed by Harbourside Realty Ltd.- CHRIS PERKINS
- 1 (902) 2101223
- Contact by Email
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43 Queen Street in Chester: 405-Lunenburg County Multi-Family for sale (South Shore) : MLS®# 202602660
43 Queen Street Chester B0J 1J0
$899,000Multi-Family- Status:
- Active
- MLS® Num:
- 202602660
Nestled in the heart of the Village, this iconic café has served as a cherished gathering spot for locals and visitors alike for decades. Positioned in a premier downtown location, the property enjoys exceptional street visibility and a steady stream of foot traffic. The main level features a 2,544 SF commercial space radiating "cottage-chic" charm. With natural wood accents, a striking beachstone fireplace, and sun-drenched windows, the atmosphere is effortlessly inviting. Currently configured with a well-equipped commercial kitchen, two public restrooms, and ample storage, the space is a turnkey solution for a restaurant, boutique retail, or a serene yoga studio. Above the bustling storefront are three modern, fully renovated apartments. Each unit boasts updated kitchens and baths, serviced by ductless heat pumps and electric baseboards for year-round climate control. Whether you're looking for an owner-occupier setup or a high-yield investment, the history and energy of this landmark location ensure it will remain a cornerstone of the community for years to come. More detailsListed by Engel & Volkers (Chester) and Engel & Volkers- CHRIS PERKINS
- 1 (902) 2101223
- Contact by Email
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59 Union Street in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202606764
59 Union Street Chester B0J 1J0
$889,000Residential- Status:
- Active
- MLS® Num:
- 202606764
- 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. 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 detailsListed by Engel & Volkers (Chester)- CHRIS PERKINS
- 1 (902) 2101223
- Contact by Email
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19 Bond Drive in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202604428
19 Bond Drive Chester B0J 1J0
$759,900Residential- Status:
- Active
- MLS® Num:
- 202604428
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 2,828 sq. ft.
There are many beautiful locations along the South Shore, and Chester is definitely one of them. Have you been thinking, " I would love to live in Chester, in a new home, but I don't think I can afford to?" Here is your opportunity: affordable, new, and in Chester. This home was completely renovated in the last 4 years. Walk in and have no worries. New doors, new windows, new insulation, new drywall, new wiring, a new kitchen, new flooring, and a new bathroom. Shingles over the main area are only 6 years old, the back areas are 4 years old, the septic approx. 20 years old. Look at what this property offers any growing family or someone who wants everything on one level—and there is so much, much more. Plus, you have ample outdoor space for gardening, 2 large decks, a huge back yard and a very nice area for sitting, playing games, etc., just behind a 16 X 12 two-story shed. All just minutes from the famous Chester waterfront, that offers so much, yacht club, recreation, shopping, beautiful restaurants, and you are just minutes from Halifax. Bayer's Lake Shopping area, approx. 40 minutes away. If you want to leave the city and enjoy the tranquillity of the South Shore and still be near the City or the Annapolis Valley, this is the location for you. See LBO for more information on renovations and repairs. More detailsListed by Royal LePage Atlantic (New Minas)- CHRIS PERKINS
- 1 (902) 2101223
- Contact by Email
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132 Regent Street in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202509205
132 Regent Street Chester B0J 1J0
$729,000Residential- Status:
- Active
- MLS® Num:
- 202509205
- Bedrooms:
- 4
- Bathrooms:
- 2
- Floor Area:
- 1,816 sq. ft.
Tucked away on a quiet street, this fully renovated home offers a rare mix of modern comfort and relaxed village living in the heart of Chester Village. It feels calm and peaceful—yet you're just a short stroll from cafés, shops, the yacht club, and the harbour. Surrounded by a lush grassy lawn on a sunny corner lot, step inside and you'll find a bright, open layout designed for entertaining. The entire space flows together effortlessly—and from the living room, you can step straight out onto the wraparound deck and gazebo–perfect for outdoor dinners, morning coffee, and evening chats under the stars. Whether you're coming back from the beach, a day on the water, or a morning at the market, this home invites you to unwind. The modern kitchen with stone counters and high-tech appliances offers a stylish, functional space for everyday life. The main level features engineered hardwood floors, a warm shiplap accent wall, and a bright living room with grand Polytech windows. With four bedrooms and two full baths there's room for everyone to stay. The lower level has been newly finished–a bright and versatile rec room features a wall of windows, surround sound, and a wet bar with a wine fridge. The 2nd full bath and lower level bedroom make transforming the space to an in-law or rental suite an easy possibility. A sliding door opens to a private gravel patio offering an additional private outdoor space to relax which is cut into the hill and framed by a retaining wall with large stonework on the side of the house. Every detail has been thoughtfully upgraded—Whether you're looking for a full-time residence, a weekend escape, or a place to welcome friends and family, this Chester bungalow offers you the perfect seaside lifestyle to make new memories with family and friends. More detailsListed by Engel & Volkers (Chester) and Engel & Volkers- CHRIS PERKINS
- 1 (902) 2101223
- Contact by Email
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165 King Street in Chester: 405-Lunenburg County Residential for sale (South Shore) : MLS®# 202514095
165 King Street Chester B0J 1J0
$699,000Residential- Status:
- Active
- MLS® Num:
- 202514095
- Bedrooms:
- 2
- Bathrooms:
- 3
- Floor Area:
- 1,204 sq. ft.
Central village home with over 1200 square feet of living space, two bedrooms, two bathrooms and two parking spots! On the quiet part of King Street, you will sleep soundly here. Entering the home, the first thing you will notice are the lush natural views from the main living room vaulted ceiling windows. A second-floor bedroom with Juliet balcony overlooks the main living/dining room giving a delightful open spacious feel. The main floor bedroom and full bathroom are a convenient feature for one level living. Enjoy preparing a meal in the galley kitchen, with new sliding door access to the 40 ft long deck for barbecue summer gatherings. Keep your toes warm in the winter with the wood burning fireplace, and a new conditioning system is in place for the well water. 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. All furnishings are included in the sale, so it is turn key property. The previous long-term tenant was paying over $3K per month, so it would work well as an investment opportunity. More detailsListed by Duckworth Real Estate(Chester)- CHRIS PERKINS
- 1 (902) 2101223
- Contact by Email
Data was last updated April 10, 2026 at 07:20 AM (UTC)
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Office Address:
1 - 2207 Gottingen Street
Halifax , NS, B3K 3B5