Chester NS Single Family Real Estate, Homes for Sale

3 Beds ⋅ 1 Baths ⋅ 202625027 MLS

Your cottage getaway is closer than you think! Welcome to Riverside Cove Road, where much of the hard work has already been done and your dream retreat is ready to take shape. This beautiful building lot has been cleared, with a foundation already poured and ready for your future home or cottage. Building plans are available, and with the septic and well already installed, you're well on your way to making your vision a reality. Just across the road, enjoy access to a beautiful, private lake - the perfect setting for swimming, paddling, fishing, or simply escaping the everyday and enjoying peaceful days by the water. And there's no need to wait to start enjoying the property! A travel trailer is already set up on site and comes with the property, giving you a comfortable place to stay while you build - or simply a ready-made weekend escape right now. Whether you're dreaming of a peaceful cottage retreat, a year-round home, or a place to spend summers by the lake, this property offers an incredible head start. Foundation, well, septic, plans and a travel trailer - it's all here. Just bring your vision and start enjoying Riverside Cove!

27 Riverside Cove, Chester

$479,000

4 Beds ⋅ 2 Baths ⋅ 202623820 MLS

HADDON HEIGHTS, CHESTER. Nestled in a quiet residential neighborhood on the edge of Chester. You will be just minutes away from everything this magical, unique community has to offer including live theatre, championship golf, world-class sailing, and local dining. The raised bungalow offers 2600 sq. ft of living space on two levels and an attached carport. The light filled home features solid oak hardwood floors in the living and dining room which carry into the hall and into one of the three main floor bedrooms. The kitchen updated in the early 2000's offers ample classic pickled oak cabinetry. There is hot water baseboard heating plus a heat pump for efficient heating and summer cooling. The lower level offers a spacious rec room with newer patio doors to the yard and cosy propane fireplace, a craft room or 4th bedroom, laundry room, and a second bathroom with sauna plus huge storage room to complete that level. The mature landscaping requires some trimming and pruning but could be easily reined in and a large wraparound deck provides the perfect footprint for outdoor entertaining, though it will need some refurbishment in the near future. This property has lots of potential and would make a great family home in a safe neighbourhood.

28 Oakview Drive, Chester

$839,000

3 Beds ⋅ 2 Baths ⋅ 202623141 MLS

Presenting a 15-year-old home in pristine condition, built with high end materials and thoughtful architectural design, on a gorgeous 0.87-acre pastoral setting. Upon entering, the living room has a bright ambiance with large windows throughout. Design features abound; a stately fireplace mantle, polished concrete flooring, shiplap walls, inset ceiling lighting and high ceilings. Moving into the dining/kitchen space, high end finishes are apparent, American Range gas stove, thoughtfully appointed cabinetry, quartz countertops, subway tile backsplash, and pendant lighting over the island. There is a great option for meals - seating for four at the island or eight at the dining table. Further down the main floor is room that is an ideal ground floor bedroom complete with full four-piece ensuite that is currently used as a cozy den with direct access to a screened in sunroom. Upstairs are two grand bedrooms, featuring dormered skylights and five-piece bathroom, complete with claw foot tub, as well as a balcony with spectacular views of the adjacent equestrian property. Energy efficiency was in mind when the home was built in 2011. Featuring a slab foundation with in-floor radiant heating on a low cost “time of use” power consumption system. Many additional attributes make this property in a class all its own. The exterior is picture perfect with complementary gardens and shrubbery, expansive barbecue deck off the sunroom, classic front porch veranda, spacious level driveway and exquisite surroundings. Chester is a seaside village where you can enjoy fine art at the Captains House Gallery, theatre at the Chester Playhouse, dockside seafood at the Rope Loft, Kiwi Café lattes, fine dining at the Sunroom, sailing at the Chester Yacht Club, tall tales at the Focsle Tavern, a day at the Sensea Nordic Spa, Farmer’s Market fresh produce, cycling on The Rum Runners Trail, and sports at the Chester Tennis, Curling & Golf Clubs. 0.87 acre lot to be subdivided from 1.67 acre lot.

4303 Highway 3, Chester

$324,900

2 Beds ⋅ 1 Baths ⋅ 202622422 MLS

Located in the sought-after community of Chester, this 2-bedroom, 1-bath home set on 4.79 acres offers an excellent opportunity to create a space that suits your style. The spacious yard provides room for gardening, entertaining, recreation, or simply enjoying the outdoors. Enjoy the charm and character of the Chester area, with its welcoming community and beautiful surroundings. A rare opportunity to own this much land in a beautiful and desirable area.

74 Old Trunk 3 Road, Chester

$749,999

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

$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

$674,000

3 Beds ⋅ 2 Baths ⋅ 202616126 MLS

MOTIVATED SELLER! 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

$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

$299,000

2 Beds ⋅ 1 Baths ⋅ 202614116 MLS

New septic installed 2026. This charming 2 bedroom, 1 bath home is a perfect opportunity for year-round living or a relaxing retreat in a highly sought-after seaside community. Located just outside the Village in the heart of Chester. Enter into a bright and cozy living area with the character of the original hardwood floors throughout the main level. The kitchen has been recently updated with open shelving, butcher block counters, and new appliances. Enjoy many thoughtful upgrades, including fresh paint throughout, a new roof, heat pump, updated bathroom and some new windows. A versatile loft provides an additional space for storage. Outside, the home is a gardener's delight, featuring extensive perennial gardens, a large greenhouse, and a spacious front patio perfect for overlooking the vibrant flower beds. Two outbuildings on concrete slab with loft space provide room for storage and your favourite hobbies. There is a drilled well to provide plenty of water for your needs and perfect for maintaining the gardens. The location is exceptional, offering easy access via walking distance to local amenities, the Rails to Trails, and falling within the desirable Chester Golf Course catchment area. Don't miss out on this opportunity to enjoy the beauty the lifestyle in Chester has to offer!

150 Chester Commons Road, Chester

$299,000

2 Beds ⋅ 1 Baths ⋅ 202614114 MLS

New septic installed 2026. This charming 2 bedroom, 1 bath home is a perfect opportunity for year-round living or a relaxing retreat in a highly sought-after seaside community. Located just outside the Village in the heart of Chester. Enter into a bright and cozy living area with the character of the original hardwood floors throughout the main level. The kitchen has been recently updated with open shelving, butcher block counters, and new appliances. Enjoy many thoughtful upgrades, including fresh paint throughout, a new roof, heat pump, updated bathroom and some new windows. A versatile loft provides an additional space for storage. Outside, the home is a gardener's delight, featuring extensive perennial gardens, a large greenhouse, and a spacious front patio perfect for overlooking the vibrant flower beds. Two outbuildings on concrete slab with loft space provide room for storage and your favourite hobbies. There is a drilled well to provide plenty of water for your needs and perfect for maintaining the gardens. The location is exceptional, offering easy access via walking distance to local amenities, the Rails to Trails, and falling within the desirable Chester Golf Course catchment area. Don't miss out on this opportunity to enjoy the beauty the lifestyle in Chester has to offer!

150 Chester Commons Road, Chester

$699,000

2 Beds ⋅ 3 Baths ⋅ 202613552 MLS

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.

165 King Street, 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. Currently used as AirBnb with active bookings into 2027, this could be your home or an income property. Positioned with direct access to Highway 3 and close to marinas, boutiques, cafés, and dining, this home 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

$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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