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$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
$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
$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
$674,900
3 Beds ⋅ 2 Baths ⋅ 202614294 MLS
Your Chester Home Awaits! This charming and custom-built home reflects quality craftsmanship throughout and sits set back from the road, offering a hidden world of privacy and natural beauty. The grounds are framed by low-hanging bushes and lush greenery to create secluded front and back patios that are perfectly suited for outdoor relaxation and entertaining family and friends. Lush perennials including roses, wildflowers, honeysuckle, bluebells, and poppies surround the property. Embrace a true garden-to-table lifestyle with your own side-yard greenhouse, ready for your next harvest. The main level is defined by an impressive two-storey ceiling above the dining area with big windows, an architectural floating staircase, and beautiful cherry hardwood. Tall windows to the west fill the home with light that illuminates exposed pine accents within to create a calming and warm interior setting. The large kitchen offers generous counter and storage space, a breakfast bar, new stainless steel appliances and a new glass cooktop. A functional den/bedroom with a built-in desk, a combined laundry/pantry and powder room, and a walkout to the private front porch complete this level. Floating solid cherrywood stair treads and a custom bookcase guide you to the upper level where vaulted ceilings, dormers, skylights, and grand gable-end windows fill two spacious bedrooms with light. A full bathroom features a skylight and walk-in shower. The dry poured-concrete basement offers walkout potential and includes a second wood stove, workbench, wine cellar, and wood butler lift that are essential for year-round residence. Situated in the Village of Chester this beautiful home with quality craftsmanship is within walking distance to great amenities, such as the Marina, farmers market, rails to trails, Fredas beach, the lido pool and lovely coffee, dining and shopping in the heart of the Village. Easy access to the Highway for under an hour drive to the International Airport and Halifax.

208 Victoria Street, Chester
$499,000
3 Beds ⋅ 1 Baths ⋅ 202613971 MLS
The light- filled and bright three bedroom home was built by local boat builder John Barkhouse in 1919. Used as the Barkhouse family home and the site of his early workshop for many years. The restored home retains charming features reflective of the boat builder’s trade including hand hewn planks, softwood floors and clever built in storage nooks. This year round home has been used most recently as a family cottage and profitable short term rental. Recent modernizations include updated 200 amp breaker panel, pex plumbing throughout, spray foam insulation, renovated bathroom and kitchen. The sunroom addition adds space and is the perfect spot to enjoy a morning cup of coffee. The back yard offers a private oasis with a fire-pit and flowering shrubs. The side yard hosts fruit trees and the front rock garden has established perennials. Walking distance to Sensea Spa, Rum Runners Trail and Chester Village amenities. This is the perfect location for anyone looking to live in Chester or invest in the area. A second lot is included in the purchase and is the location of the homes private well.

29 Old Trunk 3, Chester
$574,900
3 Beds ⋅ 3 Baths ⋅ 202611732 MLS
Tucked within the sought-after community of Chandler’s Cove, adjacent to the fairways of the Chester Golf Club, this townhouse bungalow offers the kind of lifestyle many are searching for, but rarely find. Designed for easy one-level living, the main floor is warm, welcoming, and thoughtfully laid out for everyday comfort. Whether it’s morning coffee before a tee time, quiet evenings on the deck, or hosting friends after a day in Chester, this is a home that feels effortless. What makes this property particularly special is the flexibility it offers. Downstairs, generous additional living space with a walkout creates the perfect retreat for visiting family and guests, giving everyone room to gather while still enjoying privacy. Grandchildren for the weekend, adult kids home for a visit, or simply space to spread out, it adapts beautifully to the season of life you’re in. Set within a well-kept condo community, this is low-maintenance living without compromise, seconds from the charm of Chester village, sailing, restaurants, and one of Nova Scotia’s most beloved golf courses.

73 Millennium Drive, Chester
$619,000
3 Beds ⋅ 2 Baths ⋅ 202606878 MLS
CHESTER VILLAGE HOME. Charming century home nestled on a quiet, peaceful street adjacent to Chester's Back Harbour, and nearby marinas. Enjoy effortless access to everything Chester is celebrated for - Yacht Club, shopping, fine dining and coffee shops, golf, curling, and live theatre, all minutes from your front door. Completely re-built by a master carpenter a number of years ago, features include high ceilings, refinished hardwood floors and traditional wide plank flooring, cosy living room with propane fireplace, large formal dining room that is designed to comfortably seat 8 to 10 people, main floor powder room with in-floor heating, and custom kitchen cabinetry. Exclusive, handcrafted pottery accents from Amacus Pottery are woven throughout the home, including custom lamps, a unique kitchen backsplash, and integrated bathroom sinks. The light and airy sunroom addition is a family focal point that leads to a two level deck, and steps down to a level back yard with fenced veggie garden. The upper level is comprised of three bedrooms, high ceilings, and a bathroom with custom shower. Offering the balance of village conveniences and regional access, this property is ideally located just 20 minutes from Mahone Bay, 30 minutes from Bridgewater amenities, and an easy 45-minute commute to downtown Halifax. Don't miss this rare opportunity to own a piece of Chester's history.

92 Main Street, Chester
$799,000
3 Beds ⋅ 3 Baths ⋅ 202606764 MLS
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.

59 Union Street, Chester
$1,450,000
3 Beds ⋅ 2 Baths ⋅ 202606210 MLS
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.

103 Granite Street, Chester
$749,900
3 Beds ⋅ 3 Baths ⋅ 202604428 MLS
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.

19 Bond Drive, Chester
$899,000
3 Beds ⋅ 202602660 MLS
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.

43 Queen Street, Chester
$1,295,000
3 Beds ⋅ 2 Baths ⋅ 202508297 MLS
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.

121 Duke Street, Chester