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$498,900
3 Beds ⋅ 2 Baths ⋅ 202621205 MLS
Welcome to 3912 North Street, perfectly situated in the heart of charming Chester! This 3-bedroom, 2-bathroom bungalow has been extensively renovated, featuring newer siding, windows, doors, heat pumps, updated flooring, fresh paint, a modern kitchen, and much more. Step inside to a generous foyer with ample room for family gear before flowing into the bright, open-concept living, dining, and kitchen area. The kitchen is designed for entertaining, complete with extensive cabinetry, a large breakfast bar overhang, and patio doors opening to a fully fenced backyard with a stone patio—perfect for summer barbecues and gatherings. Two spacious bedrooms and a full bathroom round out the well-appointed main floor. The fully renovated lower level boasts a massive primary suite with private walkout access, a large family room, and a stylish combined bath/laundry with a relaxing soaker tub (already roughed-in for a shower). The versatile layout offers exceptional flexibility: reconfigure the main level to create an additional bedroom, or capitalize on the private walkout entrance to explore secondary suite potential. Enjoy unbeatable coastal living—walk to local grocery stores and dining, or take a quick drive to the Chester Playhouse, dockside meals at the Rope Loft, morning coffee at the Kiwi Café, sailing at the Chester Yacht Club, and rounds at the Chester Golf and Tennis Clubs. Exceptional value in a premier location—book your private viewing today!

3912 North Street, 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
$599,900
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
$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
$599,900
3 Beds ⋅ 2 Baths ⋅ 202606878 MLS
CHESTER. 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
$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. 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