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$349,900
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
$549,000
2 Beds ⋅ 3 Baths ⋅ 202622410 MLS
CAREFREE CONDO LIVING, CHESTER. Enjoy the flexibility, comfort, and space of a detached home without any of the maintenance burdens. This meticulously maintained bungalow-style townhome in Chandler’s Cove offers effortless, one-level main living paired with a fully finished lower-level guest retreat. The light-filled main floor features an open-concept layout with gleaming hardwood floors, updated lighting, central vacuum, an efficient kitchen, and a primary suite with a private ensuite. A versatile den serves as an ideal home office or second main-floor bedroom, accompanied by a guest bathroom. Off the principal living area, step out onto a sunny, spacious back deck—perfect for outdoor dining or evening relaxation. Downstairs, the fully finished lower level provides privacy for visiting family and friends, complete with a family/media room, a third bedroom, and a private ensuite bath. Additional features include a large lower-level laundry room, plus main-floor plumbing in place should you prefer main-level laundry facilities. Beyond your doorstep, embrace everything Chester has to offer: an active community centre within Chandler's Cove Village, world-class golf, sailing at the Chester Yacht Club, live theatre, tennis, curling, the Lido outdoor saltwater pool, local cafes, fine dining, and the scenic Chester Connection Trail for hiking and cycling. A perfect balance of community, convenience, and luxury.

21 Millennium Drive, Chester
$779,900
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
$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
$199,000
202618645 MLS
A very private interior 1.75-acre lot accessible from the Fairway Lane cul-de-sac. Of the five lots, this is the only one not bordering the Chester Golf Course/road. If you love natural surroundings but want to be close to the village, this location is ideal. It is an easy walk to NS’s most walkable village. The distance is less than 2 KMs to Chester’s downtown. A subdivision survey with perc testing sites is available, showing a total of five available lots with pricing. A drilled or dug well would be the responsibility of the new owner and electrical utility will be supplied to the lot line by the vendor. Also available are the potential restrictive covenants detail, pending legal review. Shared access for the lots will be from Fairway Lane the cul-de-sac off Golf Course Road which is being levelled through Dexter Construction. A shared road agreement will be in place once the first lot has been sold. 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.

Fairway Lane, 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
$164,900
202618241 MLS
Oceanfront Opportunity in Chester! Build your dream coastal retreat on this exceptional 10,000 sq. ft. oceanfront lot offering 104 feet of direct Atlantic Ocean frontage. Nestled in a protected cove, this level property has already been prepared for construction, making it the perfect canvas for your future home or cottage. The lot has an approved septic system, allowing you to move forward with confidence. Enjoy breathtaking water views, easy shoreline access, and the peace and privacy of one of Nova Scotia’s most desirable coastal communities, all while being just minutes from the amenities, marina, and charm of Chester. As an added bonus, the seller is willing to include the existing motorhome with the property for an increased purchase price, providing an ideal place to stay while you build or a turnkey seasonal getaway. This is a rare opportunity to own a ready-to-build waterfront property in one of the South Shore’s most sought-after locations.

Goat Lake Road Unit Lot, Chester
$239,000
202618051 MLS
A premier building lot just shy of an acre on Golf Course Road, this corner piece also has access from the Fairway Lane cul-de-sac. Adjacent to the Chester Golf Club, it is also an easy walk to the village of Chester. A subdivision survey with perc testing sites is available, showing a total of five available lots with pricing. A drilled or dug well would be the responsibility of the new owner and electrical utility will be supplied to the lot line by the vendor. Also available is a potential restrictive covenants detail, pending legal review. Shared access for the lots will be from Fairway Lane the cul-de-sac off Golf Course Road which is being levelled through Dexter Construction. A shared road agreement will be in place once the first lot has been sold. 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.

Golf Course Road Unit Lot 5, Chester
$399,000
202618045 MLS
A premier building lot spanning 1.8 acres with direct frontage on the 15th fairway of the Chester Golf Club. This corner piece has access from Fairway Lane cul-de-sac, which runs north from Golf Course Road. An easy walk to the village of Chester so you can clock in your daily 10,000 steps! A subdivision survey with perc testing sites is available, showing a total of five available lots with pricing. A drilled or dug well would be the responsibility of the new owner and electrical utility will be supplied to the lot line by the vendor. Also available is a potential restrictive covenants detail, pending legal review. Shared access for the lots will be from Fairway Lane the cul-de-sac off Golf Course Road which is being levelled through Dexter Construction. A shared road agreement will be in place once the first lot has been sold. 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.

Fairway Lane Unit Lot 4, 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
$2,950,000
202617915 MLS
Visit REALTOR® website for additional information. 7 Bed | 7 Bath | 6,058 sq ft | 0.39 ac | Outdoor Pool | Registered Mooring A rare dual-property estate in the heart of Chester village, combining two fully upgraded residences into one exceptional compound—ideal as a family retreat, multi-generational home, or turnkey vacation-rental operation. Over 6,000 sq ft of refined living, 7 bedrooms and 7 bathrooms, all within walking distance of the village centre, waterfront, and Chester Yacht Club. Just 40 minutes to Halifax (under 30 with the new Highway 3 twinning). 123 Duke St – Heritage residence (former Casa Blanca Inn): Currently two separate suites, easily converted to one grand home. Lower garden suite offers 1,700 sq ft / 2 bedrooms, ideal for rental or guests. Upper executive suite spans 2,500+ sq ft with a spacious master, spa-like ensuite, private gym, library, and living areas. 121 Duke St – Contemporary residence: 1,800 sq ft, 3 bed / 2 bath on a private flag lot. Fully furnished and rental-ready. Features a 60-ft saltwater lap pool (new liner, automatic cover), multiple decks, new heat pumps, propane fireplace, and a games room. Built for peace of mind: Deep drilled well with automatic water management, advanced sump/drainage systems (basements stayed dry through recent area flooding), buried electrical, Cat 6 wiring, and permeable Ecoraster driveway. Elevated water views, safely above the flood zone. Registered mooring buoy in protected Front Harbour included; professional property management in place. Minutes to Chester Golf Club, Sensea Nordic Spa, dining, the Playhouse, and trails. Showings require 48 hours' notice.

121 & 123 Duke Street, 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
$225,000
202616074 MLS
Build your dream home in one of Nova Scotia’s most desirable seaside communities! This exceptional building lot on Riverside Cove in Chester offers an incredible head start, with a drilled well, septic system, poured concrete foundation, and detached single garage already in place. The property also includes house plans, making it even easier to bring your vision to life. Enjoy beautiful views of Hennigar Lake while being just minutes from the charming village of Chester, renowned for its sailing, golf, beaches, boutiques, restaurants, and vibrant summer atmosphere. Whether you’re looking for a year-round residence or the ultimate seasonal retreat, this is a rare opportunity to build in a location that’s truly synonymous with Nova Scotia summer living. Your dream home starts here!

27 Riverside Cove, 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
$1,190,000
202614937 MLS
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.

3 Chester Shore Road, Chester
$319,000
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, heatpump, updated bathroom and some new windows. A versatile loft space provides excellent overflow for guests or 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
$319,000
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, heatpump, updated bathroom and some new windows. A versatile loft space provides excellent overflow for guests or 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
$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
$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. Strategically positioned with direct access to Highway 3 and close to marinas, boutiques, cafés, and dining, this unique property 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
$648,000
4 Beds ⋅ 202611442 MLS
Excellent income property opportunity in the heart of the Village of Chester. Ideally located on desirable Queen Street, this updated duplex is within walking distance to Chester’s waterfront, Chester Playhouse theatre, shops, restaurants and other local amenities. This well-maintained two-level property features two self-contained 2-bedroom units, each offering updated kitchens, appliances and bathrooms. A solid opportunity for investors seeking a turnkey income property in a highly desirable coastal community, buyers looking for a multi-unit property with flexible future potential or an outstanding opportunity for buyers looking to offset ownership costs with rental income. Currently tenant occupied with strong rental income and scheduled rent increases coming into effect July 1. Situated in one of Nova Scotia’s most sought-after seaside villages, this property offers an excellent combination of location, lifestyle and investment potential.

138 Queen Street, Chester
$199,000
202611188 MLS
Fantastic opportunity to develop a central 1.8 acre building lot in the village of Chester. Zoned R4 (multi-unit residential), the municipality has also confirmed the potential locations for the building envelope. This property also has septic confirmed at the land surveyor’s office. A water course running through the eastern side of the property will ensure a green space/non-development area. Municipal correspondence can be provided for all serious enquiries. 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.

4-AB Chandler Road Unit Lot, Chester
$725,000
2 Beds ⋅ 3 Baths ⋅ 202610890 MLS
This masterfully crafted new-construction custom home is perfectly situated in the vibrant heart of Chester, Nova Scotia. Offering a seamless blend of classic South Shore architecture and modern luxury, you are a short stroll from the renowned Chester Yacht Club, Playhouse, fine dining, charming local shops, cafés and also minutes from the Chester Golf Course. Upon entering you are greeted by soaring nine-foot ceilings and expansive windows that flood the open-plan main floor with natural light. The gourmet kitchen is a chef's dream, featuring custom cabinetry, quartz countertops, high-end appliances, and a propane range. Cozy in-floor heating and a beautiful paver-stone patio that wraps around the side and back complete the main level. Thoughtful custom details continue throughout the second level, where vaulted ceilings and a bright landing with a wall of windows separate the two bedrooms. Each room is well-appointed - one facing south, the other north - and both showcase vaulted shiplap ceilings, luxurious ensuite bathrooms with custom tile showers and walk-in closets with elegant built-in shelving. Modern essentials including a fully ducted heat pump for year-round climate control and on-demand hot water ensure a high-performance, low-maintenance lifestyle. This home represents a rare opportunity to enjoy the timeless charm of village living in a residence built to the highest standards of modern quality and comfort.

69 Union Street, 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
$899,000
202602659 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
$849,000
202528493 MLS
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.

48 Valley Road, Chester
$229,000
202518153 MLS
A very private interior 1.75-acre lot accessible from the Fairway Lane cul-de-sac. Of the five lots, this is the only one not bordering the Chester Golf Course/road. If you love natural surroundings but want to be close to the village, this location is ideal. It is an easy walk to NS’s most walkable village. The distance is less than 2 KMs to Chester’s downtown. A subdivision survey with perc testing sites is available, showing a total of five available lots with pricing. A drilled or dug well would be the responsibility of the new owner and electrical utility will be supplied to the lot line by the vendor. Also available are the potential restrictive covenants detail, pending legal review. Shared access for the lots will be from Fairway Lane the cul-de-sac off Golf Course Road which is being levelled through Dexter Construction. A shared road agreement will be in place once the first lot has been sold. 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.

Fairway Lane Unit Lot 2, Chester