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1001 Azalea Court, South Chesapeake
$615,000
4 Beds ⋅ 2.1 Baths ⋅ 10632333 MLS
Nestled on a quiet cul-de-sac in the heart of Great Bridge, this beautifully maintained home is sure to impress. From the moment you arrive, the home’s curb appeal is undeniable, with a charming front porch that warmly welcomes you inside. The inviting floor plan features a formal dining room, a office/study, and a spacious living room. At the heart of the home, the kitchen shines with a large center island, shiplap backsplash, granite countertops, stainless steel appliances, and a bright breakfast nook. Upstairs, the primary suite offers a generous walk-in closet and an impressive en suite bathroom. Two additional bedrooms are well sized and provide ample closet space, while the finished room over the garage is great for a guest suite, media room, or flex space. Head outside to enjoy the expansive, fully fenced backyard complete with a large deck where you are sure to enjoy entertaining or relaxing while overlooking beautiful, mature trees.

1001 Azalea Court, South Chesapeake

110 Tidal Island Way, South Chesapeake
$695,000
4 Beds ⋅ 3.1 Baths ⋅ 10631096 MLS
Stunning Custom all brick home. This is a great home for living inside & especially outside. So many inside features; a bright cathedral foyer, Large living & dining rms. Family rm w/double french doors, gas fireplace & cathedral ceilings. Kitchen has heated ceramic floors, gas stove & vented hood w/warming lights & selves, granite & SSA. Large downstairs bedroom w/2 closets, excellent for inlaw suite. Good size laundry/ mudroom. Upstairs has large primary w/vaulted ceiling, gas fireplace, vanity area, custom bath with heated floors, double sinks, 2 shower heads & fireplace. Primary closet by California closets. Frog is 4th bedroom. Outside features a custom built screened porch (600sqft) w/vaulted ceiling, double fans and electric. Porch opens to large compost deck w/ built in hot tub, pergola, gas grill and bar top w/views of woods & wildlife. Lower level patio w/ built in bench for firepit. All landscaping professional designed. Sqft per city tax records. T&M provided by seller.

110 Tidal Island Way, South Chesapeake

2244 Benefit Road, South Chesapeake
$727,500
4 Beds ⋅ 2.1 Baths ⋅ 10631960 MLS
Welcome to 2244 Benefit Road in Chesapeake—a rare opportunity to own 6 private acres with the freedom of A-1 zoning and all the charm of country living, just minutes from city conveniences. This 2,300 sq ft home offers space, versatility, and major updates including a brand-new roof and new HVAC system for peace of mind. Bring your horses, cows, chickens and create the lifestyle you’ve been dreaming of—farmette, homestead, or private retreat. Bordered by a nature preserve, you’ll enjoy protected views and no future development behind you. The acreage, privacy, and agricultural zoning make this one stand out among Chesapeake homes for sale. Room to garden, ride, entertain, or simply enjoy wide open space under the stars. If you’ve been searching for homes with land in Chesapeake, horse property, or a unique rural escape with modern comfort, this is the one. Rarely does acreage, freedom, and location come together like this!

2244 Benefit Road, South Chesapeake

449 Sawyers Mill Crossing, South Chesapeake
$535,000
4 Beds ⋅ 3 Baths ⋅ 10630276 MLS
Beautifully remodeled 4-bed, 3 bath home, 2,384 sq. ft in sought after Sawyers Mill Community of Chesapeake & Grassfield Schools. Open/spacious living on 1st floor. New carpet & LVP, Fresh paint throughout, new light fixtures, ceiling fans, plumbing fixtures, toilets, new stainless steel appliances, white shaker cabinets in kitchen & baths, soft close doors & drawers, floor to ceiling pantry cabinet, Quartz/Granite countertops, blinds, patio slider. Flex room w/french doors can be used for a dining room/office/guest room. New tiled shower in primary bath, double vanities, walk in closet & separate water closet. Spacious bedrooms, hall bath features new tub shower surround, laundry closet on second floor. New Full bath on 1st floor. Modern finishes throughout. New HVAC system, roof replaced in 2022. Backyard features deck/shed & view of the community lake. Convenient to shopping, interstate, & bases. Enjoy activities hosted by the HOA to include a pool, playgrounds, & clubhouse.

449 Sawyers Mill Crossing, South Chesapeake

821 Stacey Place, South Chesapeake
$522,900
3 Beds ⋅ 2.1 Baths ⋅ 10627448 MLS
NEW HVAC, PAINT AND CARPET. Tucked away at the end of a quiet cul-de-sac on over an acre, this home offers a serene, park-like setting with exceptional privacy and space to enjoy. Inside, you’ll find attractive LVP flooring throughout the main level and a bright, open-concept layout designed for modern living. The spacious living area flows seamlessly into a stylish kitchen featuring quartz countertops—perfect for both everyday living and entertaining.A large two-car attached garage provides ample storage, while the expansive backyard offers endless possibilities, including plenty of room to add a pool or create your own outdoor retreat. Upstairs, the generous primary suite boasts two walk-in closets, complemented by two additional bedrooms for a total of three. A conveniently located upstairs utility room includes a washer and dryer that convey with the home.Ideally situated near shopping, dining, and major interstates, this property combines peaceful living with everyday convenience. Secure your contract now!

821 Stacey Place, South Chesapeake

200 Kwanzan Court, South Chesapeake
$677,350
4 Beds ⋅ 2 Baths ⋅ 10620658 MLS
Welcome to the Denton at Riverview Landing, Chesapeake’s premier new home community! This beautifully crafted single-story home offers seamless open-concept living with luxury finishes, including a gas fireplace and a smart home package. The spacious living area flows effortlessly into the beautiful kitchen -complete with a large center island, stainless-steel appliances, and premium quartz countertops-making it perfect for entertaining. Retreat to the oversized primary suite featuring a spa-inspired bath with a frameless shower, a private water closet, and a huge walk-in closet. With three additional bedrooms, a second full bath, tankless water heater, and durable Hardiplank siding, this home is designed for comfort and efficiency. Enjoy the friendly, amenity-rich community with walking trails, a fire pit, and easy access to Chesapeake’s vibrant waterfront, festivals, and nearby beaches.

200 Kwanzan Court, South Chesapeake

1340 Cypress Pl, South Chesapeake
$416,250
3 Beds ⋅ 2.1 Baths ⋅ 10639011 MLS
Experience style, space, and convenience in this updated 3-bedroom, 2.5-bath home in Chesapeake's desirable Greenbrier area. The kitchen features granite countertops, stainless steel appliances, a pantry, breakfast bar, and ample cabinet space. Multiple living areas, including a living room and family room, offer flexibility for everyday living, work, or entertaining. The dining room showcases charming plank paneling for added character. Enjoy the fenced backyard with a deck ready for gatherings and a storage shed for extra space. Newer siding and roof enhance both value and curb appeal. Conveniently located near Chesapeake City Park, shopping, dining, major interstates, neighborhood lakes, and scenic walking paths. Don't miss this opportunity, schedule your private showing today!

1340 Cypress Pl, South Chesapeake

2021 Ferguson Loop, South Chesapeake
$755,000
4 Beds ⋅ 2.1 Baths ⋅ 10637855 MLS
This one is a hole-in-one and truly in a league of its own! The wow factor begins before you even step inside with a putting green in the side yard. Out back, enjoy your own private retreat featuring a saltwater pool with heater and chiller, custom wood-burning pizza oven, generously sized backyard, and inviting outdoor living spaces. Inside, the chef's kitchen shines with a massive island offering abundant storage, Wolf gas range, wall oven, built-in beer tap, designer lighting, and wide-plank hardwood flooring. The luxurious primary suite offers dual walk-in closets and a spa-inspired bath. Oversized secondary bedrooms also feature walk-in closets, while the finished heated and cooled garage provides incredible flex space. Meticulously maintained and exceptionally appointed, this standout property delivers the complete package. Call today to tour!

2021 Ferguson Loop, South Chesapeake

916 W Saint Brides Road Unit W, South Chesapeake
$850,000
6 Beds ⋅ 4 Baths ⋅ 10635980 MLS
Enjoy peaceful country living in this spacious 6-bedroom home on 3 acres with modern updates and room to spread out. Oak hardwood floors flow throughout the main level, which features a formal dining room and an open kitchen with stainless steel appliances, a center island, and a coffee station overlooking the great room with an electric fireplace. The first floor also has a bedroom and a full bath, which could make a great guest room or a dedicated home office. Upstairs, there are 4 generously sized bedrooms, two full bathrooms, plus a finished room over the garage with a private (3rd) full bath, perfect as a media room, guest suite, (6th Bedroom), or playroom. Outside, enjoy an above-ground pool (two years old) with deck, mature fig, blueberry, cherry, and mulberry trees, 3 established chicken coops with 10 hens producing a half dozen eggs a day. There is also a 23x15 workshop, and wide-open backyard views that complete the country lifestyle.

916 W Saint Brides Road Unit W, South Chesapeake

520 Dunning Lane, South Chesapeake
$535,000
3 Beds ⋅ 2.1 Baths ⋅ 10635653 MLS
Prepare to fall in love with this Elegant and meticulously maintained gem located in the gated 55+ resort style community of Eagle Pointe in Southern Chesapeake. Sitting on a premium home site with water views and no neighbors behind you, you will be impressed with the spacious and flowing Hamilton Floorplan. This lovely Home boasts a vaulted Great Room with gas fireplace and an Eat in Kitchen that opens to the bright and sunny Florida Room that offers peaceful and tranquil water views. Additional Details: Primary Suite with jetted tub and separate step in tile surround shower, 2 nice sized secondary bedrooms with ceiling fans, 2nd floor Loft overlooking the 1st floor, Formal Dining Room, lots of storage space, blinds throughout, central vacuum, patio, and a 2 car attached garage with opener and work sink. Eagle Pointe Bay Club amenities include a heated indoor pool and hot tub, outdoor pool, fitness center, billiards room, game room, library, catering kitchen, and celebration room.

520 Dunning Lane, South Chesapeake

1117 Camelot Court, South Chesapeake
$385,000
4 Beds ⋅ 2 Baths ⋅ 10635113 MLS
Spacious ranch living with room to spread out, both inside and out. Situated on a large cul-de-sac lot, this well-maintained home offers very generous room sizes throughout, including 4 spacious bedrooms, a large living room, dining room, and an inviting eat-in kitchen refreshed with new flooring, painted cabinetry, new backsplash, recessed and pendant lighting, and new appliances (2024). The sunroom provides additional flexible living space filled with natural light, perfect for relaxing or entertaining. Other recent updates including new carpet (2023), new flooring in the foyer and sunroom (2024), and water heater (2018) Outside, the oversized detached garage offers an incredible combination of workshop space and added storage. Whole house generator conveys as-is and is not currently connected to propane. Well pump located in garage conveys as-is.

1117 Camelot Court, South Chesapeake

1390 Sebastian Court, South Chesapeake
$799,900
5 Beds ⋅ 4 Baths ⋅ 10634982 MLS
The Macon Model at Stoney Creek by Wetherington Homes blends refined design, luxury finishes, and modern functionality in a beautifully crafted open-concept layout. Gorgeous hardwood floors flow throughout the home, creating warmth and timeless sophistication. The chef-inspired kitchen is the heart of the home, featuring expansive prep space, a Butlers pantry, abundant cabinetry, high-end appliances, wine fridge, and a large island ideal fo rentertaining! Seamlessly connected dining and living spaces offer effortless flow for everyday living and hosting alike. The spacious owner's suite provides a peaceful retreat with a spa-inspired bath and generous closet space. Secondary bedrooms plus versatile loft space offer flexibility for guests, office space or additional living needs. Exceptional craftsmanship, thoughtful storage solutions, and elevated details throughout make this stunning MOVE-IN READY home truly stand out!

1390 Sebastian Court, South Chesapeake

961 Speight Lyons Loop, South Chesapeake
$600,000
4 Beds ⋅ 2.1 Baths ⋅ 10634733 MLS
Located in the sought-after Grassfield High School District, this beautifully maintained 4BR, 2.5BA Chesapeake home offers the warmth of southern charm, the confidence of major updates, and the comfort of everyday living. Relax on the wraparound front porch or enjoy the backyard deck with wooded privacy. Inside features engineered hardwood floors, spacious family room with wood-burning fireplace and built-ins, formal dining room, and flexible front room for office or playroom. The updated eat-in kitchen opens to the family room and is a chef’s delight with generous prep space, island, pantry storage, and ample cabinetry. Upstairs includes spacious FROG, dual staircase, generous bedrooms, and primary suite with walk-in closet and dual vanity. Major updates include roof (’24), crawlspace encapsulation (’20), fence (’20), water heater (’20), porch railing/post wrap (’23), garage opener (’23), HVAC (’14), and first-floor furnace (’26). Near dining, shopping, and interstates. Move-in ready!

961 Speight Lyons Loop, South Chesapeake

504 Sydenham Boulevard, South Chesapeake
$580,000
4 Beds ⋅ 2.1 Baths ⋅ 10634574 MLS
Beautifully redone and move in ready, this home blends updated finishes with functional living throughout. The first floor features durable LVP flooring and a recently renovated kitchen with quartz countertops, open shelving, farmhouse sink, LG stainless steel appliances, and a spacious walk in pantry. Custom trim details, shiplap accents, wainscoting, and dining room molding add character and charm throughout the home. Bathrooms have also been recently updated for a fresh, modern feel. Upstairs offers generously sized bedrooms with plenty of space to spread out. Enjoy the backyard oasis featuring a saltwater pool, pergola, playhouse, a chicken coop, and recently expanded concrete patio space perfect for entertaining and relaxing. Conveniently located near Edinburgh Shopping Center, grocery stores, dining, and everyday conveniences. An assumable loan with a rare 2.99% interest rate may also be available for qualified buyers.

504 Sydenham Boulevard, South Chesapeake

317 Sawyers Mill Crossing Crossing, South Chesapeake
$520,000
4 Beds ⋅ 2.1 Baths ⋅ 10634685 MLS
Welcome to 317 Sawyers Mill Crossing- where everyday living feels effortless. Imagine hosting holiday dinners that flow seamlessly from the dining room to the kitchen, enjoying slow mornings in the breakfast area, and gathering with friends in the living room before heading outside for summer barbecues under not one, but two pergolas on the spacious deck. Situated on a nicely sized lot in Chesapeake’s sought-after Grassfield school district, this well-maintained home offers 4 bedrooms, 2 full and 1 half bath, and 2,710 sq ft of comfortable living space. The first-floor primary suite feels like its own retreat with a luxurious walk-in shower, dual vanities, and a spacious walk-in closet. Complete with granite countertops, a spacious room over the garage, a 2-car garage, backyard storage shed, and neighborhood amenities including a pool, clubhouse, playground, and easy interstate access.This home offers the lifestyle today’s buyers are looking for. Seller open to $5k credit with full price offer.

317 Sawyers Mill Crossing Crossing, South Chesapeake

1616 Whittamore Road, South Chesapeake
$460,000
4 Beds ⋅ 2.1 Baths ⋅ 10633922 MLS
Enjoy the peaceful feel of country living without sacrificing city convenience. Tucked away in a quiet setting yet minutes from shopping, dining, and major routes, this home offers the space and lifestyle you’ve been looking for. Located in the highly desired Hickory School district near Battlefield Golf Club and Fentress Airfield. The open layout features spacious living and dining areas flowing into a large kitchen with granite countertops and stainless steel appliances. The primary suite offers a large bedroom, walk-in closet, and bath with double sinks, jetted tub, and separate shower. Secondary bedrooms are generously sized with walk-in closets. Enjoy the large fenced backyard complete with a playset that conveys and spacious shed, perfect for entertaining, relaxing evenings, pets, and play.

1616 Whittamore Road, South Chesapeake

908 Wheatfield Way, South Chesapeake
$648,000
4 Beds ⋅ 2.1 Baths ⋅ 10633581 MLS
Welcome to this beautifully maintained home ideally positioned along the protected Chesapeake Arboretum, offering 48 acres of scenic trails, natural beauty, and peaceful backyard views. Thoughtful updates include hardwood stairs, Anderson windows on the east/south (2025) side, gutter guards, and a new water heater, along with a roof (2012), 3-zone HVAC (2010), and luxury vinyl plank/carpet (2018). The driveway has been extended with added concrete, along with a newly added concrete back patio. The converted garage provides flexible space perfect for a game room, guest suite, or media area. Step outside to your private oasis featuring a saltwater pool, steps, safety cover, pump, and transferable warranties. Entertain year-round on the spacious patio with built-in lighting, pergola and beautifully landscaped yard designed for both relaxation and gatherings.

908 Wheatfield Way, South Chesapeake

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