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828 Helmsdale Way, South Chesapeake
$410,000
3 Beds ⋅ 2.1 Baths ⋅ 10654442 MLS
GREAT BRIDGE + HUGE BACKYARD + NO HOA! This beautifully maintained 3 bedroom, 2.5 bath home offers the space, features and location you've been looking for! Step inside to a bright, inviting interior filled with natural light and featuring updated flooring, granite countertops and a wood-burning fireplace, just right for cozy evenings. Upstairs, you'll find a spacious primary suite, along with two additional bedrooms. Step outside and discover one of this homes' standout features - a HUGE, fully fenced backyard with plenty of room to entertain, play, garden or simply relax on the patio. The 2-car garage provides additional parking and storage. Conveniently located near shopping, dining, parks and major roadways. Well maintained, move-in ready and NO HOA! Solar panels are paid for! Schedule your showing and come see what makes this Great Bridge home a must-see!

828 Helmsdale Way, South Chesapeake

620 Emerald Court, South Chesapeake
$399,900
4 Beds ⋅ 2.1 Baths ⋅ 10654385 MLS
Welcome to your next great opportunity! This spacious 1,917 sq ft ranch home offers 4 bedrooms and 2.5 bathrooms with a flexible floor plan designed for effortless daily living. The functional layout includes a large Finished Room Over Garage (FROG) as the 4th bedroom— could also be used as an office, media room, or flex space. Inside flows seamlessly to the back deck, overlooking an expansive 0.389-acre lot with abundant outdoor space and a large storage shed. Complete with a 1-car attached garage, this property offers incredible potential! Bring your vision—with a touch of sweat equity and minor cosmetics, this solid home will truly shine and build instant equity. Excellent location with convenient access to major interstates, regional bases, dining, shopping, and entertainment. Call today to schedule your private showing!

620 Emerald Court, South Chesapeake

744 Helmsdale Way, South Chesapeake
$425,000
4 Beds ⋅ 2.1 Baths ⋅ 10654335 MLS
Discover timeless charm in this beautiful, traditional home located in the heart of Chesapeake. Featuring 4 bedrooms, 2.5 bathrooms, and a spacious two-story layout, this home includes a bedroom with its own en suite bath, making it great for guests or added privacy. Gather around the cozy fireplace on cool evenings, or enjoy casual meals in the bright breakfast area. Step outside to a fully fenced backyard, great for entertaining, pets, or relaxing outdoors. Recent upgrades, including new siding and roof (2021) and a remodeled primary bathroom (2025), enhance both the home's beauty and value. An attached garage and attic complete this exceptional property. Don't miss your opportunity to make this Chesapeake gem your own!

744 Helmsdale Way, South Chesapeake

609 Fairfield Drive, South Chesapeake
$849,900
4 Beds ⋅ 2.1 Baths ⋅ 10654253 MLS
The perfect farmhouse that’s a mix of privacy and closeness to local amenities. Sitting on approx 3 acres in Albemarle Farms, this home offers the updates you've been looking for. Step inside to a bright, welcoming interior with engineered hardwood floors, fresh paint throughout, new trim, and a beautifully updated kitchen. Completed in 2025, the kitchen features all-new cabinetry, quartz countertops, a large island, white stone backsplash, new appliances, and a new sink and faucet. Just beyond, the great room is centered around a new stone fireplace and mantle, while the 4-season room offers a flexible space to relax, work, or enjoy views of the property. Upstairs, the primary suite features a soaking tub and walk-in shower, with two additional bedrooms and bonus space offering plenty of flexibility. Major improvements include new heating and cooling units, new ductwork upstairs and downstairs, a new tankless water heater, and new downstairs subfloor. Outside is where this property really shines, with a saltwater in-ground pool, expansive deck, covered rear porch, circular driveway, and plenty of room to enjoy the wooded setting. An oversized garage with a finished room above adds even more usable space. Located in the Hickory school district with no HOA, this is a home with room to settle in, spread out, and enjoy both indoors and out. Incentives may be available through preferred partners. Contact listing agent for details and eligibility.

609 Fairfield Drive, South Chesapeake

2924 Taylor Road, West Chesapeake
$384,000
3 Beds ⋅ 2 Baths ⋅ 10654099 MLS
Rare GEM in the Western Branch school district! This meticulously maintained brick ranch was renovated in 2021 and offers 3 bedrooms, 2 baths, and a functional floor plan with spacious living and dining rooms, a sunken family room, good-sized bedrooms, and a primary bedroom with a private bath. Features include newer LVP flooring, modern updated bathrooms, and a stylish kitchen with granite countertops, stainless steel appliances, and newer cabinets. Two wood-burning fireplaces have been maintained and used during winter. Enjoy the screened-in back porch, large backyard, and wooded views. Major improvements include a new roof ('21), new hot-water heater tank and gutters ('26). Two parcels total approximately 0.78 acre: a 0.45-acre homesite and a rear parcel of approximately 0.33 acre. Attached 1-car garage with ample room to expand parking. NO HOA! Move-in ready and close to bases, interstates, shopping, and restaurants. Schedule your showing today!

2924 Taylor Road, West Chesapeake

4504 Greendell Road, West Chesapeake
$335,000
3 Beds ⋅ 1.1 Baths ⋅ 10654025 MLS
Make this your first stop! This beautifully maintained brick ranch in Western Branch offers the perfect combination of comfort, functionality, and outdoor living. Featuring 3 bedrooms, 1.5 bathrooms, spacious living areas, and a well-appointed kitchen, this home is move-in ready and has been exceptionally cared for by its owners. The open layout creates a great flow for everyday living and entertaining, while the large family room provides plenty of space to gather with family and friends. Major improvements include an encapsulated crawl space, whole-house generator system, and a backyard oasis complete with an above-ground pool. The oversized backyard offers plenty of room to relax, entertain, or enjoy outdoor activities. With pride of ownership evident throughout and desirable features that are hard to find, this is a home you'll want to see in person!

4504 Greendell Road, West Chesapeake

2949 Prince Of Wales Drive, West Chesapeake
$539,000
5 Beds ⋅ 2.1 Baths ⋅ 10653953 MLS
Welcome to this charming 5-bedroom home, perfectly situated in a wonderful, established neighborhood in Chesapeake. If you appreciate a home with character and room to grow, this is the perfect canvas for your vision. The heart of the home features a kitchen designed for those who love to cook, offering an abundance of counter and cabinet space, plus the convenience of a double oven. You’ll love spending quiet evenings by one of the two cozy fireplaces or unwinding on the beautiful, screened-in porch that overlooks a private, tree-lined backyard. With spacious bedrooms throughout, this home offers plenty of room for everyone to enjoy. Bring your personal touch and make this well-loved house your own!

2949 Prince Of Wales Drive, West Chesapeake

302 Honey Locust Way, South Chesapeake
$635,000
4 Beds ⋅ 2.2 Baths ⋅ 10653782 MLS
Former Home-A-Rama award-winning home with character you simply don't find every day. Tucked away on a .43-acre cul-de-sac lot, this 3-story Victorian-style home offers approximately 3,100 sq. ft. of living space and a wrap-around porch. Inside you'll find hardwood floors, generous living and dining spaces, custom details, two fireplaces and two staircases. The gourmet kitchen features quartz countertops, black stainless appliances, custom cabinetry, island and pantry. Spacious bedrooms lead to an impressive primary suite with walk-in closet, ensuite bath and fireplace. A third-level bonus space offers flexibility for an office, study or workout room. Outside, an in-ground saltwater pool, multi-level deck, gazebo, fire pit and expansive backyard create a setting for entertaining or relaxing. A truly unique home ready for its next chapter!

302 Honey Locust Way, South Chesapeake

808 Bay Laurel Court, South Chesapeake
$634,000
4 Beds ⋅ 3.1 Baths ⋅ 10653860 MLS
Welcome home to this beautiful brick home, ideally situated on a large corner lot in a cul-de-sac in Chesapeake’s desirable Cedarwood community. Offering more than 3,000 square feet, this move-in-ready home features an open, light-filled floor plan with tall ceilings and gorgeous wood flooring. The spacious kitchen flows seamlessly into the living area, creating the perfect setting for entertaining. Relax beside the wood-burning fireplace surrounded by charming built-in shelving, or enjoy the backyard with its generous deck, gazebo and delightful garden house. Two primary bedrooms with private full baths provide wonderful flexibility for guests or multigenerational living. Other highlights include updated bathrooms, upgraded windows and architectural shingles. New refrigerator installed in 2026. All appliances convey. A two-car attached garage and additional street parking, conveniently located near shopping, dining and sought-after Chesapeake schools. Schedule your private tour today!

808 Bay Laurel Court, South Chesapeake

832 Woodrow Court, South Chesapeake
$475,000
4 Beds ⋅ 2 Baths ⋅ 10653661 MLS
Tucked away at the end of a quiet cul-de-sac, this exceptionally clean and carefully maintained 4-bedroom home offers comfortable living and added peace of mind with a newly installed roof with warranty. The spacious bedroom over the garage provides flexibility, while the sunroom adds another 180 square feet of living space overlooking a private, fully fenced backyard. Start your morning in the kitchen’s inviting breakfast area, unwind beside the wood-burning fireplace, or enjoy outdoor gatherings in the backyard. A separate utility room, efficient geothermal heating and cooling, and low-maintenance exterior trim add everyday convenience. The seller will provide a clear termite and moisture letter. Located within the Great Bridge school attendance area, this move-in-ready home is priced to sell and ready for its next chapter. Put this one on your showing list!

832 Woodrow Court, South Chesapeake

1741 Taft Road, South Chesapeake
$999,999
4 Beds ⋅ 2.1 Baths ⋅ 10653479 MLS
Three wooded acres. A saltwater pool. Five garage bays. Room for the boat, RV and workshop. And no HOA. 1741 Taft Road offers a combination that’s increasingly hard to find in Southern Chesapeake. The approx. 3,700-sq.-ft. home features 4 bedrooms, 2.5 baths and a welcoming wraparound porch. Inside, the kitchen is equipped with matte white Café appliances including a gas range, while the spacious living room centers around a wood-burning fireplace. Upstairs are 4 generously sized bedrooms, including a primary suite with 2 walk-in closets. A finished third floor adds 2 large bonus rooms, creating flexible space for a nursery, home office, gym, studio or private retreat. Outside, an approx. 32,000-gallon saltwater pool and composite deck anchor the backyard, with major pool components updated in 2025–26. A heated 2-car attached garage is joined by a 3-bay detached garage/workshop with propane heat plus mini-split heating and cooling. Covered paved storage accommodates a boat, camper or RV, with a pole barn and additional storage shed adding even more versatility. The acreage continues beyond the rear gate into the woods, where walking trails extend the ways to enjoy the property. Extensive paved parking and a private setting complete a property that offers breathing room without giving up convenient access to Chesapeake.

1741 Taft Road, South Chesapeake

224 Northview Drive, South Chesapeake
$485,000
3 Beds ⋅ 2.1 Baths ⋅ 10653649 MLS
Renovated brick ranch in the Great Bridge school district, in established Chesapeake Colony. Less than half a mile to Great Bridge Middle, about a mile to Great Bridge Primary and under 2 miles to Great Bridge High. This single-level 3-bedroom, 2.5-bath home offers 1,854 sq ft with hardwood floors, two wood-burning fireplaces and a renovated kitchen with Corian countertops, stainless steel appliances and LVP flooring. Both full bathrooms have been fully renovated with natural stone flooring, custom tile and updated vanities. System updates include roof (2010) HVAC (2010) and tankless water heater (2025). Natural gas, a generator hookup and an oversized attached garage add everyday convenience. The 0.34-acre lot is set among mature trees, Japanese maples and azaleas. Out back: a privacy-fenced yard with a two-level composite deck and low-voltage lighting, a Wellis hot tub, a gazebo with swing, a pea gravel patio, a separate gated dog run and a powered 10x14 shed with loft and workbench. Irrigation and a double-wide driveway with parking for five complete the package. Minutes to Great Bridge shopping, dining and Chesapeake Regional Medical Center.

224 Northview Drive, South Chesapeake

4207 Coffman Boulevard, West Chesapeake
$394,000
4 Beds ⋅ 2 Baths ⋅ 10653672 MLS
Well-maintained home, on over half an acre lot in desirable Chadswyck Terrace. Inviting layout is ideal for everyday living & entertaining, with a spacious living room flowing into the dining area & kitchen. Wood-burning fireplace adds warmth & character. The kitchen boasts stainless steel appliances, abundant counter space, & an adjoining utility room that can also serve as a convenient mudroom. Private primary suite features an ensuite bath, creating a comfortable retreat. Above the garage, a versatile bonus room can serve as a bedroom, office, playroom, or guest space. Enjoy the expansive backyard & generously sized deck, perfect for relaxing, grilling, or entertaining. Property extends beyond the fenced area, offering room to expand the enclosure. Updates include a new roof in 2020 & HVAC system in 2018. Close to shopping, dining, the mall, & interstate access. Solar panels will be paid off at closing; the electric bill is $9/mo & VA Assumable loan option with a 2.5% interest rate!

4207 Coffman Boulevard, West Chesapeake

2804 Meadow Wood Drive W, West Chesapeake
$450,000
4 Beds ⋅ 2.1 Baths ⋅ 10653521 MLS
Embrace timeless Colonial charm with beautifully updated spaces in this inviting home set on a spacious .75-acre corner lot. Inside, a warm and welcoming family room with a cozy fireplace creates the perfect gathering space, while the sunlit eat-in kitchen features granite countertops, a charming bay window, and new LVP flooring that continues into the laundry room. Enjoy the added value of two fully renovated bathrooms, thoughtfully updated with today’s style and comfort in mind. The spacious primary suite offers two walk-in closets and a private bath, creating a relaxing retreat at the end of the day. Host family and friends in the formal dining room, or unwind in the newly renovated sun porch overlooking the peaceful outdoor surroundings. A deck provides even more space to relax, entertain, or enjoy the .75-acre setting. A large side-load garage, additional parking, and a versatile shed/workshop offer plenty of room for storage, hobbies, or projects. An encapsulated crawl space and negotiable furnishings add even more convenience and value. Located in a peaceful community with easy access to shopping, dining, and major routes, this home blends classic character, modern updates, and everyday functionality. Schedule your tour today and see everything this special property has to offer.

2804 Meadow Wood Drive W, West Chesapeake

1914 Keeter Run, South Chesapeake
$437,500
4 Beds ⋅ 2.1 Baths ⋅ 10653149 MLS
Welcome home to Greenbrier! This beautifully maintained, move in ready home is tucked away on a desirable cul-de-sac in the heart of Chesapeake. Featuring numerous recent updates, you can move in with confidence and enjoy! The kitchen was updated in 2023 with new cabinets, countertops, and appliances. All bathrooms were refreshed in 2024 with new vanities, sinks, tubs, toilets, flooring, and paint. Major updates include a roof (2017), fence (2021), HVAC furnace (2025), condenser(2026), and water heater (2026). The first floor offers a spacious foyer, open living and dining areas, plus flexible bonus space great for a home office or playroom. Upstairs features a large primary suite with private bath and walk-in closet, three additional bedrooms, and a spacious shared bath. Conveniently located near Greenbrier shopping, dining, interstates, and local attractions. Don't miss your opportunity to make this home yours!

1914 Keeter Run, South Chesapeake

3708 Riverwood Crescent, South Chesapeake
$775,000
5 Beds ⋅ 2.1 Baths ⋅ 10653033 MLS
Welcome to 3708 Riverwood Crescent! Situated on approx. 3 acres in sought after Chesapeake 23322, this nearly 3,000 sq. ft. home offers space, privacy & extensive updates! Enjoy a private backyard retreat with pool, screened porch & updated deck. Inside features a remodeled kitchen with quartz countertops, mostly stainless steel appliances, soft-close cabinetry, recessed lighting, hardwood & luxury vinyl plank flooring, plus new carpet upstairs, and solar hallway lighting. Updated baths include new countertops, toilets, fixtures, ceramic tile, tub/shower & an enlarged porcelain-tiled primary shower. Major improvements include dual-zone HVAC (2019/2021), 2024 water heater, water softener, encapsulated crawl space with pump & dehumidifier, replaced exterior/garage doors, vinyl windows & 2011 roof with 50-yr warranty. Shed and lawn tractor conveys! A rare combination of acreage, updates, pool & location; come see it!

3708 Riverwood Crescent, South Chesapeake

1910 Hallmark Way, South Chesapeake
$998,895
5 Beds ⋅ 3.1 Baths ⋅ 10652907 MLS
Experience luxury living in this one-of-a-kind Chesapeake retreat, nestled on a 3-acre lot in the Grassfield School District. This custom-built home blends modern comfort with timeless charm, offering an open-concept first floor design for today's lifestyle. The spacious family room flows seamlessly into the remodeled 2024 kitchen, with direct access to the back deck for everyday relaxation or entertaining guests. Choose between two generous primary suites. First floor primary suite features a gas fireplace, dual closets, and a sitting/office area. Second floor primary suite privately located above 3-car garage, offering separation from the additional upstairs bedrooms. Enjoy abundant space for hobbies and storage with two powered sheds, plus peace of mind from the new encapsulated crawl space with vapor barrier. Major upgrades, including the roof, HVAC, and kitchen in 2024, ensures comfort and efficiency for years to come. This exceptional property delivers a rare combination of privacy, space, and freedom with no HOA restrictions, making it a true Chesapeake gem. **Bookshelves do not Convey**

1910 Hallmark Way, South Chesapeake

311 Lancing Way, South Chesapeake
$619,000
4 Beds ⋅ 2.1 Baths ⋅ 10652797 MLS
Welcome to 311 Lancing Way! This beautiful 4-bedroom, 2.5 bath home in Chesapeake's desirable Grassfield area features a backyard oasis with a large, 33,000-gallon lagoon-style saltwater pool, 8-ft deep end, variable-speed pump, water feature, plumbing for a future waterslide/waterfall, and a buried pool drain line with pump-controlled discharge to the street. The pool is surrounded by a beautiful stamped concrete, complemented by a spacious screened porch with dual variable-speed fans, a poolside bar shed, and a garden shed with front and rear access. Inside, enjoy programmable dual-zone A/C with independently controlled thermostats and an automatic generator transfer switch. Parking for 4 cars, including an oversized 2-car garage, PLUS additional concrete parking for a boat or 2 more vehicles! No HOA fees! Conveniently located near Grassfield schools, shopping, dining, parks, major interstates, and military installations throughout Hampton Roads. Schedule your private showing today!

311 Lancing Way, South Chesapeake

152 Mann Drive, South Chesapeake
$460,000
3 Beds ⋅ 2 Baths ⋅ 10652558 MLS
Welcome to 152 Mann Drive in the heart of Great Bridge! This well-built brick ranch offers the perfect blend of charm and modern updates. Nearly every major improvement was completed in 2023, including luxury vinyl plank flooring, a fully updated kitchen, renovated bathrooms, HVAC system, and roof—giving you peace of mind for years to come. You’ll appreciate the seamless flow of the floor plan, designed for both everyday living and easy entertaining. Just off the kitchen, a cozy wood-burning fireplace creates a warm and inviting ambiance—perfect for relaxing evenings at home. With solid construction, stylish updates, and plenty of potential to make it your own, this is one you won’t want to miss!

152 Mann Drive, South Chesapeake

2708 Meadow Drive W, West Chesapeake
$539,000
5 Beds ⋅ 2.1 Baths ⋅ 10652573 MLS
Welcome home to this spacious, established-neighborhood ranch offering 5 bedrooms, 2½ baths, and 2,200+ square feet on just over a half-acre lot along the Elizabeth River. Enjoy peaceful water views from the covered porch—a wonderful spot for morning coffee, relaxing evenings, or entertaining guests. Inside, the home offers comfortable one-level living with plenty of space for family, guests, or a home office. Thoughtful updates and features add both comfort and convenience, including: • New roof installed in 2022 • Tankless water heater • Mini-split HVAC systems for added comfort and flexibility • Emergency generator hookup • Pre-wired surround sound in the LR and porch And for buyers looking for additional value, the sellers are offering concessions with a full-price offer. If you’ve been looking for a home that combines space, water views, modern conveniences, and an established neighborhood setting, this one deserves a closer look.

2708 Meadow Drive W, West Chesapeake

3132 Benefit Road, South Chesapeake
$1,000,000
6 Beds ⋅ 3 Baths ⋅ 10652479 MLS
Open house Sun 10/18 1-3pm Modern Farmhouse Charm Meets Turnkey Living in Desirable Chesapeake! Discover the modern farmhouse you’ve been dreaming of, where peaceful country living meets thoughtful, top-to-bottom renovation. Set on serene acreage with panoramic wooded views. It embraces the natural surroundings. This beautifully refreshed home is ideal for extended family/multi generational living. Natural light fills the home, showcasing new flooring, fresh interior paint, updated lighting, and beautifully renovated bathrooms. The completely redesigned custom kitchen is the heart of the home, featuring quartz countertops, ceramic backsplash, abundant prep space, an inviting eat-in area and a KitchenAid appliance suite, ideal for everyday living and entertaining. The expansive living area offers plenty of room to gather, while the renovated wood-burning fireplace creates a cozy focal point with a new firebox, flue, chimney cap, and Buck Stove-style insert. Step onto the Trex deck with PVC railing and enjoy peaceful wooded views from the living space, primary suite or deck. The primary suite is a true retreat, featuring a custom-tiled shower with built-in bench and generous niche, deep soaking tub, double vanity and ceramic tile flooring. The expansive custom closet with built ins provides all the space you have been longing for. Additional improvements include an encapsulated crawlspace with dehumidifier, new septic system designed for 10 occupants, finished room over the garage with generous storage, updated downstairs ductwork, new interior and exterior doors and hardware, new lighting throughout, and a freshly graded crushed-aggregate driveway. The painted brick exterior adds a fresh, modern look while preserving brick’s timeless durability and character. Best of all, the home features a highly energy-efficient geothermal HVAC system. From the crawlspace to the exterior, virtually nothing has been overlooked. Renovated by New Again Houses VB. It offers the feel of quality new construction without sacrificing character, space or setting. See it today!

3132 Benefit Road, South Chesapeake

309 Barcelona Drive, South Chesapeake
$539,500
4 Beds ⋅ 3 Baths ⋅ 10651803 MLS
Great buy in Grassfield schools. Lovely front porch large home nestled in Las Gaviotas golf course community. Gardeners paradise in the backyard with wild flowers, strawberries and so much more. Deluxe playground and lots of fun built-in for backyard summer days. Expansive kitchen with center island, eating area and built-in desk. Modern farmhouse touches throughout. Cozy brick fireplace and built-in bookcases, shiplap half wall really add to the charming family room and separates this home from all of the others. Freshly painted in Sherwin Williams Accessible Beige. New carpet upstairs. Spacious bedrooms with a lot of closet space. Big walk up attic is amazing for storage. Finished room above the garage with separate staircase would make a great movie room or playroom. You have got to see this beauty and make it HOME.

309 Barcelona Drive, South Chesapeake

Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.