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$995,000
6 Beds ⋅ 4 Baths ⋅ 10645935 MLS
An exceptional opportunity to own a Stephen Alexander custom home in Greystone, one of Chesapeake's premier luxury communities where homes are rarely available. This expansive executive residence blends timeless craftsmanship with the space, flexibility, and resort-style amenities today's luxury buyers seek. A first-floor bedroom with an adjacent full bath offers versatility for guests, a home office, or multi-generational living. The primary suite is a true retreat with a fireplace, sitting area, and four closets. Enjoy a private backyard oasis featuring an in-ground pool, hot tub, screened porch, gazebo, fire pit, privacy fence, irrigation well, and expanded parking for a boat or RV. Scenic walking paths enhance this sought- after community. Significant recent investments include a new roof (2026), three HVAC systems, an encapsulated crawl space, new hardwood flooring, updated bath vanities, freshly painted kitchen cabinetry, and a new oven. Schedule your private showing today!

821 Redleafe Circle, South Chesapeake

$435,000
3 Beds ⋅ 2.1 Baths ⋅ 10646107 MLS
The Welcome to your next home, where every day feels a little more special. Nestled in the highly sought-after Bryan's Cove community, this beautiful home offers more than just a place to live—it offers a lifestyle defined by comfort, convenience, and connection. Enjoy added privacy with a peaceful wooded backdrop and no rear neighbors. With a low condo fee, no flood insurance requirement, and zoning for the highly desirable Grassfield school district, this home truly checks all the boxes. Bryan's Cove is known for its scenic surroundings and exceptional amenities, offering the perfect blend of tranquility and everyday convenience. Residents enjoy access to a community dock, dog park, fitness center, clubhouse, and swimming pool. Nearby, you will find Publix, lots of other shopping and several restaurants, Tidewater Community College, and quick access to Interstates 64 and 264 makes commuting and daily errands effortless, while parks, recreation, and local attractions are all close by. Inside, you'll find a warm and inviting floor plan designed for both comfortable living and effortless entertaining. The spacious kitchen serves as the heart of the home, featuring a large center island with seating, abundant prep space, and a gas range that will delight home chefs. Every room has been thoughtfully designed to create a welcoming atmosphere where family and friends can gather and lasting memories can be made. Opportunities like this don't come along often. If you've been searching for a home in an exceptional community with outstanding amenities, top-rated schools, and a private, natural setting, this is one you won't want to miss. Schedule your private showing today and experience everything this remarkable home has to offer.

1741 Fortune Terrace, South Chesapeake

$725,000
5 Beds ⋅ 3.1 Baths ⋅ 10646366 MLS
See features sheet & survey attached — you’ll be amazed by this NEW custom home by Overholt Contracting (40+ yrs)! Must see now: modern floorplan with 2 spacious primary suites (or use one as a game room), 4 large bedrooms, first-floor home office, high-end kitchen & baths with quartz, freestanding tub + tiled shower, smart-home Wi-Fi, and full landscaping with sod. Sited on almost 1/2 acre in Hickory (Chesapeake) on city/county septic & water — NO HOA, additional buildings allowed, room for pool, boat or RV. James Hardie siding, carriage garage door with glass, brushed concrete patio. Closing cost assistance available with preferred lender Wes Flowers, Southern Trust. Also see something you would love to have but it’s not here. Contact me and my builder will have his design team work on it. He is easy going and ready to make your new home all about you!!! You wont find another build of this quality at this amazing price.

343 Ewell Lane, South Chesapeake

$649,900
4 Beds ⋅ 3.1 Baths ⋅ 10646358 MLS
LUXURY COASTAL RIVERFRONT LIVING W/ AT IT'S FINEST! Breathtaking sunrises, sunsets & an effortless Coastal Lifestyle on the Elizabeth River. Elegant Craftsman style home w/ First Floor Primary Suite. Luxurious Chefs kitchen, expansive island w/ bar seating, granite counter tops & extended 48' wood cabinets w/ extra storage. Comfortable open living spaces w/fireplace, 8 ft doors, high ceilings & wood floor package. First Floor FLEX SPACE for 5th bedroom/Home Office. Spacious owner's suite w/ Spa Concept bathroom, tile floors, glass shower + custom walk-in closet. ENTERTAINERS DELIGHT! Screened in porch, professionally landscaped yard w/ OLP Lighting Design, fenced in yard + 2 car detached garage. All the BELLS & WHISTLES you can Dream of. Community amenities include waterfront Gazebo w/ access to deep water, Kayak Launch, Clubhouse w/ pool, Fitness Room, Green Spaces & Nature Preserves w/ private trails throughout. TURNKEY & MOVE IN READY. WELCOME HOME!

224 Wildlife Trace, South Chesapeake

$329,400
2 Beds ⋅ 2.1 Baths ⋅ 10646125 MLS
Spacious 1,870-square-foot, 2-bedroom townhome in a four-unit building. Peacefully set among trees, the home offers a feeling of privacy. BRAND NEW air conditioning unit will keep you cool on hot summer days. The versatile first-floor office can easily serve as a third bedroom, guest room, or flex space. Beautiful wood floors throughout the lower level offer aesthetic appeal and simplify cleaning and maintenance. An oversized kitchen features a generous pantry, breakfast area, and plenty of cabinet space. Sliding glass doors open to a private, fenced in patio, wonderful for relaxing or entertaining. Upstairs, you'll find two generously sized primary suites, each with its own private full bathroom, providing comfort and privacy for residents and guests alike. A spacious second floor laundry room includes washer and dryer hookups and a utility sink for added convenience. Community amenities include a sparkling swimming pool, grounds maintenance, trash pickup, and sewer, all included with the HOA. Ideally located in the sought-after Greenbrier area, with easy access to interstates, shopping, and dining. Quick move in available, come see this beauty today!

514 Trellis Trail, South Chesapeake

$395,000
3 Beds ⋅ 2.1 Baths ⋅ 10646171 MLS
Welcome to this luxury townhome in the desirable Coleman Farms neighborhood. Built in 2021, this home offers 3 bedrooms, 2.5 bathrooms, 1,936 square feet of thoughtfully designed living space, an upstairs loft, and a two-car garage. The open-concept main level features a modern kitchen with stainless steel GE appliances, including a microwave, dishwasher, and electric range, along with a Samsung Bespoke refrigerator. All appliances convey, including the Samsung washer and dryer.Upstairs, the spacious primary suite features a huge walk-in closet and a private en-suite bath. The secondary bedrooms also offer walk-in closets, providing ample storage throughout the home. A versatile loft adds additional flexible living space.Enjoy the fully fenced backyard with custom pavers and low-maintenance turf. Additional highlights include EV charging readiness and HOA amenities such as a clubhouse, pool, and fitness center. Conveniently located near shopping, dining, and commuter routes.

1201 Jadens Way, Central Chesapeake

$325,000
2 Beds ⋅ 2.1 Baths ⋅ 10645916 MLS
Loan is assumable at 5.625% interest rate. Enjoy low-maintenance living in this move-in ready townhome-style condo in the desirable Warrington Hall community! Conveniently located just minutes from shopping, restaurants, parks, and major interstates, you'll have easy access to everything Chesapeake and Hampton Roads have to offer. Community amenities include a clubhouse, pool, tennis courts, and ground maintenance for a carefree lifestyle. Inside, the spacious layout features a kitchen with abundant cabinetry, all appliances, pantry, and a breakfast bar which opens up to the dining room. The inviting family room provides lots of natural lighting, and there is a convenient powder room for guests. Upstairs, both spacious bedrooms offer walk-in closets and private ensuite bathrooms. The primary suite features a dual vanity and tub/shower combination. Step outside to enjoy your own private patio, perfect for morning coffee or relaxing at the end of the day. Just move in and start enjoying all this community has to offer!

1115 Warrington Boulevard, South Chesapeake

$285,000
2 Beds ⋅ 2.1 Baths ⋅ 10645264 MLS
This beautifully updated 2 bedroom, 2.5 baths, 2 story condo features 2 full primary ensuite bedrooms w/updated bathrooms including new sinks, counter, vanities, lighting, & toilets. In addition, brank new LPV flooring, new upgraded carpet 2nd floor, fresh paint throughout, new kitchen cabinets, new granite counters and new stainless-steel appliances create a clean and modern feel. There is a reserved parking spot plus plenty of visitor parking. Enjoy maintenance free living with condo fees, that include access to clubhouse, community pool maintenance & trash pickup. Convenient Greenbrier location near shopping, dining, easy I-64 access. This move-in ready home offers comfort and convenience and makes this home a must see!

2351 Old Greenbrier Road, Central Chesapeake

$568,000
4 Beds ⋅ 2.1 Baths ⋅ 10645016 MLS
*Seller to contribute an amount of $7K toward the Buyer's allowable closing costs and prepaid expenses subject to lender guidelines with an acceptable offer.* Welcome to this beautifully maintained 4-bedroom, 2.5-bath home offering an open-concept floor plan designed for comfortable everyday living and effortless entertaining. Conveniently located near shopping, dining, and with easy interstate access, this home combines comfort with convenience. Relax and unwind on the spacious deck while enjoying peaceful views of the pond and the surrounding wildlife. The generous primary suite features a large walk-in closet, providing plenty of storage space. The well-appointed kitchen includes a gas range, a large pantry, and ample workspace for cooking and gathering. Located in the highly sought-after Chesapeake School District, this home also offers numerous valuable upgrades, including a new roof (2024), HVAC system (2024), and water heater (2021). Additional features include solar panels for energy efficiency, an irrigation system with a dedicated well, a security system, and the washer and dryer, all of which convey with the home.

1311 Piedmont Arch, South Chesapeake

$609,900
4 Beds ⋅ 3.1 Baths ⋅ 10644569 MLS
100% move-in ready in the Grassfield school district! This open floor plan offers quality finishes throughout. Hardwood flooring runs throughout the main living areas. The first-floor office/study has direct access to the wraparound front porch. The family room opens to the dining area and spacious kitchen featuring granite countertops, white soft-close cabinets, a large island, stainless steel appliances, and a walk-in pantry. Enjoy the private, fully fenced backyard with a custom paver patio. The room over the garage is a private guest suite with a full bath and separate access from the foyer. Upstairs also offers a loft, 2 spacious bedrooms, and the primary suite with a large walk-in closet, soaking tub, oversized tiled shower with custom glass enclosure, and private water closet. No HOA. Convenient to schools, shopping, dining, and major commuter routes.

1933 Reefwood Road, South Chesapeake

$795,000
6 Beds ⋅ 3.1 Baths ⋅ 10643149 MLS
Well-maintained, spacious home on a prime lot in the beautiful Riverwalk community. New Roof, all new Windows, new paint interior and exterior, and new carpet in 2026! Beautiful wood floors in living and dining areas. Six bedrooms, 3 full and 1 half baths. Designed for those who love to entertain, the expansive floor plan offers elegant gathering spaces, abundant natural light, a formal butler station off the dining room. and exceptional flow throughout. The spacious eat-in kitchen and bar-top seating area open to the inviting family room with a cozy fireplace. Three additional bedrooms are located on the second level, including a versatile FROG that can serve as the 6th bedroom, home office, or recreation room. Current cooktop and built-in microwave to be replaced; buyer can choose. Large back deck with gas hookup. Residents of Riverwalk enjoy exceptional neighborhood amenities, including walking trails, a community pool, boat ramp and dock, playground, and a popular summer swim team. This is a wonderful opportunity to own a meticulously cared-for home in one of Chesapeake’s most desirable communities.

804 River Strand, South Chesapeake

$500,000
5 Beds ⋅ 3 Baths ⋅ 10644216 MLS
Situated on a corner lot in sought after Culpepper Landing, this spacious home is ready for new owners to make it their own. A formal living and dining room, both with hardwood floors greet you as you enter. A large living room with gas fireplace opens to the spacious kitchen that includes tons of cabinet space and granite counters. The eat-in kitchen provides access to the large fenced-in backyard, great for entertaining. A bedroom and full bath are also located on the first floor. Upstairs, the primary bedroom includes an attached bath with double vanity, soaking tub and walk-in shower. Three more bedrooms and an impressive laundry room complete the second level. The attached 2-car garage provides excellent additional storage space. Neighborhood amenities include a clubhouse, exercise room, playgrounds, pool and more!

700 Canoe Street, South Chesapeake

$468,900
3 Beds ⋅ 2.1 Baths ⋅ 10643511 MLS
Make this your first stop! Beautiful maintained townhome located in the highly sought-after Hickory School District. This move-in ready home features a spacious first-floor primary suite with a large walk-in closet, 9-foot ceilings, quartz countertops, stainless steel appliances, and upgraded luxury vinyl plank flooring throughout. Upstairs, you'll find two generously sized bedrooms, each with its own walk-in closet, plus a walk-in attic offering abundant storage. Additional highlights include a one-car garage, a private patio, and low-maintenance living. Conveniently located near Route 168, shopping, dining and the Coast Guard Chesapeake Annex. Don't miss the opportunity to make this beautiful home yours! Newly painted throughout home, electric fireplace to convey. ***Seller needs rent back ~ Nov 1st for new build completion.

1915 Canning Place, South Chesapeake

$682,500
5 Beds ⋅ 3 Baths ⋅ 10643877 MLS
This well maintained all brick home with 2-car side loading garage with long driveway and 1/3 acre beautifully landscaped lot is situated on a cul-de-sac in Great Bridge. Open floor plan features Huge kitchen with quartz counter tops and overlooks Fam. Rm. FR has wood burning FP which is also plumbed for gas. In addition to the 5 bedrooms on 2nd floor, there is a 6th bedroom/ office with adjacent full bath on first floor. Recent updates include replacement windows, roof, water heater, garage door and leaf filter gutters. New 3 ton upstairs HVAC installed in Sept. 2026. Award winning Cheshire Forest community amenities include clubhouse, pool, tennis/ pickleball court , parks, and playgrounds. Seller to provide 1 year home warranty. The screened porch with concrete floor overlooks the beautiful backyard.

810 Hedgerow Court, South Chesapeake

$674,900
5 Beds ⋅ 2.1 Baths ⋅ 10642890 MLS
Convenient location. 20 min to Downtown Norfolk. 35 min to NAS Oceana, Dam Neck & beaches. 20 min to Norfolk Int Airport. Over 10 grocery stores in a 5 mile radius. 5 min to Hickory H.S., 1 of the BEST in Hampton Roads. Easy access to Chesapeake Bypass, I-64, I-264, & I-464. This property is a gardener's dream sequenced for near year round color. Back yard oasis includes a hot tub, goldfish pond and six foot privacy fence. Two patios are connected by a master-crafted paver walk-way. Oversized garden shed helps keep garage clutter free. In ground sprinkler system fed by well water to keep watering cost low. Two outdoor water taps fed by the well & two additional taps fed by city water. Tank-less water heater provides endless hot water. The oversized Primary Bedroom includes two walk in closets. One large walk-in closet features two side cubby units for storage. The other walk-in closet is medium sized with plenty of storage space. Washer & dryer are on the second floor for convenience to bedrooms.

707 River Gate Court, South Chesapeake

$699,000
4 Beds ⋅ 3.2 Baths ⋅ 10642808 MLS
A Full Acre of Land in the Heart of Southern Chesapeake.... Two Primary Suites. Room for Everyone! Over 3,600 sf. Renovated 4-bedroom 3 full baths and 1 1/2 baths home on a beautiful piece of land in Chesapeake — brand new carpet, all freshly painted. The space, privacy, and flexibility that rarely come together at this price point. Two primary suites, one up and one down, give you real options: multigenerational living, long-term guests, or a main-level owner's retreat. The downstairs in-law suite/owners suite has its own private entrance — space for older parents, adult kids, or a home business with client access that never touches your living space. The renovated kitchen features stainless steel appliances and opens to living areas built for gathering. The upstairs primary offers double sinks and a large walk-in closet. A mudroom with half bath handles the daily traffic so the rest of the house stays put together. Outside is where this property separates itself. A wrap-around deck surrounds the above-ground pool — your built-in venue for summer weekends. The roundabout driveway and attached 2-car garage mean parking is never a problem, whether it's a cookout for twenty or just everyday life. And the full acre gives you room to add, expand, or simply breathe — no neighbors ten feet from your window. Homes with this much land, this much flexibility, don't sit long in Chesapeake. Schedule your showing today. Sellers are motivated. Some images are digitally staged.

1833 Benefit Road, South Chesapeake

$725,000
5 Beds ⋅ 2.1 Baths ⋅ 10642786 MLS
One of a kind property in Hickory area of Chesapeake with 2 (YES TWO) SFH that are legally deeded, WATERFRONT (ocean access) ~3.5 ac lot, with no neighbors in sight! Main house is over 3,000 sqft 5/2.5. Smaller house about 1200 sqft, 2/. Both have newer systems and New Roofs. Each home has its own Septic/Well system & pumped in 2024-large house/2025-small house. Property backs to 60 ft of riverfront that leads through the sounds and into the ocean. The main farmhouse has modern amenities but the old charm and character with original hardwoods, curved arches and entry ways, Juliet Balcony overlooking estate, 3rd floor finished attic bonus room and solid walk down basement foundation that can be turned into a finished room or used for storage. This home is solid and well maintained, being sold as is, seller to make no repairs. Call today for your private showing!

112 Station Road, South Chesapeake

$584,999
6 Beds ⋅ 4.1 Baths ⋅ 10642445 MLS
Rare opportunity to own a beautifully updated 6-bedroom, 4.5-bath home featuring a private, fully equipped in-law suite for multigenerational living, extended family, guests, rental income, or a private home office. The main residence offers 5 spacious bedrooms, 3 full baths, and a stunning remodeled kitchen with quartz countertops, sleek high-gloss cabinetry, stainless steel appliances, and space for a large center island. The separate in-law suite lives like its own home, complete with an open loft-style bedroom, 1.5 baths, walk-in closet, full-size laundry, upgraded kitchen with quartz counters and stainless appliances, and generous living space. Recent upgrades include renovated baths, new windows, patio doors, and Nest thermostats. Step outside to your backyard oasis featuring an 8-foot in-ground pool with newer liner, filter, and pump, plus a built-in deck bar ideal for entertaining. Conveniently located near shopping, dining, schools, military bases, beaches, and major commuter routes.

501 Thornloe Ln Lane, South Chesapeake

$613,900
4 Beds ⋅ 2.1 Baths ⋅ 10641071 MLS
Welcome home to this stunning like new construction in the highly sought-after Great Bridge School District! Move-in ready and thoughtfully designed, this beautiful home offers the freedom of no HOA and all the modern finishes today's buyers are looking for.Step inside to discover a bright, open-concept floor plan perfect for both everyday living and entertaining. The spacious first-floor office provides an ideal work-from-home space or flex room to fit your lifestyle. The gourmet kitchen is sure to impress with elegant quartz countertops, a classic subway tile backsplash, white shaker cabinetry, and a full stainless steel appliance package.Throughout the home, crown molding adds a touch of sophistication, while the energy-efficient tankless water heater provides modern convenience. Retreat outdoors to enjoy the fully fenced backyard, perfect for pets, play, or relaxing evenings. Make this home yours today.

1229 Waters Road, South Chesapeake

$410,000
4 Beds ⋅ 2.1 Baths ⋅ 10641084 MLS
Welcome home to this beautifully maintained 4-bedroom, 2.5-bath home in Chesapeake! Built in 2018, this two-story residence offers over 2,000 sq ft of modern living space. The open-concept layout features a bright living area that flows into the dining space and kitchen—perfect for entertaining or relaxing at home. Upstairs includes four spacious bedrooms, highlighted by a private primary suite with a spa-like bath and ample closet space. Additional rooms offer flexibility for guests, a home office, or playroom. Situated on a corner lot in an established neighborhood, this home provides both privacy and convenience. Close to shopping, dining, major interstates, and military bases. Move-in ready and full of charm—don’t miss this Chesapeake gem!

4101 2nd Street Unit A, Central Chesapeake

$553,900
3 Beds ⋅ 3 Baths ⋅ 10641052 MLS
Enjoy peaceful country living on 1.77 acres in the highly sought-after Hickory School District! This charming 3-bedroom, 3-full-bath home offers plenty of space both inside and out, making it perfect for those seeking privacy, comfort, and room to roam.Step inside and discover a welcoming open layout designed for everyday living and entertaining. The spacious heated sunroom deck provides the perfect spot to relax year-round. Huge pantry storage room off kitchen to keep those grocerie store runs to a minimum. The expansive 1.77-acre lot includes a chicken coop, large detach garage, fenced area, carport, and open fields making this property ideal for hobby farmers, homesteaders, or anyone looking to embrace a more self-sufficient lifestyle. With plenty of room for gardening, recreation, and outdoor activities, the possibilities are endless. The back half of detached garage needs work, but has lots of potential for a nice workshop, game room, mancave, apartment, etc.

2420 Mount Pleasant Road, 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.