Refine Search
Sort by
$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

$425,000
3 Beds 2.1 Baths 10646473 MLS
Welcome to this beautifully maintained 3 bedroom, 2.5 bath home. Step inside to a bright, open floor plan featuring rich dark wood floors that flow throughout the main living areas. The stunning kitchen is designed to impress with custom cabinetry, upgraded appliances, and plenty of space for cooking and entertaining. The inviting great room is the heart of the home, complete with gas fireplace and custom built-in shelving, creating the perfect space to relax or gather with family and friends. Upstairs, you'll find spacious bedrooms, including a comfortable primary suite, offering room for everyone to spread out. Outside, enjoy your own private patio, ideal for morning coffee or simply unwinding after a long day. Residents enjoy fantastic community amenities, including a pool, clubhouse, and exterior grounds maintenance, allowing you to spend more time enjoying your home and less time on upkeep. BRAND NEW ROOF (July 2026). Don’t miss your opportunity to make this your next home!

515 Sweet Leaf Place, South Chesapeake

$750,000
5 Beds 3 Baths 10646148 MLS
Welcome home to this stunning Stephen Alexander "Caramel Cottage" in the highly sought-after Hanbury Woods — one of Great Bridge's most desirable communities. This 5-bedroom, 3-bath home checks every box: a first-floor bedroom and full bath perfect for guests or multigenerational living, 10' ceilings, rich hardwood floors, and an open-concept living area anchored by custom built-ins and a cozy gas fireplace. The chef's kitchen is the heart of the home — 42" white cabinetry, an oversized island, stainless appliances, and a walk-in pantry give you space to cook, entertain, and gather. Step out to the three-season Eze-Breeze porch and take in a private backyard with a large paver patio — your own retreat for morning coffee or evening wine. Upstairs, the primary suite is a true escape: spa-like bath, tiled shower, soaking tub, dual vanities, and a huge walk-in closet. Two more bedrooms and a spacious media/flex room round out the second floor, giving everyone room to spread out. This is a premium, highly requested model loaded with upgrades throughout — a rare find at this price point. Located in the heart of Great Bridge with top-rated schools and easy access across all of Hampton Roads, this home offers the space, quality, and location today's buyers are looking for. Homes like this in Hanbury Woods don't last — schedule your showing today

1153 Edinburg Parkway, South Chesapeake

$739,900
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
STUNNING EXECUTIVE SMART HOME IN PREMIER RIVERFRONT COMMUNITY W/ NATURE PRESERVE! DESIGNED FOR BOTH COMFORT & EFFICIENCY, THE CRAFTSMAN STYLE HOME W/ FF PRIMARY BEDROOM & UPGRADES GALORE! Coastal themed Craftsman Style Luxury home w/ a charming wrap around front porch. Elegant Home w/ an open concept & comfortable open living spaces w/ 8 ft doors, high ceilings + Beautifully appointed WOOD FLOORING. Culinary Kitchen features extended island, Granite Counter tops, Bar Seating. Sprinkler system &well. (see add list of upgrades). Includes PREMIUM ION SOLAR PANELS (2023) to be paid in FULL by the seller @ closing! Approx. $33/month in income generated through SREC (Solar Panel Renewable Energy Certifications). Owners monthly electric bills are approx. $33/month. Carefree amenities; Waterfront Gazebo on deep water, Kayak Launch, Clubhouse w/ pool.... Green Spaces & winding trails throughout. WELCOME HOME!

224 Wildlife Trace, South Chesapeake

$597,740
3 Beds 3 Baths 10646287 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2205 Edwin Drive, South Chesapeake

$700,000
5 Beds 2.1 Baths 10645293 MLS
Tucked away on a quiet cul-de-sac, this beautifully maintained custom home offers the perfect combination of quality construction, thoughtful upgrades, and everyday comfort. Built in 2004 and offering approximately 3,300 square feet, this all-brick home features 5 bedrooms, with 4 conveniently located on the first floor, providing exceptional flexibility for families, guests, or multi-generational living. From the moment you step inside, you'll appreciate the soaring cathedral ceilings, spacious living areas, and inviting gas fireplace that create a warm and welcoming atmosphere. The private primary suite offers a relaxing retreat with a jetted soaking tub and generous walk-in closets. One of this home's standout features is the incredible backyard privacy. Whether you're enjoying your morning coffee, hosting family and friends on the large deck, or simply unwinding after a long day, you'll love the peaceful setting and the feeling of having your own private oasis. This home also offers valuable upgrades that provide peace of mind for years to come. A whole-house generator ensures you're prepared and comfortable during unexpected power outages, while the encapsulated crawl space reflects the care and attention given to maintaining the home, helping protect the structure and enhance energy efficiency. An irrigation system keeps the lawn looking its best with minimal effort. Located in the highly sought-after Hickory school district, this home delivers the rare combination of timeless all-brick construction, flexible living space, exceptional privacy, and important long-term investments that today's buyers appreciate. If you've been searching for a home that is as practical as it is beautiful, this one is not to be missed. Some photos have been virtually staged.

1104 Arabian Arch, South Chesapeake

$788,990
5 Beds 3.1 Baths 10646215 MLS
Introducing the Tillman, a spacious home that offers both comfort and style. With 5 bedrooms, 3,5 bathrooms, and a 2-car garage. Upon entering the Tillman, you'll be greeted by a large, welcoming dining room that seamlessly flows into the expansive kitchen. The kitchen features a generous center island, ideal for meal prep or casual dining, and opens to a spacious family room, creating the perfect space for entertaining. A conveniently located powder room is just off the main hallway, adding to the home's functionality. The first floor also boasts a luxurious primary suite, providing a private retreat with a massive walk-in closet, a large double vanity, and a private water closet for ultimate convenience and privacy. Upstairs, you'll find four additional bedrooms. The second floor also features two bathrooms and a large loft area that could serve as a separate lounge, playroom, or additional living space. Photos and renderings are from builder's library, actual finishes and features may vary.

325 Riverview Road, South Chesapeake

$610,000
5 Beds 2.1 Baths 10646157 MLS
Tucked away on a quiet cul-de-sac and sitting pretty on a corner lot, this updated 5-bedroom, 2.5-bath home has room for everyone & everything. From the moment you walk in, you'll feel the perfect blend of comfort and function this home was designed for. Cozy up in the den by the fireplace, host holidays in the separate dining room, or get work done in the private office—there's a space for every part of your life. The kitchen shines with recessed lighting and a pantry, while the living room offers even more room to gather. Retreat to the primary suite, your own private escape complete with a second fireplace, a sitting area, and a spacious walk-in closet. The spa-like primary bath doesn't disappoint either, featuring a walk-in shower, soaking tub, dual sinks, and a linen closet for extra storage. Step outside onto your deck—ideal for weekend BBQs,or just soaking up some sunshine in your own private space. 2-car garage & shed means storage is never an issue.

807 Gresham Way, South Chesapeake

$330,000
2 Beds 2.1 Baths 10646077 MLS
This end-unit townhome in the desirable Riverwalk community offers a functional layout, thoughtful updates, and exceptional amenities. Upstairs you will find two spacious bedrooms, both with ensuite bathrooms. The open-concept first floor seamlessly connects the living room, dining area, and kitchen, with durable LVP flooring throughout the main level and continuing upstairs. The kitchen is equipped with granite countertops and stainless steel appliances, while the gas fireplace adds warmth and charm to the living space. Enjoy relaxing on the screened porch overlooking your fenced backyard. Major updates have already been completed, including a new HVAC system (2025), water heater (2024), and a roof approximately seven years old. Additional highlights include an attached garage and access to Riverwalk's outstanding community amenities, including a pool, tennis courts, and clubhouse. Conveniently located near shopping, dining, and major commuter routes, make this one your next home!

312 Esplanade Place, South Chesapeake

$389,900
3 Beds 2.1 Baths 10645889 MLS
This adorable 2-story, Townhouse-style, end-unit condo is conveniently located in sought after Hampshires @Greenbrier. The 1st floor features an open-concept layout consisting of an inviting foyer that flows into the formal dining room, Primary bedroom w/ensuite bathroom, walk-in closet, updated kitchen boasts quartz counter tops, stainless steel appliances, ample counter space, loads of cabinets for storage, family room w/cozy gas fireplace, utility closet, a powder room off the hallway for guests and access to the attached, 1- car garage & fenced-in patio area. The carpeted stairs lead to the 2nd floor that features 2 additional bedrooms, one w/an en-suite bathroom and large walk-in attic. Highlights include: some hardwood flooring, neutral carpet, lots of natural light & MORE! Neighborhood amenities include: a clubhouse, community pool & ample guest parking. Great central location adjacent to shopping, schools, parks, local beaches & highway access for an easy commute. Welcome Home!

1472 Otterbourne Circle, South Chesapeake

$510,000
4 Beds 2.1 Baths 10645829 MLS
WELCOME HOME! Tucked away on a quiet cul de sac and set on nearly an acre backing to peaceful woods, this beautifully maintained home offers the perfect blend of privacy, outdoor living, and everyday convenience. Whether you’re enjoying your morning coffee in the screened gazebo or entertaining family and friends, you’ll appreciate the peaceful setting this property provides. Inside, you’ll find stainless steel appliances, a spacious walk in pantry, a cozy gas fireplace, and thoughtful updates throughout, including a new roof installed in 2024. A transferable 2-10 Home Warranty provides added peace of mind for the next owner. Conveniently located near Interstate 64, Route 17, shopping, dining, and major military installations throughout Hampton Roads, this home offers the ideal balance of tranquility and accessibility. Don’t miss your opportunity to make this exceptional property your next home. Schedule your private showing today!

104 Bishops Court, South Chesapeake

$619,900
4 Beds 3.1 Baths 10645833 MLS
Come see this beautiful, move-in ready Stephen Alexander home, tucked away on a large private cul-de-sac in the sought-after Grassfield school district. The home’s downstairs features 10 foot ceilings, a family room with crown molding, custom built-ins, and a gas fireplace, and an updated kitchen with a pantry, granite counters, tile backsplash, newer SS appliances (2025), a bar, and a reclaimed barn wood island in the breakfast nook. The large upstairs primary bedroom has His and Hers walk-in closets and a spacious en-suite bathroom with a jetted tub and a separate tiled shower with double showerheads. The FROG serves as the 4th bedroom with its own full bathroom. Additional highlights include a beautiful front porch, a fully fenced-in backyard, a mud room off of the oversized side loading garage with opener, and dual zone HVAC with Nest thermostats. Located in desirable Great Bridge, this home offers easy access to interstates and is just minutes to schools, dining, shopping & more!

901 Hathaway Court, South Chesapeake

$620,000
4 Beds 3 Baths 10645463 MLS
If you've been looking for a home in Cheshire Forest, this is one you won't want to miss! Nestled in one of Great Bridge's most sought-after communities, this beautifully updated and meticulously maintained 4-bedroom, 3-bath home offers approximately 2,673 square feet of thoughtfully designed living space. The bright, functional floor plan is great for everyday living and entertaining, featuring a well-appointed kitchen with a gas range, center island, breakfast area, abundant cabinetry, and seamless flow into the inviting family room with a gas fireplace and formal dining room. The main level also includes a full bathroom with a walk-in shower, a convenient laundry room, and access to the attached two-car garage. Upstairs, the spacious primary suite offers a large walk-in closet and a relaxing ensuite with a soaking tub and separate shower, while two additional generously sized bedrooms share a full hall bathroom. The finished room over the garage provides incredible flexibility as a fourth bedroom, home office, playroom, media room, or guest space. Step outside to a beautifully landscaped, oversized backyard featuring a large deck great for entertaining, outdoor dining, or simply unwinding. Residents enjoy access to community amenities including a clubhouse, pool, playgrounds, and tennis courts, all conveniently located near shopping, dining, parks, and Great Bridge schools. VA assumable loan at 2.25%

819 Keeling Drive, South Chesapeake

$635,000
5 Beds 3.1 Baths 10645747 MLS
Beautiful 5-bedroom, 3-bath home built in 2017 and thoughtfully upgraded, located on a private cul-de-sac with a large, vinyl privacy-fenced yard. Inside, the open floor plan features LVP flooring, a gas fireplace, and a seamless flow into the remodeled kitchen, complete with quartz countertops, custom cabinetry, under-cabinet lighting, and updated appliances (2024). The kitchen complimented with a built-in breakfast nook and custom pantry, while additional custom cabinetry enhances select bedrooms. The primary suite offers a stylishly renovated bath for a true retreat feel. Come outside to enjoy the spacious, private backyard, ideal for relaxing or entertaining with gazebo patio, playground, trampoline and kids pool. The home also includes a finished 3+ car garage with epoxy floors, overhead storage, and a 240V outlet for EV/RV/generator use. Additional features include pre-wired surround sound, Cat5/TV connections in all bedrooms, an irrigation well, attic fan.

3500 Kathys Way, South Chesapeake

$375,000
3 Beds 2.1 Baths 10645496 MLS
Don't miss out on this waterfront Penthouse condo in the heart of Great Bridge. Relax on one of two huge decks overlooking your own private boat slip offering the epitome of coastal living. Once inside, you will find a light-filled open space great for indoor-outdoor living and entertaining. The updates, including the HVAC, low-maintenance LVP flooring, and fresh paint mean you can pack your backs (and life jackets) and move right in! The ample storage indoor and out (don't miss the walk-in attic inside the primary closet) adds practicality and function. The resort-style condo amenities are not to be missed- not only is trash, water, and sewer covered, but you also have a community pool, clubhouse, and ground maintenance to leave all of your free time to enjoy your new coastal lifestyle. The sellers are open to selling the new boat and floating dock for an additional cost.

173 Harbor Watch Drive, South Chesapeake

$699,900
4 Beds 4 Baths 10645397 MLS
Welcome home to Rollingwood Estates in the highly sought after Great Bridge school district. This one owner brick transitional home offers 4 bedrooms and 4 full baths with an open, bright floor plan designed for comfortable living and effortless entertaining. The spacious FROG serves as the fourth bedroom and features its own private full bath, making it ideal for guests or multigenerational living. The kitchen offers Corian countertops, generous workspace and opens to the main living areas. Step outside to your own backyard retreat with a sparkling inground pool, dedicated pool bath, stamped concrete patio, outdoor bar/kitchen area, screened porch, and professionally landscaped yard. A two car attached garage, irrigation well, and thoughtful layout add to the appeal. Offering exceptional value in an established neighborhood, this home is priced to sell and ready for its next owner to make it their own.

837 Greenfield Lane, South Chesapeake

$450,000
3 Beds 2.1 Baths 10645658 MLS
Nestled among mature trees in a sought-after, amenity-rich community, this charming brick end-unit blends warmth with everyday functionality. Step inside to freshly finished hardwood floors on the main level and an abundance of natural light that fills the home with a bright, welcoming feel. The kitchen offers generous counter space and flows seamlessly into the living and dining areas, great for everyday living or entertaining. Upstairs, you'll find brand-new carpet, generously sized bedrooms, a cozy reading nook, and a spacious primary suite featuring a soaking tub, step-in shower, and private water closet. Enjoy a peaceful, tucked-away setting just minutes from shopping, dining, and all the conveniences of this thriving area. The community itself is packed with perks: a large pool, basketball court, tennis/pickleball courts, soccer and volleyball fields, a dog park, scenic trails, and abundant green space. With charm, location, and lifestyle all in one, this home checks every box—schedule your private tour today!

816 Great Marsh Avenue, South Chesapeake

$265,000
3 Beds 2.1 Baths 10644970 MLS
Beautiful townhouse-style condo with attached 1- car garage! The open concept living space downstairs features 9-foot ceilings, new LVP flooring, and a gas fireplace. Packed with style, the kitchen with a two-tiered granite peninsula, beautiful cherry-stained cabinets, and stainless appliances is open to the dining area just off the living room. Carpeted stairs lead to the laundry closet with a washer and dryer to convey is central to the large bathroom with dual vanity sinks shared by the secondary bedrooms. Escape to the oversized primary bedroom with walk-in closets and 9-foot ceilings and tons of natural light. The oversized primary bathroom is complete with a jetted soaker tub and large vanity. Minutes from I-64, I-664, and shopping. Approximately 4 miles from Norfolk Shipyard.

909 Deep Creek Run, South Chesapeake

$644,900
4 Beds 2.1 Baths 10645606 MLS
Ask Agent about a potential VA assumable loan opportunity! Better Than New and Built in 2023, this beautifully and thoughtfully upgraded home offers the benefits of newer construction without the wait. Move-in ready with quick closing available. Bright, open-concept floor plan with abundant natural light. Gourmet kitchen features quartz countertops, oversized island, premium gas range, stainless steel appliances, walk-in pantry, and custom cabinetry. Spacious primary suite includes tray ceiling, dual walk-in closets, soaking tub, tiled shower, and dual vanities. Enjoy covered front and rear porches, extended patio, fully fenced backyard with wooded views, irrigation system, storage shed, custom window treatments, and exceptional attic storage. Convenient to military bases, shopping, dining, and major commuter routes. Trusted lender Steve Hawley (NMLS #1813927) from Southern Trust Mortgage (NMLS #2921) will provide a 1% lender-paid buydown on this listing. Ask Listing Agent for details.

640 Appalachian Court, South Chesapeake

$629,000
6 Beds 3 Baths 10645483 MLS
Rare 6-bedroom opportunity with an ideal multigenerational layout! The first floor features a bedroom, adjacent flex room, and a modified curbless shower, offering exceptional flexibility and accessibility. Beautiful neutral decor, 9' ceilings, hardwood floors, elegant crown molding, and a huge FROG provide room for everyone. The spacious primary suite features hardwood floors and two walk-in closets. Convenient second-floor laundry. Enjoy a large fenced backyard with a powered detached shed and private well for economical lawn irrigation, plus an attached 2-car garage. Meticulously maintained with annual service contracts on the HVAC, tankless water heater, and crawl space. Seller will provide a termite/moisture letter. Convenient to Millville Rd., Veterans Bridge, Shipyard Rd., and major interstates, Portsmouth, Norfolk and Suffolk! Small community vibe with minimal traffic. minimal traffic.

1816 Sunsprite Loop, South Chesapeake

$599,900
4 Beds 2.1 Baths 10645491 MLS
Upon a quiet drive, beneath the sweeping arms of ancient trees, there stands a home of uncommon grace, a residence renewed, refined, and prepared to captivate all who cross its threshold. Golden light spills through the windows, illuminating rooms shaped by thoughtful improvements and timeless comfort. At the heart of the home awaits a magnificent kitchen, adorned with stone countertops, newer cabinetry, gleaming stainless steel appliances, and resilient LVT flooring. It is a setting worthy of grand feasts, intimate gatherings, and countless evenings shared among family and friends. Above the garage rises a vast and versatile chamber—the fourth bedroom. Offering endless possibility as a distinguished home office, private gym, spirited playroom, guest retreat, or sanctuary of quiet thought. Beyond the walls, an expansive backyard unfolds beneath the open sky, inviting celebrations, laughter, peaceful mornings, and memories yet to be written. The home itself has been transformed from within and without, with polybutylene plumbing replaced by PEX, an upgraded electrical panel, most windows replaced, updated lighting and flooring, select exterior doors, siding, trim, and a private well connected to the irrigation system. The roof was replaced in 2014. Set within the highly regarded Hickory school district, this remarkable property is less than one mile from the interstate and only moments from the shopping, dining, and conveniences of Edinburgh. The tree-lined streets and welcoming neighborhood lend the setting an air of distinction rarely found.

712 Woodcott 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.