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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

$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

$449,900
5 Beds 2 Baths 10646209 MLS
Spacious all-brick ranch offering 5 bedrooms in a highly desirable school district! Nice home features new flooring and a flexible floor plan designed for comfortable living. Enjoy a formal living room, formal dining room, and a cozy den with a wood fireplace. The eat-in kitchen offers plenty of cabinet space and includes a pantry for additional storage. The converted garage provides a versatile bonus space perfect for a home office, playroom, or hobby area. The first-floor primary bedroom adds convenience, while the room over the garage offers even more living space. Step outside to a privacy-fenced, spacious backyard complete with a deck, ideal for entertaining, relaxing, or enjoying outdoor activities. A rare opportunity to own a home with space, functionality, and an excellent location!

1024 Weeping Willow Drive, South Chesapeake

$404,900
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

$427,000
4 Beds 2.1 Baths 10645995 MLS
Welcome to your dream home in Chesapeake! This meticulously maintained end-unit condo blends modern luxury with effortless living, offers 4 bedrooms, 2.5 bathrooms, and beautifully upgraded living spaces. Go inside to an airy open-concept layout with vaulted ceilings, crown molding, and luxury vinyl flooring. Enjoy upgraded recessed lighting, pendant lights, and modern ceiling fans. The chef's kitchen, renovated in 2023, features new cabinets, granite counters, and premium stainless steel appliances. Major systems have been updated, including a water heater (2022) and HVAC (2024). The 1st floor ensuite is a private retreat with custom built-in shelves, walk-in closet, and spa-like bathroom with double sinks and a jetted tub. Upstairs, 2 additional bedrooms share a dual-entry bathroom with double sinks, offering great privacy for family or guests, and a large bonus loft area. Parking includes an attached garage and 2-space driveway. Welcome home to style, space, and convenience!

713 Tiffany Green Court, South Chesapeake

$329,000
2 Beds 2.1 Baths 10645916 MLS
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

$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

$435,000
4 Beds 2 Baths 10645687 MLS
Welcome to this inviting 4-bedroom ranch in the sought after Mill Creek neighborhood. Freshly painted throughout with brand new carpet and a new roof, this home is truly move-in ready. Enter into a bright living room featuring vaulted ceilings and a cozy wood-burning fireplace, seamlessly opening to the fully remodeled kitchen. The kitchen shines with white shaker soft-close cabinets, quartz countertops, and stainless steel appliances. Two bedrooms sit just off the living room, accompanied by a beautifully updated hall bathroom and laundry room. The spacious primary bedroom offers a remodeled en-suite bathroom and a generous walk-in closet. The FROG provides flexibility as a 4th bedroom, guest space, or bonus room. Out back, enjoy a wood deck overlooking an above-ground pool and a peaceful backyard with views of the wooded area maintained by the Army Corps of Engineers along the Dismal Swamp Canal. The property extends about 10 ft beyond the back fence line. Don't miss this one.

500 Willow Bend Drive, South Chesapeake

$580,000
4 Beds 2.1 Baths 10645079 MLS
Welcome to this practically brand-new 4BR/2.5BA home in Chesapeake that still has that new home smell! Immaculate and move-in ready, this home shines with crisp finishes and thoughtful design throughout. The chef friendly kitchen features a large island, soft-close cabinetry, beautiful countertops, a stylish backsplash, and plenty of space for cooking, gathering, and entertaining. Upstairs, the spacious primary suite offers both a walk-in closet and an additional oversized closet, while the generously sized secondary bedrooms all feature large closets. A versatile flex space provides room for a home office, playroom, or cozy sitting area. The 2-car garage includes an EV charger, and the manageable backyard offers just the right amount of outdoor space to enjoy without the upkeep. Conveniently located near restaurants, breweries, coffee shops, shopping, and interstate access, this home combines modern comfort with everyday convenience. This is one you won't want to miss. Welcome HOME!

933 Brenner Road, 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

$300,000
3 Beds 2.1 Baths 10645613 MLS
Welcome Home! Thoughtfully updated throughout, this home features brand-new LVP flooring, carpet, fresh paint, blinds & added attic insulation (2026). Updated cabinets, granite countertops, light fixtures, bathroom vanities, and faucets. Major improvements provide peace of mind, including replacement windows and sliding patio doors (2021), a new roof (2017), and a water heater (2018). The spacious layout offers generously sized bedrooms, abundant closet space, and the convenience of a one-car garage. Outside enjoy the fully fenced backyard with a storage shed that backs up to the Indian River Park & inground firepit. The washer and dryer convey, making this home truly move-in ready. With its extensive updates, functional layout, and low-maintenance living, this is one you won't want to miss!

16 Farington Circle, Central 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

$569,900
4 Beds 2.1 Baths 10645253 MLS
Move in ready and less than 5 years old with impressive builder upgrades. The gourmet kitchen boasts of high-end appliances including induction stovetop, wine fridge and huge walk-in pantry. This kitchen features elegant quartz countertops, artistic backsplash with large bar area completely open to living area with fireplace. A luxurious primary suite with spa inspired bath features huge shower and quartz vanity. A tasteful neutral palate with wide planked flooring and tons of natural light throughout the home. Enjoy almost half acre fenced in backyard wired for 50 amps and home is plumbed for gas. Conveniently located near dining, shopping , military bases and interstates. Schedule your showing today to make this wonderful house YOUR HOME! Seller will consider closing cost assistance with full price offer.

240 Hurdle Drive, 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

$295,000
2 Beds 2 Baths 10645362 MLS
Welcome HOME to this gorgeously remodeled, from top to bottom 2BR/2BA one-story ranch house. It has EVERYTHING you've been searching for: open concept layout, large updated windows, new luxury LVP flooring throughout, modern light fixtures, custom tile work, freshly painted, you name it! Completely NEW spacious chef’s kitchen shines with expensive QUARTZ countertops, large island with built-in cabinetry, soft-close white cabinets extending up to the ceiling with LED lighting, and NEW stainless steel appliances. Spacious Primary suite with 2 closets, and a beautifully remodeled bath with a new vanity, tiled floor, new tub, floor-to-ceiling designer tile surround, separate toilet area, and deep linen closet. Second Bedroom with big closet. Contemporary remodeled Hall Bathroom with contemporary floating vanity, new toilet, and tiled shower with designer accents. Spacious laundry room, instant hot water heater, long driveway for multi-car parking or RV parking, and fenced backyard complete the package! NO HOA fees, and no flood insurance required. Some photos were virtually staged or digitally enhanced for marketing purposes to help buyers visualize the property’s potential. Schedule your showing today to make this house YOUR HOME!!

1002 Mayfield Avenue, Central 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.