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$799,990
5 Beds 3.1 Baths 10646719 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.

109 Lilypad Court, South Chesapeake

$625,000
4 Beds 2.1 Baths 10646683 MLS
Nestled in one of the area's most desirable neighborhoods, this stunning home offers over 3000 sq ft of beautifully designed living space. Step inside to an inviting floor plan featuring a spacious living room with soaring cathedral ceilings and a gorgeous stone fireplace. The large eat in kitchen flows seamlessly to the living area with ample cabinetry, a brand-new kitchen sink, plenty of space for entertaining. This spacious 4-bedroom home also features a versatile flex room off the foyer, great for a home office or den. Retreat to the expansive primary suite through French doors, where you will find a generous walk-in closet & a en-suite bath designed for comfort and relaxation. All new windows 2024 and a new HWH. Outside, you'll love the newer deck and fenced in yard. Cheshire Forest residents enjoy exceptional lifestyle amenities including a neighborhood pool, the flying fish swim team, clubhouse, playgrounds, tennis & pickleball courts, pond for fishing & scenic walking paths.

609 Edgewood Arch, South Chesapeake

$719,900
5 Beds 3 Baths 10646613 MLS
Beautiful 5-bedroom, 3-bath home tucked away on a quiet cul-de-sac in the desirable Great Bridge area of Chesapeake. Built in 2018, this move-in ready home features an open-concept floor plan filled with natural light, a spacious living area, and a well-appointed kitchen that's perfect for entertaining. A first-floor bedroom and full bath offer flexibility for guests or a home office. Upstairs, the spacious primary suite provides a private retreat, along with generously sized secondary bedrooms. Situated on nearly half an acre, the backyard offers plenty of room to relax, play, or entertain. Conveniently located near shopping, dining, parks, and major commuter routes. Don't miss this exceptional opportunity—schedule your private tour today!

1021 Mimi Court, South Chesapeake

$734,900
5 Beds 3 Baths 10646525 MLS
There is not enough space to explain how wonderful this home is! A rare sense of privacy meets thoughtful luxury in this upgraded 2022 Grassfield home. Near the end of a cul-de-sac and bordered by protected wetlands and unbuildable parcels on both sides, the lot offers a wooded backdrop that is hard to replicate. The flexible 5-bedroom, 3-bath layout includes two primary suites, one on the first floor, PLUS an office/flex room AND loft-style second living area. Crown molding, hardwood stairs, custom window treatments, a gas fireplace, quartz countertops, stainless appliances, gas cooking, under-cabinet lighting, upstairs laundry, walk-in attic, tankless water heater, smart garage opener, security system, and a custom 36-foot patio add comfort and refinement. Trusted lender Steve Hawley, NMLS #1813927, with Southern Trust Mortgage, NMLS #2921, will provide a 1% lender-paid buydown on this listing. Ask the listing agent for details. Subject to borrower qualification and lender approval.

1741 Watershed Court, South Chesapeake

$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 Edinburgh 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
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

$599,900
4 Beds 2.1 Baths 10646316 MLS
Just six years young, this beautifully maintained home offers thoughtful upgrades and an open layout perfect for everyday living and entertaining. The welcoming entryway features custom shiplap accents, leading into a spacious main living area filled with natural flow. The kitchen stands out with abundant cabinetry, subway tile backsplash with black accents, upgraded light fixtures, gas stove, pantry, and views overlooking the living room with cozy gas fireplace. One of the sellers? favorite features is the backyard, offering privacy with peaceful pond views and open fields beyond. Upstairs, every bedroom is generously sized, while the oversized primary suite includes two walk-in closets and a large walk-in shower. Convenient second-floor laundry and carefully selected colors throughout make this home move-in ready. If you love open-concept living and private backyard views, this home is a must-see!

1668 Teton Court, South Chesapeake

$750,000
6 Beds 3.1 Baths 10646118 MLS
Spacious 4,899 sf lakefront home offering 6 bedrooms and 3.5 baths with an exceptional floor plan designed for comfortable living and entertaining. The expansive 1st floor primary suite provides a private retreat, while a 2nd floor ensuite is great for guests or multigenerational living. A massive great room with stunning lake views serves as the heart of the home, flowing seamlessly to a large composite deck great for outdoor gatherings. The oversized 840 sf attached garage offers ample space for vehicles, storage and hobbies. A walk-up attic provides abundant storage or future expansion potential. With generous living spaces, beautiful water views and a great price, this home is ready to accommodate every lifestyle.

1548 Waterside Drive N, South Chesapeake

$565,000
5 Beds 2.1 Baths 10646268 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

$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 and reflects the care and attention given to maintaining the home. 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

$540,000
5 Beds 2.1 Baths 10646195 MLS
Spacious Home In Wellington! This Beautiful Home Features A Fantastic Open Downstairs Floor Plan That's Perfect For Both Everyday Living And Entertaining. Spacious Primary Suite Downstairs With A Double Vanity & Soaking Bath~Upstairs, You'll Find Four Additional Bedrooms. Enjoy Large Closets, Formal Living And Dining Room With Brazilian Wood Floors And A Family Room Just Off A Great Kitchen Which Has A Lots Of Cabinet Space & Island For The Cook In The Family! Living Room Has A Cozy Gas Fireplace. Covered Deck With Dual Fans Making Outdoor Entertaining Great In The Summer Time ! Large Fenced In Back Yard. Conveniently Located Near Shopping, Dining, Military Bases, And Major Highways! This Home Is A Must See !!

3635 Mardean Drive, West 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

$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

$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

$625,000
4 Beds 2.1 Baths 10645717 MLS
OPEN HOUSE FRI Aug 7 from 5-6 pm & SAT Aug 8 from 12-2 pm ~ Tucked away on a quiet cul-de-sac in the highly sought-after Great Bridge school district, this move-in-ready waterfront home offers nearly 3,000 square feet of thoughtfully updated living space overlooking peaceful water views. Relax on the screened porch while enjoying the privacy of a fully fenced backyard and the freedom of no HOA. Major updates include HVAC (2023 And Serviced), fresh paint, luxury vinyl plank flooring throughout the first floor (2023), updated lighting, water heater (2022), refinished staircase (2022), and an encapsulated crawlspace for clear Termite and Moisture letter. The washer and dryer convey, making this home truly move-in ready. Offering the perfect blend of everyday comfort and tranquil waterfront living, this is an exceptional opportunity to own a beautifully updated home in one of Chesapeake’s most desirable communities.

705 Turnbuckle Court, 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

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.