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2215 Edwin Drive, South Chesapeake
$569,990
3 Beds ⋅ 3 Baths ⋅ 10633649 MLS
JUNE MOVE-IN! 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.

2215 Edwin Drive, South Chesapeake

1302 Sasparilla Court, South Chesapeake
$569,900
4 Beds ⋅ 2.1 Baths ⋅ 10638016 MLS
Come Home SWEET Home to this 2500 Sq Ft 4 Bedroom, 2 1/2 Bath Jewel centrally located in Greenbrier! * BONUS: NO HOA!* Modern Styling includes Beautiful Bamboo floors, Granite countertops, subway tile and upgraded appliances in the Kitchen, and significant Bathroom renovations. Full Laundry/Mud Room with Utility Sink! You will also be AMAZED at the Incredible amount of Storage Space thru-out.. Walk-in PBR Closet AND Walk-in Attic, PLUS 720+ sq ft in the OVERSIZED, Side-load, 2-Car Garage with High Ceilings to boot! HVAC and Windows installed NEW in 2022! HUGE, Above-ground POOL (New Motor 2024, Liner 2025) is OPEN and ready for a COOL DIP just in time for Summer! Plenty of Room still in the Back Yard Oasis for Entertaining on the Large Deck with Pergola and even MORE Grassy recreational space in the .37 Acre Lot in Greenbrier on a Cul-de-sac! Come and SEE for Yourself!

1302 Sasparilla Court, South Chesapeake

314 Middleton Way, South Chesapeake
$569,900
4 Beds ⋅ 3.1 Baths ⋅ 10630426 MLS
Move-in ready 4-bedroom, 3.5 bath home located in sought-after Hickory Manor. Built in 2021, this well-maintained home offers a bright, open concept layout with quartz countertops and spacious living areas, ready for everyday living and entertaining. Features include dual primary suites, one on the first floor and one upstairs, offering flexible living options, along with generously sized bedrooms andample closet space throughout. Enjoy low-maintenance living with front- and side-yard landscaping included, plus access to community amenities such as a clubhouse, fitness center, pool, playground,walking trails, and lakes. The fenced rear patio provides a private outdoor space for relaxing or entertaining, all conveniently located near shopping, dining, and major commuting routes

314 Middleton Way, South Chesapeake

713 Flatrock Lane, South Chesapeake
$569,073
4 Beds ⋅ 2.1 Baths ⋅ 10617476 MLS
Under construction End Unit 2 story townhome condo w/two car front load garage in a 3 unit building! Luxury LVP, wood steps,1st flr:Open floor plan, Kitchen GE Matt White appliances w/refrigerator,Kohler white porcelain sink,pantry,center island w/shiplap,Midnight Blue Cabinets,Champagne fixtures,dining area, living room w/ linear fireplace w/shiplap, covered side entry w/mudroom and 1/2 bath,covered back patio. 2nd flr: Primary w/ceramic floor & shower-2 shower heads,dual sinks, 2 closets, 2 br's & full bath, linen closet, laundry. Quartz tops kitch&all baths, covered entry, Large fenced backyard. Wood shelving all closets.Pet Friendly. Quiet easy lifestyle with the comfort of quality construction & name brand building materials including James Hardie Fire Retardant Fiber Cement Board. Builder 2-10 home warranty, master insurance, trash pick up, private streets, city water/sewer, guest parking, multipurpose trails with lake and fountain. Central Greenbrier location. Only 56 homes.

713 Flatrock Lane, South Chesapeake

1045 Winchester Way, South Chesapeake
$569,000
4 Beds ⋅ 2.1 Baths ⋅ 10645167 MLS
Beautifully updated and impeccably maintained, this exceptional 4BR/2.5BA home offers thoughtfully designed living space in the highly sought-after Kemp Woods neighborhood of Chesapeake. Nestled on a quiet, tree-lined street, this move-in ready home perfectly blends timeless elegance, quality craftsmanship, & modern updates. Step inside to an inviting floor plan filled with natural light, with rich hardwood flooring, elegant plantation shutters, and spacious living areas. Gourmet kitchen is designed to impress, featuring tall cabinetry, built-in appliances, abundant counter space, & oversized breakfast area surrounded by windows that fill the space with natural light. Spacious primary suite is a true private retreat, complete with large walk-in closet & stunning, spa-inspired ensuite featuring beautifully tiled, oversized frameless glass walk-in shower, dual vanity, designer lighting, & luxurious finishes that create a resort-like experience at home. 3 additional generously sized bedrooms. Seamlessly extending the living space outdoors, both the family room and breakfast area open to an expansive multi-level deck overlooking the private backyard. Designed for entertaining and everyday enjoyment, this outdoor retreat offers oversized deck and a hot tub—perfect for summer gatherings, peaceful evenings, or relaxing under the stars. Major improvements provide exceptional peace of mind, including a roof, two-zone HVAC system, & numerous updates completed within the last 5 years, allowing the next owner to simply move in and enjoy. Conveniently located just minutes from Greenbrier’s premier shopping, dining, entertainment, parks, hospitals, and major commuter routes including I-64, this home offers the perfect balance of convenience and the quiet charm of one of Chesapeake’s most established and desirable neighborhoods. 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!!

1045 Winchester Way, South Chesapeake

4105 Margaret Ann Court, West Chesapeake
$567,900
4 Beds ⋅ 2.1 Baths ⋅ 10640809 MLS
Welcome home! Come view this beautiful 4-bedroom, 2.5-bath brick home is nestled in a highly attractive neighborhood. Priced to make it your own!! Inside, you’ll find a spacious family room with a cozy gas fireplace, a large primary bedroom with ensuite, featuring tiled shower. Plantation shutters throughout. The large kitchen offers an island and plenty of storage and room for cooking & entertaining. A versatile room over the garage, provides the flexibility you need for a home office, playroom, or guest space. Step outside to enjoy your private backyard oasis, complete with a full privacy fence, a saltwater pool, and low-maintenance Trex decking—great for gatherings or quiet afternoons at home. A detached garage with electricity adds convenience and additional storage. This home truly has it all—space, comfort, and great outdoor living in a fantastic location! No HOA!

4105 Margaret Ann Court, West Chesapeake

213 Britwell Drive, South Chesapeake
$565,000
4 Beds ⋅ 3 Baths ⋅ 10650209 MLS
An incredible opportunity to own right in the heart of Great Bridge. This property has many standout features. Enjoy 300 amp service to the home and 50 amp service to the side driveway. Bring your recreation vehicles with ease! The luxury of two primary bedrooms, offering room for multigenerational living or a guest retreat. Check out the additional garage with endless possibilities. Workshop, mancave, home gym, extra storage. 2 Hot water heaters - 2018.2 driveways, far right 50 amp service. Home is wired for 300 amp service. Dehumidified & Vapor Barrier in crawl.2 year old gas pack. Exterior doors & Anderson sliding glass door - 2023A home offering this combination of space, flexibility, parking, and electrical capacity is a rare find.

213 Britwell Drive, South Chesapeake

240 Hurdle Drive, South Chesapeake
$565,000
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

1217 Willow Lakes Court, West Chesapeake
$565,000
4 Beds ⋅ 3 Baths ⋅ 10644284 MLS
Immaculate, move-in ready 4BR/3BA ranch nestled on a quiet cul-de-sac offers a perfect blend of comfort & functionality with an open floor plan and easy one level living! Rare in-law suite is great for multigenerational living, guests, or private home office. Spacious living area opens to kitchen with large island and new appliances! Primary Bedroom offers walk-in closet, ensuite with double sinks with shower & soaking tub! Relaxing screen porch overlooks peaceful, private backyard & patio is ready for summer cookouts! Peace of mind with upgraded appliances, water heater, and HVAC components being replaced within past 3 years! Pride of ownership shines throughout! Outside bonus features extended parking pad for RV, boats, etc...Combining immaculate condition, flexible living spaces, and desirable private setting, this beauty is a rare find! Conveniently located minutes to 664 for easy access to all of Hampton Roads with nearby dining, shopping, Western Branch schools!

1217 Willow Lakes Court, West Chesapeake

2825 Ridgeboard Place, South Chesapeake
$565,000
5 Beds ⋅ 2.1 Baths ⋅ 10625792 MLS
Welcome to this beautiful 5 bedroom home located in the highly sought after Grassfield school district. Nestled on a quiet cul de sac, this charming blue home offers great curb appeal with vinyl siding installed just 4 years ago. Inside you are welcomed with an abundance of natural light and a bright, inviting layout. The home has been thoughtfully updated and is completely move in ready for its next owners. With five spacious bedrooms and a large room over the garage, there is plenty of space for everyone whether you need extra bedrooms, a home office, playroom, or bonus living area. Conveniently located near shopping, dining, and major commuter routes while still enjoying the privacy of a cul de sac setting. This home offers space, updates, and location all in one.

2825 Ridgeboard Place, South Chesapeake

270 Carawan Lane, South Chesapeake
$565,000
4 Beds ⋅ 2.1 Baths ⋅ 10624855 MLS
Step into modern luxury in this stunning 4-bedroom, 2.5-bathroom home, where 2007 architecture meets a complete, top-to-bottom renovation. No detail was spared in this transformation, offering the perfect blend of established structure and high-end finishes. At the heart of the home, a gourmet chef’s kitchen shines with premium Cafe appliances, custom cabinetry, and sleek stone countertops.The spacious primary suite serves as a private sanctuary, featuring a spa-inspired ensuite with slate tiling and contemporary fixtures.From the Trex decking to the electric car charger, every inch of this residence has been reimagined for the sophisticated buyer. Move-in ready with new paint & carpet, on a quiet street, this better than new home delivers the ultimate turn-key lifestyle in a prime location. All Great Bridge Schools and quick access to the 168 bypass, this well priced home won't last!

270 Carawan Lane, South Chesapeake

708 Canoe St, South Chesapeake
$564,757
4 Beds ⋅ 3.1 Baths ⋅ 10650738 MLS
**More space. More flexibility. More to love in Culpepper Landing!** If you're looking for a home that gives everyone room to spread out while still bringing people together, this one is worth a look. This 3-story home offers 4 bedrooms, 3.5 baths, and a layout that gives you room to live, work, entertain, and relax. The main level features an open kitchen and living area designed for cooking and entertaining, along with a wonderful sunroom that adds even more space to gather or simply enjoy a little quiet time. Upstairs, you'll find three bedrooms plus a spacious second living area that could be a media room, playroom, office, or whatever your lifestyle needs. The private third-floor suite includes its own full bath and offers even more flexibility for guests or a peaceful retreat. A 2-car garage, generous driveway parking, and fenced backyard round out the home. And outside your front door, Culpepper Landing offers an incredible community lifestyle with the largest community pool in Hampton Roads, clubhouse, fitness center, playgrounds, walking trails, stocked fishing ponds, dog park, and events throughout the year. Convenience matters too. Shopping, dining, major highways, and military installations are all within easy reach, making this a great location for enjoying everything Hampton Roads has to offer. **Come walk through this home and see how much space, flexibility, and opportunity it offers. You may be surprised by just how much this home has to offer.**

708 Canoe St, South Chesapeake

2231 Captiva Lane, West Chesapeake
$564,690
4 Beds ⋅ 2 Baths ⋅ 10594839 MLS
Welcome to The Dogwood, our most popular ranch model! This highly desired floor plan offers 4 bedrooms, 2 baths, and 2335 sq ft. Perfect first home or forever home! The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, a community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. There is truly no better place to feel at home in a floor plan that has all your needs in an exciting new home community! Model Home Open 12-5 PM Daily at 5023 Annapolis, Chesapeake, VA 23321. Builder is offering partial CCA & $15,000 buyer incentive (used at buyer's discretion) when using one of our preferred lenders.

2231 Captiva Lane, West Chesapeake

3313 Dodd Drive, South Chesapeake
$564,000
4 Beds ⋅ 3 Baths ⋅ 10629577 MLS
Welcome Home! Step into this stunning home featuring soaring ceilings and a chef inspired kitchen at the heart of it all. The open floor plan is perfect for entertaining, highlighted by an oversized granite island ideal for gathering. Abundant windows fill the space with natural light, while the cozy fireplace is beautifully anchored by french doors on both sides, leading to a spacious porch-perfect for relaxing or hosting. Gorgeous wide plank hardwood floors flow throughout the main living areas. The oversized room above the garage offers incredible versatility with a full bath-perfect as a guest suite, media room or private retreat. The primary suite is a true escape, complete with a spa like bath. Additional features include a dedicated laundry room and a flex space ideal for a home office. Enjoy outdoor living in the fenced backyard, plus the convenience of a 2 car garage. Community pool and clubhouse! Some photos have been virtually staged.

3313 Dodd Drive, South Chesapeake

2072 River Pearl Way, West Chesapeake
$563,500
4 Beds ⋅ 3.1 Baths ⋅ 10648135 MLS
Welcome to 2072 River Pearl Way in well-established Waterstone; two-story home featuring 2,800 sqft, 4 bdms, 3.5 baths, giving you room to grow, host, and settle in. A fireplace warms the main living area, while exotic wood, carpet, and ceramic tile carry through the floor plan. Upstairs, the spacious primary suite offers a peaceful retreat complete with a private en suite featuring heated tile floors for a touch of everyday luxury. Step outside to a deck featuring composite decking materials designed for longevity overlooking the backyard, made for morning coffee or evening gatherings, with a long driveway providing ample parking. Waterstone is known for its tree-lined streets and community pond, where residents can paddle a kayak, canoe, or paddleboard right in their own neighborhood. Book your showing now!

2072 River Pearl Way, West Chesapeake

509 Southfield Drive, South Chesapeake
$560,000
4 Beds ⋅ 2.1 Baths ⋅ 10648306 MLS
Fall in love with this beautiful home where timeless updates & thoughtful design come together. The stunning gourmet kitchen is the centerpiece of the home, featuring granite countertops, tile backsplash, stainless steel appliances, abundant cabinetry, wine fridge, and custom built-in bench that creates the perfect space for casual dining or gathering with company. Designed with everyday living in mind, the home offers an easy, inviting flow filled with abundant natural light, real hardwood floors & beautifully updated bathrooms throughout.Step outside to a spacious deck overlooking the landscaped backyard, providing the perfect setting for morning coffee, weekend cookouts, or simply relaxing outdoors.Located in one of Great Bridge's sought-after established neighborhoods. Convenient access to shopping, dining, parks, and everyday amenities. Enjoy the benefit of Chesapeake's highly regarded schools while experiencing the charm and convenience that make Great Bridge so special.

509 Southfield Drive, South Chesapeake

2256 Shipyard Road, South Chesapeake
$560,000
5 Beds ⋅ 3 Baths ⋅ 10635083 MLS
Ready Now. Stunning New Construction Home! Welcome to this beautiful 5-bedroom, 3 full bath home offering 2,073 square feet of modern living space. Designed with a spacious open floor plan, it's perfect for entertaining and everyday family living. Inside, the kitchen shines with soft-close cabinets, granite countertops, and a large center island ideal for gatherings. Bathrooms are also appointed with granite countertops and soft-close cabinetry for a cohesive, upscale look. Throughout the home, you'll find a blend of durable LVP flooring, plush carpet, and stylish tile. This home features a 2-car garage, and large multi-car driveway. This brand-new home is the perfect blend of comfort, style, and convenience-don't miss your chance to own it in the heart of Chesapeake!

2256 Shipyard Road, South Chesapeake

535 Currituck Drive, South Chesapeake
$560,000
4 Beds ⋅ 2.1 Baths ⋅ 10632373 MLS
This spacious 4-bedroom, 2.5-bath single-family residence offers 2,600 square feet of comfortable living space on a generous lot, perfect for families seeking room to grow. Thoughtfully designed with an inviting layout, it provides ample space for everyday living and entertaining. Pride of ownership shines throughout, highlighted by a brand-new carpet May 2026 and HVAC system installed in April 2026—ensuring year-round comfort, energy efficiency, and peace of mind for years to come. The property has a large back porch and yard for entertaining and activities. Located in a desirable, established Chesapeake neighborhood, you'll enjoy convenient access to excellent schools, parks, shopping, and dining, all while experiencing the perfect blend of suburban tranquility and modern updates. Whether you're hosting family gatherings or unwinding in your private retreat, this home is move-in ready and full of potential. Don't miss the opportunity to schedule a showing today!

535 Currituck Drive, South Chesapeake

718 Creekwood Drive, South Chesapeake
$560,000
4 Beds ⋅ 3 Baths ⋅ 10632273 MLS
Beautifully maintained home in the desirable Grassfield area of Chesapeake, tucked away on a quiet street with added privacy, as no home can be built next to it! This move-in ready property features a rare first-floor bedroom and full bath, ideal for guests or multi-generational living. Enjoy newer flooring throughout, updated kitchen countertops, and a well-appointed kitchen with appliances including a stove & dishwasher (2020), plus a new kitchen refrigerator (2025) and microwave (2026). The spacious primary suite offers a cozy fireplace and a beautiful bathroom. Additional highlights include a whole-house water softener, HVAC under annual maintenance, and thoughtful exterior upgrades like a covered back deck, French drain, and a new fence (2023). This home blends comfort, function, and peace of mind and is ready for its next owner!

718 Creekwood Drive, South Chesapeake

3029 Crossings Drive, West Chesapeake
$560,000
5 Beds ⋅ 3.1 Baths ⋅ 10630413 MLS
Well-maintained home on a corner lot in the heart of Western Branch. This centrally located property showcases a L-shaped Grecian-style pool and offers 5 spacious bedrooms and 3.5 bathrooms, including 2 ensuites. The layout is ideal for multi-generational living, with a primary ensuite on each floor. The 1st floor suite serves perfectly as an in-law suite, featuring a separate entrance and dry bar, while both suites include jetted tubs and expansive walk-in closets. The 2nd-floor primary suite adds a touch of warmth with a gas fireplace and a generous bathroom w/dual sinks. The open and airy main level is designed for both everyday living and gatherings, offering 2 large living areas, a dining room, a well-equipped eat-in kitchen, vaulted ceilings with skylights, and a cozy gas fireplace. Step outside to your private pool oasis that elevates the outdoor experience, creating a serene backyard retreat ideal for both relaxation and entertaining. Don't forget about the neighborhood park!

3029 Crossings Drive, West Chesapeake

1344 Fairhaven Road, South Chesapeake
$560,000
4 Beds ⋅ 2.1 Baths ⋅ 10631075 MLS
Fantastic energy efficient home in the sought after Stonegate subdivision on a corner lot with a grand L shaped in-ground pool with shallow end for the children and 8 ft deep end w/ a diving board for everyone to enjoy! The home has 4 Bedrooms and 2 1/2 baths and has been meticulously maintained and upgraded. Newer windows throughout 2021 & 2025, paid off Ion solar panels & Maytag reverse osmosis water filtration system, HVAC replaced 2023, updated bathrooms, new flooring upstairs, Pool Equipment Upgrades 2021 include Salt Cell, filter, pump, sensors, electric panel, transformer, and cover. Please ask your agent for the list of upgrades. Enjoy the backyard with new deck boards and shed. The garage has been converted into finished climate controlled space currently used as a gym and office/storage, there is still room for a work shop & parking for bikes, motorcycles etc. Don't miss out on your opportunity to own a little slice of paradise in Chesapeake w/ great schools!

1344 Fairhaven Road, South Chesapeake

700 Remington Drive, South Chesapeake
$560,000
4 Beds ⋅ 2.1 Baths ⋅ 10629893 MLS
Fully renovated and move-in ready, this stunning home blends modern updates with everyday comfort in a highly sought-after neighborhood. Redesigned kitchen is a true chef’s delight, featuring abundant storage, stylish finishes, open-concept layout that flows seamlessly into the main living space. Elegant LVP flooring throughout, a cozy fireplace, and a bright, inviting interior filled with natural light. All bathrooms have been thoughtfully updated, with the primary bath showcasing a luxurious standalone soaking tub for a spa-like retreat. Major systems have been upgraded for peace of mind: roof, HVAC, and water heater are all less than 3 years old, and windows are approximately 7 years old. Outside, the extended driveway provides ample space, ideal for RV or additional parking. A detached shed conveys as-is for added storage. Ideally located near highways, top-rated schools, parks, shopping, and dining, this home offers both convenience and lifestyle. Hurry will go fast.

700 Remington Drive, South Chesapeake

3212 Sybilla Street, South Chesapeake
$560,000
4 Beds ⋅ 2.1 Baths ⋅ 10629024 MLS
It may say 2013, but this home has been thoughtfully reimagined and extensively updated, offering the look and feel of 2023. Designed for everyday living, it features a sought-after first-floor primary suite, 9-ft ceilings, and LVP flooring throughout the first floor. The kitchen shines with quartz countertops, high-end stainless appliances, and a custom-designed pantry. A second-story loft-style family room adds flexible living space, while the primary suite includes a custom-designed closet and a spa-like bath with double showerheads. Major systems and mechanicals were updated in 2023 to include a new panel box with generator hookup and EV capabilities, providing peace of mind. Enjoy a fenced backyard, large patio, 2-car attached garage, and driveway for up to six vehicles, and just two blocks to the largest aquatic center in Hampton Roads! Life in Culpepper Landing is unmatched, with all the amenities, stocked lakes, a dog park, trails, and community events. Call for a private tour!

3212 Sybilla Street, 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.