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708 Wimbley Lane, South Chesapeake
$539,000
4 Beds ⋅ 2 Baths ⋅ 10654471 MLS
Beautiful Cape Cod ranch on a cul-de-sac lot featuring 4 bedrooms, 2 full baths, and a 2-car side-load garage. The spacious primary suite offers a walk-in closet and bright private bath with dual sinks and skylights, The great room features a gas fireplace, built-in bookshelves, and newer carpet, Convenient main-level bedroom, The kitchen boasts newer LVP flooring and stainless-steel appliances, with French doors leading to a screened-in back porch with ceiling fan. Freshly pressure washed and landscaped, the home offers easy-care yards with irrigation front and back. A backyard shed provides additional storage.

708 Wimbley Lane, South Chesapeake
620 Emerald Court, South Chesapeake
$399,900
4 Beds ⋅ 2.1 Baths ⋅ 10654385 MLS
Welcome to your next great opportunity! This spacious 1,917 sq ft ranch home offers 4 bedrooms and 2.5 bathrooms with a flexible floor plan designed for effortless daily living. The functional layout includes a large Finished Room Over Garage (FROG) as the 4th bedroom— could also be used as an office, media room, or flex space. Inside flows seamlessly to the back deck, overlooking an expansive 0.389-acre lot with abundant outdoor space and a large storage shed. Complete with a 1-car attached garage, this property offers incredible potential! Bring your vision—with a touch of sweat equity and minor cosmetics, this solid home will truly shine and build instant equity. Excellent location with convenient access to major interstates, regional bases, dining, shopping, and entertainment. Call today to schedule your private showing!

620 Emerald Court, South Chesapeake
1025 Shore Road, South Chesapeake
$325,000
3 Beds ⋅ 1.1 Baths ⋅ 10654363 MLS
Come tour this ranch home with beautiful hardwood floors and a functional living space. This property has a partially open floor plan with a versatile layout. The open room space can be used to entertain, as an office, or as spare living space. The backyard is large and wooded, offering a storage shed and plenty of space for gardening and entertaining. The dishwasher, water heater, and refrigerator are all new (2025) and convey with the property.

1025 Shore Road, South Chesapeake
313 Gale Avenue, South Chesapeake
$369,900
3 Beds ⋅ 2.1 Baths ⋅ 10654338 MLS
Welcome home to this charming 3-bedroom, 2.5-bath, two-story home in Chesapeake! Fresh paint throughout and new carpet upstairs give the home a clean, refreshed feel, while brand-new appliances make the kitchen move-in ready. The spacious, open floor plan, two-story layout offers comfortable living with plenty of room to spread out. Come see all that 313 Gale Ave has to offer and make it your new home!

313 Gale Avenue, South Chesapeake
744 Helmsdale Way, South Chesapeake
$425,000
4 Beds ⋅ 2.1 Baths ⋅ 10654335 MLS
Discover timeless charm in this beautiful, traditional home located in the heart of Chesapeake. Featuring 4 bedrooms, 2.5 bathrooms, and a spacious two-story layout, this home includes a bedroom with its own en suite bath, making it great for guests or added privacy. Gather around the cozy fireplace on cool evenings, or enjoy casual meals in the bright breakfast area. Step outside to a fully fenced backyard, great for entertaining, pets, or relaxing outdoors. Recent upgrades, including new siding and roof (2021) and a remodeled primary bathroom (2025), enhance both the home's beauty and value. An attached garage and attic complete this exceptional property. Don't miss your opportunity to make this Chesapeake gem your own!

744 Helmsdale Way, South Chesapeake
1209 Sir Galahad Drive, South Chesapeake
$359,000
3 Beds ⋅ 2 Baths ⋅ 10654313 MLS
Welcome to 1209 Sir Galahad! This beautifully updated one-owner home offers a comfortable, inviting flow with plenty of natural light throughout. Recent improvements include new LVP flooring, fresh paint, updated light fixtures, and a completely renovated primary bathroom. The kitchen features all-new GE appliances, quartz countertops, and new soft-close cabinetry. Tucked away on a quiet street in a mature, established neighborhood with convenient access to the interstate, this home offers the perfect combination of thoughtful updates, comfort, and accessibility.

1209 Sir Galahad Drive, South Chesapeake
515 Sweet Leaf Place, South Chesapeake
$425,000
3 Beds ⋅ 2.1 Baths ⋅ 10654218 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
5144 Ballahack Road, South Chesapeake
$400,000
4 Beds ⋅ 2 Baths ⋅ 10654279 MLS
Welcome home to peaceful country living on approximately 0.71 acres! This inviting ranch-style home offers 4 bedrooms and 2 full bathrooms, with fresh paint throughout, new LVP flooring, and new carpet making it move-in ready. The spacious living room features vaulted ceilings, while the kitchen opens to a cozy breakfast nook perfect for morning coffee or casual meals. Out back, enjoy a private yard surrounded by wooded views, an ideal setting for relaxing, entertaining, or simply enjoying a little extra peace and quiet. Tucked away in a country setting yet conveniently located just off Highway 17, this home gives you the best of both worlds: room to breathe with easy access to everything you need.

5144 Ballahack Road, South Chesapeake
1085 Bells Mill Road, South Chesapeake
$415,900
4 Beds ⋅ 2 Baths ⋅ 10653838 MLS
Welcome home to 1085 Bell Mill Rd.! This beautifully refreshed 4-bedroom, 2-bath Chesapeake home is move-in ready and filled with features you'll love. Fresh paint throughout creates a bright, inviting feel, while the updated kitchen and bathrooms add a modern touch. The cozy gas fireplace creates the perfect gathering spot in the living area. Step outside to enjoy the backyard, complete with established blueberry bushes and apple trees - a wonderful bonus for enjoying fresh fruit right at home. With comfortable living spaces, thoughtful updates, and a convenient Chesapeake location, this home offers the perfect blend of charm, functionality, and everyday living. Come see all this home has to offer!

1085 Bells Mill Road, South Chesapeake
1816 Sunsprite Loop, South Chesapeake
$599,900
6 Beds ⋅ 3 Baths ⋅ 10654192 MLS
It’s got space!! Use all 6 bedrooms or create the office, guest room, fitness space or playroom you've been looking for. The first floor offers a bedroom, adjacent flex room and modified curb less shower—great for guests or anyone who prefers fewer stairs. Neutral décor, 9' ceilings, hardwood floors, crown molding and a huge FROG. Spacious primary suite with hardwood floors and two walk-in closets, plus second-floor laundry. Outside, enjoy a lg, fenced backyard , detached shed, private well for lawn irrigation and attached 2-car garage. Meticulously maintained with annual HVAC, tankless water heater and crawl-space service contracts. Seller to provide termite/moisture letter. Convenient to Millville Rd. and Veterans Bridge. Annual Termite/Moisture contracts/ NO FLOOD INS. Grassfield High School has earned national recognition in US News and World Reports for VA’s Board of Education Highest Achievement Award / 2024.

1816 Sunsprite Loop, South Chesapeake
1205 Aaron Court, South Chesapeake
$348,500
4 Beds ⋅ 2 Baths ⋅ 10653794 MLS
This renovated ranch is nestled in the neighborhood and boasts new paint and LVP and lighting throughout. Brand new kitchen (with new SS appliances) with eye-catching quartz countertops, overlooks the dining room . Updated bathrooms with new ceramic tile and vanities. All this plus a new roof! Walk in and enjoy the open floor plan of your new home! Both sheds sold "as is".

1205 Aaron Court, South Chesapeake
102 Diamond Avenue Unit D, South Chesapeake
$246,500
2 Beds ⋅ 1.1 Baths ⋅ 10654041 MLS
A Diamond Condo with NO FEES! Located in the highly sought-after Grassfield school district, this condo has had a complete transformation. Walk into a beautiful cathedral ceiling and unique reading nook under the stairs. New SS Appliances in the kitchen, new luxury vinyl floors, bedroom/office downstairs with laundry,Beautifully renovated full bathroom. Private upstairs bedroom with half bath spacious closet space and attic storage access. Partially fenced backyard. This is in a quiet neighborhood conveniently located near interstates and shopping. Hurry, before this one is gone!

102 Diamond Avenue Unit D, South Chesapeake
601 Lord Byron Court, South Chesapeake
$380,000
3 Beds ⋅ 2.1 Baths ⋅ 10653788 MLS
Welcome home to this stunning 3-bedroom, 2.5-bathroom gem nestled in one of Chesapeake's most serene and desirable neighborhoods. The main level boasts a bright and cozy living room that flows seamlessly into a stylish kitchen, making everyday living and entertaining a breeze. Upstairs, you will find spacious, private bedrooms and well-appointed bathrooms. Outside is a generous backyard that serves as your own private oasis, perfect for hosting weekend gatherings, gardening, or relaxing in the sun. Situated in a peaceful community just minutes from local shopping, dining, schools, and major commuter routes, this home truly has it all. Don't miss the opportunity to make this house your home sweet home! Schedule your private tour today! Listing photos contain virtually staged media.

601 Lord Byron Court, South Chesapeake
704 Woodcott Drive, South Chesapeake
$560,000
3 Beds ⋅ 2.1 Baths ⋅ 10654136 MLS
Welcome home to 704 Woodcott Drive. This beautifully refreshed 4 bedroom 2 1/2 bath home is full natural light and lovingly updates. The bright, inviting interior features new LVP flooring, new carpet, and fresh paint throughout, giving the home a beautiful, fresh feel. The updated kitchen is great for gatherings, with quartz countertops, stainless steel appliances, and a gorgeous double sided fireplace shared with the living room. The loft can be used as a flex room, office or media room. Enjoy the barbecues on the back deck overlooking the huge backyard. Make this the perfect spot to enjoy cozy evenings or entertaining family and friends. Seller to offer buyer 2/1 rate buy down as well as a new driveway with full price offer.

704 Woodcott Drive, South Chesapeake
2426 Livesay Road, South Chesapeake
$290,000
4 Beds ⋅ 2 Baths ⋅ 10654129 MLS
Come see this updated 4 Bed, 2 Bath home in Chesapeake! Recent improvements include fresh paint throughout, new carpet, new LVP flooring, and a refreshed kitchen featuring new cabinets and appliances. Additional updates include a new HVAC system and new ductwork. Outside, enjoy a fully fenced backyard offering plenty of space for outdoor activities and entertaining. Some photos have been AI Generated to help show case the homes true potential.

2426 Livesay Road, South Chesapeake
28 Hinton Avenue, South Chesapeake
$330,000
4 Beds ⋅ 2 Baths ⋅ 10654130 MLS
Experience total move-in readiness in this beautifully updated Chesapeake home! Featuring fresh paint and new flooring throughout, the bright interior flows into a modern kitchen equipped with shaker cabinets and stainless steel appliances. Bathrooms boast stylish tile updates, while peace of mind comes standard with a new roof, HVAC, some new windows and new water heater. There is also a bonus florida room and lovely front porch. Perfectly blending comfort and modern upgrades, this property is an absolute must-see today!

28 Hinton Avenue, South Chesapeake
415 Prince Phillip Court, South Chesapeake
$409,000
3 Beds ⋅ 2.1 Baths ⋅ 10654072 MLS
Welcome to this spacious 3-bedroom, 2.5-bath split-level condo in a great Chesapeake location near Oak Grove Park, the hospital, shopping, and interstate access. The mid-level foyer leads to the lower level, featuring a comfortable sitting room with a fireplace, access to the back deck and fenced backyard, a utility closet, two bedrooms with large closets, full hall bathroom, and access to the attached 2-car garage with a convenient garage door opener. Upstairs, the updated kitchen offers stainless steel appliances, a pantry, bar, and breakfast area with bench seating, along with a fireplace and built-in storage. The upper-level living room provides additional space for relaxing or entertaining. The spacious primary suite features a walk-in closet and ensuite bathroom with a granite vanity, built-in makeup table, jetted tub, separate shower, and water closet.

415 Prince Phillip Court, South Chesapeake
523 Las Gaviotas Boulevard, South Chesapeake
$580,000
4 Beds ⋅ 2.1 Baths ⋅ 10654039 MLS
Welcome home to this spacious 4-bedroom, 2.5-bath two-story home offering approximately 2,800 square feet in the Grassfield High School district. With both a formal living room and dining room, a large family room, and an eat-in kitchen, there’s plenty of space to gather, entertain, and make yourself at home. An additional bonus room offers great flexibility for a home office, study, craft room, or whatever fits your lifestyle. Enjoy beautiful views of the 14th hole of the Las Gaviotas Golf Course right from home. Vacant and ready for its next owners—come see how easily you can picture yourself calling this pretty house home!

523 Las Gaviotas Boulevard, South Chesapeake
1547 Orchard Grove Drive, South Chesapeake
$290,000
2 Beds ⋅ 2 Baths ⋅ 10654011 MLS
Welcome home to easy living in Orchard Grove! This spacious 2-bedroom, 2-bath condo offers a flexible layout designed for both everyday comfort and entertaining. Start your morning at the dedicated coffee bar before settling into the light-filled living room, where soaring ceilings and skylights create an open, airy feel. When the weather cools down, the gas fireplace makes the perfect spot to unwind. The updated kitchen features new cabinets, quartz countertops, stainless steel appliances, and plenty of space for preparing meals and gathering. Upstairs, the loft adds even more flexibility—create a home office, workout space, reading nook, hobby room, or explore modifications for an additional sleeping area. With two bedrooms and two full baths, there’s room to spread out while still enjoying the convenience of condo living. Orchard Grove puts shopping, dining, interstate access, military installations, and everyday conveniences nearby, making it easy to spend less time getting where you need to go and more time enjoying home.

1547 Orchard Grove Drive, South Chesapeake
100 Alice Street, South Chesapeake
$367,000
4 Beds ⋅ 2.1 Baths ⋅ 10653943 MLS
Welcome Home to Deep Creek! This beautifully renovated brick ranch offers 4 bedrooms, 2.5 baths, and an impressive list of brand-new updates. Step inside to discover brand-new gray carpet and luxury vinyl flooring throughout, complemented by fresh finishes that give the home a clean, modern feel. The updated kitchen features brand-new white cabinetry, a center island, granite countertops, and stainless steel appliances, creating a functional space for everyday living and entertaining. Both full bathrooms have been refreshed with brand-new ceramic marble tile in the showers for a polished, spa-inspired touch. And the updates continue beyond the interior! This home features a brand-new roof, HVAC system, and water heater, offering peace of mind for years to come. With two front and two back entry points, the layout also provides added flexibility for how you enter and use the home. Located in the desirable Deep Creek subdivision and just moments from the Gilmerton Bridge, this home offers convenient access to surrounding areas while providing the space and comfort of a brick ranch-style home. Four bedrooms. Two and a half baths. Brand-new major systems and finishes. Move-in ready. Come see all this home has to offer!

100 Alice Street, South Chesapeake
1101 Gauntlet Drive, South Chesapeake
$380,000
4 Beds ⋅ 2.1 Baths ⋅ 10653901 MLS
Welcome to 1101 Gauntlet Drive in Chesapeake! This spacious 4-bedroom 2.5-bath home offers approximately 1,824 square feet of comfortable living space. Step inside to a freshly painted interior featuring luxury vinyl plank flooring and an inviting living room with a cozy fireplace. The kitchen features white cabinetry, stainless steel appliances, a farmhouse-style sink, and plenty of workspace. Enjoy additional living and entertaining space in the Florida room overlooking the backyard. Upstairs, you’ll find generously sized bedrooms with great natural light. Stop here first! This is a wonderful opportunity to make this Chesapeake home your own!

1101 Gauntlet Drive, South Chesapeake
832 Woodrow Court, South Chesapeake
$475,000
4 Beds ⋅ 2 Baths ⋅ 10653661 MLS
Tucked away at the end of a quiet cul-de-sac, this exceptionally clean and carefully maintained 4-bedroom home offers comfortable living and added peace of mind with a newly installed roof with warranty. The spacious bedroom over the garage provides flexibility, while the sunroom adds another 180 square feet of living space overlooking a private, fully fenced backyard. Start your morning in the kitchen’s inviting breakfast area, unwind beside the wood-burning fireplace, or enjoy outdoor gatherings in the backyard. A separate utility room, efficient geothermal heating and cooling, and low-maintenance exterior trim add everyday convenience. The seller will provide a clear termite and moisture letter. Located within the Great Bridge school attendance area, this move-in-ready home is priced to sell and ready for its next chapter. Put this one on your showing list!

832 Woodrow Court, South Chesapeake
753 Willow Bend Drive, South Chesapeake
$399,900
4 Beds ⋅ 2 Baths ⋅ 10653770 MLS
Welcome home to this spacious 4-bedroom, 2-bath home offering a wonderful combination of comfort and open space. The inviting living room features vaulted ceilings, two skylights, and abundant natural light, creating a bright and open feel. The primary bedroom and bath are conveniently located on the main floor, along with main-level laundry for easy everyday living. One of the standout features is the very large second living room, featuring cathedral ceilings and lots of windows that fill the space with natural light while overlooking the backyard and pond. A 2-car attached garage provides plenty of room for parking and storage.

753 Willow Bend Drive, South Chesapeake
224 Northview Drive, South Chesapeake
$485,000
3 Beds ⋅ 2.1 Baths ⋅ 10653649 MLS
Renovated brick ranch in the Great Bridge school district, in established Chesapeake Colony. Less than half a mile to Great Bridge Middle, about a mile to Great Bridge Primary and under 2 miles to Great Bridge High. This single-level 3-bedroom, 2.5-bath home offers 1,854 sq ft with hardwood floors, two wood-burning fireplaces and a renovated kitchen with Corian countertops, stainless steel appliances and LVP flooring. Both full bathrooms have been fully renovated with natural stone flooring, custom tile and updated vanities. System updates include roof (2010) HVAC (2010) and tankless water heater (2025). Natural gas, a generator hookup and an oversized attached garage add everyday convenience. The 0.34-acre lot is set among mature trees, Japanese maples and azaleas. Out back: a privacy-fenced yard with a two-level composite deck and low-voltage lighting, a Wellis hot tub, a gazebo with swing, a pea gravel patio, a separate gated dog run and a powered 10x14 shed with loft and workbench. Irrigation and a double-wide driveway with parking for five complete the package. Minutes to Great Bridge shopping, dining and Chesapeake Regional Medical Center.

224 Northview Drive, South Chesapeake
1115 Killington Arch, South Chesapeake
$335,000
3 Beds ⋅ 2.1 Baths ⋅ 10653708 MLS
End-unit townhouse in Greenbrier with a peaceful pond view right in your backyard-no neighbors behind you! This home has 3 bedrooms, 2.5 baths, plus a versatile loft that works as an office, 4th bedroom, or hangout space. The kitchen features butcher block countertops & stainless steel appliances. The primary bedroom is generously sized with plenty of room to spread out. Being an end unit means extra privacy, more natural light, and fewer shared walls than a typical interior unit. Outside, it's quiet and low-key with lakes and a playground to enjoy. Located in the heart of Greenbrier East with quick access to major highways, you are just minutes away from everything Hampton Roads has to offer, including military bases, shopping, dining, beaches, and parks.

1115 Killington Arch, South Chesapeake
1901 Kelly Run, South Chesapeake
$435,000
4 Beds ⋅ 2.1 Baths ⋅ 10652939 MLS
4 bedrooms 2.5 baths on cul-de-sac. Large fenced yard on lake with shed. All kitchen appliances. New electric panel and HVAC in 2023. New fence across the back of yard in 2024. Reverse osmosis and re-mineralizer installed on kitchen sink. New refrigerator, kitchen faucet and microwave in September 2026. Fireplace and dryer vent cleaned and inspected August 2026.

1901 Kelly Run, South Chesapeake
1232 New Born Court, South Chesapeake
$445,000
5 Beds ⋅ 2.1 Baths ⋅ 10653581 MLS
Welcome home! This beautiful home in Chesapeake is ready for its new owners! With 5 bedrooms, 2.5 bathrooms, and a layout designed to offer the perfect balance of togetherness and privacy, there is room for everyone. The kitchen offers plenty of cabinets and counter space and flows right into the open dining/living area. Two separate living spaces provide flexibility for entertaining, relaxing, or everyday living. Outside, enjoy a spacious backyard with a great deck, storage shed, and even a chicken coop! Located in a highly sought-after school district and a close proximity to shopping, dining and interstate access, this house checks all the boxes! Shed and chicken coop convey as-is. Don't let this one get away - call today to schedule your tour!

1232 New Born Court, South Chesapeake
1216 Club Point Drive, South Chesapeake
$380,000
3 Beds ⋅ 2.1 Baths ⋅ 10653557 MLS
Beautiful Single Family Condo in the heart of Great Bridge/Grassfield! New Roof, A/C Unit & Deck (Over 30k in upgrades). 1st floor Primary Bedroom, soaring ceiling in great room, Eat-In-Kitchen, dining room, 2 bedrooms and full Bath on the 2nd floor. Better Hurry!

1216 Club Point Drive, South Chesapeake
905 Bernard Lane, South Chesapeake
$525,900
4 Beds ⋅ 3.1 Baths ⋅ 10653474 MLS
$12,500 closing costs*, Low Loan Rate, No PMI! - Choose your look! - UPGRADES GALORE! Built by award-winning builder. Stunning home w/curated features uniquely designed in this home. Extensive Mohawk flooring through mid-level with Gourmet Kitchen w/Custom hood, 10' island with Quartz counters, GE Cafe 6 Burner Gas range, GE Cafe Dishwasher, and GE Cafe Microwave Drawer. 10' ceilings MAIN, 9' First & Third Floors, 2-zone HVAC w/thermostat on each floor. Primary bedroom with Walk-in CLOSET and spa ensuite Bath. Custom stair rail with 42" treads. Two bedrooms, hall bath, and laundry room complete the third flr. First floor bedroom with ENSUITE bath! Oversized 10'x19' covered porch with Trex decking, 2-car garage, Tankless Water Heater - and more! LOW $95 condo fee w/Cabana, Fire pits, Bocce ball and Professional landscape and lawn maintenance.. Ready for easy living! Legacy is waiting for you!

905 Bernard Lane, South Chesapeake
1201 Richwood Avenue, South Chesapeake
$575,000
5 Beds ⋅ 3 Baths ⋅ 10653391 MLS
Gorgeous, like-new home built in 2016 offering over 2,400 sq ft of living space. A first-floor bedroom and full bath make this layout great for guests, a home office, or an in-law suite.The gourmet kitchen is made for entertaining, featuring granite countertops, stainless steel appliances, and a gas range. Step outside to a fenced backyard backing to peaceful wooded views; great for morning coffee or quiet evenings.With modern finishes throughout and minimal need for updates, this home is truly move-in ready and packed with value!

1201 Richwood Avenue, 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.