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2323 Herring Ditch Road, South Chesapeake
$500,000
3 Beds ⋅ 2.1 Baths ⋅ 10645963 MLS
Wonderful opportunity to get 4+ acres in high rated schools. HUGE outbuilding with 3 bays garage bays, powered, multi-level, for storage and recreational activities. Home sold as is. Part of an estate. Seller to do no repairs.

2323 Herring Ditch Road, South Chesapeake
452 Warhawks Road, South Chesapeake
$500,000
3 Beds ⋅ 2 Baths ⋅ 10641496 MLS
Nestled in the heart of Great Bridge, this charming home has been lovingly maintained, thoughtfully updated, and freshly painted throughout including a newer roof, HVAC system, water heater, windows, and appliances, offering peace of mind for years to come. Inside, you'll find a spacious and private primary suite complete with its own en-suite bath and private deck. A bright, all-season sunroom overlooks the backyard and opens onto a newly installed patio, creating an ideal space for relaxing or entertaining. In addition to two secondary bedrooms, the home features a versatile private flex room that can easily serve as a home office, playroom, guest room, or fourth bedroom. With flexible living spaces and numerous updates, this adorable Great Bridge home offers comfort, functionality, and charm in a highly desirable location. Quick access to shopping, restaurants & interstates – also located in the Great Bridge HS, Great Bridge Middle and Butts Road Primary School districts!

452 Warhawks Road, South Chesapeake
337 Woodbridge Drive, South Chesapeake
$500,000
4 Beds ⋅ 2 Baths ⋅ 10638412 MLS
Welcome Home to this charming brick ranch in the desirable Wilson Heights subdivision of Chesapeake's Great Bridge! Inviting foyer leads you to an ideal layout with oversized Den that can be used as separate one singular space, formal dining room, kitchen with breakfast nook and access to hall leading to back deck, laundry, mud room, 4th bedroom/FROG, and Garage. Off the foyer also leads down hall to large secondary bedrooms, spacious hall bath, multiple storage closets, and primary suite. Primary suite features sizable closet, and ensuite bathroom with tile shower and updated flooring. Back deck recently painted and yard is serene and ready for your stamp. Call this Home Today!

337 Woodbridge Drive, South Chesapeake
2813 Ridgeboard Place, South Chesapeake
$500,000
4 Beds ⋅ 2.1 Baths ⋅ 10637881 MLS
Welcome home to 2813 Ridgeboard Place located in the sought after neighborhood, Sawyers Mill in Chesapeake! This home has been freshly painted and new LVP and carpet installed throughout just for you! More updates include: HVAC (2023) Duct work (2025) Water heater (2016) French drains (2025) Windows, trim and siding (2025) Roof (2012) Fresh paint throughout the whole interior (2026) LVP (2026) Carpet (2026) Exterior doors (2025) Downstairs you will find a spacious living room with cathedral ceilings open up to a formal dining room. The kitchen is features plenty of cabinet space, a walk-in pantry, a breakfast nook and all appliances convey. Off the kitchen is another living room with lots of natural light and a gas fireplace which will lead you to the laundry room, half bathroom and garage access. Upstairs features a primary suite with a dual sink vanity, walk-in closet, jetted tub, stand up shower and spacious bedroom. Additionally there are three other bedrooms, a hall bathroom and linen closet. Make this house your next home today!

2813 Ridgeboard Place, South Chesapeake
1004 Wymers Court, South Chesapeake
$500,000
5 Beds ⋅ 2 Baths ⋅ 10633344 MLS
Spacious 5-bedroom ranch with finished room over the garage offers a unique natural setting on a quiet cul-de-sac just minutes from the 168 Bypass. The 5th bedroom on the first floor offers flex potential as an office or recreational space. Enjoy beautiful views of nature from kitchen and primary bedroom bay windows. Updates include: new LVP throughout the home, newer HVAC, newer gas water heater, walk-in shower with pull down bench and grab bar. Roof replaced in 2018. Removable wheelchair ramp conveys if needed.

1004 Wymers Court, South Chesapeake
1009 Mathews Drive, South Chesapeake
$500,000
4 Beds ⋅ 2.1 Baths ⋅ 10627762 MLS

1009 Mathews Drive, South Chesapeake
809 Kemp Meadow Drive, South Chesapeake
$500,000
4 Beds ⋅ 2.1 Baths ⋅ 10627580 MLS
Welcome to your next happy place in popular Kemp Crossing! 4 beds, 2.5 baths, and seriously well-loved. Pull into the driveway and catch the Chesapeake City Park fireworks right from home! This house has been upgraded and maintained like a pro: no original windows remain, new shed roof, and a front yard sprinkler system serviced yearly. Big recent wins: 2024 kitchen makeover including new appliances, new LVP and a refreshed driveway; 2023 new carpet, tankless water heater, and whole-house generator; 2022 new HVAC/ductwork and a refreshed primary bath. Water heater service paid through 2027 with Smith & Keene. Move-in ready, low-stress, high-fun...come see!

809 Kemp Meadow Drive, South Chesapeake
420 Woodberry Drive, South Chesapeake
$500,000
4 Beds ⋅ 2.1 Baths ⋅ 10627528 MLS
Lovely home in sought after Wilson Heights in the heart of Great Bridge. Inviting front porch, large 2 car garage. Great floorplan with 2 living areas, dining room, hall half bath for guests, kitchen and a small flex room that could be anything you desire. 3 nice sized bedrooms and hall full bath upstairs. Large primary suite with double closets and bath. Huge corner lot with mature trees. Newer items: roof, windows, HVAC, smart garage door opener, appliances, water heater. All the big stuff is done! Move in and make it your own! This is a great home in a well known neighborhood in sought after all Great Bridge schools. No HOA. Don't miss this one!

420 Woodberry Drive, South Chesapeake
1501 Rosehill Drive Unit 46, South Chesapeake
$500,000
3 Beds ⋅ 3 Baths ⋅ 10625581 MLS
Welcome home to The Retreat at Greenbrier, a sought-after 55+ community in the heart of Chesapeake with convenient access to shopping, restaurants, and medical offices. This popular model offers 3 bedrooms and 3 full baths with flexible office or den space. Enjoy the warmth of gas fireplace shared by the living room, dining room, and kitchen areas. Spacious kitchen with plenty of cabinet storage and breakfast bar seating. First-floor primary bedroom with private bath and dressing area. Large second-floor bedroom/bonus room with Bath, great for guests or hobbies. Two-car attached garage. Don’t miss this one!

1501 Rosehill Drive Unit 46, South Chesapeake
713 Waterford Court, South Chesapeake
$500,000
4 Beds ⋅ 2 Baths ⋅ 10617099 MLS
Beautifully updated 4-bedroom, 2-bath home situated on nearly half an acre at the end of a quiet cul-de-sac. This fully fenced property offers privacy and space, with numerous upgrades throughout—including a remodeled kitchen and bathrooms, updated flooring, fresh paint, modern fixtures, an expansive deck, and crawlspace improvements. Too many updates to list—see the full upgrade list in the listing documents. This home truly must be seen to be appreciated. Located in the highly sought-after Great Bridge school district with convenient access to interstates, shopping, and military bases.

713 Waterford Court, South Chesapeake
533 Scarborough Drive, South Chesapeake
$500,000
4 Beds ⋅ 2 Baths ⋅ 10615967 MLS
Well-maintained and recently updated home. Kitchen features quartz countertops, soft-close cabinets and drawers, and stainless steel appliances including an electric range, over-the-range microwave, and newer LG dishwasher. Upgraded LVP flooring runs throughout the main living areas, with carpeted bedrooms for added comfort. Spacious living room opens to the dining area and showcases a brick wood-burning fireplace with a custom rustic wood mantel. Fresh interior paint, new ceiling fans in all bedrooms, updated light fixtures, and a low-maintenance exterior. HVAC system and roof are approximately five years old, with new HVAC ductwork and vapor barrier. Sunroom overlooks the fenced backyard and offers flexible space not included in the home's square footage. Property also includes a large detached garage ideal for a workshop, ample concrete parking, and two storage sheds. Located in the Great Bridge schools district with convenient access to nearby amenities.

533 Scarborough Drive, South Chesapeake
324 Big Pond Lane, South Chesapeake
$500,000
4 Beds ⋅ 2.1 Baths ⋅ 10614917 MLS
Welcome to this beautifully updated home in sought after Sawyers Mill in the heart of Grassfield. The house has updated kitchen tops, appliances & flooring with Remodeled master bath & updated vanities. This home has an inviting Covered front porch & the rear deck w/Trellis that offers great outdoor entertaining space. Solar panels (paid off) offer low electric bills averaging $50/month. The community vibe is attributed to the community pool, clubhouse, playground & trails. The neighborhood borders the Deep Creek Park for more outdoor fun.

324 Big Pond Lane, South Chesapeake
735 Wood Duck Lane, South Chesapeake
$500,000
4 Beds ⋅ 3 Baths ⋅ 10611054 MLS
Come see this all brick 4 bedroom 3 full bathroom home, on .70 of an acre with 2 docks & powered shed. The house is freshly painted throughout including the garage. New flooring upstairs and in the FROG. New gas stove and dishwasher, primary double sink vanity. Enjoy the screened-in porch with PEACEFUL views of the waterway, the large deck for entertaining, and extra large backyard with dream shed/workshop. The driveway and garage are large.Home is in very good condition, but priced well below market, and as-is for a quick sale. 2025 fresh paint, flooring, gas stove, dishwasher, updates to docks, new vapor barrier in the crawl. 2023 Upstairs and FROG flooring. 2022 water heater, upstairs HVAC. 2017 new shed with sub panel and electricity. Windows are original - needs new ballasts but they do open and close. Boat lift not operated in years and may require maintenance. Other than that this home has been very well maintained and in move in condition.

735 Wood Duck Lane, South Chesapeake
629 Creekwood Dr, South Chesapeake
$500,000
4 Beds ⋅ 2.1 Baths ⋅ 10610472 MLS
Welcome Home to this stunning 4-bed, 2.5-bath, 2,150 sqft waterview beauty! Enjoy breathtaking views from an open-concept kitchen and dining area featuring granite countertops, stainless steel appliances, a large island, and wall-to-wall windows overlooking the water. The flowing layout offers generous living spaces for gatherings and everyday comfort. Retreat upstairs to a spacious primary suite, complemented by three additional bedrooms. Updated baths, modern finishes, and exceptional natural light add to the warmth and charm of this home. Outdoors, a large backyard with peaceful water views for relaxing, entertaining, or creating lasting memories. An attached 2-car garage and extended driveway provide ample parking. Convenient to shopping, military bases, and schools. This rare waterview opportunity won’t last—make it yours today! This text has been generated by artificial intelligence.

629 Creekwood Dr, South Chesapeake
1413 Thistlewood Lane Unit 54, South Chesapeake
$500,000
3 Beds ⋅ 3 Baths ⋅ 10608836 MLS
One look and you will feel right at home in this highly desired "Charleston" with upgrades galore. Open floor plan features vaulted ceiling in huge great room with cozy gas fireplace, light and bright dining room, fresh paint and hard surface floors on main level. Nice kitchen with raised bar boasts an abundance of cabinets with beautiful quartz countertops. There are 2 bedrooms on main level including spacious master suite with sitting room/office. Convenient chair lift offers easy access to the FROG/3rd bedroom with full bath. Large covered front porch is the perfect place to enjoy your morning coffee. 55+ Lifestyle Community with Exercise Room, Pool, Fabulous Clubhouse with card and billiard tables, outdoor gathering area with grill and much more! This beauty will not last...schedule your tour today and start packing!

1413 Thistlewood Lane Unit 54, South Chesapeake
572 Akron Avenue, South Chesapeake
$500,000
4 Beds ⋅ 2 Baths ⋅ 10604655 MLS
Step into this beautifully updated 2,049 sqft home with tons of space and charm. The welcoming entry opens to a sunlit dining area and front room—lovely for a home office, home gym, or formal sitting. The cozy family room features surround sound speakers and gas fireplace, leading to a stunning kitchen with SS appliances, gas cooking, and a serene breakfast area. The spacious primary suite boasts a large walk-in closet and a newly renovated bath with a custom tile shower and beautiful vanity. Three additional large bedrooms include a versatile FROG with access to an expansive walk-in attic. Outside, enjoy a large deck, beautifully landscaped yard, & saltwater pool with new liner and pump (2024), all enclosed by a 6ft vinyl privacy fence. Recent upgrades include HVAC, Roof, and Water Heater as well as brand new vapor barrier, carpet, tile, lighting & fresh paint throughout. Complete with a 2-car Garage and located in a lovely neighborhood zoned for sought after Grassfield Highschool!

572 Akron Avenue, South Chesapeake
329 Barcelona Drive, South Chesapeake
$500,000
3 Beds ⋅ 2 Baths ⋅ 10602102 MLS
Discover this immaculate 3-bedroom, 2-bath home in Chesapeake, VA, offering stunning canal-front living with your own private dock—great for canoeing or john boat adventures. Enjoy the spacious family room with vaulted ceilings, and a four-season room that connects directly to the primary suite and family room. With 5 entry points and a charming wraparound porch, this home blends indoor comfort with outdoor charm. The detached 2-car garage and long driveway provide ample parking, plus additional street parking for guests. Whether you're entertaining or relaxing, this beautifully maintained home offers the ideal waterfront lifestyle in Chesapeake. Located near top-rated schools, shopping, and dining, it’s a rare find that won’t last long. Schedule your showing today and experience Chesapeake canal-front living at its best!

329 Barcelona Drive, South Chesapeake
3424 Eight Star Way, South Chesapeake
$500,000
4 Beds ⋅ 2.1 Baths ⋅ 10599870 MLS
Beautifully updated 4 BR, 2.5 BA home in sought-after Olde Mill Run! Featuring a new roof and flooring (2025) along with modern lighting, this home is move-in ready. Step inside to a welcoming foyer that flows into a bright living area. The open floor plan includes a stylish kitchen with stainless-steel appliances and breakfast nook, overlooking the family room with a cozy gas fireplace. Upstairs, find 4 spacious bedrooms, including a large primary suite with walk-in closet, spa tub, and separate shower. The expansive backyard offers endless possibilities for entertaining, gardening, or play. Conveniently located near parks, trails, and picnic areas—this home is a must-see!

3424 Eight Star Way, South Chesapeake
9+AC Butts Station Road, South Chesapeake
$500,000
10518422 MLS
LAND this wonderful opportunity to own 3 wooded parcels spanning 10.34 acres with ~190 ft of Butts Station Rd frontage in the quickly developing area of Centerville and Butts Station Road! This listing is combined and must be sold with .35AC Butts Station Rd MLS #10518421 and .39AC Butts Station Rd MLS #10518419 for total listing price of $750K. Possible uses include agricultural, commercial and residential. Contact today to discuss and see this great investment opportunity!

9+AC Butts Station Road, South Chesapeake
2200 Edwin Drive, South Chesapeake
$499,990
2 Beds ⋅ 2 Baths ⋅ 10627377 MLS
The Asheville, one of our quad-style homes, features two bedrooms and 2 full baths. Refreshing and cottage-like, The Asheville is single level living at its finest. A welcoming covered front porch leads you to a spacious living room with fireplace. At the heart of the home, the Kitchen is within reach of the dining room, pantry, laundry room, and access to the two-car garage. The Kitchen is accented with Shaker style cabinets, quartz countertops, tile backsplash, and stainless-steel appliances. The primary bedroom with ensuite offers a spacious walk-in closet, tiled shower with glass enclosure, counter-height vanity with double sinks and a separate water closet. For guests or an office, you’ll find a secondary bedroom with an adjacent full bath. $10,000 closing cost incentive with use of preferred lender!

2200 Edwin Drive, South Chesapeake
509 Cassway Arch, South Chesapeake
$499,900
4 Beds ⋅ 2.1 Baths ⋅ 10652556 MLS
Beautifully remodeled 4-bedroom, 2.5-bathroom home with water views in the sought-after Grassfield area of Chesapeake. This property offers the perfect blend of modern style and everyday comfort. Fresh paint, new flooring, new windows, and modern finishes throughout.Fully renovated bathrooms and an updated kitchen featuring granite countertops, stylish fixtures, and brand-new stainless steel appliances. A large patio door opens to a spacious backyard with a resort-like setting, featuring an inground pool and peaceful water views perfect for relaxing or entertaining.

509 Cassway Arch, South Chesapeake
408 Gloria Drive, South Chesapeake
$499,900
3 Beds ⋅ 2 Baths ⋅ 10633548 MLS
Move in ready updated ranch with 3 BR/2BA loaded with upgrades! New LVP, carpet & ceramic flooring, fresh interior paint, new windows, wrapped exterior trim, updated lighting and all kitchen appliances. Stylishly renovated bathrooms with new vanities. Spacious and bright Florida room offers flex space for relaxing or entertaining. Large fenced backyard with privacy fence and detached workshop for storage or hobbies. Extended driveway and concrete pad for RV, boat, or camper parking. Crawl space with vapor barrier and floored attic for extra storage. Established neighborhood with easy access to shopping, medical facilities and everyday conveniences.

408 Gloria Drive, South Chesapeake
1219 Fairway Drive, South Chesapeake
$499,900
4 Beds ⋅ 3 Baths ⋅ 10613573 MLS
Beautiful well cared for 4 bedroom home with nice open floor plan and two car garage. This home has a large covered front porch. The updated kitchen has beautiful granite counter tops, stainless steel appliances and a gas stove. This home has a huge primary bedroom with a full bathroom. It has updated LVP Flooring throughout most of home. Nice large bedrooms and another full bathroom. There is a finished room over the garage and a full bathroom next to it. The living room is nice and open and opens up to the kitchen. The home also has a nice sized dining room. The light fixtures, fans and hardware are all updated throughout. Nice backyard with a deck. Call today for a appointment to see this beautiful home!

1219 Fairway Drive, South Chesapeake
339 Conservation Crossing, South Chesapeake
$499,900
4 Beds ⋅ 3 Baths ⋅ 10606306 MLS
Incredible value for this neighborhood! Large lot and no HOA. Welcome to 339 Conservation Crossing in Chesapeake! This 4-bed, 3-bath home offers 2,200+ sq. ft. of stylish living. The open layout features a modern kitchen with granite, stainless appliances, and a large island flowing into the dining and living areas. The spacious primary suite includes a walk-in closet, dual vanities, soaking tub, and separate shower. Enjoy evenings on the patio overlooking a landscaped yard. Two-car garage, laundry room, and convenient location near shopping, dining, schools, and interstate access.

339 Conservation Crossing, South Chesapeake
1949 Rockwood Dr, South Chesapeake
$499,900
4 Beds ⋅ 3 Baths ⋅ 10603480 MLS
Welcome to Summer Park! This 4-bedroom, 3-bath home in the sought-after Grassfield school district offers space, style, and convenience. The open floor plan with 9-ft ceilings creates an inviting flow, anchored by a cozy living room fireplace. The kitchen boasts granite countertops and stainless steel appliances, great for everyday living and entertaining. A downstairs bedroom with walk-in closet and full bath provides flexible space for guests or multigenerational living. Upstairs, retreat to the spacious primary suite with tray ceiling and large walk-in closet. The laundry room with cabinets and folding counter makes chores a breeze. Fresh carpet throughout adds comfort and style. Outside, enjoy a new deck and privacy fence—wonderful for gatherings and play.

1949 Rockwood Dr, South Chesapeake
2139 Sunset Maple Street, South Chesapeake
$499,900
4 Beds ⋅ 2.1 Baths ⋅ 10597420 MLS
Welcome to 2139 Sunset Maple, located in beautiful Deer Crossing neighborhood. Feels like country, looks like HOME SWEET HOME. Some features that make this premier living include; OPEN FLOOR PLAN, NEW TANKLESS WATER HEATER, HEATED FLOOR in the primary bathroom and REMOTE CONTROL WINDOW SHADE in the living room. EXTENSIVE SHELVING in the garage. LOTS of storage space! Updated and ready for you to call home. HVAC recently serviced. NO flood insurance required. Ask about the opportunity to assume low interest rate VA loan. Thanks for stopping by.

2139 Sunset Maple Street, South Chesapeake
900 Ricka Court, South Chesapeake
$499,000
4 Beds ⋅ 2.1 Baths ⋅ 10618027 MLS
Welcome home to this charming 4-bedroom, 2.5-bath ranch in the heart of Hickory/Great Bridge! Tucked away in a peaceful cul-de-sac, this home offers true one-level living plus a spacious room over the garage that can be used as a room, office, playroom, or anything you imagine. Step inside to beautifully updated hardwood floors and an inviting layout designed for both comfort and function. The updated primary bathroom gives your daily routine a fresh, modern feel. Outside, enjoy an oversized garage for extra storage or hobbies, and a large, completely fenced backyard for relaxing or entertaining. The stamped concrete patio with a built-in fire pit sets the stage for cozy evenings and memorable gatherings.With its thoughtful updates and prime location near conveniences, schools, dining, and more, this home blends practicality and personality in all the right ways. Come see how easy life can feel at this Hickory/Great Bridge gem!

900 Ricka Court, South Chesapeake
300 Big Pond Lane, South Chesapeake
$499,000
4 Beds ⋅ 2.1 Baths ⋅ 10615125 MLS
Welcome to this charming 4-bedroom, 2.5-bath home in the sought-after Sawyers Mill neighborhood of Chesapeake. Offering 2,327 square feet of well-designed living space, this home blends comfort and functionality. The spacious layout features inviting living areas filled with natural light, perfect for everyday living and entertaining. The kitchen flows seamlessly into the main living spaces, while the generously sized bedrooms include a private primary suite. Enjoy outdoor living in the fully fenced backyard, ideal for pets, play, or gatherings. A 2-car garage provides convenient parking and storage. Located near shopping, dining, parks, and major commuting routes, this home offers space, privacy, and an excellent location.

300 Big Pond Lane, South Chesapeake
748 Clearfield Avenue, South Chesapeake
$499,000
5 Beds ⋅ 3 Baths ⋅ 10606859 MLS
COME CHECK OUT THIS GORGEOUS 5 BEDROOM/3 FULL BATH HOME WITH LARGE MAINTENANCE FREE BACKYARD AND INGROUND POOL. THIS OPEN FLOOR PLAN AND DOWNSTAIRS BEDROOM/FULL BATH OFFER SO MANY LIVING OPTIONS AT JUST UNDER 2650 SQ. FEET. MASTER BEDROOM FEATURES VAULTED CEILINGS, BATHROOM WITH DUAL VANITY, SOAKING TUB, SHOWER AND WALK IN CLOSET. GRANITE COUNTERTOPS IN KITCHEN WHICH OPENS TO EAT IN DINING AREA, LIVING ROOM AND SLIDING GLASS DOORS WHICH OPEN UP TO AN AMAZING PATIO AND POOL AREA, GREAT FOR THOSE WHO LIKE TO ENTERTAIN. ROOM OVER THE GARAGE IS HUGE AND COULD BE USED IN SO MANY DIFFERENT WAYS. PROPERTY IS IN SUCH A CONVENIENT AREA WITH SHOPPING, INTERSTATES, GREAT RESTAURANTS AND MORE. MAKE YOUR APPOINTMENT TODAY!

748 Clearfield Avenue, South Chesapeake
1024 Vineyard Drive, South Chesapeake
$498,000
4 Beds ⋅ 2 Baths ⋅ 10610666 MLS
Come see this charming ranch style home in the sought-after neighborhood of Brandermill, that is all ready for it's new family! From the gleaming floors to the freshly painted walls, the sellers have made it easy for you to just move-in & unpack! This beautiful 4 bedroom home, situated on over a quarter-acre lot, has been well-maintained & loved by the previous owners for 28 years. All of the kitchen & bathroom countertops have been updgraded to Corian & all of the appliances stay with the home. Don't miss the incredibly large, multi-layered deck overlooking the spacious backyard & topped off with an amazing hot tub. With two storage sheds in the back (1 with a workbench) & a walk-in attic that runs the entire length & width of the home, there is no shortage of storage. The attached garage is fitted with it's own AC & Heat source & the home has designated spigots for deep well water access. Newer storm doors have been added to the front door & two back doors for more natural light.

1024 Vineyard Drive, South Chesapeake

Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.

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