South Chesapeake Real Estate

Welcome to South Chesapeake, a charming city nestled in the heart of Virginia. Located in Chesapeake County, South Chesapeake offers the perfect blend of suburban tranquility and urban convenience.

With its picturesque neighborhoods, top-rated schools, and a strong sense of community, South Chesapeake is an ideal place to call home for families, young professionals, and retirees alike. The city boasts a thriving real estate market, with a variety of housing options to suit every lifestyle and budget.

Nature enthusiasts will appreciate South Chesapeake's proximity to the Great Dismal Swamp National Wildlife Refuge, where outdoor adventures abound. From hiking and birdwatching to kayaking and fishing, there's no shortage of ways to enjoy the great outdoors in this beautiful region.

Conveniently located near major highways and just a short drive from Virginia Beach and Norfolk, South Chesapeake offers easy access to a wealth of shopping, dining, and entertainment options. Whether you're looking to explore the vibrant arts scene, relax on the beach, or indulge in some retail therapy, you'll find plenty to love about living in South Chesapeake.

Come discover all that South Chesapeake has to offer and find your perfect place to call home in this vibrant and welcoming city.

Newest Listings in South Chesapeake

$500,000

4 Beds ⋅ 2.1 Baths ⋅ 10647583 MLS

This amazing home Sits on a large corner lot. Has a large Living space with fireplace. Huge Master bedroom with large walk-in closet. The other bedrooms are nice size. Nice size dining room, office space, Breakfast area. The sellers is getting ready to install new kitchen cabinets and counter tops. And installing a new pool liner. The pool pump is only a year old. The AC compressor is 2 years old. Has a large deck in back yard for entertaining. Backyard fenced in.

224 Springbrook Lane, Chesapeake

$625,000

4 Beds ⋅ 2.1 Baths ⋅ 10647389 MLS

MUST SEE 4 BR, 2.5 BATH HOME IN SOUGHT AFTER ETHERIDGE LAKES NEIGHBORHOOD. HOME SITS ON A LGE FENCED YARD, W/2CAR GARAGE AND PLENTY OF DRIVEWAY SPACE. KIT UPDATES INCLUDE TOP OF THE LINE SS APPLIANCES, INDUCTION STOVE, NEW FLOORING & PAINT. LGE PBR WITH SITTING/FLEX RM, ENSUITE BATH HAS BIG CLOSET, DOUBLE SINKS, JETTED TUB & STANDUP SHOWER. NICE SIZE BR'S, ALOT OF STORAGE INCLUDING A WALK-IN AREA BEHIND BED IN PBR. SUNRM ADDED IN '22, WINDOWS '21, ROOF '20, HVAC '19, HTWTR TANK '23. CHECK OUT THE HIGHLY RATED SCHOOLS. HOUSE KEPT UNDER TERMITE/MOISTURE CONTRACT. TAKE A LOOK, YOU WILL LIKE WHAT YOU SEE. QUICK CLOSING

1805 Crestwynd Drive, Chesapeake

$208,000

3 Beds ⋅ 1 Baths ⋅ 10647527 MLS

Brick ranch home with 3 bedrooms, 1 bath. Living room and dining room adjacent to kitchen. Convenient to interstates, shopping, entertainment and schools. Rooms are nicely sized and you have great sunlight throughout. 1 car attached garage, large yard.

1140 Woodland Terrace Drive, Chesapeake

$7,900

10647463 MLS

Vacant Land in Hillcrest subdivision. Zoned for great schools! Drive by anytime. Seller has never occupied the land, has no information to share. Buyer to perform all due diligence.

14 Blk Tuck Street, Chesapeake

$315,000

3 Beds ⋅ 2.1 Baths ⋅ 10647260 MLS

Welcome home to this beautifully maintained 3-bedroom, 2.5 bath townhome offering over 1,600 square feet of comfortable living space—and no HOA! Pride of ownership shines throughout this move-in-ready home featuring an upstairs laundry for added convenience and a security system that's already wired and ready for activation. Major updates provide peace of mind, including a new roof (2016), kitchen appliances and refrigerator (2021), washer and dryer (2023), and water heater (2026). Whether you're a first-time buyer, downsizing, or looking for an investment opportunity, this well-cared-for home offers the perfect combination of comfort, value, and convenience.

703 Hunters Quay, Chesapeake

$845,000

5 Beds ⋅ 4.1 Baths ⋅ 10647443 MLS

The Macon Multi-Gen at Riverview Landing - Master Model Listing by Wetherington Homes. Buyers may select their lot and personalize available design options. Thoughtfully designed with approximately 3,535 sq. ft. of living space and a 3-car garage, the MM Macon Multi-Gen offers exceptional flexibility for today’s lifestyles. This home features a private multi-generational suite complete with a living room, bedroom, full bath, and washer/dryer hookup, with an optional kitchenette for added convenience. Ideal for extended stays, guests, or multi-generational living. Enjoy a convenient location close to schools, shopping, restaurants, and more! Contact our Sales Counselor today to learn more.

MM Macon-Multi-Gen, Chesapeake

$922,500

5 Beds ⋅ 4 Baths ⋅ 10647253 MLS

Exceptional all-brick custom home nestled in the heart of Great Bridge, meticulously maintained and thoughtfully designed with a floor plan you’re sure to love. Offering 5 spacious bedrooms and 4 full bathrooms, this home also features a versatile first-floor flex room with adjacent full bath ideal as a 6th bedroom, home office, playroom, or guest suite. The private, beautifully landscaped backyard creates the perfect retreat, complete with a patio and full-yard irrigation system. Built as the builder’s personal residence, the home showcases quality craftsmanship and upscale details throughout, including extensive custom trim work and abundant storage. Additional highlights include a garage loft with extra storage space, dual heat pump/HVAC systems for comfort and efficiency, a large walk-in closet, oversized pantry, generous laundry room, and spacious secondary bedrooms. A rare opportunity to Buy a truly well-crafted custom home in one of Great Bridge’s most desirable locations.

138 Greengable Way, Chesapeake

$425,000

3 Beds ⋅ 2.1 Baths ⋅ 10646703 MLS

Welcome home to this beautifully maintained 3 bedroom, 2.5 bath home featuring an open-concept layout with soaring ceilings and a versatile loft. Luxury vinyl plank flooring flows throughout the first floor, creating a stylish and low-maintenance living space. The spacious primary suite offers a private en suite bath, while generously sized secondary bedrooms provide flexibility for a variety of needs. Enjoy the convenience of a two-car garage and a fully fenced backyard - perfect for outdoor entertaining, pets, or play. Energy-efficient solar panels help reduce monthly electric costs. Ideally situated with easy access to shopping, dining, major highways, military bases, and everyday conveniences. Plus, receive 1% toward closing costs when using preferred lender. Don't miss this exceptional opportunity!

711 Pile Avenue, Chesapeake

$16

10647380 MLS

Excellent location directly off Executive Blvd. 1975 SF space located in the heart of the Greenbrier Submarket. Two story build out with office space, full bath, warehouse, and mezzanine available with current layout. Two dedicated parking spaces with several more open parking spaces available on a first come basis. Tenant is responsible for electric, janitorial, and telecommunications. Water is provided in rent. Rent is $2,550 per month. Landlord may be willing to provide up to 2 months off rent to help tenant with build-out expenses. Landlord will provide lease agreement.

1222 Executive Boulevard Unit 104, Chesapeake

$675,000

5 Beds ⋅ 3 Baths ⋅ 10647378 MLS

Meticulously maintained 5-bedroom, 3-bath home in sought-after Las Gaviotas offering over 3,000 sq ft of bright, open living space with water views. Flexible layout includes 1st floor bedroom and bath, huge FROG can be bedroom, office, flex space. 2 Bathrooms feature updated Onyx showers for a modern touch. Enjoy a private, wooded backyard overlooking the canal—perfect for relaxing or entertaining. Ample storage throughout. A whole-house generator provides peace of mind, and no flood insurance is required. Community includes a pool, clubhouse, and golf - pool and golf have optional membership. Don’t miss this exceptional cul-de-sac opportunity!

504 Aguila Court, Chesapeake

$604,900

3 Beds ⋅ 2.1 Baths ⋅ 10647287 MLS

Nestled in Greenbrier, Joseph’s Meadow is the newest community by a renowned local builder. The Primrose Cottage welcomes you with a charming full front porch, soaring two-story family room, and beautiful Mohawk flooring throughout the main living areas. Designed for effortless living and entertaining, the open layout connects the family room, dining area, and HGTV-inspired chef’s kitchen featuring oversized quartz island, custom hood & floating shelves, designer finishes, and mudroom. The first-floor primary suite offers a custom walk-in closet, spa-like bath with quartz dual vanity, tiled shower, and private laundry. Upstairs two spacious bedrooms, tons of storage and large laundry room. (Opt. to add 4th BR or Loft) Professionally managed grounds provide a low-maintenance lifestyle, giving you more time to enjoy the comfort, quality, and craftsmanship of your Primrose haven. To be built to your specs from designer showroom. Intimate neighborhood with limited building opportunities.

MM Primrose A, Chesapeake

$525,900

4 Beds ⋅ 3.1 Baths ⋅ 10647286 MLS

First Time Buyer 5.75 rate, low down, 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!

903 Bernard Lane, Chesapeake

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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.