South Chesapeake Real Estate

South Chesapeake Real Estate

Welcome to South Chesapeake, Virginia—a hidden gem that perfectly blends suburban tranquility with vibrant community life. Nestled in the heart of Chesapeake, this charming area offers residents a unique combination of lush landscapes, rich history, and modern amenities, making it an ideal place to call home.

South Chesapeake is renowned for its family-friendly atmosphere, featuring a variety of parks, recreational facilities, and top-rated schools that cater to all ages. With expansive green spaces like the stunning Chesapeake City Park and the serene Deep Creek Park, outdoor enthusiasts can enjoy hiking, picnicking, and sports activities throughout the year. The community also hosts seasonal events, fostering a strong sense of connection among neighbors.

Culturally rich, South Chesapeake is steeped in history, with nearby attractions that showcase the area’s heritage. Explore the historic Great Bridge Battlefield Park or visit the Chesapeake Historical Museum to learn about the city’s past and its pivotal role in American history.

Convenience is key in South Chesapeake, with easy access to major highways and proximity to the bustling cities of Norfolk and Virginia Beach. Residents can enjoy a myriad of shopping, dining, and entertainment options, from local boutiques to popular chain stores and restaurants offering diverse cuisines.

Whether you’re a first-time homebuyer, a growing family, or looking to downsize, South Chesapeake offers a welcoming community and a variety of housing options to suit your needs. Experience the charm and warmth of South Chesapeake—where your dream home awaits!

Newest Listings in South Chesapeake

543 Bright Red Run, South Chesapeake
$399,900
3 Beds ⋅ 2.1 Baths ⋅ 10660236 MLS
Immaculately maintained & better than new, this 2022 Craftsman-style end-unit townhome is in the sought-after Grassfield School District. The open-concept layout features a light-filled Great Room & gourmet kitchen with Quartz countertops, white shaker cabinetry, stainless steel appliances, gas range, oversized breakfast bar, & pantry. LVP flooring spans the first floor. Upstairs, the spacious primary suite boasts a double tray ceiling, walk-in closet, & en-suite bath with dual vanity & oversized tiled shower with built-in bench. Two additional bedrooms, 2.5 baths, laundry room, tankless water heater, and all appliances convey. Enjoy outdoor living on the patio, just a short walk from community amenities including walking trails, playground, dog park, splash pad, & covered pavilion. Ground maintenance included. Convenient to shopping, dining, military installations, & major interstates. Assumable VA loan at an attractive 3.5% interest rate! Call for details.

543 Bright Red Run, South Chesapeake
636 Appalachian Court, South Chesapeake
$535,000
3 Beds ⋅ 2.1 Baths ⋅ 10660204 MLS
NO HOA. Experience fine details in an exquisite landscaped setting. This wonderful 3-bedroom, 2.5 bath home features a First Floor Primary. Upon entering, there is a Foyer with Central staircase. Dining room/Flex room. Gorgeous, sparkling Gourmet Kitchen with in wall microwave and wall oven, outside vented Range hood & 5 burner gas Cooktop, large Kitchen Island, quartz, pendant lights and a farmhouse sink. Cozy Living space w/Gas Fireplace. Down the hall is a guest bath and laundry, as well as an entrance to a spacious 2-car garage. First Floor Primary Bedroom with Elegant and Modern Tiled shower. 2 large bedrooms spaces upstairs with a 2nd Hall bath. Walk in Storage Area. Sought after location.

636 Appalachian Court, South Chesapeake
208 Leicester Court, South Chesapeake
$760,000
5 Beds ⋅ 3 Baths ⋅ 10660322 MLS
Beautiful 5 Bedroom Brick Home featuring a spacious open floor plan perfect for everyday living and entertaining. The large kitchen offers stainless steel appliances, lots of counter space and cabinets. A standout feature of the home is the custom library, complete with French doors, built-in shelving, and a rolling ladder, creating an elegant and inviting space for work, reading, or relaxation. The first floor includes a guest bedroom and full bath. Upstairs you'll find a media room and an oversized primary suite with double closets and a large beautiful bathroom featuring a jetted tub, separate shower, a double vanity and private toilet room. Be sure to notice the built-in light-up stairs going up to the second floor! Enjoy your own private backyard oasis with mature landscaping, an in-ground saltwater pool, hot tub, and an expansive custom paver patio, ideal for relaxing or entertaining. Extended driveway with Boat/RV pad. Located in the sought after Great Bridge school district and community, local shops and restaurants, and close to the interstate for a quick trip to OBX!

208 Leicester Court, South Chesapeake
1400 Dons Way, South Chesapeake
$529,900
4 Beds ⋅ 3.1 Baths ⋅ 10660222 MLS
Immaculately maintained & better than new, this stunning end-unit townhome in Greenbrier is move-in ready! The entry level offers a 1-car garage, bedroom, full bath, flex room, mudroom with built-ins, & access to the fenced patio. The main level features an open-concept design with a sun-filled Great Room, electric fireplace, dining area, & gourmet kitchen boasting Quartz countertops, white shaker cabinetry with under-cabinet lighting, stainless steel appliances, oversized breakfast bar, & large pantry. Durable LVP flooring spans the first and second levels. The third-floor Primary Suite includes a spacious walk-in closet & private bath with dual vanities, Quartz counters, & a tiled shower. Two additional bedrooms, a full bath, & laundry complete the upper level. All appliances convey. Conveniently located near Greenbrier Mall, dining, medical facilities, military installations, interstates, and tunnels. *Assumable 5.75% VA loan available; Call for details.

1400 Dons Way, South Chesapeake
309 Barcelona Drive, South Chesapeake
$530,000
4 Beds ⋅ 3 Baths ⋅ 10660115 MLS
Picture perfect front porch nestled in Las Gaviotas golf course community. Gardeners paradise in the backyard with wild flowers, strawberries and so much more. Deluxe playground and lots of fun built-in for backyard summer days. Spacious bedrooms with a lot of closet space. Big attic is amazing for storage. There is so much potential in this home nestled on a large lot with a great floor plan and freshly painted throughout. Expansive kitchen with center island and modern farmhouse touches throughout.

309 Barcelona Drive, South Chesapeake
409 Cairns Road, South Chesapeake
$729,900
4 Beds ⋅ 2.1 Baths ⋅ 10660244 MLS
Make this your first stop! Pride of ownership shines throughout this immaculate Hickory Landing home that has been exceptionally cared for by the seller. The open floor plan offers a great flow between the living spaces, with updated flooring and fresh paint throughout giving the home a clean, move-in-ready feel. The spacious kitchen features granite countertops, a large island, gas range, butler's pantry, and plenty of cabinet space. The primary suite offers generous closet space and a beautifully tiled ensuite bath, while the additional bedrooms provide plenty of room for family or guests. Step outside to your own backyard oasis featuring an in-ground pool, putting green, quality storage shed, and plenty of space to entertain. Located in the highly sought-after Hickory School District, this home offers the space, condition, and location you've been looking for!

409 Cairns Road, South Chesapeake
891 Bells Mill Road, South Chesapeake
$525,000
4 Beds ⋅ 3.1 Baths ⋅ 10660202 MLS
Welcome Home! Privacy, functionality, and convenience come together in this exceptional Grassfield property! Set back from the street along a private driveway, this nearly one-acre property is surrounded by mature woods and lush greenery. Inside, fresh paint and a flexible floor plan offer something for everyone. A rare find, the home features two distinct main-level suites, including an in-law suite with its own living room, great for multi-generational living, extended guests, a fifth bedroom, or home office. The primary bathroom features live-edge wood countertops, dual showerheads, and a custom walk-in closet system. Outside, enjoy a storage shed, chicken coop, separate hookups for a future pool and hot tub, and a massive detached two-car workshop/garage with carport and RV hookup. Over $17,000 in crawlspace work has been completed, and a survey is available in the listing documents. A truly unique Grassfield property offering flexibility and room to make it your own!

891 Bells Mill Road, South Chesapeake
1108 Hillside Trace, South Chesapeake
$545,000
4 Beds ⋅ 2.1 Baths ⋅ 10660208 MLS
Enjoy cul-de-sac living in this beautifully appointed well maintained 4-bedroom, 2.5-bath home featuring a 2-car garage! The home offers bamboo wood flooring downstairs, den with gas fireplace, formal living and dining rooms, and a kitchen with breakfast nook. Primary suite with cathedral ceiling and updated bath with tile shower and dual sinks. Sliding glass door off kitchen to deck, fenced backyard is perfect for entertaining with large patio with fire pit, and storage shed. Water heater replaced in 2025, all appliances convey, and seller will provide a home warranty up to $1,000 at closing.

1108 Hillside Trace, South Chesapeake
909 Sydenham Boulevard, South Chesapeake
$700,000
6 Beds ⋅ 3 Baths ⋅ 10660198 MLS
909 Sydenham Welcome to this spacious 6-bedroom home on a desirable corner lot, offering plenty of room to spread out and enjoy all that this home has to offer. With one bedroom conveniently located downstairs, the layout provides flexibility for guests, a home office, or multigenerational living.Step outside and enjoy your private pool, great for summer days, entertaining, and making memories at home. Recent updates provide added peace of mind, including a 2021 roof and a 2023 pool liner and pool heater.With six bedrooms, a corner-lot setting, and a pool, 909 Sydenham offers the space, flexibility, and outdoor living you’ve been looking for. Come see all this home has to offer!

909 Sydenham Boulevard, South Chesapeake
1451 Rollesby Way, South Chesapeake
$330,000
2 Beds ⋅ 2.1 Baths ⋅ 10660184 MLS
Lovely 2 primary bedroom condo with an extra room on the 1st floor in the lovely Greenbrier area. Lot's of upgrades throughout and very well cared for. A better deal than todays new construction! Newer LVP flooring on the 1st floor and newer plush carpet on the 2nd floor. Lovely kitchen with stainless appliances and solid surface countertops. Newer updated paint throughout. Priced to sell quickly! Condo fee of $387 covers water, sewer, trash pick up, landscaping, access to the neighborhood pool, and even the roof maintenance. This area is super convenient to the mall, golf course, bases, shopping, schools, churches and just a short way to the interstate. An awesome place to call home! Beautiful easy care living. Don't miss this beauty!!!

1451 Rollesby Way, South Chesapeake
1605 Mary Lou Lane, South Chesapeake
$475,000
3 Beds ⋅ 2.1 Baths ⋅ 10659685 MLS
Welcome to 1605 Mary Lou Lane in Cardinal Meadows! Built in 2022, this beautifully maintained condo feels brand new, with new carpet throughout and nearly 2,300 sq. ft. of stylish, low-maintenance living. The bright, open main level features high ceilings and a gorgeous kitchen with upgraded cabinetry and quartz countertops. A builder upgrade provides a larger first-floor primary suite and upstairs bedrooms than most homes in the community! The primary suite features a dual-vanity bath and walk-in closet. Upstairs offers a versatile loft, two bedrooms with walk-in closets, a full bath, and walk-in storage with potential for future finished space. Enjoy your private oasis with a newly fenced backyard backing to peaceful woods. Community amenities include a pavilion with grill, splash pad, playground, dog park, and walking trails. Conveniently located near Grassfield schools, shopping, and major interstates. Move-in ready!

1605 Mary Lou Lane, South Chesapeake
313 N Centerville Turnpike, South Chesapeake
$400,000
3 Beds ⋅ 2 Baths ⋅ 10660096 MLS
Updated kitchen includes the appliances, flooring, cabinets, countertops. replacement windows and vinyl soffitt.nclosed sun porch with large windows connects home to garage. Red barn at the far back area of the large, private back yard is 704 sq ft, built in 1990. There is a small storage shed immediately behind the house and concrete patio. The water heater is approx four years old; selling home as is, sellers to do no repairs. There is a mandatory City water main connection deadline of August 1, 2027. Owners have not paid any connection fees. Letter from City of Chesapeake is available for review.

313 N Centerville Turnpike, South 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.

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