South Chesapeake Real Estate

Welcome to South Chesapeake, Virginia—a hidden gem that beautifully marries suburban tranquility with urban convenience. Nestled within the vibrant city of Chesapeake, this charming community offers a unique blend of natural beauty and modern living, making it an ideal place to call home.

South Chesapeake is characterized by its picturesque landscapes, featuring lush parks, serene waterways, and scenic trails perfect for outdoor enthusiasts. With its proximity to the Great Dismal Swamp National Wildlife Refuge, residents can enjoy a variety of recreational activities, from hiking and birdwatching to kayaking and fishing. The area's commitment to preserving green spaces ensures that nature is never far away.

Convenience is key in South Chesapeake, as the community is strategically located near major highways, providing easy access to nearby cities such as Norfolk and Virginia Beach. This connectivity allows residents to enjoy a wealth of shopping, dining, and entertainment options while returning to their peaceful retreat at the end of the day.

Families will appreciate the top-rated schools in the Chesapeake Public School system, along with a strong sense of community that fosters connections among neighbors. Local events and festivals throughout the year bring residents together, creating a warm and inviting atmosphere.

Whether you're seeking a cozy starter home, a spacious family residence, or a charming retirement retreat, South Chesapeake has something for everyone. Experience the perfect blend of community spirit, natural beauty, and modern convenience—come discover your new home in South Chesapeake, VA!

Newest Listings in South Chesapeake

$256,900

2 Beds ⋅ 1 Baths ⋅ 10646087 MLS

WELCOME TO THIS BEAUTIFUL HOME, WHETHER YOUR LOOKING FOR YOUR FIRST HOME OR DOWNSIZING THIS PROPERTY SITUATED IN THE WELL KEPT NEIGHBORHOOD OF DEEP CREEK. SET ON A HUGE LOT WITH DETACHED PRIVATECY FENCED PATIO FOR RELAXING AND AN OVERSIZED GARAAGE/WORK SHOP WITH GARAGE DOOR OPENER. THE HOME ALSO OFFERS SPACIOUS LIVING ROOM AND A BEAUTIFUL KITCHEN THAT HAS BEEN RECENTLY RENOVATED. FRIG, RANGE, NEWER WASHER AND DRYER MATCHING SET CONVEY. REPLACEMENT WINDOWS, 3 YEAR OLD ROOF AND TERMTE LETTER PPROVIDED. TAKE A LOOK AND END YOUR SEARCH!

2312 Ferndale Road, South Chesapeake

$330,000

2 Beds ⋅ 2.1 Baths ⋅ 10646077 MLS

This end-unit townhome in the desirable Riverwalk community offers a functional layout, thoughtful updates, and exceptional amenities. Upstairs you will find two spacious bedrooms, both with ensuite bathrooms. The open-concept first floor seamlessly connects the living room, dining area, and kitchen, with durable LVP flooring throughout the main level and continuing upstairs. The kitchen is equipped with granite countertops and stainless steel appliances, while the gas fireplace adds warmth and charm to the living space. Enjoy relaxing on the screened porch overlooking your fenced backyard. Major updates have already been completed, including a new HVAC system (2025), water heater (2024), and a roof approximately seven years old. Additional highlights include an attached garage and access to Riverwalk's outstanding community amenities, including a pool, tennis courts, and clubhouse. Conveniently located near shopping, dining, and major commuter routes, make this one your next home!

312 Esplanade Place, South Chesapeake

$470,000

4 Beds ⋅ 2.1 Baths ⋅ 10646065 MLS

3404 Winterhawk Court, South Chesapeake

$215,900

2 Beds ⋅ 1 Baths ⋅ 10645553 MLS

Welcome home to the heart of Greenbrier! This charming and stylish 2-bedroom, 1-bath second-floor condo in the desirable Heather Pointe Condominiums offers the perfect combination of comfort, convenience, and updates. Conveniently located behind Greenbrier Mall, you'll enjoy easy access to shopping, dining, entertainment, and major interstates. The beautifully remodeled kitchen (2021) features granite countertops, upgraded soft-close cabinets, ceramic tile backsplash and flooring, stainless steel Whirlpool refrigerator, microwave, dishwasher, and a new electric range (2026). All appliances, including the washer and dryer, convey. Relax by the cozy gas fireplace in the spacious living room or enjoy your private balcony. New carpet throughout the home makes this condo move-in ready. Don't miss this wonderful opportunity—schedule your private showing today!

1709 Rock Bridge Mews Unit B, South Chesapeake

$300,000

3 Beds ⋅ 1.1 Baths ⋅ 10646018 MLS

Ideally located in the heart of Greenbrier, this move-in-ready three-bedroom townhouse is the perfect find! Recently refreshed with updated flooring and renovated bathrooms, this home is ready for its new owners. Features include a spacious kitchen with plenty of counter space, a convenient laundry area, and roomy, comfortable bedrooms. Complete with a private, fenced-in backyard and patio, this home offers everything you need. Schedule your showing today!

1204 Cedar Mill Square, South Chesapeake

$575,000

5 Beds ⋅ 2 Baths ⋅ 10646017 MLS

FRESH EGGS, BIG FREEDOM, ENDLESS POTENTIAL in Chesapeake's desirable Blackwater area! Welcome to your private sanctuary—the ultimate lifestyle upgrade. Picture sipping morning coffee while collecting farm-fresh eggs from your backyard chickens, surrounded by peaceful green space. Enjoy pure, independent water from your premium 600+ ft Certified Artesian well, complete with a double tank water softener and an energy-efficient tankless electric water heater. Dream big with future-proof infrastructure: an oversized septic system is already in place to support an ADU, multi-generational living, or rental income. Built for comfort and efficiency, this ultimate hobbyist setup includes a premium dual-fuel HVAC and a sub-panel wired for a generator. Whether you envision a luxury guest cottage, a workshop, or an expanded country compound, the foundation is completely set. Schedule your tour today!

1336 Blackwater Road, South Chesapeake

$365,000

3 Beds ⋅ 1 Baths ⋅ 10645994 MLS

944 Bells Rd Road, South Chesapeake

$427,000

4 Beds ⋅ 2.1 Baths ⋅ 10645995 MLS

Welcome to your dream home in Chesapeake! This meticulously maintained end-unit condo blends modern luxury with effortless living, offers 4 bedrooms, 2.5 bathrooms, and beautifully upgraded living spaces. Go inside to an airy open-concept layout with vaulted ceilings, crown molding, and luxury vinyl flooring. Enjoy upgraded recessed lighting, pendant lights, and modern ceiling fans. The chef's kitchen, renovated in 2023, features new cabinets, granite counters, and premium stainless steel appliances. Major systems have been updated, including a water heater (2022) and HVAC (2024). The 1st floor ensuite is a private retreat with custom built-in shelves, walk-in closet, and spa-like bathroom with double sinks and a jetted tub. Upstairs, 2 additional bedrooms share a dual-entry bathroom with double sinks, offering great privacy for family or guests, and a large bonus loft area. Parking includes an attached garage and 2-space driveway. Welcome home to style, space, and convenience!

713 Tiffany Green Court, South Chesapeake

$550,000

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

$389,900

3 Beds ⋅ 2.1 Baths ⋅ 10645889 MLS

This adorable 2-story, Townhouse-style, end-unit condo is conveniently located in sought after Hampshires @Greenbrier. The 1st floor features an open-concept layout consisting of an inviting foyer that flows into the formal dining room, Primary bedroom w/ensuite bathroom, walk-in closet, updated kitchen boasts quartz counter tops, stainless steel appliances, ample counter space, loads of cabinets for storage, family room w/cozy gas fireplace, utility closet, a powder room off the hallway for guests and access to the attached, 1- car garage & fenced-in patio area. The carpeted stairs lead to the 2nd floor that features 2 additional bedrooms, one w/an en-suite bathroom and large walk-in attic. Highlights include: some hardwood flooring, neutral carpet, lots of natural light & MORE! Neighborhood amenities include: a clubhouse, community pool & ample guest parking. Great central location adjacent to shopping, schools, parks, local beaches & highway access for an easy commute. Welcome Home!

1472 Otterbourne Circle, South Chesapeake

$445,000

4 Beds ⋅ 2 Baths ⋅ 10645914 MLS

Situated on a .61-acre lot, this home is move-in ready with many recent updates. Major updates include a brand new HVAC system, new crawlspace dehumidifier, and freshly painted interior. Other recent updates include (2024) water heater, (2022) refrigerator & dishwasher, French drain, and LeafFilter gutter guards. Outside is where this property really stands apart. A 3,000-lb capacity stainless steel bridge with Trex planks spans the 36-foot creek and connects to additional yard space on the other side. Imagine the possibilities for this unique extension of the property! A double driveway with turnaround area, attached garage and patio add even more functionality.

925 Johnstown Road, South Chesapeake

$510,000

4 Beds ⋅ 2.1 Baths ⋅ 10645829 MLS

WELCOME HOME! Tucked away on a quiet cul de sac and set on nearly an acre backing to peaceful woods, this beautifully maintained home offers the perfect blend of privacy, outdoor living, and everyday convenience. Whether you’re enjoying your morning coffee in the screened gazebo or entertaining family and friends, you’ll appreciate the peaceful setting this property provides. Inside, you’ll find stainless steel appliances, a spacious walk in pantry, a cozy gas fireplace, and thoughtful updates throughout, including a new roof installed in 2024. A transferable 2-10 Home Warranty provides added peace of mind for the next owner. Conveniently located near Interstate 64, Route 17, shopping, dining, and major military installations throughout Hampton Roads, this home offers the ideal balance of tranquility and accessibility. Don’t miss your opportunity to make this exceptional property your next home. Schedule your private showing today!

104 Bishops Court, 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.