South Chesapeake Homes under $300,000

Welcome to South Chesapeake, Virginia—a hidden gem nestled in the heart of Chesapeake County. Known for its vibrant community spirit and picturesque landscapes, South Chesapeake offers a perfect blend of suburban tranquility and urban convenience. With its lush parks, friendly neighborhoods, and access to top-notch schools, this area is ideal for families, young professionals, and retirees alike.

One of the most appealing aspects of South Chesapeake is its diverse housing market, particularly for those seeking homes under $300,000. Whether you're a first-time homebuyer or looking to downsize, you'll find a variety of charming properties that cater to different tastes and lifestyles. From cozy single-family homes to modern townhouses, there’s something for everyone. Many of these homes boast spacious yards, updated interiors, and proximity to local amenities, making them a smart investment for your future.

Living in South Chesapeake means enjoying a rich tapestry of recreational activities and cultural experiences. Spend your weekends exploring the scenic waterways, hiking trails, and community parks that invite outdoor enthusiasts to unwind and connect with nature. The area also features a thriving local dining scene and boutique shopping, ensuring that residents have everything they need right at their fingertips.

With its affordable housing options and welcoming atmosphere, South Chesapeake is not just a place to live—it's a place to call home. Start your journey today and discover the perfect property that fits your budget and lifestyle in this charming Virginia community!

Newest South Chesapeake Homes under $300,000

$300,000

3 Beds ⋅ 2.1 Baths ⋅ 10656711 MLS

Welcome to 1528 Hambledon Loop, a desirable end-unit in Brighton Park at Greenbrier! This 3-bedroom, 2.5-bath home, 2 master bedrooms with ensuites offers a comfortable floor plan with the added privacy and natural light of an end-unit location. Recent updates include a NEW water heater, offering added peace of mind for the next homeowner. Enjoy the convenience of low-maintenance community living with access to neighborhood amenities, including 2 community pools. Ideally located in Chesapeake’s Greenbrier area, close to shopping, dining, entertainment and major roadways. Whether you're a first-time buyer, looking for additional space, or seeking a convenient Chesapeake location, this home is ready for its next owner. Schedule your showing today!

1528 Hambledon Loop, South Chesapeake

$252,000

2 Beds ⋅ 1 Baths ⋅ 10656390 MLS

Affordable Great Bridge lake-view living! Enjoy low-maintenance condo living just off Cedar Road, a short drive from shopping, restaurants, entertainment and everything Great Bridge has to offer. Inside, vaulted ceilings, arched windows and abundant natural light give the home an open, inviting feel. The living room features a cozy fireplace and opens to a private balcony overlooking the lake and mature trees—an ideal spot for morning coffee or winding down at the end of the day. The kitchen offers plenty of cabinet and counter space with a bright dining area highlighted by a dramatic arched window. Two comfortable bedrooms and a full bath complete the home. Residents also enjoy community amenities including the pool, while the location puts you just minutes from the area’s dining, shopping and entertainment. The city’s annual parade route is also just a few blocks away, adding to the convenience and community feel of this Great Bridge location. Whether you’re a first-time buyer, downsizing, or simply looking for an affordable, low-maintenance home in a great location, this lake-view condo offers a lot of value without giving up convenience.

449 E Lake Circle, South Chesapeake

713 Rapidan River Court Unit G, South Chesapeake

$230,000

2 Beds ⋅ 2 Baths ⋅ 10655996 MLS

Freshly transformed and move-in ready! This second-floor corner end-unit condo in Chesapeake's Riverwalk community just had a full cosmetic refresh of the interior, including fresh paint throughout, an updated kitchen, new flooring and more. The single-level layout offers 2 bedrooms and 2 full baths. A wood-burning fireplace anchors the living area, and a private balcony overlooks mature trees. The primary suite has its own full bath. Beyond the cosmetic work, the home also has newer windows and a newer HVAC system. Kitchen appliances convey along with an exterior storage shed and two assigned parking spaces. The condo fee includes water, trash, grounds maintenance, the community pool and clubhouse.

713 Rapidan River Court Unit G, South Chesapeake

$289,900

2 Beds ⋅ 1.1 Baths ⋅ 10655553 MLS

Welcome to this beautifully refreshed 2-bedroom, 1.5-bath townhome tucked away on a quiet cul-de-sac in sought-after Las Gaviotas. Head inside to a spacious living area featuring a cozy brick fireplace and an inviting floor plan perfect for relaxing or entertaining. Recent updates include fresh paint, new flooring and carpet, updated full bath, new rear deck, front porch railing, sliding glass doors, gutters, and water heater. Energy-efficient windows and kitchen appliances were replaced in 2020. Upstairs offers two generously sized bedrooms, a dual-entry full bath, and large hall closet for extra storage. Enjoy a private fenced backyard and new deck, perfect for morning coffee, grilling, or unwinding. Conveniently located near shopping, dining, parks, interstates, Chesapeake City Hall, and Grassfield schools. Move-in ready and waiting for its new owner!

300 San Roman Drive, South Chesapeake

$230,000

2 Beds ⋅ 2.1 Baths ⋅ 10655183 MLS

Charming 2 bedroom 2.5 bath condominium near shopping, restaurants and close access to interstates and Chesapeake Regional Hospital. Located within the B.M. Williams district, a designated Purple Star school supporting military-connected families. Home has double walk-in closets, all new LVP flooring, fresh paint, privacy fence and patio. Brand new light fixtures and ceiling fans. Seller willing to give appliance allowance with acceptable offer.

618 Ridge Circle, South Chesapeake

$220,000

2 Beds ⋅ 1 Baths ⋅ 10655259 MLS

Welcome to this cozy 2 bedroom, 1 bathroom ranch home located in the heart of Deep Creek! This home offers a comfortable layout, an attached 1-car garage, and a spacious backyard with a privacy fence, providing plenty of room for outdoor enjoyment. The large detached shed/workshop offers additional storage and space for hobbies or projects. With its charming touches, great outdoor space, and convenient location near shopping, dining, and major roadways, this home is ready for its next owner to make it their own!

2704 George Dr Drive, South Chesapeake

$300,000

3 Beds ⋅ 2.1 Baths ⋅ 10654893 MLS

Largest floor plan in the neighborhood! Lovingly maintained and thoughtfully updated, this spacious brick townhome is tucked away on a quiet cul-de-sac in the heart of Chesapeake. Enjoy a private, fully fenced backyard with no homes directly behind you and no HOA. Inside, you’ll find fresh paint, new carpet and flooring, updated bathrooms, new fixtures and hardware, and gleaming hardwood floors. The brand-new kitchen features granite countertops, stainless-steel appliances, a gas range, and full-size refrigerator. A wood-burning fireplace adds warmth and character, while abundant natural light fills the home. Plenty of indoor and outdoor storage provides added convenience. With a low-maintenance brick exterior, spacious floor plan, thoughtful updates, and a private backyard, this home is truly move-in ready. Pride of ownership is evident throughout—come see it today!

302 Fairfax Terrace, South Chesapeake

$299,999

3 Beds ⋅ 1.1 Baths ⋅ 10654604 MLS

Solid Bones. Endless Potential. Bring Your Vision. In the heart of Greenbrier. This all brick ranch with attached 1 car garage has a huge fenced back yard with large storage shed . Property has been very well maintained. Convenient to shopping, interstates, Hospital and restaurants. This is a rare chance to own a home with a strong, well-built structure and the freedom to make it your own. Great property for the investor, renovator, or hands-on buyer who can see what the home can become. Solid structure, a great foundation for a remodel. Needs vision and a little TLC. Room to build equity through updates. Sold strictly as-is, where-is. Seller makes no repairs or warranties. Buyers are encouraged to complete their own inspections and due diligence. Please submit offers through the property’s listing page on www.auction.com/privateseller.

205 Thrasher Road, South Chesapeake

816 Shenandoah River Road, South Chesapeake

$295,000

2 Beds ⋅ 2 Baths ⋅ 10654480 MLS

Welcome to 816 Shenandoah River Road! Spacious 2 bedroom 2 bathroom condo tucked away in established Riverwalk! This move in ready home offers a cool modern feel with many updates throughout. Main living area welcomes you with fresh paint and LVP flooring. Kitchen has been updated to include custom cabinetry, quartz countertops and tile backsplash. One bedroom / bath occupy first floor and One bedroom / bathroom occupy second floor. Association is responsible for all exterior maintenance to include grounds and roof. Skylights were replaced in 2026. Enjoy all the riverwalk community has to offer, including Clubhouse, Pool, Tennis Courts, Boat Ramp, Playgrounds, Walking Trails and trash pickup.

816 Shenandoah River Road, South Chesapeake

1012 Willow Green Court, South Chesapeake

$207,000

2 Beds ⋅ 2 Baths ⋅ 10654027 MLS

Move-in ready and meticulously maintained is this first-level 2BR/2BA condo in Chesapeake's sought-after Riverwalk. Greenbrier area. It is the perfect blend of comfort and convenience. Step inside to beautiful LVP flooring and newer paint in the living and dining areas, plus freshly cleaned carpet in both the bedrooms. Generous sized Primary Ensuite. Your private fenced patio with storage shed is ready for morning coffee or weekend grilling. Two assigned parking spaces right at your front door. Willow Point Association maintains it's well appointed landscaped, pool, and trash pickup. Come home and just relax. Close to schools, hospital, restaurants, shopping and interstates. Great location.

1012 Willow Green 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

$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

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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.