South Chesapeake Homes under $300,000

Welcome to South Chesapeake, Virginia, a hidden gem that perfectly blends suburban tranquility with vibrant community spirit. Nestled within the picturesque Chesapeake County, this charming city offers an inviting atmosphere, making it an ideal place for families, young professionals, and retirees alike.

South Chesapeake boasts a rich tapestry of parks, recreational facilities, and scenic waterways, providing residents with ample opportunities for outdoor adventures. Whether you prefer kayaking along the tranquil waters of the Elizabeth River or enjoying a leisurely stroll in one of the many lush parks, nature is always just a stone's throw away. The city is also home to excellent schools, shopping centers, and dining options, ensuring that all your daily needs are conveniently met.

For those seeking affordable housing options, South Chesapeake is a treasure trove of homes under $300,000. Here, you can find a diverse range of properties, from charming single-family homes to cozy townhouses, all designed to suit various lifestyles and budgets. These homes often feature spacious backyards, modern amenities, and welcoming interiors, making them perfect for both first-time buyers and those looking to downsize.

With its friendly neighborhoods and strong sense of community, South Chesapeake is not just a place to live; it's a place to thrive. Discover your dream home in this delightful city, where affordability meets quality living. Experience the warmth of South Chesapeake and make it your home today!

Newest South Chesapeake Homes under $300,000

$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 Chesapeake Regional Hospital. Home has all new LVP flooring and fresh paint. 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

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

1547 Orchard Grove Drive, South Chesapeake

$290,000

2 Beds ⋅ 2 Baths ⋅ 10654011 MLS

Welcome home to easy living in Orchard Grove! This spacious 2-bedroom, 2-bath condo offers a flexible layout designed for both everyday comfort and entertaining. Start your morning at the dedicated coffee bar before settling into the light-filled living room, where soaring ceilings and skylights create an open, airy feel. When the weather cools down, the gas fireplace makes the perfect spot to unwind. The updated kitchen features new cabinets, quartz countertops, stainless steel appliances, and plenty of space for preparing meals and gathering. Upstairs, the loft adds even more flexibility—create a home office, workout space, reading nook, hobby room, or explore modifications for an additional sleeping area. With two bedrooms and two full baths, there’s room to spread out while still enjoying the convenience of condo living. Orchard Grove puts shopping, dining, interstate access, military installations, and everyday conveniences nearby, making it easy to spend less time getting where you need to go and more time enjoying home.

1547 Orchard Grove Drive, South Chesapeake

$264,700

2 Beds ⋅ 1.1 Baths ⋅ 10653128 MLS

Location! Location! Ready to move in for someone who will really take care of the property. Brick front, end unit townhome, located in the heart of Greenbrier just minutes to shops, restaurants, mall (incl proposed Costco), banks, groceries, City Park, Sams club, I-64, Outlet mall, Naval bases, etc. Whether you are a 1st time buyer or downsizing, you will be spoiled with the conveniences around you. Good size bedrooms. New Roof, 2yrs old Washer & Dryer, Wood & Ceramic flooring, Double SS kitchen sink. Fenced in backyard with a storage shed. Great starter home!

923 Ketch Court, South Chesapeake

$283,999

2 Beds ⋅ 2.1 Baths ⋅ 10653079 MLS

Turnkey Luxury in Oakbrooke Crossing – Fully Updated & Pre-Inspected!Welcome to this beautifully updated 2-bedroom, 2.5-bathroom townhome-style condo in desirable Oakbrooke Crossing! This move-in-ready home features brand-new LVP flooring, fresh neutral paint, and an updated kitchen with laminate countertops, breakfast bar, and stainless steel appliances. Upstairs, you’ll find two spacious primary suites, each with its own private en-suite bathroom great for guests, roommates, or a home office. Enjoy added peace of mind with a brand-new water heater (2024), recently serviced HVAC, and a professional pre-inspection with the report available upon request.Conveniently located in the heart of Chesapeake, just minutes from Greenbrier shopping, dining, business centers, and interstate access. The low-maintenance condo lifestyle includes ground maintenance, trash service, and community upkeep. Ready for you! Schedule your showing today!

313 Holyoke Lane, 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.