South Chesapeake Homes under $500,000

Welcome to South Chesapeake, Virginia – a hidden gem nestled in the heart of Chesapeake County. This vibrant community boasts a perfect blend of suburban tranquility and urban convenience, making it an ideal destination for families, professionals, and retirees alike. With its lush parks, scenic waterways, and friendly neighborhoods, South Chesapeake offers a welcoming atmosphere that feels like home from the moment you arrive.

One of the most appealing aspects of South Chesapeake is the diverse range of housing options available, particularly for those seeking homes under $500,000. Here, you’ll discover charming single-family homes, modern townhouses, and well-maintained condos, all designed to cater to a variety of lifestyles and budgets. Whether you’re a first-time homebuyer looking to plant your roots or a savvy investor searching for a rental property, South Chesapeake has something for everyone.

The area is renowned for its excellent schools, making it a popular choice for families. Additionally, residents enjoy easy access to shopping, dining, and recreational activities, with nearby parks offering trails, playgrounds, and picnic areas. For those who love the outdoors, the nearby Elizabeth River and numerous waterways provide ample opportunities for boating, fishing, and enjoying nature.

With its affordable housing market and rich community spirit, South Chesapeake is not just a place to live, but a place to thrive. Explore the possibilities today and discover your dream home in this charming Virginia city!

Newest South Chesapeake Homes under $500,000

$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

$459,900

4 Beds ⋅ 2 Baths ⋅ 10656377 MLS

Welcome to this spacious 4-bed, 2-bath home situated on a beautiful half-acre lot in the heart of Great Bridge! Offering a flexible floor plan, this home features 2 oversized living areas, 2 spacious primary bedrooms, & 2 additional bedrooms—ideal for multigenerational living, a home office, playroom, or the potential for a 5th bedroom. Updates include fresh interior paint, new flooring, restored hardwood floors, & renovated bathrooms. The updated kitchen offers new countertops, ample cabinet space, & a cozy breakfast nook. Step outside to the covered deck overlooking the expansive backyard, providing plenty of room for entertainment, gardening, pets, or future outdoor additions. With no HOA, you’ll also enjoy plenty of space to park your RV or boat on the property. Located in the highly desirable Great Bridge school district, you’ll enjoy the convenience of being just minutes from shopping, restaurants, & everyday amenities. Don’t miss this rare opportunity to own a move-in-ready home with space, flexibility, & an unbeatable location. Schedule your showing today!

145 Hurdle Drive, South Chesapeake

$479,972

3 Beds ⋅ 2.1 Baths ⋅ 10656369 MLS

Move right in to this beautifully maintained home, built in 2016 and perfectly situated on over ¾ of an acre at the end of a quiet cul-de-sac. Designed with both comfort and entertaining in mind, this home features 9-foot ceilings, an open-concept floor plan, quartz countertops, and stainless steel appliances. Upstairs, you’ll find a convenient laundry room with washer and dryer that convey. The expansive backyard offers endless possibilities, with plenty of room to add a pool, garden, or outdoor living space—all enhanced by attractive fencing.Enjoy a tucked-away, private setting while still being just minutes from shopping, interstates, and military bases. This home truly offers the best of space, style, and location. Attractive financing using the Seller's preferred lender . Be sure to inquire.

1121 Kinderly Lane, South Chesapeake

729 Mount Pleasant Road, South Chesapeake

$465,000

3 Beds ⋅ 2 Baths ⋅ 10656198 MLS

Step into this beautifully maintained ranch-style home that blends comfort, convenience, and charm. Featuring updated bathrooms and a modern kitchen with stylish finishes, this home is ready for you to move right in. Enjoy the spacious large open yard perfect for gatherings, gardening, or simply relaxing surrounded by a newer upgraded wooden privacy fence for peace and seclusion. The screened-in porch offers a cozy spot to unwind year-round, while those who work from home or need a creative space, there is an outdoor office with electric and AC to ensure comfort and productivity. Schedule your showing today.

729 Mount Pleasant Road, South Chesapeake

$415,000

3 Beds ⋅ 2.1 Baths ⋅ 10656271 MLS

This move-in-ready, 3-bedroom, 2.5-bath features recently installed carpet throughout, and a new dishwasher. The open-concept layout flows between the kitchen, dining, and living areas, creating a space for daily living and entertaining. Generously sized rooms offer flexibility for furniture placement, while deep closets and storage help with organization. The kitchen features soft-close drawers, granite countertops, a custom backsplash, and an island with accent lighting. Upstairs, the primary suite offers a walk-in closet, double vanities, and a walk-in shower with dual shower heads. The hall bath also features double vanities and direct access from the second bedroom. The attached garage and fenced backyard patio provide an ease with daily living. Enjoy local shopping and dining along with outdoor recreation at Great Bridge Lock Park along the Intracoastal Waterway. Nearby commuter routes connect you to military bases and destinations throughout the area.

308 Sikeston Lane, South Chesapeake

$489,900

4 Beds ⋅ 2 Baths ⋅ 10656242 MLS

Charming ranch with large backyard and pool! Enjoy the welcoming front porch before heading inside to the thoughtfully updated interior, where fresh paint and beautiful new LVP flooring create a bright, inviting atmosphere. New carpet in the room above the garage adds comfort and versatility to the home's flexible living space. Designed for both everyday living and effortless entertaining, the home features a living room, dining room, and a cozy family room accented by wood beams and a fireplace. At the heart of the home, the eat-in kitchen offers all new sleek cabinetry, granite countertops, and stainless steel appliances. Four spacious bedrooms provide comfortable accommodations, while both full bathrooms have been refreshed with stylish new vanities. Outside, you're sure to enjoy the fully fenced backyard featuring a spacious deck overlooking the swimming pool creating an inviting setting for relaxing, entertaining, or enjoying warm summer days. Two storage sheds provide additional room for lawn equipment, tools, or hobbies, while the attached garage adds everyday convenience and extra storage.

403 Caravelle Court N, 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

1005 Winged Foot Court Unit B, South Chesapeake

$335,000

3 Beds ⋅ 2.1 Baths ⋅ 10656159 MLS

Welcome Home to this charming twin Home style Condo in Greenbrier's Fairways Villas. Tucked away in the cul-de-sac with garage, driveway, and communal parking, low maintenance living meets style and convenience. Enter into your inviting foyer greeted with LVP floors and neutral paint. Layout features large open concept great room and dining area. Eat-in kitchen is spacious with granite tops and stainless appliances. Access to one car garage and laundry off kitchen and half bath for the ultimate first floor layout. Second level features large primary bedroom with ensuite bath and walk in closet. Bedroom features natural light and vaulted ceilings. Two large spare bedrooms and hall bathroom complete this ideal layout. Large slider leads to rear deck which is large and tranquil backing up to golf course views. Newer HVAC & water heater 2021 and replacement windows. Call this Home Today!

1005 Winged Foot Court Unit B, South Chesapeake

$450,000

3 Beds ⋅ 2.1 Baths ⋅ 10655125 MLS

Imagine coming home to a peaceful cul-de-sac tucked away just minutes from everything Greenbrier has to offer. The nearby city park is wonderful for a quick bike ride or leisurely stroll, while restaurants, shopping, and entertainment at Summit Pointe are just minutes away.This home offers the best of both worlds... the privacy and peacefulness of your own backyard while keeping you close to the places you want to go and the things you love to do. Enjoy the feeling of a quiet retreat without giving up convenience or connection.Don't miss your opportunity to make this move in ready Greenbrier gem your next home. Schedule your showing today!

621 Windward Drive, South Chesapeake

$499,999

3 Beds ⋅ 3 Baths ⋅ 10656063 MLS

Welcome home to Chesapeake’s premier 55+ community! This move-in-ready home offers a fantastic and flexible floor plan featuring TWO spacious primary suites—one on each level—providing plenty of room for guests. The beautiful family room features soaring vaulted ceilings, luxury vinyl plank flooring, and a cozy gas fireplace. Just off the main living area is an additional first-floor flex space, perfect for a home office, reading room, or a relaxing spot to enjoy your morning coffee. The spacious eat-in kitchen features new stainless steel appliances and recessed lighting, while the formal dining room provides the perfect space for entertaining. The large first-floor primary suite offers a private bath with double vanity, separate shower, and oversized jetted tub. At the heart of the community is the Bay Club, featuring indoor and outdoor pools, hot tub, fitness center, billiards, library, game rooms, and so much more. Come experience resort-style living at Eagle Pointe!

1407 Hawick Terrace, South Chesapeake

$429,900

3 Beds ⋅ 2 Baths ⋅ 10655782 MLS

Welcome to 109 Causeway Dr, a charming home nestled on a quiet street in the highly desirable Great Bridge area of Chesapeake! Enjoy major peace of mind with recent big-ticket upgrades, including a newly updated HVAC system, new water heaters, flooring throughout, and the electrical panel in the garage updated within the last 2 years. One of the standout features of this property is the HUGE backyard—providing an abundance of open space for entertaining, gardening, or play. Plus, there is ample parking and side access with more than enough space to park your large RV, boat, trailer, or multiple vehicles. Location is everything! Situated just off Battlefield Blvd, you are minutes away from top-rated Chesapeake public schools, local parks, waterways, and the Intracoastal Waterway. You'll love the convenience of quick access to everyday shopping, dining, medical facilities, and major highways for an easy commute throughout Hampton Roads.

109 Causeway Drive, South Chesapeake

$475,000

4 Beds ⋅ 2 Baths ⋅ 10655999 MLS

Escape to your own private waterfront retreat on nearly 1/2 acre in the sought-after Inland Colony community, where peaceful wooded surroundings and serene water views create the perfect connection to nature. This 2,494 sq. ft. home offers 4 bedrooms, 2 baths, a first-floor primary suite, detached ADU, 1-car garage, and private dock with access to the Intracoastal Waterway on the Elizabeth River. Enjoy the expansive deck overlooking the backyard and water or unwind on the screened porch off the primary suite. Fresh paint and new carpet enhance the bedrooms, while the spacious kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and generous prep space. French doors open from the dining room to the living area, creating an ideal layout for entertaining. The FROG with new carpet and large walk-in attic provide excellent flexibility and storage. Some photos may be virtually staged. Conveniently located near shopping, dining, top-rated schools, and interstate access while offering a true waterfront escape.

1145 Sunlight Drive, South Chesapeake

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