South Chesapeake Homes under $500,000

Welcome to South Chesapeake, Virginia – a hidden gem nestled in the heart of Chesapeake County. Known for its charming neighborhoods, lush parks, and friendly community atmosphere, South Chesapeake is the perfect place to call home. This vibrant city offers a unique blend of suburban tranquility and urban convenience, making it ideal for families, young professionals, and retirees alike.

One of the most appealing aspects of South Chesapeake is its diverse range of homes available under $500,000. Whether you're searching for a cozy single-family residence, a modern townhouse, or a spacious split-level, you’ll find an array of options that cater to various lifestyles and preferences. With the current real estate market offering fantastic opportunities, now is the perfect time to explore what South Chesapeake has to offer.

In addition to affordable housing, South Chesapeake boasts a wealth of amenities that enhance the quality of life for its residents. Enjoy leisurely afternoons at one of the many local parks, take a stroll along the scenic waterways, or indulge in the vibrant dining scene featuring local favorites and international cuisine. Families will appreciate the top-rated schools and community programs that foster growth and development for children of all ages.

With its rich history, beautiful landscapes, and a strong sense of community, South Chesapeake is not just a place to live – it's a place to thrive. Discover your dream home today in this inviting city and experience all that South Chesapeake has to offer!

Newest South Chesapeake Homes under $500,000

$419,900

5 Beds ⋅ 2.1 Baths ⋅ 10658338 MLS

One of a Kind in Geneva Shores! Prepare to be surprised by just how much space this unique home has to offer! The owner added a custom-designed second floor, creating additional living space and flexible options to accommodate your needs through the years and generations to come. Full of character and nostalgic charm, this cozy home is tucked alongside a canal that leads to deep-water access on the Elizabeth River. Whether you dream of kayaking, cruising in your Jon boat, fishing close to home, or simply enjoying the peaceful waterfront surroundings, this property offers a wonderful opportunity to embrace life on the water. And there’s even more to love! Just one street away, you’ll find the Elizabeth River Park VDWR Boat Ramp, providing convenient access for your boating adventures. The home has central vacuum. A unique home, a waterfront setting, and endless possibilities! This is an estate sale....All of the furniture and accessories will be removed by November. Property is being sold AS IS HOME INSPECTION IS FOR INFORMATIONAL PURPOSES ONLY

2013 Athens Court, South Chesapeake

$449,900

3 Beds ⋅ 2.1 Baths ⋅ 10658185 MLS

Step into unparalleled luxury at 518 Silk Tree Lane, nestled in the quaint, village-like community of North Trail in the highly sought-after Greenbrier area. This 2,366 square-foot masterpiece is completely turn-key. Absolutely no upgrades are needed here. Every high-end detail has already been meticulously curated for you. The stunning gourmet kitchen is a true showstopper, featuring custom cabinetry and countertops, stainless steel appliances from the Frigidaire Professional Series - double wall ovens, a gas range, microwave, wine refrigerator, and built-in ice maker. Porcelain flooring flows throughout the living room, dining area, and kitchen, while well-maintained carpeting adds warmth and comfort to the upstairs and bedrooms. The commitment to high-end living extends into the bathrooms, which have been transformed into private, spa-like retreats featuring breathtaking custom walk-in showers with artisan tile work and built-in bench seating. A cleverly crafted bonus office space is perfectly situated just at the top right of the staircase, offering an ideal, quiet sanctuary for remote work. Storage abounds with custom built-ins and a walk-in attic. Enjoy the spacious custom paver patio with views of the serene community pond and fountains. Additional highlights include three-zone HVAC, Rinnai tankless water heater, custom trim and moldings, Bose surround sound, Cox security wiring, and an EV charging station. Embrace the ultimate low-maintenance lifestyle. The comprehensive condo fee covers all exterior grounds maintenance and trash pickup. Conveniently located in the heart of Chesapeake. Truly a must-see!

518 Silk Tree Lane, South Chesapeake

$459,900

4 Beds ⋅ 2 Baths ⋅ 10658238 MLS

Welcome to your waterfront Home! Nestled along a peaceful canal with deep water access, this beautifully updated 4-bedroom, 2-bath home offers the perfect blend of comfort & style. Inside, you'll find modern finishes throughout, including updated flooring and a kitchen equipped with granite countertops, stainless steel appliances, and ample cabinetry. The formal dining room features elegant custom-built cabinetry. The bathrooms have been tastefully remodeled with high-end finishes, creating spa-like retreats. Step outside to enjoy a large backyard overlooking the canal, perfect for relaxing, entertaining, or fishing. A garage, work shed, and generous outdoor space provide plenty of room for hobbies and storage.

216 Stubbs Drive, South Chesapeake

$474,900

4 Beds ⋅ 2.1 Baths ⋅ 10658133 MLS

Welcome to this beautiful, well-maintained 4-bedroom, 2.5-bathroom home featuring fantastic waterfront. The private backyard features a large deck and a screened-in pergola, perfect for relaxing and entertaining. Key features of the property include Solid wood floors and fresh interior paint throughout. Quality Mr. Rogers windows, Granite countertops and custom tile work in the bathrooms, including a jetted bathtub. Ceiling fans and wall-mounted TVs in every bedroom, option to purchase high-quality bedroom furniture at a discounted price. Back-up generator and well sprinkler system. This home is conveniently located near shopping, dining, and everything Chesapeake has to offer. let me know if you would like to schedule a viewing or if you have any questions.

416 Mishannock Way, South Chesapeake

$474,900

4 Beds ⋅ 2.1 Baths ⋅ 10657960 MLS

This beautiful property sits on a huge, fully fenced corner lot in a quiet neighborhood within the highly desirable Grassfield School District! This open and bright home features a spacious primary bedroom with multiple closets, separate dining room, a good-sized kitchen with a gas stove, and two beautifully updated bathrooms. Enjoy outdoor living on the large deck overlooking the expansive yard. The oversized room over the garage offers endless possibilities as a fourth bedroom, second family room, game room, or media room. Located in an amazing neighborhood, this home offers convenient access to shopping, major highways, and military bases. Space, comfort, and location make this home a must-see!

2630 Cecilia Terrace, South Chesapeake

1505 Waitsel Drive Unit 306, South Chesapeake

$310,000

2 Beds ⋅ 2 Baths ⋅ 10658216 MLS

Enjoy the perfect blend of comfort, style, and low-maintenance living in this inviting third-floor Chesapeake condo with no neighbors above! Soaring ceilings, abundant natural light, and an open layout with LVP flooring in the living area create a bright and airy atmosphere. The spacious kitchen features quartz countertops, stainless steel appliances, and a breakfast bar that flows effortlessly into the main living area, great for everyday living or entertaining. The primary suite offers a relaxing retreat with a private bath and generous walk-in closet featuring custom wood shelving. Beyond your front door, enjoy a peaceful community pond with a walking loop and dedicated dog park. With water, sewer, trash pickup, and grounds maintenance included in the condo fees, there's more time to enjoy the things you love! Conveniently located near shopping, dining, and major commuter routes, this home offers an easygoing Chesapeake lifestyle!

1505 Waitsel Drive Unit 306, South Chesapeake

$439,900

4 Beds ⋅ 2.1 Baths ⋅ 10658204 MLS

New Construction in Great Bridge high school district, near interstates, dining, shopping. Approx 30 days from completion, allowing for you to prepare Thanksgiving in your own brand new home this year! Builders reputation as quality builder has yielded spotless home inspections!

813 Mullen Road, South Chesapeake

$360,000

4 Beds ⋅ 2 Baths ⋅ 10658124 MLS

Well maintained ranch in Deep Creek is ready to welcome you home! Many updates & newer systems (2021 HVAC, 2023 water heater, Dec 2025 roof). Open flow from entry to dining to living room to kitchen. Updated granite countertops & cabinets, all stainless steel appliances, and bonus bar sink in kitchen. Primary opens directly to backyard/dog run for convenience with pups! Detached shed & workshop with electric provide plenty of space for hobbies & lawn equipment & toys. Fully fenced in backyard, with extra lot space outside of the fence. Some photos were virtually staged using AI.

1437 Glendale Avenue, South Chesapeake

$490,000

3 Beds ⋅ 2 Baths ⋅ 10657934 MLS

Well-kept all brick ranch in the heart of Great Bridge on a quiet cul-de-sac. Updated kitchen and bathrooms. 3 bedrooms, 2 baths downstairs and a FROG up. (FROG does not count as a bedroom. it does not have a door.) No carpet, hardwood and LVP throughout. Big back yard with a large patio! All appliances convey with home. Wood stove with blowers in den, recent chimney inspection. Window warranty transferrable. Generator hook-up. Newer storage shed. New poly in crawlspace. Clear letter from Chesapeake Pest Control. Roof 7 years new. No doors on some bedroom closets.

509 Dinwiddie Court, South Chesapeake

$355,000

4 Beds ⋅ 2 Baths ⋅ 10658131 MLS

Tucked away on a peaceful cul-de-sac, this charming Chesapeake property welcomes you with exceptional features and inviting style. Inside, the home boasts premium, eco-friendly bamboo flooring across most of the living areas, creating a clean, modern ambiance. A standout highlight is the unique two-section screened porch, carefully crafted for year-round enjoyment, morning coffees, or evening gatherings. The private backyard extends your living space with endless opportunities to relax, garden, or host loved ones. Situated moments from premier shopping, dining, and major commuter routes, this flexible home is ready for its next chapter.

700 Saxon Court, South Chesapeake

1125 Sir Gawaine Drive, South Chesapeake

$360,000

4 Beds ⋅ 2.1 Baths ⋅ 10658020 MLS

Welcome home to this charming Chesapeake property offering comfort, functionality, and space to grow. Enjoy peaceful mornings and quiet evenings from the charming covered porch, an ideal extension of the home's living space. This traditional home features a fenced backyard ideal for entertaining, pets, or play, along with a patio for relaxing evenings outdoors. Inside, you'll find thoughtful living spaces including a breakfast area, pantry, utility room, and a converted garage that provides flexibility for a home office, playroom, guest space, or hobby room. Located in an established neighborhood with easy access to shopping, dining, and major commuter routes. Don't miss your chance to make this Chesapeake home your own!

1125 Sir Gawaine Drive, South Chesapeake

$384,900

2 Beds ⋅ 2.1 Baths ⋅ 10657776 MLS

Welcome home to 604 Old Fields Arch, where classic brick curb appeal, mature landscaping and a flexible, light-filled floor plan come together in one of Chesapeake's most convenient settings. Step inside to a dramatic living room with soaring ceilings, oversized windows and a fireplace that anchors the space. The open layout flows easily from living to dining to kitchen, so it works just as well for quiet weeknights as it does for a house full of guests. The kitchen has generous cabinetry, plenty of prep space and a breakfast bar for casual meals. Upstairs, a spacious loft adds the bonus space today's buyers want. Use it as a second family room, home office, playroom, gym or media lounge. The primary suite is a true retreat, with a well-appointed bath featuring a double vanity, a separate shower and ample storage. The secondary bedrooms are comfortably sized with room to grow. Out back, a private patio is ready for grilling, outdoor dining or unwinding at the end of the day, and the low-maintenance exterior means more time enjoying your home and less time on upkeep. Bonus: with a full-price accepted offer, the buyer picks new countertops from three designer options: Giallo Ornamental granite, Steel Gray granite or Noble Pro Frost quartz. Minutes from shopping, dining and major commuter routes, 604 Old Fields Arch is ready for its next chapter. Schedule your private tour today.

604 Old Fields Arch, 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.

South Chesapeake Homes under $500,000

Newest South Chesapeake Homes under $500,000

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