South Chesapeake Homes under $500,000

Welcome to South Chesapeake, Virginia, a vibrant and welcoming community that perfectly blends suburban charm with urban convenience. Nestled in the heart of Chesapeake County, South Chesapeake offers residents a tranquil lifestyle while being just a stone's throw away from the bustling cities of Norfolk and Virginia Beach. With its picturesque parks, top-rated schools, and a variety of shopping and dining options, this area is ideal for families, young professionals, and retirees alike.

One of the most appealing aspects of South Chesapeake is its diverse real estate market, particularly for those seeking homes under $500,000. Here, you can find a delightful range of properties that cater to various tastes and preferences. From cozy single-family homes to modern townhouses, there's something to suit every lifestyle. Many of these homes feature spacious yards, updated interiors, and convenient access to local amenities, making it easy to enjoy the best of what South Chesapeake has to offer.

The community is rich in recreational opportunities, with numerous parks and outdoor spaces perfect for family outings, picnics, and leisurely strolls. Residents can also take advantage of the area's proximity to the stunning Chesapeake Bay, where boating, fishing, and water sports await.

Whether you're a first-time homebuyer or looking to downsize, South Chesapeake presents an incredible opportunity to invest in a thriving community without breaking the bank. Discover your dream home today and experience the charm and warmth of South Chesapeake living!

Newest South Chesapeake Homes under $500,000

1329 George Washington Highway N, South Chesapeake

$315,000

3 Beds ⋅ 2 Baths ⋅ 10657422 MLS

This 3-bedroom, 2-bath Chesapeake home sits on nearly half an acre with a large detached garage, ample parking, and an easy-access driveway. Inside, enjoy brand-new carpet, renovated bathrooms, and updated appliances. With plenty of room for vehicles, hobbies, storage, and outdoor living, this property offers space and flexibility that can be hard to find.

1329 George Washington Highway N, South Chesapeake

$365,000

2 Beds ⋅ 2.1 Baths ⋅ 10658068 MLS

Beautiful, well-maintained end-unit townhome in the Fairways neighborhood behind Greenbrier Country Club. Features include 2-bedroom, 2.5 baths, great room with fireplace and open floor plan with loft area that can be used for additional living space, office, playroom, etc. Spacious bedroom with master ensuite. Two-car garage and back patio for relaxing & entertaining with community-maintained lawns. Short drive to shopping, restaurants and access to interstate.

801 Shoal Creek Trail, South Chesapeake

$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

$385,000

4 Beds ⋅ 2.1 Baths ⋅ 10658236 MLS

Fully renovated and move-in ready ! This 4 bedrooms, 2.5 bathrooms offers 1932 sq ft. The first floor is an open plan with fresh paint inside & out, fresh LVP flooring & updated lighting. The open layout leads right into a fully upgraded kitchen with granite countertops, stainless steel appliances, and quality cabinetry. Upstairs, you'll find comfortable new carpeted bedrooms and bathrooms finished with modern update. Major updates include a brand-new HVAC system, new water heater, new roof, there's even more to appreciate in person. Come see it for yourself and make this little slice of resort-style living yours before it's gone!

809 Parapet Road, 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

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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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