South Chesapeake Homes with Crestwood Middle Middle school

Welcome to South Chesapeake, Virginia—a vibrant community where southern charm meets modern living. Nestled in Chesapeake County, this delightful area is known for its lush landscapes, friendly atmosphere, and a strong sense of community. South Chesapeake offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, professionals, and retirees alike.

One of the standout features of South Chesapeake is its access to quality education, particularly through Crestwood Middle School. Families seeking homes in this area will appreciate the school’s commitment to academic excellence and its nurturing environment. Crestwood Middle is renowned for its dedicated staff, diverse extracurricular activities, and a focus on fostering a love for learning, which makes it a top choice for parents.

The housing market in South Chesapeake is varied, offering everything from charming single-family homes to modern townhouses, catering to a range of lifestyles and budgets. Many homes boast spacious backyards, perfect for family gatherings and outdoor activities, while others feature contemporary designs with all the amenities you could desire.

Living in South Chesapeake means you’ll also enjoy easy access to parks, recreational facilities, and shopping centers, ensuring that you have everything you need right at your fingertips. With its friendly neighborhoods, excellent schools, and a wealth of local amenities, South Chesapeake is not just a place to live; it’s a place to thrive. Discover your dream home in this enchanting corner of Virginia today!

Newest South Chesapeake Homes with Crestwood Middle Middle school

$525,000

4 Beds ⋅ 2.1 Baths ⋅ 10656507 MLS

Welcome home to 1149 Crystalwood Circle! This inviting Chesapeake home has been thoughtfully cared for and updated over the years, offering the comfort of knowing many major improvements have already been completed. The electrical system was upgraded to 200-amp service in 2020, when the spacious 24' x 26' detached garage/workshop was added with its own 100-amp service. The HVAC received a new furnace and condenser in 2022, followed by a new washer and dryer in 2024 and a new water heater in 2025. In 2026, the home received a brand-new kitchen, new carpet, and a fully remediated crawl space with a new vapor barrier. With so much already done, there's more time to relax, enjoy your space, and make wonderful memories. Come see why this could be the one you've been waiting for!

1149 Crystalwood Circle, Chesapeake

$594,800

5 Beds ⋅ 2.1 Baths ⋅ 10656498 MLS

Spacious and beautifully updated, this 2-story Chesapeake home offers 5 bedrooms, 2.5 bathrooms, and a versatile loft perfect for a home office, playroom, or media space. Situated on a desirable corner lot, enjoy outdoor living on the composite deck and added peace of mind with a backup generator. Conveniently located near shopping, parks, military bases, and major interstates, this home combines comfort, functionality, and an unbeatable location.

513 Telfyan Drive, Chesapeake

$624,990

4 Beds ⋅ 2.1 Baths ⋅ 10656376 MLS

Seller is offering a $15,000 concession with a full price offer as Seller prefers to not do any additional improvements. This credit may be used at Buyers discretion towards closing costs, prepaids, fees and any buyer expenses or repairs. Stunning 4 bed 2 and a half bath custom-built home. Spacious bedrooms, upgraded kitchen with dual ovens and all newer appliances. Surround sound wired in the large family room. Newer flooring throughout. Custom built screened in back porch with a beautiful large yard. Relax on the front porch swing while overlooking the quiet cul de sac. Sought after neighborhood with the benefit of accessing major highways, bases & stores in minutes. Seller also providing a one year home warranty. Look at this one first! A beautiful place to come home!

1237 Spruce Lane, Chesapeake

713 Rapidan River Court Unit G, 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, Chesapeake

$705,000

4 Beds ⋅ 3 Baths ⋅ 10655182 MLS

Unique custom built home on cul-de-sac with rare 3 car attached garage and extended driveway. This house was made for entertaining - 23' x 14' screened porch off family room for extended living space, along with a 22' x 20' pavilion - both with trek decking, finished wood ceilings, recessed lights and fans. Beautiful extensive landscaping with a stamped concrete walkway winding around house. Impressive 2 story entry has gorgeous chandelier. Dual staircases. Large kitchen includes granite counters, stainless steel appliances with gas stove, tons of cabinets and counterspace as well as deep pantry and eat-in nook. Formal living room and dining room with door leading to large front porch. First floor office in addition to 4 bedrooms upstairs. Full bathroom downstairs. Hardwood floors run through entire 1st floor. Primary bedroom includes corner gas fireplace, 13'x12.5' walk-in closet, and large bathroom with dual sinks and jetted tub . Laundry room has entire wall of cabinets with counter space and fold down ironing board. Lots of built in storage throughout, including a walk in climate controlled attic closet. The rare 3 car garage (owner actually has 4 cars in there!) is decked out for a car aficionado with LED lighting covering the ceiling and rubberized flooring. Additional outside shed. 16 hardwired cameras around exterior convey. Generator hook up in garage. Top of the line outside Charbroil kitchen conveys with acceptable full price offer. Neighborhood dock with boat ramp nearby. Very active River Walk Community Association centers around the beautiful clubhouse (which can be rented) and has a tennis/pickleball court w/pickleball league, garden club, swimming pool w/swim team, concerts in fall, food trucks and more, as well as parks and playgrounds. Tree lined walking paths wind through neighborhood along lakes with gazebos and fountains. Easy to hop on nearby Rt. 168 Chesapeake Expressway to easily get to any area of Hampton Roads.

708 Pebble Quay, Chesapeake

$410,000

3 Beds ⋅ 2.1 Baths ⋅ 10654442 MLS

GREAT BRIDGE + HUGE BACKYARD + NO HOA! This beautifully maintained 3 bedroom, 2.5 bath home offers the space, features and location you've been looking for! Step inside to a bright, inviting interior filled with natural light and featuring updated flooring, granite countertops and a wood-burning fireplace, just right for cozy evenings. Upstairs, you'll find a spacious primary suite, along with two additional bedrooms. Step outside and discover one of this homes' standout features - a HUGE, fully fenced backyard with plenty of room to entertain, play, garden or simply relax on the patio. The 2-car garage provides additional parking and storage. Conveniently located near shopping, dining, parks and major roadways. Well maintained, move-in ready and NO HOA! Solar panels are paid for! Schedule your showing and come see what makes this Great Bridge home a must-see!

828 Helmsdale Way, 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, Chesapeake

$425,000

4 Beds ⋅ 2.1 Baths ⋅ 10654335 MLS

Discover timeless charm in this beautiful, traditional home located in the heart of Chesapeake. Featuring 4 bedrooms, 2.5 bathrooms, and a spacious two-story layout, this home includes a bedroom with its own en suite bath, making it great for guests or added privacy. Gather around the cozy fireplace on cool evenings, or enjoy casual meals in the bright breakfast area. Step outside to a fully fenced backyard, great for entertaining, pets, or relaxing outdoors. Recent upgrades, including new siding and roof (2021) and a remodeled primary bathroom (2025), enhance both the home's beauty and value. An attached garage and attic complete this exceptional property. Don't miss your opportunity to make this Chesapeake gem your own!

744 Helmsdale Way, Chesapeake

$480,000

4 Beds ⋅ 2.1 Baths ⋅ 10654173 MLS

Welcome to this beautiful one-owner ranch-style home featuring FIVE bedrooms, 2 1/2 baths and a 2-car garage. Situated on a cul de sac and in a neighborhood where homes rarely come on the market, this home is a real find! Enter via the spacious foyer, flanked by formal living and dining rooms, each boasting tray ceilings. Continue in and cozy up by a centrally-featured fireplace in the huge, open family rm, w/ full view of kitchen & large breakfast area. Brand new stainless steel appliances & new flooring are highlights of the kitchen, and brand new carpet runs through the entire downstairs. The en-suite primary lies on one side of the home with three bedrooms and full bath located on the other side. The room over the garage serves as the 5th bedroom. Entire home has been professionally painted & cleaned. Notes: new roof in 2020, extra replacement windows in storage, tons of garage cabinets, shed. Washer, dryer, well/pump work but convey AS IS. Location is so convenient to everything!

717 Treetop Lane, 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, Chesapeake

$385,000

3 Beds ⋅ 2.1 Baths ⋅ 10653788 MLS

Welcome home to this stunning 3-bedroom, 2.5-bathroom gem nestled in one of Chesapeake's most serene and desirable neighborhoods. The main level boasts a bright and cozy living room that flows seamlessly into a stylish kitchen, making everyday living and entertaining a breeze. Upstairs, you will find spacious, private bedrooms and well-appointed bathrooms. Outside is a generous backyard that serves as your own private oasis, perfect for hosting weekend gatherings, gardening, or relaxing in the sun. Situated in a peaceful community just minutes from local shopping, dining, schools, and major commuter routes, this home truly has it all. Don't miss the opportunity to make this house your home sweet home! Schedule your private tour today! Listing photos contain virtually staged media.

601 Lord Byron Court, Chesapeake

$409,000

3 Beds ⋅ 2.1 Baths ⋅ 10654072 MLS

Welcome to this spacious 3-bedroom, 2.5-bath split-level condo in a great Chesapeake location near Oak Grove Park, the hospital, shopping, and interstate access. The mid-level foyer leads to the lower level, featuring a comfortable sitting room with a fireplace, access to the back deck and fenced backyard, a utility closet, two bedrooms with large closets, full hall bathroom, and access to the attached 2-car garage with a convenient garage door opener. Upstairs, the updated kitchen offers stainless steel appliances, a pantry, bar, and breakfast area with bench seating, along with a fireplace and built-in storage. The upper-level living room provides additional space for relaxing or entertaining. The spacious primary suite features a walk-in closet and ensuite bathroom with a granite vanity, built-in makeup table, jetted tub, separate shower, and water closet.

415 Prince Phillip Court, 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.