South Chesapeake Homes with Crestwood Middle Middle school

Welcome to South Chesapeake, Virginia, a vibrant community that seamlessly blends suburban charm with urban convenience. Nestled within Chesapeake County, this delightful area is known for its friendly neighborhoods, lush green spaces, and an array of amenities that cater to families, professionals, and everyone in between.

One of the standout features of South Chesapeake is its proximity to Crestwood Middle School, a highly regarded institution that serves as a cornerstone for the community. Families residing in this area benefit from easy access to quality education, making it an ideal location for those prioritizing their children's academic success. Crestwood Middle School is celebrated for its dedicated staff, enriching programs, and a strong sense of community, ensuring that students receive not only a solid education but also a supportive environment in which to thrive.

The real estate landscape in South Chesapeake is diverse, offering a variety of homes that cater to different lifestyles and budgets. From charming single-family houses with spacious yards to modern townhomes, there’s something for everyone. Many homes are situated in family-friendly neighborhoods, providing a safe and welcoming atmosphere for residents.

In addition to its excellent schools, South Chesapeake boasts a host of recreational opportunities, including parks, walking trails, and local shops and dining options. With convenient access to major highways, residents enjoy easy commutes to nearby cities while still relishing the tranquility of suburban life.

Discover the warmth and community spirit of South Chesapeake, where quality living meets educational excellence at Crestwood Middle School. Your dream home awaits in this enchanting Virginia locale!

Newest South Chesapeake Homes with Crestwood Middle Middle school

$280,000

3 Beds ⋅ 1.1 Baths ⋅ 10653026 MLS

Welcome home to this well-maintained 3-bedroom, 1.5-bath townhome! All major systems have been replaced within the last 8 years, including the roof, offering valuable updates already taken care of. The home features a functional layout with comfortable living spaces and plenty of potential to make it your own. Best of all, there are NO HOA, giving you the benefits of townhome living without the added monthly expense. Whether you're a first-time homebuyer or simply looking for a place to call home, this property is ready for its next owner. Schedule your showing today!

1208 Basswood Court, South Chesapeake

$574,900

4 Beds ⋅ 2.1 Baths ⋅ 10653018 MLS

Located in Oak Bridge Forest, this 4-bedroom, 2.5-bath home offers a spacious layout, an oversized 2-car garage, and a large backyard made for enjoying the outdoors. Inside, a two-story foyer welcomes you into a light-filled floor plan featuring new laminate flooring, installed in 2025, throughout most of the home. The custom-designed kitchen received a complete makeover in 2025 and opens to the family room, creating an easy flow for everyday living and entertaining. Upstairs, the spacious primary suite features a private bath with a double vanity, walk-in shower, and jetted tub, with three additional bedrooms and a second full bath completing the level. Out back, mature landscaping and trees surround an in-ground pool with a new liner installed in 2024 and new pool heater added in 2025. A Trex deck provides additional space to relax or entertain. Additional features include a tankless water heater, sprinkler system, smart-home capabilities, Ring doorbell and exterior security cameras, plus an Invisible Fence encompassing the front and backyard. No HOA! With generous indoor and outdoor space, thoughtful updates, and a backyard ready for pool days and entertaining, this Oak Bridge Forest home has plenty to offer. Incentives may be available through preferred partners. Contact listing agent for details and eligibility.

733 Dissdale Lane, South Chesapeake

$410,000

3 Beds ⋅ 2 Baths ⋅ 10653003 MLS

Welcome to this well-maintained 3-bedroom, 2-bath ranch home in the gorgeous Riverwalk community! Proudly offered by its original owner, this charming one-story home offers 1,600 square feet of comfortable living with the convenience of a first-floor primary bedroom. The inviting layout provides plenty of space for everyday living, entertaining, or simply relaxing at home. Step outside to enjoy the back deck and create your own peaceful outdoor retreat. Riverwalk residents enjoy fantastic amenities including a clubhouse, swimming pool, playgrounds, tennis courts, scenic trails, and a boat ramp and dock with access to the Elizabeth River. Conveniently located to access bases, beaches, dining, entertainment, restaurants, shopping, and more. Well cared for and ready for its next chapter—come see all this wonderful home and community have to offer. Call now for your personal tour.

435 Supplejack Court, South Chesapeake

$337,000

3 Beds ⋅ 2 Baths ⋅ 10651901 MLS

Wake up to peaceful water views right from your bedroom! This spacious, well-maintained 3-bedroom, 2-bath condo offers 1,762 square feet per MLS of comfortable, single-level living and low-maintenance convenience. Featuring luxury vinyl plank flooring in the living areas. Large windows and a sliding glass door bring in plenty of natural light. The kitchen offers abundant cabinet space, newer stainless steel appliances, including a wine fridge, and a convenient pantry. The spacious primary suite features a walk-in closet, linen closet, and private bath with a double vanity, soaking tub, and separate stand-up shower. Additional features include newer windows and a sliding glass door, ceramic tile, carpeting, and plenty of storage throughout. Amenities include a pool and clubhouse. Association services also include dock maintenance, water, sewer, and trash.

5 Harbor Watch Drive Unit 405, South Chesapeake

$375,000

3 Beds ⋅ 2.1 Baths ⋅ 10652230 MLS

Surrounded by trees, this 2006 townhome-style condo offers a quieter setting with shopping, dining, parks & interstate access close by. The open main level features flexible living spaces anchored by a gas fireplace. The adjoining kitchen offers granite counters, stainless appliances, & an efficient layout open to the living areas. Upstairs are comfortably sized bedrooms, including a spacious primary suite w/ ensuite bath, double sinks, tiled shower & generous storage. Enjoy a shaded rear deck overlooking the wooded setting plus an oversized attached garage. Major updates include a high-efficiency York heat pump/HVAC installed 12/2025 (includes 10 yr parts/3 yr labor warranty) & architectural-shingle roof estimated at 2–5 years old. Pre-list inspection completed 9/2026; report available.

620 Estates Way Unit 120, South Chesapeake

$320,000

3 Beds ⋅ 2 Baths ⋅ 10652493 MLS

Waterfront living takes center stage in this inviting, third-floor condo in the heart of Great Bridge. Enjoy lovely views of the Intracoastal Waterway from your private balcony where you can relax and watch the boats pass by. Even better, the property includes a deep-water access boat slip - an exceptional feature for boating enthusiasts! Inside, this 3-bedroom home offers an open layout connecting the spacious kitchen, living room, and dining area. A wide hallway leads to the generous primary suite with a well-appointed bath and large walk-in closet with a custom closet organization system. Harbor Watch amenities include a pool and clubhouse, dock maintenance, water, sewer, trash, and a master insurance policy. Enjoy low-maintenance waterfront living with your boat just steps away!

7 Harbor Watch Drive Unit 221, South Chesapeake

$485,000

4 Beds ⋅ 2.1 Baths ⋅ 10652092 MLS

Gorgeous renovated 4-bedroom, 2.5-bath home in sought after Riverwalk perfectly situated on a cul-de-sac. Open floor plan filled with natural light and stylish upgrades throughout. Stunning kitchen with custom cabinets, butcher block countertops, stainless-steel appliances and amazing center island. The formal dining room and cozy living room with fireplace offer ideal spaces for entertaining or relaxing. The primary ensuite has vaulted ceiling, double sink vanity, stunning shower and walk in closet. Enjoy relaxing on the oversized back deck for a peaceful backyard retreat. Additional highlights include a generous walk-in attic, oversized 2-car garage, and excellent storage throughout. Residents enjoy access to amenities including a clubhouse, swimming pool, playground, tennis courts, scenic trails, and a boat ramp and dock on the Elizabeth River. Close to beaches, military bases, amazing restaurants, shopping and more. Fantastic home and vibrant community!

418 Supplejack Court, South Chesapeake

$345,000

2 Beds ⋅ 2 Baths ⋅ 10650907 MLS

Welcome home to this beautiful, like-new condo in the heart of Chesapeake! Built just 2 years ago, this home offers modern finishes, an open layout, and low-maintenance living.The open-concept floor plan connects the kitchen, dining, and living areas, creating a great space for everyday living or entertaining. The kitchen features quartz countertops, stainless steel appliances, upgraded cabinetry, and a large island with plenty of room for seating. LVP flooring, updated lighting, and plenty of natural light give the home a bright, welcoming feel throughout.The spacious primary suite offers a private retreat with a beautifully finished ensuite bath and generous closet space. Conveniently located near shopping, dining, and major interstates, you’ll have easy access to everything Chesapeake and Hampton Roads have to offer.Move-in ready, only 2 years old, and beautifully maintained—this is one you’ll want to see!

1509 Waitsel Drive Unit 206, South Chesapeake

$554,900

4 Beds ⋅ 3 Baths ⋅ 10651714 MLS

Beautiful craftsman style townhouse meticulously maintained and tastefully decorated. Open and bright with detailed moldings and wainscotting. Large Dining area opens to kitchen with granite counter tops and stainless steel appliances, oversized pantry with grand center island perfect for entertaining. Dining area and kitchen open to great room with cozy gas fireplace and built in bookshelves, engineered wood floors. First floor primary bedroom with newer flooring has en suite with newer shower and garden tub, dual sinks and large walk-in closet. First level also has an additional office with full bathroom that could be used as a 4th bedroom. Second level has bonus area great for TV/theatre room. Two additional bedrooms with access to a full bathroom. Relax in your screened in porch.

152 Tranquility Trace, South Chesapeake

$319,900

2 Beds ⋅ 2 Baths ⋅ 10651771 MLS

Welcome home to easy, low-maintenance living in this beautifully appointed 3rd-floor condo! Featuring an open-concept floor plan, soaring ceilings, and large windows that fill the space with natural light, this home offers comfortable one-level living with stylish interior finishes throughout. The spacious kitchen is designed for both everyday living and entertaining, with quartz countertops, stainless steel appliances, and a convenient breakfast bar. The owner's suite provides a relaxing retreat with an attached bath and walk-in closet featuring custom wood shelving. Outside, enjoy a peaceful pond with a short trail loop, plus a dedicated dog park in this pet-friendly community. Condo amenities include ground maintenance, sewer, trash pickup, and water for added convenience. Located just minutes from shopping and dining at Sam's Circle and offering an easy Battlefield commute, this home truly has everything you need for comfortable Chesapeake living!

1505 Waitsel Drive Unit 304, South Chesapeake

$449,000

4 Beds ⋅ 2.1 Baths ⋅ 10650928 MLS

Welcome to this beautifully maintained 4-bedroom home in one of Chesapeake’s most desirable areas! Ideally located just minutes from the highway, enjoy easy access to all the shopping, dining, and entertainment Greenbrier has to offer. Inside, you’ll find a thoughtfully updated interior, granite countertops, and modern finishes—Great for everyday living and entertaining. The spacious primary suite offers a true retreat. With generous living space, well-sized bedrooms, and upgrades in all the right places, this home is move-in ready. Enjoy the perfect blend of comfort, style, and convenience. Schedule your private showing today!

408 Kings Gate, South Chesapeake

$420,000

3 Beds ⋅ 2.1 Baths ⋅ 10650785 MLS

Well-maintained 3-bedroom (Loft could easily be converted to a 4th bedroom), 2.5-bath home featuring new flooring in the kitchen and bathrooms. Major updates completed in 2018 include the roof, HVAC system, range, microwave, and dishwasher. The functional floor plan offers comfortable living spaces, while the attached 2-car garage and driveway provide ample parking and storage. With key improvements already completed, this home is ready for its next owner to enjoy. Schedule your showing today!

1313 Duchess Of York Quay, 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.