South Chesapeake Homes with Grassfield High school

Welcome to South Chesapeake, Virginia—a vibrant community that perfectly blends suburban tranquility with urban convenience. Nestled in the heart of Chesapeake County, this charming area offers a welcoming atmosphere, ideal for families, young professionals, and retirees alike. With its picturesque landscapes, friendly neighborhoods, and a strong sense of community, South Chesapeake is an exceptional place to call home.

One of the standout features of South Chesapeake is its commitment to quality education, highlighted by the presence of Grassfield High School. Known for its dedicated staff and diverse programs, Grassfield High is a cornerstone of the community, providing students with a solid foundation for future success. Families seeking homes in this area can take comfort in knowing that their children have access to top-notch educational opportunities.

The real estate market in South Chesapeake is as diverse as its residents, featuring a wide range of homes that cater to various lifestyles and budgets. From charming single-family homes with spacious yards to modern townhouses, there’s something for everyone. Many properties boast beautiful landscaping, allowing residents to enjoy the lush greenery and outdoor spaces that define this area.

In addition to its residential appeal, South Chesapeake is conveniently located near shopping centers, parks, and recreational facilities, making it easy to enjoy a balanced lifestyle. Whether you’re exploring the local dining scene, taking a stroll in one of the nearby parks, or engaging in community events, South Chesapeake offers a rich tapestry of experiences.

Discover your dream home in South Chesapeake today, and embrace the perfect blend of comfort, community, and convenience!

Newest South Chesapeake Homes with Grassfield High school

$420,000

3 Beds ⋅ 2 Baths ⋅ 10656455 MLS

Tucked away on a quiet dead-end street, this beautifully updated 3-bedroom, 2-bath ranch offers peaceful water views and an inviting indoor-outdoor lifestyle. Enjoy an open, flexible floor plan, screened porch, oversized deck, and private fenced backyard great for relaxing, entertaining, kayaking, or simply enjoying the tranquil surroundings. Major updates include a NEW central HVAC system with new ductwork (2025), NEW kitchen appliances (2025), LVP flooring and fresh neutral paint.

668 Luther Street, Chesapeake

$480,000

4 Beds ⋅ 2.1 Baths ⋅ 10656500 MLS

Beautiful Colonial-style home situated on a spacious 0.41 acre corner lot w/ deep water access, dock and bulkhead. This large yet cozy home offers 4 bedrooms and 2.5 bathrooms w/ blends of classic charm and comfy living. Enjoy family evenings by the fireplace and take advantage of the expansive backyard-perfect for entertaining, outdoor activities, or future enhancements. The large corner lot provides added privacy and curb appeal, while the storage shed and attached garage offers lots of extra space for tools and lawn equipment. A rare opportunity to own water front property w/ room to spread out, both inside and out right in the heart of the city. Close to shopping yet private for your family needs.

824 Heritage Point, Chesapeake

$440,000

3 Beds ⋅ 2.1 Baths ⋅ 10654807 MLS

Welcome to 933 Centurion Circle where the ease of townhome living meets the comfort and style of a single-family home. This beautifully designed residence offers a spacious lower-level recreation room that opens to a private backyard—perfect for creating your own outdoor retreat—along with a 2-car garage for added convenience. The main level features an expansive gourmet kitchen with granite countertops, a large island, upgraded LVP flooring, and a bright, open living room that flows effortlessly onto an oversized Trex deck ideal for entertaining or unwinding. Upstairs, three generous bedrooms provide plenty of space, including a luxurious owner’s suite with a tray ceiling, walk-in closet, and spa-inspired bath with dual vanities and an oversized shower with a seat. Located in Grassfield’s best-valued community, you’ll enjoy resort-style amenities such as water views, a private marina club, pool, clubhouse, docks, boat tie-off, and beach access-all with no flood insurance required!

933 Centurion Circle, Chesapeake

$685,000

6 Beds ⋅ 3 Baths ⋅ 10655966 MLS

See this one first! Don’t miss this immaculate 6-bedroom, 3-full-bath home in the sought-after Forest Lakes community. Even better, the seller is offering a $20,000 credit for the buyer to use toward closing costs or a rate buy-down! This spacious, beautifully maintained home is packed with updates and features inside and out. Step inside to fresh paint throughout and beautifully refinished hardwood floors. The kitchen features newer stainless steel appliances, pull-out cabinet drawers, and a walk-in pantry. Custom closet built-ins provide excellent organization, while the large laundry room offers a sink, cabinetry, and plenty of additional storage. Need even more space? The huge walk-in attic provides an abundance of storage. Additional upgrades and features include HVAC systems replaced in 2020 and 2021, a whole-home purifier and diffuser connected to the HVAC system, a primary bathroom ceiling heater, surround-sound speakers in the living room, and an ultra-quiet garage door opener. Step outside to a huge fenced backyard situated on one of the largest lots in Forest Lakes, offering plenty of room to entertain, play, or simply relax. Enjoy the screened porch, newer composite decking, outdoor speakers, plant watering system, and storage shed. With 6 bedrooms, 3 full bathrooms, generous living space, extensive updates, an incredible backyard, and a $20,000 seller credit, this Forest Lakes home checks all the boxes. Schedule your private showing today!

817 Maple Forest Court, Chesapeake

317 George Washington Highway S, Chesapeake

$524,900

3 Beds ⋅ 2 Baths ⋅ 10655769 MLS

Five acres. A powered detached workshop. Room to breathe, space to make your own. This updated Cape Cod offers the flexibility of acreage living in Chesapeake’s Grassfield area. The home features 3 bedrooms, 2 full baths and a first-floor bedroom and full bath. MLS square footage reflects 1,869 sq. ft. per tax records; a recent appraisal measured approximately 2,067 sq. ft.Updates include a renovated kitchen and baths, replacement windows, updated electrical and plumbing, a 2023 heat pump, 2024 whole-house paint and newer flooring. Beautiful hardwood floors, a fireplace, and generous mud/laundry space add function and character. The approx. 736 sq. ft. powered detached garage/workshop offers room for tools, projects, and storage. Gorgeous outdoors boast a fenced yard area, wooded acreage, mature fruit and fig trees, enclosed porch, deck and patio. City water/sewer add convenience. Recent appraisal at $600,000! Existing VA loan may be assumable, reach out to listing agent for more details.

317 George Washington Highway S, Chesapeake

$575,000

4 Beds ⋅ 3 Baths ⋅ 10656015 MLS

Welcome to 423 Las Gaviotas Blvd., located in the desirable Las Gaviotas golf course community. Situated directly on the golf course, this 4-bedroom, 3-bath home offers approximately 2,585 square feet of living space and a spacious, versatile floor plan, with crown molding throughout. In-ground sprinkler system. Enjoy golf course views and the opportunity to personalize the home with your own finishes and style. Generous living areas provide plenty of space for everyday living and entertaining. Conveniently located in an established Chesapeake community, this property offers a wonderful combination of space, location, and possibilities. Motivated seller—schedule your private showing today!

423 Las Gaviotas Boulevard, 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, 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, Chesapeake

$684,824

4 Beds ⋅ 2.1 Baths ⋅ 10655903 MLS

Welcome to the popular Campbell model by Kirbor Homes, where thoughtfully designed spaces meet modern luxury. This home features a magnificent primary suite complete with a spacious walk-in closet, a spa-like ensuite featuring a freestanding tub, and a large bedroom designed for ultimate relaxation. The main level offers a dedicated home office, a cozy fireplace, and beautiful LVP flooring flowing throughout all main living areas. At the heart of the home, the extended kitchen provides ample counter space and storage, making entertaining effortless. Practical details like built-in mudroom cubbies keep daily life organized, while the rear covered porch offers the perfect outdoor retreat to unwind. Contact us today to learn more and explore options for your new home!

1011 Cedar Tree Court, Chesapeake

$225,000

10655901 MLS

Great opportunity to build on this .40 acre corner lot in the desirable Grassfield High School district! Conveniently located near Route 17 for an easy commute to Chesapeake, Portsmouth, Suffolk and surrounding areas. Property offers several existing improvements, including an in-ground pool with pumps and heater, greenhouse, chicken run with potential for alternate uses, Purple Martin houses, two 10" thick driveways designed to accommodate heavier vehicles, an existing septic system, underground Dominion Power conduit/lines, and an in-ground 500-gallon propane tank. Property and all existing improvements convey AS-IS. Bring your plans and make this property your own!

1028 Fox Trail, Chesapeake

$425,000

3 Beds ⋅ 2.1 Baths ⋅ 10655498 MLS

Welcome to your next home, where every day feels a little more special. Nestled in the highly sought-after Bryan's Cove community, this beautiful home offers more than just a place to live; it offers a lifestyle defined by comfort, convenience, and connection. Enjoy added privacy with a peaceful wooded backdrop and no rear neighbors. With a low condo fee, no flood insurance requirement, and zoning for the highly desirable Grassfield school district, this home truly checks all the boxes. Bryan's Cove is known for its scenic surroundings and exceptional amenities, offering the perfect blend of tranquility and everyday convenience. Residents enjoy access to a community dock, dog park, fitness center, clubhouse, and swimming pool. Nearby, you will find Publix, lots of other shopping and several restaurants, Tidewater Community College, and quick access to Interstates 64 and 264 makes commuting and daily errands effortless, while parks, recreation, and local attractions are all close by. Inside, you'll find a warm and inviting floor plan designed for both comfortable living and effortless entertaining. The spacious kitchen serves as the heart of the home, featuring a large center island with seating, abundant prep space, and a gas range that will delight home chefs. Every room has been thoughtfully designed to create a welcoming atmosphere where family and friends can gather and lasting memories can be made. Opportunities like this don't come along often. If you've been searching for a home in an exceptional community with outstanding amenities, top-rated schools, and a private, natural setting, this is one you won't want to miss. Schedule your private showing today and experience everything this remarkable home has to offer.

1741 Fortune Terrace, Chesapeake

$347,500

3 Beds ⋅ 1 Baths ⋅ 10655690 MLS

Own a piece of Chesapeake history! This charming Great Bridge Craftsman bungalow is documented by the Virginia DHR as Historic Resource #131-5027, dating to approx. 1915–1925. Full of warmth & character with beautiful wood floors, new LVP in the kitchen & laundry, fresh paint, updated fixtures, refreshed kitchen & bath, plus a versatile bonus room that can easily serve as an additional bedroom. Detached garage, spacious & a.36-acre lot. A rare blend of historic charm, modern touches & timeless character—ready to welcome you home!

944 Bells Mill Road, 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.