South Chesapeake Homes with Grassfield Elementary Elementary school

Welcome to South Chesapeake, Virginia, a hidden gem nestled in the heart of Chesapeake County. Known for its welcoming community and family-friendly atmosphere, South Chesapeake is a place where neighbors become friends and memories are made. With its picturesque landscapes and easy access to a variety of amenities, this vibrant city is perfect for those looking to settle down in a serene yet engaging environment.

One of the standout features of South Chesapeake is its commitment to education, particularly for families with young children. Homes in the area benefit from proximity to Grassfield Elementary School, a highly regarded institution that prides itself on nurturing young minds. With a focus on academic excellence and character development, Grassfield Elementary offers a supportive environment where children can thrive. Parents can have peace of mind knowing their kids are receiving a quality education just a stone’s throw away from home.

The residential neighborhoods in South Chesapeake boast a variety of charming homes, many of which feature spacious yards adorned with lush grass, perfect for outdoor play and family gatherings. The community is designed with families in mind, offering parks, recreational facilities, and walking trails that encourage an active lifestyle.

With its blend of excellent educational opportunities, friendly neighborhoods, and beautiful homes, South Chesapeake is an ideal place to call home. Come explore the warmth and charm of this wonderful city, where every day feels like a breath of fresh air. Your dream home awaits in South Chesapeake!

Newest South Chesapeake Homes with Grassfield Elementary Elementary school

$685,000

5 Beds ⋅ 2.1 Baths ⋅ 10652920 MLS

Welcome to a home where thoughtful design meets effortless comfort. Beautifully updated with brand-new LVP flooring, this inviting residence is enhanced by an impressive collection of custom upgrades. The primary suite features a California Closets custom system, while the office offers tailored shelving and storage. In the kitchen’s eat-in area, a dedicated dog station and additional pantry provide both style and everyday functionality. Step outside and discover a private backyard backing to peaceful woods, complete with a fire pit—for relaxing or entertaining under the stars. The screened-in porch offers another inviting space to unwind and enjoy your favorite show. With the neighborhood playground just across the street, this home blends privacy, convenience, and thoughtful details in all the right ways. A home this special deserves to be seen!

952 Checkerspot Way, South Chesapeake

$409,000

4 Beds ⋅ 2 Baths ⋅ 10653157 MLS

Renovated over the past few years, this beautifully kept brick ranch home is ready to welcome its next owners! Inside, the kitchen offers a fresh, modern feel with crisp white shaker cabinets, gleaming granite countertops, and newer stainless-steel appliances that make every day cooking a pleasure. Enjoy the charm of the hardwood floors, and other cozy features throughout this home as you add your own touch of decor! Before entering your backyard, enter into your fully screened and covered sunroom from your back door, enjoying the sounds and peace of your backyard. The adjoining fully enclosed sunroom provides a bright, inviting space for relaxing or entertaining, while the large backyard offers plenty of room for gatherings, play, or quiet evenings outdoors. Recent updates - including a newer installed roof and windows (2022), new front fencing (2025) newly remodeled bathroom showers (2024), and newly encapsulated crawl space by JES (2025), and for added peace of mind and long-term value with transferrable warranties! This charming home is truly move-in ready. Schedule your showing today!

2615 Cedar Road, South Chesapeake

$998,895

5 Beds ⋅ 3.1 Baths ⋅ 10652907 MLS

Experience luxury living in this one-of-a-kind Chesapeake retreat, nestled on a 3-acre lot in the Grassfield School District. This custom-built home blends modern comfort with timeless charm, offering an open-concept first floor design for today's lifestyle. The spacious family room flows seamlessly into the remodeled 2024 kitchen, with direct access to the back deck for everyday relaxation or entertaining guests. Choose between two generous primary suites. First floor primary suite features a gas fireplace, dual closets, and a sitting/office area. Second floor primary suite privately located above 3-car garage, offering separation from the additional upstairs bedrooms. Enjoy abundant space for hobbies and storage with two powered sheds, plus peace of mind from the new encapsulated crawl space with vapor barrier. Major upgrades, including the roof, HVAC, and kitchen in 2024, ensures comfort and efficiency for years to come. This exceptional property delivers a rare combination of privacy, space, and freedom with no HOA restrictions, making it a true Chesapeake gem.

1910 Hallmark Way, South Chesapeake

$650,000

5 Beds ⋅ 2.1 Baths ⋅ 10652716 MLS

Custom 5-bedroom, 2.5-bath Chesapeake home on a huge half-acre lot, currently zoned for Grassfield High School! This beautifully updated home features an open floor plan, pickled oak hardwood floors, quartz countertops, stainless steel appliances, gas range, custom barn doors, and European-inspired lighting and fixtures. The spacious primary suite offers cathedral ceilings, dual closets, and a private deck with peaceful wooded views. The spa-like primary bath features a freestanding soaking tub and custom porcelain-and-glass shower. Outside, enjoy an expansive deck and plenty of room for outdoor living, entertaining, and recreation. If you’ve been searching for a custom Chesapeake home with space, style, updates, and a large lot, this one deserves a closer look. Schedule your tour today!

2100 Millville Road, South Chesapeake

$989,900

4 Beds ⋅ 3.1 Baths ⋅ 10652733 MLS

Grace, Beauty, Functionality, Beautiful private location (acreage on a cul de sac) , only 10 lots on clear land bordered by mature trees as a backdrop. The primary opulent primary bath including an extra large closet and another large en suite are on the first floor along with a flex room. Our newest option is a "butlers kitchen" complete with full sink tucked just behind the well equipped main kitchen. Two additional large bedrooms upstairs. Covered rear porch with an amazing view! You couldn't ask for more. This semicustom building package is hard to beat! We have additional lots and plans available. This will be the last acreage neighborhood to be approved within the city. No main road lots here! If you are looking for new construction it a definite 'MUST SEE"! Ponds, wildflower field, private walking trail and more add up to an exceptional "positive vibe" . No upgrades needed, come see! Preferred lender incentives be sure to ask for details. We have 1 acre 3 acre and a 20 acre lot

4020 Tucker Lane, South Chesapeake

$499,900

4 Beds ⋅ 2.1 Baths ⋅ 10652556 MLS

Beautifully remodeled 4-bedroom, 2.5-bathroom home with water views in the sought-after Grassfield area of Chesapeake. This property offers the perfect blend of modern style and everyday comfort. Fresh paint, new flooring, new windows, and modern finishes throughout.Fully renovated bathrooms and an updated kitchen featuring granite countertops, stylish fixtures, and brand-new stainless steel appliances. A large patio door opens to a spacious backyard with a resort-like setting, featuring an inground pool and peaceful water views perfect for relaxing or entertaining.

509 Cassway Arch, South Chesapeake

$1,000,000

6 Beds ⋅ 3 Baths ⋅ 10652479 MLS

Open House Sat Sept 12 1-3pm. Modern Farmhouse Charm Meets Turnkey Living in Desirable Chesapeake! Discover the modern farmhouse you’ve been dreaming of, where peaceful country living meets thoughtful, top-to-bottom renovation. Set on serene acreage with panoramic wooded views. It embraces the natural surroundings. This beautifully refreshed home is ideal for extended family/multi generational living. Natural light fills the home, showcasing new flooring, fresh interior paint, updated lighting, and beautifully renovated bathrooms. The completely redesigned custom kitchen is the heart of the home, featuring quartz countertops, ceramic backsplash, abundant prep space, an inviting eat-in area and a KitchenAid appliance suite, ideal for everyday living and entertaining. The expansive living area offers plenty of room to gather, while the renovated wood-burning fireplace creates a cozy focal point with a new firebox, flue, chimney cap, and Buck Stove-style insert. Step onto the Trex deck with PVC railing and enjoy peaceful wooded views from the living space, primary suite or deck. The primary suite is a true retreat, featuring a custom-tiled shower with built-in bench and generous niche, deep soaking tub, double vanity and ceramic tile flooring. The expansive custom closet with built ins provides all the space you have been longing for. Additional improvements include an encapsulated crawlspace with dehumidifier, new septic system designed for 10 occupants, finished room over the garage with generous storage, updated downstairs ductwork, new interior and exterior doors and hardware, new lighting throughout, and a freshly graded crushed-aggregate driveway. The painted brick exterior adds a fresh, modern look while preserving brick’s timeless durability and character. Best of all, the home features a highly energy-efficient geothermal HVAC system. From the crawlspace to the exterior, virtually nothing has been overlooked. Renovated by New Again Houses VB. It offers the feel of quality new construction without sacrificing character, space or setting. See it today!

3132 Benefit Road, South Chesapeake

$629,000

4 Beds ⋅ 2.1 Baths ⋅ 10652508 MLS

Stunning, completely updated, and ready to impress! This house showcases like a model home with fresh paint, beautiful flooring, updated kitchen and baths, stylish lighting with dimmers, custom Closet Factory storage, new windows, new roof, and appliances less than 3 years old. The primary suite is a true retreat, featuring a closet to die for and a luxurious ensuite that feels like your own private spa. Step outside to your own private oasis on over half an acre, with an inground pool, Trex decking, gorgeous landscaping, and a brand-new fence. Just down the street from Grassfield schools and conveniently located near shopping, dining, and major interstates, making it easy to get anywhere you need to go. This home truly has it all—come see for yourself!

520 Leary Court, South Chesapeake

$549,900

4 Beds ⋅ 2.1 Baths ⋅ 10651217 MLS

Welcome to 2809 Cistern Circle! This beautifully maintained home offers spacious living areas, abundant natural light and a flexible floor plan for everyday living, entertaining and working from home. Dedicated space offers room for a home office, study, flex room or workspace. Smart Home Ready with Samsung SmartThings potential and compatible lighting, locks, cameras, thermostats, sensors and more. The living room features built-in surround sound, while the garage offers two additional 240V outlets. Enjoy a large fenced backyard, deck, patio and fire pit area. Community amenities include a pool, clubhouse, playground, picnic areas and green space. With a home office option, smart-home features, outdoor living, storage, flexible living space and neighborhood amenities, this move-in ready home is ready for its next owner!

2809 Cistern Circle, South Chesapeake

$430,000

3 Beds ⋅ 2.1 Baths ⋅ 10652100 MLS

Built in 2022, this beautiful townhome in Bryan’s Cove is truly move-in ready and offers a wonderful combination of space, comfort, and convenience. With three levels of living space, there’s plenty of room for everyone. The first floor includes a flexible bonus room that would make a great home office, workout room, playroom, or guest space, along with an attached two-car garage. The main level features an open floor plan with lots of natural light. The kitchen has granite countertops, stainless steel appliances, a large island, and plenty of space for cooking and gathering. The dining area opens to a private back porch, where you can sit and relax while enjoying the view of one of the community playgrounds directly behind the home. It’s especially nice to be able to keep an eye on the kids while they play. Upstairs, the spacious primary bedroom offers a tray ceiling, walk-in closet, and a double vanity in the primary bath. The additional bedrooms provide plenty of space for family, guests, or whatever fits your needs. Bryan’s Cove has so much to offer, with a clubhouse, fitness center, swimming pool, dog parks, playgrounds, pier, and docks. The location is also incredibly convenient to shopping, restaurants, military bases, and major interstates. If you’re looking for a newer, low-maintenance home with plenty of space, great amenities, and a backyard view that’s hard to beat, this is definitely worth seeing!

961 Gabion Way, South Chesapeake

$885,000

4 Beds ⋅ 3.1 Baths ⋅ 10651664 MLS

Enjoy peaceful country living on 3 beautiful acres, just 5 miles from all your city favorites. This immaculate light-filled 4-bedroom, 3.5-bath home offers 9ft ceilings, detailed crown molding, custom built-ins, a main-level primary suite with a full bath, plus a convenient first-floor laundry room and mudroom. The chef's kitchen features leathered granite countertops, custom tile backsplash, SS appliances, and a center island. Upstairs offers 3 additional bedrooms, a large loft, and a second primary suite with a full bath, standalone tub, dual vanity, and 2 large walk-in closets. Outdoors, enjoy a resort-style backyard with a fenced inground saltwater pool surrounded by stamped concrete and a gazebo. The property also features solar panels, 2 barns, raised garden beds, a playset, a fire pit, and an extended driveway with ample space for an RV or boat. A rare blend of privacy, upgrades, and convenience!

2517 Number Ten Lane, South Chesapeake

$437,000

3 Beds ⋅ 2 Baths ⋅ 10651301 MLS

Welcome to this meticulously maintained ranch, 3 bedroom 2 full bath, 2 car garage. Front formal living room/office, dining room, back living room/den with wood fireplace, large kitchen with breakfast eat in area. Home has New (May2026) LVP through out main living areas, walk in closest (custom layout) in primary bedroom, plenty of closest space in other bedrooms. The attached garage provides plenty space for cars, hobbies or a workshop. Many upgrades, windows, 2015-30 yr architectural shingle, 2022 dishwasher,2022 New HVAC/duct work all new heating & 14 SEER cooling system, 2024 hall bath remodeled. Too many items to list call for more info.

404 Creekwood Drive, South Chesapeake

Start Your Search

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.