South Chesapeake Homes with Grassfield High school

Welcome to South Chesapeake, Virginia, a vibrant community nestled within the picturesque Chesapeake County. Known for its friendly atmosphere and strong sense of community, South Chesapeake offers a perfect blend of suburban tranquility and urban convenience. With lush parks, scenic trails, and a variety of local shops and restaurants, this charming area is ideal for families, young professionals, and retirees alike.

One of the standout features of South Chesapeake is its commitment to quality education, with Grassfield High School serving as a cornerstone for the community. Renowned for its academic excellence and diverse extracurricular programs, Grassfield High School is a source of pride for residents. Families seeking homes in this area will find a welcoming environment that prioritizes education and personal growth for students of all ages.

The real estate market in South Chesapeake boasts a variety of options to suit different lifestyles and budgets. From contemporary single-family homes to charming townhouses, there’s something for everyone. Many properties feature spacious yards, perfect for outdoor gatherings, gardening, or simply enjoying the beautiful Virginia weather. The community’s commitment to maintaining green spaces and parks further enhances the appeal of living in this area.

Whether you’re drawn to the top-rated schools, the friendly neighborhood vibe, or the abundance of recreational opportunities, South Chesapeake is a place where you can truly feel at home. Discover the perfect property near Grassfield High School and experience the charm and convenience of South Chesapeake, Virginia!

Newest South Chesapeake Homes with Grassfield High school

$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

$525,000

4 Beds ⋅ 2.1 Baths ⋅ 10652912 MLS

A rare opportunity in one of Chesapeake’s most desirable neighborhoods!! Exceptional 4-bedroom, 2.1-bath home perfectly positioned on a corner lot overlooking the fairway in highly sought-after Las Gaviotas & the Grassfield school district. The first floor offers two generous living areas, a formal dining room, and an updated kitchen featuring granite countertops, tile backsplash, gas range, and ample cabinetry. Large windows frame peaceful views of the golf course, creating a bright, inviting atmosphere throughout. Four spacious bedrooms with the primary including a walk-in closet & a beautifully finished primary ensuite bathroom with a soaker tub, separate shower, and double-sink vanity. Step outside to enjoy composite decking & a backyard that opens directly to the fairway—an ideal setting for morning coffee, evening unwinding, or hosting friends. Just minutes from top-rated schools, shopping & dining, this home blends convenience with the charm & prestige of golf-course living.

400 Las Gaviotas Boulevard, 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

$109,000

10652636 MLS

Uncover extraordinary potential in Chesapeake’s highly desirable Hillcrest area! This rare, untapped residential acreage presents a lucrative opportunity for builders, savvy investors, or future homeowners seeking to build a custom private retreat or multi-lot project. Nestled in a quiet, established neighborhood, you'll love the perfect balance of peaceful living and quick access to top-rated schools, local shopping, and major highways. The subject property is to be sold jointly with 3 other adjacent parcels. Four prime parcels at this price point offer unbeatable equity in a growing market. Don't miss this high-value Chesapeake investment—bring your vision to this property today!

0.229 Trinkle Street, 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

$749,000

5 Beds ⋅ 2.1 Baths ⋅ 10652400 MLS

Welcome to this spacious 5-bedroom home set on nearly half an acre in the Grassfield school district! Designed for comfortable everyday living and effortless entertaining, the light-filled layout features soaring ceilings and generous living spaces. Kitchen showcases granite countertops, abundant cabinetry, and stainless steel appliances, opening naturally to the main living areas. A first-floor bedroom offers flexibility for guests, a home office, or playroom. Upstairs, the expansive primary suite features a sitting area with fireplace, oversized walk-in closet, dual vanities, soaking tub, and tiled walk-in shower. Outside, enjoy a large deck, hot tub, and fully fenced backyard with plenty of room to gather, play, and unwind. An above-ground pool is currently in place for buyers who would like it, with removal also an option. Oversized two-car garage, ample driveway parking, and convenient access to shopping, dining, and major roadways complete this exceptional Chesapeake home.

905 Washington Drive, 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

$619,000

4 Beds ⋅ 2.1 Baths ⋅ 10652285 MLS

Fantastic location close to shopping, major hwys primary and secondary schools and so much more! The already large/oversized primary suite has a large additional private flex room for office or nursery, workout room or whatever your heart desires. Complete with private bath and large walk in closet. For additional privacy the ancillary bedrooms are on the opposite side of the home. This home is a one owner former model home. New carpet just for you! The neighborhood is low turnover, well established and quiet. Beautiful foyer and open hall say "elegance" while having "cozy home" feel. 2 large sheds so you can park both cars in the garage. Smartly laid out with oversized rooms thru out. Separate zone HVAC for large sunroom with tile flooring. updated kitchen with abundant cabinets!

228 Country Club Boulevard, South Chesapeake

$417,500

3 Beds ⋅ 2.1 Baths ⋅ 10652096 MLS

Built in 2023 and meticulously maintained, this 3-bedroom, 2.5-bath end-unit townhome offers 1,790 square feet of comfortable, low-maintenance living in Cardinal Meadows. The first floor features durable LVP flooring and a well-appointed kitchen with a gas range. Step outside to a fenced rear patio, made for relaxing or entertaining. The finished garage stands out with epoxy flooring and custom storage for a clean, organized workspace. Located in Chesapeake’s sought-after Grassfield/Great Bridge area near Cedar Road and Cahoon Parkway, the community offers walking trails, a playground, covered pavilion, splash pad, and dog park—all within a top-rated school district.

1621 Songbird Lane, 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.