South Chesapeake Homes with Grassfield Elementary Elementary school

Welcome to South Chesapeake, Virginia—a vibrant community that beautifully blends suburban charm with the conveniences of modern living. Nestled within the larger Chesapeake area, South Chesapeake offers residents a warm, welcoming atmosphere, characterized by tree-lined streets, friendly neighbors, and a strong sense of community. With easy access to major highways, residents can enjoy a quick commute to nearby cities while still relishing the tranquility of suburban life.

One of the standout features of South Chesapeake is its commitment to quality education, particularly with homes located near Grassfield Elementary School. Families seeking a nurturing environment for their children will appreciate the excellent educational opportunities that this school provides. Grassfield Elementary is known for its dedicated staff, innovative teaching methods, and a strong emphasis on fostering a love for learning. The school’s vibrant community involvement ensures that children not only excel academically but also develop valuable social skills through various extracurricular activities.

The homes in South Chesapeake are as diverse as its residents, offering a range of styles and sizes to fit every lifestyle. From charming single-family homes with spacious backyards to modern townhouses, there’s something for everyone. Many properties feature lush green lawns, perfect for family gatherings, outdoor play, or simply enjoying the serene Virginia weather.

In South Chesapeake, you’re not just buying a home; you’re investing in a lifestyle that prioritizes family, education, and community. Explore the possibilities of making South Chesapeake your next home, and experience the perfect blend of comfort, convenience, and charm.

Newest South Chesapeake Homes with Grassfield Elementary Elementary school

$660,000

5 Beds ⋅ 2.1 Baths ⋅ 10647099 MLS

Welcome to 2317 Angler Lane, a well-maintained home in a sought-after Chesapeake area with convenient access to shopping, dining, and major roadways. Recent updates include new vinyl front stairs (2026), an extended driveway (2024), vinyl fencing (2024), pool house (2022), water heater (2020), roof (2019), and HVAC systems (2018). The outdoor setup is a standout with a screened-in porch, in-ground pool, and approximately 250 sq. ft. detached pool house with heating and air conditioning and a full bathroom. Speakers are located in both the living room and pool house. With plenty of space to relax, entertain, and enjoy the backyard, this home offers a hard-to-find combination of indoor and outdoor living. Make sure to check out the virtual tour.

2317 Angler Lane, Chesapeake

$634,900

4 Beds ⋅ 3.1 Baths ⋅ 10646890 MLS

Beautifully maintained 4 Br 3.5 bath home on 1/2 acre lot located in the Grassfield area of Chesapeake. 2 large primary suites 1 upstairs and 1 downstairs. 2 additional bedrooms upstairs that share a Jack n Jill. Theater room located downstairs that you will absolutely love. Some other upgrades include gourmet kitchen, granite countertops, stainless steel appliances, hard wood/LVP flooring, full privacy fence and beautifully maintained landscaping. The roof was replaced 2018.

2308 Angler Lane, Chesapeake

$430,000

3 Beds ⋅ 2.2 Baths ⋅ 10646321 MLS

Built in 2022, this move-in-ready end-unit townhome in the sought-after Bryan's Cove community offers the perfect blend of modern design, comfort, and convenience. This three-story home features a flexible first-floor bonus room ideal for a home office, gym, or guest suite, plus an attached two-car garage. The open-concept main level is filled with natural light and showcases a gourmet kitchen with granite countertops, stainless steel appliances, a large center island, and an adjoining dining area with access to a private balcony—perfect for relaxing or entertaining. Upstairs, the spacious primary suite features a tray ceiling, walk-in closet, dual vanities, a soaking tub, and separate shower. Enjoy resort-style amenities including a clubhouse, fitness center, swimming pool, dog parks, playgrounds, pier, and docks. Conveniently located near shopping, dining, military bases, and major interstates, this low-maintenance townhome offers exceptional value and an unbeatable lifestyle.

1732 Defiance Drive, Chesapeake

$734,900

5 Beds ⋅ 3 Baths ⋅ 10646525 MLS

There is not enough space to explain how wonderful this home is! A rare sense of privacy meets thoughtful luxury in this upgraded 2022 Grassfield home. Near the end of a cul-de-sac and bordered by protected wetlands and unbuildable parcels on both sides, the lot offers a wooded backdrop that is hard to replicate. The flexible 5-bedroom, 3-bath layout includes two primary suites, one on the first floor, PLUS an office/flex room AND loft-style second living area. Crown molding, hardwood stairs, custom window treatments, a gas fireplace, quartz countertops, stainless appliances, gas cooking, under-cabinet lighting, upstairs laundry, walk-in attic, tankless water heater, smart garage opener, security system, and a custom 36-foot patio add comfort and refinement. Trusted lender Steve Hawley, NMLS #1813927, with Southern Trust Mortgage, NMLS #2921, will provide a 1% lender-paid buydown on this listing. Ask the listing agent for details. Subject to borrower qualification and lender approval.

1741 Watershed Court, Chesapeake

$435,000

3 Beds ⋅ 2.1 Baths ⋅ 10646107 MLS

The 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

$849,900

5 Beds ⋅ 4.1 Baths ⋅ 10646141 MLS

Under Construction – Luxury New Construction with Timeless Coastal Farmhouse Style! This stunning 3-level home blends classic board-and-batten architecture, clean lines, black-framed windows, and thougthful accents to create exceptional appeal. Inside, an open-concept first floor is designed for modern living, featuring a spacious family room, dining area, and a designer kitchen with a large center island, custom cabinetry, and premium finishes. The second level offers four generously sized bedrooms, including an impressive owner's suite with a spa-inspired bath, plus two full bathrooms to comfortably accommodate family and guests. The third floor provides incredible flexibility with a spacious bonus room or fifth bedroom, a full bath, and convenient walk-in attic storage. With 5 bedrooms, 4.5 baths, thoughtful craftsmanship, and stylish finishes throughout, this exceptional new home offers the perfect blend of luxury, comfort, and functionality for today's lifestyle.

1833 Shillelagh Road, Chesapeake

$610,000

5 Beds ⋅ 2.1 Baths ⋅ 10646157 MLS

Tucked away on a quiet cul-de-sac and sitting pretty on a corner lot, this updated 5-bedroom, 2.5-bath home has room for everyone & everything. From the moment you walk in, you'll feel the perfect blend of comfort and function this home was designed for. Cozy up in the den by the fireplace, host holidays in the separate dining room, or get work done in the private office—there's a space for every part of your life. The kitchen shines with recessed lighting and a pantry, while the living room offers even more room to gather. Retreat to the primary suite, your own private escape complete with a second fireplace, a sitting area, and a spacious walk-in closet. The spa-like primary bath doesn't disappoint either, featuring a walk-in shower, soaking tub, dual sinks, and a linen closet for extra storage. Step outside onto your deck—ideal for weekend BBQs,or just soaking up some sunshine in your own private space. 2-car garage & shed means storage is never an issue.

807 Gresham Way, Chesapeake

$550,000

3 Beds ⋅ 2.1 Baths ⋅ 10645963 MLS

Wonderful opportunity to get 4+ acres in high rated schools. HUGE outbuilding with 3 bays garage bays, powered, multi-level, for storage and recreational activities. Home sold as is. Part of an estate. Seller to do no repairs.

2323 Herring Ditch Road, Chesapeake

$699,900

4 Beds ⋅ 3.1 Baths ⋅ 10645155 MLS

Welcome to this beautiful and spacious, well-maintained home that boasts 3261 sq.ft., four 2nd floor Bedrooms, 3.5 Baths + 1st floor Office, Dining Room, Sunroom, Family Room with cozy gas log fireplace, Living Room with handsome built-in bookcases, 12x10 shed, over 1/3rd acre corner lot, 1000 sq.ft. paver patio, 2nd floor Bedroom with ensuite bath & adjacent Loft is perfect for an In-Law Suite. 3 car garage provides ample parking and storage. Come see your dream home today!

2300 Burgess Court, Chesapeake

$230,000

10645662 MLS

This is a wooded 1.38 acre lot along a lightly traveled road that's being gradually redeveloped. Survey in hand as well as a wetlands delineation report done in 2025 showing about 0.88 Acre of wetlands and about 0.50 Acre of non-wetlands towards the back of the lot. Seller has already done soil test and the property can accommodate a single-family home. Soil analysis and location of septic field has been approved. Site plan is being drawn up. Construction entrance installed and lot underbrush cleared to allow walking access to the construction site. Buy now to build your custom dream home before the current owner builds on it.

2701 Seven Eleven Road, Chesapeake

$629,000

6 Beds ⋅ 3 Baths ⋅ 10645483 MLS

Rare 6-bedroom opportunity with an ideal multigenerational layout! The first floor features a bedroom, adjacent flex room, and a modified curbless shower, offering exceptional flexibility and accessibility. Beautiful neutral decor, 9' ceilings, hardwood floors, elegant crown molding, and a huge FROG provide room for everyone. The spacious primary suite features hardwood floors and two walk-in closets. Convenient second-floor laundry. Enjoy a large fenced backyard with a powered detached shed and private well for economical lawn irrigation, plus an attached 2-car garage. Meticulously maintained with annual service contracts on the HVAC, tankless water heater, and crawl space. Seller will provide a termite/moisture letter. Convenient to Millville Rd., Veterans Bridge, Shipyard Rd., and major interstates, Portsmouth, Norfolk and Suffolk! Small community vibe with minimal traffic. minimal traffic.

1816 Sunsprite Loop, Chesapeake

$529,900

4 Beds ⋅ 2.1 Baths ⋅ 10645403 MLS

You have seen the pictures and now I am sure you are curious about everything this house has to offer. Well, it is absolutely 100% turn-key, move-in ready with all of the bells and whistles. The home feels so good and invites tons of natural light. The kitchen has been thoughtfully remodeled adding tons of cabinet space, a center island, a pot filler and more functional layout. The cabinets, flooring (hand scraped bamboo), counters and appliances have all been recently upgraded as well. The bathrooms have all been remodeled and the primary bath is a small piece of heaven. Separate sinks, dual shower heads in the tile/glass shower and a separate soaking tub. Go outside and you might not go back in for quite a while. A covered porch and expansive deck greet you with the hot tub around the corner. Drop down to the 28,000 gallon in-ground pool complete with a built-in endless pool for serious swimmers. Backing up to the woods, this private, backyard paradise awaits you!

2107 Sunset Maple Lane, 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.