Chesapeake Homes with Grassfield High school

Welcome to South Chesapeake, Virginia, a hidden gem nestled in the heart of Chesapeake City. This vibrant community offers a perfect blend of suburban charm and urban convenience, making it an ideal place for families, professionals, and retirees alike. With its picturesque neighborhoods, lush greenery, and a strong sense of community, South Chesapeake is a place where you can truly feel at home.

One of the standout features of South Chesapeake is its proximity to Grassfield High School, a highly regarded institution known for its commitment to academic excellence and a wide array of extracurricular activities. Families residing in this area benefit from access to quality education, ensuring that children receive the best possible start in life. The school’s dedicated staff and diverse programs foster a supportive environment that encourages students to thrive.

The real estate market in South Chesapeake is diverse, offering a variety of homes that cater to different lifestyles and budgets. From charming single-family homes with spacious yards to modern townhouses, there’s something for everyone. Many properties feature beautifully landscaped lawns, providing the perfect backdrop for outdoor gatherings and family activities.

In addition to excellent schools, South Chesapeake boasts a range of amenities, including parks, shopping centers, and dining options. Residents can enjoy leisurely strolls along scenic trails, engage in community events, and explore the nearby natural beauty of the Chesapeake Bay.

With its welcoming atmosphere and strong community ties, South Chesapeake is more than just a place to live—it's a place to thrive. Discover your dream home in this enchanting city today!

Newest Chesapeake Homes with Grassfield High school

$455,000

3 Beds ⋅ 2.1 Baths ⋅ 10647905 MLS

Built in 2021, this beautifully designed townhouse-style condo offers 2,234 square feet of thoughtfully designed living space, featuring an open floor plan and a desirable first-floor primary suite. The spacious great room with soaring ceilings flows seamlessly into the kitchen, complete with granite countertops, stainless steel appliances, a pantry, peninsula seating, and an adjoining dining area. The primary suite features a generous walk-in closet and an en-suite bath with a double vanity and oversized shower. Upstairs, you'll find two spacious bedrooms, a full bath, a loft overlooking the great room, and an unfinished storage room for abundant storage. Additional highlights include a two-car attached garage, large laundry room, and tankless water heater. A private rear patio provides the perfect spot to relax and unwind. Enjoy low-maintenance living with resort-style amenities including a clubhouse, pool, dock, playgrounds, private beach, and ground maintenance, all within the highly sought-after Grassfield school district.

1758 Barkadeer Cove, Chesapeake

$660,000

4 Beds ⋅ 2.1 Baths ⋅ 10647705 MLS

Experience the perfect blend of quality, comfort, and outdoor living at 1928 Rockwood Drive in the highly sought-after Grassfield School District! Originally built by Stephen Alexander Homes, this beautifully maintained home is tucked away in a quiet neighborhood and features a dedicated office/study, second-floor laundry, and a spacious primary suite with soaring cathedral ceilings. The inviting living room showcases a gas fireplace flanked by custom built-ins. Outside, enjoy a private backyard oasis with an in-ground pool and TREX decking, installed in 2020. Additional updates include new windows and doors, installed in 2021. Complete with a two-car attached garage and driveway parking for four vehicles, this home truly has it all!

1928 Rockwood Drive, Chesapeake

$950,000

6 Beds ⋅ 5 Baths ⋅ 10647670 MLS

Welcome home to this exceptional 6-bedroom, 5-bath residence in the heart of Great Bridge in Chesapeake, wonderfully situated on a peaceful cul-de-sac. Designed with both comfort and functionality in mind, this spacious home features two inviting living areas, including one with a cozy fireplace, providing plenty of room to relax and entertain. The beautifully updated kitchen is the heart of the home, showcasing modern finishes, abundant cabinetry, and generous workspace. Retreat to the luxurious primary suite, complete with two walk-in closets and a spa-inspired ensuite featuring a large soaking tub for the ultimate in relaxation. A dedicated home office offers the perfect space for remote work, studying, or creative projects. Step outside to your private backyard retreat, where an in-ground pool and expansive fenced yard create the ideal setting for entertaining, outdoor recreation, or simply unwinding. Adding incredible versatility, the property also includes both an attached garage and a detached garage with a private in-law suite above. This separate living space features a bedroom, full bathroom, and kitchenette, great for guests, multigenerational living, or potential rental income. With its spacious layout, thoughtful updates, and outstanding amenities, this home truly has it all. Don't miss your opportunity, schedule your private tour today!

821 Spruce Forest Court, Chesapeake

$485,000

3 Beds ⋅ 2.1 Baths ⋅ 10647359 MLS

Light-filled, completely move-in ready home, on a large lot in the highly sought-after Sawyer's Mill neighborhood. The home offers an open concept with new flooring & fresh paint throughout. The primary shower was just redone & the HVAC was replaced in 2021. The Sawyer's Mill community offers playground, pool, and clubhouse - all while being zoned for Grassfield schools!

312 Sawmill Arch, Chesapeake

$699,000

5 Beds ⋅ 3 Baths ⋅ 10647461 MLS

Welcome home to this large, move-in ready five-bedroom, three-bathroom residence in a sought-after Chesapeake neighborhood. Inside, discover a full kitchen renovation with smart appliances, fresh paint, and new flooring. Step outside to your ultimate backyard retreat, featuring a new deck, a fenced in-ground swimming pool, and an outdoor fireplace with a dedicated sitting area. The layout also includes a convenient bedroom and full bathroom on the first level.

1076 Scenic Boulevard, Chesapeake

$650,000

4 Beds ⋅ 3 Baths ⋅ 10647231 MLS

Welcome home to this beautifully updated all-brick detached condo tucked away in a quiet, peaceful community. Enjoy relaxing mornings on the inviting covered front porch with porch swing or covered rear porch and patio overlooking the beautifully maintained yard with extensive irrigation upgrades and lush landscaping throughout. Designed for easy living, this home offers mostly one-level living with a spacious room over the garage featuring its own en-suite bath. The luxurious remodeled kitchen opens seamlessly to the living area and boasts top-of-the-line stainless steel appliances, granite countertops, and a walk-in pantry. Engineered bamboo flooring, fresh paint, updated lighting and ceiling fans, plus a whole-home gas generator add comfort and peace of mind. A massive walk-in attic offers incredible storage or future expansion. HVAC replaced in 2020, and a tankless water heater was installed in 2023.

522 Bells Hollow Court, Chesapeake

$7,900

10647463 MLS

Vacant Land in Hillcrest subdivision. Zoned for great schools! Drive by anytime. Seller has never occupied the land, has no information to share. Buyer to perform all due diligence.

14 Blk Tuck Street, Chesapeake

$675,000

5 Beds ⋅ 3 Baths ⋅ 10647378 MLS

Meticulously maintained 5-bedroom, 3-bath home in sought-after Las Gaviotas offering over 3,000 sq ft of bright, open living space with water views. Flexible layout includes 1st floor bedroom and bath, huge FROG can be bedroom, office, flex space. 2 Bathrooms feature updated Onyx showers for a modern touch. Enjoy a private, wooded backyard overlooking the canal—perfect for relaxing or entertaining. Ample storage throughout. A whole-house generator provides peace of mind, and no flood insurance is required. Community includes a pool, clubhouse, and golf - pool and golf have optional membership. Don’t miss this exceptional cul-de-sac opportunity!

504 Aguila Court, Chesapeake

$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

$609,000

5 Beds ⋅ 3 Baths ⋅ 10646979 MLS

Tired of expensive water and sewer bills, HOA restrictions, or dealing with the stress and cost of a fixer upper? Then this brand new home is exactly what you have been waiting for. Welcome to this stunning 2,600 sq. ft. open concept residence built by local award winning builder. Featuring 5 spacious bedrooms, including a first floor bedroom great for guests or multi generational living, and 3 full baths with upscale designer finishes throughout. Enjoy luxury features including granite countertops, ceramic tile, luxury vinyl plank flooring, a cozy fireplace, and a beautiful standalone soaking tub. With NO HOA, this property is superb for boat owners, campers, trailers, or anyone wanting freedom and flexibility without extra fees or restrictions. Located in a highly sought school district with flexible spaces wonderful for entertaining and everyday living. Everything is brand new, offering peace of mind and low maintenance living.

789 Caddie Street, Chesapeake

$599,000

4 Beds ⋅ 2 Baths ⋅ 10646894 MLS

This is the one you’ve been waiting for! Beautifully updated & filled w/ character, this 2,800-square-foot ranch delivers 4 bedrooms, 2 baths and an incredible blend of indoor comfort & outdoor resort-style living. Covered front porch welcomes you to a light-filled interior where floor-to-ceiling windows surround the sunroom, while the family room showcases a fireplace, built-in bookcase & extensive molding. The spacious primary suite offers walk-in closets plus a versatile sitting area perfect for a home office, reading retreat or private escape. Outside, prepare to be wowed! The expansive backyard is your own private oasis with a 26,000-gallon saltwater pool (new pump 2025, salt cell 2026), deck, gazebo, fire pit, hammocks, pool house, sheds, fish pond with fountain, weeping willow, mature Japanese maple, peach tree and lush gardens. Smart-home features and Wi-Fi irrigation add modern ease. Finished room over garage, expansive attic, numerous updates & low traffic dead-end street.

318 Rio Drive, 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.