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

$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

$569,900

4 Beds ⋅ 2.1 Baths ⋅ 10646819 MLS

Welcome to this beautifully maintained 4 bedroom, 2 and a half bath, all-brick ranch in the Grassfield School District of Chesapeake. This home features updated eat-in kitchen to include granite counter tops, stainless steel appliances (KitchenAid Refrigerator), gas range, shaker cabinets, and fresh paint. Enjoy an open layout with a very spacious great room, vaulted ceilings and a gas fireplace. French doors offer privacy to the formal dining, living room/office. Stunning bamboo floors throughout the kitchen and living areas. The large finished bedroom over the garage offers new LVP flooring, lighting, shelving, built in reading nook or can be used as a bed. Major system upgrades include TRANE HVAC system installed in 2021 with duct work replaced and system zoned in 2025. RainSoft reverse osmosis, enclosed crawl space with dehumidifier, insulated garage doors, updated vents and a newer gas water heater. Half bath located next to the mudroom/laundry room, washer & dryer to convey. New carpet in all main floor bedrooms. Enjoy outdoor living on your covered front porch or in your private fenced in backyard and deck. Expansive attic space for storage and extended driveway for additional parking. A truly move-in-ready Chesapeake home, minutes to shopping, dining, and interstate access. Please ask for the detailed upgrade list of extensive repairs and improvements. The home has been meticulously maintained with major system updates throughout.

817 Doe Run Drive, Chesapeake

$825,000

5 Beds ⋅ 2.1 Baths ⋅ 10646792 MLS

Space to gather, land to enjoy, and a separate apartment for the people who matter most. Nearly 3,900 square feet in the main home, 3 private acres, a detached three-car garage, and an approximately 1,000-square-foot apartment above it. This sprawling ranch offers four first-floor bedrooms, including the spacious primary suite with dual closets, beautifully refinished hardwoods, fresh paint, updated lighting, newer roof, new carpet and an expansive kitchen with gas cooking and newer appliances. A finished bonus room upstairs serves as the fifth bedroom or flexible space for guests, hobbies, or a quiet retreat. An enormous walk-in attic provides rare expansion potential, with room to add finished living space for an even more complete upstairs retreat. Enjoy the new Trex deck and peaceful backyard with room to entertain, garden, play, and bring your horses-picture them grazing outside your kitchen window while your coffee brews. Dreaming of an inground pool and backyard oasis? There is room for that too. Need space for your in-laws? Above the detached garage, the separately metered apartment includes its own bedroom, full bath, kitchen, living area, and laundry, creating true independent space for extended family, guests, a studio, or private home office. The apartment is not counted in sq ft/bedroom/bath count in this listing. Well and septic mean no monthly city water or sewer bill. Located in Riverwood, a quiet acreage community known for spacious homesites, mature trees, room for horses, and a neighborhood boat launch for enjoying nearby waterways. Enjoy the space and privacy of South Chesapeake in the Grassfield school district. Come see the lifestyle you have been searching for.

3700 Riverwood Crescent, 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

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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.