Grassfield Real Estate

Welcome to Grassfield, a charming neighborhood nestled in the heart of South Chesapeake, Virginia. Known for its picturesque landscapes and community spirit, Grassfield offers a perfect blend of suburban tranquility and modern convenience. This vibrant community is ideal for families, retirees, and anyone looking to enjoy a peaceful lifestyle while remaining close to the bustling city life.

One of Grassfield's standout features is its beautifully designed homes, which reflect a variety of architectural styles and sizes, catering to diverse tastes and lifestyles. Tree-lined streets and well-maintained parks create a welcoming atmosphere, making it easy for residents to enjoy leisurely strolls or family picnics in the sun. The neighborhood is also home to top-rated schools, ensuring that children receive a quality education just a stone’s throw away from home.

Grassfield is conveniently located near major highways, making commuting to nearby cities and attractions a breeze. Residents can enjoy easy access to shopping centers, dining options, and recreational facilities, including golf courses and nature trails. For those who appreciate the outdoors, the nearby Great Dismal Swamp National Wildlife Refuge offers stunning views and opportunities for hiking, bird watching, and exploring nature.

Community events and gatherings foster a strong sense of belonging among residents, making Grassfield not just a place to live, but a place to thrive. Whether you’re looking for a friendly neighborhood, excellent amenities, or a serene environment, Grassfield has it all. Discover your dream home in this delightful corner of Chesapeake, where every day feels like a getaway!

Newest Listings in Grassfield

$524,900

3 Beds ⋅ 2 Baths ⋅ 10642197 MLS

Situated on 5 acres in Chesapeake's Grassfield High School district, this move-in-ready 3-bed, 2-bath home features a 720 sq. ft. detached, fully powered workshop—great for a contractor or hobbyist. Located near Deep Creek Park and the Dismal Swamp Canal Trail, enjoy peaceful surroundings, deer sightings, and views of sailboats on the Intracoastal Waterway. A 2012 renovation opened the layout, updated the kitchen and baths, and added central duct HVAC. Recent improvements include a new 3-ton heat pump (2023), whole-house paint (2024), new carpet (2025), and new utility room vinyl flooring, plus upgraded electrical, plumbing, and replacement windows. Outdoors features a fenced yard with mature fruit and fig trees throughout the property. Motivated seller facing an unexpected military relocation (PCS). Contact agent for more information!

317 George Washington Highway S, South Chesapeake

$125,000

10617958 MLS

Seller would prefer to sell adjacent lot- (In MLS) together. Great opportunity to build 2 homes one on each lot. Very Private but easily accessible, as property is surrounded by protected land and unbuildable for long term security. Property is adjacent to the biking path on The Great Dismal Swamp. Great Hunting and outdoors enthusiast dream in your backyard, property backs to Dismal Swamp Tract of Cavalier Wildlife Management Area. Each lot is ~2.5 acres. Drive by to view. Wetlands study and Topo Survey in Docs. City confirmed both lots buildable and legally accessible. Also, good opportunity for tree farm lease and harvesting, never logged before. Utilities are starting to go in on new road in front of property. These properties do not come up for sale often. Call for more information and a private showing! Take George Washington HWY to Cornland Rd, Cornland dead ends to Dismal Swamp Trail, turn right and lots are on the right hand side.

2.5 Ac Dismal Swamp Canal Trail, South Chesapeake

$125,000

10617956 MLS

Seller would prefer to sell adjacent lot- (In MLS) together. Great opportunity to build 2 homes one on each lot.Very Private but easily accessible, as property is surrounded by protected land and unbuildable for long term security. Property is adjacent to the biking path on The Great Dismal Swamp. Great Hunting and outdoors enthusiast dream in your backyard, property backs to Dismal Swamp Tract of Cavalier Wildlife Management Area. Each lot is ~2.5 acres. Drive by to view. Wetlands study and Topo Survey in Docs. City confirmed both lots buildable and legally accessible. Also, good opportunity for tree farm lease and harvesting, never logged before. Utilities are starting to go in on new road in front of property. These properties do not come up for sale often. Call for more information and a private showing! Take George Washington HWY to Cornland Rd, Cornland dead ends to Dismal Swamp Trail, turn right and lots are on the right hand side.

2.5 Ac Dismal Swamp Canal Trail, 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.