Greenbrier Real Estate

Welcome to Greenbrier, a vibrant and inviting neighborhood nestled in the heart of South Chesapeake, Virginia. Known for its stunning landscapes and family-friendly atmosphere, Greenbrier is the perfect blend of suburban charm and modern convenience.

One of the standout features of Greenbrier is its diverse array of housing options, ranging from cozy single-family homes to spacious townhouses, catering to a variety of lifestyles and budgets. The community is surrounded by lush parks and scenic walking trails, making it an ideal spot for outdoor enthusiasts and families looking to enjoy nature. The nearby Chesapeake City Park and Greenbrier Park offer ample opportunities for picnicking, jogging, and leisurely strolls.

Greenbrier’s location is a significant draw for residents. With easy access to major highways, commuting to Norfolk, Virginia Beach, and other surrounding areas is a breeze. The neighborhood is also home to an array of shopping and dining options, including the popular Greenbrier Mall, which features a mix of retail stores, restaurants, and entertainment venues.

Education is a priority in Greenbrier, with several highly-rated public and private schools serving the community. Families can take comfort in knowing that their children have access to quality education right in their backyard.

In addition to its amenities, Greenbrier boasts a strong sense of community. Neighborhood events and gatherings foster connections among residents, making it easy to feel at home. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, Greenbrier offers a welcoming environment that truly feels like home. Come explore all that this delightful neighborhood has to offer!

Newest Listings in Greenbrier

$450,000

3 Beds ⋅ 2 Baths ⋅ 10655585 MLS

Welcome to 1416 Woodside Court, a charming Chesapeake ranch offering comfortable one-level living and a floor plan designed for everyday life and entertaining. The spacious eat-in kitchen features granite countertops and a large center island, while the inviting living area is anchored by a wood-burning fireplace. Three bedrooms, two full baths, and a two-car garage provide plenty of flexibility. Major updates include a new 30-year architectural roof and water heater, both replaced in 2025 as well as new flooring in the bedrooms. Outside, enjoy a large backyard with room to relax, play, garden, or entertain. Tucked away on a court yet conveniently located near interstate access, shopping, dining, and everyday amenities, this move-in-ready home combines thoughtful updates and welcoming spaces.

1416 Woodside Court, South Chesapeake

$279,900

3 Beds ⋅ 1.1 Baths ⋅ 10645266 MLS

Do not miss this move-in-ready end-unit townhouse in the heart of Greenbrier! It offers 3 bedrooms, 1.5 baths, and 1,244 square feet. The kitchen, bathrooms, roof, and HVAC have all been updated within the past 5–7 years. All appliances convey. The home features an open layout, a spacious living room with a cozy fireplace, an updated kitchen, LVP flooring throughout the main level, and carpeting upstairs. Outside, enjoy a private, fully fenced backyard with a storage shed. Two assigned parking spaces add convenience. Located near Greenbrier’s shopping, restaurants, and major commuter routes. Schedule your showing today! Installation of New Tub is available if desired.

1346 River Birch Run, South Chesapeake

Start Your Search

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.