Greenbrier Real Estate

Welcome to Greenbrier, a vibrant and flourishing subdivision nestled in the heart of South Chesapeake, Virginia. Known for its picturesque landscapes and welcoming community, Greenbrier offers an exceptional blend of suburban charm and modern convenience.

This delightful neighborhood is characterized by its tree-lined streets, well-maintained parks, and an array of beautiful homes that cater to diverse lifestyles. From cozy single-family residences to spacious townhomes, Greenbrier provides a variety of options for families, young professionals, and retirees alike. Residents relish the sense of community, with friendly neighbors and a strong commitment to maintaining the area’s appeal.

Greenbrier is ideally situated, offering easy access to major highways, making commutes to nearby cities a breeze. For those who enjoy shopping and dining, the Greenbrier area boasts a plethora of options, from boutique shops to popular restaurants and cafes. The nearby Greenbrier Mall is a local favorite, providing a wide range of retail experiences.

Nature enthusiasts will appreciate the numerous parks and recreational facilities in the vicinity, including walking trails, playgrounds, and sports fields, ensuring that there’s always something to do outdoors. Families benefit from the highly-rated Chesapeake Public Schools, making Greenbrier a desirable place to raise children.

With its perfect blend of community spirit, convenience, and natural beauty, Greenbrier in South Chesapeake is not just a place to live—it's a place to thrive. Discover your dream home in this enchanting subdivision and become a part of the Greenbrier legacy today!

Newest Listings in Greenbrier

$16

10647380 MLS

Excellent location directly off Executive Blvd. 1975 SF space located in the heart of the Greenbrier Submarket. Two story build out with office space, full bath, warehouse, and mezzanine available with current layout. Two dedicated parking spaces with several more open parking spaces available on a first come basis. Tenant is responsible for electric, janitorial, and telecommunications. Water is provided in rent. Rent is $2,550 per month. Landlord may be willing to provide up to 2 months off rent to help tenant with build-out expenses. Landlord will provide lease agreement.

1222 Executive Boulevard Unit 104, Chesapeake

$285,000

3 Beds ⋅ 1.1 Baths ⋅ 10647127 MLS

Super convenient Chesapeake & Greenbrier location. Three bedrooms 1.5 baths plus a separate dressing area in master bedroom includes a 3rd sink. Spacious kitchen with nice counter space, all appliances, and a big front bay window. Schedule an easy showing today. 2-private parking spaces and a cul-de-sac location with no through traffic. BRAND NEW COSTCO is coming to Greenbrier Mall. Easy commute all military bases & downtown Norfolk shipyards. Easy access to beachfront and Greenbrier restaurants, shopping, NFCU & banks. YMCA includes swimming pool and activities. Buyer has ability to pick replacement carpeting. HOA approves - backyard fencing can be painted by seller. Newer heat pump unit for heating and cooling with Coolant 410A. HVAC under yearly inspection program. Seller provides Termite/Moisture clearance via Hampton Roads Warranty Program. No flood insurance required. Trash & Recycle cans provided.

1218 Cedar Mill Square, Chesapeake

$215,900

2 Beds ⋅ 1 Baths ⋅ 10645553 MLS

Welcome home to the heart of Greenbrier! This charming and stylish 2-bedroom, 1-bath second-floor condo in the desirable Heather Pointe Condominiums offers the perfect combination of comfort, convenience, and updates. Conveniently located behind Greenbrier Mall, you'll enjoy easy access to shopping, dining, entertainment, and major interstates. The beautifully remodeled kitchen (2021) features granite countertops, upgraded soft-close cabinets, ceramic tile backsplash and flooring, stainless steel Whirlpool refrigerator, microwave, dishwasher, and a new electric range (2026). All appliances, including the washer and dryer, convey. Relax by the cozy gas fireplace in the spacious living room or enjoy your private balcony. New carpet throughout the home makes this condo move-in ready. Don't miss this wonderful opportunity—schedule your private showing today!

1709 Rock Bridge Mews Unit B, Chesapeake

$300,000

3 Beds ⋅ 1.1 Baths ⋅ 10646018 MLS

Ideally located in the heart of Greenbrier, this move-in-ready three-bedroom townhouse is the perfect find! Recently refreshed with updated flooring and renovated bathrooms, this home is ready for its new owners. Features include a spacious kitchen with plenty of counter space, a convenient laundry area, and roomy, comfortable bedrooms. Complete with a private, fenced-in backyard and patio, this home offers everything you need. Schedule your showing today!

1204 Cedar Mill Square, Chesapeake

$210,000

2 Beds ⋅ 2 Baths ⋅ 10645158 MLS

You do not want to miss this stunning condo! It features fresh paint throughout, professionally cleaned carpets, and appliances, making it move-in ready. Nestled right in the heart of Greenbrier, this location offers ultimate convenience with quick access to a selection of entertainment, dining, and shopping. Don't wait schedule your tour today and see this property for yourself!

2201 Rock Cliff Reach Unit A, Chesapeake

$299,000

3 Beds ⋅ 1.1 Baths ⋅ 10645266 MLS

Move in ready-well maintained Townhouse in desirable Greenbrier. LVT/Vinyl flooring throughout, carpet upstairs. Open floor plan with Large Livingroom, Kitchen, and Dining Area. Fenced in back yard and storage shed. Do not miss this move in ready home.

1346 River Birch Run, Chesapeake

$285,000

3 Beds ⋅ 1.1 Baths ⋅ 10645022 MLS

Be settled before summer ends! Townhome offers a modern/functional layout. First floor features a light & bright eat-in kitchen, SS appliances, ample counter space & vintage cabinets. Living room boasts an attractive wood burning fireplace, you'll finally have that mantle for holiday decorating! Three bedrooms up with a full bath, new carpet, fresh paint throughout. Enjoy direct access to the fully fenced back yard from the dining area. Back yard provides the perfect space for entertaining, relaxing or allowing pets to roam. Take advantage of the path that runs along the lake, just outside the rear gate.

939 Still Harbor Circle, Chesapeake

$375,000

3 Beds ⋅ 2 Baths ⋅ 10644346 MLS

You will love coming home to this comfortable ranch home with cozy rooms. Located near the intersection of Greenbrier Parkway and Volvo Parkway in Turtle Rock on a cul-de-sac. Enjoy the floor plan which includes living room, dining room, den with fireplace, eat-in kitchen, laundry room, primary bedroom with bathroom, two other bedrooms and hall bathroom. Walking trails & playgrounds nearby. Lots of shopping and dining closeby in Greenbrier area. This home has been well cared for and is ready for you. Welcome home!

1109 Hearthstone Landing, Chesapeake

$309,000

3 Beds ⋅ 2.1 Baths ⋅ 10642451 MLS

Welcome home to this charming and spacious interior townhome, perfectly located in the heart of everything! Offering nearly 1,600 sq ft of well-maintained living space, this home has 3 spacious sized bedrooms & 2.5 baths, providing the perfect blend of comfort and functionality. Filled with character and warmth, the thoughtfully designed floor plan offers plenty of room to relax and entertain. Step outside to enjoy the private backyard an ideal space for morning coffee or weekend entertaining! Conveniently located just minutes from the interstate, shopping, restaurants, and everyday amenities, you'll love the ease of living this central location provides. With ample parking and a welcoming neighborhood feel, this home truly has it all.

1404 River Birch Run, Chesapeake

$288,500

3 Beds ⋅ 1 Baths ⋅ 10642393 MLS

Cute 1 story cottage in the heart of Greenbrier Chesapeake on almost an acre of private wooded property. This charming 2 bedroom home with a bonus room that has been used as a 3rd bedroom (no closet). Bright and Airy vintage appeal. Galley Kitchen opens to dining room with arched opening to living room. Open concept with character. The property is zoned Industrial and the current legal use is residential (nonconforming-grandfathered) Buyers should independently verify requirements with the City of Chesapeake, for any plans for additions or redevelopment or converting to an Airbnb STR.

106 Greenbrier Road, Chesapeake

$259,900

2 Beds ⋅ 1.1 Baths ⋅ 10641047 MLS

NEW HVAC SYSTEM BEING INSTALLED! Charming 2-bedroom townhome in the highly desirable Greenbrier area! The main level features a spacious living room that flows seamlessly into the kitchen, creating an easy, comfortable layout. The kitchen offers ample cabinetry and counter space, a new refrigerator, and room for a breakfast table. Sliding glass doors lead to a fully fenced backyard with a patio, for relaxing or entertaining. Upstairs, you’ll find two large bedrooms, each with generous closet space and access to a full bathroom. Enjoy peaceful neighborhood walking paths around the lake, all while being conveniently located near shopping, dining, and everyday essentials.

918 Seabreeze Court, Chesapeake

$450,000

10639627 MLS

Well-established, highly profitable Mediterranean restaurant generating $700K+ in annual gross sales with strong, consistent cash flow. This is a turnkey operation situated in a prime, high-traffic location with a deeply loyal local customer base. The favorable lease is secured through 2030 at $3,900/month. Multiple flexible purchasing options are available to fit your investment goals: Purchase the established brick-and-mortar Restaurant Business alone for $300,000. Acquire the complete mobile expansion assets, including a brand-new, fully branded food trailer and dedicated Ford tow vehicle, for an additional $150,000. Purchase the entire comprehensive package (Restaurant + Trailer + Tow Vehicle) for $450,000. This is an incredible turnkey opportunity perfectly suited for an owner-operator or an investor looking to immediately capitalize on established dine-in, catering, and lucrative mobile/festival revenue streams. Complete financial records (POS data and tax returns) and an equipment inventory list are available upon request with a signed NDA. Seller is relocating. Please do not disturb employees or discuss the sale on-site. All showings are strictly by appointment only. Serious, qualified buyers only.

1437 Sam's 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.