Chesapeake VA County Real Estate

Welcome to Chesapeake, Virginia – a vibrant city that beautifully blends the charm of Southern living with the convenience of modern amenities. Nestled in the heart of Hampton Roads, Chesapeake is known for its stunning natural landscapes, rich history, and a plethora of recreational opportunities.

With over 22 miles of waterfront along the Elizabeth River and the Intracoastal Waterway, Chesapeake is a paradise for water enthusiasts. Residents and visitors alike can enjoy a variety of outdoor activities such as boating, fishing, and kayaking. The city's extensive park system, including the picturesque Great Dismal Swamp National Wildlife Refuge, offers countless trails for hiking, biking, and wildlife observation, making it a haven for nature lovers.

Chesapeake is not just about the great outdoors; it also boasts a thriving community with excellent schools, diverse dining options, and a robust economy. The city is home to a mix of charming neighborhoods, from historic districts to modern developments, catering to families, young professionals, and retirees alike. Whether you’re looking for a cozy single-family home or a contemporary townhouse, Chesapeake has something to suit every taste and budget.

Culturally, Chesapeake is rich with heritage, celebrating its history through various festivals and events throughout the year. The local arts scene is thriving, with galleries, theaters, and live music venues that keep the community entertained.

In Chesapeake, you’ll find not just a place to live, but a place to thrive. With its unique blend of natural beauty, community spirit, and endless opportunities, it’s no wonder why so many choose to call Chesapeake home. Come and discover the charm of this remarkable city!

Newest Listings in Chesapeake VA County

$390,000

3 Beds ⋅ 2.1 Baths ⋅ 10648235 MLS

The moment you walk through the door, you'll feel right at home. The spacious open layout is perfect for everyday living, whether you're enjoying a quiet evening or hosting friends and family. The thoughtfully designed primary suite offers a private retreat with a full bath and generous walk-in closet, while luxury vinyl plank flooring flows throughout the home. Recent improvements, including the 2023 addition, updated kitchen cabinetry, windows, electrical, heat pump, lighting and, fixtures, provide modern comfort and peace of mind. Outside, the fenced corner lot offers plenty of room to enjoy, with a deep driveway for ample parking. Located in an established Chesapeake neighborhood with convenient access to shopping, dining, parks, and major commuter routes, this home is one you'll want to experience in person before it's gone.

1324 Hawthorne Drive, Central Chesapeake

$825,000

4 Beds ⋅ 3.1 Baths ⋅ 10648270 MLS

Beautiful custom home on 3 Acres that backs up to woods! Two Primary Suites, one downstairs and one upstairs each with their own full bath! Amazing custom Kitchen with loads of storage, Pantry, plenty of counter space, center island, brand new cabinets, granite and Stainless Steel Appliances! Dual zoned central Heat/AC. Move in ready! Located in the Grassfield School district! Completely remodeled and waiting for you, be sure to come check this one out first!No HOA, bring your horses, chickens and goats!

2239 Benefit Road, South Chesapeake

$269,900

3 Beds ⋅ 1 Baths ⋅ 10648228 MLS

Ready for you to move right in! This fully refreshed 3 bed, 1 bath home has all the big-ticket updates already done for you. Brand-new flooring throughout (July 2026), fresh interior paint (2025), and new siding (2025) give it a clean, updated feel from the moment you walk in, while the roof on both the home and the detached garage was replaced just 4 years ago. Out back is where this property really stands out: a 16x24 detached garage with electric and attic storage makes an ideal workshop, hobby space, or overflow storage, and TWO additional carports mean covered parking for multiple vehicles, a boat, or a trailer. If you've been looking for a truly move-in-ready home with serious garage and parking space, 809 Clay Avenue delivers. Call to schedule your showing today!

809 Clay Avenue, South Chesapeake

$301,000

2 Beds ⋅ 2.1 Baths ⋅ 10648248 MLS

Welcome to your move-in ready townhome in the desirable Great Bridge Area. This well maintained home offers a functional layout, sought after schools, NO HOA fees, new HVAC in 2025 and all new carpeting. Enjoy the spacious living room with a wood-burning fireplace to spend cozy evenings, or step outside to your fully fenced, private backyard with a storage area and firepit. Primary Bedroom with en suite is great for relaxing. Located with convenient access to shopping, dining, and everyday amenities, this home will not disappoint. Make this your first stop!

406 Middle Oaks Drive, South Chesapeake

$500,000

4 Beds ⋅ 2.1 Baths ⋅ 10648263 MLS

Stunning waterfront views! Spacious Brick front ranch with a new kitchen, quartz countertops, new stainless appliances, slow close cabinets, large island and 42" upper cabinets. Eat in kitchen with bay windows overlooking the lake! Large family room, LVP flooring and an oversized deck with an awning. Sits on over 1/4-acre with a 2-car garage and a recent solar panel installation. There is structural termite and moisture damage in the crawl space and the home. Only CASH offers will be considered. Buyer must assume the solar panel loan, approx. $35,000. 19 years @ $150.00 a month. Electric bills as low as $10.00 a month.

1121 Copper Stone Circle, South Chesapeake

$950,000

5 Beds ⋅ 3 Baths ⋅ 10648261 MLS

Welcome to your private 3.25-acre country oasis, where luxury finishes, heavy-duty infrastructure, and absolute peace of mind converge. This beautifully updated single-story home offers an open-concept layout and highly functional spaces, making it a rare market find. INTERIOR HIGHLIGHTS Step inside to a bright, airy open floor plan where the living and dining areas flow seamlessly into the chef-inspired kitchen. The kitchen is outfitted with premium Cambria countertops for unmatched durability and sleek modern style. The primary suite serves as a spa-like retreat, boasting natural quartzite surfaces, a deep jetted soaking tub, and a massive 4x4 walk-in shower. Upstairs, a versatile finished room over the garage (FROG) and a charming attic dormer offer excellent bonus spaces for a home office, media room, gym, or guest quarters. OUTDOOR LIVING & ENTERTAINING Embrace the scenic acreage from your choice of outdoor living areas. Relax on the welcoming covered front porch, or host unforgettable gatherings on the expansive rear covered patio. The outdoor living experience is anchored by a fully equipped outdoor kitchen, great for weekend barbecues and dining al fresco while overlooking your sprawling, private acreage. THE ULTIMATE DETACHED WORKSHOP A true standout feature is the massive 2,200 sq. ft. detached workshop. This incredible building is fully powered and completely climate-controlled with heating and cooling, making it an ideal setup for a home business, car enthusiast, hobbyist, or extensive machinery storage. PREMIUM SYSTEMS & INFRASTRUCTURE No expense was spared on the home's mechanics and structural integrity: * Power Security: Whole-home generator supported by a recently added 500-gallon propane tank. * Efficiency: All-new energy-efficient windows and updated insulation throughout. * Roof & Plumbing: Roof is approx. 4 years young. All plumbing has been fully updated with zero cast iron. * Utilities: Tankless water heater for endless hot water; septic system recently serviced. Welcome Home.

1908 Benefit Road, South Chesapeake

$974,500

4 Beds ⋅ 3.1 Baths ⋅ 10648249 MLS

Grace, Beauty, Functionality, Beautiful private location (acreage on a cul de sac) , only 10 lots on clear land bordered by mature trees as a backdrop. The primary opulent primary bath including an extra large closet and another large en suite are on the first floor along with a flex room. Amazing storage over the THREE car garage with room for EVERYTHING. Newest feature is a "butlers kitchen" complete with full sink tucked just behind the well equipped main kitchen. Two additional large bedrooms upstairs. Covered rear porch with an amazing view! You couldn't ask for more. This semicustom building package is hard to beat! We have additional lots and plans available. This will be the last acreage neighborhood to be approved within the city. No main road lots here! If you are looking for new construction it a definite 'MUST SEE"! Ponds, wildflower field, private walking trail and more add up to an exceptional "positive vibe" . No upgrades needed, some see! Preferred lender incentives.

4020 Tucker Lane, South Chesapeake

$625,000

4 Beds ⋅ 3 Baths ⋅ 10648242 MLS

Welcome to this stunning beautiful home nestled on a quiet cul-de-sac! From the moment you enter, you’ll appreciate the grand condition of this home, featuring 4 bedrooms, 3 full bathrooms and thoughtful updates throughout. Gorgeous hardwood floors running through the main living area and in the expansive room over the garage. At the heart of the home is a fully renovated gourmet kitchen featuring sleek white quartz countertops, premium stainless steel appliances, and ample cabinet space—flawless setting for everyday living and entertaining. Upstairs, the luxurious primary suite serves as a private retreat, complete with a spa-inspired ensuite bath featuring dual vanities and a custom dual shower. Roof is approx. 7 years old, brand-new replacement windows, dual-zone HVAC system and encapsulated crawl space, for year-round comfort. Step outside to take in serene lake views and enjoy the peaceful backyard setting. Truly turn-key and move-in ready—schedule your tour today!

811 Twin Peak Ct Court, South Chesapeake

$215,000

10648163 MLS

Outstanding 2.0-acre building lot in Chesapeake! This beautiful homesite offers approximately 135 feet of road frontage, a peaceful setting, and plenty of room to create the home you've always envisioned. Zoned R-15S, with city water available, this property combines the charm of country living with the convenience of nearby shopping, restaurants, and major highways. Enjoy the space and privacy that only a two-acre homesite can provide while remaining close to everything Chesapeake has to offer. Don't miss this exceptional opportunity to own one of the area's most desirable building sites. Private septic system will be required. Buyer is responsible for conducting all due diligence regarding soil evaluation, septic permitting, and installation requirements.

260 Centerville Turnpike N, South Chesapeake

$315,000

2 Beds ⋅ 1 Baths ⋅ 10648165 MLS

Rare 1.54-acre homesite in a highly desirable Chesapeake location! The property includes an existing home and out buildings that convey as-is. Suitable for renovation. R-15S zoning and an outstanding location near Greenbrier, major highways, shopping, dining, and schools, this property offers endless possibilities for investment.

304 Centerville Turnpike N, South Chesapeake

$300,000

2 Beds ⋅ 1 Baths ⋅ 10647978 MLS

Investors! 2 Parcels totalling 22.25 +/- acres currently zoned M1 for large tract (17.5acres) and residential small tract (4.75 acres) This piece of land must be purchased with 1828 Mount Pleasant Road which is right nextdoor and runs parallel to property and has a small house with power, septic and well. Subject to zoning, interested parties should contact the City of Chesapeake Zoning and Planning for allowable uses.

1832 Mount Pleasant Road, South Chesapeake

$1,950,000

10647774 MLS

Great Opportunity, 2 Parcels totalling 22.25 +/- acres currently zoned M1 for large tract and residential for small tract This piece of land must be purchased with 1832 Mount Pleasant Road which is right nextdoor and runs parallel to property and has a small house with power, septic and well. Subject to zoning, interested parties should contact the City of Chesapeake Zoning and Planning for allowable uses.

1828 Mount Pleasant Road, 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.