Chesapeake VA County Real Estate

Welcome to Chesapeake, Virginia – a vibrant city where Southern charm meets modern living! Nestled in the heart of Hampton Roads, Chesapeake is a unique blend of rich history and contemporary conveniences. With its picturesque landscapes, diverse communities, and a wealth of recreational opportunities, it’s no wonder that Chesapeake is one of the most sought-after places to live in Virginia.

Chesapeake boasts an impressive array of natural beauty, featuring over 22,000 acres of parks and open spaces, including the stunning Great Dismal Swamp National Wildlife Refuge. Whether you enjoy hiking, birdwatching, or simply soaking in the serene views, Chesapeake offers an outdoor paradise right at your doorstep. The city is also home to a variety of waterways, perfect for boating, fishing, and kayaking enthusiasts.

Families will appreciate the exceptional educational opportunities provided by the Chesapeake Public Schools system, which is dedicated to fostering academic excellence and personal growth. The community also supports a variety of cultural events and activities, ensuring that there’s always something exciting happening.

Chesapeake’s real estate market is diverse, offering everything from charming single-family homes to upscale waterfront properties. With its friendly neighborhoods and convenient access to nearby cities like Norfolk and Virginia Beach, residents enjoy the perfect balance of tranquility and urban amenities.

Whether you’re looking to buy your first home, relocate, or invest, Chesapeake, VA, is a city that welcomes you with open arms. Discover the endless possibilities that await in this beautiful community, where you can truly feel at home.

Newest Listings in Chesapeake VA County

$425,000

3 Beds ⋅ 2.1 Baths ⋅ 10646473 MLS

Welcome to this beautifully maintained 3 bedroom, 2.5 bath home. Step inside to a bright, open floor plan featuring rich dark wood floors that flow throughout the main living areas. The stunning kitchen is designed to impress with custom cabinetry, upgraded appliances, and plenty of space for cooking and entertaining. The inviting great room is the heart of the home, complete with gas fireplace and custom built-in shelving, creating the perfect space to relax or gather with family and friends. Upstairs, you'll find spacious bedrooms, including a comfortable primary suite, offering room for everyone to spread out. Outside, enjoy your own private patio, ideal for morning coffee or simply unwinding after a long day. Residents enjoy fantastic community amenities, including a pool, clubhouse, and exterior grounds maintenance, allowing you to spend more time enjoying your home and less time on upkeep. BRAND NEW ROOF (July 2026). Don’t miss your opportunity to make this your next home!

515 Sweet Leaf Place, South Chesapeake

$379,800

4 Beds ⋅ 2 Baths ⋅ 10646508 MLS

Welcome home to this beautifully renovated ranch in the heart of Chesapeake! Situated on a spacious lot in the established Ind. River neighborhood, this move-in ready home has been completely transformed with stylish, modern finishes throughout. Offering 4 bedrooms and 2 full baths, the flexible floor plan provides plenty of space for family, guests, a home office, or multigenerational living. The stunning new kitchen features contemporary cabinetry, updated countertops, and stainless steel appliances, while both bathrooms have been tastefully remodeled. Enjoy new flooring, fresh paint, updated lighting, and countless upgrades that make this home feel like new. Outside, the large backyard offers endless possibilities for entertaining, gardening, or relaxing. Conveniently located near shopping, dining, interstates, military bases, and schools, this turnkey home is ready for its new owner. Don't miss this incredible opportunity to own a fully renovated home in a prime Chesapeake location.

4328 Fontana Avenue, Central Chesapeake

$285,000

3 Beds ⋅ 1.1 Baths ⋅ 10646402 MLS

Welcome to this beautifully updated townhouse featuring fresh updates throughout. Brand-new carpet, new flooring, fresh interior paint, and new countertops give the home a clean, modern look and feel. A two-car driveway adds the convenience of dedicated parking. Thoughtfully refreshed and move-in ready, this home offers a great opportunity for its next owner.

1908 Devonwood Common, South Chesapeake

$750,000

5 Beds ⋅ 3 Baths ⋅ 10646148 MLS

Welcome home to this stunning Stephen Alexander "Caramel Cottage" in the highly sought-after Hanbury Woods — one of Great Bridge's most desirable communities. This 5-bedroom, 3-bath home checks every box: a first-floor bedroom and full bath perfect for guests or multigenerational living, 10' ceilings, rich hardwood floors, and an open-concept living area anchored by custom built-ins and a cozy gas fireplace. The chef's kitchen is the heart of the home — 42" white cabinetry, an oversized island, stainless appliances, and a walk-in pantry give you space to cook, entertain, and gather. Step out to the three-season Eze-Breeze porch and take in a private backyard with a large paver patio — your own retreat for morning coffee or evening wine. Upstairs, the primary suite is a true escape: spa-like bath, tiled shower, soaking tub, dual vanities, and a huge walk-in closet. Two more bedrooms and a spacious media/flex room round out the second floor, giving everyone room to spread out. This is a premium, highly requested model loaded with upgrades throughout — a rare find at this price point. Located in the heart of Great Bridge with top-rated schools and easy access across all of Hampton Roads, this home offers the space, quality, and location today's buyers are looking for. Homes like this in Hanbury Woods don't last — schedule your showing today

1153 Edinburg Parkway, South Chesapeake

$145,000

3 Beds ⋅ 1.1 Baths ⋅ 10646471 MLS

3936 Holly Cove Drive, West Chesapeake

$520,000

4 Beds ⋅ 3.1 Baths ⋅ 10646463 MLS

If you’ve been searching for true peace and privacy without sacrificing convenience, this Grassfield gem is an absolute must-see. Set back from the street on a private driveway, the property opens up to nearly an acre of total solitude, completely enveloped by woods and lush mature greenery. Inside, fresh paint brings a bright, inviting energy to a floor plan built for real life. The layout is a rare find for multi-generational living, featuring two distinct main-level suites. The in-law wing includes its own living room, making it easy to use as a private apartment, a 5th bedroom, or a home office. The primary suite feels like a custom getaway with live-edge wood countertops, dual shower heads, and a custom walk-in closet system. Out back, the property turns into a full outdoor retreat featuring a storage shed, a chicken coop, separate hookups ready for a pool and hot tub, and a massive detached two-car workshop/garage complete with a carport and RV hookup. Welcome home!

891 Bells Mill Road, South Chesapeake

$369,900

4 Beds ⋅ 2.1 Baths ⋅ 10646345 MLS

Functional 4-bedroom, 2.5-bath home offering a versatile layout with flexible living spaces. An additional room provides options for a home office, playroom, hobby space, or other household needs. The fenced backyard includes a patio for outdoor enjoyment and a storage shed for added convenience. Recent updates include a new HVAC system and newer kitchen appliances. Located approximately two blocks from Lakeside Park and conveniently situated near military installations, hospitals, shopping, dining, and major highways for easy commuting.

1130 Orville Avenue, Central Chesapeake

$739,900

5 Beds ⋅ 3.1 Baths ⋅ 10646366 MLS

See features sheet & survey attached — you’ll be amazed by this NEW custom home by Overholt Contracting (40+ yrs)! Must see now: modern floorplan with 2 spacious primary suites (or use one as a game room), 4 large bedrooms, first-floor home office, high-end kitchen & baths with quartz, freestanding tub + tiled shower, smart-home Wi-Fi, and full landscaping with sod. Sited on almost 1/2 acre in Hickory (Chesapeake) on city/county septic & water — NO HOA, additional buildings allowed, room for pool, boat or RV. James Hardie siding, carriage garage door with glass, brushed concrete patio. Closing cost assistance available with preferred lender Wes Flowers, Southern Trust. Also see something you would love to have but it’s not here. Contact me and my builder will have his design team work on it. He is easy going and ready to make your new home all about you!!! You wont find another build of this quality at this amazing price.

343 Ewell Lane, South Chesapeake

$299,900

3 Beds ⋅ 3 Baths ⋅ 10646337 MLS

Welcome to this beautifully renovated 3 bedroom, 3 bath home in Historic South Norfolk! Taken down to the studs and rebuilt with quality craftsmanship, this home offers the feel of new construction without the new construction price tag. This fully permitted renovation includes a new roof, windows, HVAC, plumbing, electrical, insulation, drywall, flooring, kitchen, bathrooms, siding, decks, and more. Enjoy the inviting covered front porch and open-concept living room and kitchen featuring granite countertops, soft-close cabinetry, and stainless-steel appliances. The first floor offers a bedroom, full bathroom, and laundry room. Upstairs, you'll find two private suites, including a spacious primary suite with a walk-in closet and private bath featuring a dual-sink vanity. A versatile bonus room is perfect for a home office or nursery. Conveniently located near the new municipal center, public library, Lakeside Park, the Jordan Bridge, Elizabeth River, shopping, dining, military bases, and interstate access. This home is a must-see!

1324 22nd Street, Central Chesapeake

$649,900

4 Beds ⋅ 3.1 Baths ⋅ 10646358 MLS

STUNNING EXECUTIVE SMART HOME IN PREMIER RIVERFRONT COMMUNITY W/ NATURE PRESERVE! DESIGNED FOR BOTH COMFORT & EFFICIENCY, THE CRAFTSMAN STYLE HOME W/ FF PRIMARY BEDROOM & UPGRADES GALORE! Coastal themed Craftsman Style Luxury home w/ a charming wrap around front porch. Elegant Home w/ an open concept & comfortable open living spaces w/ 8 ft doors, high ceilings + Beautifully appointed WOOD FLOORING. Culinary Kitchen features extended island, Granite Counter tops, Bar Seating. Sprinkler system &well. (see add list of upgrades). Includes PREMIUM ION SOLAR PANELS (2023) to be paid in FULL by the seller @ closing! Approx. $33/month in income generated through SREC (Solar Panel Renewable Energy Certifications). Owners monthly electric bills are approx. $33/month. Carefree amenities; Waterfront Gazebo on deep water, Kayak Launch, Clubhouse w/ pool.... Green Spaces & winding trails throughout. WELCOME HOME!

224 Wildlife Trace, South Chesapeake

$399,900

3 Beds ⋅ 2.1 Baths ⋅ 10646281 MLS

Seller will pay up to $12,000 for closing cost assistance or to be used at buyer's discretion using our preferred lender and our attorney. Stunning New Construction! Welcome to this beautiful 3-bedroom, 2.5-bath home offering a modern living space. Designed with a spacious open floor plan, it's perfect for entertaining and everyday family living. Inside, the kitchen shines with soft-close cabinets, granite countertops. Bathrooms are also appointed with granite countertops and soft-close cabinetry for a cohesive, upscale look. Throughout the home, you'll find a blend of durable LVP flooring and plush carpet. Tray ceiling in the primary bedroom and walk in closet. This home features a 1-car garage. This brand-new home is the perfect blend of comfort, style, and convenience-don't miss your chance to own it in the heart of Chesapeake!

905 Railroad Avenue, Central Chesapeake

$609,700

4 Beds ⋅ 2 Baths ⋅ 10646302 MLS

Beautifully maintained all-brick transitional corner lot in Great Bridge. 4 bedroom/2 bath. 1st floor MB with en suite. Open floor plan with huge kitchen and stainless steel appliances, breakfast area. Wood-burning fireplace for cozy evenings. Walk out of family room door onto a TREX deck and large backyard. Award winning Cheshire Forest community. Amenities include clubhouse, pool, tennis/pickleball court, parks and playground. Shed sold as-is.

746 Yorkshire 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.