Chesapeake VA County Real Estate

Welcome to Chesapeake, Virginia – a vibrant city that beautifully blends the charm of suburban living with the excitement of urban amenities. Nestled in the heart of South Hampton Roads, Chesapeake is known for its lush landscapes, rich history, and a wide array of recreational opportunities, making it an ideal place for families, professionals, and retirees alike.

Chesapeake is the second-largest city in Virginia, boasting over 350 miles of navigable waterways, including the stunning Chesapeake Bay. Residents enjoy a plethora of outdoor activities, from fishing and boating to hiking and biking along the scenic trails of Great Dismal Swamp National Wildlife Refuge. The city is also home to numerous parks and playgrounds, providing ample space for family outings and community events.

Culturally rich, Chesapeake offers a variety of attractions, including the Chesapeake Planetarium and the historic Great Bridge Battlefield. The city hosts several annual events, such as the Chesapeake Jubilee and the Blackwater History Museum's events, which celebrate the local heritage and foster a sense of community.

For those who appreciate a thriving economy, Chesapeake is strategically located near major highways and military installations, making it a hub for both commerce and defense. With a diverse range of housing options, from charming single-family homes to modern apartments, there’s something for everyone in this welcoming city.

Whether you’re drawn by the natural beauty, the friendly neighborhoods, or the vibrant local culture, Chesapeake, VA, is a place where you can truly feel at home. Come explore all that this remarkable city has to offer!

Newest Listings in Chesapeake VA County

$325,000

10650830 MLS

Great opportunity on 11.811 acres of cleared land in southern Chesapeake. This is a flag lot and comes with 25' of road frontage going south to the remaining 11.3 acres of cleared crop land. The bulk of this lot is located approx. 800 feet off the paved city road and will allow for a relaxed setting for that custom homesite you have been wanting. Sit on the back porch and watch the sun set while enjoying the expansive view across almost 600 acres of open crop land. Hickory school district and just minutes from the 168 bypass. Convenient to all of Hampton Roads and Chesapeake Genera Hospital. Zoned A1 presently. Sale subject to existing farm lease.

11.8 Acres Ballahck Road, South Chesapeake

$410,000

4 Beds ⋅ 2 Baths ⋅ 10650554 MLS

Back on market pending release through no fault of seller—creating an exciting second opportunity to own this beautifully maintained home in highly sought-after Great Bridge! Welcome to this charming 4-bedroom,2-bath ranch nestled in an established Chesapeake neighborhood filled with mature trees,beautiful homes,& pride of ownership throughout. Offering the ease of one-level living,this move-in-ready home delivers the perfect blend of comfort,charm,& functionality in one of Great Bridge’s most desirable locations. Step inside to bright,inviting living spaces filled with natural light and designed for comfortable everyday living & effortless entertaining. This is the kind of home where holidays feel cozy,weekend gatherings come naturally,& everyday moments feel just a little sweeter. The thoughtful floor plan offers generous room sizes,a family-friendly layout,& abundant storage,giving everyone space to live,work,& unwind comfortably. Outside,the oversized backyard creates endless possibilities for backyard barbecues,kids at play,gardening,firepit nights,or simply relaxing after a long day. Whether hosting family celebrations or enjoying peaceful mornings with coffee outdoors,this outdoor space offers the lifestyle so many buyers are searching for. In a world where so many are craving more peace,more space,& more connection,this home delivers all three. Located near top-rated Great Bridge schools,shopping,dining,parks,& convenient interstate access,this Chesapeake home for sale offers the rare combination of location,space,& lifestyle. Ranch homes with large yards,one-level living,& this much charm in Great Bridge rarely become available. More than just a house,this is a place to slow down,spread out,& truly feel at home.

2728 Blacksmith Trail, South Chesapeake

$700,000

5 Beds ⋅ 3 Baths ⋅ 10650782 MLS

RAISE YOUR EXPECTATIONS! Come home to a MOVE-IN READY 5 Bedroom, 3 Full Bath beauty featuring an OPEN FLOOR PLAN, natural light & EXTRAS galore! Enjoy the GREAT ROOM with Gas Fireplace, open Dining Room and Kitchen with Granite, Stainless Appliances, full-sized Island, Breakfast Bar, loads of cabinets + two Pantries! The FIRST-FLOOR BEDROOM with Full Bath just steps away offers In-law or Multi-generational options. The delightful PRIMARY SUITE features 2 Walk-in Closets and lavish Bath with separate Tub & Shower. There's a WALK-IN ATTIC & tons of storage too! High-end upgrades include newer Composite Siding & Tankless Water Heater. VACATION AT HOME! Awesome SCREENED PORCH, manicured FENCED YARD, Hot Tub & Garden spaces await. Irrigation + 2 Sheds add even more! You'll love the 2-CAR GARAGE, Great Bridge Schools & TERRIFIC LOCATION near shopping, dining and expressways. Comfort, versatility, function and FUN all team up beautifully! Stop Looking for a House . . . Come Find It!

1125 George Olah Drive, South Chesapeake

$649,990

4 Beds ⋅ 2.1 Baths ⋅ 10650930 MLS

Come see why families are calling Patriots Ridge home! The Columbia single-family home is just as inviting as it is functional. Discover a magnificently spacious floor plan with custom flex areas. The welcoming family room effortlessly flows into the gourmet kitchen and dining area, so you never miss a moment. Add a covered porch for those warm summer nights and use the family entry to control clutter. On the second floor, 4 large bedrooms await, with the option to change one to a cozy loft for more living and entertaining space. Your luxurious owner's suite offers a large closet and spa-like double vanity bath. Come home to The Columbia today.

1524 Jimmy Lane, South Chesapeake

$465,000

4 Beds ⋅ 2 Baths ⋅ 10650919 MLS

Looking for a lovingly maintained brick ranch where care is evident inside & out? This pristine 4-bedroom, 2-bath ranch blends timeless character with thoughtful updates & an open, functional layout. Feel the difference of real hardwood floors underfoot as you explore room to room. Recessed lighting, granite counters, a gas fireplace & new dishwasher add style & comfort. Storage? An expansive walk-in attic runs the full length of the house. Outside, professional landscaping & meticulous grounds reflect true pride of ownership. Improvements are too numerous to list, but highlights include replacement windows & siding, extensive vinyl & aluminum exterior wrapping, and seamless gutters with guards. And under the house? A new dehumidifier helps keep the crawl space crisp, clean & dry, with an annual termite contract in place. With Deep Creek continuing to grow & evolve, this is your chance to own an exceptional value, something long-lasting, well cared for & truly special!

3405 Parr Lane, South Chesapeake

$754,990

6 Beds ⋅ 4 Baths ⋅ 10650921 MLS

Homesite special just listed! Welcome to Patriots Ridge! New homes in Chesapeake's Hickory HS district. Amenity-filled community 5 mins to Edinburgh shopping w/ quick access to Military and 168, 64 & 664. The Seneca single-family home exudes style and substance. Beyond the foyer, the versatile flex area sets the tone as a library, office or guest suite. Serve dinner in the functional dining room, or the gourmet kitchen and dining space, which flow effortlessly into the wide open family room. Add a covered porch for outdoor living!

208 Tinker Street, South Chesapeake

$700,000

6 Beds ⋅ 3 Baths ⋅ 10650902 MLS

909 Sydenham Welcome to this spacious 6-bedroom home on a desirable corner lot, offering plenty of room to spread out and enjoy all that this home has to offer. With one bedroom conveniently located downstairs, the layout provides flexibility for guests, a home office, or multigenerational living.Step outside and enjoy your private pool—perfect for summer days, entertaining, and making memories at home. Recent updates provide added peace of mind, including a 2021 roof and a 2023 pool liner and pool heater.With five bedrooms, a corner-lot setting, and a pool, 909 Sydenham offers the space, flexibility, and outdoor living you’ve been looking for. Come see all this home has to offer!

909 Sydenham Boulevard, South Chesapeake

$615,000

5 Beds ⋅ 3 Baths ⋅ 10650705 MLS

Welcome to 1010 Cuervo Court, a spacious 5-bedroom, 3-bath home offering approximately 3,000 sq ft in sought-after Las Gaviotas! Flexible floor plan includes a first-floor bedroom and full bath, formal living room and a separate dining room. The large family room features cathedral ceilings, a stunning floor-to-ceiling brick fireplace, abundant natural light, and golf course views. Spacious primary suite offers a private balcony, large walk-in closet, and spa-like bath with dual vanities, jetted tub, and separate shower. Generously sized bedrooms, excellent closet space throughout, and a finished room over the garage provide plenty of space and flexibility. Additional features include a second level laundry room, side-loading 2-car garage, newer carpet, and fresh paint in select rooms. Enjoy the charm of this established Chesapeake community with beautiful streets, golf course surroundings, walking trails, and highly regarded schools.

1010 Cuervo Court, South Chesapeake

$379,999

4 Beds ⋅ 2 Baths ⋅ 10650851 MLS

Nestled in Chesapeake’s established Camelot neighborhood, this beautifully updated vinyl and brick ranch offers 4 bedrooms, 2 full baths, and 1,762 square feet of comfortable single-level living. Luxury vinyl plank flooring flows throughout the main living areas, while the freestanding wood-burning stove creates a warm focal point for gathering. The kitchen features an oversized island, abundant workspace, and opens to a dedicated laundry/mudroom. Spacious bedrooms, updated finishes, and a functional layout make this home truly move-in ready. Step outside to a privacy fenced backyard on an approximately 72’ x 101’ lot with room to entertain, garden, or unwind beneath mature shade trees. Ideally located near Camelot Elementary and Camelot Park with quick access to George Washington Hwy (US-17), Indian River Rd to I-64, and Military Hwy to I-264 for easy commuting throughout Hampton Roads.

832 Parapet Road, South Chesapeake

$375,000

3 Beds ⋅ 2 Baths ⋅ 10650654 MLS

Welcome home to this charming ranch offering plenty of space to spread out and enjoy! Inside, you’ll find a formal living room and dining room, along with a cozy living area featuring a wood-burning fireplace. The kitchen offers new flooring and opens to a breakfast nook with convenient backyard access. Just off the back of the home is a versatile bonus room, currently used as a playroom, that would also make a great sunroom, home office, or flex space. The primary bedroom features a private bath and two closets, and both bathrooms feature new flooring. Step outside from either the breakfast nook or bonus room to a fully fenced, private backyard complete with a storage shed, playset, cozy patio, and firepit area, patio for entertaining or relaxing outdoors. A comfortable floor plan with flexible spaces inside and a backyard ready to enjoy!

805 Helmsdale Way, South Chesapeake

$379,000

4 Beds ⋅ 2 Baths ⋅ 10650746 MLS

Welcome home to this fully remodeled 4-bedroom, 2-bath residence, thoughtfully updated with modern finishes. The spacious floor plan offers abundant living space for both everyday living and entertaining. The gourmet kitchen is a chef's dream, featuring stylish finishes and ample workspace. Relax in the private primary suite, complete with large walk in his-and-hers closets and a luxurious feel. Outside, enjoy a generously sized backyard with plenty of room for gatherings, play, or future outdoor enhancements. This move-in-ready home combines comfort, style, and lasting value.

1109 Santeetlah Avenue, Central Chesapeake

$305,000

3 Beds ⋅ 1.1 Baths ⋅ 10650769 MLS

Single family two-story detached home located in the Norfolk Highlands section of Chesapeake. 3 bedrooms, 1.5 bathrooms. Spacious layout with a bedroom and half bathroom on the second floor. Many updates completed in 2021. First floor laundry. Large lot with huge fenced in backyard with an oversized shed. Seller has clear termite and moisture letter in hand.

1605 Laurel Avenue, Central 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.