Chesapeake VA County Real Estate

Welcome to Chesapeake, Virginia – a charming city that beautifully blends urban sophistication with serene suburban living. Nestled in the heart of Hampton Roads, Chesapeake is known for its rich history, vibrant culture, and stunning natural landscapes. With over 350 miles of navigable waterways, this city is a paradise for boating enthusiasts and nature lovers alike.

Chesapeake boasts a diverse community, offering an array of neighborhoods that cater to all lifestyles. From the bustling, family-friendly areas of Great Bridge to the serene, picturesque settings of Deep Creek, there’s something for everyone. The city is home to top-rated schools, making it an ideal location for families seeking quality education for their children.

Outdoor enthusiasts will find plenty to love in Chesapeake. The city is dotted with beautiful parks, nature reserves, and trails, including the expansive Great Dismal Swamp National Wildlife Refuge, where you can explore the lush landscapes and spot various wildlife. For those who enjoy shopping and dining, the Greenbrier area offers a vibrant selection of shops, restaurants, and entertainment options.

Chesapeake is also conveniently located near major highways, making it easy to commute to nearby cities like Norfolk and Virginia Beach. Whether you’re looking for a cozy single-family home, a modern townhouse, or a spacious waterfront property, Chesapeake has a diverse real estate market that can accommodate your needs.

Experience the warmth and charm of Chesapeake, where every day feels like a getaway. Come explore this hidden gem in Virginia and discover your dream home in a community that truly feels like family!

Newest Listings in Chesapeake VA County

$734,900

5 Beds ⋅ 3 Baths ⋅ 10646525 MLS

There is not enough space to explain how wonderful this home is! A rare sense of privacy meets thoughtful luxury in this upgraded 2022 Grassfield home. Near the end of a cul-de-sac and bordered by protected wetlands and unbuildable parcels on both sides, the lot offers a wooded backdrop that is hard to replicate. The flexible 5-bedroom, 3-bath layout includes two primary suites, one on the first floor, PLUS an office/flex room AND loft-style second living area. Crown molding, hardwood stairs, custom window treatments, a gas fireplace, quartz countertops, stainless appliances, gas cooking, under-cabinet lighting, upstairs laundry, walk-in attic, tankless water heater, smart garage opener, security system, and a custom 36-foot patio add comfort and refinement. Trusted lender Steve Hawley, NMLS #1813927, with Southern Trust Mortgage, NMLS #2921, will provide a 1% lender-paid buydown on this listing. Ask the listing agent for details. Subject to borrower qualification and lender approval.

1741 Watershed Court, South Chesapeake

$530,000

3 Beds ⋅ 2 Baths ⋅ 10646578 MLS

Beautiful move in ready home in an established neighborhood. Lots of recent upgrades - hardwood floors, countertops, HVAC, Water heater, and more! Perfect home for the 55 and up client - all one level, detached home, clubhouse, pool, water view from the back patio. Two car garage and so much more!

1417 Blairwood Lane, South Chesapeake

$210,000

2 Beds ⋅ 2 Baths ⋅ 10646633 MLS

3521 Sugar Run, West Chesapeake

$335,000

3 Beds ⋅ 2.1 Baths ⋅ 10646628 MLS

Easy living awaits in this 3-bedroom, 2.5-bath condo in the heart of Greenbrier. The living room is filled with natural light and offers a warm, inviting feel from the moment you walk in. The large kitchen features plenty of cabinet and counter space, a walk-in pantry, and opens to the dining area, making everyday living and entertaining easy. A first-floor bedroom adds flexibility and convenience. Enjoy the private fenced patio, great for morning coffee, grilling, or relaxing outdoors. Upstairs, the primary suite offers a large walk-in closet and attached bath with a soaking tub and separate shower. The second upstairs bedroom also features an attached full bath and walk-in closet. A second-floor laundry room with sink adds extra convenience. Community amenities include a pool, yard maintenance, trash pickup, sewer and water. Conveniently located near shopping, dining, interstates, and more. Seller is offering closing costs assistance with an acceptable offer.

1523 Pucknall Drive, South Chesapeake

$385,000

3 Beds ⋅ 2.1 Baths ⋅ 10646623 MLS

Step inside this inviting 3-bedroom Chesapeake home offering plenty of space both inside and out! The first floor welcomes you with a bright, open layout that brings the living, dining, and kitchen areas together, making the space great for everyday living and entertaining. The kitchen is equipped with abundant cabinetry, ample counter space, a large pantry, and a convenient breakfast bar. Laminate flooring flows throughout the main level, which also includes a half bath for guests.The second floor features two comfortable secondary bedrooms, a full hall bath, and a conveniently located laundry room. The spacious primary suite stands out with its walk-in closet and private en-suite bathroom. Out back, a fully fenced yard and patio provide the perfect setup for cookouts, gatherings, or relaxing outdoors. An attached one-car garage and oversized driveway offer additional parking and storage. All of this in a convenient Chesapeake location just minutes from Greenbrier?s shopping, restaurants, entertainment, and everyday essentials!

2130 Lockard Avenue, Central Chesapeake

$350,000

3 Beds ⋅ 2 Baths ⋅ 10646601 MLS

This beautiful updated brick ranch in the heart of Chesapeake checks all the boxes. Updated kitchen with lots of storage and space. Family room, and a living room to spread out, three bedrooms, two full bathrooms and a backyard built for entertaining. Don't miss out on this move in ready home.

533 Warren Avenue, South Chesapeake

$475,000

4 Beds ⋅ 2 Baths ⋅ 10646475 MLS

Fantastic opportunity to own this beautifully maintained 4-bedroom, 2.5-bath ranch in the desirable Etheridge Manor neighborhood. Situated on a spacious, deep lot, this single-family home has been meticulously cared for over the years. Inside, you'll find stunning hardwood floors, a welcoming fireplace, and a thoughtfully designed floor plan that's ideal for everyday living and entertaining. Recent updates include the HVAC system and water heater. The inviting front porch is the perfect place to relax, and the expansive backyard provides plenty of room for gardening, play, or entertaining. Conveniently located near shopping, dining, parks, and schools, this is a wonderful opportunity to own a fantastic home in an established neighborhood.

920 Bellingham Drive, South Chesapeake

$379,000

4 Beds ⋅ 2 Baths ⋅ 10646582 MLS

Welcome home to this charming 4-bedroom ranch in the desirable Western Branch area! Featuring beautifully refinished hardwood floors throughout the main living areas and new luxury vinyl plank flooring in the versatile fourth bedroom, this flexible space is perfect as a home office, playroom, or guest room. Outside, enjoy the spacious backyard and deck ideal for entertaining, relaxing, or family gatherings. Conveniently located just minutes from shopping, dining, schools, and easy interstate access, this home offers both comfort and convenience. Don’t miss your opportunity to make it yours!

2953 E Point Drive, West Chesapeake

$750,000

6 Beds ⋅ 3 Baths ⋅ 10646538 MLS

Spacious House with many gems. Master Bedroom has walk-in tub. Two sunrooms with 5 ft windows.Second level add on has two spacious rooms with extensive closet space and built in storage. Office/study. Family Room 15 x 15 . Two sunrooms. Kitchen has Island that seats six with built in storage beneath Detached garage with Apartment approximately 864 ft ready for occupancy. Carport, Storage barn with electricity 654ft. Hot tub for 6. Lots of space for lighting up the grill. Drive way willaccommodate several vehicles Many updates. Close to interstate 64, Military Bases, Hospital and Shopping.

245 Fernwood Farms Road, South Chesapeake

$265,000

3 Beds ⋅ 1 Baths ⋅ 10646551 MLS

This home has great bones. Waiting for the new owner to come in and make this home your very own. Home needs total renovation. Features 3 bedrooms, 1 bath, nice size family room. Corner lot. Property sold "As Is" "Where Is".

357 Gracie Road, Central Chesapeake

$995,000

6 Beds ⋅ 4 Baths ⋅ 10645935 MLS

An exceptional opportunity to own a Stephen Alexander custom home in Greystone, one of Chesapeake's premier luxury communities where homes are rarely available. This expansive executive residence blends timeless craftsmanship with the space, flexibility, and resort-style amenities today's luxury buyers seek. A first-floor bedroom with an adjacent full bath offers versatility for guests, a home office, or multi-generational living. The primary suite is a true retreat with a fireplace, sitting area, and four closets. Enjoy a private backyard oasis featuring an in-ground pool, hot tub, screened porch, gazebo, fire pit, privacy fence, irrigation well, and expanded parking for a boat or RV. Scenic walking paths enhance this sought- after community. Significant recent investments include a new roof (2026), three HVAC systems, an encapsulated crawl space, new hardwood flooring, updated bath vanities, freshly painted kitchen cabinetry, and a new oven. Schedule your private showing today!

821 Redleafe Circle, South Chesapeake

$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

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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.