Chesapeake Real Estate

Welcome to Chesapeake, Virginia – a vibrant city that beautifully blends history, nature, and modern living. Nestled in the heart of Hampton Roads, Chesapeake is not just a place to call home; it’s a lifestyle enriched by its diverse offerings and welcoming community.

Chesapeake boasts an impressive array of parks and waterways, perfect for outdoor enthusiasts. With over 22,000 acres of parks and natural reserves, you can explore scenic trails, enjoy picnics by the water, or embark on kayaking adventures along the numerous rivers and lakes. The Great Dismal Swamp National Wildlife Refuge, a unique ecosystem, is just a stone's throw away, providing a serene escape for nature lovers and birdwatchers alike.

The city is also steeped in history, with charming neighborhoods that reflect its rich past. From the historic Great Bridge area to the quaint streets of Deep Creek, Chesapeake offers a variety of architectural styles that tell the story of its development. The city’s commitment to preserving its heritage is evident in its numerous historic sites and community events.

For families, Chesapeake is an ideal place to settle down. The city is home to highly-rated schools, family-friendly activities, and a strong sense of community. With a range of shopping, dining, and entertainment options, including local farmer's markets and annual festivals, there’s always something happening in Chesapeake.

Whether you’re looking for a bustling suburban lifestyle or a peaceful retreat, Chesapeake, VA, has it all. Come and discover the charm and warmth that make this city a wonderful place to live, work, and play!

Newest Listings in Chesapeake

$625,000

4 Beds ⋅ 2.1 Baths ⋅ 10647389 MLS

MUST SEE 4 BR, 2.5 BATH HOME IN SOUGHT AFTER ETHERIDGE LAKES NEIGHBORHOOD. HOME SITS ON A LGE FENCED YARD, W/2CAR GARAGE AND PLENTY OF DRIVEWAY SPACE. KIT UPDATES INCLUDE TOP OF THE LINE SS APPLIANCES, INDUCTION STOVE, NEW FLOORING & PAINT. LGE PBR WITH SITTING/FLEX RM, ENSUITE BATH HAS BIG CLOSET, DOUBLE SINKS, JETTED TUB & STANDUP SHOWER. NICE SIZE BR'S, ALOT OF STORAGE INCLUDING A WALK-IN AREA BEHIND BED IN PBR. SUNRM ADDED IN '22, WINDOWS '21, ROOF '20, HVAC '19, HTWTR TANK '23. CHECK OUT THE HIGHLY RATED SCHOOLS. HOUSE KEPT UNDER TERMITE/MOISTURE CONTRACT. TAKE A LOOK, YOU WILL LIKE WHAT YOU SEE. QUICK CLOSING

1805 Crestwynd Drive, Chesapeake

$208,000

3 Beds ⋅ 1 Baths ⋅ 10647527 MLS

Brick ranch home with 3 bedrooms, 1 bath. Living room and dining room adjacent to kitchen. Convenient to interstates, shopping, entertainment and schools. Rooms are nicely sized and you have great sunlight throughout. 1 car attached garage, large yard.

1140 Woodland Terrace Drive, Chesapeake

$350,000

3 Beds ⋅ 2 Baths ⋅ 10647247 MLS

Welcome to this beautifully updated 3-bedroom, 2-bathroom ranch home Western Branch. With an open floor plan that creates a seamless flow between living and dining spaces, this home is perfect for both relaxing and entertaining. The modern kitchen features stainless steel appliances, granite countertops, and lots of countertop space, making meal prep a breeze. Enjoy BBQs and family fun in a large, fully fenced backyard with a wood privacy fence. Conveniently located just minutes from shopping, schools, and parks, this home offers both comfort and convenience. Don’t miss the opportunity to make it yours!

3108 Bomar Dr Drive, Chesapeake

$7,900

10647463 MLS

Vacant Land in Hillcrest subdivision. Zoned for great schools! Drive by anytime. Seller has never occupied the land, has no information to share. Buyer to perform all due diligence.

14 Blk Tuck Street, Chesapeake

$315,000

3 Beds ⋅ 2.1 Baths ⋅ 10647260 MLS

Welcome home to this beautifully maintained 3-bedroom, 2.5 bath townhome offering over 1,600 square feet of comfortable living space—and no HOA! Pride of ownership shines throughout this move-in-ready home featuring an upstairs laundry for added convenience and a security system that's already wired and ready for activation. Major updates provide peace of mind, including a new roof (2016), kitchen appliances and refrigerator (2021), washer and dryer (2023), and water heater (2026). Whether you're a first-time buyer, downsizing, or looking for an investment opportunity, this well-cared-for home offers the perfect combination of comfort, value, and convenience.

703 Hunters Quay, Chesapeake

$845,000

5 Beds ⋅ 4.1 Baths ⋅ 10647443 MLS

The Macon Multi-Gen at Riverview Landing - Master Model Listing by Wetherington Homes. Buyers may select their lot and personalize available design options. Thoughtfully designed with approximately 3,535 sq. ft. of living space and a 3-car garage, the MM Macon Multi-Gen offers exceptional flexibility for today’s lifestyles. This home features a private multi-generational suite complete with a living room, bedroom, full bath, and washer/dryer hookup, with an optional kitchenette for added convenience. Ideal for extended stays, guests, or multi-generational living. Enjoy a convenient location close to schools, shopping, restaurants, and more! Contact our Sales Counselor today to learn more.

MM Macon-Multi-Gen, Chesapeake

$922,500

5 Beds ⋅ 4 Baths ⋅ 10647253 MLS

Exceptional all-brick custom home nestled in the heart of Great Bridge, meticulously maintained and thoughtfully designed with a floor plan you’re sure to love. Offering 5 spacious bedrooms and 4 full bathrooms, this home also features a versatile first-floor flex room with adjacent full bath ideal as a 6th bedroom, home office, playroom, or guest suite. The private, beautifully landscaped backyard creates the perfect retreat, complete with a patio and full-yard irrigation system. Built as the builder’s personal residence, the home showcases quality craftsmanship and upscale details throughout, including extensive custom trim work and abundant storage. Additional highlights include a garage loft with extra storage space, dual heat pump/HVAC systems for comfort and efficiency, a large walk-in closet, oversized pantry, generous laundry room, and spacious secondary bedrooms. A rare opportunity to Buy a truly well-crafted custom home in one of Great Bridge’s most desirable locations.

138 Greengable Way, Chesapeake

$359,000

4 Beds ⋅ 2 Baths ⋅ 10647418 MLS

Fully updated, move-in ready 4bed/2bath home. Step inside to new LVP flooring, new carpet, new lighting fixtures, and fresh paint throughout. The spacious eat-in kitchen features new soft-close shaker cabinets, granite countertops, S/S appliances, and plenty of storage. Enjoy a convenient 1st floor primary suite w/ a large walk-in closet and a beautifully updated ensuite featuring a new double vanity and custom tiled shower. New roof '26, HVAC and water heater apprx '21. Conveniently located near interstates, shopping outlets, dining, schools, and military bases.

1050 Wingfield Avenue, Chesapeake

$425,000

3 Beds ⋅ 2.1 Baths ⋅ 10646703 MLS

Welcome home to this beautifully maintained 3 bedroom, 2.5 bath home featuring an open-concept layout with soaring ceilings and a versatile loft. Luxury vinyl plank flooring flows throughout the first floor, creating a stylish and low-maintenance living space. The spacious primary suite offers a private en suite bath, while generously sized secondary bedrooms provide flexibility for a variety of needs. Enjoy the convenience of a two-car garage and a fully fenced backyard - perfect for outdoor entertaining, pets, or play. Energy-efficient solar panels help reduce monthly electric costs. Ideally situated with easy access to shopping, dining, major highways, military bases, and everyday conveniences. Plus, receive 1% toward closing costs when using preferred lender. Don't miss this exceptional opportunity!

711 Pile Avenue, Chesapeake

$319,900

3 Beds ⋅ 2 Baths ⋅ 10647403 MLS

Come see this recently renovated 3-bedroom, 2-full bath ranch with an open floor plan and fully updated interior! This home features a beautifully updated eat-in kitchen with all new stainless appliances, new granite countertops and new cabinets! Primary bedroom with primary bath! New flooring to include carpet and laminate! Fresh paint throughout! Updated fixtures! Updated baths! 1-car detached garage! Don't miss this one! Property has been staged and staging items do not convey.

2912 Scotia Drive, Chesapeake

$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

$675,000

5 Beds ⋅ 3 Baths ⋅ 10647378 MLS

Meticulously maintained 5-bedroom, 3-bath home in sought-after Las Gaviotas offering over 3,000 sq ft of bright, open living space with water views. Flexible layout includes 1st floor bedroom and bath, huge FROG can be bedroom, office, flex space. 2 Bathrooms feature updated Onyx showers for a modern touch. Enjoy a private, wooded backyard overlooking the canal—perfect for relaxing or entertaining. Ample storage throughout. A whole-house generator provides peace of mind, and no flood insurance is required. Community includes a pool, clubhouse, and golf - pool and golf have optional membership. Don’t miss this exceptional cul-de-sac opportunity!

504 Aguila Court, 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.