Chesapeake VA County Real Estate

Welcome to Chesapeake, Virginia—a vibrant city where the charm of Southern hospitality meets the convenience of modern living. Nestled in the heart of Hampton Roads, Chesapeake is the second-largest city in Virginia and boasts a rich tapestry of history, culture, and natural beauty.

With its unique blend of urban and rural landscapes, Chesapeake is home to an array of parks, waterways, and wildlife sanctuaries. The city features over 22,000 acres of open space, including the stunning Great Dismal Swamp National Wildlife Refuge, perfect for hiking, birdwatching, and enjoying the great outdoors. The picturesque waterways also provide ample opportunities for boating, fishing, and kayaking, making it a haven for nature enthusiasts.

Chesapeake’s diverse neighborhoods cater to a variety of lifestyles, from family-friendly suburbs to vibrant urban areas. The city offers excellent schools, making it an ideal place for families looking to settle down. Additionally, the thriving local economy, bolstered by industries such as defense, transportation, and agriculture, provides ample job opportunities.

Culturally, Chesapeake is rich with local events, festivals, and farmers' markets that foster a strong sense of community. Explore the historic Great Bridge area, or enjoy the arts and dining scene in the city’s bustling districts.

Whether you’re looking to buy your first home, invest in property, or simply explore the area, Chesapeake, VA, is a place where you can truly feel at home. Embrace the charm and convenience of this remarkable city—your new adventure awaits!

Newest Listings in Chesapeake VA County

$399,900

3 Beds ⋅ 2.1 Baths ⋅ 10658090 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 1,654 square feet of modern living space. Designed with a spacious open floor plan, it's perfect for entertaining and everyday 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

$380,000

3 Beds ⋅ 1.1 Baths ⋅ 10657429 MLS

Opportunity awaits in the desirable Western Branch area of Chesapeake! This 3-bedroom, 1.5-bath home is full of potential and ready for its next chapter. With solid bones and a little TLC, this property offers a wonderful opportunity to make it your own. The spacious family room leads to an impressive four-season room, providing additional space to relax, entertain, or simply enjoy the backyard views year-round. Situated on a generously sized lot, there's plenty of room to create your own outdoor retreat. Conveniently located near shopping, dining, and everyday amenities. Schools include Edwin W. Chittum Elementary, Jolliff Middle, and Western Branch High. Whether you're looking for a home to personalize or your next investment opportunity, bring your vision and discover the possibilities this property has to offer!

1805 Dockwood Trail, West Chesapeake

$554,900

4 Beds ⋅ 2.1 Baths ⋅ 10657893 MLS

Introducing The Evergreen by Wirth Living! Designed with comfort, style, and functionality in mind, The Evergreen offers a thoughtfully crafted two-story layout with spacious living areas and room for all. Featuring an open-concept great room and kitchen, a dedicated dining area, a private primary suite with two walk in closets, and a bonus bedroom upstairs with an option to add another full bathroom, this home blends everyday convenience with inviting spaces to gather and grow. A beautiful balance of modern living and timeless design, The Evergreen is ready to inspire your next chapter. The Estates at Jolliff Landing will be a charming neighborhood boasting single-family homes with covered porches, lush gathering spaces, an assortment of yard games, a playground, water features, a sports field, bike paths, a community center, a swimming pool, and a tree-lined sidewalks. Builder is offering partial CCA & $15,000 buyer incentive (see listing agent for details) when using one of our preferred lenders. Come visit our model home open daily from 12-5pm at 5023 Annapolis Drive.

MM Evergreen, West Chesapeake

$798,900

4 Beds ⋅ 3 Baths ⋅ 10657878 MLS

Pristinely kept home on over 3 Acres located in the highly sought-after Hickory School District! This move-in-ready home has been meticulously cared for with major system upgrades including a 3- year old roof, all new siding, a rebuilt HVAC package unit with all new components, two water heaters, a whole-house generator and updated windows and gutters! The renovated kitchen (2017), main room refinished hardwood and recently updated Primary bedroom set this home apart! Enjoy outdoor living on the Trex decking and rest easy knowing the septic system was cleaned and pumped in January 2026. With extensive updates, exceptional maintenance, and a prime location in the Hickory area of Chesapeake, this home offers the perfect combination of comfort, efficiency, and long-term value with land to go with it! Come see your new home today!

2020 Sanderson Road, South Chesapeake

$299,900

3 Beds ⋅ 2.1 Baths ⋅ 10657730 MLS

Enjoy low-maintenance luxury at Estella Villas! This beautifully kept townhome makes daily life simple with hard-surface flooring throughout the first floor and cozy carpet upstairs. The open-concept floor plan is perfect for hosting guests and spending time with family. A welcoming foyer upon entry sets this property apart from many modern builds. The home features high ceilings, and the kitchen overlooks the great room. On weekends, enjoy a barbecue on your private patio and embrace simple living without the stress of tedious yard work. Large bedrooms, granite countertops, master bedroom with en suite bathroom, double vanity sink, and walk-in closet. Conveniently located 12 minutes or less from downtown Norfolk, Greenbrier Mall. This one is stunning and upscale. Schedule your showing today!

216 Astra Lane, Central Chesapeake

2035 Christian Avenue, Central Chesapeake

$310,000

3 Beds ⋅ 2.1 Baths ⋅ 10657931 MLS

Discover the perfect place to call home in this inviting 3 bedroom, 2.1 bathroom home! Featuring an open concept layout great for everyday living and entertaining, spacious closets for all your storage needs, and a fenced backyard great for outdoor enjoyment, this home offers comfort and convenience. Enjoy a convenient location near a variety of amenities, shopping, dining, and recreational activities. Whether you're looking for a place to relax or entertain, this home is ready for its next chapter with you!Don’t miss your opportunity to make it yours today!

2035 Christian Avenue, Central Chesapeake

$615,000

4 Beds ⋅ 2.1 Baths ⋅ 10658008 MLS

This inviting home offers 4 bedrooms, 2.5 baths, and approximately 2,568 square feet of living space, providing room to relax, entertain, and enjoy everyday living. Major exterior features include a newer roof and a gutter guard system for added convenience and reduced maintenance. Need extra storage or a dedicated workspace? The shed with electricity offers added versatility for hobbies, projects, or storage. Permanent attic stairs lead to a floored area for lots of storage! Located in the sought-after Etheridge Lakes area and served by sought-after Chesapeake schools, this home offers a wonderful combination of space, practical features, and location. Don't miss the opportunity to make this home your own. Schedule your private showing today!

808 Dolph Circle, South Chesapeake

10658012 MLS

Commercial office space available immediately in a great location! This 150-square-foot office offers access to common areas and a bathroom, with all utilities included in the monthly rent of $1,200. Ideal for a small business, professional, consultant, service provider looking for a convenient and comfortable workspace. Rent includes a waiting area with receptionist on site. Contact us today for more information or to schedule a viewing!

4536 Bruce Road Unit 2, West Chesapeake

$383,500

4 Beds ⋅ 2 Baths ⋅ 10657925 MLS

This property has been thoughtfully updated from top to bottom, offering modern finishes and peace of mind for its next owner. Improvements include a new roof, HVAC system, water heater, fully updated kitchen and bathrooms, new outlets and switches, doors, flooring, and stylish light fixtures, plus much more. Fresh interior and exterior paint give the home a clean, bright, and refreshed look. With numerous upgrades throughout, this property is ready for you to move in and make it your own. Don’t miss the opportunity to own this beautifully refreshed home!

2941 Guenevere Drive, South Chesapeake

$589,000

4 Beds ⋅ 2.1 Baths ⋅ 10657970 MLS

Welcome home to Hickory Manor! This crisp, and move-in ready 4-bedroom, 2.5 bath, 2456 sqft property sits in the highly desirable Hickory school district delivering space, comfort, and community amenities buyers love. The inviting foyer entry leads into an open, light-filled main level featuring an inviting living room, spacious dining area, modern kitchen with pantry, and mudroom ideal for entertaining. Upstairs offers all four bedrooms, including a generous primary suite with a custom walk-in closet system and convenient second floor laundry. The fenced backyard provides a ideal outdoor retreat. Located in the amenity-rich Hickory Manor community with access to the clubhouse, pool, fitness center, and playground. With paid off Solar Panels and a transferable warranty, your dream home awaits offering long-term energy savings and peace of mind. Seller is offering closing cost assistance, making this an exceptional value you won't want to miss!

614 Middleton Way, South Chesapeake

$639,900

4 Beds ⋅ 2.1 Baths ⋅ 10658002 MLS

Welcome to 660 Middleton Way! This well-maintained 4-bedroom, 2.5-bath home features a stunning backyard oasis with a private swim spa, covered patio, and extended concrete slab, great for relaxing and entertainment. Inside, enjoy a primary suite with an ensuite bathroom featuring double sinks, plus convenient upstairs laundry. A storage shed provides extra space for outdoor equipment. Community amenities include a clubhouse, grounds maintenance, pool, gym, and trash pickup. Conveniently located near shopping, dining, and major interstate access. Schedule your showing today!

660 Middleton Way, South Chesapeake

10657975 MLS

Commercial office space available immediately in a great location! This 150-square-foot office offers access to common areas and a bathroom, with all utilities included in the monthly rent of $1,200. Great for a small business, professional, consultant, service provider looking for a convenient and comfortable workspace. Rent includes a waiting area with receptionist on site. Contact us today for more information or to schedule a viewing!

4536 Bruce Road Unit 1, West Chesapeake

Start Your Search

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.