Chesapeake VA County Homes for Sale

Welcome to Chesapeake, Virginia – a vibrant city that beautifully blends suburban charm with urban convenience. Nestled in the heart of Hampton Roads, Chesapeake boasts a rich history, scenic landscapes, and a welcoming community that makes it a sought-after destination for homebuyers. With its picturesque parks, winding waterways, and extensive outdoor recreational opportunities, Chesapeake is perfect for families, retirees, and anyone who enjoys an active lifestyle.

Chesapeake is renowned for its family-friendly atmosphere, top-rated schools, and diverse neighborhoods that cater to various lifestyles and budgets. From charming single-family homes in quiet cul-de-sacs to modern townhouses and spacious waterfront properties, the homes for sale in Chesapeake offer something for everyone. With a robust real estate market, prospective buyers can find a range of options that suit their needs, whether you’re looking for a cozy starter home or a luxurious estate.

The city is also conveniently located near major highways, providing easy access to Norfolk, Virginia Beach, and beyond. Enjoy the best of both worlds with a peaceful suburban setting while being just a short drive away from vibrant city life, shopping, dining, and entertainment.

As you explore the homes for sale in Chesapeake, you’ll discover a community rich in culture and camaraderie. With an array of local events, farmers' markets, and festivals, there’s always something happening here. Come and experience the warmth of Chesapeake – your dream home awaits!

Newest Chesapeake VA County Homes for Sale

$450,000

5 Beds ⋅ 3 Baths ⋅ 10658123 MLS

Welcome home to this spacious 5-bedroom, 3-full-bath home in Chesapeake, offering a wonderful combination of comfort, functionality, and convenience. Built in 2006, this home features a versatile floor plan with a first-floor bedroom and an accessible full bathroom, providing flexibility for guests and multigenerational living. Fresh carpet and paint throughout give the home a refreshed feel. The HVAC system was replaced in 2017. Outside you can enjoy the spacious, fully fenced backyard, featuring a double gate that allows vehicle access. Conveniently located near area military bases, this home offers an appealing location for military personnel, commuters, and anyone looking to enjoy all that Chesapeake has to offer!

1403 Elder Avenue, Central Chesapeake

$355,000

4 Beds ⋅ 2 Baths ⋅ 10658131 MLS

Tucked away on a peaceful cul-de-sac, this charming Chesapeake property welcomes you with exceptional features and inviting style. Inside, the home boasts premium, eco-friendly bamboo flooring across most of the living areas, creating a clean, modern ambiance. A standout highlight is the unique two-section screened porch, carefully crafted for year-round enjoyment, morning coffees, or evening gatherings. The private backyard extends your living space with endless opportunities to relax, garden, or host loved ones. Situated moments from premier shopping, dining, and major commuter routes, this flexible home is ready for its next chapter.

700 Saxon Court, South Chesapeake

1125 Sir Gawaine Drive, South Chesapeake

$360,000

4 Beds ⋅ 2.1 Baths ⋅ 10658020 MLS

Welcome home to this charming Chesapeake property offering comfort, functionality, and space to grow. Enjoy peaceful mornings and quiet evenings from the charming covered porch, an ideal extension of the home's living space. This traditional home features a fenced backyard ideal for entertaining, pets, or play, along with a patio for relaxing evenings outdoors. Inside, you'll find thoughtful living spaces including a breakfast area, pantry, utility room, and a converted garage that provides flexibility for a home office, playroom, guest space, or hobby room. Located in an established neighborhood with easy access to shopping, dining, and major commuter routes. Don't miss your chance to make this Chesapeake home your own!

1125 Sir Gawaine Drive, South Chesapeake

$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

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

$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

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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.