Chesapeake VA Homes for Sale

Welcome to Chesapeake, Virginia – a hidden gem nestled in the heart of Hampton Roads! Known for its picturesque landscapes, vibrant communities, and rich history, Chesapeake offers a unique blend of suburban charm and urban convenience. With over 350 miles of navigable waterways, this city is a paradise for boating enthusiasts, nature lovers, and anyone who enjoys a relaxed outdoor lifestyle.

Chesapeake is home to a diverse array of neighborhoods, each with its own character and appeal. From the historic charm of Great Bridge to the family-friendly atmosphere of Greenbrier, there is a perfect home for everyone. The city boasts top-rated schools, beautiful parks, and a wealth of recreational opportunities, making it an ideal place for families, young professionals, and retirees alike.

For those looking to settle down in this vibrant community, there are numerous homes for sale that cater to all tastes and budgets. Whether you’re seeking a cozy bungalow, a spacious family home, or a luxurious waterfront property, Chesapeake's real estate market has something for everyone. With competitive prices and an array of amenities nearby, now is the perfect time to explore your options in this thriving area.

Imagine waking up to serene views and enjoying the friendly atmosphere of Chesapeake. With its convenient access to major highways, shopping centers, and dining options, you’ll find everything you need right at your fingertips. Come discover why so many are proud to call Chesapeake home – your dream property awaits!

Newest Chesapeake VA Homes for Sale

$375,000

4 Beds ⋅ 3 Baths ⋅ 10652948 MLS

Welcome to this charming Chesapeake home, thoughtfully refreshed and ready for you to move right in. Recent updates include water-resistant LVP flooring, plush new carpet, and fresh touch-ups throughout for a clean, modern feel. Conveniently located and well maintained, it's the perfect place to settle in and enjoy. Enjoy living spaces and a practical layout near shopping and bases. Please contact the Listing Agent for the showing schedule; the home is occupied and owner requires proper notice.

1431 Oliver Avenue, Central Chesapeake

$450,000

4 Beds ⋅ 2.1 Baths ⋅ 10653149 MLS

Welcome home to Greenbrier! This beautifully maintained, move in ready home is tucked away on a desirable cul-de-sac in the heart of Chesapeake. Featuring numerous recent updates, you can move in with confidence and enjoy! The kitchen was updated in 2023 with new cabinets, countertops, and appliances. All bathrooms were refreshed in 2024 with new vanities, sinks, tubs, toilets, flooring, and paint. Major updates include a roof (2017), fence (2021), HVAC furnace (2025), condenser(2026), and water heater (2026). The first floor offers a spacious foyer, open living and dining areas, plus flexible bonus space great for a home office or playroom. Upstairs features a large primary suite with private bath and walk-in closet, three additional bedrooms, and a spacious shared bath. Conveniently located near Greenbrier shopping, dining, interstates, and local attractions. Don't miss your opportunity to make this home yours!

1914 Keeter Run, South Chesapeake

$300,000

4 Beds ⋅ 2 Baths ⋅ 10653273 MLS

Welcome to Crestwood Gardens in Chesapeake! This beautifully updated, turn-key home offers modern style, comfort, and functionality in an established NO HOA neighborhood. Enjoy fresh paint, plush new carpeting, and durable luxury vinyl plank flooring throughout. The remodeled kitchen features soft-close shaker cabinets, quartz counter-tops, stainless steel appliances, and a custom tile back-splash. The spacious primary suite includes a private en-suite bath. Major updates include a new roof, new windows, and updated plumbing and electrical for added peace of mind. Outside, enjoy a large detached garage offering excellent space for parking, storage, hobbies, or a workshop. Located in the Great Bridge High School district with quick access to interstates, shopping, and dining. Perfect for first-time buyers, down-sizers, or anyone seeking an affordable, move-in-ready Chesapeake home!

1325 Great Bridge Boulevard, Central Chesapeake

$544,900

4 Beds ⋅ 3 Baths ⋅ 10653325 MLS

A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch style living with 4 bedrooms including a large finished room over the garage. From the front porch to the Family Room also open to the Kitchen and Breakfast Area. The Estates at Jolliff Landing is a charming neighborhood boasting single family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your door step in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

2213 Wilmington Avenue, West Chesapeake

$365,000

4 Beds ⋅ 3 Baths ⋅ 10653190 MLS

Welcome to 1308 Sunnybrook Terrace! This well-maintained 4-bedroom, 3-full-bath home offers a spacious and functional layout designed for comfortable everyday living. With generous living areas, four nicely sized bedrooms, and the convenience of three full bathrooms, there’s plenty of room to spread out and make this home your own. Whether you’re a first-time homebuyer, growing household, or investor, this property offers flexibility and plenty of possibilities. Conveniently located in Chesapeake near shopping, dining, schools, and major roadways. Don’t miss the opportunity to call 1308 Sunnybrook Terrace home!

1308 Sunnybrook Terrace, West Chesapeake

$245,000

2 Beds ⋅ 2 Baths ⋅ 10653328 MLS

Nice waterfront brick ranch in a quiet neighborhood with a large yard & tidal canal that goes out to the Elizabeth River. Kitchen opens to large family room, two large bedrooms and two full bathrooms. Over sized attached garage with carport & detached single car garage flood insurance not required.

2112 Christopher Drive, West Chesapeake

$424,900

3 Beds ⋅ 2 Baths ⋅ 10653150 MLS

Welcome to your own private backyard oasis! Just steps from the water, tucked away on a quiet cul-de-sac. This beautifully updated 3-bedroom, 2-bath single?level ranch offers approximately 1,664 sq. ft. of comfortable living with an outdoor setting made for relaxing, entertaining and enjoying summer at home. Step outside to a fully fenced backyard featuring an in-ground pool with newer liner and pump, expansive concrete patio areas, covered pergola/outdoor living spaces, landscape lighting, irrigation and plenty of room for gatherings, grilling or quiet evenings by the pool. Inside, the thoughtfully redesigned primary suite features an expanded bedroom, dressing/closet area and beautifully remodeled bath with double vanity, oversized LED mirrors, glass-enclosed shower and jetted tub. Additional highlights include LVP flooring, an updated kitchen with granite countertops, two fixed fireplaces, updated lighting and finishes, huge 2 level detached workshop/storage, 2-car carport and no HOA. More than a home it's a place to enjoy every day. Extensive improvements completed in 2024 - 2025; detailed Features & Upgrades, Conveyance/Exclusion, and Seller Information package available upon request. This home is a must-see in person contact your agent to schedule a private showing.

1100 Dane Street, South Chesapeake

$639,900

4 Beds ⋅ 2.1 Baths ⋅ 10653324 MLS

Located in the highly coveted Grassfield High School District, this beautifully maintained 2021-built home offers modern style, thoughtful design, and plenty of natural light. The bright, open floor plan features hardwood floors throughout the entire first floor and a desirable downstairs primary suite. The chef’s kitchen is the heart of the home, showcasing quartz countertops, a gas range, and a deep island providing generous seating and additional prep space. The primary bath continues the elevated finishes with quartz countertops, dual shower heads, and beautiful upgraded tile. A first-floor laundry room adds everyday convenience, while the spacious all-seasons screened-in porch creates the space to relax or entertain year-round. With its inviting layout, quality finishes, and abundance of natural light, this home offers the perfect blend of comfort and style.

2065 Shipyard Road, South Chesapeake

$539,900

4 Beds ⋅ 2.1 Baths ⋅ 10653218 MLS

Welcome to this spacious, thoughtfully designed home offering generous living areas and a floor plan that blends comfort with functionality. Several updates have already been completed, to include: HVAC, roof, house trim, soffit, & gutter system, electric stove, carpet/LVT flooring, some interior paint, new pool salt system & Dolphin pool vacuum. The expansive backyard is a true retreat, featuring beautiful mature trees, a sparkling in-ground saltwater pool, and a spacious deck perfect for entertaining or unwinding. Situated on a large lot with a two-car garage, this property offers the ideal combination of space, privacy, and potential. Conveniently located in the sought after Hickory school district and near shopping, dining, and major commuter routes, this is a home you'll want to experience in person.

1505 Hilltop Drive, South Chesapeake

$499,900

5 Beds ⋅ 3 Baths ⋅ 10653261 MLS

BRAND-NEW CONSTRUCTION IN AN ESTABLISHED CHESAPEAKE NEIGHBORHOOD! Welcome to 3705 Davis Avenue, where modern design and the ease of new construction come together in an established community. Offering approximately 2,550 square feet, this spacious home features 5 bedrooms, 3 full baths, and a thoughtfully designed open floor plan with flexibility for today's lifestyle. A standout feature is the oversized first-floor bedroom with direct access to a full bath, also conveniently accessible from the hallway. This versatile space is ideal for multigenerational living, an in-law suite, overnight guests, a private home office, or anyone seeking comfortable first-floor accommodations. Davis offers the opportunity to enjoy a fresh, modern home without giving up the character and convenience of an established neighborhood.

3705 Davis Avenue, Central Chesapeake

$680,000

4 Beds ⋅ 3 Baths ⋅ 10652980 MLS

Located in Western Branch, this spacious 4-bedroom, 3-bath brick home offers a flexible layout with inviting indoor and outdoor living spaces. Fresh new carpet complements the hardwood flooring found throughout much of the home. The kitchen features granite countertops, stainless steel appliances, and plenty of space for everyday living. A cozy fireplace anchors the main living area, with easy access to the expansive back deck for outdoor entertaining or relaxing. Upstairs, the primary suite features a walk-in closet and private bath with a jetted soaking tub and separate shower. With generous living spaces, three full bathrooms, and thoughtful updates throughout, this home is ready for its next chapter. Don’t miss it!

1529 Lauren Ashleigh Drive, West Chesapeake

$325,000

3 Beds ⋅ 2 Baths ⋅ 10652903 MLS

Welcome Home to Deep Creek! Don’t miss this charming and well-maintained 3-bedroom, 2-bath ranch-style home nestled in an established neighborhood. Offering approximately 1,388 square feet of comfortable living space, this home has plenty of room to live, work, and entertain. The home features a spacious living room and a versatile flex room that can easily be used as a home office, playroom, second living area, hobby space, or whatever best fits your lifestyle. The spacious bedrooms offer plenty of room for comfort, while the kitchen includes a convenient eat-in area perfect for everyday meals. Step outside to the huge, fully fenced backyard, offering plenty of space for entertaining, outdoor gatherings, pets, gardening (check out the fruit trees), or simply relaxing and enjoying the outdoors. With its flexible floor plan, spacious backyard, and convenient Deep Creek location, this home is ready for its next owner. Schedule your private showing today!

3117 Kenelm Drive, 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.