Chesapeake 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 is known for its lush landscapes, rich history, and a strong sense of community. With over 350 miles of navigable waterways, this city is a paradise for boating enthusiasts, offering endless opportunities for fishing, kayaking, and enjoying the serene beauty of nature.

Chesapeake is home to a diverse population and a variety of amenities, including top-rated schools, shopping centers, and recreational parks. Whether you’re exploring the scenic Dismal Swamp Canal or enjoying a family day at the Chesapeake City Park, there's something for everyone in this welcoming city. The local dining scene is equally impressive, featuring everything from cozy cafes to fine dining establishments that celebrate the region's culinary heritage.

If you’re considering making Chesapeake your home, you’ll be pleased to know there are a variety of homes for sale to suit every lifestyle. From charming single-family houses in friendly neighborhoods to modern townhomes with all the latest amenities, the real estate market in Chesapeake offers something for everyone. Many properties boast spacious yards, perfect for family gatherings or quiet evenings under the stars.

With its perfect blend of nature, community spirit, and convenient access to nearby cities, Chesapeake is more than just a place to live; it’s a place to thrive. Explore our listings today and discover the perfect home in this delightful city!

Newest Chesapeake Homes for Sale

$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

$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

$292,000

4 Beds ⋅ 2 Baths ⋅ 10647346 MLS

4 bedroom ranch offering an open layout. This home features a converted garage that provides additional living space. Come check this home out, it wont last long!

3931 Port Road, Chesapeake

$604,900

3 Beds ⋅ 2.1 Baths ⋅ 10647287 MLS

Nestled in Greenbrier, Joseph’s Meadow is the newest community by a renowned local builder. The Primrose Cottage welcomes you with a charming full front porch, soaring two-story family room, and beautiful Mohawk flooring throughout the main living areas. Designed for effortless living and entertaining, the open layout connects the family room, dining area, and HGTV-inspired chef’s kitchen featuring oversized quartz island, custom hood & floating shelves, designer finishes, and mudroom. The first-floor primary suite offers a custom walk-in closet, spa-like bath with quartz dual vanity, tiled shower, and private laundry. Upstairs two spacious bedrooms, tons of storage and large laundry room. (Opt. to add 4th BR or Loft) Professionally managed grounds provide a low-maintenance lifestyle, giving you more time to enjoy the comfort, quality, and craftsmanship of your Primrose haven. To be built to your specs from designer showroom. Intimate neighborhood with limited building opportunities.

MM Primrose A, Chesapeake

$430,000

3 Beds ⋅ 2.1 Baths ⋅ 10647306 MLS

Welcome to this beautifully maintained open-concept home in the heart of Greenbrier! This move-in-ready home offers a spacious layout with separate living and dining rooms, plus a warm family room that opens to the updated kitchen—perfect for everyday living and entertaining.Recent 2025 updates include a new HVAC system, granite countertops throughout, LED recessed lighting, upgraded ceiling fans, updated bathroom fixtures, and a stylish subway tile backsplash. The washer and dryer were replaced in 2021.Enjoy a private backyard oasis and the convenience of low-maintenance living with a Master Association Policy. The Master Association Policy covers roof and fencing repairs/replacement, lawn maintenance, exterior painting, gutter cleaning and power washing annually, Don't miss out this gem is priced to sell !!!

808 Monroe Court, Chesapeake

$610,900

3 Beds ⋅ 3.1 Baths ⋅ 10647285 MLS

Augusta Expanded Plan To be built w/ your finishes - Opt to convert loft to BR4. Dreamy Augusta Cottage by coveted local builder w/unmatched architectural detail, from custom arches to soaring 10’ ceilings & stunning hardwood floors. Open-concept 1st floor blends Dining & Great Rm, w/French doors opening to private courtyard & patio, your outdoor oasis. Chef’s kitchen shines w/oversized island, Quartz counters & custom range hood. Generous 1st-floor BR w/ensuite bath offers flexible living. Versatile mudroom w/pantry, powder room & access to 2-car garage make everyday living effortless. Upstairs, sun-filled BR3 features walk-in closet, while BR4 (or loft) adapts to your needs. Also included are a shared dual bath & oversized laundry room. Private Primary retreat boasts spa bath w/ dual sinks, garden tub, large tiled shower & super-sized walk-in closet w/ dual storage areas. Professionally managed grounds offer low-maintenance living. Luxury, comfort & lifestyle in one exceptional home.

900 Koonce Lane, Chesapeake

$610,900

3 Beds ⋅ 2.1 Baths ⋅ 10647280 MLS

Nestled in Greenbrier, Joseph’s Meadow is the newest community by the renowned local builder. The Lily Cottage welcomes you with a full front porch, soaring 10-foot ceilings, and beautiful hardwood floors throughout the first floor. Designed for everyday living and entertaining, the open-concept layout seamlessly connects the living room, dining area, and stunning chef’s kitchen featuring a 9-foot quartz island, custom hood, and oversized walk-in pantry. Mudroom and powder room are conveniently tucked away by 2-car garage. Upstairs, a sun-filled loft, two spacious bedrooms, loft (opt 4th), and a large laundry room provide exceptional functionality. The private primary suite offers a custom walk-in closet and spa-inspired bath with quartz countertops, dual vanities, freestanding tub, tiled shower, and private water closet. Easy living with professionally managed grounds ensures low-maintenance living, making your dream truly a peaceful haven.

MM Lily A Or B, Chesapeake

$405,000

4 Beds ⋅ 2 Baths ⋅ 10647166 MLS

If you're looking for a move-in-ready home in a desirable neighborhood that offers both style and peace of mind, you’ve found it. Meticulously maintained and showcasing true pride of ownership, this home was fully renovated in 2024 with a stunning modern kitchen and updated bathrooms, featuring quartz countertops, luxury vinyl plank flooring, stylish fixtures, and a screened porch perfect for relaxing or entertaining. Major systems have also been updated, with the roof, windows, tankless water heater, and HVAC all just two years old…allowing you to move in with confidence and enjoy your new home for years to come.

904 Levee Lane, 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.