Chesapeake Homes for Sale

Welcome to Chesapeake, Virginia – a vibrant city that beautifully marries suburban charm with urban conveniences. Nestled in the heart of Hampton Roads, Chesapeake boasts a rich tapestry of history, culture, and natural beauty. With its picturesque waterfront, expansive parks, and a plethora of recreational activities, it’s no wonder that families and individuals alike are drawn to this thriving community.

Chesapeake is known for its diverse neighborhoods, each offering unique characteristics and amenities. From the serene, tree-lined streets of Great Bridge to the bustling atmosphere of Greenbrier, there’s a perfect home for everyone. The city is also home to top-rated schools, making it an ideal place for families looking to settle down.

For those searching for their dream home, Chesapeake’s real estate market is flourishing. With a wide range of properties available, from cozy single-family homes to spacious townhouses and luxurious waterfront estates, there is something to suit every lifestyle and budget. The homes for sale in Chesapeake often feature modern amenities, beautiful landscaping, and easy access to local shops, dining, and entertainment.

In addition to its residential appeal, Chesapeake is steeped in outdoor adventure. With over 22,000 acres of parks, including the stunning Great Dismal Swamp National Wildlife Refuge, residents can enjoy hiking, biking, and birdwatching right in their backyard.

Whether you’re a first-time homebuyer or looking to upgrade, Chesapeake, VA, offers an inviting community and a wealth of opportunities. Come explore the homes for sale and discover why so many people are proud to call Chesapeake home!

Newest Chesapeake Homes for Sale

$425,000

3 Beds ⋅ 1.1 Baths ⋅ 10659765 MLS

Two homes, one opportunity at 1672 & 1674 Benefit Road! These two neighboring properties are being sold together, giving you three separate living spaces on adjoining lots. The main home at 1674 is a charming 3-bedroom, 1.5-bath home with a welcoming covered front porch, a spacious yard, and a long driveway. Inside, you’ll find luxury vinyl plank flooring, bright bedrooms with ceiling fans, and an updated kitchen with white cabinetry, granite-look counter tops, and modern appliances. Out back, the garage has been fully converted into a code-compliant 2-bedroom, 2-bath apartment with its own entrance. It features a stylish galley kitchen with stainless appliances, in-unit laundry, durable LVP flooring, and a subway-tile walk-in shower with a built-in bench and pebble floor. Next door, 1672 is a 3-bedroom, 2-bath brick ranch that’s ready for your personal touch and adds even more space and income potential. This property can work for you in several ways. For multi generational living, keep loved ones close while everyone has their own kitchen, entrance, and privacy. Aging parents, adult children, and long-term guests can each have a place of their own, just steps away. To house hack, live in one home and let the other two help cover your mortgage, building equity and wealth while you live there. As an investor, hold all three as long-term rentals for three income streams in one purchase and one location. Best of all, the property can change with you: start as a family property today and convert it to rental income later, or the other way around. Opportunities like this rarely come to market. So bring your vision and schedule your showing today!

1674 Benefit Road, Chesapeake

3901 Cannon Point Drive Drive, Chesapeake

$445,000

3 Beds ⋅ 3 Baths ⋅ 10659719 MLS

Welcome to 3901 Cannon Point Drive, where timeless elegance meets modern comfort! This beautifully maintained 3-bedroom, 2-bath brick ranch offers 1,575 square feet of stylish single-level living on a gorgeous, landscaped corner lot in Western Branch. Step inside to discover gleaming hardwood floors, elegant plantation shutters throughout, and a stunning updated kitchen featuring granite countertops, custom cabinetry, and newer appliances. Both bathrooms have been tastefully remodeled with beautiful tile finishes. Relax in the inviting den featuring a cozy gas fireplace and brand-new carpeting. Additional improvements include replacement windows, a newer roof, and a professionally inspected and sealed crawlspace. Outside, meticulous landscaping creates exceptional curb appeal and a picturesque setting. Combining classic charm, thoughtful upgrades, and undeniable pride of ownership, this Western Branch beauty is a must-see!

3901 Cannon Point Drive Drive, Chesapeake

$225,000

3 Beds ⋅ 2 Baths ⋅ 10659764 MLS

Two homes, one opportunity at 1672 & 1674 Benefit Road! These two neighboring properties are being sold together, giving you three separate living spaces on adjoining lots. The main home at 1674 is a charming 3-bedroom, 1.5-bath home with a welcoming covered front porch, a spacious yard, and a long driveway. Inside, you’ll find luxury vinyl plank flooring, bright bedrooms with ceiling fans, and an updated kitchen with white cabinetry, granite-look counter tops, and modern appliances. Out back, the garage has been fully converted into a code-compliant 2-bedroom, 2-bath apartment with its own entrance. It features a stylish galley kitchen with stainless appliances, in-unit laundry, durable LVP flooring, and a subway-tile walk-in shower with a built-in bench and pebble floor. Next door, 1672 is a 3-bedroom, 2-bath brick ranch that’s ready for your personal touch and adds even more space and income potential. This property can work for you in several ways. For multi generational living, keep loved ones close while everyone has their own kitchen, entrance, and privacy. Aging parents, adult children, and long-term guests can each have a place of their own, just steps away. To house hack, live in one home and let the other two help cover your mortgage, building equity and wealth while you live there. As an investor, hold all three as long-term rentals for three income streams in one purchase and one location. Best of all, the property can change with you: start as a family property today and convert it to rental income later, or the other way around. Opportunities like this rarely come to market. Properties must be purchased together, so bring your vision and schedule your showing today!

1672 Benefit Road, Chesapeake

$499,900

4 Beds ⋅ 2 Baths ⋅ 10659700 MLS

Nestled in the heart of Greenbrier, this move-in-ready 4-bedroom home offers a bright and welcoming atmosphere from the moment you step inside. Soaring cathedral ceilings and skylights fill the main living space with natural light, creating a balance of open-concept entertaining areas and comfortable, cozy corners. Adapt the versatile room off the kitchen to suit your lifestyle, whether as a formal dining room, quiet home office, or vibrant playroom. Thoughtfully updated with modern kitchens, bathrooms, and flooring, plus peace-of-mind upgrades from 2023 including a new HVAC, air ducts, insulation, and water heater. Retreat to the primary suite featuring a walk-in closet and a spacious updated bathroom. All of this is located just minutes away from Greenbrier shopping and Greenbrier Country Club.

744 Norcova Drive, Chesapeake

$395,000

4 Beds ⋅ 2 Baths ⋅ 10659664 MLS

Deep Creek - Just off Route 17/George Washington Highway exit - Beautifully renovated - move-in ready brick ranch with large private lot. White shaker style kitchen cabinetry with granite countertops, LVP flooring throughout - 4 bedrooms, 2 full baths - freshly painted, nice floor plan - large new deck off rear of home with French doors to deck and huge backyard - room for anything you enjoy! Large shed in backyard plus 1 car attached garage. Conveniently located, feels like country living, though close to everything. Great opportunity to live in Deep Creek and enjoy all this area has to offer!

2868 Flag Road, Chesapeake

$270,000

4 Beds ⋅ 2 Baths ⋅ 10659481 MLS

Welcome to 1104 Wright Avenue, where comfort, value, and opportunity come together! This inviting home is the perfect canvas to bring your vision to life, offering endless potential to create a space that truly reflects your style. Enjoy the peace of mind that comes with a brand new HVAC system.

1104 Wright Avenue, Chesapeake

$569,490

5 Beds ⋅ 3.1 Baths ⋅ 10659437 MLS

The Poppy is a spacious open-concept home with a total of five bedrooms. When you enter from the covered front porch, you are led form the foyer to a vast great room, dining room and kitchen. While one bedroom and full bathroom is downstairs, upstairs you will find three additional bedrooms with another full bath equipped a double vanity. Continuing on the second floor is the owner's suite, with an option for tray ceilings, sinks on two separate vanities, and a large walk-in closet. The owner's bathroom has the option for a seat in the shower. The laundry room is conveniently located on the second floor. Directions: Portsmouth Blvd to Walker Lane, make left, then Left on Joliff Landing Road, Model is on Paw Paw place

1822 Citrus Place, Chesapeake

$510,000

4 Beds ⋅ 2 Baths ⋅ 10659574 MLS

WOW! Rare find in the heart of Etheridge! This brick ranch sits on OVER an acre lot, an extremely rare find in the area, & is priced below a recently completed appraisal! Numerous updates within the last 5yrs include kitchen with granite countertops ('22), LVP flooring ('21/'22), roof ('21), HVAC ('21), bathrooms ('21), water heater ('24), fenced backyard ('22), extra-wide driveway ('22), vinyl-wrapped trim ('21) & encapsulated crawl space ('22). Need extra space for hobbies, entertaining, or storage? The property includes an extra large shed measuring an impressive 14x40 with electricity! The seller has converted a 14x28 portion of this space into a game room, offering more possibilities. Located in the sought-after Hickory school zone & convenient to shopping, restaurants, hospitals, interstates, and bases. Enjoy country living with the convenience of city amenities! 1yr lender paid rate buy down offered if buyer uses qualifying loan w/preferred lender, ask LA for details.

700 Gladesdale Drive, Chesapeake

$639,900

4 Beds ⋅ 2 Baths ⋅ 10659515 MLS

Gorgeous open floor custom built ranch w/twelve ft ceilings in family & dining room, nine ft ceilings in bedrooms. Finished room over garage can serve as 4th bedroom or bonus room. Enjoy kitchen w/granite countertop, bar seating area, stainless steel energy efficient appliances, custom cabinets, w/recessed lights; Opens to large breakfast nook overlooking a tranquil country backyard. Stunning great room with gas fireplace; hardwood floors, crown molding; Large formal dining room w/chair rails. Private study/office w/ custom built-in cabinets and bookshelves, granite counters and full-light doors creating a bright workspace; tray ceiling in luxurious primary bedroom w/large custom design walk-in closet. Recent appraisal confirms price. Relatively near the heart of Chesapeake.

732 Washington Drive, Chesapeake

$665,900

5 Beds ⋅ 3.1 Baths ⋅ 10659608 MLS

Joseph’s Meadow (MODEL GPS 369 Scotland Ln. Chesapeake) Nestled in Greenbrier come visit the newest community by renowned local builder. Lily Cottage C welcomes you w/ a full front porch, airy 10-foot ceilings & HW floors entire first floor. Designed for entertaining, the open-concept layout seamlessly connects the living room, dining area, & stunning chef’s kitchen featuring a 9-foot quartz island, custom hood, & HUGE walk-in pantry. Mudroom and powder room are conveniently tucked away by 2-car garage. Custom stair detail mid level with loft, 2 bedrooms + full bath -dual sinks, private tub/shower & water closet. HUGE laundry room. LUSH Primary suite entry w/custom walk-in closet and SPA retreat w/ quartz countertops, dual vanities, freestanding tub, tiled shower & private water closet. Third flr features 2 BR, Full bath, 2 walk in Attic storage! Easy living w/professionally managed grounds low-maintenance living, making easy living a reality!

389 Scotland Lane, Chesapeake

$370,000

4 Beds ⋅ 2 Baths ⋅ 10659575 MLS

Move-in ready and beautifully refreshed! This vacant 4-bedroom Chesapeake home has been thoughtfully updated from top to bottom, featuring a new roof (2025), HVAC (2026), water heater (2021), new LVP flooring, new carpet in all four bedrooms, renovated bathrooms, new kitchen appliances and custom cabinetry, new interior and exterior doors, updated GFCI outlets in the kitchen and bathrooms, and new light fixtures throughout. Enjoy the added curb appeal of a freshly repaved driveway and new framing around the left front window. Inside, a newly installed decorative TV wall with backlighting creates a stylish focal point for entertaining and relaxing. Located in the convenient Western Branch area, you're close to shopping, dining, recreation, schools, and major Hampton Roads routes. With major updates already completed and easy showings available, this home is ready for you to move in and make it yours! Schedule your showing today?

3116 Dunworken Drive, Chesapeake

$325,000

3 Beds ⋅ 2 Baths ⋅ 10659597 MLS

Welcome to a charming 3-bedroom, 2-bath brick ranch offering comfortable single-level living with modern updates throughout. The open floor plan features inviting living spaces, refreshed finishes, and plenty of potential to make the home your own. Its classic brick exterior provides timeless curb appeal and lasting durability. Conveniently located near everyday amenities, this property is a great opportunity for homeowners or investors. Property is being sold "AS IS WHERE IS"

1213 Lilac Avenue, 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.

Chesapeake Homes for Sale

Newest Chesapeake Homes for Sale

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