Chesapeake VA Homes for Sale

Welcome to Chesapeake, Virginia—a hidden gem nestled in the heart of Hampton Roads. Known for its rich history, vibrant culture, and stunning natural beauty, Chesapeake offers an unparalleled living experience for families, professionals, and retirees alike. With over 22 miles of waterfront, this charming city boasts an abundance of parks, trails, and waterways, making it a paradise for outdoor enthusiasts. Whether you enjoy fishing, kayaking, or simply taking leisurely strolls through lush landscapes, Chesapeake has something for everyone.

As you explore the homes for sale in Chesapeake, you’ll discover a diverse array of properties that cater to various lifestyles and budgets. From quaint single-family homes in friendly neighborhoods to luxurious waterfront estates, there’s a perfect home waiting for you. The real estate market here is thriving, with new listings emerging regularly, showcasing the unique architectural styles and modern amenities that define Chesapeake living.

Families will appreciate the top-rated schools and community-focused atmosphere, while professionals can enjoy easy access to major highways and employment centers in nearby Norfolk and Virginia Beach. With a growing number of shops, restaurants, and entertainment options, Chesapeake is not just a place to live—it’s a place to thrive.

Whether you’re looking to settle down or invest in a vacation home, now is the perfect time to explore the homes for sale in Chesapeake, VA. Embrace a lifestyle where comfort meets convenience, and make this vibrant city your new home sweet home!

Newest Chesapeake VA Homes for Sale

$390,000

3 Beds ⋅ 2.1 Baths ⋅ 10648235 MLS

The moment you walk through the door, you'll feel right at home. The spacious open layout is perfect for everyday living, whether you're enjoying a quiet evening or hosting friends and family. The thoughtfully designed primary suite offers a private retreat with a full bath and generous walk-in closet, while luxury vinyl plank flooring flows throughout the home. Recent improvements, including the 2023 addition, updated kitchen cabinetry, windows, electrical, heat pump, lighting and, fixtures, provide modern comfort and peace of mind. Outside, the fenced corner lot offers plenty of room to enjoy, with a deep driveway for ample parking. Located in an established Chesapeake neighborhood with convenient access to shopping, dining, parks, and major commuter routes, this home is one you'll want to experience in person before it's gone.

1324 Hawthorne Drive, Central Chesapeake

$825,000

4 Beds ⋅ 3.1 Baths ⋅ 10648270 MLS

Beautiful custom home on 3 Acres that backs up to woods! Two Primary Suites, one downstairs and one upstairs each with their own full bath! Amazing custom Kitchen with loads of storage, Pantry, plenty of counter space, center island, brand new cabinets, granite and Stainless Steel Appliances! Dual zoned central Heat/AC. Move in ready! Located in the Grassfield School district! Completely remodeled and waiting for you, be sure to come check this one out first!No HOA, bring your horses, chickens and goats!

2239 Benefit Road, South Chesapeake

$269,900

3 Beds ⋅ 1 Baths ⋅ 10648228 MLS

Ready for you to move right in! This fully refreshed 3 bed, 1 bath home has all the big-ticket updates already done for you. Brand-new flooring throughout (July 2026), fresh interior paint (2025), and new siding (2025) give it a clean, updated feel from the moment you walk in, while the roof on both the home and the detached garage was replaced just 4 years ago. Out back is where this property really stands out: a 16x24 detached garage with electric and attic storage makes an ideal workshop, hobby space, or overflow storage, and TWO additional carports mean covered parking for multiple vehicles, a boat, or a trailer. If you've been looking for a truly move-in-ready home with serious garage and parking space, 809 Clay Avenue delivers. Call to schedule your showing today!

809 Clay Avenue, South Chesapeake

$500,000

4 Beds ⋅ 2.1 Baths ⋅ 10648263 MLS

Stunning waterfront views! Spacious Brick front ranch with a new kitchen, quartz countertops, new stainless appliances, slow close cabinets, large island and 42" upper cabinets. Eat in kitchen with bay windows overlooking the lake! Large family room, LVP flooring and an oversized deck with an awning. Sits on over 1/4-acre with a 2-car garage and a recent solar panel installation. There is structural termite and moisture damage in the crawl space and the home. Only CASH offers will be considered. Buyer must assume the solar panel loan, approx. $35,000. 19 years @ $150.00 a month. Electric bills as low as $10.00 a month.

1121 Copper Stone Circle, South Chesapeake

$950,000

5 Beds ⋅ 3 Baths ⋅ 10648261 MLS

Welcome to your private 3.25-acre country oasis, where luxury finishes, heavy-duty infrastructure, and absolute peace of mind converge. This beautifully updated single-story home offers an open-concept layout and highly functional spaces, making it a rare market find. INTERIOR HIGHLIGHTS Step inside to a bright, airy open floor plan where the living and dining areas flow seamlessly into the chef-inspired kitchen. The kitchen is outfitted with premium Cambria countertops for unmatched durability and sleek modern style. The primary suite serves as a spa-like retreat, boasting natural quartzite surfaces, a deep jetted soaking tub, and a massive 4x4 walk-in shower. Upstairs, a versatile finished room over the garage (FROG) and a charming attic dormer offer excellent bonus spaces for a home office, media room, gym, or guest quarters. OUTDOOR LIVING & ENTERTAINING Embrace the scenic acreage from your choice of outdoor living areas. Relax on the welcoming covered front porch, or host unforgettable gatherings on the expansive rear covered patio. The outdoor living experience is anchored by a fully equipped outdoor kitchen, great for weekend barbecues and dining al fresco while overlooking your sprawling, private acreage. THE ULTIMATE DETACHED WORKSHOP A true standout feature is the massive 2,200 sq. ft. detached workshop. This incredible building is fully powered and completely climate-controlled with heating and cooling, making it an ideal setup for a home business, car enthusiast, hobbyist, or extensive machinery storage. PREMIUM SYSTEMS & INFRASTRUCTURE No expense was spared on the home's mechanics and structural integrity: * Power Security: Whole-home generator supported by a recently added 500-gallon propane tank. * Efficiency: All-new energy-efficient windows and updated insulation throughout. * Roof & Plumbing: Roof is approx. 4 years young. All plumbing has been fully updated with zero cast iron. * Utilities: Tankless water heater for endless hot water; septic system recently serviced. Welcome Home.

1908 Benefit Road, South Chesapeake

$625,000

4 Beds ⋅ 3 Baths ⋅ 10648242 MLS

Welcome to this stunning beautiful home nestled on a quiet cul-de-sac! From the moment you enter, you’ll appreciate the grand condition of this home, featuring 4 bedrooms, 3 full bathrooms and thoughtful updates throughout. Gorgeous hardwood floors running through the main living area and in the expansive room over the garage. At the heart of the home is a fully renovated gourmet kitchen featuring sleek white quartz countertops, premium stainless steel appliances, and ample cabinet space—flawless setting for everyday living and entertaining. Upstairs, the luxurious primary suite serves as a private retreat, complete with a spa-inspired ensuite bath featuring dual vanities and a custom dual shower. Roof is approx. 7 years old, brand-new replacement windows, dual-zone HVAC system and encapsulated crawl space, for year-round comfort. Step outside to take in serene lake views and enjoy the peaceful backyard setting. Truly turn-key and move-in ready—schedule your tour today!

811 Twin Peak Ct Court, South Chesapeake

$315,000

2 Beds ⋅ 1 Baths ⋅ 10648165 MLS

Rare 1.54-acre homesite in a highly desirable Chesapeake location! The property includes an existing home and out buildings that convey as-is. Suitable for renovation. R-15S zoning and an outstanding location near Greenbrier, major highways, shopping, dining, and schools, this property offers endless possibilities for investment.

304 Centerville Turnpike N, South Chesapeake

$300,000

2 Beds ⋅ 1 Baths ⋅ 10647978 MLS

Investors! 2 Parcels totalling 22.25 +/- acres currently zoned M1 for large tract (17.5acres) and residential small tract (4.75 acres) This piece of land must be purchased with 1828 Mount Pleasant Road which is right nextdoor and runs parallel to property and has a small house with power, septic and well. Subject to zoning, interested parties should contact the City of Chesapeake Zoning and Planning for allowable uses.

1832 Mount Pleasant Road, South Chesapeake

$544,900

5 Beds ⋅ 3.1 Baths ⋅ 10648220 MLS

Welcome to this spacious well-maintained 5-bedroom, 3.5-bath home right on the lake! This home spans approximately 2,800 sq ft. with fresh new carpet and interior paint. The layout includes dual primary bedrooms on both levels. The backyard offers a large deck, hot tub, and pool on nearly a half-acre lot. Energy-efficient features include solar panels to be paid off at settlement and a Rinnai tankless water heater. Convenient combination of space, updates, and outdoor features.

813 Stardale Drive, South Chesapeake

$594,900

5 Beds ⋅ 3.1 Baths ⋅ 10648173 MLS

PRE-SOLD TO BE BUILT: CALL LA1/LA2 FOR AVAILABLE LOTS & INVENTORY. A versatile floor plan with ample space for entertaining! Tha Palm offers 5 Bedrooms , 2.5 Baths, a large Family room, open to the kitchen, all BR's on 2nd floor, large patio space for outdoor living. A desirable Primary Suite bath & walk-in closet.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, a 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 doorstep 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 12-5 pm at 5023 Annapolis Drive.

5106 Annapolis Drive Unit 2332, West Chesapeake

$653,900

4 Beds ⋅ 3 Baths ⋅ 10648204 MLS

The Marigold is a thoughtfully designed rear-load home that blends convenience, elegance, and flexible living. With 2,703 square feet, this home offers four bedrooms to fit your needs. Upon entry, a dining area leads you into the upgraded gourmet kitchen and open great room. Enjoy a first floor owner's suite with tray ceilings, a spacious walk-in closet, and a upgraded deluxe spa-inspired bath. The first floor also includes a secondary bedroom, full bath, and laundry room for added convenience. Upstairs, You'll also find 2 additional bedrooms, a hall bath, and a versatile bonus room ready to become whatever you need most.

1956 Paw Paw Place, West Chesapeake

$290,000

4 Beds ⋅ 1.1 Baths ⋅ 10648144 MLS

AS IS, extra-large garage w/electricity & workshop area

3209 Dunworken Drive, West 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.