Homes for Sale in Chesapeake: Your Complete Real Estate Guide

Welcome to your ultimate source for the latest Chesapeake, VA real estate listings. Consistently ranked among the top places to live in the region, this area blends pristine natural beauty, highly rated school districts, and a robust local economy. Whether you are looking for a spacious suburban property, a low-maintenance townhouse, or a home with acreage, our live property database updates directly from the local MLS to ensure you never miss an opportunity. Explore our current inventory today and discover why so many residents and relocation professionals choose to plant roots here.

Top Local Neighborhoods

Great Bridge: A highly central and sought-after suburb celebrated for its public school districts, established communities, and vibrant hubs of shopping and dining.
Greenbrier: The commercial heartbeat of the area, offering an ideal mix of residential comfort, bustling retail centers, beautiful public parks, and seamless highway access.
Hickory: Perfect for buyers prioritizing extra space and a relaxed vibe, known for its expansive lots, custom construction, and highly rated schools.
Western Branch: Tucked into the northwestern corner, this peaceful area is a standout choice for its quiet atmosphere, parks, and excellent commuter access.
Deep Creek: A close-knit community bordered by the historic Great Dismal Swamp and the Intracoastal Waterway, offering amazing options for waterfront living and outdoor enthusiasts.

Seamless Home Buying Tools

Finding a house that fits both your lifestyle and your budget is effortless with our advanced search tools. Filter active listings by price, square footage, neighborhood, or specific home features. When you are ready to transition from browsing to buying, our experienced real estate team is here to guide you through competitive market conditions and organize private showings.

$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

10658012 MLS

Commercial office space available immediately in a great location! This 150-square-foot office offers access to common areas and a bathroom, with all utilities included in the monthly rent of $1,200. Ideal for a small business, professional, consultant, service provider looking for a convenient and comfortable workspace. Rent includes a waiting area with receptionist on site. Contact us today for more information or to schedule a viewing!

4536 Bruce Road Unit 2, West 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

10657975 MLS

Commercial office space available immediately in a great location! This 150-square-foot office offers access to common areas and a bathroom, with all utilities included in the monthly rent of $1,200. Great for a small business, professional, consultant, service provider looking for a convenient and comfortable workspace. Rent includes a waiting area with receptionist on site. Contact us today for more information or to schedule a viewing!

4536 Bruce Road Unit 1, West Chesapeake

$600,000

4 Beds ⋅ 3 Baths ⋅ 10657974 MLS

Welcome to 1108 Cumberland Ct, a beautifully staged Chesapeake home with a pool and a fenced backyard made for entertaining. Inside, enjoy bamboo flooring and premium crown molding throughout the main level. The kitchen features granite counters, tiled backsplash, a pocket door, a gas range (2022), a 2024 dishwasher, and whole-house plus reverse-osmosis water filtration. A full downstairs bath with a walk-in shower adds convenience, and the wood-burning fireplace is perfect for cool evenings. Major updates include roof and skylights (2015), gas furnace and A/C (2017), front windows (2020), and an encapsulated crawl space with new vapor barrier (2022). Walk-in attic, garage shelving, and comfort-height toilets. Open house Saturday, 10/17. Schedule your showing today!

1108 Cumberland Court, South Chesapeake

$279,900

2 Beds ⋅ 2.1 Baths ⋅ 10657138 MLS

Come See this Beautifully Maintained 2 Bedroom 2 1/2 Bathroom Condo in the Heart of Western Branch. Open Concept Kitchen with Breakfast Bar and Dining Area. SS Appliances and Quartz Countertops. Large Living Room with Slider to your Private Patio and Storage Shed. Laundry Closet. 2 Bedrooms with Ensuite Baths and Walk-In Closet Located Upstairs along with a Spare Room which can be used as an Office, Nursery, Craft Room or Storage. Community Amenities Include Ground Maintenance, Pool, Water and Trash. Conveniently Located Near Interstate, Shopping, Dining, Parks and Library. Welcome Home!

2456 Whitman Street, West Chesapeake

$850,000

5 Beds ⋅ 3 Baths ⋅ 10657808 MLS

This is the kind of Chesapeake home that feels substantial the second you walk in. Restored inside and out, it carries the scale and character of an established traditional home, with beautiful arched doorways, refinished hardwoods, fresh paint, new carpet, and thoughtful updates that make the entire house feel fresh again. The main level is generous without feeling disconnected. The kitchen sits between the formal dining room, the vast open living space, and the screened porch, making it the natural link between everyday living and entertaining. Ample white cabinetry wraps the room, while an oversized island, thick warm granite countertops, a ceramic Kohler sink, and new appliances give it both presence and function. From there, the screened porch opens to the rear deck and draws you straight out toward the pool. That backyard deserves its own moment. The in-ground pool sits within a wide paver surround and includes a diving board and built-in sitting ledge, all framed by decorative iron fencing. But the fence is not the end of the yard. The property continues beyond it with additional lawn space and an in-ground fire pit, giving the outdoor space far more depth than the pool area first reveals. Inside, nearly every turn brings another room with a purpose. A dedicated library adds character to the main level, while the separate billiard room creates another substantial place to gather. A first-floor bedroom sits near a modern updated full bath, and upstairs, a finished attic adds even more usable space with room for movies, games, hobbies, or whatever comes next. Then there is the primary suite, and it is genuinely oversized. Beyond the sleeping area is a separate sitting room, an enormous walk-in closet, and an ensuite with a jetted soaking tub and separate stand-up shower. Set in Carriage House Estates in Chesapeake’s 23322 with Hickory schools and a central location, this is a home where the size, flow, and character show up in all the right places—inside, outside, and in the spaces you do not expect until you are standing in them.

603 Oxbow Court, South Chesapeake

$980,000

6 Beds ⋅ 4 Baths ⋅ 10657839 MLS

An exceptional opportunity to own a Stephen Alexander custom home in Greystone, one of Chesapeake's premier luxury communities where homes are rarely available. This expansive executive residence blends timeless craftsmanship with the space, flexibility, and resort-style amenities today's luxury buyers seek. A first-floor bedroom with an adjacent full bath offers versatility for guests, a home office, or multi-generational living. The primary suite is a true retreat with a fireplace, sitting area, and four closets. Enjoy a private backyard oasis featuring an in-ground pool, hot tub, screened porch, gazebo, fire pit, privacy fence, irrigation well, and expanded parking for a boat or RV. Scenic walking paths enhance this sought-after community. Significant recent investments include a new roof (2026), three HVAC systems, an encapsulated crawl space, new hardwood flooring, updated bath vanities, freshly painted kitchen cabinetry, and a new oven. Schedule your private showing today!

821 Redleafe Circle, South Chesapeake

$575,000

5 Beds ⋅ 3.1 Baths ⋅ 10657811 MLS

Soaring cathedral ceilings, an updated kitchen, and a first-floor suite that feels almost like its own wing give this Waterstone home plenty to remember. The main living area feels open and connected, with a gas fireplace creating a natural focal point and cathedral ceilings adding volume overhead. The kitchen has been refreshed with painted white cabinetry, dark gray quartz countertops, a tile backsplash, black finishes, and newer appliances for a clean, current look. One of the home’s biggest standouts is the expansive first-floor suite, complete with private exterior access, a large closet, and its own sitting area. The scale and separation make it feel more like a private retreat than just another room. LVP flooring, newer carpet, and updated windows continue throughout the home. Above the two-car garage, another spacious living area with cathedral ceilings and LVP flooring adds even more flexibility for an office, media room, playroom, or additional living space. A partially encapsulated crawlspace with a high-quality dehumidifier is another meaningful improvement already in place. Outside, the back porch overlooks a large fenced yard with plenty of usable green space, while the two-car garage and generous driveway add everyday function. Waterstone offers a community pond for kayaking, canoeing, paddle boarding, and fishing, along with neighborhood trail access connecting directly to Western Branch Park and Western Branch Community Center. With substantial living space, thoughtful updates, and two areas that give you real flexibility beyond the main living spaces, this home has more depth than the photos first let on.

2004 Acentala Quay, West Chesapeake

$675,000

5 Beds ⋅ 3 Baths ⋅ 10657871 MLS

Well maintained all brick home with 2-car side loading garage, long driveway, 1/3 acre beautifully landscaped lot, situated on a cul-de-sac in Great Bridge. Open floor plan features huge kitchen with quartz countertops and overlooks fam room. FR has wood burning FP which is also plumbed for gas. In addition to the 5 bedrooms on 2nd floor, there is a 6th bedroom/office with adjacent full bathroom on 1st floor. Recent updates include 2nd floor 3 ton HVAC (Sept 2026), new carpets (Sept 2026), windows, roof, water heater, garage door, leaf filter gutters, more. Award winning Cheshire Forest community amenities include clubhouse, pool, tennis/pickle ball courts, parks and playgrounds. Screened porch with concrete floor overlooks the beautiful backyard. Seller to provide clear Termite/Moisture letters and 1 year home warranty.

810 Hedgerow Court, South Chesapeake

$630,000

5 Beds ⋅ 3.1 Baths ⋅ 10657755 MLS

Gorgeous & 4-years-young in community-friendly Culpepper Landing with scenic outdoor areas, clubhouse & pool! Huge open & bright floor plan enhanced by classic neutral décor. Enjoy flexible living spaces great for home office, study, dining room or homeschool station. Dreamy kitchen with an abundance of cabinetry, counter space & massive breakfast bar great for gathering & entertaining. Inviting family room sits at the heart of the home & opens to covered porch overlooking fenced backyard. Extra highlights include a convenient mudroom, organization area & finished room over the garage with full bath offering endless possibilities for a guest suite, media room or private retreat. With 5 bedrooms & 3.5 bathrooms, there's plenty of room for everyone to spread out. Elegant primary suite features exercise area, walk-in closet, dual-sink vanity & oversized shower with double shower heads. This is the Total Package & Across the street from brand NEW elementary school opening 2027-2028.

938 Olmstead Street, South Chesapeake

1221 Commerce Avenue, Central Chesapeake

$279,725

3 Beds ⋅ 2.1 Baths ⋅ 10657786 MLS

A 2.75% ASSUMABLE MORTGAGE, UPDATED FEATURES, AND A FIRST-FLOOR PRIMARY SUITE! This Chesapeake home offers a combination of comfort, functionality, and potential financing advantages worth exploring. The bright, inviting kitchen features stainless steel appliances, updated cabinetry, and granite countertops, while water-resistant laminate flooring, ceramic tile, updated lighting, and ceiling fans add appeal throughout the home. The spacious first-floor primary suite features a vaulted ceiling, creating an open and relaxing retreat with an exceptional walk-in closet. Step outside to enjoy the deck and outdoor space, great for unwinding or entertaining, with the added convenience of a detached garage for parking, storage, or hobbies. If you're searching for an updated Chesapeake home with a first-floor primary suite and outdoor living space, this property deserves a closer look!

1221 Commerce Avenue, Central Chesapeake

$275,000

2 Beds ⋅ 2 Baths ⋅ 10657817 MLS

Welcome to highly sought-after, single-story living in the wonderful 55+ community of One Ford Place! This beautifully maintained Western Branch condo offers the ultimate "no-maintenance" lifestyle. The inviting layout features a spacious great room with sliding doors opening to a private patio. The well-appointed kitchen includes a pantry and conveys with all appliances. Enjoy a luxurious primary suite adorned with picture frame molding and a beautiful en-suite bath featuring a granite double vanity, tub, and separate shower. A second bedroom and full bath on the opposite side of the home create the perfect private guest suite! Enjoy the rare convenience of a one-car garage, a two-car driveway, and ample guest parking. Move in with total peace of mind thanks to major recent updates to the HVAC, water heater, and appliances. With TVs conveying and additional furniture negotiable, your transition will be a breeze. Located minutes from the YMCA, I-664, and I-164!

3301 Settlement Court, West Chesapeake

$262,500

2 Beds ⋅ 1 Baths ⋅ 10657727 MLS

Big backyard. Beautiful updates. Small price tag! Who says homeownership has to break the bank? Welcome to this charming 2 bedroom, 1 bath home in Loxley Gardens, offering the opportunity to own a move in ready home for under $300K! Enjoy a cute kitchen with brand new appliances, new flooring, a new roof, and new siding. The real showstopper? A MASSIVE backyard with endless possibilities for entertaining, pets, gardening, or creating your own outdoor oasis. Whether you're a first time buyer or looking to downsize, this one checks the boxes! Schedule your private tour today!

2432 Youngman Road, South Chesapeake

$360,000

3 Beds ⋅ 2 Baths ⋅ 10657719 MLS

Welcome to 3019 Roundtable Drive. A charming ranch-style home in the heart of Chesapeake. This 3-bedroom, 2-bathroom home offers an open layout everyday life or entertainment. recent updates include granite countertops w/backsplash in kitchen, new Roof, HVAC-2026, Hot water Heater-2026 and fresh paint throughout home. Outside, there’s a large backyard that offers plenty of space for entertaining, gardening, or play. Conveniently located on a quiet cul-de-sac near shopping, dining, and local amenities, this home is ready to welcome you. Fence and shed convey as is. Schedule your showing today!

3019 Roundtable Drive, South Chesapeake

1253 Quarter Path Trail, South Chesapeake

$365,000

3 Beds ⋅ 2 Baths ⋅ 10657920 MLS

Located on a quiet cul-de-sac in a highly desirable Turtle Rock neighborhood, this property offers privacy, a peaceful setting ideal for buyers seeking a home in an established residential community! The spacious rooms with a backyard that overlooks the water sets this home apart. Just minutes away from Greenbrier shopping and restaurants while also close to major roadways and military bases this home has the location and shine for all to see!

1253 Quarter Path Trail, South Chesapeake

$650,000

4 Beds ⋅ 2.1 Baths ⋅ 10657605 MLS

Welcome home to sought after Etheridge Lakes! Nestled at the end of a cul-de-sac, this move in ready home in the Hickory school district has it all! Newer LVP flooring on first floor, granite counters, SS appliances, breakfast area, formal living and dining and sunroom overlooking the large backyard. The primary bedroom has an additional flex room - perfect as an office, nursery, exercise or sitting room. Primary bath recently updated, driveway extended, 30-amp electric added for RV, all surrounded by a white picket fence! See this one first!

806 Crosswood Court, South Chesapeake

$375,000

4 Beds ⋅ 3 Baths ⋅ 10656923 MLS

2406 Drum Creek Rd, Chesapeake VA 23321 is a 1,288-square-foot home built in 1962. A fireplace anchors the main living area, adding warmth and ambiance to the central gathering space. The primary bathroom includes double sinks for everyday convenience. Outdoors, a storage shed adds extra utility. This residence combines practical design with comfortable living spaces, delivering functional amenities throughout every room.

2406 Drum Creek Road, West Chesapeake

$415,900

3 Beds ⋅ 2.1 Baths ⋅ 10657874 MLS

Welcome to this beautifully maintained home in the highly sought after Cardinal Meadows neighborhood! A bright, open layout designed for comfortable everyday living and effortless entertaining. The kitchen features granite countertops, ample workspace, and flows seamlessly into the main living areas. Natural light throughout creates a warm and inviting atmosphere. Move-in ready and waiting for its new owners, this home offers the perfect combination of comfort, style, and functionality. Enjoy added privacy and peace of mind with a fully fenced backyard, featuring a low-maintenance vinyl privacy fence- perfect for pets, entertaining or relaxing outdoors.

1625 Redwing Arch, South Chesapeake

$197,500

3 Beds ⋅ 1.1 Baths ⋅ 10657866 MLS

Spacious 3-bedroom, 1.5-bath home in the heart of South Norfolk offering over 1,300 sq ft of living space. Property needs some TLC but presents tremendous potential for investors or buyers looking to build equity. Bring your vision and really make this home shine! Conveniently located near dining, shopping, the interstate, and more! Call today for more information and to schedule your tour!

710 B Street, Central Chesapeake

$379,900

4 Beds ⋅ 3.1 Baths ⋅ 10657809 MLS

Situated in Chesapeake's Norfolk Highlands neighborhood, this 4-bedroom, 3.5-bath home offers approximately 2,000 square feet with a flexible floor plan and plenty of indoor and outdoor space to enjoy! Step inside to find inviting living and dining areas that flow into an updated kitchen featuring granite countertops, shaker-style cabinetry, stainless steel appliances, and a center island with additional seating. The flexible floor plan features two bedrooms on the first floor, including one with a private ensuite bathroom, and two additional bedrooms upstairs, one also featuring its own ensuite bathroom. This layout offers great options for guests, home offices, or multigenerational living. Recent improvements include updated bathrooms (2024), plumbing (2021), and fresh interior paint. An encapsulated, unfinished basement offers additional storage or workspace. Out back, the fully fenced yard is ready for entertaining with an above-ground pool, multiple decks, and a separate man shed with power, a bar, and a window unit. Additional highlights include dual driveways, an electric vehicle charging station, and a roof replaced in 2020. 3.5 PERC ASSUMABLE VA LOAN!! Incentives may be available through preferred partners. Contact the listing agent for details and eligibility.

1129 Hazel Avenue, Central Chesapeake

$415,000

3 Beds ⋅ 2.1 Baths ⋅ 10657801 MLS

Welcome to 458 Blue Beech Way! This spacious 3-bedroom, 2.5-bath home offers a flexible floor plan with two primary suites—one conveniently located on the first floor and another upstairs. The living area features a cozy gas fireplace, while the generous walk-in attic provides abundant storage and potential for additional finished living space, subject to buyer verification and applicable approvals. Enjoy the amenities of this desirable community, including three scenic lakes with fountains, a community pool and clubhouse. Conveniently located near shopping, dining, entertainment and major roadways. This home offers comfort, flexibility and plenty of potential. Schedule your showing today

458 Blue Beech Way, South Chesapeake

$233,500

2 Beds ⋅ 2 Baths ⋅ 10657659 MLS

Low-maintenance living with a little poolside fun? Yes, please! Welcome to this beautifully maintained 2-bedroom, 2-bath condo in Chesapeake. Tucked away in a quiet corner location, this home offers comfortable living with the convenience of easy interstate access. Enjoy peace of mind with an HVAC system just 3 years old and a water heater only 1 year old. The community pool is included with the HOA, making it easy to enjoy a little fun in the sun without the upkeep. One assigned parking space plus plenty of visitor parking adds to the convenience. Well cared for and ready for its next chapter, this condo is a charming place to call home!

710 Rue Marseille, 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.