Chesapeake VA Real Estate | Chesapeake VA Single Family Homes for Sale

Pristinely kept home on over 3 Acres located in the highly sought-after Hickory School District! This move-in-ready home has been meticulously cared for with major system upgrades including a 3- year old roof, all new siding, a rebuilt HVAC package unit with all new components, two water heaters, a whole-house generator and updated windows and gutters! The renovated kitchen (2017), main room refinished hardwood and recently updated Primary bedroom set this home apart! Enjoy outdoor living on the Trex decking and rest easy knowing the septic system was cleaned and pumped in January 2026. With extensive updates, exceptional maintenance, and a prime location in the Hickory area of Chesapeake, this home offers the perfect combination of comfort, efficiency, and long-term value with land to go with it! Come see your new home today!

2020 Sanderson Road, South Chesapeake

$499,000

3 Beds ⋅ 2.1 Baths ⋅ 10658040 MLS

Welcome home to this renovated, turnkey retreat in southern Chesapeake's sought-after 23322 zip code. Nestled along peaceful Long Ridge Road, this property offers the best of both worlds: scenic, country-style tranquility with quick access to the conveniences of Great Bridge and Hickory, top-rated schools, and nearby waterways. Inside, enjoy 3 spacious bedrooms and 2.5 stylishly refreshed baths. The bright interior showcases fresh neutral paint, durable luxury vinyl plank flooring, and plush new carpet. The redesigned kitchen features crisp new cabinetry, gorgeous countertops, and modern finishes, while every bathroom has been upgraded with chic new vanities. Major systems are fully addressed with a brand-new septic system installed in May 2026 for ultimate peace of mind. A perfect blend of worry-free rural charm and contemporary living!

941 Long Ridge Road, South Chesapeake

2035 Christian Avenue, Central Chesapeake

$310,000

3 Beds ⋅ 2.1 Baths ⋅ 10657931 MLS

Discover the perfect place to call home in this inviting 3 bedroom, 2.1 bathroom home! Featuring an open concept layout great for everyday living and entertaining, spacious closets for all your storage needs, and a fenced backyard great for outdoor enjoyment, this home offers comfort and convenience. Enjoy a convenient location near a variety of amenities, shopping, dining, and recreational activities. Whether you're looking for a place to relax or entertain, this home is ready for its next chapter with you!Don’t miss your opportunity to make it yours today!

2035 Christian Avenue, Central Chesapeake

$605,000

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

$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

$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

$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

$259,900

2 Beds ⋅ 1 Baths ⋅ 10657727 MLS

MUST SEE! Beautiful move-in ready home with fantastic updates, including a new roof, siding, flooring, appliances, fresh paint, and more. Features spacious bedrooms, an open-concept layout, and a great kitchen. Situated on a large lot (nearly 6,800 sq. ft.) with a massive backyard offering endless possibilities. Conveniently located near shopping, dining, military bases, and the airport. 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

$615,000

3 Beds ⋅ 2.1 Baths ⋅ 10657862 MLS

Welcome to this truly custom-built home in the highly desirable Hunningdon Woods neighborhood nestled in the heart of Greenbrier! Situated on a beautiful corner lot, this charming home offers a wonderful blend of comfort, character, and thoughtful design. The inviting living area flows into a lovely eat-in kitchen, creating the perfect setting for everyday living and entertaining. The spacious first-floor primary suite offers comfort and convenience, while the generously sized other bedrooms provide plenty of room for family or guests. Enjoy relaxing on the screened porch overlooking a beautifully landscaped yard filled with absolutely stunning array of blooming perennials that provide color and beauty throughout the seasons. Complete with a side-load garage, this special home offers timeless appeal. A wonderful opportunity to make this exceptional property your own.

1324 Cambridge Way, 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! Inside, 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

$380,000

3 Beds ⋅ 2 Baths ⋅ 10657636 MLS

Welcome to this beautifully maintained 3-bedroom, 2-bath ranch offering comfortable single-level living! This inviting home features hard-surface flooring throughout, a kitchen with new granite countertops, and a functional layout designed for everyday living. Step outside to enjoy the fully fenced backyard with privacy fencing, offering a wonderful space for outdoor entertaining, gardening, or simply relaxing. An attached one-car garage provides additional parking and storage. With thoughtful updates, easy maintenance, and desirable features throughout, this home offers the perfect combination of comfort and convenience!

1453 Debbs Lane, South Chesapeake

2711 Lake Drummond Cswy, South Chesapeake

$625,000

4 Beds ⋅ 2.1 Baths ⋅ 10657073 MLS

** INCREDIBLE OPPORTUNITY ** An exceptional combination of space, privacy and versatility awaits on nearly 4 acres with this beautifully refreshed 4-bedroom, 2.5-bath home! Has the following FEATURES: Freshly Painted throughout, Large Family Room with a Wood Burning Fireplace, New LVP Flooring, Great Kitchen with a Full Stainless Steel Appliance Package, wrap around bar and Eat-In Breakfast Area, Formal Dining Room and MORE!! Additional HIGHLIGHTS: 4 comfortable Bedrooms along with a LARGE FROG (Finished Room Over Garage) that offers exceptional versatility as possible media or recreation room, home office, playroom, hobby space, guest area or whatever best suits your needs, 2 Car Attached Garage, generous rear deck provides an ideal setting for morning coffee, afternoon relaxation or memorable gatherings with family and friends. Step outside and discover the true appeal of this expansive nearly 4-acre property. There's plenty of room to enjoy the peaceful surroundings, entertain outdoors, garden, play, accommodate pets or simply relax and enjoy the privacy and freedom that come with owning a larger homesite. With its beautiful setting, spacious living areas and nearly 4 acres of land, this is a rare and truly special opportunity that offers the space, flexibility and lifestyle you've been looking for!

2711 Lake Drummond Cswy, South Chesapeake

$499,900

4 Beds ⋅ 2 Baths ⋅ 10657378 MLS

Well maintained all brick ranch on a large .34 acre corner lot in the Hickory School District . Enter the large greatroom through foyer which opens to formal dining room. Greatroom features chairrail, wainscoating, exposed beams, built in bookcase and masonry wood burning fireplace.Kitchen has been updated with new cabinet faces, countertops and laminate floors; all appliances convey. Primary bath updated with new vanity, toilet and has tile floor. Hall bath updated with new toilet. Laundry closet convenietly off eat-in area in kitchen. Large frog has plenty of head space and large closet; partially floored walk in attic. HVAC, hot water heater newer, encapsulated crawl with dehumidifier. Large deck off greatroom. No neighborhood fees.

628 Gladesdale Drive, South Chesapeake

$549,900

3 Beds ⋅ 1.1 Baths ⋅ 10657745 MLS

Well-maintained, move-in-ready brick ranch in an established neighborhood with wide sidewalks! Features attractive LVP flooring throughout, three bedrooms, and a primary suite with a walk-in closet. Enjoy the gas log fireplace and additional storage with floored attic space. The converted attached garage is currently equipped as a beauty salon with styling station, shampoo sink, built-in cabinetry, and laundry area. A bright 20' x 20' sunroom with three walls of casement windows overlooks the backyard. Outdoor amenities include a 20' x 20' composite deck, fenced yard, and a 20' x 40' in-ground pool with cover. The detached three-bay garage includes power, workbenches, and pull-down access to a large, floored attic. A rare combination of comfort, functionality, and exceptional indoor and outdoor living space.

616 Rutherford Drive, South Chesapeake

$489,900

4 Beds ⋅ 2 Baths ⋅ 10657404 MLS

Welcome to sought-after Riverwalk! This beautifully maintained 4-bedroom, 2-bath ranch sits on a desirable corner lot with great curb appeal. The freshly painted interior offers an inviting floor plan, vaulted ceilings, updated lighting, luxury vinyl plank flooring, and thoughtful custom touches, including enhanced closet space and added shelving. The kitchen features quartz countertops, stainless steel appliances, and two pantries. A versatile 4th bedroom/FROG above the 2-car garage offers flexible space for guests, an office, or hobbies. Enjoy the beautifully landscaped backyard with a deck and paver patio, perfect for outdoor entertaining. Riverwalk amenities include a clubhouse, pool, dock, boat ramp, playground, trails, tennis and pickleball courts, plus seasonal concerts and food trucks. Discover the charm, convenience, and lifestyle that make Riverwalk a wonderful place to call home!

443 Supplejack Court, South Chesapeake

$885,990

6 Beds ⋅ 5 Baths ⋅ 10657735 MLS

QUICK MOVE-IN! Welcome to the Summit floor plan, a spacious and thoughtfully designed home offering exceptional living space across three finished levels. The main level features a private first-floor bedroom with full bath, plus a versatile office or formal dining room. At the heart of the home, the upgraded kitchen showcases an oversized island, premium quartz countertops, soft-close cabinetry, walk-in pantry, and stainless-steel appliances, including a wall oven with built-in microwave and gas cooktop. The kitchen flows seamlessly into the inviting great room, complete with a gas fireplace. Upstairs, retreat to the luxurious owner’s suite featuring a huge walk-in closet, dual vanities, relaxing soaking tub, and separate shower. Three additional spacious bedrooms, two full baths, a convenient laundry room, and an open loft provide plenty of flexible space. The finished basement adds even more possibilities with a recreation room, media room, and additional bedroom suite. Enjoy a welcoming community complete with walking trails and a fire pit. Incredible incentives with use of preferred lender! Photos and renderings are from the builder’s library; actual finishes and features may vary.

1268 Kidbrooke Street, South Chesapeake

3616 Riverwood Crescent, South Chesapeake

$750,000

4 Beds ⋅ 3 Baths ⋅ 10657714 MLS

COUNTRY LIVING AT ITS BEST!Imagine sipping your morning coffee while deer graze in your backyard! This incredible 3-acre property in desirable Hickory/Grassfield offers privacy, space, and endless possibilities!2,200 sq ft home with 4 bedrooms and 3 fully renovated bathrooms, a cozy wood-burning fireplace, new waterproof laminate flooring throughout, and a 2-car attached garage.The 1,500 sq ft workshop features a vehicle lift — perfect for car enthusiasts, hobbies, or business needs!Enjoy one of the largest above-ground pools available, extensive decking, and a recently repaired and painted shed.Additional features include newer HVAC and appliances, an excellent water softener, and a sealed crawlspace with dehumidifier and warranty.Not in a designated flood zone!Three acres, a spacious heated workshop, and your own private backyard oasis in the sought-after Hickory/Grassfield school district!Country charm, modern comforts, and room to live your way!

3616 Riverwood Crescent, South Chesapeake

2008 Pocaty Creek Lane, South Chesapeake

$889,500

4 Beds ⋅ 3.1 Baths ⋅ 10657656 MLS

Enjoy a slower pace of life as you relax on the front porch w/ morning coffee or watch loved ones play in the expansive yard. This beautifully remodeled farmhouse-style home sits on approx. 5.207 acres, extensively updated in 2021.Step inside to a dramatic 2-story foyer that opens to a spacious living area kitchen, dining, & family room, ideal for everyday living & entertaining. The 1st-floor primary suite offers comfort & convenience. Upstairs, you'll find a generous flex space perfect for a 2nd living area, home office, playroom, or gym. The 2nd level also features a second bedroom suite w/ private bath, plus 2 more bedrooms connected by a Jack/Jill bath. Abundant storage can be found throughout the home. The outdoor lifestyle is just as inviting. Spend your days fishing in your private pond, harvesting produce from the garden, or enjoying peaceful views of the neighboring horse farm from your kitchen window, at the end of the day, unwind by the pool.

2008 Pocaty Creek Lane, South Chesapeake

$436,500

5 Beds ⋅ 2.1 Baths ⋅ 10657607 MLS

Seller will pay up to $12,000 in CLOSING COSTS using our preferred lender & attorney. MOVE IN READY. Brand new 19 home subdivision includes underground utilities, curb & gutter and SIDEWALKS! Stunning New Construction! Welcome to this beautiful 5-bedroom, 2.5-bath home offering 1,862 square feet of modern living space. Designed with a spacious open floor plan, it's perfect for entertaining & everyday living. Inside, the kitchen shines with soft-close cabinets, granite countertops & an Appliance package including Stainless Steel refrigerator, dishwasher, gas stove & microwave. Bathrooms have granite countertops & upgraded soft-close cabinetry for a cohesive, upscale look. Durable blend of LVP flooring and plush carpet. Primary bedroom features a tray ceiling and walk in closet. This brand-new home also features a 1 car garage, covered front porch & is the perfect blend of comfort, style, and convenience—don't miss your chance to own in the heart of Chesapeake!

903 Railroad Avenue, Central Chesapeake

$349,000

2 Beds ⋅ 1 Baths ⋅ 10657263 MLS

This 3 acre lot is great for your dream home! It can not be subdivided. Lot is established and has privacy for you and your animals. It has a huge 2 story, detached, approx. 4 car garage that has its own well and electricity. It has over 530 feet of road frontage, facing a pristine, stunning horse farm. The home that is on the property is fully gutted and can be torn down or remodeled and added on, to make your perfect home. The property is being sold as-is, as well as the septic and well is as-is. Call today for your private showing, this one will not last long!

3365 Benefit Road, South Chesapeake

$720,000

5 Beds ⋅ 2.1 Baths ⋅ 10657643 MLS

The Bellhaven at Riverview Landing by Wetherington Homes offers a flexible 4-5 bedroom floor plan with an open-concept layout designed for everyday living and entertaining. The kitchen flows seamlessly through the butler's pantry into the dining area, creating a functional and connected space. A thoughtfully curated list of standard features is included, along with optional upgrades to personalize the home. Choose your lot and design options. Enjoy a convenient, centrally located community with easy access to shopping, medical facilities, dining, major interstates, and area beaches. The property is situated in the Hickory school district, an ideal setting for those seeking accessibility and everyday convenience. Ask about our current incentives! Directions: Mt. Pleasant Rd. to Back Road to Intracoastal Way. Follow the Wetherington Homes signs.

MM Bellhaven, South Chesapeake

$613,900

3 Beds ⋅ 2.1 Baths ⋅ 10657357 MLS

To Be Built - MODEL 369 Scotland Ln. nestled in Greenbrier, Joseph’s Meadow built by renowned builder. The Lily Cottage welcomes you w/ full front porch, airy 10-foot ceilings, & beautiful hardwood floors throughout first floor. Designed for everyday living & entertaining, the open-concept layout seamlessly connects living room, dining area, & stunning chef’s kitchen w/ Cotton White 42" cabinets, 9-foot quartz island, custom hood, and oversized walk-in pantry. Mudroom and powder room conveniently tucked by 2-car garage. Upstairs, a sun-filled loft, bath dual sinks and separate tub/shower room, 3 spacious bedrooms and a large laundry room provide exceptional functionality. Private primary suite offers a custom walk-in closet and tiled spa bath w/ 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 haven.

381 Scotland Lane, South Chesapeake

$612,500

4 Beds ⋅ 2.1 Baths ⋅ 10657358 MLS

To Be Built - LOW Rate and NO PMI! Joseph’s Meadow MODEL GPS 369 Scotland Ln. Chesapeake. Nestled in Greenbrier come visit the newest community by renowned local builder. Lily Cottage welcomes you w/ a full front porch, airy 10-foot ceilings and hardwood floors entire first floor. Designed for 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 HUGE walk-in pantry. Mudroom and powder room are conveniently tucked away by 2-car garage. Custom stair detail takes you to FOUR bedrooms with hall bath w/dual sinks, private tub/shower and water closet. BIG 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. Easy living w/ professionally managed grounds ensures low-maintenance living, making your dream truly peaceful haven.

377 Scotland Lane, South Chesapeake

$1,199,000

5 Beds ⋅ 3.1 Baths ⋅ 10657504 MLS

Welcome home!! 28.18 private acres, 3,714 sq ft, 5 bedrooms, 3.5 updated baths, TWO primary suites, a detached 4-car garage & 20x30 workshop—all in Chesapeake’s sought-after Hickory area?! Yes! Here at 509 Ballahack Rd. Extensively improved inside and out, this one-of-a-kind property delivers the space, flexibility and freedom of country living with modern comfort. Abundant natural light fills the spacious living areas, while warm finishes and thoughtful updates create an inviting feel throughout. The kitchen is complemented by a butler pantry with granite countertop, cabinetry and additional storage, adding function for everyday living and entertaining. The rare dual-primary layout offers one suite on each level, both with private ensuite baths—ideal for multigenerational living, extended guests or added privacy. The main-level primary has been refreshed with new flooring, paint, lighting and hardware. Upstairs, the second primary features a showstopping spa-inspired ensuite with an oversized wet room, rainfall shower, body jets, two-person soaking tub, porcelain tile and polished marble mosaic. All 3.5 bathrooms have been updated with fresh flooring, lighting, paint, mirrors and hardware. Outside, enjoy a nearly wraparound front porch, expansive 20x40 composite deck, outdoor kitchen setup, custom fire pit, fruit trees, grape vines and 28+ acres to explore. Proven deer and turkey hunting is literally steps from your back door, with private shooting and archery areas already in place. The detached 4-car garage provides exceptional storage, while the 20x30 workshop features concrete flooring, lighting and its own electrical panel. Additional improvements include 33 solar panels, Level 2 EV charger, major electrical upgrades, crawlspace encapsulation, updated HVAC and a private well with NO monthly water bill. A rare combination of acreage, recreation, extensive improvements and flexible living in Southern Chesapeake. See attached Feature & Upgrade Sheet for even more! Some listing photographs have been staged by Artificial Intelligence.

509 Ballahack Road, South Chesapeake

$345,000

4 Beds ⋅ 2.1 Baths ⋅ 10657384 MLS

Welcome to this spacious two-story home offering a fantastic layout and incredible potential! The first floor features a formal living room, separate dining room, a cozy den, and a convenient half bath. Upstairs, you will find three comfortably sized bedrooms alongside a primary suite complete with its own private en suite bath. Excellent storage and parking are provided by the attached two-car garage. Situated in a prime location just minutes from shopping, local dining, entertainment, major interstates, and area bases. This property is a wonderful opportunity to bring a little elbow grease, add your personal touches, and truly make it your own. Call today to schedule your private showing! Some virtual staging utilized in pictures.

844 Parapet Road, South Chesapeake

$415,000

4 Beds ⋅ 2.1 Baths ⋅ 10657430 MLS

Welcome to 2716 Thomas St, located in Chesapeake's Deep Creek area. Built in 2007, this 4-bedroom, 2.5-bath home offers over 2,400 square feet of living space, with flexible room for a home office, guest room or hobby space. It's a newer build in an established neighborhood, near shopping, dining, schools and the Dismal Swamp Canal Trail. It also has convenient access to major roadways for an easy commute throughout Hampton Roads. This is a great opportunity to get space, comfort and a convenient location in one home. It's a place where everyday routines feel easy and there's always room for whatever comes next.

2716 Thomas Street, South Chesapeake

2207 Hampton Roads Parkway, West Chesapeake

$554,718

4 Beds ⋅ 2 Baths ⋅ 10657488 MLS

QUICK CLOSE AVAILABLE! This home is move-in ready and is waiting for your special touch to make it your very own home sweet home. 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. 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 3% CCA (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.

2207 Hampton Roads Parkway, West Chesapeake

$450,000

4 Beds ⋅ 2 Baths ⋅ 10657381 MLS

Welcome to this charming all-brick ranch home nestled on just over 5 acres. This 4 bedroom, 2 bath home offers the perfect blend of comfort, space and privacy. Featuring a spacious eat-in kitchen, welcoming living room with a cozy wood-burning fireplace, and a finished room over the garage that provides versatile living space--perfect for that 4th bedroom, office, playroom or recreation area. Enjoy the peaceful setting and ample acreage while still having a home designed for easy one-level living. A wonderful opportunity to enjoy country living!

1025 Taft Road, South Chesapeake

$670,000

4 Beds ⋅ 3 Baths ⋅ 10657170 MLS

Welcome to Las Gaviotas, where golf course living meets your own backyard oasis! This sprawling 4-bedroom brick ranch offers beautiful golf course and water views, impressive vaulted ceilings, exposed beams, and a stunning two sided fireplace connecting the great room and sunroom. The beautifully renovated kitchen features a large center island and gas cooktop, while the spacious primary suite offers peaceful views and a luxurious bath. Step outside to your private retreat featuring an inground pool with updated liner, hot tub, gorgeous new paver patio, and outdoor gas kitchen for entertaining! Additional highlights include updated bathrooms, kitchen, expansive laundry room, new fixtures, Updated Flooring and Paint, HVAC (2024), roof (2019), and new water heater. Seller to provide a clear termite and moisture letter. A rare opportunity to enjoy single level living, incredible outdoor entertaining, and scenic surroundings!

530 San Pedro Drive, South Chesapeake

$490,000

4 Beds ⋅ 2.1 Baths ⋅ 10657351 MLS

THIS HOME HAS BEEN COMPLETELY RENOVATED TO INCLUDE ALL NEW STAINLESS STEEL APPLIANCES, WINDOWS, GRANITE COUNTERTOPS, SIDING, AND LAMINATE FLOORING THROUGHOUT THE HOME. COME AND ENJOY YOUR NEW HOME.THIS WONT LAST, CALL 1800 SHOWINGTIME AND GO SHOW TODAY!!!!

753 Helmsdale Way Way, South Chesapeake

1004 Poquoson Crossing, South Chesapeake

$699,000

4 Beds ⋅ 2.1 Baths ⋅ 10657331 MLS

Excellent opportunity to own a wonderful home in most sought after Warrington Hall. Great floor plan with a first floor primary bedroom and custom bath with jetted tub and separate shower. Formal living room and dining area. Great room with fireplace. Kitchen with breakfast bar, granite countertops and stainless appliances. Laundry room. Oversized two car garage. Three additional bedrooms upstairs. Spacious closets. Very flexible floor plan. Spacious private fenced yard.

1004 Poquoson Crossing, South Chesapeake

$339,900

4 Beds ⋅ 2.1 Baths ⋅ 10657097 MLS

Welcome home! This 4 bedroom, 2.5 bathroom home in the heart of Chesapeake is waiting for you! With over 1,700 square feet, there’s ample space to make your own! The screen in deck opens to a spacious yard that is great for entertaining, gardening, or anything you’d like! The attached garage allows for the possibility for extra parking or storage space! Conveniently located with easy access to major highways, making commuting or travel a breeze! Call today for more information and to schedule your tour!

512 Bay Oak Drive, South Chesapeake

$549,900

4 Beds ⋅ 2.1 Baths ⋅ 10655533 MLS

Welcome to this beautiful four-bedroom, 2.5-bath home in the desirable Tunbridge Station neighborhood of Great Bridge! With nearly 2,600 square feet of living space, this home offers plenty of room to live, relax, and entertain. Situated on a spacious corner lot in a quiet neighborhood, this home features wood flooring throughout the first floor and new LVP flooring on the second floor. The kitchen offers a cozy eat-in area with a bay window, while the separate living room provides added privacy and could also serve as a home office. A formal dining room offers the perfect space for hosting family and friends. One of the home's standout features is the oversized family room over the garage, offering endless possibilities for a media room, game room, or playroom. Enjoy outdoor living with a new deck and patio for relaxing or entertaining. Located in the sought-after Hickory school district, this home offers space, versatility, and a wonderful opportunity to enjoy all that Great Bridge has to offer.

911 Charing Cross, South Chesapeake

$470,000

4 Beds ⋅ 2.1 Baths ⋅ 10657309 MLS

Welcome home to this desirable Driftwood Meadows property! Step inside to a spacious living room featuring a cozy gas fireplace and abundant natural light. The updated kitchen offers quartz countertops, stainless steel appliances, a pantry, and a charming eat-in breakfast area with built-in bench seating and wraparound windows overlooking the expansive backyard. The primary bathroom features updated flooring and a new tub/shower (2025), while the upstairs guest bathroom offers updated flooring and a new toilet. Step outside to the freshly painted back porch, perfect for relaxing or entertaining. Additional highlights include all-new plumbing throughout the home (December 2022), a spacious two-car driveway, and a private setting tucked away toward the back of the neighborhood. Conveniently located near shopping, dining, entertainment, and easy access to Interstate 64. Don't miss the opportunity to make this home yours!

176 Driftwood Drive, South Chesapeake

$309,900

3 Beds ⋅ 2 Baths ⋅ 10657054 MLS

Welcome home to this charming three-bedroom, two-bath brick ranch nestled on a large, fully fenced lot in a quiet neighborhood. The bright, open kitchen features an island breakfast bar, creating a welcoming space for everyday living and entertaining. Three good-sized bedrooms provide comfortable living space, while no carpet anywhere in the home makes upkeep easy. Updated bathrooms and a spacious laundry room complete this wonderful home, making it an ideal choice for a first-time buyer or someone looking for a forever home . Outside, enjoy a spacious fenced backyard with planting beds, offering room to garden, relax, play, or entertain. Conveniently located near major freeways and military bases, this home combines peaceful neighborhood living with easy access to the surrounding area.

1507 Linden Avenue, Central Chesapeake

$699,900

5 Beds ⋅ 3.1 Baths ⋅ 10657221 MLS

Private upstairs living quarters, a wooded backyard, & a flexible multigenerational layout define this inviting ranch-style home. The suite over the garage includes a bedroom, full bath, great RM, & large walk-in attic, offering a comfortable retreat with added independence for guests or extended household living. On the main level, the gourmet kitchen features abundant granite counter space, generous cabinetry, a pantry, S/S appliances, & a gas range. Vaulted ceilings enhance the bright, open great RM. The primary suite offers a spa-inspired bath with soaking tub, oversized tiled walk-in shower, double vanity, & spacious walk-in closet. Two additional bedrooms share a full bath. Relax on the screened porch & enjoy exceptional privacy surrounded by the wooded backyard. Designed for comfort, connection, & flexibility, this home adapts beautifully to the way you live.

1421 Gemstone Lane, South Chesapeake

1318 Bainbridge Boulevard, Central Chesapeake

$479,900

4 Beds ⋅ 3 Baths ⋅ 10657296 MLS

NEW CONSTRUCTION. Welcome home to this beautifully designed 4-bedroom, 3-bath residence offering modern style and exceptional comfort. The open-concept floor plan features 9-foot ceilings, a spacious family room with a cozy gas fireplace, and a stunning kitchen with granite countertops, stainless steel appliances, and abundant cabinet space. A first-floor bedroom with a full bath is ideal for guests or multi-generational living. The luxurious primary suite offers an oversized tiled shower, double vanity, and a large walk-in closet. Generous secondary bedrooms, ample storage, pull-down attic access to a full attic, front and back yard sod. Energy Star double-pane windows, and extensive insulation provide year-round efficiency and comfort. Completing this exceptional home is a detached 2-car garage with electricity and plenty of additional storage.

1318 Bainbridge Boulevard, Central Chesapeake

$550,000

4 Beds ⋅ 2.1 Baths ⋅ 10657158 MLS

Location, Size and Schools...what more can you ask for! Nestled on a spacious lot in a desirable cul-de-sac setting, this wonderful 4-bedroom, 2.5-bath home offers 2,560 square feet of comfortable living space, well designed for everyday living... indoors and out. Come inside and discover a welcoming floor plan which includes a separate living and dining room, a Large eat-in chef's kitchen that opens seamlessly to the family room, creating the perfect gathering space for everything from casual mornings and memorable celebrations. Did I mention...No HOA...which means no restrictions or extra fees. With its generous living spaces, inviting layout, and exceptional lot, this home offers the lifestyle you've been looking for.

1504 Prospect Drive, South Chesapeake

Chesapeake VA Single Family Properties for Sale

Newest Chesapeake VA Single Family Homes for Sale

How much is your home worth?

How much is your home worth?

Virginia Licensed
Real Estate Brokerage

BBB Accredited
A+ Rating

5.0 ★ Google Rating

Live MLS Listings

Military Relocation

Waterfront Properties