Refine Search
Sort by
144 Downing Drive, South Chesapeake
$569,900
4 Beds ⋅ 3 Baths ⋅ 10655754 MLS
Going live on 10/8. Welcome to 144 Downing Drive in sought-after Hickory, Chesapeake! This spacious & well-maintained 4-bed, 3 full-bath, brick & vinyl ranch offers plenty of flexible living space on a .27-acre lot. The inviting great room features a vaulted ceiling & fireplace, while the spacious kitchen offers granite countertops, abundant cabinetry, stainless steel appliances, breakfast area, & bright sunroom. The finished room over the garage with a full bath offers excellent flexibility for an in-law suite, guest space, home office, or bonus room. Enjoy a fenced backyard built for entertaining with a deck & above-ground pool. Additional highlights include an attached 2-car garage & generous driveway parking space. Located in the desirable Tunbridge Station community with NO HOA and convenient access to Hickory schools, shopping, entertainment, dining, military bases, & major routes to get around Hampton Roads. Schedule your private showing today!

144 Downing Drive, South Chesapeake

708 Pebble Quay, South Chesapeake
$705,000
4 Beds ⋅ 3 Baths ⋅ 10655182 MLS
Unique custom built home on cul-de-sac with rare 3 car attached garage and extended driveway. This house was made for entertaining - 23' x 14' screened porch off family room for extended living space, along with a 22' x 20' pavilion - both with trek decking, finished wood ceilings, recessed lights and fans. Beautiful extensive landscaping with a stamped concrete walkway winding around house. Impressive 2 story entry has gorgeous chandelier. Dual staircases. Large kitchen includes granite counters, stainless steel appliances with gas stove, tons of cabinets and counterspace as well as deep pantry and eat-in nook. Formal living room and dining room with door leading to large front porch. First floor office in addition to 4 bedrooms upstairs. Full bathroom downstairs. Hardwood floors run through entire 1st floor. Primary bedroom includes corner gas fireplace, 13'x12.5' walk-in closet, and large bathroom with dual sinks and jetted tub . Laundry room has entire wall of cabinets with counter space and fold down ironing board. Lots of built in storage throughout, including a walk in climate controlled attic closet. The rare 3 car garage (owner actually has 4 cars in there!) is decked out for a car aficionado with LED lighting covering the ceiling and rubberized flooring. Additional outside shed. 16 hardwired cameras around exterior convey. Generator hook up in garage. Top of the line outside Charbroil kitchen conveys with acceptable full price offer. Neighborhood dock with boat ramp nearby. Very active River Walk Community Association centers around the beautiful clubhouse (which can be rented) and has a tennis/pickleball court w/pickleball league, garden club, swimming pool w/swim team, concerts in fall, food trucks and more, as well as parks and playgrounds. Tree lined walking paths wind through neighborhood along lakes with gazebos and fountains. Easy to hop on nearby Rt. 168 Chesapeake Expressway to easily get to any area of Hampton Roads.

708 Pebble Quay, South Chesapeake

1713 Sanderson Road, South Chesapeake
$1,300,000
4 Beds ⋅ 2.1 Baths ⋅ 10654856 MLS
Elegant custom details and room to live the life you’ve imagined! Sweeping down a long, paved driveway, this beautiful 4-bedroom home pairs comfortable country living with a thoughtfully arranged estate. Set on over 12 pristine acres in Chesapeake, zoned for Hickory schools, this property is a rare rural sanctuary. A wraparound porch welcomes you inside to 9' ceilings, 8' doors, and reclaimed knotty pine floors. The living room features a stone fireplace, opening to a bright kitchen with soft-close cabinets, Samsung Bespoke appliances, and butler’s pantry. Outside, enjoy a saltwater pool, fire pit, and private porches within a completely fenced in yard. The farm boasts a 6-stall barn with wash station, hot water, and mini-split, plus 5 watered pastures, 3 run-ins, and a 50x42 Morton building. An additional 1.5 acres offers potential for a riding arena or agriculture gardening, while a chicken coop, fruit trees, and berries complete the setting. Enjoy southern Chesapeake's rural character, with conveniences and Route 168 nearby.

1713 Sanderson Road, South Chesapeake

552 Saddlehorn Drive, South Chesapeake
$575,000
3 Beds ⋅ 2 Baths ⋅ 10654878 MLS
Set on approximately 1.5 beautiful acres, this well-maintained brick ranch offers comfortable living with room to enjoy the outdoors, pursue hobbies, and make it your own. Priced $10k under recent appraised value of $585k! Closing cost assistance and/or interest-rate buydown are negotiable with acceptable offer. Inside you’ll find 3 bedrooms and 2 full baths, custom closet systems, a thoughtfully designed kitchen with a large island and abundant cabinet storage, and a newly renovated mudroom/laundry room! A climate-controlled two-story attached 2-car garage/workshop provides space for vehicles, projects, and hobbies, with upstairs flex space for more options. Step outside and the property truly comes to life. Entertain, relax or just enjoy the privacy of your own space on the new deck. A raised bed garden, chicken run, grape arbors, barn, and storage shed add character and functionality. Located in desirable Hickory School District, just 20 minutes from Redmill and Landstown commons!

552 Saddlehorn Drive, South Chesapeake

1824 Lancing Crest Lane, South Chesapeake
$1,100,000
5 Beds ⋅ 4.1 Baths ⋅ 10654932 MLS
Welcome to an exceptional 4,800 sq. ft. all-brick home in Chesapeake's sought-after Grassfield area! Offering 5 bedrooms and 4.5 baths, this spacious home features a private primary wing designed as its own retreat, complete with an incredible oversized walk-in shower that truly has to be seen. Each additional bedroom is a suite with access to its own bath, providing privacy and comfort for family and guests. Enjoy outdoor living on the screened porch overlooking the inground pool with a fountain perfect for relaxing or entertaining. The community offers its own boat ramp and marina area with water access to the Elizabeth River. Conveniently located near shopping, dining, and interstate access, this home combines space, privacy, recreation, and an outstanding Chesapeake location.

1824 Lancing Crest Lane, South Chesapeake

1013 Baydon Lane, South Chesapeake
$550,000
4 Beds ⋅ 2.1 Baths ⋅ 10654935 MLS
Extremely well maintained home featuring a standout family room addition w/ floor to ceiling windows, vaulted ceilings, & a gas stove that creates a warm setting for winter days. This space overlooks the beautiful yard, established gardens, & a soothing water feature, offering a seamless connection to the outdoors. The living room includes a coved ceiling and a gas fireplace, with Brazilian walnut floors extending through to all bedrooms, the guest bath, and the primary bath. The eat in kitchen offers ceramic tile flooring and quartz countertops. The updated hallway bath serves two additional bedrooms. The primary bedroom includes a walk in closet, updated ensuite bath, and a flexible bonus space suitable for an office, nursery, or second closet. Outdoor highlights include a newer Trex deck with direct access to the newer hot tub, perennial landscaping that returns each year, and a private yard designed for relaxation. Updates include HVAC (2021) and a mini split in the FROG (2020).

1013 Baydon Lane, South Chesapeake

708 Colony Drive, South Chesapeake
$465,000
4 Beds ⋅ 2 Baths ⋅ 10654846 MLS
Buyer may receive a lender credit of up to 1.25% of the loan amount toward eligible closing costs with the use of the sellers preferred lender. Hickory schools, no HOA, and a quiet Chesapeake neighborhood, 708 Colony Drive has a lot to love before you even step inside. This updated 4-bedroom, 2-bath home offers primarily one-level living with three bedrooms on the main floor and a true fourth bedroom with a closet above the garage. The open layout flows from the spacious living and dining areas into an updated kitchen featuring quartz countertops, brass fixtures, a large sink, stainless steel appliances, and modern finishes. Both bathrooms have also been beautifully updated with tile and fresh finishes throughout. Outside, enjoy a fully fenced backyard with a deck that’s perfect for entertaining, relaxing, or pets. An attached one-car garage, two-car driveway, and additional parking provide plenty of space. Located in an established, quiet neighborhood with no HOA and sought-after Hickory schools, this move-in-ready home offers the updates you want with the freedom and location that can be hard to find in Chesapeake.

708 Colony Drive, South Chesapeake

1248 Kidbrooke Street, South Chesapeake
$881,140
6 Beds ⋅ 5 Baths ⋅ 10654587 MLS
Welcome to The Summit, where you’ll discover thoughtfully designed living space across 2 luxurious floors. The main level impresses with a versatile 1st-floor bedroom and full bath, a flexible office or formal dining room, and a sunlit great room that flows seamlessly from the kitchen, featuring a large island, quartz countertops, soft-close cabinets, premium stainless steel appliances (including double ovens and a gas cooktop),and a walk-in pantry. Upstairs, unwind in your expansive owner’s suite with a huge closet, double vanities, a relaxing bathtub, and a separate shower, while three additional bedrooms, two full baths, a laundry room, and a loft provide ample space and flexibility. The home is complete with a walk-out basement. Enjoy a vibrant community with walking trails and a fire pit, all within reach of Chesapeake’s scenic waterways, local festivals, and easy access to Virginia’s beaches. Photos are from builder's library, actual finishes and finishes may vary.

1248 Kidbrooke Street, South Chesapeake

732 Colonel Byrd Street, South Chesapeake
$799,900
6 Beds ⋅ 4 Baths ⋅ 10654449 MLS
Welcome to this beautiful home in the highly sought-after community of Culpepper Landing! Offering an impressive 3,656 square feet of living space, 6 bedrooms, 4 full bathrooms, and a dedicated office that provides the flexibility of a 7th room, this beautifully designed home delivers the perfect blend of space, comfort, and functionality. Step inside to discover an inviting open-concept floor plan, designed for everyday living and effortless entertaining. The kitchen is the heart of the home, showcasing custom cabinetry and a large center island creating a welcoming space for gatherings with family and friends. A convenient first-floor bedroom provides added flexibility for guests or multigenerational living. With generous living areas, a versatile layout, and plenty of room to spread out, this home is designed to accommodate a variety of lifestyles. Whether you're hosting memorable gatherings or enjoying a quiet evening at home, this spacious Chesapeake property has room for it all.

732 Colonel Byrd Street, South Chesapeake

620 Emerald Court, South Chesapeake
$379,900
4 Beds ⋅ 2.1 Baths ⋅ 10654385 MLS
Welcome to your next great opportunity! This spacious 1,917 sq ft ranch home offers 4 bedrooms and 2.5 bathrooms with a flexible floor plan designed for effortless daily living. The functional layout includes a large Finished Room Over Garage (FROG) as the 4th bedroom— could also be used as an office, media room, or flex space. Inside flows seamlessly to the back deck, overlooking an expansive 0.389-acre lot with abundant outdoor space and a large storage shed. Complete with a 1-car attached garage, this property offers incredible potential! Bring your vision—with a touch of sweat equity and minor cosmetics, this solid home will truly shine and build instant equity. Excellent location with convenient access to major interstates, regional bases, dining, shopping, and entertainment. Call today to schedule your private showing!

620 Emerald Court, South Chesapeake

744 Helmsdale Way, South Chesapeake
$425,000
4 Beds ⋅ 2.1 Baths ⋅ 10654335 MLS
Discover timeless charm in this beautiful, traditional home located in the heart of Chesapeake. Featuring 4 bedrooms, 2.5 bathrooms, and a spacious two-story layout, this home includes a bedroom with its own en suite bath, making it great for guests or added privacy. Gather around the cozy fireplace on cool evenings, or enjoy casual meals in the bright breakfast area. Step outside to a fully fenced backyard, great for entertaining, pets, or relaxing outdoors. Recent upgrades, including new siding and roof (2021) and a remodeled primary bathroom (2025), enhance both the home's beauty and value. An attached garage and attic complete this exceptional property. Don't miss your opportunity to make this Chesapeake gem your own!

744 Helmsdale Way, South Chesapeake

803 Gresham Way, South Chesapeake
$615,000
5 Beds ⋅ 3.1 Baths ⋅ 10654210 MLS
Space, space and more space! With over 3,600 square feet, this HOME gives you room to spread out, work, gather and entertain. Hardwood floors flow throughout the majority of the home, while the spacious kitchen features granite countertops and stainless steel appliances. Do you work remotely? There’s a private first-floor office, too. Outside, enjoy an in-ground saltwater pool, Trex deck and gazebo for pool days, cookouts and relaxing at home. And there’s more—the detached garage is ideal for a workshop, hobby space, teen retreat or extra storage. Pool, detached garage, first-floor office, cul-de-sac and no HOA—all wrapped into one very spacious home. If space and flexibility are at the top of your list, this one deserves a look!

803 Gresham Way, South Chesapeake

609 Fairfield Drive, South Chesapeake
$849,900
4 Beds ⋅ 2.1 Baths ⋅ 10654253 MLS
The perfect farmhouse that’s a mix of privacy and closeness to local amenities. Sitting on approx 3 acres in Albemarle Farms, this home offers the updates you've been looking for. Step inside to a bright, welcoming interior with engineered hardwood floors, fresh paint throughout, new trim, and a beautifully updated kitchen. Completed in 2025, the kitchen features all-new cabinetry, quartz countertops, a large island, white stone backsplash, new appliances, and a new sink and faucet. Just beyond, the great room is centered around a new stone fireplace and mantle, while the 4-season room offers a flexible space to relax, work, or enjoy views of the property. Upstairs, the primary suite features a soaking tub and walk-in shower, with two additional bedrooms and bonus space offering plenty of flexibility. Major improvements include new heating and cooling units, new ductwork upstairs and downstairs, a new tankless water heater, and new downstairs subfloor. Outside is where this property really shines, with a saltwater in-ground pool, expansive deck, covered rear porch, circular driveway, and plenty of room to enjoy the wooded setting. An oversized garage with a finished room above adds even more usable space. Located in the Hickory school district with no HOA, this is a home with room to settle in, spread out, and enjoy both indoors and out. Incentives may be available through preferred partners. Contact listing agent for details and eligibility.

609 Fairfield Drive, South Chesapeake

1733 Head Of River Road, South Chesapeake
$839,900
4 Beds ⋅ 3 Baths ⋅ 10654135 MLS
Interior pics coming!! Welcome to the Hickory lifestyle, where space, privacy, & possibilities come together on 3 acres! This 4-bedroom, 3-bath home offers 2,912 square feet of comfortable living space & plenty of room to enjoy the outdoors. The kitchen features granite countertops & opens to the family room, creating an easy gathering space for everyday life. A formal living room & additional space provide room for an office, playroom, library, or whatever fits your needs. Upstairs, all four bedrooms are generously sized, including a spacious primary suite with a large bathroom featuring a separate walk-in shower & soaking tub & 2 walk-in closets! Outside, the in-ground pool sets the stage for relaxing afternoons at home. And with 3 acres to call your own, there’s room to dream—whether that means a vegetable garden, chickens, outdoor hobbies, or simply enjoying the extra elbow room that makes Hickory living so desirable. Come see all this home & its expansive setting has to offer!

1733 Head Of River Road, South Chesapeake

1085 Bells Mill Road, South Chesapeake
$415,900
4 Beds ⋅ 2 Baths ⋅ 10653838 MLS
Welcome home to 1085 Bell Mill Rd.! This beautifully refreshed 4-bedroom, 2-bath Chesapeake home is move-in ready and filled with features you'll love. Fresh paint throughout creates a bright, inviting feel, while the updated kitchen and bathrooms add a modern touch. The cozy gas fireplace creates the perfect gathering spot in the living area. Step outside to enjoy the backyard, complete with established blueberry bushes and apple trees - a wonderful bonus for enjoying fresh fruit right at home. With comfortable living spaces, thoughtful updates, and a convenient Chesapeake location, this home offers the perfect blend of charm, functionality, and everyday living. Come see all this home has to offer!

1085 Bells Mill Road, South Chesapeake

1816 Sunsprite Loop, South Chesapeake
$600,000
6 Beds ⋅ 3 Baths ⋅ 10654192 MLS
It’s got space!! Use all 6 bedrooms or create the office, guest room, fitness space or playroom you've been looking for. The first floor offers a bedroom, adjacent flex room and modified curb less shower—great for guests or anyone who prefers fewer stairs. Neutral décor, 9' ceilings, hardwood floors, crown molding and a huge FROG. Spacious primary suite with hardwood floors and two walk-in closets, plus second-floor laundry. Outside, enjoy a lg, fenced backyard , detached shed, private well for lawn irrigation and attached 2-car garage. Meticulously maintained with annual HVAC, tankless water heater and crawl-space service contracts. Seller to provide termite/moisture letter. Convenient to Millville Rd. and Veterans Bridge. Annual Termite/Moisture contracts/ NO FLOOD INS. Grassfield High School has earned national recognition in US News and World Reports for VA’s Board of Education Highest Achievement Award / 2024. $5,000 Closing Cost Assistance. Original Owner.

1816 Sunsprite Loop, South Chesapeake

601 Lord Byron Court, South Chesapeake
$380,000
3 Beds ⋅ 2.1 Baths ⋅ 10653788 MLS
Welcome home to this stunning 3-bedroom, 2.5-bathroom gem nestled in one of Chesapeake's most serene and desirable neighborhoods. The main level boasts a bright and cozy living room that flows seamlessly into a stylish kitchen, making everyday living and entertaining a breeze. Upstairs, you will find spacious, private bedrooms and well-appointed bathrooms. Outside is a generous backyard that serves as your own private oasis, perfect for hosting weekend gatherings, gardening, or relaxing in the sun. Situated in a peaceful community just minutes from local shopping, dining, schools, and major commuter routes, this home truly has it all. Don't miss the opportunity to make this house your home sweet home! Schedule your private tour today! Listing photos contain virtually staged media.

601 Lord Byron Court, South Chesapeake

704 Woodcott Drive, South Chesapeake
$560,000
3 Beds ⋅ 2.1 Baths ⋅ 10654136 MLS
Welcome home to 704 Woodcott Drive. This beautifully refreshed 4 bedroom 2 1/2 bath home is full natural light and lovingly updates. The bright, inviting interior features new LVP flooring, new carpet, and fresh paint throughout, giving the home a beautiful, fresh feel. The updated kitchen is great for gatherings, with quartz countertops, stainless steel appliances, and a gorgeous double sided fireplace shared with the living room. The loft can be used as a flex room, office or media room. Enjoy the barbecues on the back deck overlooking the huge backyard. Make this the perfect spot to enjoy cozy evenings or entertaining family and friends. Seller to offer buyer 2/1 rate buy down as well as a new driveway with full price offer.

704 Woodcott Drive, South Chesapeake

415 Prince Phillip Court, South Chesapeake
$409,000
3 Beds ⋅ 2.1 Baths ⋅ 10654072 MLS
Welcome to this spacious 3-bedroom, 2.5-bath split-level condo in a great Chesapeake location near Oak Grove Park, the hospital, shopping, and interstate access. The mid-level foyer leads to the lower level, featuring a comfortable sitting room with a fireplace, access to the back deck and fenced backyard, a utility closet, two bedrooms with large closets, full hall bathroom, and access to the attached 2-car garage with a convenient garage door opener. Upstairs, the updated kitchen offers stainless steel appliances, a pantry, bar, and breakfast area with bench seating, along with a fireplace and built-in storage. The upper-level living room provides additional space for relaxing or entertaining. The spacious primary suite features a walk-in closet and ensuite bathroom with a granite vanity, built-in makeup table, jetted tub, separate shower, and water closet.

415 Prince Phillip Court, South Chesapeake

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.

How much is your home worth?

Get instant property value now!