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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

2410 Centerville Turnpike, South Chesapeake
$879,000
3 Beds ⋅ 2 Baths ⋅ 10655763 MLS
If these walls could talk, they would tell you 176 years of stories. Rare pre-Civil War farmhouse charm meets modern comfort in this private retreat that feels like a vacation every day. This 2-story home is filled with character, featuring 4 fireplaces, gorgeous original hardwood floors, 10-foot ceilings, hand-sawed original moldings, intricate ceiling details, and antique lighting. The living room offers a cozy wood-burning stove, while the family room showcases coffered ceilings and original hardwood floors. The spacious primary suite stands out with a beautiful fireplace and a wall of built-in cabinetry offering storage rarely found in modern homes. Enjoy two laundry areas, including one in the ADU over the detached tandem 4-car garage, plus a flexible space for an office or mudroom off the back of the main house. Outside, unwind and entertain by the pool oasis, or sit on the 250 sqft covered porch. There is a huge new chicken coop (26), and 2 dog runs for that farm life as well as a shed (as is). The brick walkways are the original bricks from the chimney repurposed. Updates include painted kitchen cabinets/walls (26), sealed and painted metal roof with 20 year paint (26), new pool liner (25), encapsulated crawlspace with dehumidifier/support beams (25), 50-gallon hot water heater (25), HVAC, and ductwork (23), new steps and railing out to the pool (26), breaker upgrade to house (25) 2 solar systems one to the main house and one to the ADU/garage (23). More updates listed in agent remarks. Near Hickory schools, shopping, Bypass, and OBX. Come own a piece of history in Hickory!

2410 Centerville Turnpike, South Chesapeake

3145 Codorus Street, South Chesapeake
$490,000
4 Beds ⋅ 2.1 Baths ⋅ 10655704 MLS
Seller is willing to negotiate CCA/rate buy down! VA Assumable rate of 2.875%. Beautifully updated and move-in ready, this home offers the perfect blend of comfort, style, and community. Recent improvements include luxury vinyl plank flooring throughout, a beautifully renovated primary bath with a spacious walk-in shower, and the addition of a fourth bedroom for added flexibility. Outside, the large backyard is framed by mature weeping willow trees, creating a peaceful retreat on a quiet side street. Beyond your front door, enjoy a lifestyle that’s hard to find—golf cart rides to the clubhouse, afternoons at the resort-style pool, workouts in the fitness center, visits to the dog parks and playgrounds, and a calendar full of neighborhood events including community picnics, book club, cigar & bourbon nights, festive holiday celebrations, and the beloved Christmas golf cart parade. Experience everything this vibrant, close-knit community has to offer in sought-after Culpepper Landing.

3145 Codorus Street, South Chesapeake

220 Marion Drive, South Chesapeake
$435,000
3 Beds ⋅ 2 Baths ⋅ 10655721 MLS
Location, Location, Location, Welcome to the desirable Great Bridge area of Chesapeake! This beautifully updated 3-bedroom, 2-bath home offers approximately 1,700 square feet of comfortable living space, with many of the major projects already completed. Inside, enjoy an inviting layout featuring a remodeled kitchen, refreshed bathrooms, new dishwasher 2026, 2019 AC system, and new 2025 evaporator coil. The cozy fireplace and chimney have also been professionally maintained, ready to enjoy. Outside, your private backyard retreat awaits! The inground pool is great for relaxing and entertaining, while the detached workshop offers versatile space for hobbies, projects, storage, or gatherings. The fully fenced yard provides privacy and plenty of room to enjoy. The home has been thoughtfully maintained, including 6-inch commercial gutters and professionally leveled and graded ground for proper drainage. The major mature trees around the home have been removed, reducing the potential for damage from falling limbs during severe weather. Additional improvements include a 2014 roof on all structures, plus a vapor barrier and dehumidifier installed in the crawlspace in 2019. The major work has been done—just unpack and enjoy! Come see everything this well-maintained Great Bridge home has to offer and schedule your private tour today.

220 Marion Drive, South Chesapeake

518 Whisper Walk, South Chesapeake
$439,900
4 Beds ⋅ 2.1 Baths ⋅ 10655312 MLS
Welcome home to this beautifully maintained condominium in the highly sought-after Cedar Crossing community. This spacious open concept residence offers over 2,000 square feet of comfortable living space. Four bedrooms featuring a large primary bedroom suite on first level, with double vanity and large walk-in closet. Beautiful hardwood floors, and crown molding throughout. Tile in kitchen, bathrooms and mudroom. Enjoy the privacy of a fenced backyard with storage shed for additional equipment. Two car garage and driveway space. Neighborhood has a well-equipped playground, swimming pool, tennis court and clubhouse. Enjoy low-maintenance living in a vibrant community conveniently located near shopping, dining, schools, and major commuter routes.

518 Whisper Walk, South Chesapeake

MM James 2, South Chesapeake
$720,000
5 Beds ⋅ 3 Baths ⋅ 10655465 MLS
Model Home to Be Built - James II Model at Riverview Landing by Wetherington Homes. This thoughtfully designed floor plan offers an Owner's Suite, two additional bedrooms, and a utility room conveniently located on the first floor. Buyers may select their lot and personalize available design options. The home includes a variety of well-appointed features designed to support modern living. The community offers eight floor plan options along with multiple exterior elevations that highlight architectural detail and curb appeal. Contact us today for additional information, to join the VIP interest list, and to schedule an appointment. Discover the opportunity to build in this thriving new community in Chesapeake!

MM James 2, South Chesapeake

204 Henry Jefferson Way, South Chesapeake
$709,990
4 Beds ⋅ 3 Baths ⋅ 10655470 MLS
The Savannah offers a well-designed floor plan with a spacious great room centrally located, creating a natural flow into the kitchen and dining area—great for everyday living and gatherings. The home features four generously sized bedrooms, including an owner’s suite positioned at the rear of the home for added privacy. The owner’s suite includes direct access to the covered porch and two large closets. A flexible space just off the foyer provides versatility for use as a home office, additional living area, or formal dining space, depending on your needs. The second floor includes an additional bedroom, a full bath, and a loft area, offering extra living options for guests or multi-functional use. Thoughtful layout and functional spaces make the Savannah a comfortable and adaptable home.

204 Henry Jefferson Way, South Chesapeake

1345 Oak Ridge Drive, South Chesapeake
$629,900
4 Beds ⋅ 2 Baths ⋅ 10655393 MLS
Welcome home to this charming 4-bedroom, 2-bath brick ranch nestled on 4.22 wooded acres at the end of a quiet cul-de-sac. Inside, you'll find a warm and inviting layout featuring a family room with a wood-burning fireplace, formal living and dining rooms, granite countertops, and beautifully updated primary and hall bathrooms. Step outside to relax on the new composite deck (2024), gather around the fire pit, or enjoy the peaceful wooded surroundings. The property also includes a detached 2-car garage with a finished studio apartment and full bath, plus a whole-house generator and water softener for added convenience. Offering space, privacy, and versatile living, this property is ready to welcome you home!

1345 Oak Ridge Drive, South Chesapeake

245 Old Drive, South Chesapeake
$410,000
3 Beds ⋅ 1.1 Baths ⋅ 10655362 MLS
THE OPPORTUNITY YOU'VE BEEN WAITING FOR! If you've been searching for a well-maintained home with space, character and room to make it your own, this is definitely the one. Situated on an oversized corner lot, this 3 bd, 1.5 bth home offers approx 1629 sqft, beautiful hardwood floors, generous living spaces and a layout with plenty of possibilities. Large room off of living room with a closet that can easily be a 4th bedroom, home office, gym, in-law suite with it's own separate side entrance. Large screened in patio leads to a HUGE backyard that can be transformed into an oasis offering room to entertain, garden or just relax. Workshop-like attached shed and a detached shed. It's move in ready and can be customized over time. No trendy renovations. No inflated renovation price tag. Just a solid home in a great location with great bones and the opportunity to add your own style. Located within blocks to shopping centers, dining, hospitals and interstates. Come see today!

245 Old Drive, South Chesapeake

3433 Martin Johnson Road, South Chesapeake
$385,000
3 Beds ⋅ 2 Baths ⋅ 10655347 MLS
Welcome to this charming 3-bedroom, 2-bath Cape Cod nestled on 1.4 private acres in the Deep Creek area of Chesapeake! This property offers the perfect blend of peaceful outdoor living and everyday convenience. Enjoy gardening in the fenced garden, unwind in the wooded backyard, or take advantage of easy access to the nearby Portsmouth Ditch Trail for walking, biking, and outdoor recreation. Inside, you’ll find a warm and inviting layout with classic Cape Cod character and plenty of space to make your own. Whether you’re looking for room to spread out, enjoy nature, or simply escape the hustle while staying close to shopping, dining, and major commuting routes, this home checks all the boxes. Don’t miss this unique opportunity to own your own slice of Deep Creek!

3433 Martin Johnson Road, South Chesapeake

841 Woodstream Way, South Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10655291 MLS
Beautifully maintained, thoughtfully updated, and a backyard you'll want to spend all of your time in! Step inside to a welcoming foyer filled with natural light and discover this inviting 4 bedroom, 2.5 bathroom home in a sought-after neighborhood within the Hickory School District. Updates include Brazilian hardwood, upgraded pet protect carpet padding, PEX plumbing, electrical, solar power, and an electric fireplace with a gas hookup for conversion. With solar, the electric bill averages approximately $70/month. Outside, enjoy a private backyard oasis with manicured gardens, stonework, raised vegetable beds, blueberry bushes, apple trees and even an underground invisible fence! A fully insulated detached workshop with electricity and A/C offers flexible spaces for hobbies, projects, a studio, or workspace. Have instant hot water with top of the line Rinnai tankless water heater! HUGE corner lot! Meticulously maintained inside and out, this charming home is ready to be called home!

841 Woodstream Way, South Chesapeake

101 Stadium Drive, South Chesapeake
$649,900
4 Beds ⋅ 3.1 Baths ⋅ 10655286 MLS
Welcome to your very own homesteader’s haven in the heart of Chesapeake! Tucked away on over an acre, this one-of-a-kind brick ranch offers a blend of modern comfort and timeless, back-to-the-land charm. Outside, you'll be greeted by a flourishing orchard with established fruit trees that provide a bounty through every season, blueberries, figs and plums for jam-making, crisp apples, cherries, peaches, pomegranates, and pecans for baking. Designed for self-sufficiency with two outbuildings, a 40’x45’ parking area ideal for your boat or RV, solar panels and a new roof provide energy savings. The fully finished converted garage for an in-law suite, playroom, fifth bedroom, business front, the choice is yours. If you’re dreaming of tending gardens and evenings under the trees enjoying the fruits of your own land, this property has it all. A true little piece of paradise, right in the city yet worlds away. This home also has an assumable VA mortgage at 4.9% interest for a VA eligible buyer! Perfect opportunity for owning a home in Chesapeake that meets all of your space needs, enjoying self sufficiency and all the convenience that Chesepeake has to offer.

101 Stadium 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

911 Intracoastal Way, South Chesapeake
$797,540
5 Beds ⋅ 3.1 Baths ⋅ 10655214 MLS
The Tillman offers 3,226 sq. ft. of stylish and flexible living - great for multigenerational living! This spacious home includes 5 bedrooms, 3.5 baths, and a 2-car garage. The first-floor primary suite provides the perfect retreat with a massive walk-in closet, dual vanities, and a private water closet. Upstairs, you’ll find a second primary-style bedroom with direct access to a full bath, offering comfort and privacy. Three additional bedrooms (each with walk-in closets), a large loft, and a convenient laundry room complete the second floor. The open-concept main level features a welcoming dining room, expansive kitchen with an oversized island and two pantries, including a Costco pantry, and a bright family room. Photos and renderings are from builder's library, actual finishes and features may vary.

911 Intracoastal Way, South Chesapeake

2609 Mossgate Court, South Chesapeake
$379,900
4 Beds ⋅ 2.1 Baths ⋅ 10652642 MLS
Opportunity knocks in Chesapeake! This property offers a chance to create something truly special in a desirable location. Bring your vision and your renovation plans to unlock the full potential of this home. The expansive lot is a standout feature, providing an abundance of space and endless possibilities for outdoor living, entertaining, gardening, recreation, or future improvements. Whether you're an investor searching for your next project or a buyer looking to build equity and make a home your own, this property is ready for its next chapter. Conveniently located near shopping, dining, schools, parks, major roadways, and everything Chesapeake has to offer. Properties with this much potential and land don't come around every day. Come see the possibilities for yourself! Schedule your showing today!

2609 Mossgate Court, South Chesapeake

1004 Cedar Tree Court, South Chesapeake
$679,580
4 Beds ⋅ 3 Baths ⋅ 10655160 MLS
Welcome to the Whitehurst model in Cedar Manor! Currently under construction with an estimated Spring 2027 completion, this stunning 2-story transitional floor plan offers 3,054 square feet of thoughtfully designed living space on a generous 0.68-acre corner lot with serene pond views. Featuring 4 or 5 spacious bedrooms, 3 full baths, and a desirable main-floor layout, this home boasts a primary bedroom suite on the first level complete with a spacious ensuite and walk-in closet. The light-filled interior includes a foyer, natural gas fireplace, open breakfast area, dedicated office/study or 5th bedroom, utility room with main-floor laundry, and a walk-in attic for abundant storage. Energy efficient features included a tankless gas water heater and radiant barrier. Enjoy cul-de-sac living conveniently near to top-rated Grassfield schools. Take advantage of seller incentives available when using the trusted lender. Contact us for full details, floor plans, and construction updates! Pictures from prior build. We have this floor plan to walk in another community!

1004 Cedar Tree Court, 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

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.

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