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1441 Whittamore Road, South Chesapeake
$455,000
5 Beds ⋅ 2 Baths ⋅ 10659859 MLS
Welcome to a rare opportunity in Chesapeake's sought-after Hickory school district! Set on a full acre, this beautifully transformed 5-bedroom, 2-bath home offers the space and setting to enjoy a touch of country living while staying near the conveniences of the city. The renovation goes far beyond cosmetics, with a new roof, siding, windows, HVAC, flooring, carpet, plumbing, septic tank, appliances and more. Inside, fresh modern finishes create a bright, move-in-ready home with room for everyone. Outside, the expansive acre lot opens the door to gardens, outdoor entertaining, hobbies, animals or simply having more room to enjoy the outdoors. With golf courses nearby and easy access to everything Chesapeake has to offer, this property delivers a unique blend of space, location and modern living. Nearly everything has been refreshed or replaced- just bring your furniture and start enjoying the Hickory lifestyle!

1441 Whittamore Road, South Chesapeake
1421 Saint Brides Road West, South Chesapeake
$849,900
4 Beds ⋅ 3.1 Baths ⋅ 10659781 MLS
1421 Saint Brides Rd West, the ASHBEE Model by Wetherington Homes. READY NOW! Situated on a wooded and private 16+ acre parcel in Southern Chesapeake, this spacious and open concept floorplan offers 4 Bedrooms PLUS AN OFFICE AND A LOFT! Great Room opens to Kitchen with large center island with overhang for extra seating, dining area, quartz counters, tile backsplash, pantry, and stainless appliances including refrigerator and double ovens. 1st floor Owner's Suite with extra large walk in closet with wood shelving and full bath with tile surround step in shower, soaking tub, tile flooring, double bowl vanity, quartz counters, and water closet. You will love the Covered Porch to enjoy the peaceful wooded setting! Add'l Details: LVP flooring on 1st floor; wood treads on stairs; carpeting in all bedrooms; quartz counters in full baths; 1st floor Laundry Room; Mud Room with Drop Zone; craftsman style doors & trim; stylish finishes; Front Porch, 2 car garage; and more!

1421 Saint Brides Road West, South Chesapeake
1630 Taft Road, South Chesapeake
$985,000
4 Beds ⋅ 3.1 Baths ⋅ 10658171 MLS
This is New Construction and Move-in Ready! Experience the a blend of luxury, space, and country charm in this stunning newly construction home situated on a picturesque 3-acre lot where horses are welcome. Offering approximately 2,957 square feet of thoughtfully designed living space, this two-story home features 4 spacious bedrooms, 3.5 baths, and an open-concept floor plan great for both everyday living and entertaining. Step inside through the impressive entry foyer and discover 9-foot ceilings on both the first and second floors, smooth drywall finishes, craftsman trim, and quality finishes throughout. The heart of the home is the expansive kitchen featuring granite countertops, a large center island, walk-in pantry complete with cabinetry and countertop workspace, breakfast nook, and seamless flow into the spacious family room with an inviting electric fireplace. A dining room, private office, and convenient mudroom provide additional flexibility for today's lifestyle. The luxurious first-floor primary suite offers generous walk-in closets and a spa-inspired bath with a double vanity, tile flooring, tiled shower, and linen closet. Upstairs, you'll find three oversized bedrooms with walk-in closets. The front bedroom includes a private bath, while the two rear bedrooms share a convenient Jack-and-Jill bath. A spacious loft/game room with durable LVP flooring creates a space for recreation, media, or a second living area. Built for comfort & efficiency, this home includes an elevated slab foundation, premium vinyl lap siding, architectural shingle roof, attached 2-car garage, upgraded carpet, dual-zone HVAC systems,4" submersible well, a high-efficiency 50-gallon heat pump water heater, conventional septic system, & pre-wiring for Ethernet and Wi-Fi. Relax on the front or rear concrete porches while enjoying peaceful country views, just minutes from shopping, dining, and everyday conveniences. This exceptional property offers the best of both worlds—modern amenities, quality craftsmanship, and the freedom of country living on your own 3-acre retreat.

1630 Taft Road, South Chesapeake
2020 Sanderson Road, South Chesapeake
$798,900
4 Beds ⋅ 3 Baths ⋅ 10657878 MLS
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
941 Long Ridge Road, South Chesapeake
$439,000
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
2448 Johnstown Road, South Chesapeake
$624,900
4 Beds ⋅ 2 Baths ⋅ 10657067 MLS
Enjoy the tranquility of this charming ranch nestled on a private lot spanning nearly 3 acres. The inviting floor plan welcomes you with a cozy living room featuring a fireplace and wet bar, creating a great space to relax or entertain. At the heart of the home, the kitchen is filled with natural light from two large windows and offers ample cabinet and counter space, along with stainless steel appliances. Just off the kitchen, the dining area allows for effortless gatherings and everyday living. The spacious primary suite provides a peaceful retreat with a large walk-in closet and private ensuite bathroom. The additional bedrooms are generously sized, offering flexibility for guests, or a home office. Outside, the expansive backyard and screened porch provide endless opportunities to enjoy the surrounding natural beauty and peaceful setting. Experience the best of country living with the convenience of a short commute to shopping, dining, and everyday amenities.

2448 Johnstown Road, South Chesapeake
1149 Beaver Dam Road, South Chesapeake
$925,000
4 Beds ⋅ 3.1 Baths ⋅ 10655807 MLS
Tucked away on more than three private acres is the kind of place you imagine when you picture escaping from it all. A long paved driveway welcomes you in, opening to an expansive stamped-concrete parking area and a charming custom-built home surrounded by woods, open fields, and room to simply breathe. Step inside and soaring 10-foot ceilings and an open, airy floor plan immediately make the home feel special. At the heart of it all is a large eat-in kitchen with a center island and breakfast bar—the kind of kitchen made for slow mornings, late-night conversations, and everything in between. A separate additional formal dining room offers the freedom to curate whatever space fits your life, whether that's a beautiful dining area, home office, private library overflowing with your favorite novels, or something entirely your own. There are two en-suite bedrooms, generously sized upstairs bedrooms filled with natural light, abundant storage, and a spacious primary suite with an oversized bathroom and walk-in closet. But outside is where this property truly begins to feel like its own little world. Wander onto the sprawling deck and look out over peaceful woods and open fields. Follow the property beyond the house and you'll find that this over three acre property line is FULLY FENCED behind the house. Fenced areas in both the front and back, ready for horses, stocked with coops, and multiple outbuildings waiting to become whatever you dream up. Bring the horses. Raise goats. Keep chickens and rabbits. Turn an outbuilding into a workshop, art studio, hobby space, or your own quiet hideaway. There are acres to explore, spaces to create, animals to care for, sunsets to watch, and enough privacy to make the rest of the world feel wonderfully far away. It feels like the countryside. It feels like an escape. It feels like your own little storybook world. And somehow, dining, shopping, and everyday conveniences are still just a short drive away. More than three acres. Endless possibilities. One truly magical place to call home.

1149 Beaver Dam Road, South Chesapeake
241 Sign Pine Road, South Chesapeake
$950,000
4 Beds ⋅ 3.1 Baths ⋅ 10655919 MLS
Your dream home awaits!! Craftsman bones, a custom remodel, and a horse barn out back: acreage living with refined character. Every inch of this home was designed by the sellers who were contractors with love over the years. Inside, coffered ceilings meet warm cedar and wood-plank ceilings, giving every room a crafted, finished feel, and Brazilian cherry hardwoods run underfoot toward a stone gas-log fireplace that anchors the living space. Floor-to-ceiling windows and skylights flood the home with light, while custom barn doors and Restoration Hardware fixtures make even the transitions between rooms feel intentional. The kitchen is built to gather around. An oversized honed granite island with a built-in microwave takes center stage, backed by custom cabinetry, an etched tile backsplash, a built-in pantry, newer appliances, and purified water at the sink. Next door, color-changing upper lighting lets the dining room shift from weeknight dinner to late-night celebration at the flip of a switch. The first-floor and second story primary suite comes with its own bath, the bathrooms have been updated throughout, and a sun room, bar and mudroom with drop zone give the layout room to breathe. Then step outside, where the property really shows off. A 40,000-gallon saltwater pool, 8 feet deep with a diving board and fountain, sits beside a koi pond and gazebo linked by brick walkways. Made for a party or a wedding. Beyond it, a fenced acre of pasture leads to a barn with two stalls, a wash stall, a brick-paved breezeway, tack room, and horses are allowed. Wrapped in Hardie plank and stone, heated and cooled by geothermal, and tucked into a wooded setting of nearly five acres neighboring Greenbrier Farms in the Hickory school zone. Morning coffee in the sun room, afternoons at the barn, evenings by the pool: this home makes every part of the day worth staying for. And let's talk privacy.

241 Sign Pine Road, South Chesapeake
2410 Centerville Turnpike, South Chesapeake
$875,000
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
2536 Seven Eleven Road, South Chesapeake
$899,000
6 Beds ⋅ 3.1 Baths ⋅ 10655175 MLS
Room to spread out, space for horses, and a country setting without giving up Chesapeake conveniences. Set on approx. 5 treelined acres in Grassfield, this all brick estate offers 2 primary suites w/ one on first floor providing flexibility for guests. Watch wildlife from your back deck, cool off in the pool, & unwind in the hot tub! Two horse barns, lamb barn, feeding shelter and add. storage support equestrian interests. No HOA. Roof & windows replaced 2017. Upstairs HVAC 2024. Shopping/dining Grassfield Pkwy/Cedar Rd. Grassfield Highschool. Bring your vision & make it yours!!

2536 Seven Eleven Road, South Chesapeake
1733 Head Of River Road, South Chesapeake
$829,900
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
1741 Taft Road, South Chesapeake
$999,999
4 Beds ⋅ 2.1 Baths ⋅ 10653479 MLS
Three wooded acres. A saltwater pool. Five garage bays. Room for the boat, RV and workshop. And no HOA. 1741 Taft Road offers a combination that’s increasingly hard to find in Southern Chesapeake. The approx. 3,700-sq.-ft. home features 4 bedrooms, 2.5 baths and a welcoming wraparound porch. Inside, the kitchen is equipped with matte white Café appliances including a gas range, while the spacious living room centers around a wood-burning fireplace. Upstairs are 4 generously sized bedrooms, including a primary suite with 2 walk-in closets. A finished third floor adds 2 large bonus rooms, creating flexible space for a nursery, home office, gym, studio or private retreat. Outside, an approx. 32,000-gallon saltwater pool and composite deck anchor the backyard, with major pool components updated in 2025–26. A heated 2-car attached garage is joined by a 3-bay detached garage/workshop with propane heat plus mini-split heating and cooling. Covered paved storage accommodates a boat, camper or RV, with a pole barn and additional storage shed adding even more versatility. The acreage continues beyond the rear gate into the woods, where walking trails extend the ways to enjoy the property. Extensive paved parking and a private setting complete a property that offers breathing room without giving up convenient access to Chesapeake.

1741 Taft Road, South Chesapeake
4020 Tucker Lane, South Chesapeake
$989,900
4 Beds ⋅ 3.1 Baths ⋅ 10652733 MLS
Grace, Beauty, Functionality, Beautiful private location (acreage on a cul de sac) , only 10 lots on clear land bordered by mature trees as a backdrop. The primary opulent primary bath including an extra large closet and another large en suite are on the first floor along with a flex room. Our newest option is a "butlers kitchen" complete with full sink tucked just behind the well equipped main kitchen. Two additional large bedrooms upstairs. Covered rear porch with an amazing view! You couldn't ask for more. This semicustom building package is hard to beat! We have additional lots and plans available. This will be the last acreage neighborhood to be approved within the city. No main road lots here! If you are looking for new construction it a definite 'MUST SEE"! Ponds, wildflower field, private walking trail and more add up to an exceptional "positive vibe" . No upgrades needed, come see! Preferred lender incentives be sure to ask for details. We have 1 acre 3 acre and a 20 acre lot

4020 Tucker Lane, South Chesapeake
1837 Benefit Road, South Chesapeake
$825,000
4 Beds ⋅ 4 Baths ⋅ 10647485 MLS
Welcome to this custom-built retreat situated on 5 acres in a highly desirable Grassfield school district. Thoughtfully designed this exceptional property offers generous indoor and outdoor space with features ideal for multigenerational living, entertaining, hobbies, and storage. The private in-law suite includes a kitchenette and its own screened porch, creating a welcoming space for guests or extended family. Upstairs, you’ll find two ensuite bedrooms, along with an additional bedroom that offers excellent potential as a theater room, home office, or flexible living space. Car enthusiasts, hobbyists, and those seeking extra workspace will appreciate the two-car attached garage, one-car detached garage with work area, and two storage sheds. From the inviting front porch—perfect for quiet mornings and scenic views—to the rear deck designed for gathering with family and friends, this one-of-a-kind property offers the space, privacy, and versatility today’s buyers are looking for.

1837 Benefit Road, South Chesapeake
112 Station Road, South Chesapeake
$725,000
5 Beds ⋅ 2.1 Baths ⋅ 10642786 MLS
One of a kind property in Hickory area of Chesapeake with 2 (YES TWO) SFH that are legally deeded, WATERFRONT (ocean access) ~3.5 ac lot, with no neighbors in sight! Main house is over 3,000 sqft 5/2.5. Smaller house about 1200 sqft, 2/. Both have newer systems and New Roofs. Each home has its own Septic/Well system & pumped in 2024-large house/2025-small house. Property backs to 60 ft of riverfront that leads through the sounds and into the ocean. The main farmhouse has modern amenities but the old charm and character with original hardwoods, curved arches and entry ways, Juliet Balcony overlooking estate, 3rd floor finished attic bonus room and solid walk down basement foundation that can be turned into a finished room or used for storage. This home is solid and well maintained, being sold as is, seller to make no repairs. Call today for your private showing!

112 Station Road, South Chesapeake
2430 Ballahack Road, South Chesapeake
$693,000
4 Beds ⋅ 3.1 Baths ⋅ 10627065 MLS
NEW CONSTRUCTION WITH APPROX 3 TO 4 MONTHS TO COMPLETION. 2 story transitional home boasting an open floorplan and situated on a 1 acre parcel in Southern Chesapeake. 4 bedrooms and 3.5 baths. TWO PRIMARY SUITES, one UP and one DOWN! Both suites include a walk in closet and full bath with tile flooring, granite top vanity and double bowls. Large Eat in Kitchen opens to Great Room and features quartz counters, soft close custom cabinets, island, walk in pantry, and stainless appliances. ADD'L DETAILS: architectural shingle roof and gutter system, 2 car garage with opener, brick skirt and crawlspace, Deck, Laundry/Mud Room with upper cabinets, Formal Dining Room, granite counters and tile flooring in all baths, carpeting in bedrooms, and LVP flooring in Entry, Kitchen, Great Room, and Formal Dining Room. Local Builder is known for his exceptional quality and custom details. Attends Grassfield HS, Hickory MS, and Hickory Elementary. Buyer can make selections.

2430 Ballahack Road, South Chesapeake
3016 Cedarville Road, South Chesapeake
$949,000
3 Beds ⋅ 1 Baths ⋅ 10571232 MLS
Two parcels of cleared land Zoned A-1 totaling over 37 acres with 604.83 feet on Cedarville Road in the Hickory area of Chesapeake. The front lot with 21.67 acres. The back lot with 15.87 acres. Listing Agent is the managing partner of the ownership LLC. Must request appointment to see the property and provide a 24-hour notice. Contact the Listing Agent to schedule your appointment.

3016 Cedarville Road, 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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