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1901 Prince Edward Drive, South Chesapeake
$925,000
4 Beds ⋅ 3 Baths ⋅ 10606398 MLS
Welcome to 1901 Prince Edward Drive in Chesapeake, VA! This property offers incredible space, privacy, and versatility, situated on a large 2 acre wooded lot with an updated septic system and a beautiful saltwater pool. The main home features 4 bedrooms, 3 baths, and 2,667 sq ft with a 2-car garage and abundant storage. The kitchen is a true showpiece, showcasing white cabinetry with glass accents, expansive countertops, designer pendant lighting, and a large bay window overlooking the pool and serene backyard. The living area flows seamlessly with custom built-ins and abundant natural light. Upstairs you’ll find spacious bedrooms, a versatile FROG, and a generous primary suite with a beautifully appointed bath. Outside, enjoy the expansive deck, lush yard, and detached guest house above the 3 car garage with 2 bedrooms, 1 bathroom and full kitchen—great for in-laws, guests, or rental potential. A rare combination of comfort, style, and space in the heart of Chesapeake!

1901 Prince Edward Drive, South Chesapeake

1928 Long Ridge Road, South Chesapeake
$970,000
5 Beds ⋅ 3 Baths ⋅ 10615178 MLS
All-brick custom beauty on 4.7 acres! Step inside to a grand marble foyer and stunning two-story family room showcasing detailed trim work and abundant natural light. The open kitchen offers a sunny breakfast nook and flows seamlessly into a spacious four-seasons room, perfect for year-round enjoyment. The first-floor primary suite features frayed ceilings, an expansive bath with large walk in shower and separate soaking tub, while an additional bedroom on the main level offers convenient full bath access great for an office or guest suite. Upstairs, you'll find large, private secondary bedrooms and a walk-in attic for excellent storage. Horses welcome! This meticulously maintained home radiates quality and pride of ownership throughout.

1928 Long Ridge Road, South Chesapeake

1441 Whittamore Road, South Chesapeake
$200,000
4 Beds ⋅ 1 Baths ⋅ 10615955 MLS
Wonderful opportunity to secure property in Hickory section of Chesapeake. Home needs work. City website property lines not accurate, city working to update. More than likely cash or rehab financing only. Floor dips downstairs, ceiling missing drywall, possible microbial growth at upstairs ceiling and on some walls, doors, wood rot at some of the windows. Setup showing via Showing time. Subject to court approval (usually adds 2 weeks to typical process) and special warranty deed. Park in the gravel driveway as long as it does not block access to the house behind the subject property or they can park in the grass behind the house. Owners will mark septic lines over next couple days. Please exercise caution entering home, the living room floor sags.

1441 Whittamore Road, South Chesapeake

2200 Carolina Road, South Chesapeake
$600,000
4 Beds ⋅ 2 Baths ⋅ 10599748 MLS
Charming 1982 ranch home with equestrian facilities on 6.526 acres in Chesapeake. The 1,575 sq ft home offers 4 bedrooms, 2 full baths, a primary suite w/ walk-in closet, eat-in kitchen w/ bay window & pantry, cathedral ceiling in living room, full laundry, mudroom & covered porch. Recent updates include windows (2022) & roof (2017). The property includes a 54'x48' barn w/ 7 stalls, air-conditioned tack room, wash/laundry, hot/cold water, storage loft w/ bath, plus a 70'x18' equipment shed. Riding amenities feature a 127'x70' lighted arena, 60' round pen, 3 run-in shelters w/ water & power, fenced pastures & paddocks. Roof on barn replaced 2019. Designed for training, boarding or private enjoyment--this property blends function & charm for horse enthusiasts seeking country living minutes from city convenience.

2200 Carolina Road, South Chesapeake

2816 Benefit Road, South Chesapeake
$400,000
3 Beds ⋅ 2.1 Baths ⋅ 10611323 MLS
Experience peaceful country living with thoughtful upgrades throughout this beautifully maintained home. The main level features 9' ceilings, an updated kitchen with newer appliances, quartz countertops, and a reverse osmosis water filtration system. Additional improvements include an upgraded well pump, septic pumped in 2023, new flooring, a newly installed shower door in the larger shower, and a new garbage disposal. Both heat pumps were replaced in 2019, and the attic access has been relocated for improved convenience. This property offers the best of both worlds—quiet country living with the convenience of popular stores and restaurants just 15 minutes away. The outdoor spaces provide a serene setting, for relaxing on the back porch or enjoying evenings by the fire pit. Zoned for horses, this home blends modern comfort with tranquil country surroundings.

2816 Benefit Road, South Chesapeake

980 Beaver Dam Road, South Chesapeake
$910,000
4 Beds ⋅ 3.1 Baths ⋅ 10612453 MLS
980 Beaver Dam Rd, the Ashbee Model in Hickory Bend by Wetherington Homes. READY NOW! Situated on 11.47 serene acres in Southern Chesapeake, this 2 story craftsman style Home offers an open floor plan with 4 Bedrooms PLUS A LOFT AND AN OFFICE! Great Room opens to Kitchen with center island with overhang for extra seating, dining area, quartz counters, tile backsplash, pantry, and stainless appliances. First floor Owner's Suite features extra large walk in closet with wood shelving and full bath with tile surround step in shower, soaking tub, tile flooring, vanity with double bowls and granite counters, linen and water closets. You will love the Covered Porch to enjoy the peaceful wooded setting! ADD'L DETAILS: Mud Room with drop zone; 1st flr Laundry Room; LVP flooring on 1st flr; wood stair treads; carpeting in bedrooms; granite in full baths; Front Porch; 2 car garage; architectural shingle roof; partially fenced back yard, and more! Attends Hickory Schools.

980 Beaver Dam Road, South Chesapeake

1900 Pocaty Road, South Chesapeake
$900,000
4 Beds ⋅ 2.1 Baths ⋅ 10607844 MLS
Welcome to Gum Tree Farm – a rare 45-acre countryside farm offering peaceful living just minutes from Chesapeake’s city conveniences. This charming country home features a wraparound porch, wood floors, woodstove, and a classic claw-foot tub. Home features primary on first floor and 2nd bedroom first floor, and 2 additional BR 2nd floor with small bath. The land offers 4 fenced pastures, with additional paddocks, a 12-acre hay field, bridle path, hay barn, HUGE pole barn, LG chicken coop, LG dog kennel — great for those who love farm life. Timber was replanted with Loblolly pines in 1999, and the property participates in the Land Program with income from hay production & livestock. Recent updates include HVAC (2023), well pump (2024), water softener (2025), and a refreshing new above pool (2025). Relax in Hot tub surrounded by Mother Nature. A haven for Horses, Sheep, Cattle, Goats, and chickens — where serenity, self-sufficiency, and Southern charm meet.

1900 Pocaty Road, South Chesapeake

801 Benefit Road, South Chesapeake
$617,500
3 Beds ⋅ 2 Baths ⋅ 10608955 MLS
Totally renovated and move-in ready, this southern Chesapeake gem blends country charm with modern comfort. The stunning kitchen features a beautiful island, quartz counters, new cabinetry, and a tasteful backsplash. The open-concept layout offers effortless flow for entertaining, while a wood-burning stove with new flue adds cozy character. Enjoy a 1st-floor bedroom, full bath, and laundry for easy living. Protected wetlands behind ensure lasting privacy, yet you’re just 5 minutes from shopping, dining, and entertainment. Energy-efficient window tint on all windows saves energy and protects from UV damage. Approx 1 acre around the home is enclosed by an invisible fence—perfect for keeping your furry friends safe. The sunroom (not in sqft) overlooks an in-ground pool, large deck, and spacious pool house. Huge barn, raised garden beds, and agricultural zoning allow animals or hobby farming. Roof ~10–15 yrs, HVAC 2017, WH 2018, encapsulated crawl.

801 Benefit Road, South Chesapeake

1469 Whittamore Road, South Chesapeake
$595,000
3 Beds ⋅ 2 Baths ⋅ 10603401 MLS
This exquisite, "2 year young" home features an open, light-filled floor plan w/ high end finishes. The gourmet kitchen has a double oven, w/ quartz countertops that opens to a spacious family room w/ high ceilings & a built in electric fireplace . There is a 8 'X 17' sunroom off the back & a small office off the living room. The luxurious primary suite has the "Wow Factor" The master closet has custom built-ins & the master bath is like one out of a magazine, w/ a tiled shower, whirlpool bath & double vanities . Two additional bedrooms are spaced towards the front that share a bathroom. A walk in laundry room leads to the 22'X 21' bonus room. Use your imagine w/the huge space that was planned as the 2 car garage, but instead was finished as heated floor space! Outside, find a 25’ x 26’ metal building ideal for a garage or workshop, plus ample parking w/ a crush-and-run driveway. The backyard is completely fenced & the house sits nicely back off the road. This home is a "must see!"

1469 Whittamore Road, South Chesapeake

1149 Beaver Dam Road, South Chesapeake
$890,000
4 Beds ⋅ 3.1 Baths ⋅ 10600154 MLS
Welcome to your private 3-acre sanctuary, complete with outbuildings and fenced areas great for horses, pets, or hobbies. Property offers both seclusion & space, featuring a paved driveway & expansive stamped-concrete parking area. This custom-built home boasts 10-foot ceilings & an open concept floor plan designed for comfort & entertaining. Spacious family room with tray ceiling flows seamlessly into the eat-in kitchen, where you’ll enjoy wooded backyard views, center island & breakfast bar. For more formal occasions, or a home office, the dining room offers flexibility to fit your needs. Home includes two en-suite bedrooms, providing convenience & privacy, along with generously sized upstairs bedrooms filled with natural light. Outdoors, a sprawling deck invites you to relax or host gatherings in complete privacy. The fenced areas in both the front & back are ready for animals or can be reimagined to suit your lifestyle, all while backing to open fields for a truly peaceful setting.

1149 Beaver Dam Road, South Chesapeake

1040 Sanderson Road, South Chesapeake
$847,000
4 Beds ⋅ 2.1 Baths ⋅ 10602250 MLS
Spacious and charming brick Cape Cod offering 3,260 sq ft of comfortable country living. This 4-bedroom, 2.5-bath home features large, light-filled rooms—including a formal dining room, den, cozy fireplace, and private office/study—providing plenty of room to spread out and make it your own. The layout flows beautifully, creating a welcoming feel throughout. Enjoy peaceful mornings or gatherings on the wood deck overlooking wide open skies and green pastures. Vinyl rail fencing surrounds two animal-ready fields, excellent for horses or hobby farming. The home includes an attached 2-car garage and a detached 2-car garage with a spacious garage apartment above. This home is a wonderful mix of space, charm, and quiet country life! Beautiful home ready for the next generation.

1040 Sanderson Road, South Chesapeake

2344 Silvertown Avenue, South Chesapeake
$1,300,000
4 Beds ⋅ 3 Baths ⋅ 10598728 MLS
Dream sanctuary in the heart of Hickory.This property boasts a sprawling 160 acre homestead,surrounded by picturesque agricultural fields & lush timberlands,making it a haven for Deer & Turkey enthusiasts.The farmhouse features a stunning wraparound porch, ideal for panoramic views of your private estate to include a private pond.The spacious primary suite has his & hers closets & an adjoining nursery that can easily transform into a cozy bedroom or an inspiring home office.Equestrian lovers will appreciate the 3600 sqft barn,designed with 6 stalls,a full loft for extra storage & essential amenities including an electrical panel,running water & rubber matting for equine comfort.Additionally, a sizable 60'x100' pole barn with separate meter offers more space for Ag equipment or livestock.With miles of Equestrian & ATV trails, this unique property is ideal for those seeking country life while still being conveniently located just minutes from the Chesapeake bypass,restaurants & shopping.

2344 Silvertown Avenue, 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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