South Chesapeake Homes with Well Exterior features

Welcome to South Chesapeake, a charming city nestled in the heart of Chesapeake, Virginia. Known for its serene surroundings and friendly community, South Chesapeake offers a peaceful retreat from the hustle and bustle of city life. With easy access to major highways and a short drive to the Virginia Beach oceanfront, residents enjoy the best of both worlds - a tranquil suburban lifestyle and close proximity to urban amenities.

If you're looking for homes with well exterior features in South Chesapeake, you're in luck. True to its reputation for beautiful properties, South Chesapeake boasts a variety of homes with well-maintained exteriors that exude curb appeal. From meticulously landscaped gardens to inviting front porches, these homes are a testament to pride of ownership and attention to detail.

Whether you're in the market for a cozy bungalow or a spacious family home, South Chesapeake has something for everyone. Imagine coming home to a picturesque setting where every detail is thoughtfully designed to create a welcoming atmosphere. With a strong sense of community and a focus on quality living, South Chesapeake is the perfect place to plant your roots and make lasting memories.

Come and explore the beauty of South Chesapeake - where small-town charm meets modern convenience, and where you'll find the home of your dreams with well exterior features that truly stand out.

Newest South Chesapeake Homes with Well Exterior features

$825,000

6 Beds ⋅ 3 Baths ⋅ 10656228 MLS

Welcome to the desirable neighborhood of Ravenna, located in the sought-after Hickory high district. This 6 bdrm, 3 bath home is located on a .46 acre cul-de-sac lot. The backyard is truly huge w/ample room for a pool. It is overlooked by a 450 sf 2 level deck & backs to a natural wooded area for great privacy & includes several fruit trees. The kitchen has been updated w/granite countertopss, upgraded Samsung appliances, ceramic tile flooring. It also includes an abundance of custom maple cabinets, a large center island, pantry & tiled backsplash. It overlooks a huge FR with matching built-bookcases & gas FP. There are beautiful, true hardwood floors in the LR, DR, FR, foyer & back hallway. The large primary suite upstairs is served by 2 walk-in closets & an impressive primary bath including double sink vanity, jetted tub & separate shower. 1 bedroom (16 x 14) is downstairs & next to the full downstairs bath in the back hall. A fully finished sunroom, is adjacent to the breakfast area.

1503 Theodora Court, Chesapeake

$1,650,000

5 Beds ⋅ 3.2 Baths ⋅ 10656180 MLS

Quiet Luxury. Architectural Artistry. This Custom Built Estate was designed not simply to be lived in, but to be experienced on 4 acres, 5,900 sqft (plus add'l 980 ROG). The dramatic, soaring ceilings & windows throughout a 2-story family rm w/stone fireplace, along w/every custom architectural detail make a statement of true Luxury. From the picturesque curb appeal to first floor Primary Suite & your own private spa, a cedar-lined wellness retreat w/hot tub. The expansive fl plan provides flexibility for formal gathering & relaxed everyday living. This home was thoughtfully designed, w/ 4 add'l spacious bedrms, generous living & entertainment areas, abundant nat'l light & craftsmanship throughout. New 6 burner-gas Wolf range in large kitchen, Trex board decking outside, endless possibilities to entertain & peace/privacy. An inground pool, pool house, pergola & plenty of open space. Large ROG is ready for you to make it your own movie/game room! Ask your agent for feature sheet!

3342 Martin Johnson Road, Chesapeake

$475,000

4 Beds ⋅ 2 Baths ⋅ 10655999 MLS

Escape to your own private waterfront retreat on nearly 1/2 acre in the sought-after Inland Colony community, where peaceful wooded surroundings and serene water views create the perfect connection to nature. This 2,494 sq. ft. home offers 4 bedrooms, 2 baths, a first-floor primary suite, detached ADU, 1-car garage, and private dock with access to the Intracoastal Waterway on the Elizabeth River. Enjoy the expansive deck overlooking the backyard and water or unwind on the screened porch off the primary suite. Fresh paint and new carpet enhance the bedrooms, while the spacious kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and generous prep space. French doors open from the dining room to the living area, creating an ideal layout for entertaining. The FROG with new carpet and large walk-in attic provide excellent flexibility and storage. Some photos may be virtually staged. Conveniently located near shopping, dining, top-rated schools, and interstate access while offering a true waterfront escape.

1145 Sunlight Drive, 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, Chesapeake

$1,195,000

5 Beds ⋅ 4.1 Baths ⋅ 10655222 MLS

This home truly has it all! Meticulously maintained & beautifully updated, this custom home sits on 3 acres offering space, privacy & versatility. Hardwood floors span the 1st & 2nd floors, complemented by plantation shutters. With 5 bedrooms, PLUS a finished room over the garage, there is room for everyone, including 3 bedrooms with ensuites .The 1st floor primary features a clawfoot tub & separate shower. A gorgeous kitchen with updated appliances & pot filler opens to the family room & bright sunroom with wood stove overlooking the saltwater pool. Outside, enjoy a low maintenance deck, attached 2-car garage, detached 2-car garage with unfinished 2nd floor & extra parking for a boat or RV. Brand new roof, updated HVAC ,remodeled bath & numerous additional improvements make this home truly move-in ready. Assumable 2.25% VA loan. This one is a must see!

1108 Kathleen Lane, 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, Chesapeake

$559,900

3 Beds ⋅ 2 Baths ⋅ 10655745 MLS

Welcome to 811 Bellingham Drive! This detached 3 bedroom, 2bath home offers approximately 1,612 square feet of living space with plenty of additional storage and outdoor features. The property includes a 24x26 detached garage with an unfinished room upstairs, providing additional space for storage or future customization. Two additional sheds offer even more storage. Enjoy the outdoors from the approximately 20x18 wood deck overlooking the spacious yard. The front yard features a sprinkler system with a deep well for watering. Conveniently located in Chesapeake with plenty of possibilities inside and out!

811 Bellingham Drive, Chesapeake

$737,000

4 Beds ⋅ 3 Baths ⋅ 10655495 MLS

Welcome to this beautifully updated all-brick ranch home in sought-after Emerald Lakes in southern Chesapeake, Virginia. This 2,777-square-foot home offers 4 bedrooms, 3 full baths, one-level living & a 2-car side-load garage on a 1/2-acre cul-de-sac lot. The gourmet kitchen features quartz countertops, a 5-burner gas cooktop, GE Profile stainless appliances, double oven & butler’s pantry, with both an eat-in kitchen & formal dining room. Primary suite w/private bath plus separate en-suite bedroom—ideal for multigenerational living—and two additional bedrooms. Cathedral ceilings, hardwood floors, a gas fireplace & flexible office/library space. The saltwater inground pool, stone patio, gazebo & large outdoor fireplace create an exceptional private entertaining space. New pool salt cell with Wi-Fi controls, encapsulated crawl space with dehumidifier, approximately 3-year-old roof and 2-year-old water heater. Convenient to the NC line, Moyock & the NC Outer Banks.

804 Brookside Arch, 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, 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.

101 Stadium Drive, Chesapeake

$722,000

5 Beds ⋅ 3 Baths ⋅ 10655212 MLS

Homes like this rarely come to market in sought-after Great Bridge. Set on a cul-de-sac, 809 Chris Court showcases vaulted ceilings, graceful archways, rich trim work, and a remarkable floor plan for entertaining and first-level living. At the heart of the home, the updated kitchen welcomes quiet mornings and memorable celebrations, flowing into a grand living room with a gas fireplace and inviting hearth, plus access to the Trex deck. A formal dining area awaits your gatherings. The main-level primary suite offers a private retreat with an en-suite bath, beautifully crafted walk-in shower, and walk-in closet. Five generously sized bedrooms, a dedicated office, abundant storage, a walk-up attic, and an oversized two-car garage ensure space is never in short supply. Outside, meticulous landscaping and a vinyl-fenced backyard complete the setting. With exceptional entertaining spaces, privacy, and a Great Bridge location, this is more than a home…it is the opportunity buyers wait for.

809 Chris Court, Chesapeake

$975,000

6 Beds ⋅ 3.1 Baths ⋅ 10655175 MLS

Discover a private country retreat in the heart of Grassfield, where approximately 5 tree-lined acres create a peaceful setting rarely found with this much space and convenience. Over 4,000 sqft of living space with 6 beds, 3.5 baths, first floor primary ensuite. Spend summer days by the pool, unwind beneath the stars in the hot tub, or enjoy the freedom of acreage with a barn and zoning that permits horses. Mature trees frame the property and provide a sense of privacy while still placing you in the heart of Chesapeake, convenient to shopping, dining, schools and major routes.

2536 Seven Eleven Road, Chesapeake

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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.