South Chesapeake Homes with Gazebo Exterior features

Welcome to South Chesapeake, Virginia—a charming blend of suburban tranquility and vibrant community spirit. Nestled in the heart of Chesapeake County, this delightful area boasts a rich tapestry of history, culture, and natural beauty. With its picturesque landscapes, lush parks, and friendly neighborhoods, South Chesapeake offers a welcoming atmosphere for families, young professionals, and retirees alike.

One of the standout features of homes in South Chesapeake is the enchanting presence of gazebos. These delightful exterior structures not only enhance the aesthetic appeal of a property but also serve as a perfect retreat for relaxation and entertainment. Imagine sipping your morning coffee or hosting a summer barbecue under the gentle shade of a beautifully crafted gazebo. It’s an inviting space that encourages outdoor living and fosters connections with family and friends.

The homes in South Chesapeake with gazebo features are often characterized by their spacious yards, mature landscaping, and thoughtful designs that harmonize with the surrounding environment. Whether you’re seeking a cozy cottage or a sprawling family home, you’re likely to find a property that suits your style and needs in this charming area.

As you explore South Chesapeake, you’ll discover an array of local amenities, including shopping centers, dining options, and recreational activities. With a strong sense of community and a commitment to maintaining its natural beauty, South Chesapeake is not just a place to live; it’s a place to thrive. Come and experience the allure of this vibrant city, where your dream home with a gazebo awaits!

Newest South Chesapeake Homes with Gazebo Exterior features

$369,900

4 Beds ⋅ 2 Baths ⋅ 10659368 MLS

Welcome to 1108 Sword Dr, a beautifully updated 4-bedroom, 2-bath ranch-style home offering approximately 1,800 sqft of comfortable single-level living in Chesapeake, VA. Freshly painted throughout, this move-in-ready home features a bright, open-concept floor plan with LVP flooring throughout the main living areas, carpeted bedrooms, and updated light fixtures. The kitchen features granite countertops, stainless steel appliances, and an open layout that flows seamlessly into the living and dining areas. Both bathrooms have been updated, adding to the home’s fresh, modern feel. Additional improvements include a new roof. Step outside to a large, fully fenced backyard with plenty of space for entertaining, pets, play, gardening, or simply relaxing outdoors. If you’re searching for a move-in-ready 4-bedroom ranch home for sale in Chesapeake, Virginia with approx. 1,800 sqft an open floor plan, modern updates, and a spacious fenced backyard, 1108 Sword Dr is one you’ll want to see!

1108 Sword Drive, South Chesapeake

$629,900

5 Beds ⋅ 3.1 Baths ⋅ 10658802 MLS

If you've been searching for a spacious, move-in-ready home with a private in-law suite on a large lot in the heart of Chesapeake, your search is over! This one-of-a-kind property offers the blend of comfort, flexibility, and space. The traditional in-law suite features its own multiple entrances, full kitchen, living room with a cozy gas fireplace, recently remodeled bathroom, bedroom, and dedicated laundry area—use for multi-generational living or extended guests. Step outside to a large backyard for relaxing or entertaining, complete with a recently built gazebo with electricity and a storage shed for all your gardening and outdoor needs. Located in a neighborhood with sought-after schools, you'll enjoy convenient access to shopping, dining, parks, and more. Don't miss this rare opportunity to make this exceptional Chesapeake home yours!

1307 Channing Way, South Chesapeake

$980,000

6 Beds ⋅ 4 Baths ⋅ 10657839 MLS

An exceptional opportunity to own a Stephen Alexander custom home in Greystone, one of Chesapeake's premier luxury communities where homes are rarely available. This expansive executive residence blends timeless craftsmanship with the space, flexibility, and resort-style amenities today's luxury buyers seek. A first-floor bedroom with an adjacent full bath offers versatility for guests, a home office, or multi-generational living. The primary suite is a true retreat with a fireplace, sitting area, and four closets. Enjoy a private backyard oasis featuring an in-ground pool, hot tub, screened porch, gazebo, fire pit, privacy fence, irrigation well, and expanded parking for a boat or RV. Scenic walking paths enhance this sought-after community. Significant recent investments include a new roof (2026), three HVAC systems, an encapsulated crawl space, new hardwood flooring, updated bath vanities, freshly painted kitchen cabinetry, and a new oven. Schedule your private showing today!

821 Redleafe Circle, South Chesapeake

$500,000

4 Beds ⋅ 3 Baths ⋅ 10656410 MLS

This is one of those rare homes that truly supports multi gen or other uses. TRUE DETACHED in law suite with kitchenette full LARGE bath, living and bedroom, private access. The roof, paint, carpet dishwasher ALL NEW to get ready to SELL ! Just a little personalization and this could be your dream home. Its just waiting for you. Full brick, masonry fireplace, oversized deck, extra driveway and a covered parking area. City and Zillow records not reflective of the current dwelling. Three generous bedrooms plus room over the garage AND the suite make this home a winner for you! DONT DRIVE? NO PROBLEM! VERY NEAR ALL ANCILLARY SERVICES Extra nice YMCA with indoor and outdoor pool just a few short blocks. Physicians, groceries, dining and the highway system.

229 Fresno Drive, South Chesapeake

$459,900

4 Beds ⋅ 2 Baths ⋅ 10656377 MLS

Welcome to this spacious 4-bed, 2-bath home situated on a beautiful half-acre lot in the heart of Great Bridge! Offering a flexible floor plan, this home features 2 oversized living areas, 2 spacious primary bedrooms, & 2 additional bedrooms—ideal for multigenerational living, a home office, playroom, or the potential for a 5th bedroom. Updates include fresh interior paint, new flooring, restored hardwood floors, & renovated bathrooms. The updated kitchen offers new countertops, ample cabinet space, & a cozy breakfast nook. Step outside to the covered deck overlooking the expansive backyard, providing plenty of room for entertainment, gardening, pets, or future outdoor additions. With no HOA, you’ll also enjoy plenty of space to park your RV or boat on the property. Located in the highly desirable Great Bridge school district, you’ll enjoy the convenience of being just minutes from shopping, restaurants, & everyday amenities. Don’t miss this rare opportunity to own a move-in-ready home with space, flexibility, & an unbeatable location. Schedule your showing today!

145 Hurdle Drive, South Chesapeake

$450,000

3 Beds ⋅ 2.1 Baths ⋅ 10655125 MLS

Imagine coming home to a peaceful cul-de-sac tucked away just minutes from everything Greenbrier has to offer. The nearby city park is wonderful for a quick bike ride or leisurely stroll, while restaurants, shopping, and entertainment at Summit Pointe are just minutes away.This home offers the best of both worlds... the privacy and peacefulness of your own backyard while keeping you close to the places you want to go and the things you love to do. Enjoy the feeling of a quiet retreat without giving up convenience or connection.Don't miss your opportunity to make this move in ready Greenbrier gem your next home. Schedule your showing today!

621 Windward Drive, South Chesapeake

$419,900

3 Beds ⋅ 2 Baths ⋅ 10655782 MLS

Welcome to 109 Causeway Dr, a charming home nestled on a quiet street in the highly desirable Great Bridge area of Chesapeake! Enjoy major peace of mind with recent big-ticket upgrades, including a newly updated HVAC system, new water heaters, flooring throughout, and the electrical panel in the garage updated within the last 2 years. One of the standout features of this property is the HUGE backyard—providing an abundance of open space for entertaining, gardening, or play. Plus, there is ample parking and side access with more than enough space to park your large RV, boat, trailer, or multiple vehicles. Location is everything! Situated just off Battlefield Blvd, you are minutes away from top-rated Chesapeake public schools, local parks, waterways, and the Intracoastal Waterway. You'll love the convenience of quick access to everyday shopping, dining, medical facilities, and major highways for an easy commute throughout Hampton Roads.

109 Causeway Drive, 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

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

$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

$635,000

4 Beds ⋅ 2.2 Baths ⋅ 10653782 MLS

Former Home-A-Rama award-winning home with character you simply don't find every day. Tucked away on a .43-acre cul-de-sac lot, this 3-story Victorian-style home offers approximately 3,100 sq. ft. of living space and a wrap-around porch. Inside you'll find hardwood floors, generous living and dining spaces, custom details, two fireplaces and two staircases. The gourmet kitchen features quartz countertops, black stainless appliances, custom cabinetry, island and pantry. Spacious bedrooms lead to an impressive primary suite with walk-in closet, ensuite bath and fireplace. A third-level bonus space offers flexibility for an office, study or workout room. Outside, an in-ground saltwater pool, multi-level deck, gazebo, fire pit and expansive backyard create a setting for entertaining or relaxing. A truly unique home ready for its next chapter!

302 Honey Locust Way, South Chesapeake

$485,000

3 Beds ⋅ 2.1 Baths ⋅ 10653649 MLS

Renovated brick ranch in the Great Bridge school district, in established Chesapeake Colony. Less than half a mile to Great Bridge Middle, about a mile to Great Bridge Primary and under 2 miles to Great Bridge High. This single-level 3-bedroom, 2.5-bath home offers 1,854 sq ft with hardwood floors, two wood-burning fireplaces and a renovated kitchen with Corian countertops, stainless steel appliances and LVP flooring. Both full bathrooms have been fully renovated with natural stone flooring, custom tile and updated vanities. System updates include roof (2010) HVAC (2010) and tankless water heater (2025). Natural gas, a generator hookup and an oversized attached garage add everyday convenience. The 0.34-acre lot is set among mature trees, Japanese maples and azaleas. Out back: a privacy-fenced yard with a two-level composite deck and low-voltage lighting, a Wellis hot tub, a gazebo with swing, a pea gravel patio, a separate gated dog run and a powered 10x14 shed with loft and workbench. Irrigation and a double-wide driveway with parking for five complete the package. Minutes to Great Bridge shopping, dining and Chesapeake Regional Medical Center.

224 Northview Drive, South Chesapeake

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South Chesapeake Homes with Gazebo Exterior features

Newest South Chesapeake Homes with Gazebo Exterior features

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How much is your home worth?