Chesapeake Homes with Gazebo Exterior features

Welcome to the charming city of Chesapeake, Virginia, a hidden gem nestled in the heart of the Old Dominion. Known for its picturesque landscapes and rich history, Chesapeake offers a unique blend of urban conveniences and serene suburban living. With its lush parks, scenic waterways, and vibrant community spirit, it’s no wonder that families and professionals alike are drawn to this beautiful city.

One of the standout features of homes in Chesapeake is their stunning outdoor spaces, particularly those with gazebo exteriors. Imagine stepping into your backyard oasis, where a beautifully crafted gazebo serves as the perfect backdrop for summer barbecues, intimate gatherings, or simply a peaceful retreat after a long day. These charming structures not only enhance the aesthetic appeal of your property but also provide a versatile space for relaxation and entertainment.

Chesapeake’s real estate market boasts a variety of homes, from cozy bungalows to spacious family residences, many of which feature these delightful gazebos. Surrounded by lush landscaping and mature trees, these homes create an inviting atmosphere that encourages outdoor living and enjoyment of the mild Virginia climate.

In addition to the enchanting homes, Chesapeake is rich in amenities. Residents enjoy easy access to shopping, dining, and recreational activities, with numerous parks and waterfront areas to explore. Whether you’re kayaking on the Elizabeth River or strolling through the historic Great Bridge area, there’s always something to do in this vibrant city.

Discover the charm of Chesapeake, VA, where your dream home with a gazebo awaits—perfect for creating lasting memories in a community that feels like family.

Newest 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

$275,000

2 Beds ⋅ 2 Baths ⋅ 10657817 MLS

Welcome to highly sought-after, single-story living in the wonderful 55+ community of One Ford Place! This beautifully maintained Western Branch condo offers the ultimate "no-maintenance" lifestyle. The inviting layout features a spacious great room with sliding doors opening to a private patio. The well-appointed kitchen includes a pantry and conveys with all appliances. Enjoy a luxurious primary suite adorned with picture frame molding and a beautiful en-suite bath featuring a granite double vanity, tub, and separate shower. A second bedroom and full bath on the opposite side of the home create the perfect private guest suite! Enjoy the rare convenience of a one-car garage, a two-car driveway, and ample guest parking. Move in with total peace of mind thanks to major recent updates to the HVAC, water heater, and appliances. With TVs conveying and additional furniture negotiable, your transition will be a breeze. Located minutes from the YMCA, I-664, and I-164!

3301 Settlement Court, West Chesapeake

$409,900

4 Beds ⋅ 3 Baths ⋅ 10656307 MLS

SELLER WILL PAY 2% TOWARD BUYER'S CLOSING COSTS OR RATE BUY DOWN WITH ACCEPTABLE OFFER! Enjoy easy one-level living in this beautifully updated 4BR/3BA ranch on a spacious 1/3-acre corner lot. The remodeled kitchen is the heart of the home, featuring leathered granite countertops, stainless steel appliances, new cabinetry, tile backsplash, breakfast bar, and dining area. Refinished hardwoods, fresh paint, updated fixtures, a new roof, and a new full bath add to the move-in-ready appeal. Need room to work, relax, or accommodate guests? A dedicated office with built-ins and a 4th bedroom with ensuite bath and separate entrance offer flexibility for multigenerational living, a home office, gym, or private guest suite. Utility sunroom with backyard access. Entertain on the deck beneath the gazebo, complete with electricity. Two sheds provide plenty of room for storage, tools, and hobbies. Western Branch High School district. Convenient to bases, shopping, I-664 and all that Hampton Roads has to offer!

2024 Lisbon Road, West 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

$429,900

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

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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.

Chesapeake Homes with Gazebo Exterior features

Newest Chesapeake Homes with Gazebo Exterior features

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How much is your home worth?