South Chesapeake Homes with Wooded Exterior features

Welcome to South Chesapeake, Virginia, a hidden gem nestled in the heart of Chesapeake County. This vibrant community offers the perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, professionals, and retirees alike. With its lush landscapes, friendly neighborhoods, and an array of amenities, South Chesapeake welcomes you to experience the best of Virginia living.

One of the standout features of homes in South Chesapeake is their stunning wooded exteriors. Imagine stepping out of your front door to be greeted by the gentle rustle of leaves and the soft chirping of birds. Many properties here are surrounded by mature trees and natural greenery, creating a serene atmosphere that invites relaxation and outdoor enjoyment. These wooded homes not only provide a picturesque backdrop but also offer a sense of privacy and seclusion, making them perfect for those seeking a peaceful retreat from the hustle and bustle of everyday life.

In addition to the natural beauty, South Chesapeake boasts excellent schools, parks, and recreational facilities, ensuring that residents have access to a vibrant lifestyle. Whether you’re exploring the scenic trails, enjoying community events, or indulging in local dining, there’s always something to do in this charming city.

With its unique blend of nature and community spirit, South Chesapeake is more than just a place to live; it's a place to thrive. Come discover your dream home among the wooded wonders of South Chesapeake, where every day feels like a getaway!

Newest South Chesapeake Homes with Wooded Exterior features

$665,000

4 Beds ⋅ 3 Baths ⋅ 10652967 MLS

This home truly has it all! Welcome to this beautiful 4-bedroom, 3-full-bath home in the highly desirable Las Gaviotas golf course community. Offering 3,371 square feet of thoughtfully designed living space, this home immediately impresses with beautiful flooring and an inviting, open feel. Enjoy peaceful living along a quiet tidal creek from the Elizabeth River, where changing tides, abundant wildlife, and natural beauty create a truly serene backyard setting. Relax on the updated Trex deck and enjoy the peaceful views, or take in the scenery from the inviting sitting room just off the living room, where gorgeous windows bring the beauty of the outdoors inside. The flexible floor plan includes a first-floor bedroom, dedicated home office/gym, and an upstairs bonus room—providing plenty of space for guests, work, hobbies, or entertaining. Numerous recent updates provide peace of mind, including new ductwork in attic and crawlspace (2025), roof and skylight (2024), water heater (2024), Prodigy insulated siding, fascia and rain gutters (2024), Bosch BOVA upstairs HVAC system (2022), Trex decking (2023), first-floor LVP flooring (2021), and crawlspace dehumidifier (2026). With golf-course community living, a peaceful tidal-creek setting, abundant natural light, and an impressive list of updates, this is a home you won’t want to miss.

419 Granada Drive, South Chesapeake

$998,895

5 Beds ⋅ 3.1 Baths ⋅ 10652907 MLS

Experience luxury living in this one-of-a-kind Chesapeake retreat, nestled on a 3-acre lot in the Grassfield School District. This custom-built home blends modern comfort with timeless charm, offering an open-concept first floor design for today's lifestyle. The spacious family room flows seamlessly into the remodeled 2024 kitchen, with direct access to the back deck for everyday relaxation or entertaining guests. Choose between two generous primary suites. First floor primary suite features a gas fireplace, dual closets, and a sitting/office area. Second floor primary suite privately located above 3-car garage, offering separation from the additional upstairs bedrooms. Enjoy abundant space for hobbies and storage with two powered sheds, plus peace of mind from the new encapsulated crawl space with vapor barrier. Major upgrades, including the roof, HVAC, and kitchen in 2024, ensures comfort and efficiency for years to come. This exceptional property delivers a rare combination of privacy, space, and freedom with no HOA restrictions, making it a true Chesapeake gem.

1910 Hallmark Way, South Chesapeake

$574,900

4 Beds ⋅ 2.1 Baths ⋅ 10653018 MLS

Located in Oak Bridge Forest, this 4-bedroom, 2.5-bath home offers a spacious layout, an oversized 2-car garage, and a large backyard made for enjoying the outdoors. Inside, a two-story foyer welcomes you into a light-filled floor plan featuring new laminate flooring, installed in 2025, throughout most of the home. The custom-designed kitchen received a complete makeover in 2025 and opens to the family room, creating an easy flow for everyday living and entertaining. Upstairs, the spacious primary suite features a private bath with a double vanity, walk-in shower, and jetted tub, with three additional bedrooms and a second full bath completing the level. Out back, mature landscaping and trees surround an in-ground pool with a new liner installed in 2024 and new pool heater added in 2025. A Trex deck provides additional space to relax or entertain. Additional features include a tankless water heater, sprinkler system, smart-home capabilities, Ring doorbell and exterior security cameras, plus an Invisible Fence encompassing the front and backyard. No HOA! With generous indoor and outdoor space, thoughtful updates, and a backyard ready for pool days and entertaining, this Oak Bridge Forest home has plenty to offer. Incentives may be available through preferred partners. Contact listing agent for details and eligibility.

733 Dissdale Lane, South Chesapeake

$650,000

5 Beds ⋅ 2.1 Baths ⋅ 10652716 MLS

Custom 5-bedroom, 2.5-bath Chesapeake home on a huge half-acre lot, currently zoned for Grassfield High School! This beautifully updated home features an open floor plan, pickled oak hardwood floors, quartz countertops, stainless steel appliances, gas range, custom barn doors, and European-inspired lighting and fixtures. The spacious primary suite offers cathedral ceilings, dual closets, and a private deck with peaceful wooded views. The spa-like primary bath features a freestanding soaking tub and custom porcelain-and-glass shower. Outside, enjoy an expansive deck and plenty of room for outdoor living, entertaining, and recreation. If you’ve been searching for a custom Chesapeake home with space, style, updates, and a large lot, this one deserves a closer look. Schedule your tour today!

2100 Millville Road, South Chesapeake

$749,000

6 Beds ⋅ 3 Baths ⋅ 10652745 MLS

Welcome to this beautiful brick home in the heart of Great Bridge! Situated on a quiet cul-de-sac, this home has it all! The foyer and entrance way are stunning and extend two stories and include a beautiful stair case. A gorgeous new primary shower, trayed primary bedroom ceiling, hardwood flooring and a private deck that offers a peaceful, wooded view. The first floor bedroom/office has direct access to a full bathroom with newer vanity and is just right for multi-generational living. Both HVAC systems are two years young. The heavy lifting has been done here, this one won't last long! See it today before it is SOLD!!!

909 Brice Court, South Chesapeake

$1,000,000

6 Beds ⋅ 3 Baths ⋅ 10652479 MLS

Open House Sat Sept 12 1-3pm. Modern Farmhouse Charm Meets Turnkey Living in Desirable Chesapeake! Discover the modern farmhouse you’ve been dreaming of, where peaceful country living meets thoughtful, top-to-bottom renovation. Set on serene acreage with panoramic wooded views. It embraces the natural surroundings. This beautifully refreshed home is ideal for extended family/multi generational living. Natural light fills the home, showcasing new flooring, fresh interior paint, updated lighting, and beautifully renovated bathrooms. The completely redesigned custom kitchen is the heart of the home, featuring quartz countertops, ceramic backsplash, abundant prep space, an inviting eat-in area and a KitchenAid appliance suite, ideal for everyday living and entertaining. The expansive living area offers plenty of room to gather, while the renovated wood-burning fireplace creates a cozy focal point with a new firebox, flue, chimney cap, and Buck Stove-style insert. Step onto the Trex deck with PVC railing and enjoy peaceful wooded views from the living space, primary suite or deck. The primary suite is a true retreat, featuring a custom-tiled shower with built-in bench and generous niche, deep soaking tub, double vanity and ceramic tile flooring. The expansive custom closet with built ins provides all the space you have been longing for. Additional improvements include an encapsulated crawlspace with dehumidifier, new septic system designed for 10 occupants, finished room over the garage with generous storage, updated downstairs ductwork, new interior and exterior doors and hardware, new lighting throughout, and a freshly graded crushed-aggregate driveway. The painted brick exterior adds a fresh, modern look while preserving brick’s timeless durability and character. Best of all, the home features a highly energy-efficient geothermal HVAC system. From the crawlspace to the exterior, virtually nothing has been overlooked. Renovated by New Again Houses VB. It offers the feel of quality new construction without sacrificing character, space or setting. See it today!

3132 Benefit Road, South Chesapeake

$769,000

5 Beds ⋅ 3 Baths ⋅ 10651816 MLS

Stunning one-owner home on 3 treed acres in the sought-after Hickory High School district, with easy access to Virginia Beach! Custom hardwood floors and trim/woodwork throughout, brand new carpet, and new luxury vinyl in the rec room off the garage. Main floor is 100% hardwood. 5 bedrooms plus two bonus rooms over the garage — great for a teenage suite or mother-in-law suite. Spacious great room with fireplace, formal dining room, and breakfast area off the kitchen. Remodeled kitchen features granite countertops, double oven, double sink, and a generous pantry. First floor offers a shelved library/home office. Florida room with screens and Andersen windows throughout, plus skylights including one in the primary suite. Newer Trex composite deck and storage building in back. Encapsulated crawlspace w/ sump pump & dehumidifier (JES). Well on-site, city water, septic. HVAC serviced annually. Lots of space to grow in this sturdy home!

1204 Murray Drive, South Chesapeake

$275,000

3 Beds ⋅ 1.1 Baths ⋅ 10651743 MLS

Room to garden, create, and entertain. A home designed for real use! Located at the end of a dead-end street on a cul-de-sac, this 3-bedroom, 1.5-bath home offers hardwood floors, a comfortable living area, and a full kitchen suite with all the countertop space, cabinets, and storage you need. The house only gets better outside, with an exceptional amount of usable outdoor space. In the front, two driveways provide flexible parking, and a vivacious garden frames the yard and house, leading you to the greenhouse. In the backyard is a large detached workshop, an extra storage shed, a massive deck for entertaining, a separate fire-pit area, and a ready-to-grow garden featuring raised beds and garden arches. Whether you're working on a project, growing fresh produce, or hosting friends, this property offers the space and versatility to make this house the one where everyone gathers.

2704 Misty Point Road, South Chesapeake

$1,519,000

5 Beds ⋅ 4.1 Baths ⋅ 10651679 MLS

Stunning property situated in the heart of Great Bridge on 3 acres! Brand new gourmet kitchen with 6 burner Cosmo range, additional prep sink, new top of the line appliances and custom cabinetry. All new paint, flooring and completely renovated baths and stairwells on first two primary living levels. Bonus third floor complete with full bath, new paint and new flooring! HUGE primary suite complete with fireplace, fantastic walk-in closet and beautiful new bath. The detached 3.5 car garage includes a garage apartment with kitchenette and full bath. New windows, roof, gutters, soffits and pool liner. Absolutely amazing opportunity to secure this gorgeous, move-in ready property. Awesome enclosed patio with hot tub as well as an outdoor kitchen/bar area. This is an entertainer's dream! See it today before it is SOLD!

641 Ravenwoods Drive, South Chesapeake

$419,900

3 Beds ⋅ 1.1 Baths ⋅ 10651314 MLS

Welcome to this beautifully renovated Great Bridge classic! This all-brick ranch sits on an expansive half-acre, wood-lined lot and blends timeless charm with thoughtful 2025 updates. The home was completely renovated in 2025, featuring new flooring, appliances, a refreshed kitchen, and updated bathrooms. The spacious living room is filled with natural light from oversized windows and offers a cozy wood-burning fireplace. A convenient attached one-car garage provides added storage and functionality. Outside, enjoy the expansive, private yard surrounded by mature trees perfect for entertaining, gardening, or simply relaxing. Zoned for all highly sought-after Great Bridge schools, this home offers an exceptional opportunity in one of Chesapeake's most desirable areas!

229 Cedar Road, South Chesapeake

$399,000

3 Beds ⋅ 2 Baths ⋅ 10650546 MLS

Calling all investors! Opportunity awaits at 844 Joanne Circle. Situated on approximately 0.74 acres in the Hickory School District, this 2,051-square-foot home offers three bedrooms, two full bathrooms, and a cozy fireplace. The large, treed, fenced-in backyard provides plenty of space and potential. Built in 1980, the home is ready for someone to bring their vision and personal touches. Conveniently located near shopping, interstates, and the bypass to the Outer Banks. Being sold as is. Come check it out today!

844 Jo Anne Circle, South Chesapeake

$1,500,000

5 Beds ⋅ 3.1 Baths ⋅ 10650552 MLS

A builder's own estate — private, impeccable, and set on approximately eight wooded acres at the end of a quiet Chesapeake cul-de-sac. Custom-built by the builder for his own family, this brick-and-stone home reflects a level of care you rarely find. Nothing here has been left untouched; it lives like new construction. A long gravel drive winds past mature trees to the home, where a sweeping front porch offers multiple entries and room to linger. Deer, turkey, and other wildlife are frequent visitors. Inside, a grand open floor plan rises to cathedral ceilings, finished with updated tile flooring, crown molding, and Hunter ceiling fans. The living area anchors around a dramatic stone fireplace and flows into an eat-in kitchen with rustic cabinetry, updated KitchenAid appliances, an electric cooktop, and a large center island with bar seating. The first floor holds a spacious primary suite, generously sized baths, and a well-placed Jack-and-Jill. Upstairs, brand-new carpet runs through bedrooms of exceptional size, and the primary closet is fitted with extensive custom built-ins. The two-story garage apartment is a standout, two bedrooms, 1.5 baths, multiple living areas, and a full eat-in kitchen, great for guests, multigenerational living, or income potential. The garages themselves have been freshly painted white, bright and spotless. Recent improvements include fresh paint throughout, LED lighting, updated kitchen and bath fixtures, two new HVAC units, a mini-split serving the room over the garage, smoke detectors, smart locks, and an on-demand propane water heater. Estate infrastructure is equally serious: 600-amp electrical service, a four-inch private well with pump house, a new water-softening system, hard-ducted HVAC, an illuminated crawl space, and a septic system serviced in 2026. A concrete parking pad completes the property. Privacy, craftsmanship, and acreage — a genuinely distinctive Chesapeake estate.

1120 Kathleen Lane, South Chesapeake

Start Your Search

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.