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$299,900
4 Beds 2.1 Baths 10645218 MLS
Welcome to 1243 Damyien Arch, a beautiful townhome in the heart of Chesapeake's Greenbrier area! This spacious 3 possible 4-bedroom, 2.5-bath home offers an open and inviting floor plan designed for comfortable everyday living and effortless entertaining. The bright living area flows seamlessly into the dining space and kitchen, while the generous primary suite provides a private retreat with ample closet space and an en-suite bath. Enjoy low-maintenance living with a private patio, attached garage, and convenient access to shopping, dining, parks, major interstates, military bases, and Chesapeake Regional Medical Center. Located in an established neighborhood, this home is an excellent opportunity for anyone seeking a centrally located home with easy access to everything Hampton Roads has to offer. Schedule your private showing today and make this Chesapeake gem your new home!

1243 Damyien Arch, South Chesapeake

$645,000
4 Beds 2.1 Baths 10645288 MLS
First Time Buyer 5.5 rate, low down, NO PMI! Joseph’s Meadow MODEL GPS 369 Scotland Ln. Chesapeake. Nestled in Greenbrier come visit the newest community by renowned local builder. Lily Cottage welcomes you w/ a full front porch, soaring 10-foot ceilings, & beautiful hardwood floors throughout the first floor. Designed for entertaining, the open-concept layout seamlessly connects the living room, dining area, & stunning chef’s kitchen featuring a 9-foot quartz island, custom hood, & oversized walk-in pantry. Mudroom & powder room are conveniently tucked away by 2-car garage. Upstairs, a sun-filled loft, two spacious bedrooms, loft (opt 4th), & a large laundry room provide exceptional functionality. The private primary suite offers a custom walk-in closet & spa-inspired bath w/ quartz countertops, dual vanities, freestanding tub, tiled shower, & private water closet. Easy living with professionally managed grounds ensures low-maintenance living, making your dream truly a peaceful haven.

365 Scotland Lane, South Chesapeake

$585,000
4 Beds 2.1 Baths 10645167 MLS
Beautifully updated and impeccably maintained, this exceptional 4BR/2.5BA home offers thoughtfully designed living space in the highly sought-after Kemp Woods neighborhood of Chesapeake. Nestled on a quiet, tree-lined street, this move-in ready home perfectly blends timeless elegance, quality craftsmanship, & modern updates. Step inside to an inviting floor plan filled with natural light, with rich hardwood flooring, elegant plantation shutters, and spacious living areas. Gourmet kitchen is designed to impress, featuring tall cabinetry, built-in appliances, abundant counter space, & oversized breakfast area surrounded by windows that fill the space with natural light. Spacious primary suite is a true private retreat, complete with large walk-in closet & stunning, spa-inspired ensuite featuring beautifully tiled, oversized frameless glass walk-in shower, dual vanity, designer lighting, & luxurious finishes that create a resort-like experience at home. 3 additional generously sized bedrooms. Seamlessly extending the living space outdoors, both the family room and breakfast area open to an expansive multi-level deck overlooking the private backyard. Designed for entertaining and everyday enjoyment, this outdoor retreat offers oversized deck and a hot tub—perfect for summer gatherings, peaceful evenings, or relaxing under the stars. Major improvements provide exceptional peace of mind, including a roof, two-zone HVAC system, & numerous updates completed within the last 5 years, allowing the next owner to simply move in and enjoy. Conveniently located just minutes from Greenbrier’s premier shopping, dining, entertainment, parks, hospitals, and major commuter routes including I-64, this home offers the perfect balance of convenience and the quiet charm of one of Chesapeake’s most established and desirable neighborhoods. Some photos were virtually staged or digitally enhanced for marketing purposes to help buyers visualize the property’s potential. Schedule your showing today to make this house YOUR HOME!!

1045 Winchester Way, South Chesapeake

$629,900
4 Beds 2.1 Baths 10645157 MLS
BUY THIS AWESOME HOME, WE'LL BUY YOURS!* Welcome to your low-maintenance luxury retreat in the sought-after 23322 zip code! This beautifully designed 4-bedroom, 2.5-bath home offers 2,598 sq ft of stylish, comfortable living with minimal upkeep. The highlight is the exceptional outdoor living space—a 529 sq ft covered, screened patio with premium epoxy flooring for entertaining, outdoor dining, or relaxing in privacy. An additional patio and custom walkway are surrounded by professionally landscaped, easy-care grounds. Enjoy a true lock-and-leave lifestyle with an HOA that maintains the front yard, giving you more time to enjoy life instead of yard work. Resort-style community amenities are just steps away, while shopping, dining, parks, and major commuter routes are all nearby. This home offers the perfect blend of luxury, convenience, and carefree living.

1910 Briton Lane, South Chesapeake

$575,000
4 Beds 2.1 Baths 10645016 MLS
Welcome to this beautifully maintained 4-bedroom, 2.5-bath home offering an open-concept floor plan designed for comfortable everyday living and effortless entertaining. Conveniently located near shopping, dining, and with easy interstate access, this home combines comfort with convenience. Relax and unwind on the spacious deck while enjoying peaceful views of the pond and the surrounding wildlife. The generous primary suite features a large walk-in closet, providing plenty of storage space. The well-appointed kitchen includes a gas range, a large pantry, and ample workspace for cooking and gathering. Located in the highly sought-after Chesapeake School District, this home also offers numerous valuable upgrades, including a new roof (2024), HVAC system (2024), and water heater (2021). Additional features include solar panels for energy efficiency, an irrigation system with a dedicated well, a security system, and the washer and dryer, all of which convey with the home.

1311 Piedmont Arch, South Chesapeake

$780,000
4 Beds 2.2 Baths 10644986 MLS
Welcome Home to this newly remodeled from top to bottom classic Home in Hickory's Pleasant Ridge neighborhood. Nestled back on this 3+ acre lot is this elegant and stylish two-story residence with new siding, windows, trim, fascia - the ultimate facelift. Enter into your foyer with new floors and fresh paint, new hardware, finishes, and lighting flow through this ideal layout. Formal living or dining off the left of foyer and to the right is large great room. Half bath for guests. Kitchen is spacious and feat. breakfast area and access to rear FROG stairs and garage. Second level feat. large primary suite with ensuite bath, two secondary bedrooms, hall bath, and FROG with half bath for convenience. Large newly installed deck leads to massive backyard waiting for you to put your stamp on. Call this Home Today!

705 Pleasant Ridge Court, South Chesapeake

$599,999
4 Beds 2 Baths 10644979 MLS
Welcome to this fully remodeled all-brick ranch located in the Hickory area of Chesapeake. Offering 4 bedrooms, 2 updated bathrooms, and situated on approximately 3 acres, this property provides generous indoor and outdoor living space. Interior updates include luxury vinyl plank flooring, tiled showers, granite countertops, stainless steel appliances, and an open, light-filled layout designed for everyday living and entertaining. Outdoor features include a covered front porch, an expansive rear deck, and a private deck accessible from the primary suite. Additional improvements include a newly poured driveway and a 50-AMP power pole ready for RV hookup. This move-in-ready home combines updated finishes with functional living space in a convenient Chesapeake location.

913 Long Ridge Road, South Chesapeake

$550,000
4 Beds 3 Baths 10644867 MLS
Welcome home to this beautiful Craftsman-style ranch in highly desirable Culpepper Landing! This spacious 4-bedroom, 3-bath home offers approximately 2,380 square feet of thoughtfully designed living space with an open floor plan, soaring 10-foot ceilings, hardwood floors, upgraded trim, and surround sound in the living room. The gourmet kitchen features granite countertops, custom cabinetry, a large center island with bar seating, and ample storage—perfect for large families or entertaining. The first-floor primary suite offers a tray ceiling, walk-in closet, and an ensuite bath with double vanities, a garden tub, and a tiled walk-in shower. A finished room over the garage with a full bath and walk-in closet provides the perfect guest suite, home office, or flex space. Enjoy relaxing on the inviting front and side porches or entertaining on the rear deck. Additional features include a two-car attached garage, sprinkler system, and garage door opener with a transferable warranty and MyQ smart access for convenient remote operation and secure package delivery. Inground Sprinkler System has recently been inspected, a new back flow preventer was added and sprinkler heads relocated to accommodate a future fence. Interior professionally painted, new easy open window blinds installed thoughout w/4 yr warranty (2025). Located across from the neighborhood dog park, Culpepper Landing offers outstanding amenities including a clubhouse, community pool, fitness center, playgrounds, and walking trails, all with convenient access to shopping, dining, military bases, and major interstates.

3209 Dodd Drive, South Chesapeake

$609,900
4 Beds 3.1 Baths 10644569 MLS
100% move-in ready in the Grassfield school district! This open floor plan offers quality finishes throughout. Hardwood flooring runs throughout the main living areas. The first-floor office/study has direct access to the wraparound front porch. The family room opens to the dining area and spacious kitchen featuring granite countertops, white soft-close cabinets, a large island, stainless steel appliances, and a walk-in pantry. Enjoy the private, fully fenced backyard with a custom paver patio. The room over the garage is a private guest suite with a full bath and separate access from the foyer. Upstairs also offers a loft, 2 spacious bedrooms, and the primary suite with a large walk-in closet, soaking tub, oversized tiled shower with custom glass enclosure, and private water closet. No HOA. Convenient to schools, shopping, dining, and major commuter routes.

1933 Reefwood Road, South Chesapeake

$539,900
4 Beds 3.1 Baths 10644619 MLS
Welcome to your home in the highly sought after Grassfield Meadows community of Chesapeake, zoned for the desirable Grassfield school district! This beautiful townhome features custom accent walls that add warmth and character throughout. With 4 spacious bedrooms and 3.5 bathrooms, the flexible layout is perfect for today's lifestyle. The first floor offers an ideal space for guests, a home office or an in-law suite. The open concept main living area is bright and inviting, great for entertaining or everyday comfort. Go out onto your private balcony to enjoy morning coffee or evening relaxation. The third-floor hosts three more bedrooms and two full baths, including a tranquil primary suite. Community amenities include a covered pavilion with grilling area, dog park, fitness park and playground for year-round enjoyment. Conveniently located near shopping, dining and major commuter routes, this move-in- ready home offers the perfect blend of style, comfort and convenience.

1837 Honey Milk Road, South Chesapeake

$594,900
4 Beds 2.1 Baths 10644498 MLS
Beautiful ranch-style home tucked away on a quiet cul-de-sac in Chesapeake’s Bayberry Forest! This spacious 4-bedroom, 2.5-bath home offers generous living areas, an attached 2-car garage and thoughtful updates throughout. The fenced backyard is made for relaxing or entertaining with a deck, storage shed and beautiful landscaping. Inside, enjoy a fully conditioned sunroom for year-round use, a finished room over the garage, large bedrooms with step-in showers in both bathrooms. Recent upgrades include a new HVAC system in 2024, new LVP flooring, an encapsulated crawl space and a whole-house generator for added peace of mind. The bright, open kitchen features an island with guest seating plus room for a table, while the formal dining room gives you extra space for gatherings. Between the inviting living room and comfortable den with gas fireplace, there is plenty of room to enjoy family and friends. Centrally located near shopping, dining, interstate 64 and bases.

1305 Forest Point Drive, South Chesapeake

$595,000
4 Beds 2.1 Baths 10644529 MLS
Welcome to 909 Wheatfield Way situated at the back of a cul-de-sac with a covered front porch. The foyer entrance opens to the arched entrance to the formal dining room with crown molding and chair rail and the formal living room. The kitchen features a Butler's Pantry, tile flooring, newer appliances with gas range, dishwasher and hood. Kitchen also features granite tops & an island with power. The great room is open to the kitchen and features a gas fireplace for relaxing get togethers. The second floor features the Primary bedroom with vaulted ceilings, dual walk-in closets, private bath with tile floors, dual sinks, garden tub & shower stall. The second floor also has 3 additional bedrooms and full bath. Situated at the back of the cul-de-sac with a large backyard, storage shed and patio for entertaining. Located with views of the 48-acre Chesapeake Arboretum protected space and just minutes from the Battlefield Blvd corridor with easy access to shopping, dining & hospitals.

909 Wheatfield Way, South Chesapeake

$499,900
4 Beds 2.1 Baths 10644597 MLS
Welcome to your dream Craftsman-style 4 bdrm 2 1/2 bath home w/a 2 car garage nestled in the heart of Chesapeake. This meticulously crafted residence offers a perfect blend of modern convenience & classic charm promising a lifestyle of comfort & sophistication. The heart of the home lies in the gourmet kitchen adorned w/luxurious granite countertops & equipped with stainless steel appliances. Whether you're whipping up a culinary masterpiece or enjoying a casual meal at the breakfast bar, this culinary haven is sure to inspire your inner chef. As you venture outdoors, discover & enjoy your own oasis in the backyard waiting for your personal touch. With its prime location in Chesapeake, you'll enjoy easy access to local amenities, schools & major thoroughfares, ensuring that every convenience is w/in reach. Projected completion is mid August 2026. The lot is almost 9400 sq ft. LVP flooring will be installed throughout the 1st floor. Photos from previous build. Make your appt today. Backyard fence being installed soon.

120 Taxus Street, South Chesapeake

$565,000
4 Beds 2.1 Baths 10644474 MLS
OPEN HOUSE SAT AUG. 1st 11AM TO 2 PM Step into this spacious & immaculate totally remodeled ranch in the much-desired Etheridge Woods neighborhood. Amazing newly designed open floor plan for a busy family and for entertaining. Brand new roof, newer HVAC. Totally renovated well-appointed open kitchen with built in stainless appliances and huge eating, entertainment area. Generous size primary suite with bath plus 3 additional bedrooms including FROG. Converted garage home for home office, gym, home school, etc. Floored attic for storage. Lovely backyard with screened porch, patio and 10X14 insulated workshop with electric and A/C. Quiet cul-de-sac lot. Hickory school district. This totally updated home is a must see!

1008 Chalbourne Drive, South Chesapeake

$389,000
4 Beds 2 Baths 10644668 MLS
Welcome home to 1421 Glendale Avenue! Designed for effortless living, where quality craftsmanship, modern style & everyday convenience come together in this beautifully updated 4-Bedroom, 2 Bathroom Ranch home w/exceptional indoor & outdoor living spaces in the heart of Chesapeake! The high-end custom eat-in kitchen features abundant cabinetry, granite countertops, stainless steel appliances, washer & dryer, custom tile backsplash & flooring, breakfast bar area that flows seamlessly to the open concept living & dining areas. The spacious primary suite includes a versatile bonus room, ample closets & private ensuite bathroom. Outdoors you'll find beautifully landscaped grounds, a fenced private backyard oasis offering plenty of space to enjoy the covered patio, marshmallows by the fire-pit, beautiful flower gardens, substantial vegetable, herb & fruit gardens…. and don’t miss out on the oversized insulated detached garage/workshop plus storage shed. Call today for your private tour!

1421 Glendale Avenue, South Chesapeake

$315,000
4 Beds 2 Baths 10644591 MLS
Charming one-level brick ranch offering 4 bedrooms plus a versatile bonus 5th bedroom attached to primary suite, perfect for a nursery, home office, sitting room, or flex space. Two updated full bathrooms. Equipped with two central air systems to serve addition to property, both less than 6 years old. Newer kitchen with granite countertops, new dishwasher and newer big size washer and dryer. The spacious primary suite includes two oversized closets with built-in shelving and drawers, providing exceptional storage and organization. Step outside to a large private backyard with a wood privacy fence- ideal for entertaining, cookouts, or relaxing outdoors. Conveniently located near shopping, dining, and with easy access to major interstates.

2641 Gilmerton Road, South Chesapeake

$499,900
4 Beds 2 Baths 10644453 MLS
Charming ranch with large backyard and pool! Enjoy the welcoming front porch before heading inside to the thoughtfully updated interior, where fresh paint and beautiful new LVP flooring create a bright, inviting atmosphere. New carpet in the room above the garage adds comfort and versatility to the home's flexible living space. Designed for both everyday living and effortless entertaining, the home features a living room, dining room, and a cozy family room accented by wood beams and a fireplace. At the heart of the home, the eat-in kitchen offers all new sleek cabinetry, granite countertops, and stainless steel appliances. Four spacious bedrooms provide comfortable accommodations, while both full bathrooms have been refreshed with stylish new vanities. Outside, you're sure to enjoy the fully fenced backyard featuring a spacious deck overlooking the swimming pool creating an inviting setting for relaxing, entertaining, or enjoying warm summer days. Two storage sheds provide additional room for lawn equipment, tools, or hobbies, while the attached garage adds everyday convenience and extra storage.

403 Caravelle Court N, South Chesapeake

$645,000
4 Beds 2.1 Baths 10644442 MLS
Experience the lifestyle you've been searching for in one of Chesapeake's most desirable communities, just minutes from top-rated Grassfield High School. This beautifully maintained home welcomes you with a charming front porch and gleaming hardwood floors throughout the main level. A versatile flex room that can be used for a home office, playroom, or sitting area, while the formal dining room flows into the updated chef's kitchen featuring granite countertops, refreshed cabinetry, and new stainless steel appliances. The kitchen opens to a spacious family room centered around a cozy fireplace and an inviting sunroom filled with natural light. Upstairs, the expansive primary suite offers a spa-inspired bath with dual vanities, a jetted tub, and a glass-enclosed shower, along with three additional bedrooms, a full bath, and a convenient second-floor laundry room. Step outside to your own private backyard retreat complete with a stamped concrete patio, sparkling in-ground pool, and fully fenced yard—ready for relaxing or entertaining all summer long. Additional upgrades include a tankless water heater, solar panels that significantly reduce electric costs, updated main-level lighting, and a VA assumable loan with an incredible 3% interest rate for qualified buyers. Tesla EV charger.

2101 Beeblossom Lane, South Chesapeake

$1,299,997
4 Beds 2.1 Baths 10644328 MLS
Custom 4,300+ sq ft estate on 3 private, wooded acres on historic Taft Rd., located in the Hickory/Grassfield school districts. Perfect blend of country living & city access. Inside features exceptional build quality, ornate plasterwork, dentil moulding, & dual staircases. The main level hosts a home office, living room with a wood fireplace, half bath, & a sunroom. The spacious kitchen boasts a center island & matte white cafe; appliances, leading to a laundry room & 2-car heated garage. Upstairs features 4 large bedrooms, including a primary suite with 2 walk-in closets & 3rd-floor access. 2 full baths feature luxury defogging mirrors. The 3rd floor is ideal for a 2nd living room/studio. Outside boasts a wrap-around porch, 32k-gal saltwater pool (new liner 2025; new pump/filter/salt cell 2026), Trex deck, heated 3-car detached garage with mini-split, carport, shed (new roof 2026), & pole barn. Features 400A service (200A panel), generator tie, & grill propane line. Move-in ready!

1741 Taft Road, South Chesapeake

$645,000
4 Beds 2.1 Baths 10644240 MLS
Vacation at home! Beautifully updated 4-bedroom, 2.5-bath home in sought-after Cheshire Forest and the desirable Great Bridge school district. The backyard is the star, transformed in 2024 with a saltwater in-ground pool with built-in hot tub, expansive patio, refreshed deck, fire pit, and hardtop gazebo with Blackstone grill, Traeger smoker, and two mini refrigerators. Fully fenced yard backs to the neighborhood lake with access for fishing or a lakeside stroll. Powered shed with well, plus deck furniture and pool accessories convey. Inside offers LVP flooring throughout, a spacious great room with gas fireplace, formal dining room with pocket doors, and a sunroom with mini-split (2024). Recent updates include HVAC (2025), water heater (2026), electrical panel (2024), windows (approx. 2021), new gutters, bath tile, plantation shutters, shiplap, roof (2014) and more. 2-car garage. Community amenities complete the package!

656 Parker Road, 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.