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$367,000
4 Beds 3 Baths 10646172 MLS
Welcome home to this quality built and beautifully maintained 4-bedroom, 3-bathroom brick ranch, tucked on a spacious 1/4+ acre lot, in a quiet Chesapeake neighborhood. Classic all-brick construction, a durable dimensional shingle roof, and great curb appeal make this home as solid as it is inviting. Step inside to a comfortable single story layout offering easy, one level living that could be great for families, downsizers, or anyone craving low maintenance simplicity. The attached one car garage adds convenience, while the second attached garage in the back of the home offers a great workshop or possibly even a future bonus room or kitchen that could turn this into a true in law suite. The possibilities are endless. Out back, enjoy your own private retreat: a spacious wooden deck under a charming pergola to enjoy a morning coffee or evening gatherings, plus a paver patio that can be used for grilling and/or simply entertaining. Mature trees and hedges provide natural privacy, creating a peaceful backyard escape. Located in a well established Chesapeake community that combines classic character with everyday simplicity as well as functionality.

1916 Chesapeake Avenue, Central Chesapeake

$510,000
4 Beds 2.1 Baths 10645829 MLS
WELCOME HOME! Tucked away on a quiet cul de sac and set on nearly an acre backing to peaceful woods, this beautifully maintained home offers the perfect blend of privacy, outdoor living, and everyday convenience. Whether you’re enjoying your morning coffee in the screened gazebo or entertaining family and friends, you’ll appreciate the peaceful setting this property provides. Inside, you’ll find stainless steel appliances, a spacious walk in pantry, a cozy gas fireplace, and thoughtful updates throughout, including a new roof installed in 2024. A transferable 2-10 Home Warranty provides added peace of mind for the next owner. Conveniently located near Interstate 64, Route 17, shopping, dining, and major military installations throughout Hampton Roads, this home offers the ideal balance of tranquility and accessibility. Don’t miss your opportunity to make this exceptional property your next home. Schedule your private showing today!

104 Bishops Court, South Chesapeake

$479,900
4 Beds 2 Baths 10645772 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. 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 Dr Drive, South Chesapeake

$628,900
6 Beds 3 Baths 10645483 MLS
Buy Now-Close in Late October with up to $20,000 buyer closing cost with acceptable agreement. Rare 6-bedroom opportunity with an ideal multigenerational layout! The first floor features a bedroom, adjacent flex room, and modified curb less shower, offering exceptional flexibility and accessibility. Beautiful neutral décor, 9' ceilings, hardwood floors, elegant crown molding, and a huge FROG provide plenty of room for everyone. The spacious primary suite features hardwood floors and two walk-in closets, plus convenient second-floor laundry. Enjoy the large fenced backyard with plenty of room to add a pool, detached shed, private well for economical lawn irrigation, and attached 2-car garage. Meticulously maintained with annual service contracts on the HVAC, tankless water heater and crawl space. Seller will provide a termite/moisture letter. Tucked into a quiet location that neighbors love, with schools nearby and convenient access to Millville Rd. and Veterans Bridge.

1816 Sunsprite Loop, South Chesapeake

$594,000
4 Beds 2.1 Baths 10645393 MLS
Premium location in one of Western Branch’s most sought-after neighborhoods & schools. Beautiful, manicured homes w/large lots & no homeowner’s association. Just minutes to 664 & ALL of Hampton Roads Military bases, shopping & entertainment and medical facilities. Step inside to a welcoming foyer that leads to a formal dining room, living room and a custom kitchen with an Island. The sunken den features a gas fireplace which exits to a multi-level deck for cookouts and entertaining. The upstairs features a primary suite for a private retreat with an en-suite bath, a large walk-in closet for keeping all your items organized, while two additional bedrooms (all with walk-in closets) provide versatility for guests or even a game (flex) room. In addition, a 4th bedroom is located over the 576 SQFT. Attached garage. New interior paint and carpet, move in ready

1416 Pine Grove Lane, West Chesapeake

$315,000
3 Beds 1 Baths 10645059 MLS
This lovely 3 bedroom/1 bath abode is fresh, charming and a perfect fit for the whole family! Enjoy the benefits of solar panels that keep energy costs low. The spacious backyard is ideal for curious kids to explore, energetic pups to play fetch or a small-scale gardener’s dreams to come true. Gorgeous warm wooden cabinets , coffee bar, custom island , pantry and gas stove create a luxurious feel in this gourmet kitchen. Enjoy time in the open family room complete with striking wood flooring, a cozy and comfortable space for family movie nights and memory making, find a bonus room that offers endless possibilities creates a cozy playroom, a productive home office or transform it into an extra bedroom. Take comfort in the attractive brick exterior of the home as it’s sure to stay tidy and effortless to maintain for years to come. Check out this wonderful opportunity to live the good life in Chesapeake!

3944 Port Road Road, Central Chesapeake

$579,000
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

$750,000
5 Beds 2.1 Baths 10645076 MLS
Why wait on new construction when this one's already done? This home was taken all the way down to the foundation and completely rebuilt and expanded — outside of one corner of the home everything here is new. Home inspection is complete, every item addressed, so you can move in with genuine peace of mind. Tucked away on a quiet country road in Chesapeake and surrounded by 3 peaceful acres of mature trees, this modern farmhouse ranch offers the privacy and charm buyers dream about. Huge wraparound-feel porches front and back give you outdoor living space to spare, and the wide-open yard makes this property feel like a true retreat. Inside, gorgeous LVP flooring flows throughout, while the spacious living area with a stunning brick fireplace creates a warm gathering space. The farmhouse-inspired kitchen features white cabinetry, an oversized island with bar seating, and ample storage. Bedrooms are thoughtfully spaced for added privacy, while the hall bath offers a double vanity, step-in shower, and beautiful natural light. The primary suite feels like its own getaway, with private porch access, dual closets, and a spa-style bath featuring a floor-to-ceiling marble-tiled shower. A detached storage shed conveys, and the sprawling backyard offers endless possibilities — gardening, entertaining, or future additions. All the character of country living, with the peace of mind of a brand new home. Welcome home.

1629 Shillelagh 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

$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

$390,000
3 Beds 2.1 Baths 10644197 MLS
Welcome home to this stunning 3-bedroom, 2.5-bathroom gem nestled in one of Chesapeake's most serene and desirable neighborhoods. The main level boasts a bright and cozy living room that flows seamlessly into a stylish kitchen, making everyday living and entertaining a breeze. Upstairs, you will find spacious, private bedrooms and well-appointed bathrooms. Outside is a generous backyard that serves as your own private oasis, perfect for hosting weekend gatherings, gardening, or relaxing in the sun. Situated in a peaceful community just minutes from local shopping, dining, schools, and major commuter routes, this home truly has it all. Don't miss the opportunity to make this house your home sweet home! Schedule your private tour today! Listing photos contain virtually staged media.

601 Lord Byron Court, South Chesapeake

$420,000
3 Beds 2 Baths 10644472 MLS
Experience the charm of country living without sacrificing convenience! Nestled in Chesapeake's highly desirable Grassfield area, this property offers the perfect blend of privacy, open space, and everyday comfort. Enjoy peaceful surroundings with room to relax, entertain, garden, or simply take in the natural beauty. The thoughtfully designed home features inviting living spaces filled with natural light and a layout that's great for both everyday living and special gatherings. Located just minutes from shopping, dining, schools, and major commuter routes, you'll loving having the best of both worlds-quiet rural living with city conveniences nearby. Whether you're looking for your forever home or your own private retreat, this is a rare opportunity you won't want to miss. Schedule your private tour today!

4321 Ballahack Road, South Chesapeake

$795,000
6 Beds 3.1 Baths 10643149 MLS
Well-maintained, spacious home on a prime lot in the beautiful Riverwalk community. New Roof, all new Windows, new paint interior and exterior, and new carpet in 2026! Beautiful wood floors in living and dining areas. Six bedrooms, 3 full and 1 half baths. Designed for those who love to entertain, the expansive floor plan offers elegant gathering spaces, abundant natural light, a formal butler station off the dining room. and exceptional flow throughout. The spacious eat-in kitchen and bar-top seating area open to the inviting family room with a cozy fireplace. Three additional bedrooms are located on the second level, including a versatile FROG that can serve as the 6th bedroom, home office, or recreation room. Current cooktop and built-in microwave to be replaced; buyer can choose. Large back deck with gas hookup. Residents of Riverwalk enjoy exceptional neighborhood amenities, including walking trails, a community pool, boat ramp and dock, playground, and a popular summer swim team. This is a wonderful opportunity to own a meticulously cared-for home in one of Chesapeake’s most desirable communities.

804 River Strand, South Chesapeake

$1,259,997
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

$429,900
4 Beds 2 Baths 10644168 MLS
Do not look any further, this wonderful brick ranch is just waiting for you! Make this your home with 4 spacious bedrooms, 2 full baths, large living room with electric F/P and HW floors, dining room for all your family meals, family room with electric F/P. The kitchen has breakfast bar and all appliances convey, Large 2 car garage. You will be delighted with the backyard deck or enjoy the 4 seasons sunporch (approx 185 sq ft) to relax in after swimming in your luxurious 20x40 salt water pool. Backyard shed for pool toys and lawn equipment. Plenty of storage in the partially floored attic with walk up stairs.Home freshly painted, roof replaced 2020, pool liner 2021, pool pump 2025, Hot water heater 2023, Dishwasher 2026. Close to schools, shopping and interstate. This home is just waiting for you to move on in. Call for your appointment today before its gone!!

4117 Hawksley Drive, West 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.