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$324,900
4 Beds 1 Baths 10645441 MLS
This beautifully updated property situated on a spacious corner lot of over a quarter acre in Chesapeake! Recent improvements completed in June 2026 include: a brand-new GAF architectural shingle roof, new gutters, new flooring throughout, and fresh interior paint, giving this home a clean, modern feel and added peace of mind. The versatile FLEX room offers endless possibilities and can easily serve as a 4th bedroom, home office, playroom, or home workout space to fit your lifestyle. Step outside to your fully fenced backyard retreat, designed for both relaxation and entertaining. Enjoy summer days in the above-ground pool and unwind or host gatherings under the pergola on the patio while appreciating the privacy this backyard provides. Conveniently located near shopping, dining, schools, and major interstates, this move-in-ready home combines thoughtful updates, flexible living space, and exceptional outdoor setting you won't want to miss.

2801 Southport Ave., 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

$599,999
4 Beds 2 Baths 10644979 MLS
Welcome to this beautifully remodeled all-brick ranch tucked into the peaceful Hickory area of Chesapeake, where country charm meets modern comfort on approximately 3 sprawling acres. This 4-bedroom, 2-bath gem has been thoughtfully updated from top to bottom, featuring luxury vinyl plank flooring, tiled showers, granite countertops, and stainless steel appliances throughout a bright, open layout made for both everyday living and easy entertaining. Step outside and fall in love with the lifestyle this property offers: relax on the covered front porch, host gatherings on the expansive rear deck, or unwind on your own private deck just off the primary suite. Dreaming of homegrown eggs? The property includes chicken coops, ready for you to raise your own flock and enjoy farm-fresh living right in your backyard. A newly poured driveway and a 50-AMP power pole with RV hookup round out the practical upgrades, making this move-in-ready retreat as functional as it is charming. With updated finishes, room to roam, and space to grow your own little homestead, this Chesapeake beauty is ready to welcome you home.

913 Long Ridge Road, South Chesapeake

$499,885
4 Beds 2.1 Baths 10644750 MLS
Beautifully renovated and move-in ready, this spacious 4-bedroom, 2.5-bath home offers approximately 2,621 square feet, including an addition that provides extra living space. The open and inviting main level features fresh luxury vinyl plank flooring, updated lighting, and a bright sunroom. The updated kitchen offers granite countertops, stainless steel appliances, and attractive cabinetry. Upstairs, you’ll find four comfortably sized bedrooms with new carpeting and updated bathrooms featuring modern ceramic tile. The home is equipped with gas heat and central air conditioning on the first floor and a heat pump serving the second floor. Additional features include an attached garage, a generous lot, and a roof replaced approximately in 2021. Conveniently located in Western Branch near shopping, dining, schools, and major roadways with access throughout Hampton Roads. Schedule your showing and see all this home has to offer.

4257 Meadow Wood Drive, West 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

$685,000
5 Beds 3 Baths 10643877 MLS
A Gem! Pristine condition all brick transitional on 1/3 acre cul de sac lot in Great Bridge. 5 bedrooms plus 1st floor 6th bedroom or office with ensuite. Open floor plan with huge updated kitchen (quartz counters), breakfast room and family room overlooking impeccably landscaped and treed backyard. Remodeled primary & hall bathrooms. 2 zone HVAC. Wood burning fireplace also plumbed for gas. Spacious family room, living and dining rooms, bedrooms and FROG. Screened porch with concrete floor. 2 car side loading garage with long driveway. Updates include windows, roof, 1st floor gas pack HVAC, garage door and leaf filter gutters. Award winning Cheshire Forest community. Amenities include clubhouse, pool, tennis/pickleball court, parks and playground. In-ground sprinkler system, appliances, and window treatments convey "as is". Home warranty.

810 Hedgerow Court, South Chesapeake

$700,000
4 Beds 3.1 Baths 10643713 MLS
Welcome home to this classic brick home tucked in a cul-de-sac, with comfortable living spaces, thoughtful updates, and a backyard made for enjoying Virginia summers. The main level offers inviting living and dining areas, a large bright kitchen with island seating, and an easy flow into the vaulted family room with skylights, a brick fireplace, and access to the deck and pool area. Upstairs, the spacious bedrooms offer flexibility for guests, hobbies, work, or everyday living. The primary suite features vaulted ceilings, generous closet space, and a large bath with a soaking tub set beneath a window-filled nook. Outside, enjoy an in-ground pool, deck space for relaxing or entertaining, mature landscaping, and a peaceful setting. Recent updates include new flooring, upstairs, HVAC, a new pool liner, an updated front door, refreshed lighting and fixtures, and new fencing. Come see all this home has to offer!

701 Aspen Forest Court, South Chesapeake

$440,000
6 Beds 3 Baths 10643653 MLS
15K INSTANT EQUITY!!!!!!! A peaceful neighborhood in the Deep Creek area of Chesapeake with close water views and wooded scenery. This home is one of the largest homes, in the neighborhood, spacious bedrooms 6 & 3 full bathrooms. This home features a modern open layout with generous living areas and a well-appointed kitchen open for entertaining. 3 first-floor bedrooms and 1 full bath provide ideal flexibility for guests or multi-generational living while the other 3 to include the Primary bedroom on the second floor. The home has a new LVP life proof floors, New paint, New carpet, New two car driveway with a wrap around sidewalk and a generous size yard for gathering a outdoor activities. Flood Insurance of 880 yearly (Never floods) SOME CLOSING COST ASSISTANCE AVAILABLE.

421 Plummer Drive, South Chesapeake

$379,900
3 Beds 2 Baths 10643565 MLS
Welcome to one of Chesapeake's best opportunities! This well-maintained brick ranch offers 1,976 square feet of comfortable living space with 3 bedrooms, 2 full bathrooms, and an oversized 520-square-foot attached two-car garage. The updated kitchen features quartz countertops and beautifully refreshed cabinetry, while numerous major improvements have already been completed, including a newer roof, inverter heat pump, refurbished concrete driveway and walkway, updated awning, LeafGuard gutters, and professional foundation repair. Situated on a generous 0.30-acre lot with no HOA and no flood insurance required, this home offers exceptional value, thoughtful updates, and pride of ownership throughout. Schedule your private showing today!

420 Oaklette Drive, Central Chesapeake

$295,000
2 Beds 1.1 Baths 10642955 MLS
Welcome home to this beautifully updated 2-bedroom, 1.5-bath townhome tucked away on a quiet cul-de-sac in desirable Las Gaviotas. Head inside to a spacious living area featuring a cozy brick fireplace, fresh finishes, and an inviting layout perfect for everyday living or entertaining. Recent improvements include fresh paint, new flooring, new carpet, an updated full bath, new rear deck, front porch railing, sliding glass doors, gutters, and water heater. Energy-efficient windows and kitchen appliances were replaced in 2020. Upstairs offers two generously sized bedrooms, a dual-entry bath, and a large hall closet for extra storage. Enjoy a private fenced backyard with a new deck, ideal for relaxing or entertaining. Conveniently located near shopping, restaurants, parks, major interstates, Chesapeake City Hall, and award-winning Grassfield schools, this move-in ready home is ready for its new owner.

300 San Roman Drive, South Chesapeake

$775,000
5 Beds 2.1 Baths 10642786 MLS
One of a kind property in Hickory area of Chesapeake with 2 (YES TWO) SFH that are legally deeded, WATERFRONT (ocean access) ~3.5 ac lot, with no neighbors in sight! Main house is over 3,000 sqft 5/2.5. Smaller house about 1200 sqft, 2/. Both have newer systems and New Roofs. Each home has its own Septic/Well system & pumped in 2024-large house/2025-small house. Property backs to 60 ft of riverfront that leads through the sounds and into the ocean. The main farmhouse has modern amenities but the old charm and character with original hardwoods, curved arches and entry ways, Juliet Balcony overlooking estate, 3rd floor finished attic bonus room and solid walk down basement foundation that can be turned into a finished room or used for storage. This home is solid and well maintained, being sold as is, seller to make no repairs. Call today for your private showing!

112 Station Road, South Chesapeake

$950,000
5 Beds 4 Baths 10642562 MLS
Welcome to your own private backyard retreat! This beautifully updated home offers the perfect blend of stylish interior living and incredible outdoor entertaining. Step outside to a true backyard oasis featuring a stunning 6-foot in-ground pool with a new liner and pump, a covered lounge area, outdoor fire pit, built-in bar, outdoor kitchen with grill, and plenty of space to host family and friends all season long. A screened porch conveniently connects the outdoor living space to the home, creating seamless indoor-outdoor living. Inside, the nearly renovated kitchen is the heart of the home, showcasing gorgeous marble countertops, a spacious center island, all LG appliances, bar-height seating, and a built-in desk area great for working from home or everyday organization. The open-concept design flows effortlessly into the inviting living room, making entertaining easy. Upstairs, you'll find generously sized bedrooms with abundant closet space, including a spacious room over the garage that offers endless possibilities for a media room, playroom, guest suite, or home office. The luxurious primary suite is a true retreat, featuring a cozy sitting area with its own fireplace, an oversized walk-in closet, and a beautifully appointed en-suite bath complete with dual-height vanities, a private water closet, soaking tub, and separate walk-in shower. Light wood-look luxury vinyl plank flooring adds warmth and elegance throughout the main living areas, while plush carpeting creates comfort upstairs. Thoughtfully updated and impeccably maintained, this home offers the perfect combination of comfort, style, and resort-style outdoor living. Don't miss the opportunity to make this exceptional property your next home!

129 Greengable Way, South Chesapeake

$879,000
3 Beds 2 Baths 10642255 MLS
If these walls could talk, they would tell you 175 years of stories. Rare pre-Civil War farmhouse charm meets modern comfort in this private retreat that feels like a vacation every day. This 2-story home is filled with character, featuring 4 fireplaces, gorgeous original hardwood floors, 10-foot ceilings, hand-sawed original moldings, intricate ceiling details, and antique lighting. The living room offers a cozy wood-burning stove, while the family room showcases coffered ceilings and original hardwood floors. The spacious primary suite stands out with a beautiful fireplace and a wall of built-in cabinetry offering storage rarely found in modern homes. Enjoy two laundry areas, including one in the ADU over the detached tandem 4-car garage, plus a flexible space for an office or mudroom off the back of the main house. Outside, unwind and entertain by the pool oasis, or sit on the 250 sqft covered porch. There is a huge new chicken coop (26), and 2 dog runs for that farm life as well as a shed (as is). The brick walkways are the original bricks from the chimney repurposed. Updates include painted kitchen cabinets/walls (26), sealed and painted metal roof with 20 year paint (26), new pool liner (25), encapsulated crawlspace with dehumidifier/support beams (25), 50-gallon hot water heater (25), HVAC, and ductwork (23), new steps and railing out to the pool (26), breaker upgrade to house (25) 2 solar systems one to the main house and one to the ADU/garage (23). More updates listed in agent remarks. Near Hickory schools, shopping, Bypass, and OBX. Come own a piece of history in Hickory!

2410 Centerville Turnpike, South Chesapeake

$440,000
4 Beds 2.1 Baths 10641959 MLS
Discover timeless charm in this beautiful, traditional home located in the heart of Chesapeake. Featuring 4 bedrooms, 2.5 bathrooms, and a spacious two-story layout, this home includes a bedroom with its own en suite bath, making it great for guests or added privacy. Gather around the cozy fireplace on cool evenings, or enjoy casual meals in the bright breakfast area. Step outside to a fully fenced backyard, great for entertaining, pets, or relaxing outdoors. Recent upgrades, including new siding and roof (2021) and a remodeled primary bathroom (2025), enhance both the home's beauty and value. An attached garage and attic complete this exceptional property. Don't miss your opportunity to make this Chesapeake gem your own!

744 Helmsdale Way, South Chesapeake

$635,000
4 Beds 2 Baths 10641777 MLS
Welcome home to this charming 4-bedroom, 2-bath brick ranch nestled on 4.22 wooded acres at the end of a quiet cul-de-sac. Inside, you'll find a warm and inviting layout featuring a family room with a wood-burning fireplace, formal living and dining rooms, granite countertops, and beautifully updated primary and hall bathrooms. Step outside to relax on the new composite deck (2024), gather around the fire pit, or enjoy the peaceful wooded surroundings. The property also includes a detached 2-car garage with a finished studio apartment and full bath, plus a whole-house generator and water softener for added convenience. Offering space, privacy, and versatile living, this property is ready to welcome you home! You won't want to miss this one!

1345 Oak Ridge Drive, 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.