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$755,000
5 Beds 3.2 Baths 10642808 MLS
A Full Acre of Land in the Heart of Southern Chesapeake.... Two Primary Suites. Room for Everyone! Over 3,600 sf. Renovated 5-bedroom home on a beautiful piece of land in Chesapeake — brand new carpet, all freshly painted. The space, privacy, and flexibility that rarely come together at this price point. Two primary suites, one up and one down, give you real options: multigenerational living, long-term guests, or a main-level owner's retreat. The downstairs in-law suite/owners suite has its own private entrance — space for older parents, adult kids, or a home business with client access that never touches your living space. The renovated kitchen features stainless steel appliances and opens to living areas built for gathering. The upstairs primary offers double sinks and a large walk-in closet. A mudroom with half bath handles the daily traffic so the rest of the house stays put together. Outside is where this property separates itself. A wrap-around deck surrounds the above-ground pool — your built-in venue for summer weekends. The roundabout driveway and attached 2-car garage mean parking is never a problem, whether it's a cookout for twenty or just everyday life. And the full acre gives you room to add, expand, or simply breathe — no neighbors ten feet from your window. Homes with this much land, this much flexibility, don't sit long in Chesapeake. Schedule your showing today. Sellers are motivated. Some images are digitally staged.

1833 Benefit Road, South Chesapeake

$1,750,000
4 Beds 4 Baths 10642797 MLS
Set at the end of a quiet Hunters Ridge cul-de-sac, this custom brick estate rests on three private, gated acres, held by a single owner since its 2006 build. Beyond its 5,707 square feet of main finished living space, the home offers approximately 1,800 additional square feet of year-round conditioned space. A two-story foyer with a curved staircase opens to formal rooms and a two-story great room with a see-through gas fireplace. The island kitchen features granite, stainless, and a wet bar. The primary suite is a private retreat with a tray ceiling and a spa bath with a soaking tub. A temperature-controlled pool room, a rarity in Hunters Ridge, holds a heated pool beneath vaulted, skylit ceilings for year-round swimming and entertaining. A detached guest suite of about 715 finished square feet adds a kitchenette and full bath, ideal for extended family or long-term guests. A three-car garage, brick-pillar drive, pergola with hot tub, and patios complete the grounds.

2505 Sylvia Court, 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

$240,000
2 Beds 2 Baths 10642730 MLS
Welcome to 700 New River Court #C, a refreshed Chesapeake condo offering comfort, style, and low-maintenance living in a convenient Greenbrier-area location. Step inside to bright neutral finishes, updated wood-look flooring, and an inviting layout.The spacious living room features natural light, a cozy fireplace with a bold black mantle, and room to relax or entertain. The dining area offers glass doors leading to a private fenced patio, perfect for morning coffee or quiet outdoor enjoyment. A breakfast bar connects to the kitchen, featuring white cabinetry, black hardware, subway tile backsplash, generous counter space, and a galley layout.Upstairs, the bedrooms feel bright and peaceful with soft neutral colors and great natural light. The primary bedroom offers direct access to the vanity area, while the additional bedroom is ideal for guests, an office, nursery, or hobby space. Convenient to Greenbrier shopping, dining, parks, medical facilities, and major commuter routes!

700 New River Court Unit C, 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

$370,000
4 Beds 2.1 Baths 10642424 MLS
Welcome to this exceptional end-unit luxury townhome, original owner bought as the community's model home. Built in 2014 and thoughtfully upgraded throughout, Thomason Trail offers nearly 1,900 square feet of living space, combining timeless finishes with everyday comfort. You'll appreciate the warmth of rich hardwood flooring, abundant natural light, and the attention to detail that sets this home apart. The kitchen is designed to impress, featuring granite countertops, ample cabinetry, a pantry and an open layout that flows seamlessly into the main living and dining areas. All of the mechanicals have been recently updated to include hot water heater 2026. Ceiling fans in every room plus custom wood blinds provide both style, privacy and comfort. One of the home's most distinctive features is the versatile loft, complete with custom built in shelves. Minutes from Greenbrier for shopping and restaurants you won't want to miss this opportunity.

1601 Thomason Trail, South Chesapeake

$614,900
6 Beds 4.1 Baths 10642445 MLS
Rare opportunity to own a beautifully updated 6-bedroom, 4.5-bath home featuring a private, fully equipped in-law suite for multigenerational living, extended family, guests, rental income, or a private home office. The main residence offers 5 spacious bedrooms, 3 full baths, and a stunning remodeled kitchen with quartz countertops, sleek high-gloss cabinetry, stainless steel appliances, and space for a large center island. The separate in-law suite lives like its own home, complete with an open loft-style bedroom, 1.5 baths, walk-in closet, full-size laundry, upgraded kitchen with quartz counters and stainless appliances, and generous living space. Recent upgrades include renovated baths, new windows, patio doors, and Nest thermostats. Step outside to your backyard oasis featuring an 8-foot in-ground pool with newer liner, filter, and pump, plus a built-in deck bar ideal for entertaining. Conveniently located near shopping, dining, schools, military bases, beaches, and major commuter routes.

501 Thornloe Ln Lane, South Chesapeake

$619,900
4 Beds 2.1 Baths 10641071 MLS
Welcome home to this stunning like new construction in the highly sought-after Great Bridge School District! Move-in ready and thoughtfully designed, this beautiful home offers the freedom of no HOA and all the modern finishes today's buyers are looking for.Step inside to discover a bright, open-concept floor plan perfect for both everyday living and entertaining. The spacious first-floor office provides an ideal work-from-home space or flex room to fit your lifestyle. The gourmet kitchen is sure to impress with elegant quartz countertops, a classic subway tile backsplash, white shaker cabinetry, and a full stainless steel appliance package.Throughout the home, crown molding adds a touch of sophistication, while the energy-efficient tankless water heater provides modern convenience. Retreat outdoors to enjoy the fully fenced backyard, perfect for pets, play, or relaxing evenings. Make this home yours today.

1229 Waters Road, South Chesapeake

$635,000
4 Beds 2.1 Baths 10641989 MLS
Welcome to the popular Wells Model in Hickory Manor, offering 4 bedrooms, 2.5 baths, and a versatile upstairs loft. This home features exceptional storage throughout, including a double-door pantry, hall closet, under-stair storage, two upstairs linen closets, and dual closets in the spacious primary suite. The oversized 8-foot-long island has quartz countertops, perfect for entertaining and everyday living. 9-foot ceilings throughout bring in abundant natural light, with unobstructed southern and western exposures. Upstairs, the primary suite offers double closets, dual vanities, a soaking tub, and a separate shower. Three additional bedrooms, a full bath, and a conveniently located laundry room complete the second floor. Additional features include a 50-amp outlet in the garage, ideal for EV charging. Hickory Manor is conveniently located near Edinburgh shopping in top-rated Hickory school district and provides neighborhood pool, clubhouse, fitness center, park, and lawn maintenance.

445 Middleton Way, South Chesapeake

$995,000
4 Beds 3.1 Baths 10641759 MLS
Experience the a blend of luxury, space, and country charm in this stunning 2026 new construction home situated on a picturesque 3-acre lot where horses are welcome. Offering approximately 2,957 square feet of thoughtfully designed living space, this two-story home features 4 spacious bedrooms, 3.5 baths, and an open-concept floor plan great for both everyday living and entertaining. Step inside through the impressive entry foyer and discover 9-foot ceilings on both the first and second floors, smooth drywall finishes, craftsman trim, and quality finishes throughout. The heart of the home is the expansive kitchen featuring granite countertops, a large center island, walk-in pantry complete with cabinetry and countertop workspace, breakfast nook, and seamless flow into the spacious family room with an inviting electric fireplace. A dining room, private office, and convenient mudroom provide additional flexibility for today's lifestyle. The luxurious first-floor primary suite offers generous walk-in closets and a spa-inspired bath with a double vanity, tile flooring, tiled shower, and linen closet. Upstairs, you'll find three oversized bedrooms, each with walk-in closets. The front bedroom includes its own private bath, while the two rear bedrooms share a convenient Jack-and-Jill bath. A spacious loft/game room with durable LVP flooring creates a space for recreation, media, or a second living area. Built for comfort and efficiency, this home includes an elevated slab foundation, premium vinyl lap siding, architectural shingle roof, attached two-car garage, dual-zone HVAC systems, a high-efficiency 50-gallon heat pump water heater, conventional septic system, and pre-wiring for Ethernet and Wi-Fi. Relax on the front or rear concrete porches while enjoying peaceful country views, all while being just minutes from shopping, dining, and everyday conveniences. This exceptional property offers the best of both worlds—modern amenities, quality craftsmanship, and the freedom of country living on your own 3-acre retreat.

1630 Taft Road, South Chesapeake

$549,500
3 Beds 2 Baths 10642197 MLS
Calling all homesteaders! Looking for space to work, build, or spread out in the Grassfield school district? This 5-acre Chesapeake property is built for it. The 720 sq. ft. detached garage runs on full electric — great for a contractor, tradesman, hobbyist, or anyone needing a real workshop, equipment storage, or room for the toys. Easy road frontage means simple access for trucks, trailers, and equipment. The move-in-ready 3-bed, 2-bath home means no work waiting on you: 2023 heat pump, 2024 whole-house professional paint, and new 2025 carpet. Inside you'll find an open kitchen with wood cabinets and breakfast nook, a spacious sunroom, and a large mudroom. Outside: fenced backyard, mature fruit and fig trees, and wildlife right off the Dismal Swamp Canal Trail. minutes from Deep Creek Park. Rare acreage, real workspace, and a home that's ready now. Seller facing unexpected military move. Highly motivated seller. Recently sold comparable properties have sold for $645k. Contact an agent today for a private showig!

317 George Washington Highway S, South Chesapeake

$599,999
4 Beds 2.1 Baths 10641744 MLS
Welcome home to this beautifully maintained 4-bedroom, 2.5-bath home nestled on a quiet cul-de-sac in the sought-after Etheridge Lakes community and within the sought-after Hickory School District. Set on .36 acres, this nearly 2,900 sq. ft. home offers a superb blend of comfort and functionality. Gather around the cozy gas fireplace in the family room, framed by custom built-in bookcases, or enjoy morning coffee in the bright breakfast nook overlooking the backyard. Host holidays in the formal dining room, creating memories for years to come. The spacious FROG serves as the fourth bedroom and offers endless possibilities as a guest suite, playroom, or home office. With generous living spaces, a welcoming floor plan, and a wonderful location, this is a place where every chapter of your story can unfold.

700 Sarasota Arch, South Chesapeake

$449,000
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

$543,740
2 Beds 3 Baths 10641942 MLS
The Asheville, one of our quad-style homes, features two bedrooms, a large bonus room and 3 full baths. Refreshing and cottage-like, The Asheville is single level living at its finest. A welcoming covered front porch leads you to a spacious living room with fireplace. At the heart of the home, the Kitchen is within reach of the dining room, pantry, laundry room, and access to the two-car garage. The Kitchen is accented with Shaker style cabinets, quartz countertops, tile backsplash, and stainless-steel appliances. The primary bedroom with ensuite offers a spacious walk-in closet, tiled shower with glass enclosure, counter-height vanity with double sinks and a separate water closet. For guests or an office, you’ll find a secondary bedroom with an adjacent full bath. Incentives with use of preferred lender! Photos and renderings are from builder's library, actual finishes and features may vary. Photos and renderings are from builder's library, actual finishes and features may vary.

2162 Edwin Drive, South Chesapeake

$539,000
3 Beds 2.1 Baths 10641886 MLS
Welcome home to this beautifully appointed, move-in ready Seafield model in Eagle Pointe, Chesapeake's premier 55+ resort-style community. The gourmet eat-in kitchen features granite countertops, stainless steel appliances, gas range, breakfast bar, & butler's pantry plumbed for a sink. Enjoy both casual & formal entertaining with an eat-in kitchen & elegant formal dining room. Relax year-round in the bright Florida room w/custom doors. Plantation shutters & custom window treatments enhance the home's timeless appeal. The first-floor primary suite offers a spacious walk-in closet & spa-inspired bath w/split vanities & walk-in shower. Upstairs features a loft overlooking the family room, two bedrooms, full bath, & walk-in storage/mechanical room. Patio w/electric awning, gas grill line, certified green construction, spray foam insulation, & Rinnai tankless water heater. Enjoy The Bay Club's indoor/outdoor pools, fitness center, ballroom, library, billiards, game rooms, and more!

1517 Eagle Glen Drive, South Chesapeake

$349,900
4 Beds 2.1 Baths 10641818 MLS
Welcome to this spacious two-story home offering a fantastic layout and incredible potential! The first floor features a formal living room, separate dining room, a cozy den, and a convenient half bath. Upstairs, you will find three comfortably sized bedrooms alongside a primary suite complete with its own private en suite bath. Excellent storage and parking are provided by the attached two-car garage. Situated in a prime location just minutes from shopping, local dining, entertainment, major interstates, and area bases. This property is a wonderful opportunity to bring a little elbow grease, add your personal touches, and truly make it your own. Call today to schedule your private showing! Some virtual staging utilized in pictures.

844 Parapet Road, 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

$309,000
3 Beds 2 Baths 10641791 MLS
Renovated condo in private waterfront community in the heart of Great Bridge! This beautiful 3BR/2BA condo boasts an open floor plan great for entertaining. New LVP floors, carpet, tiled bathrooms, quartz countertops throughout, appliances, fixtures, paint & more ALL just in 2023. New HVAC 2025 .Enjoy a lifestyle with such amenities as ,communal fire pit and grilling area, outdoor pool, clubhouse, gazebo, kayak storage, docks, elevator, building exterior, water, sewer, trash pickup, grounds, master insurance policy, storage & 2 dedicated parking. Sale includes a deeded boat slip #5 in protected private harbor on the Intercostal Waterway that you can view from your unit and balcony! Call today for your private showing.

4 Harbor Watch Drive Unit 508, South Chesapeake

$595,000
5 Beds 2.1 Baths 10641782 MLS
Welcome to the Shenandoah at Retreat at Edinburgh, a sought-after 55+ community where low maintenance living meets modern comfort. This beautifully designed home features an open-concept floor plan, a gourmet kitchen with quartz countertops, stainless steel appliances, and a large island looking over the dining and living rooms, making it perfect for entertaining. On the first floor, you will conveniently find a home office and a primary suite that offers a private retreat with a spa-inspired shower, vanity, and large walk-in closet. Upstairs, you'll find three large additional bedrooms and a loft ideal for guests, hobbies, or a home office. Community amenities include a resort style pool, clubhouse, fitness center, dog park, walking paths and more. Conveniently located near shopping, restaurants, and medical facilities, this community offers the perfect blend of convenience and carefree living.

2000 Barton Lane, 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.