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$490,000
4 Beds 2.1 Baths 10642834 MLS
This home is a Wellspring gem with valuable upgrades. The front lawn and spacious 2 car garage create a warm and inviting first impression. Inside, the thoughtfully designed first floor offers multiple living spaces including a formal living room, dining room, eat in kitchen and cozy den featuring a gas fireplace. A convenient half bath makes everyday living and entertaining a breeze. Upstairs has four generously sized bedrooms including a primary suite with vaulted ceilings. Throughout the home, you'll appreciate having no carpet and LVP in every bedroom. The deck right outside the patio door is superb for hosting, overlooking an expansive newly fenced backyard with endless possibilities for play, gardening, pets or outdoor gatherings. A storage shed provides additional space for tools and equipment. TESLA EV charger conveys. Loan is assumable.

405 S Monterey Drive, South Chesapeake

$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

$400,000
4 Beds 2 Baths 10642623 MLS
Welcome to 700 Cardover Avenue, where timeless character meets modern luxury in this beautifully fully renovated Chesapeake home. Offering 4 spacious bedrooms, 2 full baths, and approximately 1,900 square feet of thoughtfully reimagined living space, this stunning property blends classic charm with today’s most desirable finishes and functionality. Originally built in 1958, this home has been completely transformed to deliver a move-in-ready experience while preserving the quality craftsmanship and character buyers appreciate. From the moment you step inside, you’ll be welcomed by bright, airy living spaces filled with natural light and a warm, inviting atmosphere. The thoughtfully designed floor plan offers exceptional versatility with generous living areas and spacious bedrooms, creating the perfect balance of comfort and function. Whether hosting gatherings, enjoying quiet evenings at home, or creating flexible work-from-home space, this home adapts beautifully to your lifestyle. At the heart of the home, the seamless flow between living spaces creates an effortless environment for everyday living and entertaining. Every detail has been carefully curated to offer elevated style with modern convenience. Step outside to your private outdoor retreat featuring a brand-new backyard deck, suitable for morning coffee, weekend barbecues, evening gatherings, or simply unwinding outdoors. The deck creates an ideal extension of the home, inviting you to enjoy indoor-outdoor living year-round. Adding even more value and versatility, the detached garage offers excellent storage, workshop potential, hobby space, or additional parking—an increasingly desirable feature for today’s buyers. Conveniently located near shopping, dining, parks, schools, major commuter routes, and all that Chesapeake has to offer, this beautifully renovated home combines modern updates, functional living, and timeless appeal. This is more than just a renovation—it’s a fresh new chapter waiting to be written. Don’t miss your opportunity to make it yours.

700 Cardover Avenue, Central 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

$369,800
5 Beds 2 Baths 10642460 MLS
Discover one of the best values in Chesapeake! This spacious 5-bedroom, 2-bath home offers over 2,100 square feet of versatile living space with room for everyone. Recent updates include a newer roof, updated HVAC, replacement windows, luxury vinyl plank flooring, fresh paint, and updated lighting, providing peace of mind and modern appeal. The bright kitchen features ample cabinet and counter space, while the open living and dining areas are perfect for everyday living or entertaining. The flexible floor plan includes generously sized bedrooms, making it ideal for a growing family, multi-generational living, or those needing dedicated home office space. Outside, enjoy a large fenced backyard with plenty of room for pets, gardening, play, or future outdoor entertaining. Conveniently located near shopping, dining, military bases, major interstates, parks, and schools, this home offers an easy commute throughout Hampton Roads. With five true bedrooms, substantial square footage, and numerous updates, this home delivers exceptional value compared to other homes in its price range. Whether you're a first-time buyer looking for extra space or an investor seeking a strong opportunity, this property is ready for its next owner. Don't miss your chance to own one of Chesapeake's best buys—schedule your private showing today!

4205 Nautilus Avenue, Central Chesapeake

$554,500
4 Beds 3.1 Baths 10642380 MLS
Welcome to Miars Farm in sought-after Western Branch! This beautifully maintained 4BR, 3.5BA home offers ~2,500 sq ft of inviting living space on a .25-acre lot with timeless curb appeal and modern farmhouse touches. Enjoy a classic front porch, spacious driveway, and attached garage. Inside, the open layout features a stunning eat-in kitchen with granite countertops, stainless steel appliances, gas cooking, an island seating area, and a sunny breakfast area overlooking the backyard. The family room shines with exposed beams and a cozy fireplace. The vaulted primary suite features a spa-like bath with a soaking tub and a tiled shower. A large FROG/bonus room with a full bath adds flexibility. Step outside to your private fenced yard with a deck, above-ground pool, and storage/workshop shed with electricity. Convenient to schools, shopping, and commuting—this home truly has it all!

3421 Anita Circle, West 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

$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

$525,000
5 Beds 3.1 Baths 10641817 MLS
Tucked away on a quiet end street shared by only three other homes, this brand new construction offers a rare sense of privacy while still being close to everything Western Branch has to offer. With minimal traffic and a park-like setting, it’s the kind of place where evenings are quiet, kids can play outside, and home truly feels like a retreat. Inside, this thoughtfully designed 5 bed, 3.5 bath home is built for both comfort and flexibility. The open concept living area flows effortlessly into a spacious, modern kitchen. A 1st floor primary bedroom provides the ease of main level living, while a 2nd floor owner’s suite creates the ideal private escape or multi-generational option. Additional highlights include a two car attached garage, generous bedroom sizes, and beautifully planned finishes throughout all while located within the sought after Western Branch school district. You’re not just purchasing new construction - you’re securing space, privacy, flexibility, and a lifestyle.

5041 Queen Street, 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.