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$250,000
3 Beds 1 Baths 10642992 MLS
Charming ranch nestled on a spacious lot in Chesapeake! This 3 bedroom, 1 bath home offers a warm and inviting layout that’s ready for you to make your own. Enjoy the convenience of a detached two-car garage, plenty of driveway parking, and a large yard with endless possibilities for entertaining, gardening, or simply relaxing. There’s even room to park your boat, RV, trailer, or recreational toys! Whether you’re a first-time homebuyer, downsizing, or looking for a property with space to spread out, this home offers the perfect blend of comfort, functionality, and outdoor living. Conveniently located with easy access to shopping, dining, schools, and major highways, this is one you won’t want to miss! * Some photos are virtually enhanced or staged*

2420 Payne Road, South Chesapeake

$615,000
3 Beds 3 Baths 10643157 MLS
This beautifully updated brick home combines comfort, functionality, and style with flexible spaces designed for modern living. At the heart of the home, the stunning kitchen features a custom island perfect for gathering, entertaining, and everyday life. Spacious bedrooms, versatile living areas, and an expansive sunroom provide plenty of room to spread out, with ideal spaces for a home office, virtual learning, hobbies, or creative pursuits. A true standout feature is the oversized two-car garage/workshop, complete with a full bath and approximately 780 square feet of unfinished space above—offering endless possibilities for guest accommodations, a studio, home gym, office, or additional storage. Step outside to enjoy beautifully landscaped grounds, custom decking, and an inviting patio designed for entertaining. A charming custom she-shed adds even more versatility, along with an additional flex space inside the home. Thoughtful updates throughout and adaptable spaces are a win!

103 Ashley Road, South Chesapeake

$729,000
4 Beds 2.1 Baths 10643077 MLS
Sitting on just under 1 ACRE escape to your own private retreat in the heart of Hickory! Nestled on a peaceful wooded setting, this beautifully maintained home offers the perfect blend of space, comfort and modern updates. Inside, you'll find souring ceilings, abundant natural light, and inviting living spaces designed for both relaxing and entertaining. Enjoy the tranquility of country style living while still being conveniently located near shopping, dining, and sought after schools. Major system updates provide peace of mind including updated heat pump, septic improvements, well and water filtration updates, gutter systems enhancements, oversized shed, extended driveway offering ample space for boat or RV storage, and a generator hookup. This property combines rural charm with everyday practicality. Whether you're hosting guests, enjoying quiet mornings outdoors, or simply looking for more privacy and space, this property offers a rare opportunity to enjoy the best of Chesapeake.

1740 Land Of Promise Rd Road, South Chesapeake

$949,608
4 Beds 3.1 Baths 10643106 MLS
Welcome to the Kentland by Kirbor Homes; where your Pinterest board finally gets to come to life! Designed for the way you really live, this home offers the perfect blend of style, comfort, and flexibility. With a luxurious first-floor primary suite, spacious open-concept living, and room to spread out upstairs, there's a place for everyone (and everything). The chef-inspired kitchen is ready for everything from holiday feasts to takeout nights, featuring our upgraded Chef's Appliance Package, a large center island, and plenty of space to gather. The great room is designed for game nights, movie marathons, or simply relaxing after a long day. Located in the sought-after Sanderson Estates, you'll enjoy spacious homesites, beautiful surroundings, and the quality craftsmanship Kirbor Homes is known for. Whether you're entertaining friends, hosting family, or just enjoying a quiet morning coffee on the porch, the Kentland is ready to fit your lifestyle. Come see why your next chapter deserves a home this fun to live in! Contact Listing Agent to schedule a tour or appointmnet at our design center today! Builder contract. Ask about Lender incentives!

1516 Cedarville Court, South Chesapeake

$479,000
4 Beds 2 Baths 10642873 MLS
Tucked away on a quiet wooded cul-de-sac in Brandermill, this quality-built 4-bedroom, 2-bath home blends timeless charm with modern updates. New Architectural roof, new beautifully renovated bathrooms, new kitchen countertops, newer LVP flooring. Centrally located dining area creates the warm, functional heart of the home. A spacious sun-filled addition with cathedral ceiling opens to the perfect patio gathering area for cookouts and a large backyard made for entertaining, yard games and having fun with family and friends. Unwind on the spacious shaded front porch and soak in the peaceful surroundings. This home has been thoughtfully maintained, a genuine gem offering comfort, character and is convenient to schools, shopping, dining and everyday essentials. Sparkling with style and ready to welcome you home!

804 Greenspring Court, South Chesapeake

$540,000
4 Beds 2 Baths 10642998 MLS
Welcome to 233 Downing Drive, where everyday living feels easy, comfortable, and connected. Set in Chesapeake’s Tunbridge Station, this 4-bedroom, 2-bath home offers approximately 2,046 square feet with an open floor plan designed for gathering, relaxing, and enjoying time at home. Start your mornings in the bright all-season room, host dinner with room to spread out, then step outside to your own backyard retreat. The above-ground pool is surrounded by Trex decking, creating the perfect setting for summer afternoons, weekend cookouts, and unwinding with friends. When the day slows down, the hot tub conveys and is ready for quiet evenings under the stars. The detached workshop with power gives you space for projects, storage, hobbies, or tools. Inside, enjoy a first-floor bedroom and full bath, updated kitchen, refreshed baths, walk-in attic, pantry, and flexible spaces. With a fenced backyard, attached 2-car garage, and thoughtful updates, this home is ready for its next chapter.

233 Downing Drive, South Chesapeake

$999,985
6 Beds 4 Baths 10642034 MLS
This gorgeous home can be your "White-House"!! Step into this ALL-White brick 2-story contemporary home with front porch, arches and large foyer, and be ready to fall in love! The backyard is a private oasis with trees, pond and flowing fountain. Enjoy the serenity of nature, including the blue herons, egrets, ducks and more, as you sip your morning coffee or have dinner on the patio. As you enter the first-floor foyer, notice the large formal dining room on the left that is perfect for entertainment, an archway to the 2 first-floor bedrooms (one currently being used as an office), full bath with shower and another archway to the large familyroom with gas fireplace. You will be excited by the huge open kitchen with granite counters, an oversized island, eat-in area and pantry. Also, on the first level is an archway inset that holds the Stiltz-Lift (elevator). Either take the wooden stairs with wrought-iron railings or the Stiltz to the 2nd level. Upstairs are the Primary bedroom with extra-large walk-in closet and an incredible ensuite bath, complete with 2 sinks, large, deep soaking tub, 5 x 4 ft shower with rainfall head and sit-down area. The primary bedroom has a gas fireplace and a wall of glass windows and french doors that lead to the Juliet balcony. A separate laundry room, three other bedrooms and 2 full bathrooms provide the space for family and friends to come and visit. BUT, there's more to complete the 2nd floor. Check-out the theater/game room (great for entertainment) and additional wrought-iron railings that overlook the stairs, foyer area and lead to the Stiltz lift doorway. The extra-large 3-car garage has enough room for your cars or anything else. BUT there's more!! YES, then there's the backyard oasis! Well, you'll just have to see it for yourself. This home is convenient to shops, restaurants, malls, stores, Greenbrier Country club, banks, parks, interstate, university and so much more!

1324 Simon Drive, South Chesapeake

$580,000
4 Beds 3 Baths 10642916 MLS
Retreat to the expansive second-level primary suite, featuring a private sunroom, spacious loft, luxurious garden tub, separate tiled shower, and beautiful cherry hardwood flooring. The main level offers three additional bedrooms, two full bathrooms, and a generous sunroom complete with a built-in bar—perfect for entertaining or relaxing. Enjoy 3.16 acres of peaceful outdoor living, featuring a barn, chicken coop, and storage shed, offering endless possibilities for hobbies, animals, or gardening. Major updates provide peace of mind, including a new roof (2017), two-zone HVAC system (2020), and water heater (2023). Fresh interior paint throughout and brand-new downstairs carpet make this home truly move-in ready. Welcome Home!

2600 Saint Brides Road W, South Chesapeake

$300,000
3 Beds 2.1 Baths 10642912 MLS
Welcome to this beautifully maintained end unit townhome nestled in a small, quaint neighborhood that offers both charm and convenience. Enjoy direct access to Oak Grove Lake Park from a fenced connected walking trail. Make sit easy to take scenic strolls, exercise, or spend time outdoors. Perfectly located with quick access to the interstate, this home is ideal for commuters while still providing a peaceful place to unwind. Inside and out you will appreciate the spacious yard, built-in storage shed, well maintained HVAC system, roof (2018), and fresh carpet and paint (2021). With thoughtful updates, extra privacy as an end unit, and and unbeatable blend of comfort, convenience, and outdoor access this move in ready home is one you wont want to miss.

744 Hunters Quay Quay, South Chesapeake

$499,900
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

$230,000
2 Beds 2 Baths 10642377 MLS
Bright and inviting, this well-maintained 2-bedroom, 2-bath condo is located in the desirable Willow Point community. A welcoming first-floor foyer with soaring cathedral ceilings leads upstairs to an open, airy living space featuring beautiful oak hardwood floors. Step outside to your private balcony overlooking the community pool - the perfect spot to enjoy your morning coffee or unwind at the end of the day. Ideally situated just minutes from major highways, shopping, dining, military bases, and more, this low-maintenance community also includes pool access, landscaping, and exterior maintenance. Offering the perfect blend of comfort, style, and convenience, this home is ready to welcome its next owner!

1214 Loose Strife Place, South Chesapeake

$309,000
3 Beds 2.1 Baths 10642451 MLS
Welcome home to this charming and spacious interior townhome, perfectly located in the heart of everything! Offering nearly 1,600 sq ft of well-maintained living space, this home has 3 spacious sized bedrooms & 2.5 baths, providing the perfect blend of comfort and functionality. Filled with character and warmth, the thoughtfully designed floor plan offers plenty of room to relax and entertain. Step outside to enjoy the private backyard an ideal space for morning coffee or weekend entertaining! Conveniently located just minutes from the interstate, shopping, restaurants, and everyday amenities, you'll love the ease of living this central location provides. With ample parking and a welcoming neighborhood feel, this home truly has it all.

1404 River Birch Run, South Chesapeake

$755,000
5 Beds 3.2 Baths 10642808 MLS
A Full Acre. Two Primary Suites. Room for Everyone — 1833 Benefit Rd, Chesapeake VA. Over 3,600 sf. Motivated sellers! Renovated 5-bedroom home on a full acre 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 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.

1833 Benefit Road, South Chesapeake

$550,000
4 Beds 2 Baths 10642398 MLS
Welcome to 529 Royal Grant Drive in the desirable Cheshire Meadows area of Chesapeake. This well-maintained 4-bedroom, 2-bath ranch offers approximately 2,064 square feet of living space with a comfortable layout, office/study, finished room over the garage, and attached 2-car garage. The updated kitchen features granite countertops and stainless appliances, along with cathedral ceilings, skylights, a wood-burning fireplace, updated bath tile and fixtures, new interior paint, updated exterior vinyl trim, new exterior doors, and a new garage door and opener. The backyard is perfect for relaxing or entertaining with a deck, patio, privacy fence, storage shed, and salt system in-ground pool with new liner. Conveniently located near Great Bridge schools, shopping, restaurants, and commuter routes. A wonderful opportunity in a sought-after Chesapeake location. Listed at $550,000.

529 Royal Grant Drive, South Chesapeake

$459,900
3 Beds 2 Baths 10642749 MLS
Welcome to this lovingly maintained, one-owner ranch-style home nestled on 3 private acres. This well-built residence has been meticulously cared for and is ready for its next chapter — offering the perfect canvas for cosmetic updates to make it entirely your own. The open, manageable layout is ideal for those seeking single-level living with room to breathe. A standout feature is the oversized detached 2-car garage/workshop, perfect for hobbyists, car enthusiasts, or anyone needing serious storage and workspace. The expansive acreage provides privacy and tranquility rarely found at this price point, with mature surroundings that create a true retreat from the everyday. Whether you are looking to personalize a solidly built home or simply enjoy the peace and space this property offers, the opportunity here is undeniable. Priced to reflect its cosmetic potential while honoring the exceptional care this home has received throughout its single ownership.

3600 Martin Johnson Road Unit RD, South Chesapeake

$365,000
3 Beds 2.1 Baths 10642611 MLS
Beautiful and meticulously cared for open concept, end unit condo located on a quiet cul-de-sac. Rare private wooded view from both the backyard and primary ensuite. Custom upgrades include a shiplap fireplace accent wall with elegant wood mantle, luxury vinyl plank floors, modern light fixtures, and an entryway accent wall with mounted hooks. Looks like a model home, recently painted and features tons of natural light. The kitchen has gorgeous 42" wood cabinets, granite counters, an island, SS appliances, 2 pantries, and bar seating, perfect for entertaining. Primary ensuite retreat features a beautiful wooded outside view, tray ceiling, 2 walk-in closets, dual sinks, and custom wood shelving with shiplap accent wall. Ceiling fans throughout. Convenient upstairs laundry. 2 car garage, vinyl fence, and private side entrance. This home has it all! Conveniently located for easy access to interstates, shopping, and entertainment. Fees include front yard landscaping and insurance policies.

706 Albertine Court, 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

$534,900
5 Beds 2.1 Baths 10642746 MLS
Welcome home to lakefront living in sought-after Bryant Farms! From cozy nights by the custom gas fireplace to lazy mornings soaking in peaceful water views. The open-concept family room and kitchen create the perfect heart-of-the-home feel, while formal living and dining rooms offer beautiful hardwood and tile floors for those special gatherings. Chefs will love the eat-in kitchen, featuring a center island, granite countertops, a full pantry, and stainless steel appliances including a Frigidaire Gallery gas range and fridge. Step outside to the screened porch — your new favorite spot for morning coffee or unwinding after a long day. Upstairs, retreat to a spacious primary suite with a walk-in closet, double vanity, soaking tub, and separate shower. Three additional bedrooms, including a generous FROG, offer flexible space for family, guests, or a home office, and full guest bath.

2428 Annie Circle, 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

$335,000
3 Beds 2.1 Baths 10642721 MLS
Welcome to this beautifully maintained condo featuring two spacious primary suites, each complete with a private ensuite bathroom, generous walk-in closet, and additional sitting area for added comfort and flexibility. The open-concept floor plan is great for everyday living and entertaining, highlighted by an updated kitchen with stainless steel appliances, modern cabinetry, and durable LVP flooring throughout the main level. A versatile first-floor bonus room offers the perfect opportunity for a third bedroom, home office, or flex space to suit your needs. Upstairs, you'll find the convenience of a dedicated laundry room along with brand-new carpet installed on the stairs and throughout the second level. Residents enjoy access to a community pool and clubhouse, while the HOA provides exceptional value by covering water, sewer, and trash pickup. Offering comfort, convenience, and low-maintenance living, this move-in ready home is one you won't want to miss.

1513 Braishfield Court, South Chesapeake

$425,000
4 Beds 2 Baths 10642702 MLS
Pride of ownership shines throughout this beautifully maintained 4-bedroom, 2-bath ranch nestled on a corner lot in the desirable Clearfield community. From the moment you arrive, you'll be welcomed by impeccable curb appeal, lush landscaping, and vibrant flower beds that create a beautiful first impression. Inside, you'll find over 2,100 square feet of comfortable living space featuring a cathedral ceiling, a cozy gas fireplace, a spacious primary suite with a private bath, and a finished room over the garage that offers endless possibilities as a home office, playroom, or flex space. Relax on the covered rear deck, enjoy the privacy-fenced backyard, and appreciate the convenience of the attached 2-car garage. No HOA! Conveniently located near shopping, dining, schools, and major commuter routes. This lovingly cared-for home is ready to welcome its next owners.

500 N Hills 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.