Refine Search
Sort by
$560,000
4 Beds 2.1 Baths 10647434 MLS
Welcome to this beautifully maintained home in Joliff Woods! Offering approx 2,400 square feet of living space, this spacious 4-bedroom, 2.5-bath residence combines comfort, style, and functionality. Step inside to a beautiful two-story foyer filled with natural light, creating a bright and inviting first impression. The main level features engineered hardwood flooring, a well-appointed kitchen with stainless steel appliances, and a spacious family room highlighted by a cozy gas fireplace and custom built-in cabinetry—perfect for everyday living and entertaining. Situated on a generous 0.63-acre lot, the backyard is an entertainer's dream, featuring a large new deck with in-ground pool and expansive yard, providing the ideal setting for summer gatherings, outdoor dining, or simply relaxing in your own private retreat. Upstairs, you'll find four generously sized bedrooms with abundant closet space. The impressive primary suite offers a walk-in closet ,a spa-inspired ensuite bath with a jetted soaking tub, separate walk-in shower, and plenty of room to unwind. Additional features include ceiling fans throughout, elegant dining room light fixtures, and ample storage. Don't miss this incredible opportunity to make it yours!

4936 Oriole Drive, Chesapeake

$839,500
5 Beds 3 Baths 10647712 MLS
New Home by Custom Builder in Martin’s Point (Western Branch) main floor living, 4 or 5 bedroom plan. First floor primary bedroom with luxury bath- zero entry tiled shower & free standing tub, Open floor plan with Huge Gourmet Kitchen w/ Quartz counter tops, 36” gas cooktop with built-in microwave/oven, Cathedral Ceiling Family Room w/ Beamed ceiling, amazing stone fireplace with built-in bookcases, expansive covered porch (29’x10’) overlooks a privately wooded backyard & scenic view .42 acre. 3 Bedrooms & Study with French doors on 1st floor with 2 add'l large rooms on the second floor, 3 baths. Excellent location, easy access to I-664, near schools, shopping, Custom Builder is a member of Southern Living Custom Home Builder Program (since 1993). Superior quality features include Trane HVAC system, tankless hot water heater, custom cabinetry, large utility room/drop zone, Hardie Plank exterior, quality upgrades throughout. Fully sodded and irrigated yard.

3909 Bruce Road, Chesapeake

$660,000
4 Beds 2.1 Baths 10647705 MLS
Experience the perfect blend of quality, comfort, and outdoor living at 1928 Rockwood Drive in the highly sought-after Grassfield School District! Originally built by Stephen Alexander Homes, this beautifully maintained home is tucked away in a quiet neighborhood and features a dedicated office/study, second-floor laundry, and a spacious primary suite with soaring cathedral ceilings. The inviting living room showcases a gas fireplace flanked by custom built-ins. Outside, enjoy a private backyard oasis with an in-ground pool and TREX decking, installed in 2020. Additional updates include new windows and doors, installed in 2021. Complete with a two-car attached garage and driveway parking for four vehicles, this home truly has it all!

1928 Rockwood Drive, Chesapeake

$630,000
5 Beds 3 Baths 10647563 MLS
Welcome to 404 Clara Drive, where space, comfort, and style come together! Tucked away on a quiet cul-de-sac, this beautifully maintained home features 5 spacious bedrooms and 3 full bathrooms, providing plenty of room for everyone. Step inside to a dramatic two-story foyer that opens to formal living and dining rooms for entertaining. The eat-in kitchen is designed for both function and style with a center island, 42-inch cabinetry, stainless steel appliances, and ample storage. The inviting family room features a cozy fireplace, while a first-floor bedroom with direct access to a full bath for guests or multi-generational living. Upstairs, the impressive owner's suite offers double tray ceilings, a sitting area, oversized walk-in closet, and a spa-inspired bath with dual vanities, a jetted tub, and separate shower. Enjoy relaxing or entertaining in the large fenced backyard with a spacious deck. This exceptional home is one you won't want to miss!

404 Clara Drive, Chesapeake

$239,911
2 Beds 2 Baths 10647687 MLS
Welcome to this beautifully updated two-story condo in the sought-after Riverwalk community of Chesapeake. Soaring 20-foot vaulted ceilings and gorgeous LVP flooring create a bright, open feel throughout. The updated kitchen features granite countertops, newer appliances, a deep sink, modern fixtures, perfect for everyday living and entertaining. Upstairs, the spacious loft with custom built-ins offers flexible space for a home office, reading nook, or guest retreat. Accessibility enhancements include a motorized stair lift to the second floor conveys with the home, providing added convenience and accessibility. Enjoy your private patio and maintenance-free living with community amenities including a pool, scenic walking trails, and condo fees covering water, sewer, trash, exterior maintenance, and the master insurance policy. Conveniently located near shopping, dining, major interstates, and military bases, this move-in-ready home offers comfort, convenience, and style.

705 Rapidan River Court Unit E, Chesapeake

$449,900
3 Beds 2.1 Baths 10647748 MLS
Rain or shine, the screened porch is calling. This move-in ready end-unit Nansemond floorplan in The Retreat at Western Branch offers low-maintenance living with a first-floor primary suite, 2-car garage, open-concept layout, and abundant natural light. The kitchen features bar seating overlooking the living room with a cozy gas fireplace, plus a spacious walk-in pantry to keep everything organized. Your favorite spot just might be the screened, covered rear porch. Upstairs offers two additional bedrooms, a loft, guest bath, and walk-in attic. Resort-style amenities include a clubhouse, pool, outdoor kitchen, fire pit, billiards, fitness center, community garden, dog park, and beautifully landscaped grounds.

4607 Longleaf Place, Chesapeake

$583,740
4 Beds 2.1 Baths 10647703 MLS
Welcome to the Shenandoah at Retreat at Edinburgh -Chesapeake’s premier 55+ low-maintenance community! Enjoy luxury townhome living with a modern open-concept design, gourmet kitchen with quartz countertops and stainless steel appliances, and a sunlit family room perfect for entertaining. The first-floor primary suite offers a spa-inspired bathroom, featuring a walk-in shower, and oversized walk-in closet, while upstairs features three spacious bedrooms, a loft, and ample storage. Community amenities include a resort-style pool, clubhouse, fitness center, dog park, walking paths, and more. Embrace the ultimate active adult lifestyle near fine dining, shopping, and beautiful parks. Photos and renderings are from builder's library, actual finishes and features may vary.

2009 Barton Lane, Chesapeake

$460,000
4 Beds 2.1 Baths 10647155 MLS
Welcome to this beautifully updated 4-bedroom, 2.5-bath home overlooking the 15th tee of Greenbrier Country Club. Soaring vaulted ceilings, abundant natural light, and an open floor plan create an inviting atmosphere from the moment you enter. The inviting sunken living room adds warmth and character, while the renovated bathrooms offer a fresh, modern feel. The spacious primary suite features a private second-story deck with peaceful golf course views. Enjoy outdoor living on the expansive backyard deck overlooking the fairway. Additional updates include a new backyard fence (2024) and replaced windows and gutters (2022). A 2-car attached garage provides added convenience. Community amenities include a neighborhood pool. Only half a mile from Chesapeake City Park and conveniently located near shopping, dining, parks, major highways, military installations, and all that Greenbrier has to offer. Schedule a tour today!

1005 Woodsmans Reach, Chesapeake

$775,000
5 Beds 3 Baths 10646970 MLS
Welcome to this beautifully updated 5-bedroom, 3-bath brick ranch tucked away on a quiet cul-de-sac in sought-after Emerald Lakes. Offering approximately 3,200 square feet, this home features a bright open-concept design with soaring cathedral ceilings, Brazilian walnut floors, custom trim, wainscoting, wood ceiling beams, and extensive upgrades throughout. The remodeled kitchen boasts quartz countertops, custom range hood, newer appliances, subway tile backsplash, and overlooks the spacious living area with gas fireplace and striking wood accent wall. The first-floor primary suite offers private patio access, a cedar-lined walk-in closet, jetted tub, separate shower, and dual vanities. The finished FROG with full bath is ideal as a guest suite, media room, or fifth bedroom. Additional highlights include a 3-year-old HVAC, 2018 water heater, rebuilt rear stairs (2026), irrigation system, custom landscaping, in-wall surround sound, oversized driveway, no HOA, and a private fenced backyard.

1204 Lingale Court, Chesapeake

$675,000
5 Beds 3 Baths 10646827 MLS
Welcome to Viridian Reserve at Hickory, where comfort, space, and peaceful wooded views come together in one exceptional South Chesapeake home. From the moment you step inside, you'll be greeted by soaring cathedral ceilings, an inviting multi-landing staircase, and a warm, open layout designed for everyday living and entertaining. The spacious family room features a cozy gas fireplace, while the incredible kitchen is truly the heart of the home, offering beautiful wood cabinetry, an abundance of cabinet space, updated appliances, and a convenient wine/beverage refrigerator. The formal dining area provides plenty of room for gatherings, and the first floor also includes a private office, a bedroom, and a full bathroom, great for guests, multigenerational living, or working from home. Upstairs, the oversized primary suite is a true retreat with room for a sitting area, three closets, and a luxurious ensuite bath featuring granite countertops, dual vanities, a walk-in shower, private water closet, and an additional spacious walk-in closet. Outside, enjoy relaxing on the charming covered porch overlooking the large backyard with peaceful wooded views, with the option to easily screen it in for year-round enjoyment. The oversized two-car garage offers exceptional storage, a built-in workbench, and plenty of room for hobbies, while the extended driveway provides additional parking. Located in the highly desirable Hickory area, this home offers the perfect combination of space, functionality, and privacy.

308 Wisdom Path, Chesapeake

$569,900
4 Beds 2.1 Baths 10646819 MLS
Welcome to this beautifully maintained 4 bedroom, 2 and a half bath, all-brick ranch in the Grassfield School District of Chesapeake. This home features updated eat-in kitchen to include granite counter tops, stainless steel appliances (KitchenAid Refrigerator), gas range, shaker cabinets, and fresh paint. Enjoy an open layout with a very spacious great room, vaulted ceilings and a gas fireplace. French doors offer privacy to the formal dining, living room/office. Stunning bamboo floors throughout the kitchen and living areas. The large finished bedroom over the garage offers new LVP flooring, lighting, shelving, built in reading nook or can be used as a bed. Major system upgrades include TRANE HVAC system installed in 2021 with duct work replaced and system zoned in 2025. RainSoft reverse osmosis, enclosed crawl space with dehumidifier, insulated garage doors, updated vents and a newer gas water heater. Half bath located next to the mudroom/laundry room, washer & dryer to convey. New carpet in all main floor bedrooms. Enjoy outdoor living on your covered front porch or in your private fenced in backyard and deck. Expansive attic space for storage and extended driveway for additional parking. A truly move-in-ready Chesapeake home, minutes to shopping, dining, and interstate access. Please ask for the detailed upgrade list of extensive repairs and improvements. The home has been meticulously maintained with major system updates throughout.

817 Doe Run Drive, Chesapeake

$675,000
5 Beds 3 Baths 10646878 MLS
Welcome home to this spacious 5-bed, 3-bath home offering 3,842 sq ft of beautifully designed living space on a generous .84-acre lot. With multiple living areas, a HUGE bonus room over the garage, plus a formal living room, dining room, family room, and bright sunroom, there's plenty of space to spread out. The open kitchen flows seamlessly into the family room and sunroom. Upstairs, the spacious primary suite boasts a spa-like bath with a jetted tub, separate shower, and dual vanities. Brand-new carpet was installed upstairs. Step outside to your private backyard retreat featuring a Trex deck, outdoor kitchen, stamped concrete patio, and an expansive fenced yard with a newer vinyl privacy fence with four gates. A storage shed with power provides plenty of extra storage. Additional highlights include stunning curb appeal, a stamped concrete driveway, epoxy-coated garage floor, EV charger, and easy access to military bases, major highways, shopping, dining, and entertainment.

3204 Hearring Way, Chesapeake

$825,000
5 Beds 2.1 Baths 10646792 MLS
Space to gather, land to enjoy, and a separate apartment for the people who matter most. Nearly 3,900 square feet in the main home, 3 private acres, a detached three-car garage, and an approximately 1,000-square-foot apartment above it. This sprawling ranch offers four first-floor bedrooms, including the spacious primary suite with dual closets, beautifully refinished hardwoods, fresh paint, updated lighting, newer roof, new carpet and an expansive kitchen with gas cooking and newer appliances. A finished bonus room upstairs serves as the fifth bedroom or flexible space for guests, hobbies, or a quiet retreat. An enormous walk-in attic provides rare expansion potential, with room to add finished living space for an even more complete upstairs retreat. Enjoy the new Trex deck and peaceful backyard with room to entertain, garden, play, and bring your horses-picture them grazing outside your kitchen window while your coffee brews. Dreaming of an inground pool and backyard oasis? There is room for that too. Need space for your in-laws? Above the detached garage, the separately metered apartment includes its own bedroom, full bath, kitchen, living area, and laundry, creating true independent space for extended family, guests, a studio, or private home office. The apartment is not counted in sq ft/bedroom/bath count in this listing. Well and septic mean no monthly city water or sewer bill. Located in Riverwood, a quiet acreage community known for spacious homesites, mature trees, room for horses, and a neighborhood boat launch for enjoying nearby waterways. Enjoy the space and privacy of South Chesapeake in the Grassfield school district. Come see the lifestyle you have been searching for.

3700 Riverwood Crescent, Chesapeake

$665,000
4 Beds 3 Baths 10646600 MLS
LUXURY COASTAL RESORT STYLE RIVER FRONT COMMUNITY! Welden Field & Rowe Custom Home on a Premium .44-acre lot backs to Nature Preserve. Resort like lifestyle w/ waterfront Gazebo, deep water access, Kayak launch, Clubhouse, Pool, Fitness Room, Green Space, Nature Preserve w/Trails. Welcome to this meticulously maintained Craftsman-style home w/ Southern Living front porch & thoughtfully designed luxurious light-filled floor plan. Chef's kitchen w/ expansive island, bar seating, Dual-Fuel Range, tile back splash tile backsplash & Cafe SS appliances. Comfortable open living spaces that flow seamlessly throughout w/fireplace, 8 ft doors, high ceilings. Spacious downstairs owner's suite w/ Spa concept bathroom, tile floors, glass shower, over-sized Garden tub + custom walk-in closet + FF guest bedroom/Home Office w/ add storage. Outdoor oasis that backs to Nature Preserves w/ spacious covered porch, irrigation system, back up generation & MORE! Easy access to I-64, Edinburgh. WELCOME HOME!

409 Tranquility Trace, Chesapeake

$559,000
5 Beds 3 Baths 10646652 MLS
This is classic Great Bridge living at it's best! Nestled on a quiet cul-de-sac in the desirable Southern Pines neighborhood, this beautifully maintained 5-bedroom, 3-bath home offers 2,491 square feet of versatile living space on a private, half-acre wooded lot. A standout feature is the in-law suite, complete with its own bedroom, attached sitting/living area, and full bath ideal for multigenerational living or long-term guests. Two bathrooms have been tastefully renovated, while the newer roof and replacement windows provide added peace of mind. The cozy living room features a gas log/wood-burning fireplace, and the finished room over the garage offers endless flexibility as a bedroom, playroom, media room, or home office. Relax on the welcoming front porch or entertain on the spacious rear deck overlooking the peaceful backyard. Complete with a 2-car attached garage, detached storage shed, and no HOA.

529 Wittington Drive, Chesapeake

$425,000
3 Beds 2.1 Baths 10646473 MLS
Welcome to this beautifully maintained 3 bedroom, 2.5 bath home. Step inside to a bright, open floor plan featuring rich dark wood floors that flow throughout the main living areas. The stunning kitchen is designed to impress with custom cabinetry, upgraded appliances, and plenty of space for cooking and entertaining. The inviting great room is the heart of the home, complete with gas fireplace and custom built-in shelving, creating the perfect space to relax or gather with family and friends. Upstairs, you'll find spacious bedrooms, including a comfortable primary suite, offering room for everyone to spread out. Outside, enjoy your own private patio, ideal for morning coffee or simply unwinding after a long day. Residents enjoy fantastic community amenities, including a pool, clubhouse, and exterior grounds maintenance, allowing you to spend more time enjoying your home and less time on upkeep. BRAND NEW ROOF (July 2026). Don’t miss your opportunity to make this your next home!

515 Sweet Leaf Place, Chesapeake

$560,000
4 Beds 2 Baths 10646286 MLS
Escape to your own private waterfront retreat on nearly 1/2 acre in the sought-after Inland Colony community, where peaceful wooded surroundings and serene water views create the perfect connection to nature. This 2,494 sq. ft. home offers 4 bedrooms, 2 baths, a first-floor primary suite, detached ADU, 1-car garage, and private dock with access to the Intracoastal Waterway on the Elizabeth River. Enjoy the expansive deck overlooking the backyard and water or unwind on the screened porch off the primary suite. Fresh paint and new carpet enhance the bedrooms, while the spacious kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and generous prep space. French doors open from the dining room to the living area, creating an ideal layout for entertaining. The FROG with new carpet and large walk-in attic provide excellent flexibility and storage. Some photos may be virtually staged. Conveniently located near shopping, dining, top-rated schools, and interstate access while offering a true waterfront escape.

1145 Sunlight Drive, Chesapeake

$289,000
3 Beds 1 Baths 10646147 MLS
Welcome home to this charming ranch that's full of warmth, character, and timeless appeal! Nestled at the end of your street with no through traffic, this adorable home offers the perfect blend of privacy, comfort, and convenience. Enter to discover soaring vaulted ceilings that create an open, airy feel throughout the main living spaces. With two inviting fireplaces and two separate dens, there's plenty of room to gather with family, entertain guests, or simply relax with a good book. The spacious eat-in kitchen is great for casual mornings, while the adjoining dining area is ready for holiday meals and special celebrations. Every room is filled with charm, making this home feel welcoming from the moment you walk through the door. Outside, you'll love the yard, offering endless possibilities for gardening, play, pets, or creating your own backyard oasis. The oversized carport provides excellent covered parking and additional storage space.

1106 Maryview Avenue, Chesapeake

$700,000
5 Beds 2.1 Baths 10645293 MLS
Tucked away on a quiet cul-de-sac, this beautifully maintained custom home offers the perfect combination of quality construction, thoughtful upgrades, and everyday comfort. Built in 2004 and offering approximately 3,300 square feet, this all-brick home features 5 bedrooms, with 4 conveniently located on the first floor, providing exceptional flexibility for families, guests, or multi-generational living. From the moment you step inside, you'll appreciate the soaring cathedral ceilings, spacious living areas, and inviting gas fireplace that create a warm and welcoming atmosphere. The private primary suite offers a relaxing retreat with a jetted soaking tub and generous walk-in closets. One of this home's standout features is the incredible backyard privacy. Whether you're enjoying your morning coffee, hosting family and friends on the large deck, or simply unwinding after a long day, you'll love the peaceful setting and the feeling of having your own private oasis. This home also offers valuable upgrades that provide peace of mind for years to come. A whole-house generator ensures you're prepared and comfortable during unexpected power outages and reflects the care and attention given to maintaining the home. An irrigation system keeps the lawn looking its best with minimal effort. Located in the highly sought-after Hickory school district, this home delivers the rare combination of timeless all-brick construction, flexible living space, exceptional privacy, and important long-term investments that today's buyers appreciate. If you've been searching for a home that is as practical as it is beautiful, this one is not to be missed. Some photos have been virtually staged.

1104 Arabian Arch, 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, 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.