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1108 Cumberland Court, South Chesapeake
$600,000
4 Beds ⋅ 3 Baths ⋅ 10657974 MLS
Welcome to 1108 Cumberland Ct, a beautifully staged Chesapeake home with a pool and a fenced backyard made for entertaining. Inside, enjoy bamboo flooring and premium crown molding throughout the main level. The kitchen features granite counters, tiled backsplash, a pocket door, a gas range (2022), a 2024 dishwasher, and whole-house plus reverse-osmosis water filtration. A full downstairs bath with a walk-in shower adds convenience, and the wood-burning fireplace is perfect for cool evenings. Major updates include roof and skylights (2015), gas furnace and A/C (2017), front windows (2020), and an encapsulated crawl space with new vapor barrier (2022). Walk-in attic, garage shelving, and comfort-height toilets. Open house Saturday, 10/17. Schedule your showing today!

1108 Cumberland Court, South Chesapeake

603 Oxbow Court, South Chesapeake
$850,000
5 Beds ⋅ 3 Baths ⋅ 10657808 MLS
This is the kind of Chesapeake home that feels substantial the second you walk in. Restored inside and out, it carries the scale and character of an established traditional home, with beautiful arched doorways, refinished hardwoods, fresh paint, new carpet, and thoughtful updates that make the entire house feel fresh again. The main level is generous without feeling disconnected. The kitchen sits between the formal dining room, the vast open living space, and the screened porch, making it the natural link between everyday living and entertaining. Ample white cabinetry wraps the room, while an oversized island, thick warm granite countertops, a ceramic Kohler sink, and new appliances give it both presence and function. From there, the screened porch opens to the rear deck and draws you straight out toward the pool. That backyard deserves its own moment. The in-ground pool sits within a wide paver surround and includes a diving board and built-in sitting ledge, all framed by decorative iron fencing. But the fence is not the end of the yard. The property continues beyond it with additional lawn space and an in-ground fire pit, giving the outdoor space far more depth than the pool area first reveals. Inside, nearly every turn brings another room with a purpose. A dedicated library adds character to the main level, while the separate billiard room creates another substantial place to gather. A first-floor bedroom sits near a modern updated full bath, and upstairs, a finished attic adds even more usable space with room for movies, games, hobbies, or whatever comes next. Then there is the primary suite, and it is genuinely oversized. Beyond the sleeping area is a separate sitting room, an enormous walk-in closet, and an ensuite with a jetted soaking tub and separate stand-up shower. Set in Carriage House Estates in Chesapeake’s 23322 with Hickory schools and a central location, this is a home where the size, flow, and character show up in all the right places—inside, outside, and in the spaces you do not expect until you are standing in them.

603 Oxbow Court, South Chesapeake

821 Redleafe Circle, South Chesapeake
$980,000
6 Beds ⋅ 4 Baths ⋅ 10657839 MLS
An exceptional opportunity to own a Stephen Alexander custom home in Greystone, one of Chesapeake's premier luxury communities where homes are rarely available. This expansive executive residence blends timeless craftsmanship with the space, flexibility, and resort-style amenities today's luxury buyers seek. A first-floor bedroom with an adjacent full bath offers versatility for guests, a home office, or multi-generational living. The primary suite is a true retreat with a fireplace, sitting area, and four closets. Enjoy a private backyard oasis featuring an in-ground pool, hot tub, screened porch, gazebo, fire pit, privacy fence, irrigation well, and expanded parking for a boat or RV. Scenic walking paths enhance this sought-after community. Significant recent investments include a new roof (2026), three HVAC systems, an encapsulated crawl space, new hardwood flooring, updated bath vanities, freshly painted kitchen cabinetry, and a new oven. Schedule your private showing today!

821 Redleafe Circle, South Chesapeake

810 Hedgerow Court, South Chesapeake
$675,000
5 Beds ⋅ 3 Baths ⋅ 10657871 MLS
Well maintained all brick home with 2-car side loading garage, long driveway, 1/3 acre beautifully landscaped lot, situated on a cul-de-sac in Great Bridge. Open floor plan features huge kitchen with quartz countertops and overlooks fam room. FR has wood burning FP which is also plumbed for gas. In addition to the 5 bedrooms on 2nd floor, there is a 6th bedroom/office with adjacent full bathroom on 1st floor. Recent updates include 2nd floor 3 ton HVAC (Sept 2026), new carpets (Sept 2026), windows, roof, water heater, garage door, leaf filter gutters, more. Award winning Cheshire Forest community amenities include clubhouse, pool, tennis/pickle ball courts, parks and playgrounds. Screened porch with concrete floor overlooks the beautiful backyard. Seller to provide clear Termite/Moisture letters and 1 year home warranty.

810 Hedgerow Court, South Chesapeake

938 Olmstead Street, South Chesapeake
$630,000
5 Beds ⋅ 3.1 Baths ⋅ 10657755 MLS
Gorgeous & 4-years-young in community-friendly Culpepper Landing with scenic outdoor areas, clubhouse & pool! Huge open & bright floor plan enhanced by classic neutral décor. Enjoy flexible living spaces great for home office, study, dining room or homeschool station. Dreamy kitchen with an abundance of cabinetry, counter space & massive breakfast bar great for gathering & entertaining. Inviting family room sits at the heart of the home & opens to covered porch overlooking fenced backyard. Extra highlights include a convenient mudroom, organization area & finished room over the garage with full bath offering endless possibilities for a guest suite, media room or private retreat. With 5 bedrooms & 3.5 bathrooms, there's plenty of room for everyone to spread out. Elegant primary suite features exercise area, walk-in closet, dual-sink vanity & oversized shower with double shower heads. This is the Total Package & Across the street from brand NEW elementary school opening 2027-2028.

938 Olmstead Street, South Chesapeake

2711 Lake Drummond Cswy, South Chesapeake
$625,000
4 Beds ⋅ 2.1 Baths ⋅ 10657073 MLS
** INCREDIBLE OPPORTUNITY ** An exceptional combination of space, privacy and versatility awaits on nearly 4 acres with this beautifully refreshed 4-bedroom, 2.5-bath home! Has the following FEATURES: Freshly Painted throughout, Large Family Room with a Wood Burning Fireplace, New LVP Flooring, Great Kitchen with a Full Stainless Steel Appliance Package, wrap around bar and Eat-In Breakfast Area, Formal Dining Room and MORE!! Additional HIGHLIGHTS: 4 comfortable Bedrooms along with a LARGE FROG (Finished Room Over Garage) that offers exceptional versatility as possible media or recreation room, home office, playroom, hobby space, guest area or whatever best suits your needs, 2 Car Attached Garage, generous rear deck provides an ideal setting for morning coffee, afternoon relaxation or memorable gatherings with family and friends. Step outside and discover the true appeal of this expansive nearly 4-acre property. There's plenty of room to enjoy the peaceful surroundings, entertain outdoors, garden, play, accommodate pets or simply relax and enjoy the privacy and freedom that come with owning a larger homesite. With its beautiful setting, spacious living areas and nearly 4 acres of land, this is a rare and truly special opportunity that offers the space, flexibility and lifestyle you've been looking for!

2711 Lake Drummond Cswy, South Chesapeake

628 Gladesdale Drive, South Chesapeake
$499,900
4 Beds ⋅ 2 Baths ⋅ 10657378 MLS
Well maintained all brick ranch on a large .34 acre corner lot in the Hickory School District . Enter the large greatroom through foyer which opens to formal dining room. Greatroom features chairrail, wainscoating, exposed beams, built in bookcase and masonry wood burning fireplace.Kitchen has been updated with new cabinet faces, countertops and laminate floors; all appliances convey. Primary bath updated with new vanity, toilet and has tile floor. Hall bath updated with new toilet. Laundry closet convenietly off eat-in area in kitchen. Large frog has plenty of head space and large closet; partially floored walk in attic. HVAC, hot water heater newer, encapsulated crawl with dehumidifier. Large deck off greatroom. No neighborhood fees.

628 Gladesdale Drive, South Chesapeake

616 Rutherford Drive, South Chesapeake
$549,900
3 Beds ⋅ 1.1 Baths ⋅ 10657745 MLS
Well-maintained, move-in-ready brick ranch in an established neighborhood with wide sidewalks! Features attractive LVP flooring throughout, three bedrooms, and a primary suite with a walk-in closet. Enjoy the gas log fireplace and additional storage with floored attic space. The converted attached garage is currently equipped as a beauty salon with styling station, shampoo sink, built-in cabinetry, and laundry area. A bright 20' x 20' sunroom with three walls of casement windows overlooks the backyard. Outdoor amenities include a 20' x 20' composite deck, fenced yard, and a 20' x 40' in-ground pool with cover. The detached three-bay garage includes power, workbenches, and pull-down access to a large, floored attic. A rare combination of comfort, functionality, and exceptional indoor and outdoor living space.

616 Rutherford Drive, South Chesapeake

443 Supplejack Court, South Chesapeake
$489,900
4 Beds ⋅ 2 Baths ⋅ 10657404 MLS
Welcome to sought-after Riverwalk! This beautifully maintained 4-bedroom, 2-bath ranch sits on a desirable corner lot with great curb appeal. The freshly painted interior offers an inviting floor plan, vaulted ceilings, updated lighting, luxury vinyl plank flooring, and thoughtful custom touches, including enhanced closet space and added shelving. The kitchen features quartz countertops, stainless steel appliances, and two pantries. A versatile 4th bedroom/FROG above the 2-car garage offers flexible space for guests, an office, or hobbies. Enjoy the beautifully landscaped backyard with a deck and paver patio, perfect for outdoor entertaining. Riverwalk amenities include a clubhouse, pool, dock, boat ramp, playground, trails, tennis and pickleball courts, plus seasonal concerts and food trucks. Discover the charm, convenience, and lifestyle that make Riverwalk a wonderful place to call home!

443 Supplejack Court, South Chesapeake

908 Levee Court, South Chesapeake
$420,000
3 Beds ⋅ 2 Baths ⋅ 10657748 MLS
Welcome home to this charming, well-maintained ranch-style home in Chesapeake, VA! Offering move-in-ready, one-level living, this home features 3 spacious bedrooms, 2 full updated bathrooms, an updated eat-in kitchen with new appliances, and washer and dryer. The roof was replaced in 2021, providing added peace of mind. Outside, enjoy a large backyard with plenty of space for entertaining, pets, gardening, or relaxing. A detached garage provides additional storage or workshop space. Conveniently located near shopping, dining, everyday amenities, and major Hampton Roads interstates. If you're looking for a 3-bedroom ranch-style home for sale in Chesapeake, Virginia with an updated kitchen, detached garage, and spacious backyard, this home is a must-see. Schedule your private showing today!

908 Levee Court, South Chesapeake

1268 Kidbrooke Street, South Chesapeake
$835,990
6 Beds ⋅ 5 Baths ⋅ 10657735 MLS
QUICK MOVE-IN! Welcome to the Summit floor plan, a spacious and thoughtfully designed home offering exceptional living space across three finished levels. The main level features a private first-floor bedroom with full bath, plus a versatile office or formal dining room. At the heart of the home, the upgraded kitchen showcases an oversized island, premium quartz countertops, soft-close cabinetry, walk-in pantry, and stainless-steel appliances, including a wall oven with built-in microwave and gas cooktop. The kitchen flows seamlessly into the inviting great room, complete with a gas fireplace. Upstairs, retreat to the luxurious owner’s suite featuring a huge walk-in closet, dual vanities, relaxing soaking tub, and separate shower. Three additional spacious bedrooms, two full baths, a convenient laundry room, and an open loft provide plenty of flexible space. The finished basement adds even more possibilities with a recreation room, media room, and additional bedroom suite. Enjoy a welcoming community complete with walking trails and a fire pit. Incredible incentives with use of preferred lender! Photos and renderings are from the builder’s library; actual finishes and features may vary.

1268 Kidbrooke Street, South Chesapeake

3616 Riverwood Crescent, South Chesapeake
$750,000
4 Beds ⋅ 3 Baths ⋅ 10657714 MLS
COUNTRY LIVING AT ITS BEST!Imagine sipping your morning coffee while deer graze in your backyard! This incredible 3-acre property in desirable Hickory/Grassfield offers privacy, space, and endless possibilities!2,200 sq ft home with 4 bedrooms and 3 fully renovated bathrooms, a cozy wood-burning fireplace, new waterproof laminate flooring throughout, and a 2-car attached garage.The 1,500 sq ft workshop features a vehicle lift — perfect for car enthusiasts, hobbies, or business needs!Enjoy one of the largest above-ground pools available, extensive decking, and a recently repaired and painted shed.Additional features include newer HVAC and appliances, an excellent water softener, and a sealed crawlspace with dehumidifier and warranty.Not in a designated flood zone!Three acres, a spacious workshop, and your own private backyard oasis in the sought-after Hickory/Grassfield school district!Country charm, modern comforts, and room to live your way!

3616 Riverwood Crescent, South Chesapeake

2008 Pocaty Creek Lane, South Chesapeake
$889,500
4 Beds ⋅ 3.1 Baths ⋅ 10657656 MLS
Enjoy a slower pace of life as you relax on the front porch w/ morning coffee or watch loved ones play in the expansive yard. This beautifully remodeled farmhouse-style home sits on approx. 5.207 acres, extensively updated in 2021.Step inside to a dramatic 2-story foyer that opens to a spacious living area kitchen, dining, & family room, ideal for everyday living & entertaining. The 1st-floor primary suite offers comfort & convenience. Upstairs, you'll find a generous flex space perfect for a 2nd living area, home office, playroom, or gym. The 2nd level also features a second bedroom suite w/ private bath, plus 2 more bedrooms connected by a Jack/Jill bath. Abundant storage can be found throughout the home. The outdoor lifestyle is just as inviting. Spend your days fishing in your private pond, harvesting produce from the garden, or enjoying peaceful views of the neighboring horse farm from your kitchen window, at the end of the day, unwind by the pool.

2008 Pocaty Creek Lane, South Chesapeake

MM Bellhaven, South Chesapeake
$720,000
5 Beds ⋅ 2.1 Baths ⋅ 10657643 MLS
The Bellhaven at Riverview Landing by Wetherington Homes offers a flexible 4-5 bedroom floor plan with an open-concept layout designed for everyday living and entertaining. The kitchen flows seamlessly through the butler's pantry into the dining area, creating a functional and connected space. A thoughtfully curated list of standard features is included, along with optional upgrades to personalize the home. Choose your lot and design options. Enjoy a convenient, centrally located community with easy access to shopping, medical facilities, dining, major interstates, and area beaches. The property is situated in the Hickory school district, an ideal setting for those seeking accessibility and everyday convenience. Ask about our current incentives! Directions: Mt. Pleasant Rd. to Back Road to Intracoastal Way. Follow the Wetherington Homes signs.

MM Bellhaven, South Chesapeake

381 Scotland Lane, South Chesapeake
$613,900
3 Beds ⋅ 2.1 Baths ⋅ 10657357 MLS
To Be Built - MODEL 369 Scotland Ln. nestled in Greenbrier, Joseph’s Meadow built by renowned builder. The Lily Cottage welcomes you w/ full front porch, airy 10-foot ceilings, & beautiful hardwood floors throughout first floor. Designed for everyday living & entertaining, the open-concept layout seamlessly connects living room, dining area, & stunning chef’s kitchen w/ Cotton White 42" cabinets, 9-foot quartz island, custom hood, and oversized walk-in pantry. Mudroom and powder room conveniently tucked by 2-car garage. Upstairs, a sun-filled loft, bath dual sinks and separate tub/shower room, 3 spacious bedrooms and a large laundry room provide exceptional functionality. Private primary suite offers a custom walk-in closet and tiled spa bath w/ quartz countertops, dual vanities, freestanding tub, tiled shower, and private water closet. Easy living with professionally managed grounds ensures low-maintenance living, making your dream truly a haven.

381 Scotland Lane, South Chesapeake

377 Scotland Lane, South Chesapeake
$612,500
4 Beds ⋅ 2.1 Baths ⋅ 10657358 MLS
To Be Built - LOW Rate and NO PMI! Joseph’s Meadow MODEL GPS 369 Scotland Ln. Chesapeake. Nestled in Greenbrier come visit the newest community by renowned local builder. Lily Cottage welcomes you w/ a full front porch, airy 10-foot ceilings and hardwood floors entire first floor. Designed for entertaining, the open-concept layout seamlessly connects the living room, dining area, and stunning chef’s kitchen featuring a 9-foot quartz island, custom hood, and HUGE walk-in pantry. Mudroom and powder room are conveniently tucked away by 2-car garage. Custom stair detail takes you to FOUR bedrooms with hall bath w/dual sinks, private tub/shower and water closet. BIG laundry room. LUSH Primary suite entry w/custom walk-in closet and SPA retreat w/ quartz countertops, dual vanities, freestanding tub, tiled shower & private water closet. Easy living w/ professionally managed grounds ensures low-maintenance living, making your dream truly peaceful haven.

377 Scotland Lane, South Chesapeake

509 Ballahack Road, South Chesapeake
$1,199,000
5 Beds ⋅ 3.1 Baths ⋅ 10657504 MLS
Welcome home!! 28.18 private acres, 3,714 sq ft, 5 bedrooms, 3.5 updated baths, TWO primary suites, a detached 4-car garage & 20x30 workshop—all in Chesapeake’s sought-after Hickory area?! Yes! Here at 509 Ballahack Rd. Extensively improved inside and out, this one-of-a-kind property delivers the space, flexibility and freedom of country living with modern comfort. Abundant natural light fills the spacious living areas, while warm finishes and thoughtful updates create an inviting feel throughout. The kitchen is complemented by a butler pantry with granite countertop, cabinetry and additional storage, adding function for everyday living and entertaining. The rare dual-primary layout offers one suite on each level, both with private ensuite baths—ideal for multigenerational living, extended guests or added privacy. The main-level primary has been refreshed with new flooring, paint, lighting and hardware. Upstairs, the second primary features a showstopping spa-inspired ensuite with an oversized wet room, rainfall shower, body jets, two-person soaking tub, porcelain tile and polished marble mosaic. All 3.5 bathrooms have been updated with fresh flooring, lighting, paint, mirrors and hardware. Outside, enjoy a nearly wraparound front porch, expansive 20x40 composite deck, outdoor kitchen setup, custom fire pit, fruit trees, grape vines and 28+ acres to explore. Proven deer and turkey hunting is literally steps from your back door, with private shooting and archery areas already in place. The detached 4-car garage provides exceptional storage, while the 20x30 workshop features concrete flooring, lighting and its own electrical panel. Additional improvements include 33 solar panels, Level 2 EV charger, major electrical upgrades, crawlspace encapsulation, updated HVAC and a private well with NO monthly water bill. A rare combination of acreage, recreation, extensive improvements and flexible living in Southern Chesapeake. See attached Feature & Upgrade Sheet for even more! Some listing photographs have been staged by Artificial Intelligence.

509 Ballahack Road, South Chesapeake

844 Parapet Road, South Chesapeake
$345,000
4 Beds ⋅ 2.1 Baths ⋅ 10657384 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

530 San Pedro Drive, South Chesapeake
$670,000
4 Beds ⋅ 3 Baths ⋅ 10657170 MLS
Welcome to Las Gaviotas, where golf course living meets your own backyard oasis! This sprawling 4-bedroom brick ranch offers beautiful golf course and water views, impressive vaulted ceilings, exposed beams, and a stunning two sided fireplace connecting the great room and sunroom. The beautifully renovated kitchen features a large center island and gas cooktop, while the spacious primary suite offers peaceful views and a luxurious bath. Step outside to your private retreat featuring an inground pool with updated liner, hot tub, gorgeous new paver patio, and outdoor gas kitchen for entertaining! Additional highlights include updated bathrooms, kitchen, expansive laundry room, new fixtures, Updated Flooring and Paint, HVAC (2024), roof (2019), and new water heater. Seller to provide a clear termite and moisture letter. A rare opportunity to enjoy single level living, incredible outdoor entertaining, and scenic surroundings!

530 San Pedro 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.

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