Refine Search
Sort by
1432 Scoonie Pointe Drive, South Chesapeake
$449,900
3 Beds ⋅ 2 Baths ⋅ 10658513 MLS
Welcome to 1432 Scoonie Pointe Drive in Chesapeake! Enjoy comfortable, low-maintenance living in this desirable 55+ community. This inviting home features an open floor plan, cathedral ceilings, and convenient one-level living. Handicap-accessible features add comfort and ease, while the sunroom provides the perfect spot to relax, enjoy your morning coffee, or entertain guests. Residents can take advantage of wonderful community amenities, including a swimming pool and clubhouse. With ground maintenance included, you can spend more time enjoying life and less time worrying about upkeep. Conveniently located near shopping, restaurants, and everyday essentials, this home offers a wonderful combination of comfort, convenience, and community living. If you're looking to simplify your lifestyle without sacrificing comfort or amenities, this home is a must-see! Please verify the community's 55+ age requirements and 80/20 homeowner eligibility guidelines.

1432 Scoonie Pointe Drive, South Chesapeake

1325 Debbs Lane, South Chesapeake
$420,000
4 Beds ⋅ 2.1 Baths ⋅ 10658609 MLS
Welcome to this beautifully updated 4-bedroom, 2.5-bath home in the heart of Chesapeake's Greenbrier area. Enjoy fresh paint, new LVP flooring, and new carpet throughout. The spacious, open floor plain is great for entertaining, hosting gatherings, and everyday living. The generous kitchen features granite countertops and stainless-steel appliances, making meal preparation a pleasure. Head outdoors to your large paver patio and enjoy the privacy of a fenced backyard, desirable for relaxing or entertaining outdoors. The attached garage offers added convenience with a new garage door opener. Centrally located near military bases, beaches, medical facilities, shopping, restaurants, and major interstates, this home combines modern updates, comfortable living, and a convenient location! Don't miss the opportunity to make this wonderful home yours!

1325 Debbs Lane, South Chesapeake

2304 Swinson Landing, South Chesapeake
$430,000
4 Beds ⋅ 2 Baths ⋅ 10658594 MLS
Welcome to 2304 Swinson Landing! Tucked away on a cul-de-sac with no HOA, this charming 4-bedroom, 2-bath ranch offers approximately 1,800 square feet of comfortable living space and a peaceful wooded backdrop. Inside, you'll find a bright, inviting kitchen featuring a beautiful bay window overlooking the backyard, bringing the outdoors right into your everyday routine. Enjoy slow mornings with coffee on the screened-in porch, host friends on the spacious back deck, or simply unwind while taking in the wooded views. The versatile finished room over the garage (FROG) provides additional space to fit your needs, along with plenty of storage. An attached garage offers even more room for parking, hobbies, or organization. With a roof, HVAC system, and appliances updated in 2017, this home combines practical features with inviting spaces to enjoy. Conveniently located in Chesapeake, this is one you won't want to miss!

2304 Swinson Landing, South Chesapeake

2213 Wildwood Road, South Chesapeake
$418,899
4 Beds ⋅ 2 Baths ⋅ 10658565 MLS
Charming brick home with plenty of character, versatile living spaces, and a backyard made for entertaining! Offering 4 bedrooms and 2 full baths, this home features hardwood floors, a cozy gas fireplace, and a first-floor bedroom for added flexibility. The upper level provides additional bedrooms with their own unique character. Enjoy outdoor living on the screened porch or deck overlooking the fenced backyard and in-ground swimming pool. A detached brick building with its own kitchenette and full bathroom offers additional possibilities for a hobby space, workshop, or poolside entertaining. Situated on approximately a quarter-acre lot with no HOA, this property offers a wonderful combination of indoor and outdoor space, distinctive features, and the opportunity to make it your own! Opportunity for up to $3500 lender credit with use of preferred lender.

2213 Wildwood Road, South Chesapeake

518 Eldridge Lane, South Chesapeake
$469,900
3 Beds ⋅ 2.1 Baths ⋅ 10658549 MLS
Built in 2023, this modern home has it all. From the 2-story foyer, the great room awaits with cathedral ceilings and abundant natural light. The kitchen features quartz countertops, stainless energy-efficient appliances, 42-inch cabinets, and modern black fixtures. Just off the kitchen, you'll find the half bath and mudroom/ laundroom leading to the attached 2-car garage, complete with epoxy floors and storage racks. A prime first-floor primary suite features tray ceilings, a dual-vanity bath, a tiled shower, and a walk-in closet. Upstairs, you will find a versatile loft, open to the living room below, a full bath, and two additional bedrooms, each with its own walk-in closet. Enjoy top-tier community amenities including a pavilion, splash pad, dog park, playground, and walking trails, all conveniently located near Cahoon Parkway, schools, shopping, and major interstates for an easy commute.

518 Eldridge Lane, South Chesapeake

514 Trellis Trail, South Chesapeake
$329,000
2 Beds ⋅ 2.1 Baths ⋅ 10658445 MLS
Come check out this Spacious 1,870-square-foot, 2-bedroom +1 bonus room townhome in a four-unit building. Peacefully set among trees, the home offers a feeling of privacy. The Grove at the Arboretum neighborhood (situated around Green Tree Road) sits directly adjacent to the arboretum grounds, making it a very short walk or a distance of less than a half-mile away. A public nature site featuring shaded hardwood forest trails, demo gardens, an 18th-century farmhouse, and Camellia Cove. BRAND NEW air conditioning unit will keep you cool on hot summer days. The versatile first-floor office can easily serve as a third bedroom, guest room, or flex space. Beautiful wood floors throughout the lower level offer aesthetic appeal and simplify cleaning and maintenance. An oversized kitchen features a generous pantry, breakfast area, and plenty of cabinet space & counter seating. Sliding glass doors open to a private, fenced in patio, wonderful for relaxing or entertaining. Upstairs, you'll find two generously sized primary suites, each with its own private full bathroom, providing comfort and privacy for residents and guests alike. A spacious second floor laundry room includes washer and dryer hookups and a utility sink for added convenience. Community amenities include a sparkling swimming pool, grounds maintenance, trash pickup, and sewer, all included with the HOA. Ideally located in the sought-after Greenbrier area, with easy access to interstates 64/264/664/17, shopping centers/mall, and fantastic local dining. Quick move-in available, come see this beauty today! Also for rent $2500/Month, available now.

514 Trellis Trail, South Chesapeake

2500 Deal's Creek Court Court, South Chesapeake
$629,777
4 Beds ⋅ 3.2 Baths ⋅ 10658394 MLS
Stunning new construction ranch home by an experienced, award-winning builder is move in ready! The popular Sandpiper model offers an open-concept main level designed for comfortable living and entertaining. The great room flows into the gourmet kitchen, featuring custom cabinetry, a large granite island, & stainless steel appliances. The primary suite is a private retreat with a generous walk-in closet & spa-inspired bath with LVT flooring, tub, tiled shower, double vanity, and private water closet. Two additional large bedrooms and a full hall bath are conveniently located on the main level. A fourth room situated over the garage includes its own full bath, making it ideal for guests, a home office, or bonus living space. Other features include a large utility room located just off the two-car garage, 9-foot ceilings, upscale LVT and carpet flooring, and an electronic fireplace with mantle. Large 1.7-acre lot close to interstates, schools and shopping.

2500 Deal's Creek Court Court, South Chesapeake

905 Camp Street, South Chesapeake
$599,000
4 Beds ⋅ 3.1 Baths ⋅ 10658354 MLS
A Community with year-round events, clubhouse, pool, playgrounds and a brand NEW school scheduled to open in 2027, that would be Culpepper Landing in Chesapeake! The BEST part is this like new home, built in 2021 & meticulously maintained! It offers 4 Bedrms, 3 1/2 Bath, almost 2,500 sqft of open, bright natural light, living space. A FROG that is private off of the kitchen w/its own full bath & walk-in closet, could be used as multi-generational liv'g as an In-law Suite, or flex space. A Large eat-in kitchen w/custom cabinets, an abundance of storage, granite counters, SS appliances, & an XL island perfect for a family & entertaining. Upstairs you'll find a large laundry room, primary bedroom w/tray ceiling, ensuite bath, & walk-in closet it truly is your own peaceful retreat. A 3rd full bath & 2 large bedrooms upstairs give you a very versatile layout. Relax in fenced in backyard, this home was designed for everyday living w/plenty of room to spread out! Min from shopping/interstates

905 Camp Street, South Chesapeake

518 Silk Tree Lane, South Chesapeake
$449,900
3 Beds ⋅ 2.1 Baths ⋅ 10658185 MLS
Step into unparalleled luxury at 518 Silk Tree Lane, nestled in the quaint, village-like community of North Trail in the highly sought-after Greenbrier area. This 2,366 square-foot masterpiece is completely turn-key. Absolutely no upgrades are needed here. Every high-end detail has already been meticulously curated for you. The stunning gourmet kitchen is a true showstopper, featuring custom cabinetry and countertops, stainless steel appliances from the Frigidaire Professional Series - double wall ovens, a gas range, microwave, wine refrigerator, and built-in ice maker. Porcelain flooring flows throughout the living room, dining area, and kitchen, while well-maintained carpeting adds warmth and comfort to the upstairs and bedrooms. The commitment to high-end living extends into the bathrooms, which have been transformed into private, spa-like retreats featuring breathtaking custom walk-in showers with artisan tile work and built-in bench seating. A cleverly crafted bonus office space is perfectly situated just at the top right of the staircase, offering an ideal, quiet sanctuary for remote work. Storage abounds with custom built-ins and a walk-in attic. Enjoy the spacious custom paver patio with views of the serene community pond and fountains. Additional highlights include three-zone HVAC, Rinnai tankless water heater, custom trim and moldings, Bose surround sound, Cox security wiring, and an EV charging station. Embrace the ultimate low-maintenance lifestyle. The comprehensive condo fee covers all exterior grounds maintenance and trash pickup. Conveniently located in the heart of Chesapeake. Truly a must-see!

518 Silk Tree Lane, South Chesapeake

4640 Ballahack Road, South Chesapeake
$589,900
3 Beds ⋅ 2.1 Baths ⋅ 10657850 MLS
Welcome home to this well-built, lovingly maintained brick ranch framed by mature trees, dogwoods, boxwoods and elephant ear plants that offer beautiful summer shade on 1.67+ acre lot. A charming front porch with newer brick flooring and stately columns sets the tone. Inside, enjoy updated flooring throughout, an updated primary bath and a stunning French country kitchen, remodeled floor to ceiling, expanded into the den with extra cabinetry (wine, & dish cabinet and bench) and a breakfast area. The bright FROG offers flexible space for a home theater, hobby room, playroom or 4th guest bedroom with access to a huge floored and lighted attic. Relax on the screened porch with its "pet and kid friendly" brick base, gather on the paver patio or unwind by the fire pit. Custom Shutters offer evening privacy. A garden for homegrown produce, detached lighted garage with large workshop. French drain system, multiple parking spots and freshly painted trim complete this inviting home!

4640 Ballahack Road, South Chesapeake

217 Maggie Bell Ln., South Chesapeake
$619,900
4 Beds ⋅ 2.1 Baths ⋅ 10657959 MLS
To Be Built - Primrose Plan with first floor Primary BR and 3 BRs up! GPS 369 Scotland Ln. Chesapeake OPEN S/S 1-4. Nestled in Greenbrier come visit the newest community by renowned local builder. Primrose Cottage welcomes you with a charming full front porch, soaring two-story foyer and family room, and beautiful hardwood flooring throughout the main living areas. Designed for easy living and entertaining with open layout connects the family room, dining area, and dreamy chef’s kitchen featuring oversized quartz island, custom hood and designer finishes,. The first-floor primary suite offers a custom walk-in closet, spa-like bath with quartz dual vanity, tiled shower, and private laundry. Upstairs 3 spacious bedrooms, tons of storage & 2nd laundry room (may add 3rd opt Full Bath). Professionally managed grounds for a low-maintenance lifestyle, giving you more time to enjoy the comfort, quality, and craftsmanship of your Primrose haven.

217 Maggie Bell Ln., South Chesapeake

1266 Auburn Hill Drive, South Chesapeake
$725,000
5 Beds ⋅ 3 Baths ⋅ 10657857 MLS
Experience refined comfort in sought-after Albemarle River! Tucked away on a beautiful corner lot yet near I-64, shopping, dining, & all Greenbrier has to offer, this exceptional one-owner Craftsman home has been meticulously maintained. Beautiful Craftsman trim, columns on front porch, hardwood floors, & an inviting open floor plan create a warm, elegant feel. The kitchen features Cortez countertops and stainless-steel appliances. The expanded primary suite offers a custom dream closet & spa-inspired bath with dual vanities, walk-in shower, & oversized soaking tub. The FROG offers flexible space for a 4th bedroom, office, or media room. Step outside to your private backyard oasis with a sparkling heated saltwater in-ground pool, & plenty of room to entertain. Beautifully cared for and move-in ready, this is the one you've been waiting for!

1266 Auburn Hill Drive, South Chesapeake

844 Greenfield Lane, South Chesapeake
$950,000
6 Beds ⋅ 5.1 Baths ⋅ 10658157 MLS
All-brick home offering over 5,000 sq. ft. of versatile living space and exceptional indoor–outdoor amenities. With 6 bedrooms, 5.5 bathrooms, and an additional first-floor flex room perfect as a 7th bedroom, home office, or formal living area, this home adapts beautifully to your lifestyle. Five of the bedrooms include private en-suite bathrooms, giving everyone their own comfortable retreat. A bright, oversized sunroom—equipped with heating and cooling but not included in the home’s total square footage—adds even more year-round living space. Step outside to your own backyard oasis. Brick pool house with heating/cooling + full bathroom. In-ground saltwater pool with a new liner ( installed 2025). Hot tub for 6. Expansive patio area for entertaining and relaxing. The property also features a three-car garage plus a half-circle driveway providing abundant parking for guests. freshly painted, new carpets, refinished wood floors. Interior pics virtually staged.

844 Greenfield Lane, 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

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

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

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

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.

How much is your home worth?

Get instant property value now!