South Chesapeake VA 5 Bedroom Real Estate, Homes, Condos for Sale

1128 Plantation Lakes Circle, South Chesapeake

Spacious 5-bedroom, 3-full-bath home offering approximately 2,800 square feet in Chesapeake's desirable Plantation Lakes neighborhood! Featuring a generous floor plan with formal living and dining rooms, a large family room with custom built-ins, and an inviting kitchen with granite center island, breakfast bar, and plenty of room to gather. The primary suite offers a jetted tub and separate shower, while the finished room over the garage provides additional flexible living space. Step outside and enjoy your own backyard retreat featuring an above ground swimming pool, deck, and privacy-fenced yard. Additional highlights include a welcoming front porch, attached 2-car garage, and solar panels for potential energy savings. Conveniently located in the Greenbrier area near shopping, dining, and major commuter routes. Home, swimming pool, and all appliances convey AS IS. Solar panels will be paid off at closing.

1128 Plantation Lakes Circle, South Chesapeake

$665,000

5 Beds ⋅ 2.1 Baths ⋅ 10659965 MLS

Sellers are offering 3% toward buyer’s closing costs with a full price offer! And the backyard gives you even more to get excited about. An in-ground saltwater fiberglass pool installed in 2022 anchors an outdoor setting complete with a paved patio, gazebo, and furnished pool house added in 2023 with electricity and portable HVAC. It’s an outdoor space designed for much more than a swim. Inside, brand-new LVP flooring extends throughout the first floor, bringing a fresh finish to the expansive living area. The kitchen connects to a bright, versatile space that can serve as a sunroom, breakfast nook, or dining area, while a separate office at the rear of the home provides additional flexibility. New blinds add another finishing touch. Upstairs, the spacious primary suite features a generous walk-in closet and private bath with a double vanity, walk-in shower, and separate water closet. Additional rooms offer ample closet space, while upstairs laundry adds everyday convenience. An oversized two-car garage and driveway with parking for up to four vehicles provide even more room for storage and function. The updates go beyond finishes, with a roof, windows, and water heater replaced in 2018, plus partial crawlspace encapsulation completed in 2024. With generous interior living spaces and a backyard that feels like an extension of the home, there’s plenty to appreciate both inside and out.

1617 Banff Court, South Chesapeake

$455,000

5 Beds ⋅ 2 Baths ⋅ 10659859 MLS

Welcome to a rare opportunity in Chesapeake's sought-after Hickory school district! Set on a full acre, this beautifully transformed 5-bedroom, 2-bath home offers the space and setting to enjoy a touch of country living while staying near the conveniences of the city. The renovation goes far beyond cosmetics, with a new roof, siding, windows, HVAC, flooring, carpet, plumbing, septic tank, appliances and more. Inside, fresh modern finishes create a bright, move-in-ready home with room for everyone. Outside, the expansive acre lot opens the door to gardens, outdoor entertaining, hobbies, animals or simply having more room to enjoy the outdoors. With golf courses nearby and easy access to everything Chesapeake has to offer, this property delivers a unique blend of space, location and modern living. Nearly everything has been refreshed or replaced- just bring your furniture and start enjoying the Hickory lifestyle!

1441 Whittamore Road, South Chesapeake

$819,900

5 Beds ⋅ 3.1 Baths ⋅ 10659838 MLS

Incredible opportunity to own the Caymus multi gen model home by McQ Builders in Stoney Creek. Thoughtfully designed and well appointed, you'll be impressed by the style, quality of craftsmanship and attention to detail that McQ Builders is known for! 1st floor multi gen suite has separate entrance from foyer & includes living room, bedroom, full bathroom and 2 walk in closets. Great room open to dining, gourmet kitchen w/ double ovens, gas cooktop w/ range hood, expansive kitchen island & walk in pantry. Spacious primary bedroom offers airy trey ceiling, lg walk in closet. Luxurious primary bath shines w/ LARGE walk in shower, soaking tub & double sink vanity. 3 addt'l bedrooms, large media room, hall bath w/ double sink vanity & spacious laundry room complete 2nd floor. You'll enjoy water views w/fountain from your screened in porch and appreciate mini-split in the garage. Ask for details regarding possession and to schedule your private tour of this outstanding home

1322 Sebastian Court, South Chesapeake

$610,000

5 Beds ⋅ 2.1 Baths ⋅ 10659997 MLS

Welcome to the one that checks all the boxes- space, style, in the heart of Great Bridge location, and a backyard you definitely don’t find every day! Built in 2020, this updated 5-bedroom, 2.5-bath home offers approximately 2,200 square feet and sits on nearly .40 acres in the sought-after Great Bridge school district. While the home may only be a few years old, the current owners didn’t stop with builder finishes, nearly every space has been thoughtfully refreshed with updated paint, upgraded light fixtures, and carefully chosen details throughout. Truly, no room has been left untouched! Step inside to a bright, welcoming floor plan with spacious kitchen features, granite countertops, stainless steel appliances, plenty of cabinetry, and a large island, all opening into the family room with fireplace and a separate dining area. 5 bedrooms located upstairs as well as a dedicated laundry room and spacious primary suite that offers its own private retreat and walk-in closet.

233 Old Drive, South Chesapeake

$749,900

5 Beds ⋅ 3.1 Baths ⋅ 10659868 MLS

Rare opportunity in Culpepper Landing! This spacious home features an open floor plan with five bedrooms, including a first-floor bedroom with ensuite, plus an upstairs loft. The gourmet eat-in kitchen offers a breakfast bar, pantry, and butler’s alcove. Retreat to the primary suite with sitting area and oversized walk-in closet. Enjoy a premium dual-zone architectural audio system with built-in 5-channel surround sound in the main living room and upstairs loft pre-wired for your media setup, without bulky speaker boxes. Freshly painted throughout, with brand-new carpets professionally cleaned. A tankless water heater and fully paid-off solar panels add value. Community amenities include a clubhouse, pool, fitness room, and playgrounds. A new elementary school is within walking distance and scheduled to open in fall 2027. Convenient to shopping, dining, and the interstate. Don’t miss your chance to make this exceptional home yours!

733 Big Bear Lane, South Chesapeake

$749,000

5 Beds ⋅ 2.1 Baths ⋅ 10659866 MLS

Absolutely beautiful custom-built home in the highly sought-after Etheridge Lakes community in the Hickory section of Chesapeake! Lovingly cared for by its original owner, this meticulously maintained property sits on one of the largest lots in the neighborhood, offering nearly half an acre of peaceful pond front living at the end of a quiet cul-de-sac. Featuring five spacious bedrooms, including a first-floor bedroom with a nearby full bath, plus bonus downstairs office. This home offers a versatile floor plan for today's lifestyle. All bathrooms have been tastefully updated, including the primary ensuite. Enjoy the bright, updated white kitchen, fresh interior paint, Trane HVAC systems, and expansive entertaining deck overlooking the pond, where you can even cast a fishing line! Immaculate, move-in ready, and showcasing true pride of ownership! See today

1205 Carey Court, South Chesapeake

$769,740

5 Beds ⋅ 4 Baths ⋅ 10659837 MLS

Welcome to The Summit at Riverview Landing, where you’ll discover thoughtfully designed living space across 2 luxurious floors-perfect for families of every size. The main level impresses with a versatile 1st-floor bedroom and full bath, a flexible office or formal dining room, and a sunlit great room that flows seamlessly from the gourmet kitchen, featuring a large island, quartz countertops, soft-close cabinets, premium stainless steel appliances (including double ovens and a gas cooktop),and a walk-in pantry. Upstairs, unwind in your expansive owner’s suite with a huge closet, double vanities, a relaxing bathtub, and a separate shower, while three additional bedrooms, two full baths, a laundry room, and a loft provide ample space and flexibility. Enjoy a vibrant, amenity-rich community with walking trails and a fire pit, all within reach of Chesapeake’s scenic waterways, local festivals, and easy access to Virginia’s beaches and mountains-your ideal lifestyle begins here. Photos and renderings are from builder's library, actual finishes and features may vary.

321 Riverview Road, South Chesapeake

$665,900

5 Beds ⋅ 3.1 Baths ⋅ 10659608 MLS

Joseph’s Meadow (MODEL GPS 369 Scotland Ln. Chesapeake) Nestled in Greenbrier come visit the newest community by renowned local builder. Lily Cottage C welcomes you w/ a full front porch, airy 10-foot ceilings & HW floors entire first floor. Designed for entertaining, the open-concept layout seamlessly connects the living room, dining area, & stunning chef’s kitchen featuring a 9-foot quartz island, custom hood, & HUGE walk-in pantry. Mudroom and powder room are conveniently tucked away by 2-car garage. Custom stair detail mid level with loft, 2 bedrooms + full bath -dual sinks, private tub/shower & water closet. HUGE 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. Third flr features 2 BR, Full bath, 2 walk in Attic storage! Easy living w/professionally managed grounds low-maintenance living, making easy living a reality!

389 Scotland Lane, South Chesapeake

MM Bellhaven-Multi-Gen, South Chesapeake

$800,000

5 Beds ⋅ 3.1 Baths ⋅ 10659297 MLS

Master Model- To Be Built- Bellhaven Multi-Gen by Wetherington Homes. This thoughtfully desinged floor plan offers flexible living spaces to suit a variety of needs. A private suite includes its own living area, optional kitchenette, private bath, washer/dryer hookup, and dedicated garage bay- ideal for extended stays, guests, or additional workspace. The open-concept main living area features modern finishes and functional design thoughout. Located in the desirable Hickory area of Southern Chesapeake with convenient access to shopping, dining, and major roadways. Contact our Sales Counselor today to schedule your appointment or for additional information.

MM Bellhaven-Multi-Gen, South Chesapeake

$745,425

5 Beds ⋅ 3.1 Baths ⋅ 10659276 MLS

10,000 square foot lot, ready early 2027, still time to customize. The Hawthorne floor plan offers flexibility & spacious living, making it the largest & most adaptable 2-story home at Crestfield. With an impressive 3,089 square feet, this open-concept home offers 5 bedrooms, including dual owner’s suites & 3.5 baths. The kitchen features quartz countertops, stainless steel appliances, and a generously sized island for seating & casual dining. Both levels boast 9-foot ceilings, enhancing the sense of space & light throughout the home. The front porch invites you to relax & enjoy the neighborhood, & the 2-car garage provides ample storage and parking. Fenced yard. Seller to pay up to $10K closing cost assistance when preferred lender is used for financing, see agent for details. Buyer must register agent on or before first visit or first substantial communication with listing agent and Agent must accompany Buyer on 1st visit, see Listing Agent for details. Photos & Video are of previously built home for illustrative purposes, finishes & upgrades will vary in home to be built.

2039 Charwood Drive, South Chesapeake

$765,425

5 Beds ⋅ 3.1 Baths ⋅ 10659274 MLS

Location backing mature tree line, ready early 2027, still time to customize. The Hawthorne floor plan offers flexibility & spacious living, making it the largest & most adaptable 2-story home at Crestfield. With an impressive 3,089 square feet, this open-concept home offers 5 bedrooms, including dual owner’s suites & 3.5 baths. The kitchen features quartz countertops, stainless steel appliances, and a generously sized island for seating & casual dining. Both levels boast 9-foot ceilings, enhancing the sense of space & light throughout the home. The front porch invites you to relax & enjoy the neighborhood, & the 2-car garage provides ample storage and parking. Fenced yard. Seller to pay up to $10K closing cost assistance when preferred lender is used for financing, see agent for details. Buyer must register agent on or before first visit or first substantial communication with listing agent and Agent must accompany Buyer on 1st visit, see Listing Agent for details. Photos & Video are of previously built home for illustrative purposes, finishes & upgrades will vary in home to be built.

2032 Charwood Drive, South Chesapeake

$650,000

5 Beds ⋅ 3 Baths ⋅ 10659213 MLS

Classic brick charm and generous living space make this 5-bedroom, 3-bath home a standout in the sought-after Great Bridge school district. Nestled on a quiet cul-de-sac, this well-maintained home sits on a large lot with room to spread out inside and out. Recent updates include new carpet, a new deck, and fresh paint, adding to its bright, welcoming feel. Spacious living areas and a functional layout accommodate everyday living and entertaining, while the deck offers a place for gatherings or quiet evenings outdoors. Move-in ready and conveniently located, come see the space and possibilities for yourself!

145 Sinclair Lane, South Chesapeake

$425,000

5 Beds ⋅ 2.1 Baths ⋅ 10659140 MLS

Move-in ready home in the Deep Creek area featuring a new roof, new lower-level windows, new flooring, fresh interior paint, and a new privacy fence. The kitchen has been updated with new countertops and stainless-steel appliances. Bathrooms feature new vanities and light fixtures. Conveniently located near shopping, dining, and major commuter routes.

2725 Spinners Way, South Chesapeake

2519 Deal's Creek Court, South Chesapeake

$590,000

5 Beds ⋅ 2.1 Baths ⋅ 10659107 MLS

Welcome to your Dream Home! This stunning masterpiec, less than a year old, blends modern luxury with everyday functionality. Boasting spacious bedrooms and a 5th flex room, this home is designed to accommodate growing families, multigenerational living, and those that love to entertain. From the moment you step through the front door, you are greeted by an abundance of natural light and an expansive open concept layout. Retreat upstairs to the primary suite, a true sanctuary, complete with a large primary bathroom and 2 walk in closets. Outside the property offers wonderful curb appeal and a manageable yard ready for your personal touch. Very convenient to interstates, schools, and shopping. Make this home yours for the holidays!

2519 Deal's Creek Court, South Chesapeake

$558,000

5 Beds ⋅ 3 Baths ⋅ 10658985 MLS

Welcome to the kind of home that feels good the moment you enter. Set on just over 2 peaceful acres, this 5-bed, 3-bath home offers the perfect blend of space, comfort, and modern style. Sunlight pours through the windows, filling every room with warmth, while the open layout creates an easy flow for everyday living and gathering with the people you love. The home features two spacious primary suites, one located on the first level, both with private baths and large closets, making it ideal for guests, or multigenerational living. You'll also love the luxury vinyl plank flooring, granite countertops, stainless steel appliances, and the beautiful laundry room! The backyard is just as inviting. Whether you're roasting marshmallows around the fire pit, spending summer afternoons in the saltwater pool, or simply enjoying the quiet views with your morning coffee, the backyard feels like your own private escape. Peaceful, welcoming, and full of room to grow! *One year Choice home warranty

1108 Shell Road, South Chesapeake

$867,136

5 Beds ⋅ 4.1 Baths ⋅ 10658871 MLS

The Sterling Multi-Gen by Wetherington Homes at Riverview Landing. Discover striking Craftsman architecture, elevated finishes, and thoughtfully designed living spaces. This impressive 5-bedroom, 4.5-bath home offers exceptional versatility, including a multi-generational layout ideal for extended stays, private guest accommodations, or everyday living. Enjoy a beautifully appointed kitchen, spacious gathering areas, and room to spread out while maintaining comfort and privacy. Located in desirable Southern Chesapeake with access to the sought-after Hickory school district, this home blends style, function, and convenience. A rare quick-delivery opportunity with anticipated January 2027 completion lets you plan your next move sooner! Contact our Sales Counselor today for details!

904 Intracoastal Way, South Chesapeake

$674,900

5 Beds ⋅ 2.1 Baths ⋅ 10658800 MLS

Convenient location. 20 min to Downtown Norfolk. 35 min to NAS Oceana, Dam Neck & beaches. 20 min to Norfolk Int Airport. Over 10 grocery stores in a 5 mile radius. 5 min to Hickory H.S., 1 of the BEST in Hampton Roads. Easy access to Chesapeake Bypass, I-64, I-264, & I-464. This property is a gardener's dream sequenced for near year round color. Back yard oasis includes a hot tub, goldfish pond and six foot privacy fence. Two patios are connected by a master-crafted paver walk-way. Oversized garden shed helps keep garage clutter free. In ground sprinkler system fed by well water to keep watering cost low. Two outdoor water taps fed by the well & two additional taps fed by city water. Tank-less water heater provides endless hot water. The oversized Primary Bedroom includes two walk in closets. One large walk-in closet features two side cubby units for storage. The other walk-in closet is medium sized with plenty of storage space. Washer & dryer are on the second floor for convenience to bedrooms. Some photos are AI-virtually staged.

707 River Gate Court, South Chesapeake

$629,900

5 Beds ⋅ 3.1 Baths ⋅ 10658802 MLS

If you've been searching for a spacious, move-in-ready home with a private in-law suite on a large lot in the heart of Chesapeake, your search is over! This one-of-a-kind property offers the blend of comfort, flexibility, and space. The traditional in-law suite features its own multiple entrances, full kitchen, living room with a cozy gas fireplace, recently remodeled bathroom, bedroom, and dedicated laundry area—use for multi-generational living or extended guests. Step outside to a large backyard for relaxing or entertaining, complete with a recently built gazebo with electricity and a storage shed for all your gardening and outdoor needs. Located in a neighborhood with sought-after schools, you'll enjoy convenient access to shopping, dining, parks, and more. Don't miss this rare opportunity to make this exceptional Chesapeake home yours!

1307 Channing Way, South Chesapeake

$500,000

5 Beds ⋅ 3 Baths ⋅ 10658716 MLS

Spacious brick rancher offering 5 bedrooms and 3 full baths with an abundance of living space and approximately $250,000 in improvements over the past 13 years! The home features a living room, formal dining room, and inviting family room with fireplace. The kitchen offers granite countertops and plenty of cabinet space. The primary suite includes a private bath and walk-in closet, while the finished room over the garage provides additional flexibility for a home office, recreation room, or guest space. Enjoy outdoor living on the large covered deck overlooking the above-ground saltwater pool and fenced backyard. Additional highlights include an oversized attached 1-car garage and an oversized detached 2-car garage with workshop, valued at approximately $60,000. With generous space, extensive improvements, and exceptional garage and workshop space, this property offers plenty to appreciate!

461 Gloria Drive, South Chesapeake

$345,000

5 Beds ⋅ 2 Baths ⋅ 10658681 MLS

Discover the potential in this 5-bedroom, 2- bathroom ranch nested on New Mill Creek. This home features tons of updates throughout, providing a great head start while leaving room for your personal cosmetic touches. Head outback to the large lot, where natural scenery creates a peaceful backdrop for everyday living. Flood insurance is required.

1753 Burson Drive, South Chesapeake

$735,000

5 Beds ⋅ 3 Baths ⋅ 10658619 MLS

Brick on the outside, a serious refresh on the inside, and pond views out back. Located in Chesapeake’s Etheridge Lakes, this home has plenty worth talking about, starting with fresh paint throughout, new flooring, new kitchen countertops, painted kitchen cabinets, and updated light fixtures. The main level gives each space a purpose without feeling divided up. Natural light fills the family room, where a gas fireplace anchors the space. There’s a separate front study, a formal dining room, and a sunlit breakfast nook. The open kitchen offers plenty of counter space and cabinetry, plus a walk-in pantry big enough to deserve a mention of its own. A first-floor bedroom and full bath add flexibility to the layout. Upstairs, the primary suite has room to spare, along with a generous walk-in closet and private bath with dual sinks. The additional bedrooms are oversized, too. An attached garage, a roof approximately five years old, and a water heater approximately seven years old add to the practical side of the home. But the view out back is what stays with you. The rear deck overlooks the pond, giving you a beautiful place to start the morning or wind down at the end of the day. It’s the combination of refreshed interiors, genuinely usable space, and that water view that makes this one stand out. Arrange a showing to take it all in.

804 Catrina Lane, South Chesapeake

$765,682

5 Beds ⋅ 4 Baths ⋅ 10658443 MLS

The Macon Model at Riverview Landing by Wetherington Homes. Buyers may select their lot and personalize available design options. The community offers eight thoughtfully designed floor plans along with multiple exterior elevations that highlight architectural detail and curb appeal. This plan features five bedrooms, four bathrooms, a loft, and a first-floor bedroom with a full bath. The chef-inspired kitchen includes upscale finishes, a large island, and a Butler's pantry. Designed to balance functionality and craftsmanship, this home offers modern conveniences with thoughtful design throughout. Contact us today for additional information, to join the VIP interest list, and to schedule an appointment. Discover the opportunity to build in this new community with convenient access to everyday amenities!

308 Riverview Road, South Chesapeake

$725,000

5 Beds ⋅ 3 Baths ⋅ 10658407 MLS

MM Ashbee at Riverview Landing - To Be Built. The Ashbee is a 5-bedroom home with a first-floor Owner’s Suite, four bedrooms and a loft upstairs. Open-concept kitchen with large island, high-end finishes, double ovens, pantry, and plenty of counter space. Features include first and second-floor laundry (or option to convert upstairs laundry to a full bath), mudroom, and optional rear covered porch. Standard features and design options available. Convenient to shopping, dining, healthcare, and major roadways

MM Ashbee, South Chesapeake

$419,900

5 Beds ⋅ 2.1 Baths ⋅ 10658338 MLS

One of a Kind in Geneva Shores! Prepare to be surprised by just how much space this unique home has to offer! The owner added a custom-designed second floor, creating additional living space and flexible options to accommodate your needs through the years and generations to come. Full of character and nostalgic charm, this cozy home is tucked alongside a canal that leads to deep-water access on the Elizabeth River. Whether you dream of kayaking, cruising in your Jon boat, fishing close to home, or simply enjoying the peaceful waterfront surroundings, this property offers a wonderful opportunity to embrace life on the water. And there’s even more to love! Just one street away, you’ll find the Elizabeth River Park VDWR Boat Ramp, providing convenient access for your boating adventures. The home has central vacuum. A unique home, a waterfront setting, and endless possibilities! This is an estate sale....All of the furniture and accessories will be removed by November. Property is being sold AS IS HOME INSPECTION IS FOR INFORMATIONAL PURPOSES ONLY

2013 Athens Court, South Chesapeake

$565,000

5 Beds ⋅ 3 Baths ⋅ 10658340 MLS

Gorgeous, like-new home built in 2016 offering over 2,400 sq ft of living space. A first-floor bedroom and full bath make this layout great for guests, a home office, or an in-law suite.The gourmet kitchen is made for entertaining, featuring granite countertops, stainless steel appliances, and a gas range. Step outside to a fenced backyard backing to peaceful wooded views; great for morning coffee or quiet evenings.With modern finishes throughout and minimal need for updates, this home is truly move-in ready and packed with value!

1201 Richwood Avenue, 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

$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

$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

$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

$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

$1,199,000

5 Beds ⋅ 3.1 Baths ⋅ 10657504 MLS

Discover a rare opportunity to enjoy country living on 28.18 private acres in Southern Chesapeake! This distinctive property combines a spacious, updated 5-bedroom, 3.5-bath home with approximately 18 acres of farmland, wooded recreational areas and exceptional space for hobbies, equipment and outdoor living. Located in Chesapeake’s sought-after Hickory area, the 3,714 sq ft home offers light-filled living spaces, thoughtful updates and a butler’s pantry with granite countertop, cabinetry and extra storage. TWO primary suites, one on each floor, offer privacy and flexibility. The refreshed first-floor suite features updated flooring, paint, lighting and hardware. Upstairs, the spa-inspired primary bath impresses with an oversized wet room, rainfall shower, body jets, two-person soaking tub, porcelain tile and marble mosaic. All 3.5 bathrooms have been updated! Outside, unwind on the nearly wraparound porch or entertain on the 20x40 composite deck with outdoor granite countertop setup. Enjoy a fire pit, playground, fruit trees, grapevines, deer and turkey hunting, and private shooting and archery areas. A detached 4-car garage offers room for vehicles and equipment, while the 20x30 workshop includes concrete flooring, lighting and its own electrical panel. Improvements include 33 solar panels, a Level 2 EV charger, electrical upgrades, crawlspace encapsulation, updated HVAC and a private well. Rare acreage, recreation and an extensively improved home, all in Hickory! Up to $20,000 in seller assistance toward eligible buyer closing costs and/or interest-rate buydown may be considered, subject to mutually acceptable terms and lender approval. See Feature & Upgrade Sheet for more details. Some listing photos have been virtually staged using AI.

509 Ballahack Road, South Chesapeake

$699,900

5 Beds ⋅ 3.1 Baths ⋅ 10657221 MLS

Private upstairs living quarters, a wooded backyard, & a flexible multigenerational layout define this inviting ranch-style home. The suite over the garage includes a bedroom, full bath, great RM, & large walk-in attic, offering a comfortable retreat with added independence for guests or extended household living. On the main level, the gourmet kitchen features abundant granite counter space, generous cabinetry, a pantry, S/S appliances, & a gas range. Vaulted ceilings enhance the bright, open great RM. The primary suite offers a spa-inspired bath with soaking tub, oversized tiled walk-in shower, double vanity, & spacious walk-in closet. Two additional bedrooms share a full bath. Relax on the screened porch & enjoy exceptional privacy surrounded by the wooded backyard. Designed for comfort, connection, & flexibility, this home adapts beautifully to the way you live.

1421 Gemstone Lane, South Chesapeake

$948,000

5 Beds ⋅ 3 Baths ⋅ 10657075 MLS

Welcome to Woodford Estates! This stunning home is like new construction built in 2025, loaded with upgrades & thoughtful details throughout. The gorgeous open-concept living, kitchen, and dining area features an extended kitchen with quartz countertops that flow seamlessly into the backsplash, additional cabinetry, and beautiful tilework. The spacious living room boasts a fireplace flanked by custom built-ins. A first-floor bedroom and beautifully appointed full bathroom offer added flexibility. Upstairs, the impressive primary suite features a luxurious five-piece bath and an enormous walk-in closet with shelving. Three additional generously sized bedrooms and a full bathroom with en-suite access from one bedroom complete the second floor. Outside, enjoy the peaceful, fully fenced backyard featuring a spacious stamped concrete patio, built-in fire pit, and tranquil wooded views. Great for entertaining or relaxing in your own private retreat! Desirable schools, easy access to the highway & absolutely turn key- must see this one today!

203 Hessian Loop, South Chesapeake

$735,000

5 Beds ⋅ 2.1 Baths ⋅ 10656950 MLS

Why wait on new construction when so much of the work here is already done? Set on three private acres in Grassfield, this modern farmhouse has been completely reworked inside and out, and a detached garage plus whole-house filtration system will both be installed prior to closing. The kitchen centers the main living space with an oversized island and bar, white cabinetry, and a clean, current finish. The renovation continues throughout with new windows, upgraded Hardie Plank siding, a new roof, new water heater, and two new heat pumps with dual-zone HVAC. The primary suite features private porch access, dual closets, and a spa-style bath with a floor-to-ceiling marble-tiled shower. Mature trees and a classic brick fireplace add character against the newer finishes and major system updates. With three acres, a full renovation, major systems already replaced, and a detached garage being completed before closing, this is the kind of property that gives you the space, finish, and function buyers rarely find all in one place.

1629 Shillelagh Road, South Chesapeake

$599,000

5 Beds ⋅ 2.1 Baths ⋅ 10655447 MLS

Welcome to this beautifully updated 4-bedroom, 2.5-bath home with TWO additional flex rooms, offering 2,731 square feet of living space in the sought-after Brooks Run community! Featuring a timeless combination of brick and vinyl siding, this meticulously maintained home delivers exceptional curb appeal with professionally landscaped grounds and a host of impressive upgrades. Come tour the inside and discover fresh paint, new carpeting, and luxury vinyl plank flooring throughout the first floor. The spacious kitchen features a gas cooktop, upgraded appliances, tile backsplash, and abundant natural light. An extensive trim package adds architectural character throughout the home. Upstairs, the oversized primary suite offers a custom tile shower and luxurious soaking tub. Two versatile flex rooms provide endless possibilities for a home office, media room, playroom, or additional living space. Outside, enjoy beautifully maintained landscaping, added concrete, and a spacious backyard complete with a hot tub. The attractive brick-front exterior and attached 3-car garage complete this exceptional property. Outdoor enthusiasts will appreciate the remarkable location through your backyard gate and access the Great Dismal Swamp trail system, including the Portsmouth Trailhead and Black Bear Trail! Enjoy nature hiking, wildlife viewing, and seasonal hunting where permitted and subject to applicable regulations. A rare opportunity to enjoy a beautifully upgraded home with the natural beauty of the Great Dismal Swamp practically in your backyard. Appliance package conveys!

3629 Kathys Way, South Chesapeake

$724,777

5 Beds ⋅ 3.1 Baths ⋅ 10656577 MLS

The builder will help with the payments by providing a two one buy down. See features sheet & survey attached — you’ll be amazed by this NEW custom home by Overholt Contracting (40+ yrs)! Must see now: modern floorplan with 2 spacious primary suites (or use one as a game room), 4 large bedrooms, first-floor home office, high-end kitchen & baths with quartz, freestanding tub + tiled shower, smart-home Wi-Fi, and full landscaping with sod. Sited on almost 1/2 acre in Hickory (Chesapeake) on city/county septic & water — NO HOA, additional buildings allowed, room for pool, boat or RV. James Hardie siding, carriage garage door with glass, brushed concrete patio. Closing cost assistance available with preferred lender Wes Flowers, Southern Trust. Also see something you would love to have but it’s not here. Contact me and my builder will have his design team work on it. He is easy going and ready to make your new home all about you!!! You wont find another build of this quality at this amazing price.

343 Ewell Lane, South Chesapeake

$845,000

5 Beds ⋅ 4.1 Baths ⋅ 10656573 MLS

The Macon Multi-Gen at Riverview Landing - Master Model Listing by Wetherington Homes. Buyers may select their lot and personalize available design options. Thoughtfully designed with approximately 3,535 sq. ft. of living space and a 3-car garage, the MM Macon Multi-Gen offers exceptional flexibility for today’s lifestyles. This home features a private multi-generational suite complete with a living room, bedroom, full bath, and washer/dryer hookup, with an optional kitchenette for added convenience. Ideal for extended stays, guests, or multi-generational living. Enjoy a convenient location close to schools, shopping, restaurants, and more! Contact our Sales Counselor today to learn more.

MM Macon-Multi-Gen, South Chesapeake

$669,000

5 Beds ⋅ 3 Baths ⋅ 10656320 MLS

Beautifully cared for and truly move in ready, this nearly 3,000 sf home sits at the end of a quiet cul de sac with exceptional outdoor living space. Built in 2017 and lovingly maintained, it offers 5 bedrooms, 3 full baths and plenty of space for everyone. The open living room, kitchen with gas range and eat in area flow effortlessly into a beautiful formal dining room and a flex bonus space perfect for an office, den or playroom. A first floor bedroom with full bath is perfect for hosting guests or multigenerational living. Upstairs, find a spacious primary suite, 3 additional bedrooms, full bath and laundry. A benched drop zone sits off the side load garage with extended concrete. Outside find a standout backyard – fenced in, mature landscaping, covered patio, custom stamped concrete areas, above ground pool with deck, playset and trampoline – ideal for relaxing, entertaining and making memories. Immaculate and in sought-after school district. The school bus stop is conveniently located in the cul de sac for this home. Seller is willing to remove trampoline and closet built-ins in bedroom at buyer's request. Seller will provide 1 year home warranty with Choice in the amount of $660.00. This home is a must see!

920 Covenant Way, South Chesapeake

$589,900

5 Beds ⋅ 2.1 Baths ⋅ 10656498 MLS

Discover the perfect blend of comfort, style, and convenience in this spacious, beautifully updated 2-story home tucked away in an intimate neighborhood of approximately 33 homes. Featuring 5 bedrooms, 2.5 bathrooms, and a desirable first-floor primary suite with stunning cathedral ceilings, this home offers a thoughtful layout designed to fit your lifestyle. Enjoy the flexibility of a spacious loft, ideal for a home office, media room, or additional living space. Step outside to relax or entertain on the composite deck, and enjoy added peace of mind with a whole-home backup generator. Situated on a desirable corner lot, this home offers the space and functionality you’ve been looking for, along with the added benefit of no flood insurance required. Conveniently located just a short drive from Greenbrier’s shopping, dining, and entertainment, with easy access to major highways and the natural beauty of Chesapeake Arboretum, this home makes everyday living a breeze. Space, style, convenience, and peace of mind—all in one exceptional home. Don’t miss your opportunity to make it yours!

513 Telfyan Drive, South Chesapeake

$675,000

5 Beds ⋅ 3.1 Baths ⋅ 10656044 MLS

Welcome in to this beautiful Great Bridge home! This spacious 5 bedroom, 3.5 bath home offers comfortable living in a neighborhood where location and lifestyle come together. Enjoy being just a short distance from the community pool, perfect for summer afternoons! Inside, the open kitchen flows seamlessly into the living area and features granite countertops, stainless appliances, a center island, and pantry. The cozy living room adds character with wood beams and a fireplace. The spacious primary suite offers a relaxing retreat with dual sinks, a soaking tub, and separate custom tile shower. Outside, enjoy a screened porch and concrete patio with fire pit that are perfect for entertaining or unwinding. Come see this one today!

516 Ashforth Way, South Chesapeake

$686,380

5 Beds ⋅ 3 Baths ⋅ 10656477 MLS

The Lehigh single-family home combines smart design with light-filled spaces. Enter the inviting foyer, where versatile flex space can be used as a playroom, living room or office. The gourmet kitchen boasts a large island and pantry and connects to the dining and family room. Off the 2-car garage, a family entry controls clutter and leads to a quiet study/bedroom. Upstairs, a loft is an ideal entertaining spot outside 3 spacious bedrooms and a double vanity bath. The luxurious owner's suite offers a cozy getaway with large closets and private bathroom. You'll love The Lehigh.

213 Gertrude Street, South Chesapeake

3342 Martin Johnson Road, South Chesapeake

$1,650,000

5 Beds ⋅ 3.2 Baths ⋅ 10656180 MLS

Quiet Luxury. Architectural Artistry. This Custom Built Estate was designed not simply to be lived in, but to be experienced on 4 acres, 5,900 sqft (plus add'l 980 ROG). The dramatic, soaring ceilings & windows throughout a 2-story family rm w/stone fireplace, along w/every custom architectural detail make a statement of true Luxury. From the picturesque curb appeal to first floor Primary Suite & your own private spa, a cedar-lined wellness retreat w/hot tub. The expansive fl plan provides flexibility for formal gathering & relaxed everyday living. This home was thoughtfully designed, w/ 4 add'l spacious bedrms, generous living & entertainment areas, abundant nat'l light & craftsmanship throughout. New 6 burner-gas Wolf range in large kitchen, Trex board decking outside, endless possibilities to entertain & peace/privacy. An inground pool, pool house, pergola & plenty of open space. Large ROG is ready for you to make it your own movie/game room! Ask your agent for feature sheet!

3342 Martin Johnson Road, South Chesapeake

$650,000

5 Beds ⋅ 2.1 Baths ⋅ 10656054 MLS

Seller is Open to BUYING DOWN the buyers interest rate. Step inside to a huge, welcoming two-story foyer that sets the tone for this spacious, move-in-ready home. The kitchen steals the show, opening directly to the family room and featuring a huge center island with seating, built-in desk, butler’s pantry, oversized pantry, abundant cabinetry, under-cabinet lighting and a generous eat-in area—perfect for everyday living and entertaining. Just off the kitchen, a wood deck plus a concrete patio provide plenty of outdoor space for grilling, gathering and entertaining. Freshly and professionally painted with new carpet, this home also offers a 2024 roof and a clear termite and moisture letter. The family room features a gas fireplace, and every bedroom already has a ceiling fan. A Peloton bike is included, making it easy to fit a workout into your day without leaving home. Double doors welcome you into the huge primary suite with a tray ceiling and an amazing walk-in closet that wraps around the corner for even more storage than you expect! The ensuite bath features a jetted tub, separate shower and dual sinks. The hall bath also offers a soaker tub and dual vanities. Additional features include a gas water heater, dual-zone HVAC and Nest thermostat. Tucked into a cul-de-sac and conveniently located near Greenbrier shopping, dining, entertainment and interstate access. Get your showing scheduled today.

1500 Coker Place, South Chesapeake

$640,000

5 Beds ⋅ 2.1 Baths ⋅ 10655665 MLS

Buyer may receive a lender credit of up to 1.25% of the loan amount toward eligible closing costs with the use of the preferred lender. Great Bridge schools, no HOA, and a floor plan that gives you room to make it your own, 1103 Madison Lynn Way checks some hard-to-find boxes in Chesapeake. Located in Hanbury Manor, this spacious home offers approximately 2,557 square feet with four bedrooms upstairs plus a versatile fifth room on the first floor that can serve as a bedroom, home office, playroom, or flex space. The main level features an open layout with spacious living and dining areas and an updated kitchen with quartz countertops, stainless steel appliances, plenty of cabinetry, and LVP flooring. Upstairs, all four bedrooms are conveniently located together, including a spacious primary suite with cathedral ceilings, a walk-in closet, soaking tub, and separate shower. A dedicated upstairs laundry room with a utility sink adds even more convenience. Outside, enjoy a fully fenced backyard with a patio and storage shed, plus an attached two-car garage. Hanbury Manor offers an established neighborhood setting without the restrictions of an HOA, with quick access to Great Bridge schools, restaurants, shopping, interstates, and an easy commute to military bases throughout Hampton Roads. Space, flexibility, no HOA, and a Great Bridge location, this is one you’ll want to see.

1103 Madison Lynn Way, South Chesapeake

1153 Edinburgh Parkway, South Chesapeake

$725,000

5 Beds ⋅ 3 Baths ⋅ 10655913 MLS

Cottage charm on the outside, showstopper on the inside, and Stephen Alexander craftsmanship in every detail! This Caramel Cottage in Great Bridge delivers the builder's signature molding and trim, soaring 10-foot ceilings, and rich hardwood floors from the moment you step into the foyer. The highly flexible floor plan features a sought-after first-floor bedroom and full bath, or a dedicated office/study and a formal dining area ready for holiday dinners and special occasions. The living room is anchored by a gas fireplace framed in custom built-ins, creating a warm and inviting gathering space that flows easily into the heart of the home. The kitchen is the true showpiece, with 42" white cabinetry that rises to meet those tall ceilings, an oversized island with plenty of room to gather, a gas range, stainless appliances, and a walk-in pantry for effortless organization. The breakfast area adds a relaxed spot for everyday meals, making cooking and entertaining easy. Upstairs, the primary suite is a private retreat with a tiled shower, jetted soaking tub, dual vanities, and a spacious walk-in closet. A finished room over the garage offers even more flexibility as a media room, hobby space, or bonus room, and brand-new carpet is already in place! And then there's the porch! The three-season Eze-Breeze enclosure is one of the home's best features, with sliding vinyl panels that open wide to let the breeze in and close up to keep rain, wind, and bugs out, so porch season doesn't end when summer does. From there, step down to the large paver patio in a privacy-fenced backyard, a relaxing setting for morning coffee, evening gatherings, or simply unwinding outdoors. Thoughtful details continue throughout, including zoned heating and cooling, fiber cement siding, a walk-in attic for extra storage, a utility room, and an attached two-car garage with additional driveway parking. From the curb to the craftsmanship, every inch of this home was built with intention. This is Great Living in Great Bridge!

1153 Edinburgh Parkway, South Chesapeake

$740,000

5 Beds ⋅ 3 Baths ⋅ 10655942 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, South Chesapeake

$699,990

5 Beds ⋅ 3 Baths ⋅ 10655662 MLS

The Lehigh single-family home combines smart design with light-filled spaces. Enter the inviting foyer, where versatile flex space can be used as a playroom, living room or office. The gourmet kitchen boasts a large island and pantry and connects to the dining and family room. Off the 2-car garage, a family entry controls clutter and leads to a quiet study/bedroom. Upstairs, a loft is an ideal entertaining spot outside 3 spacious bedrooms and a double vanity bath. The luxurious owner's suite offers a cozy getaway with large closets and private bathroom. You'll love The Lehigh.

205 Gertrude Street, South Chesapeake

$605,000

5 Beds ⋅ 3.1 Baths ⋅ 10655526 MLS

Beautifully maintained 5-bedroom, 3½-bath home situated on nearly half an acre, featuring generously sized rooms, beautifully landscaped grounds, and tasteful brick garden beds filled with year-round evergreens. The inviting interior offers a sunroom, spacious eat-in kitchen, formal dining room, and formal living room, providing plenty of room for everyday living as well as entertaining family and friends. Step outside to the huge backyard, where you'll find plenty of space to gather and enjoy the outdoors. A charming pergola. Seller offering closing cost assistance with full price offer

3240 Joplin Lane, South Chesapeake

$720,000

5 Beds ⋅ 3 Baths ⋅ 10655465 MLS

Model Home to Be Built - James II Model at Riverview Landing by Wetherington Homes. This thoughtfully designed floor plan offers an Owner's Suite, two additional bedrooms, and a utility room conveniently located on the first floor. Buyers may select their lot and personalize available design options. The home includes a variety of well-appointed features designed to support modern living. The community offers eight floor plan options along with multiple exterior elevations that highlight architectural detail and curb appeal. Contact us today for additional information, to join the VIP interest list, and to schedule an appointment. Discover the opportunity to build in this thriving new community in Chesapeake!

MM James 2, South Chesapeake

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