Chesapeake, VA Real Estate | Chesapeake, VA 5 Bedroom Properties for Sale

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

$489,900

5 Beds ⋅ 3 Baths ⋅ 10659168 MLS

BRAND-NEW CONSTRUCTION IN AN ESTABLISHED CHESAPEAKE NEIGHBORHOOD! Welcome to 4215 Surf Avenue, where the benefits of new construction meet the charm of an established neighborhood. Offering approximately 2,550 square feet, 5 bedrooms and 3 full baths, this thoughtfully designed home provides space, flexibility, and an open floor plan that works for a variety of lifestyles. One of the standout features is the oversized first-floor bedroom with direct access to a full bath that also opens to the hallway—creating an excellent setup for guests, multigenerational living, an in-law suite, or anyone looking for convenient first-floor accommodations. Upstairs, you'll find the home's primary suite, along with additional generously sized bedrooms and plenty of room for everyone to spread out. Come make 4215 Surf Avenue home!

4215 Surf Avenue, Central Chesapeake

2519 Deal's Creek Court, South Chesapeake

$590,000

5 Beds ⋅ 2.1 Baths ⋅ 10659107 MLS

Thoughtfully designed and expertly built by local, award-winning builders, this home is more than just a house — it's a lifestyle upgrade. Featuring an open floor plan, elegant finishes, and attention to detail, this home is built for relaxed everyday living. High ceilings create a bright, airy atmosphere while the thoughtfully chosen LVP flooring throughout the home adds timeless beauty, durability, and ease of maintenance — ideal for busy households. The kitchen is truly a showstopper, featuring custom-designed cabinetry, granite countertops and stainless steel appliances. Upstairs, you’ll find a spacious primary suite with 2 walk in closets and a spa-like primary bath. Spacious secondary bedrooms and a 5th flex room! 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

$595,000

5 Beds ⋅ 3 Baths ⋅ 10658855 MLS

Welcome to this amazing all-brick home in sought after Western Branch! This home offers timeless charm and modern luxury. The heart of the home is a beautifully updated kitchen(new 2024) boasting Fantasy Brown granite countertops, white shaker cabinets, ceramic tile backsplash, a large center island, under cabinet lighting and more. Unwind in the inviting family room by the gorgeous brick fireplace, flanked by built-in glass-door lighted cabinets. Enjoy dual staircases, updated bathrooms, and whole-house water filtration and softening systems, a Texas sized primary bedroom, and the 5th bedroom could be media/game room. Head outside to your private oasis complete with an oversized Trex deck w/a retractable awning, hot tub, a charming trellis-covered patio, firepit area and a detached storage shed with electricity. New roof(2022), tankless water heater(2023), vapor barrier(2026) and so much more! Don't miss this incredible find! Some rooms virtually staged.

3422 Anita Circle, West 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

$550,000

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

$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

$575,000

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

$435,000

5 Beds ⋅ 2 Baths ⋅ 10658234 MLS

Welcome home to this beautifully renovated 5-bedroom, 2-bath ranch offering nearly 2,000 sq.ft. of thoughtfully designed living space! The stunning eat-in kitchen is the heart of the home,featuring new cabinetry, quartz countertops, an oversized island, stainless steel appliances & acozy fireplace. Fresh paint, luxury vinyl plank flooring, plush carpeting & tastefully updatedbathrooms add style and comfort throughout. Enjoy relaxing on the charming front porch orentertaining on the spacious rear deck. An attached one-car garage adds everydayconvenience, while all major home systems have been serviced & maintained. Ideally situatedin a desirable neighborhood with convenient access to shopping, dining, entertainment & majorinterstates. This beautifully refreshed home is ready to welcome its new owners. Schedule yourprivate tour today!

4116 Emberhill Lane, West Chesapeake

$676,439

5 Beds ⋅ 4.1 Baths ⋅ 10658190 MLS

Welcome home to this stunning brand 2 story home, designed with modern style, comfort, and functionality. Offering 5 spacious BDRs, 4.5 BTHS, this home features an open-concept floor plan that's perfect for both daily living & entertaining. Features of our gourmet kitchen are upgraded quartz countertops, upgraded appliances, abundant cabinetry, & a large island that overlooks the spacious living area. LVP flooring flows throughout the first floor, while 9-foot ceilings & elegant crown molding adding sophisticated touch. A first-floor BR with full bath provides the perfect space for guests, or a private home office. Upstairs, you'll find generously sized bedrooms, with walk in closets. and a loft offering endless possibilities with additional living space. Exceptional community amenities include a beautiful clubhouse, community pool, playgrounds, a covered pavilion with picnic areas, and outdoor recreation spaces perfect for gathering with family and friends. Surrounded by natural beauty, this community offers a peaceful setting while remaining conveniently close to shopping, dining and highways. Don't miss the opportunity to own a beautiful home in one of the area's most desirable new-home communities.

1937 Paw Paw Place, West 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

$450,000

5 Beds ⋅ 3 Baths ⋅ 10658123 MLS

Welcome home to this spacious 5-bedroom, 3-full-bath home in Chesapeake, offering a wonderful combination of comfort, functionality, and convenience. Built in 2006, this home features a versatile floor plan with a first-floor bedroom and an accessible full bathroom, providing flexibility for guests and multigenerational living. Fresh carpet and paint throughout give the home a refreshed feel. The HVAC system was replaced in 2017. Outside you can enjoy the spacious, fully fenced backyard, featuring a double gate that allows vehicle access. Conveniently located near area military bases, this home offers an appealing location for military personnel, commuters, and anyone looking to enjoy all that Chesapeake has to offer!

1403 Elder Avenue, Central 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

$575,000

5 Beds ⋅ 3.1 Baths ⋅ 10657811 MLS

Soaring cathedral ceilings, an updated kitchen, and a first-floor suite that feels almost like its own wing give this Waterstone home plenty to remember. The main living area feels open and connected, with a gas fireplace creating a natural focal point and cathedral ceilings adding volume overhead. The kitchen has been refreshed with painted white cabinetry, dark gray quartz countertops, a tile backsplash, black finishes, and newer appliances for a clean, current look. One of the home’s biggest standouts is the expansive first-floor suite, complete with private exterior access, a large closet, and its own sitting area. The scale and separation make it feel more like a private retreat than just another room. LVP flooring, newer carpet, and updated windows continue throughout the home. Above the two-car garage, another spacious living area with cathedral ceilings and LVP flooring adds even more flexibility for an office, media room, playroom, or additional living space. A partially encapsulated crawlspace with a high-quality dehumidifier is another meaningful improvement already in place. Outside, the back porch overlooks a large fenced yard with plenty of usable green space, while the two-car garage and generous driveway add everyday function. Waterstone offers a community pond for kayaking, canoeing, paddle boarding, and fishing, along with neighborhood trail access connecting directly to Western Branch Park and Western Branch Community Center. With substantial living space, thoughtful updates, and two areas that give you real flexibility beyond the main living spaces, this home has more depth than the photos first let on.

2004 Acentala Quay, West 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

$436,500

5 Beds ⋅ 2.1 Baths ⋅ 10657607 MLS

Seller will pay up to $12,000 in CLOSING COSTS using our preferred lender & attorney. MOVE IN READY. Brand new 19 home subdivision includes underground utilities, curb & gutter and SIDEWALKS! Stunning New Construction! Welcome to this beautiful 5-bedroom, 2.5-bath home offering 1,862 square feet of modern living space. Designed with a spacious open floor plan, it's perfect for entertaining & everyday living. Inside, the kitchen shines with soft-close cabinets, granite countertops & an Appliance package including Stainless Steel refrigerator, dishwasher, gas stove & microwave. Bathrooms have granite countertops & upgraded soft-close cabinetry for a cohesive, upscale look. Durable blend of LVP flooring and plush carpet. Primary bedroom features a tray ceiling and walk in closet. This brand-new home also features a 1 car garage, covered front porch & is the perfect blend of comfort, style, and convenience—don't miss your chance to own in the heart of Chesapeake!

903 Railroad Avenue, Central 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

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

$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

1306 Virginia Avenue, Central Chesapeake

$418,500

5 Beds ⋅ 2.1 Baths ⋅ 10657160 MLS

Stunning 5-Bedroom Home with an Assumable 2.75% VA Loan! Beautifully remodeled from top to bottom, this 5 bedroom, 2.5 bath home features an open floor plan, updated kitchen with granite countertops, custom vaulted ceilings, sunroom, wood-burning fireplace, updated bathrooms, and tankless gas water heater. Rare financing opportunity! Qualified buyers may be able to assume the existing 2.75% VA mortgage with an approximate balance of $202,668. The estimated equity difference is $215,832 based on the $418,500 asking price. Cash or additional approved financing may be used to cover the difference. Allow 45+ days for lender approval and processing. Conveniently located in historic South Norfolk, near interstates, shopping, downtown, military bases, and shipyards. Beautiful updates, great location, and an opportunity you don’t want to miss!

1306 Virginia Avenue, Central Chesapeake

$964,500

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

$625,000

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

$434,000

5 Beds ⋅ 3.1 Baths ⋅ 10656972 MLS

Welcome to this spacious 5-bedroom, 3.5-bath home offering the size, features, and flexibility today’s buyers are looking for. With major items already in place, this property gives buyers the opportunity to add their own finishing touches while enjoying strong long-term value. The functional layout includes two ensuite bedrooms with private full bathrooms, two HVAC units for separate area comfort, a dedicated laundry room, and plenty of room for everyday living or entertaining. Outside, enjoy your own private pool, detached garage, and outdoor space made for relaxing or gathering. Conveniently located with easy access to major routes, shopping, dining, and local amenities, this home offers a rare combination of space, features, and opportunity.

316 Tudor Place, Central Chesapeake

$439,900

5 Beds ⋅ 3 Baths ⋅ 10656581 MLS

Seller will pay up to $12,000 for closing cost assistance or to be used at buyer's discretion using our preferred lender and our attorney; Charming New Subdivision! Welcome to this beautiful 5-bedroom, 3 Full-bath home offering 1,862 square feet of modern living space. Designed with a spacious open floor plan, it's perfect for entertaining and everyday family living. Inside, the kitchen shines with soft-close cabinets, granite countertops. Bathrooms are also appointed with granite countertops and soft-close cabinetry for a cohesive, upscale look. Throughout the home, you'll find a blend of durable LVP flooring and plush carpet. Tray ceiling in the primary bedroom and walk in closet. This home features a 1-car garage. This brand-new home is the perfect blend of comfort, style, and convenience—don't miss your chance to own it in the heart of Chesapeake! Just Completed and Move in Ready!

913 Railroad Avenue, Central 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

$625,000

5 Beds ⋅ 2.1 Baths ⋅ 10656430 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

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

$610,000

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

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

$599,900

5 Beds ⋅ 3 Baths ⋅ 10655211 MLS

This is the one to see $40K kit. w/waterfall quartz counters, soft close cab. all 2023, ss appliances and new LVT flooring dwn, new carpet up, Quartz FP front & crown dwn, New sliding glass door to SR, $30K in windows 2023, multi use insulated shed with mini split, new HW heater, new light fixtures, new add driveway 2023, garage door, attic stairs, toilet in hall, outlet & light switches to safety, roof 2018, new paint through out, air vents, rear gutters, a must see in cul-de-sac and more...

441 Chandler Drive, South Chesapeake

$797,540

5 Beds ⋅ 3.1 Baths ⋅ 10655214 MLS

The Tillman offers 3,226 sq. ft. of stylish and flexible living - great for multigenerational living! This spacious home includes 5 bedrooms, 3.5 baths, and a 2-car garage. The first-floor primary suite provides the perfect retreat with a massive walk-in closet, dual vanities, and a private water closet. Upstairs, you’ll find a second primary-style bedroom with direct access to a full bath, offering comfort and privacy. Three additional bedrooms (each with walk-in closets), a large loft, and a convenient laundry room complete the second floor. The open-concept main level features a welcoming dining room, expansive kitchen with an oversized island and two pantries, including a Costco pantry, and a bright family room. Photos and renderings are from builder's library, actual finishes and features may vary.

911 Intracoastal Way, South Chesapeake

$369,900

5 Beds ⋅ 2.1 Baths ⋅ 10654947 MLS

Hard-to-find first-floor bedroom! This well-maintained 5-bedroom, 2.5-bath Chesapeake home delivers the space, flexibility and convenience buyers are looking for. The spacious downstairs bedroom is ideal for guests, a home office, workout room or versatile flex space, while four additional bedrooms upstairs provide plenty of room to spread out. The kitchen features granite countertops and stainless-steel appliances and opens to the den, creating an easy flow for everyday living and entertaining. Step outside to the backyard for even more room to enjoy. Built in 2000 with a comfortable two-story layout and generous living areas, this home is ready for its next owner. Conveniently located near shopping, restaurants, military bases and major commuting routes with easy access throughout Hampton Roads. Five bedrooms, flexible living space and a great Chesapeake location—this one checks a lot of boxes!

2107 Stalham Road, Central Chesapeake

$525,000

5 Beds ⋅ 3.1 Baths ⋅ 10654949 MLS

Classic character meets seriously usable space. Tucked beneath the trees in the highly desirable Silverwood neighborhood, this 5 bedroom, 3.5 bath Dutch Colonial brings together original character and thoughtful updates without losing its charm. Natural light fills the rooms and plays across the original refinished hardwood floors, bringing warmth throughout the 2,602 square foot home. The brand-new kitchen brings new cabinetry, countertops, appliances and LVP, while the stunningly updated bathrooms add a fresh, polished finish. A gas fireplace adds another touch of original character to the living room, and the finished room over the garage offers flexible space for whatever the home needs. The EZBreeze porch takes outdoor living a step further, with heat and air conditioning that keep the space comfortable throughout all the seasons. Whether enjoying a mild morning or settling in on a cooler evening, this is outdoor space with the comfort to make it genuinely usable year-round. A home with the kind of character you notice right away, paired with a fresh kitchen, beautiful updates, and spaces that make you want to stay awhile. Move in with nothing to do!

3208 Pineridge Drive, West Chesapeake

1824 Lancing Crest Lane, South Chesapeake

$1,100,000

5 Beds ⋅ 4.1 Baths ⋅ 10654932 MLS

Welcome to an exceptional 4,800 sq. ft. all-brick home in Chesapeake's sought-after Grassfield area! Offering 5 bedrooms and 4.5 baths, this spacious home features a private primary wing designed as its own retreat, complete with an incredible oversized walk-in shower that truly has to be seen. Each additional bedroom is a suite with access to its own bath, providing privacy and comfort for family and guests. Enjoy outdoor living on the screened porch overlooking the inground pool with a fountain perfect for relaxing or entertaining. The community offers its own boat ramp and marina area with water access to the Elizabeth River. Conveniently located near shopping, dining, and interstate access, this home combines space, privacy, recreation, and an outstanding Chesapeake location.

1824 Lancing Crest Lane, South Chesapeake

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