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$629,000
6 Beds 3 Baths 10645483 MLS
Rare 6-bedroom opportunity with an ideal multigenerational layout! The first floor features a bedroom, adjacent flex room, and a modified curbless shower, offering exceptional flexibility and accessibility. Beautiful neutral decor, 9' ceilings, hardwood floors, elegant crown molding, and a huge FROG provide room for everyone. The spacious primary suite features hardwood floors and two walk-in closets. Convenient second-floor laundry. Enjoy a large fenced backyard with a powered detached shed and private well for economical lawn irrigation, plus an attached 2-car garage. Meticulously maintained with annual service contracts on the HVAC, tankless water heater, and crawl space. Seller will provide a termite/moisture letter. Convenient to Millville Rd., Veterans Bridge, Shipyard Rd., and major interstates, Portsmouth, Norfolk and Suffolk! Small community vibe with minimal traffic. minimal traffic.

1816 Sunsprite Loop, South Chesapeake

$795,000
6 Beds 3.1 Baths 10643149 MLS
Well-maintained, spacious home on a prime lot in the beautiful Riverwalk community. New Roof, all new Windows, new paint interior and exterior, and new carpet in 2026! Beautiful wood floors in living and dining areas. Six bedrooms, 3 full and 1 half baths. Designed for those who love to entertain, the expansive floor plan offers elegant gathering spaces, abundant natural light, a formal butler station off the dining room. and exceptional flow throughout. The spacious eat-in kitchen and bar-top seating area open to the inviting family room with a cozy fireplace. Three additional bedrooms are located on the second level, including a versatile FROG that can serve as the 6th bedroom, home office, or recreation room. Current cooktop and built-in microwave to be replaced; buyer can choose. Large back deck with gas hookup. Residents of Riverwalk enjoy exceptional neighborhood amenities, including walking trails, a community pool, boat ramp and dock, playground, and a popular summer swim team. This is a wonderful opportunity to own a meticulously cared-for home in one of Chesapeake’s most desirable communities.

804 River Strand, South Chesapeake

$440,000
6 Beds 3 Baths 10643653 MLS
A peaceful neighborhood in the Deep Creek area of Chesapeake with close water views and wooded scenery. This home is one of the largest homes, in the neighborhood, spacious bedrooms 6 & 3 full bathrooms. This home features a modern open layout with generous living areas and a well-appointed kitchen open for entertaining. 3 first-floor bedrooms and 1 full bath provide ideal flexibility for guests or multi-generational living while the other 3 to include the Primary bedroom on the second floor. The home has a new LVP life proof floors, New paint, New carpet, New two car driveway with a wrap around sidewalk and a generous size yard for gathering a outdoor activities. Flood Insurance of 880 yearly (Never floods)

421 Plummer Drive, South Chesapeake

$999,985
6 Beds 4 Baths 10642034 MLS
White all-brick 2-story contemporary home with front porch, arches and large foyer. The backyard is a private oasis with trees, pond and flowing fountain. Enjoy the serenity of nature, including the blue herons, egrets, ducks and more, as you sip your morning coffee or have dinner on the patio. As you enter the first-floor foyer, notice the large formal dining room on the left and an archway to the familyroom with gas fireplace. Enter the huge open kitchen with granite counters, an oversized island, eat-in area and pantry. Also, on the first level are 2 bedrooms (one can be used as an office), a full bath with shower, and an archway inset that holds the Stiltz-Lift elevator. Either take the wooden stairs with wrought-iron railings or the elevator to the 2nd level. Upstairs are the Primary bedroom with extra-large walk-in closet and an incredible ensuite bath, complete with 2 sinks, large, deep soaking tub, 5 x 4 ft shower with rainfall head and sit-down area. A separate laundry room, three other bedrooms and 2 full bathrooms provide the space for family and friends to come and visit. BUT, there's more to complete the 2nd floor. Check-out the theater/game room (great for entertainment) and additional wrought-iron railings that overlook the stairs, foyer area and lead to the elevator. The extra-large 3-car garage has enough room for your cars or anything else. AND then there's the backyard; well, you'll just have to see it for yourself. This home is convenient to shops, restaurants, malls, stores, country club, banks, parks, interstate, university and so much more!

1324 Simon Drive, South Chesapeake

$624,900
6 Beds 4.1 Baths 10642445 MLS
Rare opportunity to own a beautifully updated 6-bedroom, 4.5-bath home featuring a private, fully equipped in-law suite for multigenerational living, extended family, guests, rental income, or a private home office. The main residence offers 5 spacious bedrooms, 3 full baths, and a stunning remodeled kitchen with quartz countertops, sleek high-gloss cabinetry, stainless steel appliances, and space for a large center island. The separate in-law suite lives like its own home, complete with an open loft-style bedroom, 1.5 baths, walk-in closet, full-size laundry, upgraded kitchen with quartz counters and stainless appliances, and generous living space. Recent upgrades include renovated baths, new windows, patio doors, and Nest thermostats. Step outside to your backyard oasis featuring an 8-foot in-ground pool with newer liner, filter, and pump, plus a built-in deck bar ideal for entertaining. Conveniently located near shopping, dining, schools, military bases, beaches, and major commuter routes.

501 Thornloe Ln Lane, South Chesapeake

$935,000
6 Beds 3.1 Baths 10642291 MLS
Welcome to luxury living in Chesapeake's coveted Cahoon Plantation community! This custom brick home was built in 2012. The stunning 6-bedroom home showcases a spacious open-concept design that works for both everyday living & entertaining. The beautifully appointed kitchen flows seamlessly into the main living and dining areas, creating a bright, inviting space filled with natural light & modern elegance. The kitchen offers maple cabinets, range hood, backsplash granite countertops & brand-new matte black Kitchen Aid appliances. The first-floor primary bedroom has an ensuite bathroom w/ shower, soaking tub, dual vanities and large walk-in closet. Upstairs the generously sized bedrooms provide flexibility for family, guests, or a home office. Step outside to your backyard retreat featuring a large, heated saltwater in-ground pool, play area, gas fire pit all while overlooking the woods. This home has been meticulously maintained and is ready for its new owners. Just minutes from interstates, restaurants & shopping.

409 Torre Pine Court, South Chesapeake

$899,999
6 Beds 3.1 Baths 10641499 MLS
Welcome to your own private retreat in the heart of Grassfield! Nestled on approximately 5 acres, this beautifully maintained 6-bedroom, 3.5-bath home offers more than 4,200 square feet of space designed for both everyday living and unforgettable entertaining. Inside, you'll find generous living areas with room for everyone—whether you're hosting holiday gatherings, working from home, or simply enjoying quiet evenings with family. Go outside to enjoy the peaceful surroundings, then unwind in the hot tub, which conveys with the home, making it easy to relax under the stars after a long day. Now offered at an improved price, this exceptional property also includes a seller-paid carpet allowance with an acceptable offer, giving you the opportunity to add your own personal style before moving in. If you've been dreaming of acreage, privacy, and a home that offers the perfect blend of comfort, flexibility, and room to grow, this Grassfield gem is ready to welcome you home. Schedule your private tour today and experience everything this incredible property has to offer.

2536 Seven Eleven Road, South Chesapeake

$649,900
6 Beds 2.1 Baths 10641222 MLS
Located in Chesapeake's sought-after Grassfield school district, this freshly painted, move-in ready home offers space, flexibility, and modern updates. The open floor plan is anchored by a spacious kitchen featuring Samsung Bespoke appliances, generous cabinet and counter space, and a pantry, creating a natural gathering place for everyday living and entertaining. The third floor was expanded in 2021 to include two finished rooms, providing flexible space for a home office, media room, playroom, hobbies, guests, or additional bedrooms. Major improvements include a new 1st floor HVAC in 2024 and 2nd/3rd floor HVAC installed in 2021. Outside, you'll find an expanded extra-wide driveway, EV charger, fully fenced backyard, and a spacious deck ready for cookouts, relaxing evenings, or weekend gatherings. Conveniently located near shopping, dining, major highways, and everyday conveniences, this home combines space, function, and updates in one of Chesapeake's most desirable locations. Some photos are virtually staged.

568 Waters Road, South Chesapeake

$609,900
6 Beds 3 Baths 10641027 MLS
A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch style living with 6 bedrooms including a large finished room over the garage. Family Room opens to the Kitchen and Breakfast Area. The Estates at Jolliff Landing is a charming neighborhood boasting single family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your door step in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5:00 pm at 5023 Annapolis Drive.

2223 Hampton Roads Parkway, West Chesapeake

$750,000
6 Beds 4 Baths 10640551 MLS
This is the kind of home buyers rarely find anymore. Tucked away on a quiet cul-de-sac in the heart of Great Bridge, this beautifully maintained all-brick residence offers nearly 4,000 square feet of thoughtfully designed living space, timeless craftsmanship, and the flexibility today's families are searching for. From the moment you arrive, the pride of ownership is unmistakable. Mature landscaping, impeccable curb appeal, and a welcoming front entry create an impressive first impression, while inside you'll discover generous room sizes, abundant natural light, and a floor plan designed for both everyday living and memorable gatherings. Featuring 6 spacious bedrooms and 4 full baths, this exceptional home offers a rare combination of space and versatility. Two primary suites—including a first-floor suite—provide an ideal setup for multigenerational living, extended guests, or a private home office. The beautifully updated kitchen serves as the heart of the home, offering ample workspace, abundant cabinetry, and an open flow into the living and entertaining areas. Renovated baths throughout the home reflect thoughtful updates and timeless style. Discover what truly sets this property apart. The incredible screened porch overlooks a private backyard oasis designed for year-round enjoyment. Beautiful landscaping, mature trees, a paver patio, and fire pit create the perfect setting for morning coffee, summer cookouts, celebrations, or quiet evenings under the stars. Built with the quality, craftsmanship, and substantial feel that many buyers believe is missing from newer construction, this home combines enduring value with modern comfort. Located in the highly sought-after Great Bridge school district and convenient to shopping, dining, parks, and major commuting routes, this is more than just a beautiful house—it's a place to put down roots, create memories, and truly feel at home.

900 Justin Lee Way, South Chesapeake

$778,900
6 Beds 3 Baths 10639770 MLS
Beautiful all-brick, two-story home tucked away on a quiet cul-de-sac with a huge fully fenced backyard and new 10x16 storage shed! Features include a grand two-story foyer, formal dining room, private office/study, open living area, and dream kitchen with gas range, double ovens, stainless steel appliances. New Maytag dishwasher, new garbage disposal, granite counters, island with beverage fridge and wine rack. 7 channel surround sound connected to living room, primary bedroom, and media room. First-floor bedroom and full bath offers flexible living. Upstairs includes a spacious primary suite with 3 walk-in closets, additional bedrooms, media room, laundry, and more. Built in generator, tankless gas water heater, sprinkler system, and a 2-car garage!

237 Castleberry Drive, South Chesapeake

$763,990
6 Beds 4.1 Baths 10639573 MLS
Welcome to the Tillman at Riverview Landing! The spacious home includes 6 bedrooms, 4.5 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 are from the builder's library, actual finishes and features may vary.

984 Intracoastal Way, South Chesapeake

$1,190,000
6 Beds 4.1 Baths 10639205 MLS
Welcome to a lifestyle few will ever experience. Tucked away on 1.18 private waterfront acres at the end of a quiet cul-de-sac,this extraordinary custom-built Elizabeth River estate offers over 6,900 square feet of luxury living with direct access to the Intracoastal Waterway. This is more than a home—it is a private waterfront retreat where luxury,tranquility & unforgettable entertaining come together. Imagine mornings with coffee overlooking the water as boats drift by,afternoons cruising from your private dock & 15,000-pound boat lift,& evenings enjoying breathtaking sunsets from your balcony or around the custom firepit with family & friends under the stars. Designed to impress yet comfortable for everyday living,the light-filled open floor plan showcases soaring ceilings,walls of windows,& breathtaking water views creating a seamless connection between indoor & outdoor living. Every space was designed to make everyday living extraordinary. At the heart of the home,the chef’s kitchen opens to multiple gathering spaces,creating the perfect setting for holiday celebrations,elegant dinner parties,& relaxed weekends at home. With 3 private ensuites,including a first-floor guest suite,this layout offers rare flexibility for multigenerational living,extended guests,or those who value privacy & comfort. Over $260,000 in recent improvements reflect pride of ownership,including extensive landscaping,custom firepit,underground drainage & pump system,updated flooring,renovated baths,updated kitchen,finished third floor (+600 SF),new upstairs HVAC,new water heaters,& generator connection. Dock approx. 4 years old. Water depth approx. 10' at high tide & 2–3' at low tide. Add'l features incl a 100-year roof,lifetime fence warranty,oversized 3-car garage,& dedicated storage room. Homes of this caliber rarely become available. Offering privacy,prestige,deep-water access,& resort-style waterfront living in a prime location,this exceptional estate delivers the coastal luxury lifestyle most only dream about. This is Elizabeth River living at its finest.

4200 Quailshire Court, West Chesapeake

$649,900
6 Beds 3.1 Baths 10638082 MLS
This Six Bedroom, Three and a Half Bathroom, Near New Construction Ranch Home is Move In Ready for its Next Owner. Located on 1.53 Acres of Waterfront Land, it is Perfect for Multi-Generational Living, Having Two First Floor Bedrooms with Full Ensuite Baths. The Beautiful Primary Bedroom Features Double Sinks in the Bath, Tiled Shower, a Large Walk-In Closet, and Direct Access to the Back Deck. Spacious Kitchen with Plenty of Cabinets & Granite Countertops; Open Living Room Overlooking the Backyard; Finished Room Over the Garage for a Sixth Bedroom or Entertainment Room or... You'll Love the Tranquil Views of both Water and Woods. Relax on Your Dock and Entertain on Your Deck, or the Other Way Around. The Attached Three Car Garage Provides for Both Parking and Storage. Centrally Located for Quick Access to Schools, Shopping, Entertainment, Restaurants, Parks and More. Call Now for your Personal Tour!

3504 Old Mill Road, South Chesapeake

$799,900
6 Beds 3 Baths 10633851 MLS
Welcome to your home! Like new construction maticulously well maintained home sits on a quiet culdesac in the highly desired sought-after Great Bridge High School - Johnstown Estates. Featuring 6 bedrooms, 3 bathrooms with one bedroom downstairs. Magnificent well equipped gourmet kitchen with quartz counter tops, stainless steel appliances and large island that overlooks to spacious family room with gas fireplace. The upstairs primary suite offers a luxirious bathroom with double vanity and lard walk in closet. This home includes a 2 zone HVAC system and a tankless water heater for added effeciency. Gutters system and vinyl privacy fence. Conveniently located near shopping, restaurants, and highways.

1024 Loutro Court, South Chesapeake

$839,740
6 Beds 4.1 Baths 10633665 MLS
Welcome to the Tillman at Riverview Landing! This Property is great for multigenerational families! This spacious home includes 6 bedrooms, 4.5 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 for guests, teens, or extended family. 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. This house is complete with a FINISHED BASEMENT! Photos are from the builder's library, actual finishes and features may vary.

1228 Kidbrooke Street, South Chesapeake

$609,900
6 Beds 3 Baths 10632620 MLS
A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch style living with 6 bedrooms including a large finished room over the garage. Family Room opens to the Kitchen and Breakfast Area. The Estates at Jolliff Landing is a charming neighborhood boasting single family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your door step in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5:00 pm at 5023 Annapolis Drive. Call for delivery dates.

2209 Hampton Roads Parkway, West Chesapeake

$1,075,000
6 Beds 4.1 Baths 10632029 MLS
Luxury Redefined at 1301 Simon Drive Experience the pinnacle of Chesapeake living in this custom 5,612 sq. ft. brick estate. Nestled on a spacious corner lot in Greenbrier, this 6-bed, 4.5-bath masterpiece blends timeless elegance with modern high-tech luxury. The Interior Experience: Ultimate Comfort: Enjoy radiant heated floors Chef’s Dream: Gourmet kitchen with high-end appliances and a sleek wet bar. Grand Design: Cathedral ceilings and a dramatic winding staircase. Your Private Oasis: Step outside to a brand-new, gorgeous pool oasis. Whether you're hosting a summer gala or a quiet evening by the water, this backyard is designed for pure relaxation. The Bells & Whistles: Oversized 3-car garage. Lavish primary suite with a champagne bubble spa-tub. Premium finishes and smart-home integration throughout. 1301 Simon Drive | Luxury is in the details.

1301 Simon Drive, South Chesapeake

$1,149,000
6 Beds 4.1 Baths 10626451 MLS
Best Value opportunity in Edinburgh! Beautifully well maintained home located in the desirable Edinburgh area of Chesapeake. The spacious 6 bed/4.5 ba residence offers a comfortable and functional layout with abundant natural light throughout. The kitchen, HVAC system, and water heater have all been updated within the past five years. Pre-wired for surround sound in the living room, with the primary bedroom sound system already installed and ready to use. New sprinkler system installed last year. Enjoy outdoor living on the concrete patio and nice yard. Ideally situated near a quiet dead end with trees and no home will be developed. Located in the sought after Hickory school district and conveniently close to shopping, dinning and major commuting routes.

536 Thistley Lane, South Chesapeake

$866,319
54 Beds 4.1 Baths 10619381 MLS
The Miles offers a layout designed to grow with you—while still feeling intentional and welcoming at every turn. Featuring 4 beds, 4.5 baths, & 3,585 square feet, this thoughtfully designed home delivers space, flexibility, & timeless appeal for modern living. Enter into a grand foyer that immediately sets the tone. To your left, a private home office offers the a retreat for remote work, quiet study, or creative pursuits. To the right, a formal dining room invites everything from holiday gatherings to weeknight dinners filled with conversation & connection. As you move forward, the home opens into a stunning great room, seamlessly flowing into the breakfast area / kitchen—creating the heart of home where life naturally comes together. Kitchen is designed with both beauty & practicality in mind, featuring a generous pantry —ideal for effortless entertaining & everyday organization. Just beyond breakfast area, you’ll find a half bath & direct access to the garage, making comings / goings easy & efficient. Tucked just off the great room, a versatile flex room with adjacent full bath & closet offers endless possibilities—whether you envision a guest suite, playroom, fitness space, or secondary living area. Upstairs continues to impress with spacious loft that serves as a natural gathering space—perfect for movie nights, homework sessions, or a cozy lounge. 3 additional beds provide comfort & privacy for family /guests, with Bed 2 & 3 connected by a Jack-and-Jill bathroom, blending convenience with thoughtful design. Primary suite is a true retreat, offering a peaceful escape complete with luxurious bath & expansive walk-in closet. Just outside the suite, the upstairs laundry room adds everyday ease—no hauling baskets up & down stairs, just smart living done right. Every corner has been carefully considered to support the rhythms of daily life while offering moments of comfort, connection, calm. Flexible living spaces to generous storage & intuitive layout, this home is more than a floorplan—it’s a place where memories are made!

2100 Sanderson Road, South Chesapeake

$1,250,000
6 Beds 5 Baths 10611669 MLS
Welcome to this stunning 6-bedroom, 5-bath, 4,726 sq ft brick estate set on nearly 6 acres of serene countryside. This two-story residence offers an amazing blend of luxury, comfort, and functionality. Inside, you’ll find expansive living spaces, a well-appointed kitchen, and generously sized bedrooms designed for both privacy and togetherness. The home is ideal for entertaining, featuring an in-ground heated pool for year-round enjoyment. A land-mounted solar system adds modern efficiency, keeping energy costs low while supporting sustainable living. With plenty of room to spread out, both indoors and out, this property is a rare opportunity to enjoy refined living on a private, spacious retreat.

2700 Ballahack Road, South Chesapeake

$609,900
6 Beds 3 Baths 10609830 MLS
A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch style living with 6 bedrooms including a large finished room over the garage. Family Room opens to the Kitchen and Breakfast Area. The Estates at Jolliff Landing is a charming neighborhood boasting single family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your door step in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5:00 pm at 5023 Annapolis Drive.

MM Myrtle Ii, West Chesapeake

Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.