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3217 Pryor Court, South Chesapeake
$423,000
4 Beds ⋅ 2 Baths ⋅ 10645625 MLS
Make this your first stop! This well-maintained split-level home in Strawberry Acres offers the perfect blend of space, functionality, and outdoor living—and best of all, NO HOA! Fresh paint throughout and a beautifully updated kitchen featuring all-new cabinets and countertops make this home feel bright and inviting from the moment you walk in. The flexible floor plan includes a versatile front room that can serve as a home office, playroom, guest space, or additional living area. Outside, you'll find an above-ground pool, a large storage shed with electricity, and an oversized fully insulated detached garage that's perfect for a workshop, hobbies, storage, or parking. Situated on a spacious lot in a quiet neighborhood, this home offers plenty of room to relax, entertain, and make it your own. Conveniently located near schools, shopping, dining, and major commuter routes, you'll love the combination of space, updates, and freedom that this property provides!

3217 Pryor Court, South Chesapeake

1013 Port Side Way, South Chesapeake
$422,700
3 Beds ⋅ 2.1 Baths ⋅ 10620981 MLS
Stunning townhouse in the highly desirable Bryan’s Cove. This community offers resort style amenities to elevate everyday living, including a pool, private beach, clubhouse, fitness center, dog park, and playground. This beautifully designed home has been freshly painted with new carpet and offers three spacious bedrooms, including a convenient first-floor bedroom, along with 2.5 baths. The second level features an open concept layout with a bright living room, dining area, and a gorgeous kitchen, all flowing seamlessly to a wide balcony for relaxing or entertaining. The kitchen is a standout with quartz countertops, a large center island, pantry, ample cabinet space, and stainless steel appliances. The primary suite includes a walk-in closet and a private ensuite bath for your own retreat. An attached two-car garage adds both convenience and storage. Ready to enjoy low-maintenance living with exceptional amenities? Schedule your private tour today!

1013 Port Side Way, South Chesapeake

206 Dunn Street, South Chesapeake
$421,000
4 Beds ⋅ 2.1 Baths ⋅ 10626838 MLS
Welcome to this beautifully updated Great Bridge home in one of Chesapeake's most sought-after areas. Designed for comfort and everyday ease, this property offers good-sized bedrooms and a functional layout to fit a variety of lifestyles. The upgraded kitchen features modern finishes and generous prep space which is great for both daily living and entertaining. The renovated bathrooms add a fresh touch and the large tub in the primary bathroom combined with generous counter space makes it appealing to everyone. Enjoy the outdoors in this spacious backyard, offering plenty of room to relax, host, or create your own private retreat. Conveniently located near major communicating routes, shopping, dining, and local amenities, this move-in ready home is an excellent opportunity for buyers seeking both comfort and convenience in Chesapeake.

206 Dunn Street, South Chesapeake

1903 Dawnee Brook Trail S, South Chesapeake
$420,000
4 Beds ⋅ 3 Baths ⋅ 10635369 MLS
Deceptively spacious, this home reveals an interior that offers far more room than the exterior suggests. The front living room is enhanced by cathedral ceilings & a wood-burning fp, creating a striking yet comfortable first impression. The generously sized kitchen offers quartz countertops & abundant cabinet space, providing both function & flexibility for daily living. Separate living & family rooms allow for a variety of uses & lifestyles. Two bedrooms are located on the main level, including a primary suite, w/2 additional bedrooms upstairs. Recent improvements 2026: 30-year architectural roof, LVP flooring, carpet, water heater, vanities, light fixtures, ceiling fans, stove & dishwasher, 2024: HVAC. Positioned in a cul-de-sac with lake views and convenient access to the interstate, this home delivers space, updates & location in one thoughtfully designed package.

1903 Dawnee Brook Trail S, South Chesapeake

541 Bright Red Run, South Chesapeake
$420,000
3 Beds ⋅ 2.1 Baths ⋅ 10631346 MLS
This end unit townhome has been meticulously cared for by the original owners since purchasing it new in 2021. From the welcoming foyer, LVP flooring throughout the 1st floor leads to a stunning great room, which flows nicely into the dinette and gourmet kitchen that provides abundant counter space and large pantry for all your kitchen storage needs. Upstairs, 3 spacious bedrooms and 2 full bathrooms provide privacy and comfort. Your luxurious owner’s suite includes tray ceilings, a generous sized walk-in closet, a double vanity sink and large stand up shower with built-in seating. When you live in Cardinal Meadows, you’ll love the easy access to Route 17, Cedar Road, I-64 and I-464, not to mention being located right off Cahoon Parkway puts you just minutes away from all your shopping needs at Cahoon Commons.

541 Bright Red Run, South Chesapeake

1427 Hawick Terrace, South Chesapeake
$420,000
3 Beds ⋅ 2 Baths ⋅ 10625700 MLS
Welcome home to Eagle Pointe, Chesapeake's premier 55+ active adult community! This rare, move-in-ready home offers luxury, low-maintenance, one-level living with fresh paint and new carpet. The open-concept layout features a spacious kitchen that flows seamlessly into the dining room and opens to a private outdoor patio, ideal for everyday living and entertaining. The cathedral-ceiling family room with gas fireplace connects to a bright sunroom, perfect for relaxing year-round. The first-floor primary suite includes a custom walk-in closet and an ensuite bath with ceramic tile shower and split vanities. Two additional bedrooms and a full bath provide flexible space for guests, hobbies, or a home office. Enjoy resort-style amenities at The Bay Club, including indoor and outdoor pools, fitness center, social spaces, and a vibrant calendar of activities. Schedule your private tour today!

1427 Hawick Terrace, South Chesapeake

1436 Scoonie Pointe Drive, South Chesapeake
$420,000
3 Beds ⋅ 2 Baths ⋅ 10620257 MLS
Located in Eagle Pointe, Chesapeake’s premier gated 55+ community, this private neighborhood sits alongside the Cahoon Plantation Golf Course. Welcome home to this 3-bedroom, 2-bath end-unit offering a truly low-maintenance lifestyle. Thoughtfully designed, this home features a spacious eat-in kitchen, hardwood and laminate flooring throughout, and cathedral ceilings that flood the space with natural light. Unwind in the beautifully tiled sunroom, complete with a cozy double-sided fireplace—for relaxing year-round. Every detail reflects comfort, care, and ease of living. Residents enjoy exceptional amenities including a stunning clubhouse, fitness center, heated indoor pool, outdoor pool, and hot tub.Resort-style living at its finest—just move in an enjoy!

1436 Scoonie Pointe Drive, South Chesapeake

1733 Fortune Terrace, South Chesapeake
$420,000
3 Beds ⋅ 2.1 Baths ⋅ 10619367 MLS
LIKE-NEW 3-story townhouse in DESIRABLE BRYAN’S COVE neighborhood w/ TOP RATED SCHOOLS. Built in 2022 & still feels brand NEW! 3BR, 2.5 BATH, plus EXTRA 1st FLOOR ROOM (home office, gym, lounge, or a MAN CAVE), spacious 2-car garage. 2nd floor: open, modern kitchen with tall soft-close cabinets, granite countertops, large island, spacious pantry, & access to a wide balcony. Upstairs, you’ll FALL IN LOVE with the MASTER BEDROOM SUITE, thoughtfully designed with large windows, a spacious walk-in closet, and your own private bath with DOUBLE VANITY, OVERSIZED SHOWER, & linen closet. 2 additional BR on the same level & full bath, with convenient laundry - exactly where you want it! Enjoy RESORT-STYLE AMENITIES including a pool, private beach, dock, fitness room, dog park, and ground maintenance. Quiet setting just minutes from shopping, dining, and major routes. Some photos were virtually staged or digitally enhanced for marketing purposes to help visualize property's potential.

1733 Fortune Terrace, South Chesapeake

2325 Delwood Road, South Chesapeake
$419,900
3 Beds ⋅ 2.1 Baths ⋅ 10631308 MLS
Fully renovated brick ranch on a quiet, tree-lined street—this is the one you have been waiting for! Every major upgrade has been completed, offering true move-in ready living. The show-stopping kitchen features abundant soft-close cabinetry, a large island, farmhouse sink, and designer finishes that make this space the heart of the home. The spacious primary suite includes a private full bath and overlooks your backyard retreat with an in-ground pool featuring a brand new liner—perfect for summer entertaining. Two additional generously sized bedrooms, including one with its own half bath, offer ideal flexibility for guests or multi-generational living. Enjoy all new flooring, fresh paint, updated fixtures, and beautifully renovated bathrooms with custom tile. Big-ticket updates include upgraded plumbing and electrical, newer roof and windows, and a 2-year-old HVAC. Detached garage with workshop. Convenient to interstates, bases, and Greenbrier.shopping and dining!

2325 Delwood Road, South Chesapeake

2736 Benefit Road, South Chesapeake
$419,900
4 Beds ⋅ 2 Baths ⋅ 10629260 MLS
Built in 1933 and maintained by only 2 owners, this 4-bedroom, 2-bath home offers timeless character and flexible living space on nearly 2 acres of fully usable land. The 1st floor features 3 bedrooms 2 full baths, including a spacious primary suite with a walk-in closet. A traditional layout includes a living room, dining room, and a spacious kitchen with separate pantry, plus an enclosed porch/utility room for added convenience. Recent updates include fresh interior paint, refinished hardwood floors, and durable waterproof laminate flooring. Upstairs offers a bedroom, flexible living space, and a bonus nook good for an office or reading area, along with a large walk-in attic for storage or future expansion. Enjoy the fully cleared 1.9-acre lot with mature landscaping, room for outdoor activities, and a rear patio for relaxing or entertaining. Conveniently located near interstates, shopping, and amenities while offering a private, country-style setting.

2736 Benefit Road, South Chesapeake

1001 Gabion Way, South Chesapeake
$419,000
3 Beds ⋅ 2.1 Baths ⋅ 10636926 MLS
Welcome home! Located in the sought-after Bryan’s Cove neighborhood of Chesapeake, this end unit condo is sure to delight! Built in 2022, this three-story townhome boasts an open floor plan with an abundance of natural light throughout. Step inside to discover the large, versatile first-floor flex room along with an attached two-car garage. The open-concept second floor features a very spacious living room that flows into the picture-perfect kitchen complete with granite countertops, stainless steel appliances, a large island, and an eat-in dining area. Sliding glass doors invite you out onto the private balcony, where you can relax and enjoy your morning coffee or afternoon beverage. Upstairs, the third floor offers a spacious primary ensuite featuring a tray ceiling, large walk-in closet, double vanity sinks, and a tiled walk-in shower. Community amenities galore! Enjoy access to the pool, clubhouse, exercise room, two dog parks, pier, docks, playgrounds, and more! Conveniently located near shopping, dining, and interstates! This turnkey, move-in ready condo is waiting for YOU!

1001 Gabion Way, South Chesapeake

1256 Kingsway Drive, South Chesapeake
$417,900
3 Beds ⋅ 2 Baths ⋅ 10632172 MLS
Welcome to 1256 Kingsway Drive, Brick Ranch tucked into one of Greenbrier’s most convenient and sought-after locations. Set on a generous .455-acre lot, this home blends timeless character, creating a property that feels both welcoming and practical. Original hardwood flooring flowing through the main living area, adding warmth and authenticity the moment you enter. The home offers 3 bedrooms and 2 full baths, a large family room, dining room and living room. Improvements including a new roof and gutters (2025) and a new concrete driveway that enhances curb appeal and durability. Car enthusiasts, hobbyists, or anyone needing extra storage will appreciate the rare combination of a 2-car attached garage plus a detached garage with electric a perfect workshop, studio, or project space. Outdoors, the expansive yard offers room to garden, play, entertain, or simply enjoy the privacy and space that’s increasingly hard to find. Close to Interstate, shopping, restaurants and medical facilities

1256 Kingsway Drive, South Chesapeake

614 Ray Avenue, South Chesapeake
$417,000
4 Beds ⋅ 2.1 Baths ⋅ 10632519 MLS
Welcome to this beautifully 4 bed, 2.5 bath home in the desirable Crestwood community! Renovated in 2025, this home offers peace of mind with a brand new roof and windows, along with stylish updates throughout. Inside you'll find an open and inviting layout featuring a spacious living area with a cozy fireplace. The kitchen is a true standout with newer cabinetry, quartz countertops, updated appliances, a modern backsplash, and a bright breakfast area. Elegant light fixtures and fresh paint throughout the home add a clean, contemporary feel. Upstairs, you’ll find four generously sized bedrooms, including a stunning primary suite with double closets, a beautifully updated bathroom featuring a walk-in tile shower and dual vanity. Outside there's a fenced-in backyard—great for gatherings, pets, or simply unwinding. An attached garage adds convenience and extra storage. This move-in-ready home combines modern upgrades with comfortable living. Don’t miss your opportunity to make it yours!

614 Ray Avenue, South Chesapeake

1340 Cypress Pl, South Chesapeake
$416,250
3 Beds ⋅ 2.1 Baths ⋅ 10639011 MLS
Experience style, space, and convenience in this updated 3-bedroom, 2.5-bath home in Chesapeake's desirable Greenbrier area. The kitchen features granite countertops, stainless steel appliances, a pantry, breakfast bar, and ample cabinet space. Multiple living areas, including a living room and family room, offer flexibility for everyday living, work, or entertaining. The dining room showcases charming plank paneling for added character. Enjoy the fenced backyard with a deck ready for gatherings and a storage shed for extra space. Newer siding and roof enhance both value and curb appeal. Conveniently located near Chesapeake City Park, shopping, dining, major interstates, neighborhood lakes, and scenic walking paths. Don't miss this opportunity, schedule your private showing today!

1340 Cypress Pl, South Chesapeake

720 Albemarle Court, South Chesapeake
$415,000
4 Beds ⋅ 2 Baths ⋅ 10651014 MLS
Welcome to 720 Albemarle Court, an adorable ranch-style home nestled in the highly sought-after Hickory area of Chesapeake! This charming home offers 4 bedrooms and 2 full bathrooms with a comfortable and functional floor plan. Head inside to a spacious living room featuring a beautiful wood-burning fireplace. The dining area flows seamlessly into the kitchen, with easy-care laminate flooring throughout the main living areas. Three bedrooms are conveniently located on the first floor, while the finished room over the garage provides a spacious fourth bedroom with added privacy and flexibility. Out back, enjoy a large deck overlooking the generously sized backyard which is perfect for entertaining or simply enjoying your own backyard space. A wonderful opportunity to call the desirable Hickory area home!

720 Albemarle Court, South Chesapeake

220 Deepwater Drive, South Chesapeake
$415,000
3 Beds ⋅ 2 Baths ⋅ 10645328 MLS
Rare opportunity to own on deep water in Chesapeake! Fish, kayak, boat right off your back dock. Keep your boat in your own backyard on the boat lift instead of paying for dry storage or slip fees. From your private dock, enjoy an approximate 40–50-minute cruise to the open waters of the Chesapeake Bay or to Downtown Norfolk’s vibrant Waterside District where waterfront dining, entertainment and marina amenities await you! Solidly built and full of potential, this classic brick ranch home offers 1,800 square feet of living space with 3 bedrooms and 2 full baths. Whether you’re looking to renovate, personalize or invest, this home provides a fantastic opportunity to make it your own. Being sold as-is, it is ready for your vision and your creativity! Call for more details or to schedule a private tour.

220 Deepwater Drive, South Chesapeake

2829 Forehand Drive, South Chesapeake
$415,000
3 Beds ⋅ 1.1 Baths ⋅ 10644736 MLS
Beautifully updated, this spacious home features an open-concept floor plan ideal for everyday living and entertaining. The remodeled kitchen offers quartz countertops, custom soft-close cabinetry, an 8-foot island, pantry, and matching Frigidaire Professional appliances. Recessed lighting flows throughout the kitchen, dining room, and living room with a wood-burning fireplace. Additional features include large bedrooms, updated bathrooms, a dedicated office, and a heated and cooled laundry/flex space plus an additional breezeway. Major updates include new siding in 2026, HVAC and ductwork in 2025, garage doors and openers in 2025, updated electrical and plumbing, refinished hardwood and LVP flooring, and most replacement windows. Situated on approximately .75 acre with two driveways, a front porch, fenced backyard, large deck, and in-ground pool with a 2022 liner. The roof roughly 10 years young.

2829 Forehand Drive, South Chesapeake

1001 S Scarlet Oak Court, South Chesapeake
$415,000
3 Beds ⋅ 2.1 Baths ⋅ 10642085 MLS
Tucked at the end of a quiet neighborhood in the heart of Greenbrier, this home offers the perfect blend of privacy and convenience. The kitchen shines with granite countertops and stainless steel appliances, while updated bathrooms and refreshed fixtures throughout add a modern touch. Beautiful new LVP flooring flows throughout the main level, and the spacious primary suite features a private full bath. A fully fenced backyard backing to walking paths — complete with a deck and large storage shed. Smart home upgrades convey, including a Ring Camera, Ecobee thermostat, and Tesla charger! Community sidewalks make spending time outdoors easy, with playgrounds, the library, and everyday conveniences nearby. Commuters will love the quick access to military installations, top schools, major interstates, and an abundance of shopping, dining, parks, and entertainment within minutes!

1001 S Scarlet Oak Court, South Chesapeake

2312 Piers Landing, South Chesapeake
$415,000
3 Beds ⋅ 2 Baths ⋅ 10640081 MLS
This well-maintained property in the desirable Grassfield area offers a quiet neighborhood setting while remaining centrally located near shopping, dining, and interstate access. Enjoy peaceful evenings on the large covered front porch, or entertain outdoors on the spacious screened-in back porch overlooking the above-ground pool and deck. This home features numerous upgrades, including new interior doors in 2026, a new HVAC system and ductwork in 2025, crawlspace encapsulation with a dehumidifier in 2024, and a new fence in 2022. The kitchen was renovated in 2021 with updated cabinets, flooring, granite countertops, and backsplash. Additional updates include a 2018 bathroom renovation with tile and toilets, as well as replacement of Quest plumbing with PEX and gutter guards installed in 2018. Exterior features include a detached two-story garage, above-ground pool with a large deck, pool shed, and hot tub. The pool shed and hot tub are offered as-is. All pool supplies convey.

2312 Piers Landing, South Chesapeake

1915 Dobson Court, South Chesapeake
$415,000
3 Beds ⋅ 2.1 Baths ⋅ 10638193 MLS
Beautiful turnkey townhome in the sought-after Hickory Manor community of South Chesapeake! Enjoy low maintenance living in this bright, open concept home filled with natural light. The stylish kitchen features quartz countertops, under cabinet lighting, and a spacious pantry for ample storage. Upstairs, you'll find a convenient second floor laundry room, a spacious primary suite with en-suite bath, and two additional generously sized bedrooms. Unwind after a long day in your private hot tub backing up to a beautifully maintained, park-like green space. Hickory Manor offers exceptional community amenities including ponds, a clubhouse, swimming pool, grilling area, 24 hour fitness center, walking trails, and playgrounds. Sales price is based on current appraisal. Home inspection report available upon request. Hot tub conveys As Is, Where Is.

1915 Dobson Court, South Chesapeake

2035 Tuck Street, South Chesapeake
$415,000
5 Beds ⋅ 2 Baths ⋅ 10638210 MLS
Beautiful One-Acre Retreat with Main Home + Guest Suite. Discover a peaceful getaway on this spacious, tree-lined one-acre property—perfect for extended families, guests, or anyone seeking extra space to spread out. A welcoming 300 sq. ft. covered porch and brand-new firepit set the tone for relaxed outdoor living, offering the ideal setting for morning coffee, evening gatherings, or stargazing under the clear night sky. Inside the main home, you’ll find three bedrooms (one currently designed as a generous walk-in closet) and one full bathroom, all enhanced by newer renovations and beautiful hardwood floors throughout. A detached, converted garage provides incredible flexibility, featuring two additional bedrooms and its own full bath—a great option for guests, rentals, or a private home office setup. Additional highlights include: Outdoor storage shed, Extra parking areas, One-car garage, Quiet wooded surroundings and stunning night views.

2035 Tuck Street, South Chesapeake

2053 Burson Drive, South Chesapeake
$415,000
3 Beds ⋅ 2.1 Baths ⋅ 10638071 MLS
Located in the sought-after Grassfield School District, this 2021-built home offers 3 bedrooms and 2.5 baths with a bright, open-concept floor plan filled with natural light from numerous windows throughout. The kitchen features granite countertops, a large center island with sink, and ample space for cooking, gathering, and entertaining. The large first-floor primary suite includes a tiled shower and dual-sink vanity, providing convenience and privacy. Upstairs, you'll find two generously sized bedrooms and a full bath, offering flexibility for family, guests, or a home office. Enjoy the inviting front porch, spacious backyard, and convenient access to shopping, dining, medical facilities, entertainment, and major interstates. Modern construction, abundant natural light, and a functional layout make this home a must-see.

2053 Burson Drive, South Chesapeake

212 Hallbridge Drive, South Chesapeake
$415,000
3 Beds ⋅ 2 Baths ⋅ 10636998 MLS
Welcome to this charming all-brick ranch nestled on a corner lot in the heart of Great Bridge! This lovely home features three bedrooms and two full, previously renovated bathrooms. Inside, you'll find gorgeous wood floors, a spacious living room, adjoining a carpeted den/family room complete with a slider opening directly to the back patio. The comfortable eat-in kitchen boasts a convenient breakfast bar, perfect for casual dining. The attached one-car garage provides excellent storage and parking. Outside, the large backyard offers endless outdoor living opportunities; whether you dream of adding a pool, expanding the patio for entertaining, or creating your own private retreat. Great Bridge schools. Don't miss out on this fantastic home with room to grow!

212 Hallbridge Drive, South Chesapeake

910 Adventure Way, South Chesapeake
$415,000
3 Beds ⋅ 2.1 Baths ⋅ 10633355 MLS
Welcome to 910 Adventure Way, nestled in the Bryan’s Cove Community and perched alongside Deep Creek and the Elizabeth River. This inviting home offers the perfect blend of comfort, style, & functionality within a friendly community atmosphere. Fresh interior finishes, & spacious living areas create a warm & welcoming atmosphere throughout. The main level features formal living & dining rooms, plus a stunning kitchen with granite countertops, Gas Range and stainless-steel GE appliances. Enjoy relaxing on the screened-in porch overlooking an outdoor living area for gathering and entertaining. Downstairs also features the spacious Primary Suite flowing into the stylish Ensuite with double sinks and generous walk-in closet. Upstairs boasts two bedrooms with a spacious Finished Room over the Garage with walk-in closet. Solar Panels to be paid off at closing, new paint throughout living area and New Carpet installed June 2026 Reach out to the Listing Agent for a Private Showing.

910 Adventure Way, South Chesapeake

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

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