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704 Sandlewood Lane, South Chesapeake
$415,000
4 Beds ⋅ 2 Baths ⋅ 10628759 MLS
Rare opportunity to own a piece of Chesapeake history! Offered for the very first time by the estate, this classic 4-bedroom, 2-bathroom brick ranch is situated on a sprawling 0.34-acre lot in the heart of the 23322 zip code.Spanning 1,721 sq. ft., this solid home needs some TLC but offers incredible potential for an investor or a handy homeowner looking to build instant equity. The bones are there: a timeless brick exterior, a cozy fireplace, and an attached garage. Transform this blank canvas into your dream home while enjoying a prime location near top schools, Great Bridge Lock Park, and the Chesapeake Arboretum.Whether you're looking to renovate and flip or customize your forever home, the possibilities here are endless. Properties with this much character and upside are hard to find—bring your vision and make it yours today! Sold as-is.

704 Sandlewood Lane, South Chesapeake
514 Miami Drive, South Chesapeake
$415,000
3 Beds ⋅ 3 Baths ⋅ 10627226 MLS
LARGE BEDROOMS, LARGE BACKYARD, GREAT OPPORTUNITY ZONED IN GRASSFIELD HIGH SCHOOL DISTRICT. NEARBY INTERSTATE, PARKS, AND SHOPPING CENTERS.

514 Miami Drive, South Chesapeake
1439 Thistlewood Lane, South Chesapeake
$415,000
2 Beds ⋅ 2 Baths ⋅ 10609334 MLS
BACK ON MARKET due to the buyer not being able to close. Beautifully maintained and updated Condo in the highly sought after adult active 55+ community The Retreat at Greenbrier. Updated kitchen with Quartz Countertops, Updated Appliances and plenty of storage. HVAC System and hot water heater have been replaced within the last 5 years. Come enjoy all this Home and Neighborhood have to offer!

1439 Thistlewood Lane, South Chesapeake
1254 Winfall Drive, South Chesapeake
$414,000
4 Beds ⋅ 2.1 Baths ⋅ 10651925 MLS
** Easy Fixer Upper. ** Great House and Neighborhood. ** 3,000 Square Feet. ** Priced well below market value! ** ARV $615k to $625k+ ** Selling As-Is. ** No Contingencies. ** Cash Preferred. ** Excellent Opportunity for Handyman, Investor or Landlord.

1254 Winfall Drive, South Chesapeake
1456 Debbs Lane, South Chesapeake
$411,000
3 Beds ⋅ 2 Baths ⋅ 10649551 MLS
Location, location, location! Just off Volvo Parkway, this meticulously maintained ranch offers exceptional convenience to interstates, Chesapeake, Virginia Beach, shopping, dining, and more. Featuring 3 bedrooms and 2 baths, this move-in-ready home boasts a newly renovated primary bath with custom tile shower, granite kitchen with stainless steel appliances, and a cozy great room with vaulted ceiling and wood-burning fireplace. Updates galore include roof and attic spray insulation (2026), garage door and opener (2025), washer (2024), dryer (2025), and fireplace inspection (2025). Enjoy outdoor living with a pool featuring a 2026 pump, liner, and cover, plus Trex decking, pavers, hardscaping, and artificial turf. Fresh paint and an expanded driveway complete this beautifully updated, centrally located home!

1456 Debbs Lane, South Chesapeake
209 Rose Ash Way, South Chesapeake
$410,000
3 Beds ⋅ 2 Baths ⋅ 10643754 MLS
Nestled in Oak Grove Meadows, this beautifully maintained, single-owner gem offers 3 bedrooms, 2 full bathrooms, and an unbeatable central location just minutes from the Chesapeake Expressway and endless dining and shopping. You are also uniquely positioned just a stone's throw from 51 acres of peaceful nature trails at the Chesapeake Arboretum. Step inside to find a completely turn-key home where all the big-ticket items are already done, boasting brand-new windows and carpet, durable 2-year-old Pergo laminate flooring, a 2022 HVAC, a 2019 tankless water heater, and a 2016 roof. The 2024 kitchen remodel features new cabinets and countertops. You will love the gorgeous, built-in sunroom that was part of the original home's construction and not a later addition. Outside, the property continues to impress with a fully fenced backyard perfect for relaxing and an oversized driveway with an abundance of parking for family and friends. This beautifully updated home is truly a rare find!

209 Rose Ash Way, South Chesapeake
640 Sweet Leaf Place, South Chesapeake
$410,000
3 Beds ⋅ 2.1 Baths ⋅ 10643082 MLS
Welcome to this spacious 3-bedroom, 2.5-bath home offering over 1,900 square feet of comfortable living in the heart of Chesapeake's desirable Greenbrier area. The thoughtfully designed floor plan features generous living spaces, a welcoming great room with a fireplace, and an updated kitchen with beautiful quartz countertops that continue into the bathrooms for a cohesive, modern look. Step outside to enjoy the stamped concrete patio, added in 2021, providing the perfect space for relaxing or entertaining. Additional updates include a new HVAC system (2018), refrigerator (2024), and dryer (2026), offering peace of mind for years to come. Conveniently located within driving distance of shopping, dining, parks, Greenbrier's business district, major interstates, and military bases, this well-maintained home is ready for its next owner.

640 Sweet Leaf Place, South Chesapeake
2728 Blacksmith Trail, South Chesapeake
$410,000
4 Beds ⋅ 2 Baths ⋅ 10640949 MLS
An exciting opportunity to own this beautifully maintained home in highly sought-after Great Bridge! Welcome to this charming 4-bedroom,2-bath ranch nestled in an established Chesapeake neighborhood filled with mature trees,beautiful homes,& pride of ownership throughout. Offering the ease of one-level living,this move-in-ready home delivers the perfect blend of comfort,charm,& functionality in one of Great Bridge’s most desirable locations. Step inside to bright,inviting living spaces filled with natural light and designed for comfortable everyday living & effortless entertaining. This is the kind of home where holidays feel cozy,weekend gatherings come naturally,& everyday moments feel just a little sweeter. The thoughtful floor plan offers generous room sizes,a family-friendly layout,& abundant storage,giving everyone space to live,work,& unwind comfortably. Outside,the oversized backyard creates endless possibilities for backyard barbecues,kids at play,gardening,firepit nights,or simply relaxing after a long day. Whether hosting family celebrations or enjoying peaceful mornings with coffee outdoors,this outdoor space offers the lifestyle so many buyers are searching for. In a world where so many are craving more peace,more space,& more connection,this home delivers all three. Located near top-rated Great Bridge schools,shopping,dining,parks,& convenient interstate access,this Chesapeake home for sale offers the rare combination of location,space,& lifestyle. Ranch homes with large yards,one-level living,& this much charm in Great Bridge rarely become available. More than just a house,this is a place to slow down,spread out,& truly feel at home.

2728 Blacksmith Trail, South Chesapeake
1514 Waylen Loop, South Chesapeake
$410,000
2 Beds ⋅ 2 Baths ⋅ 10637455 MLS
Honey Stop The Car. This is what we have wanted! 2 bedrooms, 2 full baths. True 1 level living. A must see. Oversize 2 car garage. Relax on your private porch and enjoy the scenery. Close to the Clubhouse with all the activities. Pool and ponds with fountains. 2 extra parking areas and extra parking at the pool as well. Convenient to Greenbrier shopping, restaurants, drugstores, doctors and hospital.

1514 Waylen Loop, South Chesapeake
1949 Shipyard Road, South Chesapeake
$410,000
3 Beds ⋅ 2 Baths ⋅ 10633411 MLS
Enjoy the best of both worlds—PEACEFUL COUNTRY LIVING JUST MINUTES FROM CITY CONVENIENCES! This beautifully updated home sits on nearly 2 ACRES, offering space, privacy, and modern comfort. Step inside to find fresh paint, brand-new LVP flooring, and plush carpet throughout the bedrooms. The stunning open kitchen is a chef’s dream, equipped with gleaming quartz countertops, stainless steel appliances, white shaker soft-close cabinets and drawers, recessed lighting, tile backsplash and a farmhouse kitchen sink. Both bathrooms have been tastefully renovated with contemporary finishes, tile flooring and elegantly crafted tile surround shower and tub. The generous setback from the road enhances privacy and provides a tranquil setting. Plenty of storage with an oversized detached garage / workshop. Whether you're relaxing indoors or exploring your expansive property, this home delivers the perfect blend of rural tranquility and urban accessibility. Don’t miss this move-in ready gem!

1949 Shipyard Road, South Chesapeake
111 Esplanade Place, South Chesapeake
$410,000
3 Beds ⋅ 2.1 Baths ⋅ 10631968 MLS
Welcome home to this beautiful townhouse in Chesapeake's coveted Riverwalk community. This home features 3 bedrooms, 2.5 bathrooms, and stunning views of the marsh and Elizabeth River. The serene water vistas offer a peaceful escape, perfect for those with an adventurous spirit. The first floor is refreshed with new carpet and updated light fixtures. The kitchen offers hardwood floors, a dining space, and convenient powder room access. Upstairs, the primary ensuite joins two oversized bedrooms and a full hall bath to complete a spacious layout. Riverwalk provides an exceptional lifestyle with amenities including a boat launch, pool, clubhouse, tennis courts, playground, and trails. Enjoy local shopping, dining, and outdoor activities just minutes away. Ideally located near interstates and military bases.

111 Esplanade Place, South Chesapeake
1441 Scoonie Pointe Drive, South Chesapeake
$410,000
3 Beds ⋅ 2.1 Baths ⋅ 10630683 MLS
Welcome home to this beautifully updated Kilmarnoch plan in Eagle Pointe, Chesapeake’s premier 55+ adult community. Thoughtfully designed for comfort, style, & low-maintenance living, this move-in-ready home features a sought-after first-floor primary suite with dual closets, a spacious laundry room, & an oversized pantry for added convenience. The open-concept layout is filled with natural light & showcases plantation shutters, a granite kitchen with breakfast bar, & brand-new stainless steel appliances (2024), perfect for both everyday living & entertaining. Recent updates include a new HVAC system (2024), water heater (2018), and LiftMaster belt-drive garage system (2025), offering peace of mind for years to come. Enjoy a vibrant, luxury resort-style lifestyle at The Bay Club with indoor & outdoor pools, hot tub, fitness center, library, billiards room, Celebration room, catering kitchen, locker rooms, and a full calendar of social events. Call and schedule your private tour today.

1441 Scoonie Pointe Drive, South Chesapeake
505 Scarborough Drive, South Chesapeake
$410,000
3 Beds ⋅ 2 Baths ⋅ 10627440 MLS
Welcome to this 4 bedroom-ranch style home located in the highly desirable Great Bridge School District. Designed for comfortable living, this home features large bedrooms and expansive living spaces that provide plenty of room to relax, entertain, or work from home. The versatile flex space, known as the “Florida room,” offers endless possibilities - a sunroom, playroom, or additional lounge area filled with natural light. Step outside to enjoy the big backyard, complete with a patio great for gatherings, grilling, or simply unwinding. A dedicated garden area adds charm and opportunity for those with a green thumb. With its functional layout, generous space, and prime location, this home ready for its next owner to make it their own.

505 Scarborough Drive, South Chesapeake
15+AC Taft Road, South Chesapeake
$410,000
10620052 MLS
Your going to want to see this listing! Available acreage in the highly sought after Hickory and Grassfield school districts. This recently platted 21.581 acres of raw farm land is a rare find in southern Chesapeake. The property is not currently leased, but can be an option if desired. Property line adjustment of less than 1 acre to be done before closing. Buyer to do their due diligence on well, septic, and building permit. Call the listing agent for a showing today!

15+AC Taft Road, South Chesapeake
700 Pile Avenue, South Chesapeake
$409,900
3 Beds ⋅ 2.1 Baths ⋅ 10626834 MLS
Located in the Crestwood neighborhood of Chesapeake, this 3-bedroom, 2.5-bath home sits on a large corner lot and has been thoughtfully updated throughout. Bathrooms have been recently renovated, and the home features hardwood flooring on the lower level and stairs, along with an updated kitchen with granite countertops and a breakfast bar. Major systems include a roof replaced in 2020, HVAC updated in 2020, windows replaced in 2022, and gutters approximately 5 years old. Solar panels are fully paid off, offering little to no electric bill, and an EV charger is already installed. Additional highlights include a large detached 2-car garage, extended driveway, and an oversized storage shed with electricity. Conveniently located near shopping, dining, and commuter routes.

700 Pile Avenue, South Chesapeake
725 Luray Terrace, South Chesapeake
$408,000
4 Beds ⋅ 2 Baths ⋅ 10640001 MLS
IMMACULATE 4 BEDROOM RANCH IN DESIRABLE GREAT BRIDGE, CHEAPEAKE. THIS HOME PROVIDES A MODERN, OPEN FLOOR PLAN CONCEPT WITH VAULTED CEILINGS AND A MASSIVE EAT-IN KITCHEN WITH NEW STAINLESS STEEL APPLIANCES. REPLACEMENT VINYL, CLOSE TO SHOPPING, RESTAURANTS, ANIMAL CARE, HOSPITALS, AND HIGHWAY ACCESS IN ONE OF THE BEST SCHOOL DISTRICTS IN HAMPTON ROADS. CENTRAL TO ALL OF THE 757. THIS ALL BRICK HOME IS WELL BUILT, METICULOUSLY MAINTAINED, AND ABSOLUTELY MOVE-IN READY. A GREAT NEIGHBORHOOD FOR A GROWING FAMILY!

725 Luray Terrace, South Chesapeake
322 Snowberry Lane, South Chesapeake
$407,000
3 Beds ⋅ 2.1 Baths ⋅ 10632477 MLS
Located in Chesapeake, this well-maintained 3 bedroom, 2.5 bath home offers a spacious two-story layout with an open-concept design and thoughtful updates throughout. The main living area features durable flooring, abundant natural light, and a seamless flow between the kitchen, dining, and living spaces. The kitchen includes ample cabinetry, a pantry, and a breakfast area overlooking the backyard. Upstairs, the primary suite offers a walk-in closet, dual sink vanity, and private bath, while two additional bedrooms provide generous closet space and share a full hall bath. A dedicated laundry area is conveniently located on the same level as the bedrooms. Outside, enjoy a fully fenced backyard with a fire pit, large patio, and beautiful private view.The large attached one-car garage also provides additional storage space. Situated on a cul-de-sac with convenient access to shopping, dining, parks, and major commuter routes.

322 Snowberry Lane, South Chesapeake
932 Bowling Green Trail, South Chesapeake
$407,000
3 Beds ⋅ 2 Baths ⋅ 10630691 MLS
In the heart of Greenbrier this brick ranch has updates throughout. The Luxury Vinyl Plank flooring adds style as well as ease of care. Both bathrooms updated and one with custom shower door. The kitchen has updated appliances. Semi open concept in this comfortable home with wood burning fireplace/stove. New hot water heater 2022. Call to schedule an appointment as you don't want to miss the opportunity to see this sweet home.

932 Bowling Green Trail, South Chesapeake
708 Kirkwall Court, South Chesapeake
$406,000
3 Beds ⋅ 2 Baths ⋅ 10630657 MLS
Stunningly renovated!!! 3BD/2BA Cul-de-sac Dream with soaring Cathedral Ceilings with Skylights & New Everything! Brand New LVP flooring throughout, Brand New white kitchen cabinets & granite countertops, Brand New subway tile backsplash, Brand New light fixtures & ceiling fans. Large, private fenced yard-- Perfect for entertaining, this open-layout home is move-in ready.

708 Kirkwall Court, South Chesapeake
904 Levee Court, South Chesapeake
$405,900
4 Beds ⋅ 2.1 Baths ⋅ 10643939 MLS
Welcome to this beautifully updated 4-bedroom, 2.5-bath home located on a quiet cul-de-sac in the Deep Creek Landing community. Situated on an expansive lot, this move-in-ready home offers modern updates and a functional floor plan. The primary suite is conveniently located on the first floor and features an updated en-suite bath. Two additional bedrooms are also located on the main level; the fourth bedroom provides flexible space for guests, a home office, or recreation. The updated kitchen features granite countertops, stainless steel appliances, ample cabinetry, and generous counter space. Luxury vinyl plank flooring creates a durable and stylish living space. The living and dining areas provide an open layout for everyday living and entertaining. Upgrades include a new electrical panel and a newer roof, updated bathrooms and flooring, attached garage and shed offers additional storage and convenience. The spacious backyard provides plenty of room for outdoor activities and more.

904 Levee Court, South Chesapeake
904 Levee Lane, South Chesapeake
$405,000
4 Beds ⋅ 2 Baths ⋅ 10647166 MLS
If you're looking for a move-in-ready home in a desirable neighborhood that offers both style and peace of mind, you’ve found it. Meticulously maintained and showcasing true pride of ownership, this home was fully renovated in 2024 with a stunning modern kitchen and updated bathrooms, featuring quartz countertops, luxury vinyl plank flooring, stylish fixtures, and a screened porch perfect for relaxing or entertaining. Major systems have also been updated, with the roof, windows, tankless water heater, and HVAC all just two years old…allowing you to move in with confidence and enjoy your new home for years to come.

904 Levee Lane, South Chesapeake
1240 Bells Mill Road, South Chesapeake
$405,000
4 Beds ⋅ 2.1 Baths ⋅ 10640699 MLS
Welcome home to this beautiful 4 bedroom, 2.5 bath residence offering comfort, style, and functionality. The spacious primary suite features a spa-like bathroom complete with a double vanity sink, creating the perfect retreat. Enjoy cooking and gathering in the updated kitchen equipped with stainless steel appliances and ample space for entertaining. The open and inviting living area is ideal for hosting guests or spending quality time with family. A generously sized laundry room adds everyday convenience to this well-appointed home. Come tour before it's gone!

1240 Bells Mill Road, South Chesapeake
1232 Quarter Path Trail, South Chesapeake
$405,000
3 Beds ⋅ 2.1 Baths ⋅ 10638375 MLS
Charming and meticulously maintained 3-bedroom, 2.5-bath home featuring manicured landscaping, a beautifully remodeled kitchen, updated bathrooms, and a bright sunroom overlooking the spacious deck perfect for entertaining. The fenced backyard is beautifully maintained and includes a large storage shed for added convenience. Located in a highly desirable community with easy access to major highways, shopping, dining, and everyday amenities. This move-in-ready home offers the perfect blend of comfort, style, and location.

1232 Quarter Path Trail, South Chesapeake
412 Weeping Cedar Trail, South Chesapeake
$405,000
4 Beds ⋅ 2 Baths ⋅ 10637388 MLS
Welcome to this beautifully maintained home in the sought after Deep Creek area of Chesapeake. The home offers comfort, style, and peace of mind with numerous recent updates. Major improvements include a new roof (2024), tankless water heater (2024), updated flooring (2023), new fence (2023), refreshed carpet (2026), and energy efficient windows (2015). Enjoy outdoor living on the newly updated deck perfect for morning coffee, weekend BBQs, or relaxing evenings. A spacious front porch adds charm and creates a warm, inviting entrance to the home. Inside, the thoughtfully designed layout offers generous living space for today’s lifestyle. The primary suite features an elegant tray ceiling and an ensuite bath with double vanities. Two additional bedrooms, along with a spacious finished room over the garage (FROG), provide flexible options for a home office, media room, guest suite, or additional bedroom. This move in ready home combines modern updates with timeless comfort.

412 Weeping Cedar Trail, South Chesapeake
1632 Head Of River Road, South Chesapeake
$405,000
3 Beds ⋅ 2 Baths ⋅ 10635139 MLS
Welcome to 1632 Head of River Rd. This ranch sits on a half acre lot, complete with a fenced in backyard. Updated kitchen with brand new flooring. Natural hardwood floors throughout the living room and bedrooms. Bonus room off the kitchen suitable for office, flex or extra bedroom. Water softener installed 2020 and HVAC 2019.

1632 Head Of River Road, South Chesapeake
208 Terwillinger Road, South Chesapeake
$405,000
3 Beds ⋅ 2 Baths ⋅ 10633474 MLS
Beautiful 3 bedroom 2 bath home with a large 2 car garage/workshop. This home sits on a quiet dead end street on .63 Acres. Across the street is a park and playground. Cozy living room with a wood burning fireplace, large bonus room/office. Huge back deck overlooks the extremely private back yard. This is a rare find! See the attached 3D virtual tour.

208 Terwillinger Road, South Chesapeake
205 Kalmar Drive, South Chesapeake
$405,000
3 Beds ⋅ 2 Baths ⋅ 10627274 MLS
ALL BRICK RANCH WITH 3 BEDROOMS, 2 FULL BATH, BIG LOT WITH DETACHED GAGRAGE AND XL SHED/STORAGE. UPGRATED BATHROOMS AND KITCHEN AND MUCH MORE

205 Kalmar Drive, South Chesapeake
1404 Pamlico Boulevard, South Chesapeake
$403,000
3 Beds ⋅ 1.1 Baths ⋅ 10639255 MLS
**OPEN HOUSE THIS SUNDAY, 06/14/26 FROM 9:00-11:30AM**Recently renovated brick ranch on a 1/3 acre lot. Plenty of room for a detached garage or pool. The interior has a newer kitchen w/ss appliances & locally manufactured cabinets which include soft close doors & drawers. Both baths were recently fully renovated. There is luxury vinyl plank flooring in all the home except the baths, which have ceramic tile. The garage has been converted into an extra room that would make a great office, exercise room or home schooling area. A large addition on back provides a family room w/fireplace. The home has a newer heat pump system, replacement windows & architectural shingle roof (all replaced about 2022). All the exterior trim is wrapped for low maintenance. A large partially covered deck overlooks the spacious backyard. Seller added an electric vehicle charging station. Hickory schools. Owner/Agent.

1404 Pamlico Boulevard, South Chesapeake
400 Las Gaviotas Boulevard, South Chesapeake
$402,000
4 Beds ⋅ 2.1 Baths ⋅ 10640334 MLS
Property sold strictly AS-IS, WHERE-IS. Seller to make no repairs, credits, concessions, warranties, or representations. Inspections are welcome for buyer’s informational purposes only. Buyer to verify all information and perform all due diligence.

400 Las Gaviotas Boulevard, South Chesapeake
1715 Woodmill Street, South Chesapeake
$400,000
3 Beds ⋅ 2.1 Baths ⋅ 10649257 MLS
Welcome to 1715 Woodmill Drive, where the front yard takes care of itself. The association maintains the front landscaping, leaving the backyard yours to shape however you like, whether that's a garden, a grill setup, or a quiet spot to unwind.Three bedrooms plus a loft give you room to spread out, with the loft ready to work as an office, a reading nook, with built in cabintes. Recent updates include new flooring throughout, fresh paint, new fixtures, and a new vanity in the primary bath, along with a curbless walk-in shower that brings a clean, modern look and everyday ease. The open flow from kitchen to living makes hosting simple, whether it's a full dinner or a quiet evening at home.Minutes to shopping, dining, and I-264. Schedule your showing today.

1715 Woodmill Street, 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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