Caroline County, VA Real Estate Search

Caroline County, VA 5 Bedroom Homes for Sale

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Newest Caroline County, VA 5 Bedroom Homes for Sale

5 Beds ⋅ 3 Baths

Welcome to the Salem, a beautifully designed 2,613 sq ft home offering a modern open-concept living space that meets all your family’s needs. This spacious home features a family room, kitchen, casual dining space, flex room, laundry room, and powder room on the main level, providing the perfect balance of comfort and functionality. The first-floor primary suite is a true retreat, offering a large walk-in closet and a luxurious bathroom with separate vanities and a private water closet for added convenience. Upstairs, you’ll find a huge bonus room with two walk-in closets, a full bathroom, and three additional bedrooms, offering ample space for your family to spread out and enjoy. This home combines open living spaces, modern design, and family-friendly features, making it the ideal choice for families seeking spacious living with plenty of storage and flexible space for all types of activities. Photos are from builder's library, actual selections and finishes may vary. Some selections/options may not be available.

6322 Sterling Way, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 4 Baths

From the moment you arrive, this nearly new 2023 home offers the perfect blend of modern comfort, practical design, and exceptional outdoor living. Thoughtfully upgraded and meticulously maintained, every space has been designed to make everyday living feel effortless while creating the perfect setting for gathering with family and friends. The heart of the home is its open-concept main level, where seamless flow between the living, dining, and kitchen areas creates an inviting atmosphere for entertaining or simply enjoying daily life. The first-floor primary suite offers the convenience of main-level living, while upstairs you'll find generously sized bedrooms and an expansive loft that serves as a second living area, ideal for movie nights, guests, a playroom, or a home office. Step outside and discover what truly sets this property apart. The custom stamped concrete patio is a showstopper, thoughtfully designed with separate spaces for dining, relaxing, and entertaining. A beautiful stone fire pit creates the perfect gathering spot on cool evenings, while built-in concrete lighting adds warmth and ambiance after sunset. Surrounded by low-maintenance white vinyl privacy fencing and backing to open space with no homes directly behind, the backyard offers a peaceful retreat that's as functional as it is beautiful. Working from home is effortless thanks to dedicated office space and a floor plan that provides room for everyone without sacrificing privacy. Whether enjoying your morning coffee or unwinding with a glass of wine on the patio, cozying up in the loft during the winter months, or hosting large celebrations, this home adapts beautifully to every season of life. Additional upgrades completed in 2023 include ceiling fans on both levels, updated kitchen and bathroom fixtures, stylish dining room lighting, vinyl privacy fencing, and solar panels for added energy efficiency and long-term savings. Located just minutes from the VRE, this home offers an ideal balance of peaceful small-town living and everyday convenience. Enjoy Bowling Green's charming Main Street with its locally owned coffee shop and small businesses while remaining close to shopping, dining, and commuter routes. Spacious, modern, cozy, and practical, this is more than just a house, it's a place where memories are made, celebrations are shared, and every day feels a little more comfortable than the last.

17031 Brookwood Dr, Bowling Green

Listing courtesy of Porch & Stable Realty, LLC. Contact:

5 Beds ⋅ 5 Baths

" Diamond in the Rough" This property is being sold to settle an estate and no repairs will be made. Offering considerable upside potential, this well built, private, 5 bedroom, 5 bath home is tucked away on the Choptank River in the community of Asbury. Featuring a large, open kitchen/living area with fireplace, first floor primary suite, inground pool and private pier.

8821 Dorothy Ln, Denton

Listing courtesy of Wright Real Estate. Contact: (410) 924-3111

5 Beds ⋅ 4 Baths

Welcome to this spacious and beautifully updated 5-bedroom, 4-bathroom home, perfectly situated on a large lot within walking distance of the lake. Offering an ideal blend of comfort, functionality, and charm, this property features a welcoming wraparound porch, a screened rear porch, and a fenced backyard that’s perfect for relaxing, entertaining, or enjoying the outdoors. Inside, you’ll find a freshly painted interior complemented by brand-new carpet throughout, creating a move-in-ready feel. The spacious kitchen offers plenty of room for cooking and gathering, while the oversized primary suite provides a true retreat with generous closet space. Large closets throughout the home ensure you’ll have abundant storage for every need. Additional highlights include a nearly new driveway, seasonal winter water views, and a layout designed to accommodate both everyday living and entertaining. With its combination of updates, space, and desirable location near the lake, this home is one you won’t want to miss!

408 Land Or Dr, Ruther Glen

Listing courtesy of EXP Realty, LLC. Contact: 8668257169

5 Beds ⋅ 3 Baths

Now selling in the newest section of the Ladysmith Subdivision! Welcome to the 2511 sq ft Hayden model, offering a modern open-concept living space designed for both comfort and flexibility. The main level features a welcoming living room, a spacious dining room, and a well-appointed kitchen with walk-in pantry, perfect for family gatherings and entertaining. The main floor also includes a full bedroom, a bathroom, and a versatile flex room, allowing you to create the ideal space for your family’s needs. Upstairs, an additional living space offers even more flexibility for a home office, playroom, or entertainment area. The large primary suite is a true retreat, featuring 2 large walk-in closets and a luxurious bathroom with separate vanities and a private water closet. The second floor also includes a laundry room, a full bathroom, and three additional spacious bedrooms, ensuring plenty of room for everyone. The home is complete with a walkout basement. The Hayden model is the perfect live-play-work home, offering flexible living spaces and modern amenities for today’s family, providing everything you need to live, work, and play in comfort. Photos are from builder's library, actual selections and finishes may vary.

6302 Sterling Way, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 4 Baths

The Verona is a 5 bedroom, 3.5 bathroom plan offering 2199 square feet. It features an open-concept floorplan, with a large great room, kitchen, laundry/mud room and powder room on the first floor. The chef-inspired kitchen offers a large peninsula and walk-in pantry, and flows into the expansive open-concept dining area and living room with plenty of room for entertaining. The second level includes a large owner's suite, with double vanities, water closet and an oversized walk-in closet. Th second level offers three more spacious bedrooms and a full bathroom. On the third level, an additional bedroom suite and finished storage space complete the home. Photos are from builder's library, actual finishes and features may vary.

17456 Clark And York St, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 4 Baths

With over 4,600 finished square feet, 5 bedrooms, 3.5 baths, and a fully finished walk-out basement, this spacious home offers room for everyone. A welcoming covered front porch leads into a bright, open floor plan featuring luxury vinyl plank flooring, a gas fireplace, and a beautifully updated kitchen with granite countertops, large island, double wall ovens, pantry, and new backsplash. The adjoining sunroom with cathedral ceiling fills the home with natural light and opens to the covered rear porch. Upstairs, the primary suite features cathedral ceilings, a large sitting area, oversized walk-in closet, and a spa-inspired bath with jetted tub, dual vanities, and separate shower. Three additional bedrooms, a full bath, and an upstairs laundry room complete the level. The walk-out basement is ideal for multigenerational living or guests, offering a bedroom with its own full bath, kitchenette, second gas fireplace, spacious recreation area, abundant storage, and unfinished space with potential for a sixth bedroom. Outside, enjoy a fully fenced backyard designed for entertaining with a covered porch, stamped concrete patio, and a professionally serviced 10,000-gallon in-ground pool. Major recent updates include two new HVAC systems (2025), water heater (2023), kitchen backsplash, fresh paint, soft-washed exterior, and upgraded dryer venting. A huge plus are the Solar panels for added energy savings. Conveniently located in Maury Heights, just minutes from downtown Bowling Green, I-95, and an easy commute to Fredericksburg, Richmond, Dahlgren, and Ashland. Spacious, updated, and move-in ready—this home truly has it all.

18015 Jackson Dr, Bowling Green

Listing courtesy of 1st Choice Better Homes & Land, LC. Contact: (540) 786-0088

5 Beds ⋅ 3 Baths

Welcome to the 2511 sq ft Hayden model, offering a modern open-concept living space designed for both comfort and flexibility. The main level features a welcoming living room, a spacious dining room, and a well-appointed kitchen with walk-in pantry, perfect for family gatherings and entertaining. The main floor also includes a full bedroom, a bathroom, and a versatile flex room, allowing you to create the ideal space for your family’s needs. Upstairs, an additional living space offers even more flexibility for a home office, playroom, or entertainment area. The large primary suite is a true retreat, featuring 2 large walk-in closets and a luxurious bathroom with separate vanities and a private water closet. The second floor also includes a laundry room, a full bathroom, and three additional spacious bedrooms, ensuring plenty of room for everyone. The Hayden model is the perfect live-play-work home, offering flexible living spaces and modern amenities for today’s family, providing everything you need to live, work, and play in comfort. Photos and renderings are from builder's library, actual finishes and features may vary.

17417 Riverside Dr, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 5 Baths

Exceptional Private Retreat on 10 Acres! Welcome to your own slice of Virginia paradise in the heart of Caroline County. Nestled on 10 picturesque acres surrounded by mature trees, this beautifully updated home offers the perfect blend of privacy, comfort, and convenience. Whether you're looking for room to entertain, explore nature, garden, or simply unwind, this property delivers the lifestyle you've been dreaming of—all while being just minutes from Route 1 and I-95 for an easy commute to Fredericksburg and Richmond. From the moment you step inside, you'll be impressed by the grand two-story foyer and the stunning floor-to-ceiling flagstone fireplace with a custom mantel, creating a warm and inviting focal point. Elegant arched openings between the living and dining rooms add timeless architectural charm and character. Home Features: -Spacious floor plan with **4 bedrooms and 3 full bathrooms** on the upper level. -Luxurious primary suite featuring a private sitting area, oversized walk-in closet, and spa-inspired bath with a soaking tub, separate walk-in shower, and abundant counter space. -Second bedroom with its own private en-suite bathroom—ideal for guests or multi-generational living. -Bright walk-up lower level with a large recreation room, wet bar, full bathroom, and an additional room perfect for a home office, gym, or guest room. -Brand-new hardwood flooring throughout the main level. -Brand-new carpet throughout the upper level and all staircases. Step outside to enjoy the beautifully refinished patio, a basketball court, and a detached garage/large shed overlooking approximately 2 acres of cleared land, offering endless possibilities for outdoor entertaining, gardening, a future pool, or creating your own backyard oasis. Beyond that, the remaining acreage provides your own private playground—perfect for hiking, camping, wildlife watching, or simply enjoying the peace and beauty of nature right outside your door. Opportunities to own a beautifully upgraded home on 10 private acres at such a competitive price are exceptionally rare. If you've been searching for space, privacy, modern updates, and everyday convenience without sacrificing accessibility, this is the home you've been waiting for. Schedule your private showing today before it's gone!

4443 Jericho Rd, Ruther Glen

Listing courtesy of RE/MAX Realty Group. Contact:

5 Beds ⋅ 3 Baths

Welcome to one of Denton's most charming historic homes, where timeless Victorian architecture, thoughtful updates, and small-town living come together beautifully. Situated on a picturesque corner lot in Denton's historic district, this lovingly maintained five-bedroom home offers more than 2,300 square feet of character-filled living space, abundant natural light, original architectural details, and inviting indoor and outdoor gathering spaces. The gracious covered front portico, mature landscaping, fenced yard, covered side deck, and expansive rear deck create wonderful spaces for relaxing, entertaining, gardening, and enjoying Eastern Shore living. Located within walking distance of downtown Denton's shops, restaurants, community events, and everyday conveniences, the home offers both charm and convenience. The third floor provides flexible bonus space ideal for a home office, studio, reading retreat, playroom, guest overflow, or additional storage. Surrounded by views of a beautiful mature oak tree, the space has a cozy treehouse feel that makes it especially appealing as a creative workspace or remote-work retreat. While the third floor is not connected to the home's central HVAC system, it has been comfortably used year-round with supplemental heating and cooling units. Thoughtful updates help provide peace of mind while preserving the home's historic character, including a 2018 roof, updated electrical panel, Whirlpool range (2019), refrigerator (2017), microwave (2025), Frigidaire Gallery dishwasher with new plumbing and electrical installation (2025), HVAC air handler (2012), and water heater (2011). Perfectly positioned to enjoy the best of the Eastern Shore, the home is approximately 20 minutes to Easton, 50 minutes to Annapolis, 1 hour to Rehoboth Beach, and 90 minutes to Ocean City. This is more than a house—it is a home with warmth, history, character, and heart, offering a lifestyle that blends historic beauty with everyday livability.

225 S 2nd St, Denton

Listing courtesy of Redfin Corp. Contact: 3016586186

5 Beds ⋅ 3 Baths

Rare find! A split foyer Lake Retreat with 5 bedrooms! This home has nice finishes, open floorplan, 2 car garage, back deck, nice yard. If you are looking for space, then this one needs to be on the must-see list. A great balance of Lake living with everyday convenience. CLOSE TO GOLF, WINERY, SHOPPING, YMCA, LIBRARY, CAROLINE COUNTY AGRICULTURE FAIR, CAROLINE COMMUNITY THEATER, FARMERS MARKET, KINGS DOMINION, MEADOW EVENT PARK, DOMINION RACEWAY & NEW KALAHARI RESORT WATERPARK COMING SOON ONLY 10 MILES NORTH !! LOT'S TO DO !!

66 Albertson Ct, Ruther Glen

Listing courtesy of Hometown Realty Services, Inc.. Contact:

5 Beds ⋅ 3 Baths

Now selling in the newest section of the Ladysmith Subdivision! Welcome to the 2511 sq ft Hayden model, offering a modern open-concept living space designed for both comfort and flexibility. The main level features a welcoming living room, a spacious dining room, and a well-appointed kitchen with walk-in pantry, perfect for family gatherings and entertaining. The main floor also includes a full bedroom, a bathroom, and a versatile flex room, allowing you to create the ideal space for your family’s needs. Upstairs, an additional living space offers even more flexibility for a home office, playroom, or entertainment area. The large primary suite is a true retreat, featuring 2 large walk-in closets and a luxurious bathroom with separate vanities and a private water closet. The second floor also includes a laundry room, a full bathroom, and three additional spacious bedrooms, ensuring plenty of room for everyone. The home is complete with a walkout basement. The Hayden model is the perfect live-play-work home, offering flexible living spaces and modern amenities for today’s family, providing everything you need to live, work, and play in comfort. Photos are from builder's library, actual selections and finishes may vary.

6262 Sterling Way, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 2 Baths

This is 222 S. 2nd Street, a recently renovated home with historic charm. Original wood flooring, and architectural details such as moldings and antique door knobs highlight the home's history. Though it embraces the past, the house has been updated with all new appliances, new quartz kitchen countertops, newly painted walls and new siding. The house offers something that many two-story homes do not - a spacious first floor bedroom with a full bathroom nearby. Kids and guests will have the privacy of their own floor with 4 bedrooms and a full bathroom upstairs. The walk up attic, air-conditioned and heated, provides storage and an opportunity to create more living space. The partial basement offers storage plus utility access. Outdoor lovers can relax on the screened porch, or in the fenced backyard that is big enough for activities, but small enough for easy maintenance. And it’s a short walk to the library, restaurants, and shops. Check out 222 S. 2nd St. and see what it has to offer you.-- Within walking distance to Shops, Restaurants, Library, and Parks. Minutes to Public Boat ramp, Choptank River, and State Parks. Come check this out... You won't be disappointed!

222 S 2nd St, Denton

Listing courtesy of Brenton Realty Group. Contact: 4104794663

5 Beds ⋅ 5 Baths

This home on acreage offers a rare and versatile main-level guest suite (with it's own laundry, kitchenette, living spaces and 2 full bathrooms) or entertainment wing at the rear of the home, providing exceptional flexibility for a variety of needs. Step inside from the spacious front porch to 9-foot ceilings and wood floors throughout most of the main level, creating an open and welcoming feel from the moment you enter. Recent updates add to the home’s appeal, including a water filtration system in 2025, quartz kitchen counters, kitchen backsplash, and refrigerator in 2024, wood floors in 2023, garage landing in 2022, paved driveway in 2021, original home HVAC in 2018, original home roof in 2017, and well pump in 2017. With its thoughtful layout, flexible living spaces, and meaningful updates, this home is designed to adapt to a variety of needs and lifestyles. While the original home was built in 1995, the Colonial portion of the home was added in 2010. Step outside and enjoy plenty of room to run, relax, or explore the walking trails created through the wooded portion of the acreage.

22617 Telegraph Rd, Ruther Glen

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 5403717653

5 Beds ⋅ 2 Baths

Charming 5BR detached home, located in a quiet neighborhood in Greensboro. Experience the great outdoors in your own backyard on a nearly 1/2 acre lot, adjacent to 140 acres of farmland. Enjoy the 'Sunset' from the 320 sf sunroom with sliding glass doors, or sit outside to watch the sunrise on the new 230 sf wooden front porch. Several updates include replacement windows, upgraded plumbing & electrical, new flooring & paint, jacuzzi, and much more. OWNER FINANCING AVAILABLE. Call for details.

407 W Sunset Ave, Greensboro

Listing courtesy of R&R Executive Realty. Contact: 4104321223

5 Beds ⋅ 3 Baths

Welcome to the 2511 sq ft Hayden model, offering a modern open-concept living space designed for both comfort and flexibility. The main level features a welcoming living room, a spacious dining room, and a well-appointed kitchen with walk-in pantry, perfect for family gatherings and entertaining. The main floor also includes a full bedroom, a bathroom, and a versatile flex room, allowing you to create the ideal space for your family’s needs. Upstairs, an additional living space offers even more flexibility for a home office, playroom, or entertainment area. The large primary suite is a true retreat, featuring 2 large walk-in closets and a luxurious bathroom with separate vanities and a private water closet. The second floor also includes a laundry room, a full bathroom, and three additional spacious bedrooms, ensuring plenty of room for everyone. The Hayden model is the perfect live-play-work home, offering flexible living spaces and modern amenities for today’s family, providing everything you need to live, work, and play in comfort. Photos and renderings are from builder's library, actual finishes and features may vary.

6245 Sterling Way, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 5 Baths

Wake up to sunrise on the Choptank River and wind down with some of the most stunning sunsets on the Eastern Shore — with Ospreys, Eagles, Herons, and an abundance of wildlife as your daily backdrop. This stunning 4,853 sq ft waterfront estate sits on 2.44 acres with 268 feet of private river frontage, putting you right on the water and just steps from the best of historic downtown Denton. Built in 2006 and extensively renovated in 2016, this 5-bed, 4.5-bath home has been meticulously maintained — nothing to do but move in. Two private primary suites on the main level each offer a serene river view retreat, ideal for multi-generational living or hosting guests in style. Three additional bedrooms upstairs provide room to spread out. Soaring 9-ft ceilings, hardwood floors with a dark walnut finish, maple paneling, and a custom Hagerstown Kitchens kitchen set the tone for quality throughout. Entertain on the brand-new Trex deck (2025) or unwind on the screened porch with spectacular western sunsets — and those views are yours forever. The land across the river is a protected Resource Conservation Area. All major systems are in excellent condition and maintained on yearly service contracts: three Carrier variable-speed HVAC units, dual Rinnai tankless water heaters, closed-cell foam insulation, and Hardie Board siding. The private dock features 8 ft MLW, a boat lift, and dedicated kayak dock with water, 240V power, and security cameras — accessed via hand-laid stone steps. Ospreys, Eagles, Herons, and Owls are regular visitors. A dedicated wellness room with river view includes a voice-command sauna, cold plunge, full shower, and workout space. The 3-bay epoxy-floored garage with LED lighting offers abundant storage for all your gear. A short walk to historic downtown Denton — an Eastern Shore best-kept secret with Eden Town Brewery, award-winning Caroline's Restaurant, Clayton Farms, and Shore Gourmet and the Chesapeake Culinary Center. Easton, St. Michaels, and Oxford are less than 30 minutes away, while Annapolis, Ocean City, Rehoboth Beach, Assateague, and Chincoteague are all within roughly an hour. You're already in the heart of it all.

322 S 2nd St, Denton

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

5 Beds ⋅ 4 Baths

The Verona is a 5 bedroom, 3.5 bathroom plan offering 2211 square feet. It features an open-concept floorplan, with a large great room, kitchen, laundry/mud room and powder room on the first floor. The chef-inspired kitchen offers a large peninsula and walk-in pantry, and flows into the expansive open-concept dining area and living room with plenty of room for entertaining. The second level includes a large owner's suite, with double vanities, water closet and an oversized walk-in closet. Th second level offers three more spacious bedrooms and a full bathroom. On the third level, an additional bedroom suite and finished storage space complete the home. Renderings and photos are from builder's library, actual finishes and features may vary.

6317 Sterling Way, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 4 Baths

The Verona is a 5 bedroom, 3.5 bathroom plan offering 2199 square feet. It features an open-concept floorplan, with a large great room, kitchen, laundry/mud room and powder room on the first floor. The chef-inspired kitchen offers a large peninsula and walk-in pantry, and flows into the expansive open-concept dining area and living room with plenty of room for entertaining. The second level includes a large owner's suite, with double vanities, water closet and an oversized walk-in closet. Th second level offers three more spacious bedrooms and a full bathroom. On the third level, an additional bedroom suite and finished storage space complete the home. Renderings and photos are from builder's library, actual finishes and features may vary.

6289 Sterling Way, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 4 Baths

The Verona is a 5 bedroom, 3.5 bathroom plan offering 2211 square feet. It features an open-concept floorplan, with a large great room, kitchen, laundry/mud room and powder room on the first floor. The chef-inspired kitchen offers a large peninsula and walk-in pantry, and flows into the expansive open-concept dining area and living room with plenty of room for entertaining. The second level includes a large owner's suite, with double vanities, water closet and an oversized walk-in closet. Th second level offers three more spacious bedrooms and a full bathroom. On the third level, an additional bedroom suite and finished storage space complete the home. Renderings and photos are from builder's library, actual finishes and features may vary.

6269 Sterling Way, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 4 Baths

The Verona is a 5 bedroom, 3.5 bathroom plan offering 2211 square feet. It features an open-concept floorplan, with a large great room, kitchen, laundry/mud room and powder room on the first floor. The chef-inspired kitchen offers a large peninsula and walk-in pantry, and flows into the expansive open-concept dining area and living room with plenty of room for entertaining. The second level includes a large owner's suite, with double vanities, water closet and an oversized walk-in closet. Th second level offers three more spacious bedrooms and a full bathroom. On the third level, an additional bedroom suite and finished storage space complete the home. Renderings and photos are from builder's library, actual finishes and features may vary.

17470 Clark And York Blvd, Ruther Glen

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139

5 Beds ⋅ 3 Baths

Nestled in the shadows of the Choptank River is a meticulously maintained home in the water-privileged neighborhood of Asbury. Beautiful Expansive lot size gives you the privacy needed within a walkable neighborhood. The flat level lot opens up future pool and other amenity possibilities. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A large rear screened-in porch to watch the local wildlife opens onto extensive hardscaping, perfect for an outdoor fire pit to enjoy those cool evenings with family and friends. Large open kitchen into the family room is the heart of the home that features a wood stove. 4 substantial bedrooms upstairs. Main floor features an office that could be a wide range of things, including a main floor bedroom. Steps from the Asbury Nature Trail that brings you to your community dock and water access with Huge views of the Choptank River.

24276 Asbury Dr, Denton

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

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