Homes for Sale near Jolliff Middle School

• 

  

  

  /23

  $458,900

  • 4 Beds
  • 2.5 Baths
  • 2,385 Sq Ft

  4448 S Military Hwy, Chesapeake, VA 23321

  Stop the car! Come see this beautiful Gem! This beautiful home has it all including gourmet kitchen island, granite countertops, SS appliances, NEW LVP Flooring & dishwasher, tankless water heater, surround sound system, large master with walk in closet and spacious open floor plan. Exterior offers low maintenance siding, full front porch, backyard patio and plenty of room for

  

  Raietta Thomas

  Melody Matthews & Assoc. Real Estate Professionals

  (757) 792-8995

  4448 S Military Hwy, Chesapeake, VA 23321
• 

  

  

  /19

  $425,000

  • 5 Beds
  • 2 Baths
  • 3,333 Sq Ft

  3861 Ahoy Dr, Chesapeake, VA 23321

  Take a look at this beautifully updated 3,333 sq. ft. home features 5 spacious bedrooms, 2 stylish bathrooms, and a modern kitchen with granite countertops, dark cabinetry, and updated appliances. Relax or entertain on the deck outside. Move-in ready with elegant upgrades throughout—schedule your showing today!

  

  Patrick Olds

  Long & Foster Real Estate Inc.

  (757) 540-2890

  3861 Ahoy Dr, Chesapeake, VA 23321
• 

  

  

  /36

  $524,900

  • 3 Beds
  • 3 Baths
  • 2,245 Sq Ft

  4936 Barn Swallow Dr, Chesapeake, VA 23321

  Stunning landscaped yard welcomes you right to the front door of your new brick home. Experience the ranch living in established community of Jolliff Woods in Western Branch area of Chesapeake. After entering the foyer, you are invited into large family room with gas fireplace which leads into kitchen including breakfast area, island, abundance of natural light, and a beautiful view of your back

  Leigh Anne Parks Chorey & Associates Realty LTD

  4936 Barn Swallow Dr, Chesapeake, VA 23321
• 

  

  

  /43

  $610,000

  • 4 Beds
  • 2.5 Baths
  • 2,878 Sq Ft

  1812 Frederick Ct, Chesapeake, VA 23321

  Welcome to this stunning 4-bedroom, 2.5-bath all-brick home located in the highly desirable Dock Landing area of Western Branch. Boasting timeless curb appeal, rich hardwood floors and an open-concept living area. The spacious family room flows seamlessly into the dining and kitchen areas. The kitchen offers ample cabinetry, a large island perfect for the chef of the family making it the heart of

  Kim Ranno Howard Hanna Real Estate Services

  1812 Frederick Ct, Chesapeake, VA 23321
• 

  

  

  /27

  $482,900

  • 4 Beds
  • 2.5 Baths
  • 2,870 Sq Ft

  1221 Creekview Dr, Chesapeake, VA 23321

  Welcome to a well maintained and updated home in desirable Western Branch. With over 2800 sq ft this home offers 4 bedrooms, 2.5 baths, formal living room and dining room, eat-in kitchen with work island, SS appliances and lots of cabinets. The kitchen opens to a cozy family room that has a wood burning fireplace - great for entertaining, upstairs boast a spacious Primary suite w/separate

  Pamela Strahorn-Roe BHHS RW Towne Realty

  1221 Creekview Dr, Chesapeake, VA 23321
• 

  

  /30

  $500,000

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  1308 Oil Bird Ln, Chesapeake, VA 23321

  Nestled in Lakes of Jolliff neighborhood and beautifully maintained, this home offers functionality with modern convenience. White oak plank flooring can be found throughout the main living areas for durability and style. The living room features a cathedral ceiling allowing for an open and spacious feel. The primary bedroom is conveniently tucked away on the first floor - a private oasis

  Gregory Chaplain The Real Estate Group

  1308 Oil Bird Ln, Chesapeake, VA 23321
• 

  

  /48

  $535,000

  • 4 Beds
  • 3 Baths
  • 2,439 Sq Ft

  4528 Davids Mill Dr, Chesapeake, VA 23321

  Check out this move-in ready; brick ranch located in Davids Mill neighborhood of Western Branch. This one-story home boast 4 bedrooms, 3 full baths and a bonus bedroom over the garage. The foyer opens up to a spacious sitting room with formal dining room & eat-in kitchen. The family room gives a sneak peek at the spacious, fenced-in backyard. Enjoy the hot tub or go for a swim in the custom

  Dominique Ferguson Real Broker LLC

  4528 Davids Mill Dr, Chesapeake, VA 23321
• 

  

  /34

  $499,900

  • 4 Beds
  • 2 Baths
  • 2,333 Sq Ft

  4822 Lake Shore Dr, Chesapeake, VA 23321

  Fantastic 4 bedroom ranch with 1st floor primary bedroom, move in ready! Open floor plan makes great use of the square footage. Large kitchen with lots of cabinets and counter space, plus a pantry! Vaulted ceiling in the living room with gas fireplace. Formal living room and breakfast area. Deck out back overlooks wooded area. Large primary bedroom with walk in closet, primary bath with dual

  Ashley Sutton Tullio Sutton Tullio Realty LLC

  4822 Lake Shore Dr, Chesapeake, VA 23321
• 

  

  /41

  $545,000

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  4713 Jolliff Woods Dr, Chesapeake, VA 23321

  Stunning All-Brick Home Built to Last!This exceptional property offers the perfect blend of comfort, style, and durability. Enjoy resort-style living with a heated inground saltwater pool featuring an attached jacuzzi and a custom pool house, perfect for relaxation and entertaining. The 4-seasons sunroom provides year-round enjoyment with stunning views of the backyard oasis.Newly remodeled

  BK Fitz Rock Steady Group

  4713 Jolliff Woods Dr, Chesapeake, VA 23321
• 

  

  /40

  $499,000

  • 5 Beds
  • 3 Baths
  • 2,541 Sq Ft

  4901 Lake Shore Dr, Chesapeake, VA 23321

  Need room this one has it 5 bedrooms 3 baths. Updated kitchen with stainless appliances.Lots of cabinets, granite countertops. Tankless water heater. Nice size backyard.

  Maria Smoot The Real Estate Group

  4901 Lake Shore Dr, Chesapeake, VA 23321
• 

  

  /42

  $549,900

  • 4 Beds
  • 2.5 Baths
  • 2,585 Sq Ft

  4252 Raleigh Rd, Chesapeake, VA 23321

  Beautifully updated 4-bedroom, 2.5-bath home with modern upgrades throughout! This property features a brand-new roof, plumbing, electrical system, and panel. Enjoy the fresh look of new flooring, a fully renovated kitchen with stylish countertops and appliances, and updated bathrooms. The home boasts new doors, lighting, and an open-concept living space. Outdoor features include two new decks, a

  Kyle Myers Iron Valley Real Estate Norfolk

  4252 Raleigh Rd, Chesapeake, VA 23321
• 

  

  /50

  $539,000

  • 4 Beds
  • 3 Baths
  • 2,509 Sq Ft

  4812 Phoenix Dr, Chesapeake, VA 23321

  Your opportunity to move into this beautifully maintained home in the desirable and established neighborhood of Jolliff Woods is here! From the moment you arrive, it's evident that this home was loved for roughly 34 years by the same owners. With the entire house being freshly painted, the neutral color compliments the wooden accents for a blend of vintage + modern. Updates have been made within

  Jaine Lindo The Real Estate Group

  4812 Phoenix Dr, Chesapeake, VA 23321
• 

  

  /50

  $715,000

  • 5 Beds
  • 3.5 Baths
  • 4,371 Sq Ft

  1714 Fishers Cove, Chesapeake, VA 23321

  Discover modern living at its finest in this gorgeous 5-bedroom home nestled in the heart of Western Branch. Featuring an expansive open floor plan, this residence is designed with versatility and comfort in mind. At the center of the home lies a chef’s dream kitchen with sleek dark cabinetry, luxurious granite countertops, and top-of-the-line stainless steel appliances. Upstairs, the convenience

  Mia Roberson Creed Realty

  1714 Fishers Cove, Chesapeake, VA 23321
• 

  

  /25

  $625,000 New Construction

  • 5 Beds
  • 3 Baths
  • 2,497 Sq Ft

  5015 Oriole Dr, Chesapeake, VA 23321

  Brand new construction completed in 2025! This stunning 5-bedroom, 3 full bath home offers a spacious open floor plan with soaring 9-foot ceilings that flood the space with natural light. Ideal for multi-generational living or guests, the first floor includes a bedroom and full bath. The heart of the home is the gourmet kitchen, featuring a massive granite center island with a large farm sink,

  Laura Rowe EXP Realty LLC

  5015 Oriole Dr, Chesapeake, VA 23321
• 

  /2

  $609,775 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,416 Sq Ft

  MM Sorrento Rd, Suffolk, VA 23435

  The Sorrento floorplan, from 2416 sq ft to 3133 sq ft, offers ranch-style convenience with spacious, elegant design. A dramatic 2-story Family Room with sloped ceilings is the heart of the home, seamlessly connecting to the Foyer, Dining Room, Kitchen, and Breakfast Nook, ideal for everyday living and entertaining. Add an optional Sunroom with open fireplace for even more natural light and

  Kelly Moran BHHS RW Towne Realty

  MM Sorrento Rd, Suffolk, VA 23435
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  /42

  $598,500 New Construction

  • 5 Beds
  • 3 Baths
  • 2,596 Sq Ft

  4010 Lisas Cove Way, Chesapeake, VA 23321

  This is a MUST see! Step into luxury and comfort with this stunning two-story new construction home. The open-concept living area is the highlight of the first floor, featuring a spacious living area that flows into the gourmet kitchen and dining area. The kitchen is a chef's delight with granite countertops, soft-close cabinets, and stainless steel appliances. A convenient bedroom on the 1st

  Jobenia Parker Beacon Realty

  4010 Lisas Cove Way, Chesapeake, VA 23321
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  /49

  $529,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,209 Sq Ft

  MM Bayberry, Chesapeake, VA 23321

  Welcome to the Bayberry, which offers open-concept living without compromising comfort. With features like a large gourmet kitchen with granite countertops & stainless steel appliances. Walk-in closets in 3 bedrooms, family room with open loft, fireplace, downstairs master bedroom and so much more. You also have the option to build any variety of our models and completely customize them to suit

  Christian Ramirez RHOAD & CO.

  MM Bayberry, Chesapeake, VA 23321
• 

  

  /17

  $559,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  MM Bayberry 2, Chesapeake, VA 23321

  Welcome to the Bayberry II, offering open-concept living without compromising comfort. Features include a large gourmet kitchen with w/granite countertops & stainless steel appliances. Walk-in closets in 3 bedrooms, family room with open loft, fireplace, downstairs primary bedroom and so much more. The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered

  Steve Freeman RHOAD & CO.

  MM Bayberry 2, Chesapeake, VA 23321
• 

  

  /20

  $250,000

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  1725 Rowlock Rd, Chesapeake, VA 23321

  This awesome 3 bed 1 bathroom Chesapeake Virginia ranch has been tastefully renovated with an amazing new kitchen, new bathroom, new LVP flooring, Fresh paint and updated light fixtures including recessed lighting. This home has an open floor plan and TONS of natural light. The awesome screened porch is a great place to entertain and soak up some summer rays. The backyard is an amazing size and

  Jessica Lewis Iron Valley Real Estate Hampton Roads

  1725 Rowlock Rd, Chesapeake, VA 23321
• 

  

  /50

  $920,000

  • 7 Beds
  • 5 Baths
  • 4,365 Sq Ft

  4409 Anchor Bend Ct, Chesapeake, VA 23321

  Welcome to this stunning 7-year-old custom home on a quiet cul-de-sac. With 7 bedrooms, 5 bathrooms, and over 4,300 sq ft, it blends luxury, comfort, and smart design. The open floor plan features a grand 2-story foyer and chef’s kitchen with granite countertops, custom cabinets, island, and stainless steel appliances, open to the living and dining areas. A first-floor guest suite includes a full

  Linda Jones BHHS RW Towne Realty

  4409 Anchor Bend Ct, Chesapeake, VA 23321
• 

  

  /17

  $325,000

  • 4 Beds
  • 2.5 Baths
  • 1,880 Sq Ft

  4120 River Breeze Cir, Chesapeake, VA 23321

  Welcome to River Breeze Condominiums! This spacious 4-bedroom, 2.5-bath detached home offers 1,880 sqft of comfortable living in the desirable Western Branch South area. The open layout can be both relaxing and entertaining, featuring a bright living room, large kitchen, and a private patio. Primary suite includes a walk-in closet and en-suite bathroom. Conveniently located near shopping, dining,

  Nefertiti Holas Ebony Qing Real Estate Co.

  4120 River Breeze Cir, Chesapeake, VA 23321
• 

  

  /29

  $369,997

  • 4 Beds
  • 2.5 Baths
  • 2,283 Sq Ft

  4182 Taughtline Loop, Chesapeake, VA 23321

  Experience the charm of this exquisite home in the vibrant center of Chesapeake. Featuring an open floor plan with natural sunlight, this residence radiates warmth & hospitality Chefs Delight Kitchen, offering 42-inch cabinetry, center island, pantry, & all-included appliances. Relax in the welcoming family room, where a cozy fireplace sets the perfect mood for gatherings or quiet evenings.

  Shauna Lane BHHS RW Towne Realty

  4182 Taughtline Loop, Chesapeake, VA 23321
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  /28

  $345,000

  • 3 Beds
  • 1.5 Baths
  • 1,566 Sq Ft

  817 Colony Manor Rd, Chesapeake, VA 23321

  Beautiful 3 bedroom, 1.5 bath ranch style that you will want to call home! Home features 2 cozy fireplaces, lots of living space, extended driveway with large handyman garage, and huge fenced backyard. This house is move in ready! New roof installed in 2025! New back doors, fresh paint throughout home and outside front porch. Plus, many other updates you will love! Centrally located with easy

  Lisa Browder Howard Hanna Real Estate Services

  817 Colony Manor Rd, Chesapeake, VA 23321
• 

  

  /41

  $415,000

  • 4 Beds
  • 3 Baths
  • 1,822 Sq Ft

  4237 Woodland Dr, Chesapeake, VA 23321

  Beautifully renovated ranch home with 4 bedrooms and 3 full bathrooms on a large lot with a fenced backyard, a 3 car detached garage, and a cute shed. There are 2 primary suites to choose from. Open floorplan. New LVP flooring through main living areas and new carpet in the bedrooms. New kitchen with all appliances. Large laundry room. Convenient location. Close to the expressway and shopping.

  Jennifer Smithson Light Box Realty

  4237 Woodland Dr, Chesapeake, VA 23321
• 

  

  /3

  $299,900

  • Land
  • 6 Acres
  • $47,154 per Acre

  6 AC Biernot Ave, Chesapeake, VA 23321

  Breathtaking cleared parcel spanning 6.36 acres, presenting a fantastic opportunity for buyers! This land is perfect for developers, investors or someone that wants to build their dream home, featuring 254 feet of road frontage on Biernot Ave. The possibilities for development on these 6.36 acres are abundant. For more information, please contact the agent and feel free to drive by the lot to see

  Jimmy Auvil 1st Advantage Realty LLC

  6 AC Biernot Ave, Chesapeake, VA 23321
• 

  

  /21

  $235,000

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft

  3704 Bosun Dr, Chesapeake, VA 23321

  Well cared for ranch home in Chesapeake. This home has 3 bedrooms and 1 full bathroom, fenced back yard, and shed. It has been recently updated with new carpet, and flooring throughout. The kitchen and bathroom have been updated and fresh paint through out. The HVAC system has also been recently upgraded. Call for appt to see this home.

  Natalie Etheredge BHHS RW Towne Realty

  3704 Bosun Dr, Chesapeake, VA 23321
• 

  

  /29

  $2,100,000

  • Land
  • 19 Acres
  • $107,914 per Acre

  19.5AC Portsmouth Blvd, Chesapeake, VA 23321

  Attention Investors! Don't miss this one! 19.456 Acres of B-1 property (Neighborhood Business District) on the Chesapeake side of the GROWING Portsmouth Blvd corridor. Large New Construction Residential presence across the street & corner of Jolliff and Ports Blvd. Site road frontage 598.04 feet. Wonderful opportunity for your business! Retail, Brewery, Offices, etc. Amazon ORF2 Fulfillment

  Genine Cooper The Real Estate Group

  19.5AC Portsmouth Blvd, Chesapeake, VA 23321
• 

  

  /17

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  5533 Willow Lake Rd, Chesapeake, VA 23321

  Unique Opportunity in Western Branch, Chesapeake, Discover a rare opportunity to own a piece of land in the tranquil setting of Western Branch, Chesapeake. Nestled on a quiet dead-end street, this property is surrounded by beautiful wildlife, providing a serene atmosphere for nature lovers. The lot features a detached garage next to the house and a spacious barn in the back, complete with large

  Kelly Ayers Keller Williams Realty Town Center

  5533 Willow Lake Rd, Chesapeake, VA 23321
• 

  

  /11

  $249,500

  • Land
  • 5.00 Acres
  • $49,900 per Acre

  4729 Sunray Ave, Chesapeake, VA 23321

  Perfect opportunity to own 5 acres in the Western Branch zone of Chesapeake. 2 Acres in front are cleared and 3 acres in back are partially wooded. Property is zoned A1 - Take a ride around the neighborhood, and you will find new country chic farm homes, horses, farm equipment, crops....lots of ways to be close to city necessities and still enjoy country privacy. There is a septic in front of

  LeAnn Amory BHHS RW Towne Realty

  4729 Sunray Ave, Chesapeake, VA 23321
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  /3

  $24,900

  • Land

  .29ac Coffman Blvd, Chesapeake, VA 23321

  Potential for Farmers Market, Green House, Garden and Light Storage.

  Karen Swaney Salty Dog Realty LLC

  .29ac Coffman Blvd, Chesapeake, VA 23321
• 

  

  /3

  $337,500

  • 2 Beds
  • 2 Baths
  • 1,711 Sq Ft

  4262 Schooner Trail, Chesapeake, VA 23321

  For sale: This original brick house sits on over two acres of picturesque, navigable waterfront. The property offers a tranquil setting with a private drive and ample space to enjoy nature. The house features: 2 bedrooms with potential for third, a large kitchen and den, a formal living, 2 bathrooms, one which has been completely renovated, and a full basement for additional storage or potential

  Candy Dennis Long & Foster Real Estate Inc.

  4262 Schooner Trail, Chesapeake, VA 23321
• 

  

  /14

  $259,000

  • 4 Beds
  • 2 Baths
  • 1,323 Sq Ft

  3912 Starboard Rd, Chesapeake, VA 23321

  Discover a charming 4-bedroom, 2 bathroom home nestled in the heart of Chesapeake, VA. This well maintained residence offers a comfortable and inviting living space with spacious bedrooms, updated bathrooms, and a cozy family room. The home's prime location provides easy access to schools, shopping and major highways, making it an ideal choice for families or those seeking a convenient commute.

  Tamara Lawrence Vision Real Estate Group LLC

  3912 Starboard Rd, Chesapeake, VA 23321
• 

  /2

  $160,000

  • 3 Beds
  • 1.5 Baths
  • 1,505 Sq Ft

  4072 Sloop Trail, Chesapeake, VA 23321

  A great investment opportunity. Will a little TLC this townhome could be an excellent rental property or starter home. Property is being sold "AS IS". No repairs will be done by seller.

  Jacqueline Kahle J & K Realty Group

  4072 Sloop Trail, Chesapeake, VA 23321
• 

  

  /19

  $431,900 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,044 Sq Ft

  4933 Apricot Way, Chesapeake, VA 23321

  Welcome to Breck Grove, an exquisite townhome community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This tri-level Ashbury plan beautifully showcases an open floorplan w/ luxurious upgrades & a single car garage. The kitchen stuns guests w/ soft-close cabinetry & drawers, quartz countertops, subway tile backsplash, & under cabinet lighting. Easily

  Angela McCaskill Corinth Realty LLC

  4933 Apricot Way, Chesapeake, VA 23321
• 

  

  /19

  $426,900 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,044 Sq Ft

  4929 Apricot Way, Chesapeake, VA 23321

  Welcome to Breck Grove, an exquisite townhome community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This tri-level Ashbury plan beautifully showcases an open floorplan w/ luxurious upgrades & a single car garage. The kitchen stuns guests w/ soft-close cabinetry & drawers, granite countertops, subway tile backsplash, & under cabinet lighting.

  Angela McCaskill Corinth Realty LLC

  4929 Apricot Way, Chesapeake, VA 23321
• 

  

  /19

  $382,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,642 Sq Ft

  4923 Apricot Way, De Soto, VA 23321

  Welcome to Breck Grove, an exquisite townhome community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This 2-level Laurel plan beautifully showcases an open floorplan w/ luxurious upgrades & a single car garage. The kitchen stuns guests w/ upgraded quartz countertops, subway tile backsplash, soft-close drawers & under cabinet lighting. Easily

  Angela McCaskill Corinth Realty LLC

  4923 Apricot Way, De Soto, VA 23321
• 

  

  /4

  $449,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,555 Sq Ft

  MM Nansemond, Chesapeake, VA 23321

  Welcome to the Nansemond! A beautifully designed home that blends comfort and functionality! This three-bedroom, 2.5-bath layout offers a first-floor primary suite, providing convenience and privacy. The open-concept family room with a cozy gas fireplace flows seamlessly into a well-appointed kitchen, creating the perfect space for everyday living and entertaining. With first-floor laundry to add

  Donna Lakoski BHHS RW Towne Realty

  MM Nansemond, Chesapeake, VA 23321
• 

  

  /47

  $578,500 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,352 Sq Ft

  4008 Lisas Cove Way, Chesapeake, VA 23321

  A MUST see! Step into modern elegance with this beautifully designed new construction home. The open-concept layout features a chef’s kitchen with granite countertops, soft-close cabinets, and black stainless appliances overlooking the family room with an inviting fireplace. Upstairs, you’ll find a luxurious primary suite offering two walk-in closets, tray ceilings and a luxurious en-suite

  Jobenia Parker Beacon Realty

  4008 Lisas Cove Way, Chesapeake, VA 23321
• 

  

  /19

  $389,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,642 Sq Ft

  4936 Breck Ln, Chesapeake, VA 23321

  Welcome to Breck Grove, an exquisite townhome community in Western Branch, Chesapeake.

  Angela McCaskill Corinth Realty LLC

  4936 Breck Ln, Chesapeake, VA 23321
• 

  

  /24

  $696,900 New Construction

  • 5 Beds
  • 3.5 Baths
  • 4,005 Sq Ft

  MM Rosewood 2, Chesapeake, VA 23321

  The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches, lush gathering spaces, an assortment of yard games, a playground, water features, a sports field, bike/walking paths, a community center, a swimming pool, and tree-lined sidewalks. The Rosewood floor plan, offers grand features like James Hardie Plank siding, a covered porch, gourmet

  Steve Freeman RHOAD & CO.

  MM Rosewood 2, Chesapeake, VA 23321

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