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Houses for Sale in 21401

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  • /56

    $925,000

    • 4 Beds
    • 4 Baths
    • 3,200 Sq Ft

    2977 Southaven Dr, Annapolis, MD 21401

    This stunning log home on 2.48 scenic acres (with the potential to subdivide) offers the perfect blend of rustic elegance and thoughtful upgrades. Surrounded by lush landscaping, the property provides treetop views and a glimpse of the water during the winter months. The impressive two-story living room showcases a dramatic wood-burning fireplace and flows effortlessly into the dining area and

    Agent Photo

    Scott Smolen

    RE/MAX Leading Edge

    (410) 846-6686

    2977 Southaven Dr, Annapolis, MD 21401
  • /52

    $1,398,000

    • 4 Beds
    • 4 Baths
    • 3,070 Sq Ft

    357 Overlook Trail, Annapolis, MD 21401

    Enchanting Craftsman-Style Waterfront Retreat in Epping ForestTucked away in the prestigious gated community of Epping Forest, this beautifully renovated Craftsman-style home offers a rare opportunity to enjoy serene waterfront living with a private deep-water pier on Clements Creek, just off the Severn River. Complete with a 12,000 lb boat lift and a private sandy beach, it’s a dream for

    Agent Photo

    Darrel Reel

    Corner House Realty

    (410) 415-1480

    357 Overlook Trail, Annapolis, MD 21401
  • /10

    $849,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,580 Sq Ft

    2175 Glencrest Circle - Taft Model, Annapolis, MD 21401

    Ameri-Star Homes is pleased to offer this incredible opportunity for a to-be-built, craftsman-style home situated on a beautiful almost half acre lot with walkout basement condition in the well-established neighborhood of Rolling Knolls, in Annapolis. *Builder is paying $5,000 TOWARDS CLOSING COSTS with use of builders approved lender and title company. Our exciting Taft model is appointed with

    Julie Lamartina-Dinko Douglas Realty, LLC

    2175 Glencrest Circle - Taft Model, Annapolis, MD 21401
  • /76

    $1,375,000 Open Fri 4:30PM - 6:30PM

    • 6 Beds
    • 4 Baths
    • 2,568 Sq Ft

    14 Jefferson Place, Annapolis, MD 21401

    Welcome 14 Jefferson Place located in the highly sought-after President's Hill neighborhood of Downtown Annapolis! This six-bedroom, four-bathroom versatile property offers two side-by-side residences under one roof—perfect as a multi-generational home, short or long-term rental investment, or owner-occupied duplex. Each side of the home features three spacious bedrooms, one full bath, and one

    Jennifer Siska Long & Foster Real Estate, Inc.

    14 Jefferson Place, Annapolis, MD 21401
  • /38

    $674,000

    • 4 Beds
    • 3.5 Baths
    • 2,414 Sq Ft

    1807 Green Top Ct, Annapolis, MD 21401

    Welcome home to this beautiful property set on a gorgeous lot with mature trees and thoughtfully designed landscaping. A long driveway leads to the inviting front porch and fenced yard with parking made easy. Inside, hardwood floors span the main level, featuring a formal dining and living room, plus a cozy family room with a brick-accented fireplace. The eat-in kitchen offers stainless steel

    Jonathan Scheffenacker Redfin Corp

    1807 Green Top Ct, Annapolis, MD 21401
  • /54

    $799,999

    • 4 Beds
    • 3.5 Baths
    • 2,568 Sq Ft

    701 Sonne Dr, Annapolis, MD 21401

    Welcome to your dream home nestled in a serene park-like setting! This stunning Colonial house offers a perfect blend of modern upgrades and classic charm, making it an ideal retreat for families or anyone seeking a peaceful yet conveniently located haven. The beautifully updated home boasts fresh new paint and flooring throughout. The spacious main level includes a living room, dining

    Mike Torrey Blackwell Real Estate, LLC

    701 Sonne Dr, Annapolis, MD 21401
  • /102

    $1,250,000

    • 6 Beds
    • 5.5 Baths
    • 7,633 Sq Ft

    522 Epping Forest Rd, Annapolis, MD 21401

    Exquisite 7,633 Sq. Ft. Stone Front Estate on Over an Acre with Water Access & Resort-Style AmenitiesWake up to the peaceful sounds of nature and end your day with breathtaking sunsets from your private balcony in this beautifully renovated 7,633 sq. ft., 6-bedroom, 5.5-bath stone front estate. Set on over an acre in the coveted Saefern neighborhood, this home perfectly blends elegance,

    Sonia Singh Samson Properties

    522 Epping Forest Rd, Annapolis, MD 21401
  • /63

    $699,900

    • 4 Beds
    • 3 Baths
    • 2,342 Sq Ft

    10 N Homeland Ave, Annapolis, MD 21401

    You’ve Got to See This One!Absolutely meticulous from top to bottom, this stunning 4-bedroom, 3-bath home in the charming community of Homewood is bigger than it looks and packed with upgrades. Step inside to find a spacious owner’s suite with a large walk-in closet and a well-designed bathroom, a gorgeous updated kitchen with quartz countertops, stylishly renovated bathrooms, luxury vinyl

    Christine Schumaker Douglas Realty LLC

    10 N Homeland Ave, Annapolis, MD 21401
  • /45

    $1,590,000

    • 6 Beds
    • 4.5 Baths
    • 6,435 Sq Ft

    301 Eatons Landing Dr, Annapolis, MD 21401

    Tucked away beyond the busy streets, Eaton’s Landing offers a serene retreat on a picturesque peninsula surrounded by water. This custom-built home with remodeling updates and additions by the late renowned architect Peter Andrews, with 6 bedrooms and 4.5 baths showcases timeless quality and design. Sited on a 40,890 sq. ft. corner lot, the property features an inground, Gunite pool with spacious

    Brad Kappel TTR Sotheby's International Realty

    301 Eatons Landing Dr, Annapolis, MD 21401
  • /92

    $989,500

    • 4 Beds
    • 5 Baths
    • 5,771 Sq Ft

    702 Pearson Point Place, Annapolis, MD 21401

    Welcome to this beautifully maintained residence in the amenity-rich community of Kingsport in Annapolis. Tucked into a picturesque neighborhood known for its scenic walking paths, swimming pool, tot lots, community pier, kayak storage, tranquil ponds with fountains, and lush landscaping, this home offers an exceptional lifestyle both inside and out.Lovingly cared for by its original owners,

    Lisa Barton Coldwell Banker Realty

    702 Pearson Point Place, Annapolis, MD 21401
  • /54

    $1,025,000

    • 5 Beds
    • 3.5 Baths
    • 4,204 Sq Ft

    210 Bowen Ct, Annapolis, MD 21401

    Welcome to an exquisite single-family residence—a turnkey, move-in ready home just minutes from Historic Annapolis, major commuter routes, and marinas. Thoughtfully updated and designed for both daily living and grand entertaining, this property seamlessly blends refined finishes with functional living spaces. A stunning new gourmet kitchen with custom cabinetry, upgraded appliances and a large

    Richard Curtis Curtis Real Estate Company

    210 Bowen Ct, Annapolis, MD 21401
  • /56

    $950,000

    • 4 Beds
    • 3.5 Baths
    • 4,440 Sq Ft

    534 Post Oak Rd, Annapolis, MD 21401

    Welcome to your dream home in the exclusive Windfern Forest community—a private, water-privileged enclave of executive homes offering both tranquility and recreation. Nestled on a spacious .54-acre cul-de-sac lot, this well-maintained home offers approximately 5,100 square feet of living space. Inside, you’ll find four generously sized bedrooms and 3.5 bathrooms, including a luxurious primary

    Kimberly O'Connor Coldwell Banker Realty

    534 Post Oak Rd, Annapolis, MD 21401
  • /53

    $1,199,999

    • 5 Beds
    • 4 Baths
    • 3,255 Sq Ft

    767 Bon Haven Dr, Annapolis, MD 21401

    Discover luxurious living in this exceptional 4-bedroom, 4-bathroom home nestled on a full acre in an exclusive water access community. This meticulously crafted residence seamlessly blends elegant design with modern comfort, offering the perfect retreat for those seeking both tranquility and sophistication. The expansive one-acre lot offers endless possibilities for outdoor enjoyment, including

    Sean O'Connor Coldwell Banker Realty

    767 Bon Haven Dr, Annapolis, MD 21401
  • /63

    $1,168,000

    • 3 Beds
    • 2 Baths
    • 2,064 Sq Ft

    637 Chase St, Annapolis, MD 21401

    Come take advantage of this incredible opportunity! Discover an enchanting classic brick residence in Murray Hill— Lovingly maintained and beautifully detailed, this timeless home features solid plaster walls, hardwood floors, 81⁄2‐foot ceilings, and graceful archways. The updated kitchen flows seamlessly into a versatile layout that can easily accommodate a first‐floor primary suite—currently

    Georgie Berkinshaw Coldwell Banker Realty

    637 Chase St, Annapolis, MD 21401
  • /51

    $999,000

    • 6 Beds
    • 6.5 Baths
    • 6,612 Sq Ft

    2000 Monticello Dr, Annapolis, MD 21401

    Welcome to this exceptional former model home in the prestigious Monticello enclave—ideally located just moments from Annapolis’ finest dining, shopping, and commuter routes. This residence showcases endless upgrades and over 6,700 square feet of refined living across three spacious levels, blending timeless elegance with cutting-edge comfort.A dramatic two-story foyer with striking

    Peggy Love Long & Foster Real Estate, Inc.

    2000 Monticello Dr, Annapolis, MD 21401
  • /72

    $950,000

    • 4 Beds
    • 2.5 Baths
    • 2,142 Sq Ft

    2942 Southaven Dr, Annapolis, MD 21401

    Stunning Updated Colonial in a Water-Privileged Community! This beautifully renovated four-bedroom, two-and-a-half bath home features a custom kitchen with all-new cabinetry, Calcutta Quartz countertops, and sleek stainless-steel appliances, including dual ovens with a gas cooktop. The inviting family room is equipped with built-in surround sound speakers, perfect for entertaining. The luxurious

    James Fegan RE/MAX Executive

    2942 Southaven Dr, Annapolis, MD 21401
  • /40

    $899,000

    • 5 Beds
    • 4.5 Baths
    • 3,586 Sq Ft

    730 Crisfield Way, Annapolis, MD 21401

    Amanda Callahan Long & Foster Real Estate, Inc.

    730 Crisfield Way, Annapolis, MD 21401
  • /71

    $950,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 2,648 Sq Ft

    1698 Saefern Way, Annapolis, MD 21401

    This contemporary home blends modern design with traditional touches, offering comfort, elegance, and function. A dramatic wall of glass in the living room frames views of birds, wildlife, and the home’s stunning landscape gardens. The vaulted ceilings create more elegances to this open-floor concept. The first-floor primary suite is complemented by a full laundry room on the same level, creating

    Dee Dee McCracken Coldwell Banker Realty

    1698 Saefern Way, Annapolis, MD 21401
  • /50

    $3,890,000

    • 6 Beds
    • 9 Baths
    • 9,176 Sq Ft

    840 Childs Point Rd, Annapolis, MD 21401

    An extraordinary private waterfront estate, perfectly positioned on Church Creek with direct access to the South River—this offering is a rare blend of luxury, design, and location. Ideally located just minutes from Annapolis and convenient to both Washington D.C. and Baltimore, the home is masterfully designed for elevated everyday living and effortless entertaining, whether hosting an intimate

    Brad Kappel TTR Sotheby's International Realty

    840 Childs Point Rd, Annapolis, MD 21401
  • /39

    $599,900

    • 3 Beds
    • 1.5 Baths
    • 1,899 Sq Ft

    8 Wainwright Dr, Annapolis, MD 21401

    Welcome to 8 Wainwright Drive, a rare opportunity in the highly sought-after Admiral Heights community—just minutes from the Naval Academy, downtown Annapolis, and the waterfront lifestyle that makes this area world-renowned. This charming 3-bedroom, 1.5-bath home offers you more than just a place to live—it offers a chance to secure a home in a premier neighborhood at a price that is almost

    Evan Weissman Real Broker, LLC

    8 Wainwright Dr, Annapolis, MD 21401
  • /55

    $495,000

    • 2 Beds
    • 1 Bath
    • 1,002 Sq Ft

    251 Cape Saint John Rd, Annapolis, MD 21401

    Step into an unparalleled opportunity to own a piece of Cape St. John — all for under $500,000! This rare gem offers the perfect blend of coastal charm, modern upgrades, and an enviable location in one of the area’s most beloved waterfront communities.Welcome to your dream retreat! Just a short stroll from your door, you’ll find one of the community’s best private beaches, complete with a

    Jason Donovan RE/MAX Leading Edge

    251 Cape Saint John Rd, Annapolis, MD 21401
  • /46

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    114 2nd St, Annapolis, MD 21401

    Annapolis One-Level Living with Endless Potential!Discover over 2,300 sq. ft. of spacious one-level living on a large 1⁄4-acre lot in a quiet, sought-after neighborhood. This home offers an upgraded kitchen with Oak cabinets, Corian countertops, and newer appliances—perfect for culinary enthusiasts. Beneath the carpet in the living room and bedrooms, beautiful hardwood floors await your

    James Fegan RE/MAX Executive

    114 2nd St, Annapolis, MD 21401
  • /80

    $2,800,000

    • 6 Beds
    • 4 Baths
    • 4,900 Sq Ft

    778 Bon Haven Dr, Annapolis, MD 21401

    Exquisite South River Waterfront Estate Coming Soon! Experience waterfront living at its finest in this rare South River estate situated at the end of a quiet cul-de-sac. Elevated above the water on a private 1.07-acre lot with 132 feet of premier frontage, this stunningly remodeled 4,900+ sq. ft. rancher offers timeless elegance, modern sophistication, and panoramic river views from

    Steven Knopf Engel & Völkers Annapolis

    778 Bon Haven Dr, Annapolis, MD 21401
  • /105

    $825,000

    • 4 Beds
    • 3.5 Baths
    • 3,694 Sq Ft

    702 Banneker Ln, Annapolis, MD 21401

    Amazing Opportunity to own this SFH in Kingsport Subdivision of Annapolis!! 4 Bedroom, 3.5 Bathroom, 2 Car Garage, w/ over 5,000 Total Sq Ft. (Sellers has a 2.375% VA Assumable Loan) As soon as you walk thru the door you will fall in love with the Grand Entrance, there are 9 Foot Ceilings throughout w/ Columned Entry to a Formal Living and Dining Room w/ Crown Molding and Chair Rail Detailing.

    Sandy Patterson Taylor Properties

    702 Banneker Ln, Annapolis, MD 21401
  • /56

    $2,200,000 Open Wed 1PM - 4PM

    • 6 Beds
    • 4 Baths
    • 3,415 Sq Ft

    192 Duke of Gloucester St, Annapolis, MD 21401

    Welcome to the Thomas Hyde House – a rare opportunity to own a piece of Annapolis history in the heart of downtown. Built in 1769, this impeccably restored Federal- style property blends 18th-century charm with modern luxury. Perfectly situated on sought- after Duke of Gloucester Street, this vibrant and colorful home offers stunning views of the Maryland State House and extremely rare

    Brian Jacobs Coldwell Banker Realty

    192 Duke of Gloucester St, Annapolis, MD 21401
  • /49

    $890,000

    • 4 Beds
    • 2.5 Baths
    • 2,945 Sq Ft

    309 Mcdonough Rd, Annapolis, MD 21401

    Admiral Heights Beauty! 309 McDonough Rd features modern upgrades in a layout design for everyday living. With major systems updated and stylish finishes throughout, this is a home you can move right into and enjoy for years to come.The kitchen, updated in 2021, features butcher block counters, crisp white cabinetry, and modern appliances. Hardwood floors flow through the main and upper

    Cathy Gazzo EXP Realty, LLC

    309 Mcdonough Rd, Annapolis, MD 21401
  • /27

    $575,000

    • 5 Beds
    • 2 Baths
    • 2,236 Sq Ft

    1831 Drew St, Annapolis, MD 21401

    Tucked away with a long, freshly paved driveway and generous outdoor space, 1831 Drew Street offers the comfort, space, and freedom to live how you’ve always wanted. Picture morning coffee with sunlight flooding through the windows that wrap around the home. Backyard cookouts just off the kitchen. Movie nights or game days in a flexible lower level that fits your life.This home has been

    Kevin Brown Long & Foster Real Estate, Inc.

    1831 Drew St, Annapolis, MD 21401
  • /59

    $824,900

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft

    1755 Robinhood Rd, Annapolis, MD 21401

    From the moment you arrive, this 3-bedroom, 2.5-bathroom home welcomes you with charm and ease. A brand new front porch patio sets the tone—inviting you to sit a while, breathe in the fresh air, and feel instantly at home. Step inside and you're greeted by natural light, soft textures, and a layout that was made for both connection and calm. The kitchen is a true standout—fully updated with sleek

    Tracy Marshall Engel & Völkers Annapolis

    1755 Robinhood Rd, Annapolis, MD 21401
  • /35

    $825,000

    • 3 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    122 Franklin Rd, Annapolis, MD 21401

    OPEN HOUSE AUGUST 30, 1:00-3:00! Welcome home to this charming and unique property on a large private lot, tucked at the end of a quiet road in Luce Creek—just minutes from West Annapolis, the Naval Academy, the Historic District, and with easy access to Route 50 and commuter routes. This spacious home has been thoughtfully renovated to include a large primary suite with a walk-in closet and

    Deborah Laggini Long & Foster Real Estate, Inc.

    122 Franklin Rd, Annapolis, MD 21401
  • /49

    $699,999

    • 4 Beds
    • 3.5 Baths
    • 1,850 Sq Ft

    407 Merryman Rd, Annapolis, MD 21401

    we've had a price improvement! Stop by and see this beautiful home! OPEN HOUSE 8/24/25 Priced below market value!! Beautiful home in Heritage! Absolute turn-key! This home has a Wonderful, Open floor plan with 2 En Suites on the Main Level. Spacious, updated Kitchen with coffee bar, Living and Dining Area with Tons of Light. Sliding Glass Doors from the Kitchen Area to the Back Deck and on

    Leslee Borman Berkshire Hathaway HomeServices PenFed Realty

    407 Merryman Rd, Annapolis, MD 21401
  • /73

    $875,000

    • 4 Beds
    • 3 Baths
    • 4,592 Sq Ft

    2020 John Hanson Overlook, Annapolis, MD 21401

    MAJOR PRICE IMPROVEMENT!!!Welcome home to this gorgeous 4-bedroom, 3-bath home in the sought-after North River Forest neighborhood. Situated on over an acre, this property features a bright, open floor plan with two first-floor bedrooms and a full bath, plus a spacious family room with soaring ceilings, skylights, and beautiful hardwood floors. The home as been pointed up and painted, has a

    Barry Weller Barry Weller Properties, LLC

    2020 John Hanson Overlook, Annapolis, MD 21401
  • /36

    $369,950

    • 2 Beds
    • 2 Baths
    • 800 Sq Ft

    16 Parole St, Annapolis, MD 21401

    Check the photos - Beautiful * Immediate possession * Amazing opportunity to own a detached home at a condominium price * NO HOA or condo fees * Large yard * Remodeled / upgraded * Cutest cape cod with hardwood floors * screened in front porch * updated kitchen and baths * New stainless steel appliances * All solid wood cabinets with granite countertop * Freshly painted * Deep lot with plenty of

    Katie Neighoff RE/MAX United Real Estate

    16 Parole St, Annapolis, MD 21401
  • /106

    $3,250,000

    • 5 Beds
    • 4.5 Baths
    • 5,260 Sq Ft

    1486 Downham Market, Annapolis, MD 21401

    Prepare to be captivated by 1486 Downham Market, a striking architectural masterpiece perched on one of the most coveted deep-water lots in Annapolis. Perfectly situated at the mouth of Clements Creek—widely regarded as one of the safest and most protected hurricane holes on the Severn—this estate delivers a rare blend of natural beauty, luxury, and marine excellence. With a commanding 180-foot

    Wendy Oliver Coldwell Banker Realty

    1486 Downham Market, Annapolis, MD 21401
  • /35

    $580,000

    • 3 Beds
    • 3.5 Baths
    • 2,236 Sq Ft

    1809 Labrott Ln, Annapolis, MD 21401

    Great SFH situated on flag lot in desirable location! Multiple living spaces on main level, open concept kitchen and family room with high ceilings and skylights. 2 generous sized bedrooms upstairs and spacious Primary Bedroom with private En Suite. Large basement with storage, exterior access, another bedroom and full bath. Garage was converted to additional space but can easily be converted

    Heidi Heiderman Samson Properties

    1809 Labrott Ln, Annapolis, MD 21401
  • /74

    $1,235,000

    • 4 Beds
    • 3.5 Baths
    • 3,480 Sq Ft

    1580 Keswick Place, Annapolis, MD 21401

    ** Price Improvement! **Welcome to this exceptional residence in the highly coveted Downs on the Severn community, known for its premier amenities and serene setting. Enjoy access to the newly renovated marina with floating dock, kayak storage, boat launch, community clubhouse and pool, tennis courts, tot lots, walking trails, and more! The gourmet kitchen features granite countertops,

    Bob Chew Samson Properties

    1580 Keswick Place, Annapolis, MD 21401
  • /47

    $1,100,000

    • 5 Beds
    • 4 Baths
    • 3,569 Sq Ft

    553 Choptank Cove Ct, Annapolis, MD 21401

    English Tudor featuring a stone front patio for nature lovers and bird watchers. Surrounded by large trees for tons of shade and a 45 foot rear deck for large gatherings and rear lawn for play areas. Almost 4000 square feet of living space plus an oversized garage 24x25 with a floored attic space above for expansion or storage. The great room has cathedral ceilings, wood beams and wide

    Linda Patterson Long & Foster Real Estate, Inc.

    553 Choptank Cove Ct, Annapolis, MD 21401
  • /53

    $529,900

    • 2 Beds
    • 2 Baths
    • 1,434 Sq Ft

    2828 Berth Ct, Annapolis, MD 21401

    !!Price Improvement!! Charming Home in Heritage Harbour – 55+ Community Living at Its Finest!Welcome to this beautifully maintained single-family home in the highly sought-after Heritage Harbour community! Designed for comfort and convenience, this charming residence offers 2 spacious bedrooms and 2 full baths, perfect for relaxed living.Step inside to find a bright and inviting living

    Belinda Taylor EXP Realty, LLC

    2828 Berth Ct, Annapolis, MD 21401
  • /43

    $3,250,000

    • 6 Beds
    • 6.5 Baths
    • 4,750 Sq Ft

    3015 Friends Rd, Annapolis, MD 21401

    3015 Friends Road is perched on a stunning point of land where the South River meets the protected waters of Boyds Cove. The views down the South River towards the Chesapeake Bay are truly endless! This custom-built home with 456 ft of waterfrontage is everything you’d hope for in a modern waterfront retreat. Built in 2021, it blends contemporary design with the relaxed elegance of coastal living

    Reid Buckley Long & Foster Real Estate, Inc.

    3015 Friends Rd, Annapolis, MD 21401
  • /28

    $599,000

    • 3 Beds
    • 1.5 Baths
    • 1,568 Sq Ft

    111 Clay St, Annapolis, MD 21401

    Major Price Adjustment!! Great opportunity in West Annapolis! Discover the charm of 111 Clay St, a delightful 1940s Colonial offering a fantastic chance to own near Annapolis Downtown District. This home features a huge front porch, Large windows that brings in tons of natural light, to an open floor plan. Newly updated a few short years ago, this home features modern functionality and original

    Thomas Johnson Smart Realty, LLC.

    111 Clay St, Annapolis, MD 21401
  • /53

    $829,000

    • 2 Beds
    • 2.5 Baths
    • 1,708 Sq Ft

    336 Severn Rd, Annapolis, MD 21401

    Waterfront Living in Epping Forest with Stunning Views!Nestled in the exclusive, gated community of Epping Forest, this beautifully maintained 2-bedroom, 2.5-bath home offers serene water views and a relaxed yet sophisticated lifestyle. Designed for effortless living, the open floor plan features 10-foot ceilings, gleaming hardwood floors, and a cozy fireplace in the Great Room. The

    Candice Bothun CENTURY 21 New Millennium

    336 Severn Rd, Annapolis, MD 21401

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