Maitland, FL Homes

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  $417,500 Sold May 19, 2025

  2295 Park Maitland Ct, Maitland, FL 32751

  • 3 Beds
  • 2.5 Baths
  • 1,742 Sq Ft
  • Built 2002

  Last Sold Summary

  • 6% Below List Price
  • $240/SF
  • 174 Days On Market

  Current Estimated Value $424,513

  Last Listing Agent Christopher Soucy REALTY ONE GROUP MVP

  2295 Park Maitland Ct, Maitland, FL 32751
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  Not Listed For Sale

  1000 S Orlando Ave Unit A24, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft
  • Built 1964

  1000 S Orlando Ave Unit A24, Maitland, FL 32751

  Last Sold Summary

  • $320/SF
  • 28 Days On Market

  • Last Sold Price $305,000
  • Jul 26, 2024

  Last Listing Agent Joann Beck BECK REALTY LLC
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  /10

  $2,000,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 3,695 Sq Ft

  103 Whitecaps Cir, Maitland, FL 32751

  Under contract-accepting backup offers. Under Construction. A striking blend of refined luxury and sleek contemporary architecture, this exceptional new construction residence is set to be completed in July 2026. Designed for effortless living and elevated entertaining, the home showcases 5 well-proportioned bedrooms, 4.5 designer bathrooms, and approximately 3,695 square feet of thoughtfully

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  103 Whitecaps Cir, Maitland, FL 32751
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  $396,000 Sold Jun 13, 2025

  1379 Benevolent St, Maitland, FL 32751

  • 3 Beds
  • 2.5 Baths
  • 1,789 Sq Ft
  • Built 2005

  Last Sold Summary

  • 1% Below List Price
  • $221/SF
  • 14 Days On Market

  Current Estimated Value $391,953

  Last Listing Agent John Stearns EXP REALTY LLC

  1379 Benevolent St, Maitland, FL 32751
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  Est $472,108 Not Listed For Sale

  202 Quayside Cir Unit 201, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,203 Sq Ft
  • Built 1984

  202 Quayside Cir Unit 201, Maitland, FL 32751

  Last Sold Summary

  • 9% Above List Price
  • $361/SF
  • 64 Days On Market

  • Last Sold Price $434,000
  • Oct 03, 2024

  Last Listing Agent Francis Gilman KELLER WILLIAMS WINTER PARK
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  $1,249,900

  • 4 Beds
  • 4 Baths
  • 3,902 Sq Ft

  873 Cranes Ct, Maitland, FL 32751

  Beautifully Maintained Original-Owner Pool Home in Gated Lake Sybelia Cove. Pride of ownership shines throughout this beautifully maintained original-owner home tucked away on a quiet cul-de-sac in the gated community of Sybelia Cove. Offering 4 bedrooms, 4 bathrooms, a side-entry 3-car garage, and 3,902 square feet, this spacious residence blends timeless design with thoughtful updates in one of

  Chris Creegan CREEGAN GROUP

  873 Cranes Ct, Maitland, FL 32751
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  $435,000 Sold Jun 05, 2025

  2632 Derbyshire Rd, Maitland, FL 32751

  • 4 Beds
  • 2 Baths
  • 1,767 Sq Ft
  • Built 1966

  Last Sold Summary

  • 5% Below List Price
  • $246/SF
  • 2 Days On Market

  Current Estimated Value $502,937

  Last Listing Agent Pat Long FLORIDA HOME TEAM REALTY LLC

  2632 Derbyshire Rd, Maitland, FL 32751
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  Not Listed For Sale

  1140 S Orlando Ave Unit K9, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,246 Sq Ft
  • Built 1966

  1140 S Orlando Ave Unit K9, Maitland, FL 32751

  Last Sold Summary

  • $401/SF
  • 0 Days On Market

  • Last Sold Price $500,000
  • Feb 19, 2024

  Last Listing Agent Lisa Shear FANNIE HILLMAN & ASSOCIATES
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  $599,000

  • 4 Beds
  • 3.5 Baths
  • 2,477 Sq Ft

  1161 Charming St, Maitland, FL 32751

  Sunrises over Lake Charity, two primary suites, and a kitchen made for serious cooking — this Montacino townhouse isn’t like anything else on the market. With 4 bedrooms, 3.5 baths, and new luxury vinyl flooring throughout, it’s effortlessly modern and move-in ready. The first-floor primary suite offers single-level living with a spa-inspired bathroom with two vanities, a tub and shower and

  Allie George CORCORAN PREMIER REALTY

  1161 Charming St, Maitland, FL 32751
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  $525,000 Sold Sep 18, 2025

  503 Lake Shore Dr, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 2,054 Sq Ft
  • Built 1959

  Last Sold Summary

  • $256/SF
  • 17 Days On Market

  Current Estimated Value $517,306

  Last Listing Agent Tanya McDonnell RE/MAX TOWN & COUNTRY REALTY

  503 Lake Shore Dr, Maitland, FL 32751
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  Not Listed For Sale

  1000 S Orlando Ave Unit A26, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft
  • Built 1964

  1000 S Orlando Ave Unit A26, Maitland, FL 32751

  Last Sold Summary

  • $367/SF
  • 64 Days On Market

  • Last Sold Price $349,000
  • May 14, 2024

  Last Listing Agent David Perez COLDWELL BANKER REALTY
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  /25

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,538 Sq Ft

  1000 Winderley Place Unit 226, Maitland, FL 32751

  Welcome to this beautifully maintained 3-bedroom, 2-bath condo located in the highly desirable Sun Bay Club in Maitland. Offering 1,538 square feet of living space, this second-floor unit combines comfort, style, and convenience in a serene, gated community setting. Step inside to an impressive open floor plan featuring soaring 20-foot ceilings that create a bright and airy atmosphere, seamlessly

  CeCe Mercado INVESTOR'S REAL ESTATE LLC

  1000 Winderley Place Unit 226, Maitland, FL 32751
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  $251,500 Sold Oct 28, 2025

  1140 S Orlando Ave Unit F9, Maitland, FL 32751

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft
  • Built 1969

  Last Sold Summary

  • 1% Above List Price
  • $308/SF
  • 2 Days On Market

  Last Listing Agent Allie George CORCORAN PREMIER REALTY

  1140 S Orlando Ave Unit F9, Maitland, FL 32751
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  Not Listed For Sale

  1000 S Orlando Ave Unit A4, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft
  • Built 1964

  1000 S Orlando Ave Unit A4, Maitland, FL 32751

  Last Sold Summary

  • $404/SF
  • 19 Days On Market

  • Last Sold Price $385,000
  • Feb 14, 2024

  Last Listing Agent Laura Napoleon KELLER WILLIAMS WINTER PARK
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  /25

  $119,000

  • 1 Bed
  • 1 Bath
  • 759 Sq Ft

  480 Banyon Tree Cir Unit 102, Maitland, FL 32751

  PRICE REDUCED! Great condo to hold as an investment property or first-time purchase. The one-bed condo at Carrington Park has ceramic tile floors throughout. Ground floor unit with fresh paint and large open living room. Community offers three pools, fitness center, clubhouse, playground, park/picnic spaces and more! Excellent location in Maitland and convenient to shopping, restaurants and the

  Travis Stone BENOIT MANAGEMENT LLC

  480 Banyon Tree Cir Unit 102, Maitland, FL 32751
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  $515,000 Sold May 22, 2025

  1913 South Blvd, Maitland, FL 32751

  • 4 Beds
  • 3 Baths
  • 2,416 Sq Ft
  • Built 1969

  Last Sold Summary

  • 12% Below List Price
  • $213/SF
  • 243 Days On Market

  Current Estimated Value $512,538

  Last Listing Agent Juan Rijos LA ROSA REALTY ORLANDO LLC

  1913 South Blvd, Maitland, FL 32751
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  Not Listed For Sale

  1140 S Orlando Ave Unit H16, Maitland, FL 32751

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft
  • Built 1964

  1140 S Orlando Ave Unit H16, Maitland, FL 32751

  Last Sold Summary

  • $312/SF
  • 0 Days On Market

  • Last Sold Price $255,000
  • Jun 02, 2023

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
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  $918,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,500 Sq Ft

  535 Pawnee Trail, Maitland, FL 32751

  Under contract-accepting backup offers. Welcome to your dream home! This beautifully updated 4-bedroom, 3 bath residence is in one of the area's most desirable neighborhoods. Enjoy a perfect blend of comfort, style, and functionality, complete with modern renovations and exceptional outdoor living spaces. This corner lot home with multiple picturesque windows provides an abundance of natural

  Shirley Welch BHHS FLORIDA REALTY

  535 Pawnee Trail, Maitland, FL 32751
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  $505,000 Sold Aug 26, 2025

  2089 Sunderland Rd, Maitland, FL 32751

  • 4 Beds
  • 2 Baths
  • 1,627 Sq Ft
  • Built 1963

  Last Sold Summary

  • 4% Below List Price
  • $310/SF
  • 22 Days On Market

  Current Estimated Value $489,114

  Last Listing Agent Ahmad Hassan COMPASS FLORIDA LLC

  2089 Sunderland Rd, Maitland, FL 32751
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  Est $251,754 Not Listed For Sale

  1140 S Orlando Ave Unit H12, Maitland, FL 32751

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • Built 1966

  1140 S Orlando Ave Unit H12, Maitland, FL 32751

  Last Sold Summary

  • 3% Above List Price
  • $300/SF
  • 4 Days On Market

  • Last Sold Price $245,000
  • Oct 31, 2023

  Last Listing Agent Margo Rochelle Weichert Corporate
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  $525,000

  • 4 Beds
  • 3 Baths
  • 2,748 Sq Ft

  140 E Faith Terrace, Maitland, FL 32751

  One or more photo(s) has been virtually staged. NEW ROOF 2022 - NEW AC 2022 - NEW ELECTRICAL PANELS 2022 - REPLUMB 2022 - NEW SEPTIC 2023 - Seperate detached GUEST HOUSE offering built-in monthly income potential. Previously rented under market value at $900/month, the guesthouse is currently vacant and ready for a new tenant, a private space for adult children, or a comfortable in-law suite.

  Gregory Roberts LPT REALTY LLC

  140 E Faith Terrace, Maitland, FL 32751
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  $2,850,000 Sold Sep 12, 2025

  640 Old Horatio Ave, Maitland, FL 32751

  • 5 Beds
  • 4 Baths
  • 4,042 Sq Ft
  • Built 2025

  Last Sold Summary

  • 17% Below List Price
  • $705/SF
  • 156 Days On Market

  Current Estimated Value $2,852,487

  Last Listing Agent Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  640 Old Horatio Ave, Maitland, FL 32751
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  Not Listed For Sale

  1140 S Orlando Ave Unit E3, Maitland, FL 32751

  • 1 Bed
  • 1 Bath
  • 612 Sq Ft
  • Built 1971

  1140 S Orlando Ave Unit E3, Maitland, FL 32751

  Last Sold Summary

  • $319/SF
  • 23 Days On Market

  • Last Sold Price $195,000
  • Dec 29, 2023

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC
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  $999,999 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,116 Sq Ft

  1421 Sunnyside Dr, Maitland, FL 32751

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Priced below appraised value for a limited opportunity to capture instant equity. Welcome to 1421 Sunnyside Drive, Maitland, FL, a beautifully maintained 4-bedroom, 2.5-bath single-family home with a pool, located on a corner lot directly adjacent to Winter Park. While this home carries a Maitland address, it

  Amanda Binns STRICKLAND REALTY GROUP INC

  1421 Sunnyside Dr, Maitland, FL 32751
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  $250,000 Sold Aug 22, 2025

  20 People St, Maitland, FL 32751

  • Land
  • 25,264 Sq Ft
  • $431,034 per Acre

  Last Sold Summary

  • 10 Days On Market

  Current Estimated Value $245,260

  Last Listing Agent Julia Meffen FLORIDA HOMES & LOANS INC.

  20 People St, Maitland, FL 32751
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  Not Listed For Sale

  1140 S Orlando Ave Unit A14, Maitland, FL 32751

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • Built 1964

  1140 S Orlando Ave Unit A14, Maitland, FL 32751

  Last Sold Summary

  • $276/SF
  • 139 Days On Market

  • Last Sold Price $225,000
  • May 06, 2024

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC
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  /23

  $525,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,655 Sq Ft

  1529 Glastonberry Rd, Maitland, FL 32751

  Under contract-accepting backup offers. Welcome to 1529 Glastonberry Rd, a 4 bedroom, 2 bath pool home in the heart of Maitland. You will love this tastefully updated home. Upon entering, you will love the open floor plan and the way the homes flows from the spacious living room to the airy dining room straight into the bright, sparkling kitchen with stainless steel appliances. The whole area

  Tamara Rorman RE/MAX TOWN CENTRE

  1529 Glastonberry Rd, Maitland, FL 32751
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  $235,000 Sold Aug 14, 2025

  1140 S Orlando Ave Unit K15, Maitland, FL 32751

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft
  • Built 1966

  Last Sold Summary

  • 24% Below List Price
  • $288/SF
  • 194 Days On Market

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1140 S Orlando Ave Unit K15, Maitland, FL 32751
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  Est $309,764 Not Listed For Sale

  210 Magnolia Rd Unit 110, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Built 1971

  210 Magnolia Rd Unit 110, Maitland, FL 32751

  Last Sold Summary

  • 3% Below List Price
  • $320/SF
  • 9 Days On Market

  • Last Sold Price $320,000
  • Nov 01, 2024

  Last Listing Agent Moe Mossa SAVVY AVENUE, LLC
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  $398,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  344 Banyan Dr, Maitland, FL 32751

  STUNNING MODERN REVIVAL IN THE HEART OF MAITLAND. Welcome to 344 Banyan Drive, where classic Maitland charm meets contemporary elegance. Experience the pinnacle of move-in-ready luxury at 344 Banyan Dr. This impeccably renovated residence has been transformed from top to bottom with sophisticated finishes and meticulous attention to detail. The open-concept interior shines with all-new flooring,

  ketan patel REMAX SUNSTATE REALTY

  344 Banyan Dr, Maitland, FL 32751
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  $379,000 Sold Dec 29, 2025

  518 Oak Ln, Maitland, FL 32751

  • 3 Beds
  • 3 Baths
  • 1,999 Sq Ft
  • Built 1957

  Last Sold Summary

  • 10% Below List Price
  • $190/SF
  • 21 Days On Market

  Current Estimated Value $388,580

  Last Listing Agent Sonia Dublis COLDWELL BANKER REALTY

  518 Oak Ln, Maitland, FL 32751
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  Est $259,005 Not Listed For Sale

  1000 Winderley Place Unit 146, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1985

  1000 Winderley Place Unit 146, Maitland, FL 32751

  Last Sold Summary

  • 10% Above List Price
  • $178/SF
  • 27 Days On Market

  • Last Sold Price $235,000
  • Jul 17, 2023

  Last Listing Agent Casey Zamsky UNITED REAL ESTATE PREFERRED
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  $509,900

  • 3 Beds
  • 3 Baths
  • 1,683 Sq Ft

  370 Sultana Ln, Maitland, FL 32751

  Welcome to 370 Sultana Lane, a beautifully renovated 3-bedroom, 2-bathroom home located in the highly desirable Druid Hills community of Maitland. With over $60,000 in thoughtful upgrades, this move-in-ready residence offers modern comfort without the hassle of future projects. Step inside to a fully reimagined open floor plan designed for both everyday living and entertaining. A redesigned foyer

  Melissa Osborne EQUITYPRO LLC

  370 Sultana Ln, Maitland, FL 32751
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  $678,500 Sold Jul 18, 2025

  1921 Geronimo Trail, Maitland, FL 32751

  • 4 Beds
  • 3 Baths
  • 2,167 Sq Ft
  • Built 1970

  Last Sold Summary

  • $313/SF
  • 4 Days On Market

  Current Estimated Value $681,928

  Last Listing Agent Kayla Watson COMPASS FLORIDA LLC

  1921 Geronimo Trail, Maitland, FL 32751
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  Est $287,951 Not Listed For Sale

  1000 Winderley Place Unit 240, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,538 Sq Ft
  • Built 1982

  1000 Winderley Place Unit 240, Maitland, FL 32751

  Last Sold Summary

  • $187/SF

  • Last Sold Price $288,000

  Last Listing Agent Desiree Lugo Arroyo EXP Realty, LLC
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  $799,000

  • 3 Beds
  • 2 Baths
  • 2,375 Sq Ft

  2040 Geronimo Trail, Maitland, FL 32751

  One or more photo(s) has been virtually staged. Set on one of the most sought-after streets in Dommerich, this completely renovated home combines the solid construction of a 1963 block home with thoughtful modern updates throughout. From the moment you arrive, the circular driveway, classic brick accents, and welcoming front porch set the tone. Inside, a bright foyer opens to beautiful solid

  Maria Van Warner FANNIE HILLMAN & ASSOCIATES

  2040 Geronimo Trail, Maitland, FL 32751
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  $340,000 Sold Jan 16, 2026

  2352 Sierra Ln, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,343 Sq Ft
  • Built 1984

  Last Sold Summary

  • $253/SF
  • 6 Days On Market

  Current Estimated Value $335,984

  Last Listing Agent Shirley Welch BHHS FLORIDA REALTY

  2352 Sierra Ln, Maitland, FL 32751
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  Est $211,923 Not Listed For Sale

  1100 Lake Shadow Cir Unit 2305, Maitland, FL 32751

  • 2 Beds
  • 2 Baths
  • 1,048 Sq Ft
  • Built 2000

  1100 Lake Shadow Cir Unit 2305, Maitland, FL 32751

  Last Sold Summary

  • 7% Below List Price
  • $217/SF
  • 39 Days On Market

  • Last Sold Price $227,900
  • Feb 03, 2025

  Last Listing Agent Lisa Hoad HOAD REALTY GROUP LLC
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  $385,000 Pending

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  1140 S Orlando Ave Unit F1, Maitland, FL 32751

  Under contract-accepting backup offers. This condo was completely renovated in 2023 and is located in one of the best spots within the complex. Positioned directly on the Winter Park chain of lakes, it offers excellent access to everything Winter Park and Maitland have to offer. Residents enjoy being within walking distance to a variety of restaurants and shopping, creating an ideal blend of

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1140 S Orlando Ave Unit F1, Maitland, FL 32751
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  $410,000 Sold Sep 05, 2025

  2132 Tortoise Shell Dr, Maitland, FL 32751

  • 4 Beds
  • 2 Baths
  • 1,809 Sq Ft
  • Built 1996

  Last Sold Summary

  • 4% Below List Price
  • $227/SF
  • 15 Days On Market

  Current Estimated Value $404,214

  Last Listing Agent Gale Milgrim KELLER WILLIAMS WINTER PARK

  2132 Tortoise Shell Dr, Maitland, FL 32751

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