1,127

Recently Sold Winter Park, FL Homes

Section Image
  • 451 Fairfax Ave, Winter Park, FL 32789
    451 Fairfax Ave, Winter Park, FL 32789
    /2

    $879,000 Sold Nov 14, 2025

    451 Fairfax Ave, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 2,227 Sq Ft
    • Built 2003

    Last Sold Summary

    • 2% Below List Price
    • $395/SF
    • 5 Days On Market

    Current Estimated Value $872,071

    Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    451 Fairfax Ave, Winter Park, FL 32789
  • 1792 Killarney Dr, Winter Park, FL 32789
    1792 Killarney Dr, Winter Park, FL 32789
    /2

    $630,000 Sold Aug 11, 2025

    1792 Killarney Dr, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,264 Sq Ft
    • Built 1958

    Last Sold Summary

    • 3% Below List Price
    • $278/SF
    • 1 Day On Market

    Current Estimated Value $652,518

    Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

    1792 Killarney Dr, Winter Park, FL 32789
  • 1444 Pelican Bay Trail, Winter Park, FL 32792
    1444 Pelican Bay Trail, Winter Park, FL 32792
    /2

    $965,000 Sold Mar 12, 2026

    1444 Pelican Bay Trail, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 3,121 Sq Ft
    • Built 1984

    Last Sold Summary

    • 12% Below List Price
    • $309/SF
    • 314 Days On Market

    Current Estimated Value $949,558

    Last Listing Agent Jacob Hara TRANSCEND REALTY

    1444 Pelican Bay Trail, Winter Park, FL 32792
  • 1909 Edwin Blvd, Winter Park, FL 32792
    1909 Edwin Blvd, Winter Park, FL 32792
    /2

    $382,000 Sold Jul 02, 2025

    1909 Edwin Blvd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,355 Sq Ft
    • Built 1955

    Last Sold Summary

    • 7% Below List Price
    • $282/SF
    • 34 Days On Market

    Current Estimated Value $427,606

    Last Listing Agent Brian Craib OLDE TOWN BROKERS INC

    1909 Edwin Blvd, Winter Park, FL 32792
  • 3002 George Mason Ave Unit 3, Winter Park, FL 32792
    3002 George Mason Ave Unit 3, Winter Park, FL 32792
    /2

    $89,750 Sold Dec 05, 2025

    3002 George Mason Ave Unit 3, Winter Park, FL 32792

    • 2 Beds
    • 2.5 Baths
    • 1,085 Sq Ft
    • Built 1974

    Last Sold Summary

    • 25% Below List Price
    • $83/SF
    • 92 Days On Market

    Last Listing Agent Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

    3002 George Mason Ave Unit 3, Winter Park, FL 32792
  • 422 S Ranger Blvd, Winter Park, FL 32792
    422 S Ranger Blvd, Winter Park, FL 32792
    /2

    $495,000 Sold Feb 17, 2026

    422 S Ranger Blvd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1965

    Last Sold Summary

    • 7% Below List Price
    • $295/SF
    • 77 Days On Market

    Current Estimated Value $507,925

    Last Listing Agent David Perez COLDWELL BANKER REALTY

    422 S Ranger Blvd, Winter Park, FL 32792
  • 1000 Howell Branch Rd, Winter Park, FL 32789
    1000 Howell Branch Rd, Winter Park, FL 32789
    /2

    $755,000 Sold Jul 18, 2025

    1000 Howell Branch Rd, Winter Park, FL 32789

    • Land
    • 0.55 Acre
    • $1,372,727 per Acre

    Last Sold Summary

    • 30% Below List Price
    • 241 Days On Market

    Current Estimated Value $817,704

    Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

    1000 Howell Branch Rd, Winter Park, FL 32789
  • 2020 Venetian Way, Winter Park, FL 32789
    2020 Venetian Way, Winter Park, FL 32789
    /2

    $3,845,000 Sold May 16, 2025

    2020 Venetian Way, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 4,188 Sq Ft
    • Built 1979

    Last Sold Summary

    • 4% Below List Price
    • $918/SF
    • 4 Days On Market

    Current Estimated Value $3,932,407

    Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    2020 Venetian Way, Winter Park, FL 32789
  • 200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792
    200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792
    /2

    $130,000 Sold Nov 25, 2025

    200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 727 Sq Ft
    • Built 1970

    Last Sold Summary

    • 13% Below List Price
    • $179/SF
    • 35 Days On Market

    Current Estimated Value $134,450

    Last Listing Agent Mary Marwick PREMIUM PROPERTIES R.E SERVICE

    200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792
  • 1150 Kenwood Ave, Winter Park, FL 32789
    1150 Kenwood Ave, Winter Park, FL 32789
    /2

    $975,000 Sold Feb 10, 2026

    1150 Kenwood Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,557 Sq Ft
    • Built 1988

    Last Sold Summary

    • 24% Below List Price
    • $381/SF
    • 97 Days On Market

    Current Estimated Value $1,142,505

    Last Listing Agent JJ Mackle PREMIER SOTHEBY'S INTL. REALTY

    1150 Kenwood Ave, Winter Park, FL 32789
  • 3254 Oak Lake Place Unit 137, Winter Park, FL 32792
    3254 Oak Lake Place Unit 137, Winter Park, FL 32792
    /2

    $195,000 Sold Feb 16, 2026

    3254 Oak Lake Place Unit 137, Winter Park, FL 32792

    • 2 Beds
    • 2.5 Baths
    • 1,031 Sq Ft
    • Built 1984

    Last Sold Summary

    • 22% Below List Price
    • $189/SF
    • 280 Days On Market

    Current Estimated Value $209,456

    Last Listing Agent Darryl Henderson, Jr GLOBAL ENTERPRISE REALTY GROUP

    3254 Oak Lake Place Unit 137, Winter Park, FL 32792
  • 1816 Ivy Ln, Winter Park, FL 32792
    1816 Ivy Ln, Winter Park, FL 32792
    /2

    $415,000 Sold Mar 04, 2026

    1816 Ivy Ln, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,725 Sq Ft
    • Built 1959

    Last Sold Summary

    • 8% Below List Price
    • $241/SF
    • 139 Days On Market

    Current Estimated Value $418,193

    Last Listing Agent Michael Cameron CAMERON REALTY GROUP LLC

    1816 Ivy Ln, Winter Park, FL 32792
  • 200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792
    200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792
    /2

    $170,000 Sold Sep 24, 2025

    200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,119 Sq Ft
    • Built 1970

    Last Sold Summary

    • 10% Below List Price
    • $152/SF
    • 74 Days On Market

    Current Estimated Value $175,757

    Last Listing Agent Evelyn Pilchick RE/MAX 200 REALTY

    200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792
  • 1740 Anzle Ave, Winter Park, FL 32789
    1740 Anzle Ave, Winter Park, FL 32789
    /2

    $475,000 Sold Feb 02, 2026

    1740 Anzle Ave, Winter Park, FL 32789

    • 4 Beds
    • 2 Baths
    • 1,808 Sq Ft
    • Built 1956

    Last Sold Summary

    • 40% Below List Price
    • $263/SF
    • 109 Days On Market

    Current Estimated Value $570,660

    Last Listing Agent Freddy DeCoster GOYAL & DECOSTER REALTY

    1740 Anzle Ave, Winter Park, FL 32789
  • 1438 Tierra Cir, Winter Park, FL 32792
    1438 Tierra Cir, Winter Park, FL 32792
    /2

    $350,000 Sold Feb 06, 2026

    1438 Tierra Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,627 Sq Ft
    • Built 1968

    Last Sold Summary

    • 8% Below List Price
    • $215/SF
    • 3 Days On Market

    Current Estimated Value $398,892

    Last Listing Agent Meir Tenenbaum CARDINAL REALTY GROUP, LLC.

    1438 Tierra Cir, Winter Park, FL 32792
  • 260 Killarney Bay Ct Unit 6, Winter Park, FL 32789
    260 Killarney Bay Ct Unit 6, Winter Park, FL 32789
    /2

    $325,000 Sold Oct 03, 2025

    260 Killarney Bay Ct Unit 6, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,140 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Below List Price
    • $285/SF
    • 0 Days On Market

    Current Estimated Value $324,067

    Last Listing Agent Tyler Gibson LPT REALTY, LLC

    260 Killarney Bay Ct Unit 6, Winter Park, FL 32789
  • 617 Worthington Dr, Winter Park, FL 32789
    617 Worthington Dr, Winter Park, FL 32789
    /2

    $1,725,000 Sold Mar 05, 2026

    617 Worthington Dr, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,533 Sq Ft
    • Built 2018

    Last Sold Summary

    • 13% Below List Price
    • $488/SF
    • 215 Days On Market

    Current Estimated Value $1,745,870

    Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

    617 Worthington Dr, Winter Park, FL 32789
  • 3063 Ash Park Loop, Winter Park, FL 32792
    3063 Ash Park Loop, Winter Park, FL 32792
    /2

    $415,000 Sold Jun 10, 2025

    3063 Ash Park Loop, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,673 Sq Ft
    • Built 1987

    Last Sold Summary

    • 1% Below List Price
    • $248/SF
    • 23 Days On Market

    Current Estimated Value $409,535

    Last Listing Agent Cheryl Anderson ANDERSON INVESTMENT PROPERTIES

    3063 Ash Park Loop, Winter Park, FL 32792
  • 4421 Steed Terrace, Winter Park, FL 32792
    4421 Steed Terrace, Winter Park, FL 32792
    /2

    $385,000 Sold Nov 12, 2025

    4421 Steed Terrace, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 1,788 Sq Ft
    • Built 1989

    Last Sold Summary

    • 14% Below List Price
    • $215/SF
    • 209 Days On Market

    Current Estimated Value $406,286

    Last Listing Agent Andrey Bustamante BUSTAMANTE REAL ESTATE INC

    4421 Steed Terrace, Winter Park, FL 32792
  • 2817 Prince John Rd, Winter Park, FL 32792
    2817 Prince John Rd, Winter Park, FL 32792
    /2

    $665,000 Sold Jun 18, 2025

    2817 Prince John Rd, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 2,183 Sq Ft
    • Built 1963

    Last Sold Summary

    • 5% Below List Price
    • $305/SF
    • 37 Days On Market

    Current Estimated Value $651,410

    Last Listing Agent Lori Gilmore LORI GILMORE REAL ESTATE LLC

    2817 Prince John Rd, Winter Park, FL 32792
  • 255 Stirling Ave, Winter Park, FL 32789
    255 Stirling Ave, Winter Park, FL 32789
    /2

    $2,835,000 Sold Nov 24, 2025

    255 Stirling Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 3,635 Sq Ft
    • Built 1982

    Last Sold Summary

    • 14% Below List Price
    • $780/SF
    • 25 Days On Market

    Current Estimated Value $2,831,194

    Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    255 Stirling Ave, Winter Park, FL 32789
  • 428 Selkirk Dr, Winter Park, FL 32792
    428 Selkirk Dr, Winter Park, FL 32792
    /2

    $627,000 Sold Mar 23, 2026

    428 Selkirk Dr, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 1,782 Sq Ft
    • Built 1957

    Last Sold Summary

    • 5% Below List Price
    • $352/SF
    • 103 Days On Market

    Current Estimated Value $624,915

    Last Listing Agent Sheri Malin REDFIN CORPORATION

    428 Selkirk Dr, Winter Park, FL 32792
  • 1011 Mckean Cir, Winter Park, FL 32789
    1011 Mckean Cir, Winter Park, FL 32789
    /2

    $1,430,000 Sold Nov 10, 2025

    1011 Mckean Cir, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,230 Sq Ft
    • Built 1955

    Last Sold Summary

    • $641/SF
    • 0 Days On Market

    Current Estimated Value $1,454,862

    Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

    1011 Mckean Cir, Winter Park, FL 32789
  • 1945 Bering Ave, Winter Park, FL 32789
    1945 Bering Ave, Winter Park, FL 32789
    /2

    $439,900 Sold Jul 22, 2025

    1945 Bering Ave, Winter Park, FL 32789

    • 3 Beds
    • 1.5 Baths
    • 1,576 Sq Ft
    • Built 1958

    Last Sold Summary

    • $279/SF
    • 6 Days On Market

    Current Estimated Value $444,765

    Last Listing Agent Carmen Gonzalez, Pa HORIZON WEST REALTY

    1945 Bering Ave, Winter Park, FL 32789
  • Unlisted Address
    Unlisted Address
    /2

    $799,000 Sold Apr 08, 2025

    Unlisted Address

    • 3 Beds
    • 2.5 Baths
    • 2,331 Sq Ft
    • Built 1952

    Last Sold Summary

    • $343/SF
    • 3 Days On Market

    Current Estimated Value $851,278

    Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    Unlisted Address
  • 5563 Garden Grove Cir, Winter Park, FL 32792
    5563 Garden Grove Cir, Winter Park, FL 32792
    /2

    $385,000 Sold Feb 09, 2026

    5563 Garden Grove Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,436 Sq Ft
    • Built 1988

    Last Sold Summary

    • 6% Below List Price
    • $268/SF
    • 36 Days On Market

    Current Estimated Value $407,893

    Last Listing Agent Anne Jones COLDWELL BANKER HUBBARD HANSEN

    5563 Garden Grove Cir, Winter Park, FL 32792
  • 1341 Place Picardy, Winter Park, FL 32789
    1341 Place Picardy, Winter Park, FL 32789
    /2

    $2,575,000 Sold Oct 20, 2025

    1341 Place Picardy, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 4,469 Sq Ft
    • Built 2016

    Last Sold Summary

    • 8% Below List Price
    • $576/SF
    • 95 Days On Market

    Current Estimated Value $2,552,810

    Last Listing Agent Julie Bettosini STOCKWORTH REALTY GROUP

    1341 Place Picardy, Winter Park, FL 32789
  • 2209 Fairglenn Way, Winter Park, FL 32792
    2209 Fairglenn Way, Winter Park, FL 32792
    /2

    $435,000 Sold Aug 31, 2025

    2209 Fairglenn Way, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,027 Sq Ft
    • Built 1986

    Last Sold Summary

    • 1% Below List Price
    • $215/SF
    • 54 Days On Market

    Current Estimated Value $440,485

    Last Listing Agent Benjamin Benami CHARLES RUTENBERG REALTY ORLANDO

    2209 Fairglenn Way, Winter Park, FL 32792
  • 1449 Pelican Bay Trail, Winter Park, FL 32792
    1449 Pelican Bay Trail, Winter Park, FL 32792
    /2

    $714,000 Sold Feb 25, 2026

    1449 Pelican Bay Trail, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 2,928 Sq Ft
    • Built 1982

    Last Sold Summary

    • $244/SF
    • 2 Days On Market

    Current Estimated Value $703,394

    Last Listing Agent Steven Ritz KELLER WILLIAMS WINTER PARK

    1449 Pelican Bay Trail, Winter Park, FL 32792
  • 200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792
    200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792
    /2

    $242,000 Sold Oct 15, 2025

    200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792

    • 2 Beds
    • 1.5 Baths
    • 1,219 Sq Ft
    • Built 1970

    Last Sold Summary

    • 9% Below List Price
    • $199/SF
    • 125 Days On Market

    Current Estimated Value $229,294

    Last Listing Agent Jessica Geer A+ REALTY PROFESSIONALS, INC

    200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792
  • 4200 Bear Gully Rd, Winter Park, FL 32792
    4200 Bear Gully Rd, Winter Park, FL 32792
    /2

    $535,000 Sold May 28, 2025

    4200 Bear Gully Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 1,945 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Below List Price
    • $275/SF
    • 35 Days On Market

    Current Estimated Value $526,959

    Last Listing Agent Renee Killiri RED BIRD REALTY OF FLORIDA INC

    4200 Bear Gully Rd, Winter Park, FL 32792
  • 4991 Tangerine Ave, Winter Park, FL 32792
    4991 Tangerine Ave, Winter Park, FL 32792
    /2

    $528,000 Sold Nov 25, 2025

    4991 Tangerine Ave, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,124 Sq Ft
    • Built 1972

    Last Sold Summary

    • $249/SF
    • 5 Days On Market

    Current Estimated Value $516,815

    Last Listing Agent Edwin Ayala, Jr EXP REALTY LLC

    4991 Tangerine Ave, Winter Park, FL 32792
  • 151 N Orlando Ave Unit 142, Winter Park, FL 32789
    151 N Orlando Ave Unit 142, Winter Park, FL 32789
    /2

    $140,000 Sold Apr 14, 2025

    151 N Orlando Ave Unit 142, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 582 Sq Ft
    • Built 1960

    Last Sold Summary

    • 33% Below List Price
    • $241/SF
    • 152 Days On Market

    Current Estimated Value $144,875

    Last Listing Agent Tom Noelke NOELKE REALTY

    151 N Orlando Ave Unit 142, Winter Park, FL 32789
  • 875 W Lyman Ave, Winter Park, FL 32789
    875 W Lyman Ave, Winter Park, FL 32789
    /2

    $415,000 Sold Mar 02, 2026

    875 W Lyman Ave, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 760 Sq Ft
    • Built 1925

    Last Sold Summary

    • 13% Below List Price
    • $546/SF
    • 60 Days On Market

    Current Estimated Value $431,057

    Last Listing Agent Joey Bruno CHARLES RUTENBERG REALTY ORLANDO

    875 W Lyman Ave, Winter Park, FL 32789
  • 419 W Morse Blvd, Winter Park, FL 32789
    419 W Morse Blvd, Winter Park, FL 32789
    /2

    $1,850,000 Sold Dec 15, 2025

    419 W Morse Blvd, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 3,027 Sq Ft
    • Built 2018

    Last Sold Summary

    • 5% Below List Price
    • $611/SF
    • 0 Days On Market

    Current Estimated Value $1,849,701

    Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

    419 W Morse Blvd, Winter Park, FL 32789
  • 2259 Minnesota Ave, Winter Park, FL 32789
    2259 Minnesota Ave, Winter Park, FL 32789
    /2

    $375,000 Sold Apr 28, 2025

    2259 Minnesota Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,015 Sq Ft
    • Built 1948

    Last Sold Summary

    • 10% Below List Price
    • $369/SF
    • 11 Days On Market

    Current Estimated Value $373,749

    Last Listing Agent Kayla Barnes LPT REALTY, LLC

    2259 Minnesota Ave, Winter Park, FL 32789
  • 2920 Abbey Ct, Winter Park, FL 32792
    2920 Abbey Ct, Winter Park, FL 32792
    /2

    $470,000 Sold Aug 21, 2025

    2920 Abbey Ct, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,035 Sq Ft
    • Built 1964

    Last Sold Summary

    • 6% Below List Price
    • $231/SF
    • 2 Days On Market

    Current Estimated Value $612,912

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    2920 Abbey Ct, Winter Park, FL 32792
  • 1860 Gladiolas Dr, Winter Park, FL 32792
    1860 Gladiolas Dr, Winter Park, FL 32792
    /2

    $435,000 Sold Apr 18, 2025

    1860 Gladiolas Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,653 Sq Ft
    • Built 1983

    Last Sold Summary

    • 6% Below List Price
    • $263/SF
    • 84 Days On Market

    Current Estimated Value $430,581

    Last Listing Agent James Begor COLDWELL BANKER REALTY

    1860 Gladiolas Dr, Winter Park, FL 32792
  • 2446 Lotafun Ave, Winter Park, FL 32789
    2446 Lotafun Ave, Winter Park, FL 32789
    /2

    $280,000 Sold Jun 27, 2025

    2446 Lotafun Ave, Winter Park, FL 32789

    • Land
    • 0.17 Acre
    • $1,647,059 per Acre

    Last Sold Summary

    • 7% Below List Price
    • 123 Days On Market

    Current Estimated Value $286,333

    Last Listing Agent David Francetic COLDWELL BANKER REALTY

    2446 Lotafun Ave, Winter Park, FL 32789
  • 1909 Cyril Ct, Winter Park, FL 32792
    1909 Cyril Ct, Winter Park, FL 32792
    /2

    $684,000 Sold Dec 23, 2025

    1909 Cyril Ct, Winter Park, FL 32792

    • 3 Beds
    • 3.5 Baths
    • 3,102 Sq Ft
    • Built 1990

    Last Sold Summary

    • 9% Below List Price
    • $221/SF
    • 56 Days On Market

    Current Estimated Value $690,864

    Last Listing Agent James Hurst, II JAMES F. HURST II, BROKER

    1909 Cyril Ct, Winter Park, FL 32792

Showing Results 161 - 200, Page 5 of 18

Florida Orange County Winter Park

Recently Sold Real Estate & Homes in Winter Park, FL

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