Homes in ZIP Code 32789

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  /27

  Est $1,008,187 Not Listed For Sale

  2529 Modac Trail, Winter Park, FL 32789

  • 5 Beds
  • 3 Baths
  • 3,043 Sq Ft
  • Built 1966

  2529 Modac Trail, Winter Park, FL 32789

  Last Sold Summary

  • 6% Above List Price
  • $312/SF
  • 17 Days On Market

  Last Sold Price $949,999

  Last Listing Agent Erin Rue PALMER SCOTT PROPERTIES LLC
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  /27

  $375,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,572 Sq Ft

  958 Dupont Ave, Winter Park, FL 32789

  Welcome to 958 Dupont Ave, a home that exudes charm and functionality. The kitchen is a chef's dream, boasting all stainless steel appliances that add a sleek, modern touch. Step outside to a spacious, fenced-in backyard, perfect for privacy and outdoor activities. Enjoy leisurely afternoons or entertain on the covered patio, a delightful extension of the living space. A storage shed provides

  Karen Albright OPENDOOR BROKERAGE LLC

  958 Dupont Ave, Winter Park, FL 32789
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  /2

  $1,500,000 Sold Mar 16, 2026

  1871 Taylor Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,401 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $441/SF
  • 2 Days On Market

  Current Estimated Value $2,121,289

  Last Listing Agent Laura Earl CORCORAN PREMIER REALTY

  1871 Taylor Ave, Winter Park, FL 32789
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  /23

  Est $1,031,728 Not Listed For Sale

  1600 Alabama Dr Unit 201, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 1921

  1600 Alabama Dr Unit 201, Winter Park, FL 32789

  Last Sold Summary

  • 15% Above List Price
  • $465/SF
  • 101 Days On Market

  Last Sold Price $900,000

  Last Listing Agent Lauren Richardson FANNIE HILLMAN & ASSOCIATES
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  /68

  $2,279,000

  • 5 Beds
  • 4.5 Baths
  • 2,889 Sq Ft

  240 N Phelps Ave, Winter Park, FL 32789

  Brand new construction luxury home in the heart of Winter Park! This stunning two-story custom residence offers nearly 3,000 sq ft of heated living space with 5 bedrooms and 4 1/2 bathrooms. A soaring two-story foyer creates a dramatic first impression and opens into an expansive great room featuring 12-foot ceilings, wide-plank flooring, and abundant natural light. The family room showcases a

  Milena Fernandes GOLDEN GROUP REALTY LLC

  240 N Phelps Ave, Winter Park, FL 32789
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  /2

  $995,000 Sold Jul 22, 2025

  1821 Windsor Dr, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,188 Sq Ft
  • Built 2017

  Last Sold Summary

  • 10% Below List Price
  • $455/SF
  • 25 Days On Market

  Current Estimated Value $1,037,256

  Last Listing Agent Chris Creegan CREEGAN GROUP

  1821 Windsor Dr, Winter Park, FL 32789
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  /29

  Est $814,763 Not Listed For Sale

  1602 Alabama Dr Unit 107, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 993 Sq Ft
  • Built 1921

  1602 Alabama Dr Unit 107, Winter Park, FL 32789

  Last Sold Summary

  • 19% Below List Price
  • $1,007/SF
  • 7 Days On Market

  Last Sold Price $1,000,000

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY
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  /46

  $950,000

  • 3 Beds
  • 2.5 Baths
  • 1,884 Sq Ft

  1405 Miller Ave, Winter Park, FL 32789

  FURNISHINGS INCLUDED! Experience high-end luxury and effortless convenience in one of the most central locations in Winter Park. Built by Makeur Homes and thoughtfully updated and furnished by SMRS Design, this stunning Modern Mediterranean detached townhome showcases light-filled interiors and carefully curated custom finishes.Offering 3 bedrooms and 2.5 bathrooms across 1,884 square feet,

  Rikhil Amin FANNIE HILLMAN & ASSOCIATES

  1405 Miller Ave, Winter Park, FL 32789
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  /2

  $750,000 Sold Oct 02, 2025

  100 S Interlachen Ave Unit 203D, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft
  • Built 1971

  Last Sold Summary

  • 3% Below List Price
  • $592/SF
  • 0 Days On Market

  Last Listing Agent Michael Ford FANNIE HILLMAN & ASSOCIATES

  100 S Interlachen Ave Unit 203D, Winter Park, FL 32789
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  /2

  Est $209,051 Not Listed For Sale

  851 Miles Ave Unit 26, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Built 1984

  851 Miles Ave Unit 26, Winter Park, FL 32789

  Last Sold Summary

  • 5% Below List Price
  • $271/SF
  • 14 Days On Market

  Last Sold Price $219,000

  Last Listing Agent Kevin Mendoza CALL IT CLOSED INTL REALTY
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  /34

  $1,575,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 5 Baths
  • 2,812 Sq Ft

  607 Ellen Dr, Winter Park, FL 32789

  Discover sophisticated modern living at 607 Ellen Drive, a stunning new construction home by the acclaimed Lazarus Homes in the heart of Winter Park. This impeccably designed 2,812-square-foot residence showcases contemporary architecture with clean lines, high ceilings, and an abundance of natural light throughout. The open floor plan seamlessly connects living spaces, creating an ideal setting

  Kelly Price KELLY PRICE & COMPANY LLC

  607 Ellen Dr, Winter Park, FL 32789
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  /2

  $1,300,000 Sold Oct 02, 2025

  857 Brock St, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,288 Sq Ft
  • Built 1964

  Last Sold Summary

  • $568/SF
  • 0 Days On Market

  Current Estimated Value $1,274,299

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

  857 Brock St, Winter Park, FL 32789
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  /16

  Est $215,524 Not Listed For Sale

  851 Miles Ave Unit 28, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Built 1984

  851 Miles Ave Unit 28, Winter Park, FL 32789

  Last Sold Summary

  • 10% Below List Price
  • $296/SF
  • 43 Days On Market

  Last Sold Price $239,000

  Last Listing Agent Tom Graves FUN HOMES
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  /22

  $298,000

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft

  151 N Orlando Ave Unit 115, Winter Park, FL 32789

  Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake

  Chris Creegan CREEGAN GROUP

  151 N Orlando Ave Unit 115, Winter Park, FL 32789
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  /2

  $1,587,500 Sold Jul 31, 2025

  279 Rippling Ln, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,472 Sq Ft
  • Built 1961

  Last Sold Summary

  • 12% Below List Price
  • $457/SF
  • 318 Days On Market

  Current Estimated Value $1,605,356

  Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

  279 Rippling Ln, Winter Park, FL 32789
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  /2

  Est $193,587 Not Listed For Sale

  851 Miles Ave Unit 4, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Built 1984

  851 Miles Ave Unit 4, Winter Park, FL 32789

  Last Sold Summary

  • 3% Above List Price
  • $234/SF
  • 218 Days On Market

  Last Sold Price $188,700

  Last Listing Agent Lenny Migliaccio RE/MAX
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  /8

  $358,000

  • Land
  • 0.16 Acre
  • $2,237,500 per Acre

  2002 Indiana Ave, Winter Park, FL 32789

  Great buildable lot centrally located close to I-4 for easy access. Currently zoned R-2 for multifamily housing 2+ units possible. Please consult the zoning and planning Dept. for info and guidelines for building. The lot has single family homes on both sides of it and faces a retention pond area across the street. Front half of the lot is cleared. Back half of the lot is wooded. Paved road

  David Nicholson DAWN REALTY

  2002 Indiana Ave, Winter Park, FL 32789
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  /2

  $13,000,000 Sold Feb 24, 2026

  2203 Via Tuscany, Winter Park, FL 32789

  • 6 Beds
  • 9 Baths
  • 12,190 Sq Ft
  • Built 2002

  Last Sold Summary

  • 1% Above List Price
  • $1,066/SF
  • 4 Days On Market

  Current Estimated Value $8,622,657

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

  2203 Via Tuscany, Winter Park, FL 32789
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  /18

  Est $212,456 Not Listed For Sale

  851 Miles Ave Unit 25, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Built 1984

  851 Miles Ave Unit 25, Winter Park, FL 32789

  Last Sold Summary

  • 6% Below List Price
  • $278/SF
  • 77 Days On Market

  Last Sold Price $225,000

  Last Listing Agent Brian Hyser THE AGENCY FL
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  /5

  $3,650,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,719 Sq Ft

  207 E Kings Way, Winter Park, FL 32789

  Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  207 E Kings Way, Winter Park, FL 32789
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  /2

  $2,155,000 Sold Aug 23, 2025

  2915 Parkland Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,356 Sq Ft
  • Built 2025

  Last Sold Summary

  • $642/SF

  Current Estimated Value $2,024,453

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  2915 Parkland Dr, Winter Park, FL 32789
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  /25

  Est $502,867 Not Listed For Sale

  1545 Indiana Ave Unit A, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,606 Sq Ft
  • Built 2005

  1545 Indiana Ave Unit A, Winter Park, FL 32789

  Last Sold Summary

  • $314/SF
  • 26 Days On Market

  Last Sold Price $505,000

  Last Listing Agent Troy Stevens FLORIDA PROPERTY LLC
• 

  

  /24

  $1,050,000 Open Sat 12AM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,907 Sq Ft

  1836 Grinnell Terrace, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Beautifully renovated home in the heart of highly desirable Winter Park, surrounded by multi-million-dollar properties. Move-in ready and thoughtfully updated throughout. Set on an expansive lot approximately 79 x 152 (11,305 square feet) provides plenty of space to build your future dream home! This light-filled home features wide-plank flooring,

  Cindy Kuykendall FANNIE HILLMAN & ASSOCIATES

  1836 Grinnell Terrace, Winter Park, FL 32789
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  /2

  $1,607,160 Sold Aug 01, 2025

  1541 Chestnut Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,840 Sq Ft
  • Built 2018

  Last Sold Summary

  • 4% Above List Price
  • $566/SF
  • 2 Days On Market

  Current Estimated Value $1,597,304

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

  1541 Chestnut Ave, Winter Park, FL 32789
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  /19

  Est $215,930 Not Listed For Sale

  851 Miles Ave Unit 27, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Built 1984

  851 Miles Ave Unit 27, Winter Park, FL 32789

  Last Sold Summary

  • 8% Below List Price
  • $291/SF
  • 28 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Paula Wells PRIMAC GROUP, INC
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  /42

  $1,795,000

  • 4 Beds
  • 4 Baths
  • 2,807 Sq Ft

  1903 N Park Ave, Winter Park, FL 32789

  Completed in 2020, this beautifully designed contemporary residence on North Park Avenue offers refined finishes and seamless indoor-outdoor living just minutes from Park Avenue’s famed shopping and restaurant district as well as the vibrant retail and dining of Winter Park Village and Mills50. Positioned on a prominent corner lot with dual access from N Park Ave and N Denning Drive, the home

  Chris Creegan CREEGAN GROUP

  1903 N Park Ave, Winter Park, FL 32789
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  /2

  $690,000 Sold Feb 20, 2026

  2904 Parkland Dr, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1952

  Last Sold Summary

  • $456/SF
  • 0 Days On Market

  Current Estimated Value $571,890

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  2904 Parkland Dr, Winter Park, FL 32789
• 

  /2

  Est $193,590 Not Listed For Sale

  851 Miles Ave Unit 3, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Built 1984

  851 Miles Ave Unit 3, Winter Park, FL 32789

  Last Sold Summary

  • 2% Above List Price
  • $235/SF
  • 112 Days On Market

  Last Sold Price $190,000

  Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY
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  /34

  $725,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,008 Sq Ft

  770 W Webster Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Stop the car! Check out this classic 4/2 Florida ranch PLUS vacant lot ready for renovation! Newer roof, water heater. HW and tile floors, screened porch, utility/storage room. 1 car carport. OR develop your dream project on this hard to find R-3 lot! Adjacent 75x100 R-3 vacant lot (TAX ID 06-22-30-1168-02-023) on the south side to be purchased

  Lisa Gould KELLER WILLIAMS WINTER PARK

  770 W Webster Ave, Winter Park, FL 32789
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  /2

  $750,000 Sold Sep 25, 2025

  311 Cortland Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,382 Sq Ft
  • Built 1952

  Last Sold Summary

  • 6% Below List Price
  • $543/SF
  • 48 Days On Market

  Current Estimated Value $738,075

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  311 Cortland Ave, Winter Park, FL 32789
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  /2

  Est $219,730 Not Listed For Sale

  151 N Orlando Ave Unit 233, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft
  • Built 1960

  151 N Orlando Ave Unit 233, Winter Park, FL 32789

  Last Sold Summary

  Last Listing Agent Steve Simpson 407 PROPERTIES
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  /50

  $1,425,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,306 Sq Ft

  850 Juanita Rael, Winter Park, FL 32789

  Under contract-accepting backup offers. Location, location, location. Sought after location on the North end of Park Avenue. Avoid the traffic in and out of Downtown Winter Park while being minutes away from everything on the Avenue. One of the very few single level homes of this quality in Winter Park 32789.Single story ranch on a lovely, private, large corner lot. 2306 heated and cooled

  Brad Grosberg PHIL KEAN REAL ESTATE LLC

  850 Juanita Rael, Winter Park, FL 32789
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  /2

  $259,000 Sold Aug 29, 2025

  1250 S Denning Dr Unit 111, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft
  • Built 1967

  Last Sold Summary

  • $285/SF
  • 76 Days On Market

  Current Estimated Value $249,115

  Last Listing Agent Alayna Phillips EXP REALTY LLC

  1250 S Denning Dr Unit 111, Winter Park, FL 32789
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  /32

  Est $179,342 Not Listed For Sale

  2500 Lee Rd Unit 111, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft
  • Built 1969

  2500 Lee Rd Unit 111, Winter Park, FL 32789

  Last Sold Summary

  • 10% Below List Price
  • $309/SF
  • 31 Days On Market

  Last Sold Price $199,000

  Last Listing Agent Chris Neun CENTURY 21 ALTON CLARK
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  /67

  $1,650,000 Pending

  • 5 Beds
  • 5 Baths
  • 3,820 Sq Ft

  1705 Elizabeths Walk, Winter Park, FL 32789

  Presenting 1705 Elizabeths Walk for the first time since original construction, an exceptional custom residence located in the highly sought-after Windsong community of Winter Park. Perfectly positioned on a beautifully landscaped .34-acre lot, this elegant 5-bedroom, 5-bathroom estate offers nearly 4,000 square feet of refined living space designed for both comfortable living and sophisticated

  Keith Moore HOMEVEST REALTY

  1705 Elizabeths Walk, Winter Park, FL 32789
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  /2

  $435,000 Sold Jun 06, 2025

  693 Minnesota Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,038 Sq Ft
  • Built 2000

  Last Sold Summary

  • $419/SF

  Current Estimated Value $411,331

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  693 Minnesota Ave, Winter Park, FL 32789
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  /16

  Est $243,174 Not Listed For Sale

  1250 S Denning Dr Unit 203, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft
  • Built 1967

  1250 S Denning Dr Unit 203, Winter Park, FL 32789

  Last Sold Summary

  • 5% Below List Price
  • $281/SF
  • 18 Days On Market

  Last Sold Price $255,000

  Last Listing Agent Jane Fochler ONE LUXURY INTERNATIONAL LLC
• 

  

  /43

  $1,225,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 3 Baths
  • 2,292 Sq Ft

  67 Cypress Ln, Maitland, FL 32751

  Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This architectural gem, expertly crafted from Western Red Cedar, offers two stories of thoughtfully designed living space with 4 bedrooms and 3 full baths.Step inside to discover hardwood floors flowing

  Kelly Price KELLY PRICE & COMPANY LLC

  67 Cypress Ln, Maitland, FL 32751
• 

  /2

  $530,000 Sold Oct 02, 2025

  1409 Sunset Dr, Winter Park, FL 32789

  • 2 Beds
  • 1.5 Baths
  • 1,107 Sq Ft
  • Built 1930

  Last Sold Summary

  • 2% Above List Price
  • $479/SF
  • 4 Days On Market

  Current Estimated Value $524,384

  Last Listing Agent Ahmad Karain R MICHAELS REALTY LLC

  1409 Sunset Dr, Winter Park, FL 32789
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  /21

  Est $231,298 Not Listed For Sale

  1500 Gay Rd Unit 25A, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Built 1972

  1500 Gay Rd Unit 25A, Winter Park, FL 32789

  Last Sold Summary

  • 2% Below List Price
  • $229/SF
  • 5 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Sue Gilman KELLER WILLIAMS WINTER PARK

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