Recently Sold Winter Park, FL Homes

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  $425,000 Sold Aug 29, 2025

  1871 Staunton Ave, Winter Park, FL 32789

  • Land
  • 0.32 Acre
  • $1,328,125 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 3 Days On Market

  Current Estimated Value $426,066

  Last Listing Agent Greg Staker WATSON REALTY CORP.

  1871 Staunton Ave, Winter Park, FL 32789
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  $475,000 Sold Sep 19, 2025

  1414 Bessmor Rd, Winter Park, FL 32789

  • Land
  • 0.16 Acre
  • $2,968,750 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 22 Days On Market

  Current Estimated Value $472,346

  Last Listing Agent Miranda Azer PARKVIEW REAL ESTATE

  1414 Bessmor Rd, Winter Park, FL 32789
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  $395,000 Sold Feb 11, 2026

  1362 Tierra Cir, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,179 Sq Ft
  • Built 1969

  Last Sold Summary

  • 10% Below List Price
  • $181/SF
  • 107 Days On Market

  Current Estimated Value $407,407

  Last Listing Agent John Muccigrosso RE/MAX 200 REALTY

  1362 Tierra Cir, Winter Park, FL 32792
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  $395,000 Sold Dec 09, 2025

  3214 Lowndes Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1965

  Last Sold Summary

  • 1% Below List Price
  • $329/SF
  • 53 Days On Market

  Current Estimated Value $391,435

  Last Listing Agent Gregory Roberts LPT REALTY LLC

  3214 Lowndes Dr, Winter Park, FL 32792
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  $335,000 Sold Jun 26, 2025

  3131 Ash Park Loop, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • Built 1986

  Last Sold Summary

  • 16% Below List Price
  • $238/SF
  • 120 Days On Market

  Current Estimated Value $337,600

  Last Listing Agent Amanda Binns STRICKLAND REALTY GROUP INC

  3131 Ash Park Loop, Winter Park, FL 32792
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  $1,025,000 Sold Jan 27, 2026

  1840 Shiloh Ln, Winter Park, FL 32789

  • Land
  • 0.27 Acre
  • $3,796,296 per Acre

  Last Sold Summary

  • 2 Days On Market

  Current Estimated Value $1,010,299

  Last Listing Agent Gwyn Clark FANNIE HILLMAN & ASSOCIATES

  1840 Shiloh Ln, Winter Park, FL 32789
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  $570,000 Sold Jan 02, 2026

  640 Killarney Bay Ct Unit 4, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,718 Sq Ft
  • Built 1986

  Last Sold Summary

  • 22% Below List Price
  • $332/SF
  • 231 Days On Market

  Current Estimated Value $492,984

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  640 Killarney Bay Ct Unit 4, Winter Park, FL 32789
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  $600,000 Sold Oct 31, 2025

  786 Antonette Ave, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 1,146 Sq Ft
  • Built 1925

  Last Sold Summary

  • 25% Below List Price
  • $524/SF
  • 200 Days On Market

  Current Estimated Value $598,673

  Last Listing Agent John Muccigrosso RE/MAX 200 REALTY

  786 Antonette Ave, Winter Park, FL 32789
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  $379,000 Sold Oct 01, 2025

  2828 Whispering Way, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,312 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $289/SF
  • 99 Days On Market

  Current Estimated Value $370,972

  Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

  2828 Whispering Way, Winter Park, FL 32792
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  $250,000 Sold Jan 16, 2026

  1605 Puritan Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,285 Sq Ft
  • Built 1963

  Last Sold Summary

  • 28% Below List Price
  • $195/SF
  • 26 Days On Market

  Current Estimated Value $322,115

  Last Listing Agent Denise San Miguel REALTY LYNK INC

  1605 Puritan Ave, Winter Park, FL 32792
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  $349,000 Sold Mar 11, 2026

  5202 Lake Howell Rd, Winter Park, FL 32792

  • 3 Beds
  • 1.5 Baths
  • 1,112 Sq Ft
  • Built 1957

  Last Sold Summary

  • $314/SF
  • 5 Days On Market

  Current Estimated Value $327,227

  Last Listing Agent Crystal Vann CHARLES RUTENBERG REALTY ORLANDO

  5202 Lake Howell Rd, Winter Park, FL 32792
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  $386,000 Sold Jul 09, 2025

  2009 Nottingdale Ln, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $244/SF
  • 6 Days On Market

  Current Estimated Value $389,063

  Last Listing Agent Wendy Calvet OLDE TOWN BROKERS INC

  2009 Nottingdale Ln, Winter Park, FL 32792
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  $1,625,000 Sold Jun 12, 2025

  1470 Place Picardy, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 4,227 Sq Ft
  • Built 2003

  Last Sold Summary

  • 17% Below List Price
  • $384/SF
  • 95 Days On Market

  Current Estimated Value $1,768,758

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

  1470 Place Picardy, Winter Park, FL 32789
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  $750,000 Sold Jun 27, 2025

  1151 Wildmeadow Run, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 2,196 Sq Ft
  • Built 2020

  Last Sold Summary

  • 3% Below List Price
  • $342/SF
  • 22 Days On Market

  Current Estimated Value $729,345

  Last Listing Agent Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

  1151 Wildmeadow Run, Winter Park, FL 32792
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  $180,000 Sold Sep 18, 2025

  200 Saint Andrews Blvd Unit 1901, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft
  • Built 1970

  Last Sold Summary

  • 10% Below List Price
  • $182/SF
  • 8 Days On Market

  Current Estimated Value $176,376

  Last Listing Agent peggy amos FANNIE HILLMAN & ASSOCIATES

  200 Saint Andrews Blvd Unit 1901, Winter Park, FL 32792
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  $750,000 Sold Nov 19, 2025

  1681 Woodland Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 2,422 Sq Ft
  • Built 1953

  Last Sold Summary

  • $310/SF

  Current Estimated Value $742,213

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

  1681 Woodland Ave, Winter Park, FL 32789
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  $550,000 Sold May 02, 2025

  2100 Suffield Dr, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,807 Sq Ft
  • Built 1960

  Last Sold Summary

  • 15% Below List Price
  • $304/SF
  • 67 Days On Market

  Current Estimated Value $542,627

  Last Listing Agent John Muccigrosso RE/MAX 200 REALTY

  2100 Suffield Dr, Winter Park, FL 32792
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  $420,000 Sold May 20, 2025

  2024 Linden Rd, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,872 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Above List Price
  • $224/SF
  • 3 Days On Market

  Current Estimated Value $425,884

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

  2024 Linden Rd, Winter Park, FL 32792
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  $310,000 Sold Feb 03, 2026

  1733 Winter Green Blvd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,548 Sq Ft
  • Built 1987

  Last Sold Summary

  • 11% Below List Price
  • $200/SF
  • 10 Days On Market

  Current Estimated Value $329,313

  Last Listing Agent TJ TAMARA FISHER Compass Florida LLC

  1733 Winter Green Blvd, Winter Park, FL 32792
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  $705,000 Sold Jul 03, 2025

  1840 Laurel Rd, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 2,245 Sq Ft
  • Built 1957

  Last Sold Summary

  • 9% Below List Price
  • $314/SF
  • 13 Days On Market

  Current Estimated Value $765,529

  Last Listing Agent Julie Glass KEYSEEKERS REAL ESTATE

  1840 Laurel Rd, Winter Park, FL 32789
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  $458,000 Sold Jul 31, 2025

  955 Minnesota Ave, Winter Park, FL 32789

  • 3 Beds
  • 1 Bath
  • 1,349 Sq Ft
  • Built 1940

  Last Sold Summary

  • 4% Below List Price
  • $340/SF
  • 4 Days On Market

  Current Estimated Value $473,898

  Last Listing Agent Cora Johnson WYNNMORE REALTY LLC

  955 Minnesota Ave, Winter Park, FL 32789
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  $490,000 Sold Jan 21, 2026

  259 Blossom Ln, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,354 Sq Ft
  • Built 1954

  Last Sold Summary

  • 8% Below List Price
  • $362/SF
  • 50 Days On Market

  Current Estimated Value $478,114

  Last Listing Agent Carlinhos Fregonezi TALENT REALTY SOLUTIONS

  259 Blossom Ln, Winter Park, FL 32789
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  $985,000 Sold Feb 03, 2026

  240 E Lake Sue Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,329 Sq Ft
  • Built 1952

  Last Sold Summary

  • 11% Below List Price
  • $741/SF
  • 50 Days On Market

  Current Estimated Value $1,069,576

  Last Listing Agent Tika Van Den Hurk Compass Florida, LLC

  240 E Lake Sue Ave, Winter Park, FL 32789
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  $409,000 Sold Jan 16, 2026

  900 Carver St, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,794 Sq Ft
  • Built 1954

  Last Sold Summary

  • 4% Below List Price
  • $228/SF
  • 10 Days On Market

  Current Estimated Value $433,981

  Last Listing Agent Tori Alexander LEGACY REALTY & BROKERS LLC

  900 Carver St, Winter Park, FL 32789
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  $418,000 Sold Dec 22, 2025

  1030 N Lakemont Ave, Winter Park, FL 32792

  • 3 Beds
  • 1.5 Baths
  • 1,050 Sq Ft
  • Built 1959

  Last Sold Summary

  • 2% Below List Price
  • $398/SF
  • 3 Days On Market

  Current Estimated Value $412,167

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

  1030 N Lakemont Ave, Winter Park, FL 32792
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  $1,875,000 Sold Jan 01, 2026

  1752 Chestnut Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,314 Sq Ft
  • Built 2021

  Last Sold Summary

  • 15% Below List Price
  • $566/SF
  • 111 Days On Market

  Current Estimated Value $1,850,101

  Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK

  1752 Chestnut Ave, Winter Park, FL 32789
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  $1,700,000 Sold Oct 29, 2025

  1181 Via Capri, Winter Park, FL 32789

  • Land
  • 0.3 Acre
  • $5,666,667 per Acre

  Last Sold Summary

  • 16 Days On Market

  Current Estimated Value $1,707,399

  Last Listing Agent Brad Grosberg PHIL KEAN REAL ESTATE LLC

  1181 Via Capri, Winter Park, FL 32789
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  $195,000 Sold Dec 08, 2025

  607 Saint Johns Ct Unit 607, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1981

  Last Sold Summary

  • 9% Below List Price
  • $174/SF
  • 69 Days On Market

  Current Estimated Value $194,347

  Last Listing Agent Allison Day RE/MAX TOWN & COUNTRY REALTY

  607 Saint Johns Ct Unit 607, Winter Park, FL 32792
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  $645,000 Sold Dec 05, 2025

  224 Overlook Rd, Winter Park, FL 32789

  • 2 Beds
  • 1.5 Baths
  • 1,399 Sq Ft
  • Built 1936

  Last Sold Summary

  • 3% Below List Price
  • $461/SF
  • 3 Days On Market

  Current Estimated Value $639,144

  Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY

  224 Overlook Rd, Winter Park, FL 32789
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  $436,000 Sold Jul 24, 2025

  5240 N Lake Burkett Ln, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 2,290 Sq Ft
  • Built 1987

  Last Sold Summary

  • 24% Below List Price
  • $190/SF
  • 224 Days On Market

  Current Estimated Value $446,039

  Last Listing Agent Ashley Harper COLDWELL BANKER REALTY

  5240 N Lake Burkett Ln, Winter Park, FL 32792
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  $420,000 Sold Dec 31, 2025

  3236 Knottypine Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,578 Sq Ft
  • Built 1981

  Last Sold Summary

  • 2% Below List Price
  • $266/SF
  • 6 Days On Market

  Current Estimated Value $416,419

  Last Listing Agent Jose Rojo URBAN-O REAL ESTATE SOLUTIONS

  3236 Knottypine Ave, Winter Park, FL 32792
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  $425,000 Sold Mar 12, 2026

  1816 Meadowgold Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,546 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $275/SF
  • 23 Days On Market

  Current Estimated Value $453,018

  Last Listing Agent Kyle Clark RE/MAX TOWN & COUNTRY REALTY

  1816 Meadowgold Ln, Winter Park, FL 32792
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  $157,500 Sold Oct 31, 2025

  150 Lewfield Cir Unit 150, Winter Park, FL 32792

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Below List Price
  • $232/SF
  • 41 Days On Market

  Last Listing Agent Randall Shirey CHARLES RUTENBERG REALTY ORLANDO

  150 Lewfield Cir Unit 150, Winter Park, FL 32792
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  $2,585,000 Sold Jun 18, 2025

  815 Bonita Dr, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 4,328 Sq Ft
  • Built 2000

  Last Sold Summary

  • $597/SF

  Current Estimated Value $2,597,072

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

  815 Bonita Dr, Winter Park, FL 32789
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  $331,985 Sold Mar 25, 2026

  638 Warrenton Rd, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,362 Sq Ft
  • Built 1984

  Last Sold Summary

  • 8% Above List Price
  • $244/SF
  • 157 Days On Market

  Current Estimated Value $325,885

  Last Listing Agent Nicholas Musashe SUN PROPERTIES, INC.

  638 Warrenton Rd, Winter Park, FL 32792
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  $625,000 Sold Jan 30, 2026

  785 Mcintyre Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,015 Sq Ft
  • Built 1987

  Last Sold Summary

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

  Current Estimated Value $618,363

  Last Listing Agent Beth Logullo KELLER WILLIAMS WINTER PARK

  785 Mcintyre Ave, Winter Park, FL 32789
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  $1,900,000 Sold Feb 20, 2026

  319 Santiago Dr, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,515 Sq Ft
  • Built 1973

  Last Sold Summary

  • 5% Below List Price
  • $541/SF
  • 104 Days On Market

  Current Estimated Value $1,918,921

  Last Listing Agent Anne Rogers ANNE ROGERS REALTY GROUP INC

  319 Santiago Dr, Winter Park, FL 32789
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  $127,000 Sold Dec 22, 2025

  1000 S Semoran Blvd Unit 716, Winter Park, FL 32792

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

  Last Sold Summary

  • 7% Below List Price
  • $160/SF
  • 131 Days On Market

  Current Estimated Value $124,087

  Last Listing Agent Nathalie Romero HOME WISE REALTY GROUP, INC.

  1000 S Semoran Blvd Unit 716, Winter Park, FL 32792
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  $800,000 Sold Jul 18, 2025

  1823 Sunset Dr, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,414 Sq Ft
  • Built 1940

  Last Sold Summary

  • 3% Above List Price
  • $331/SF
  • 0 Days On Market

  Current Estimated Value $826,222

  Last Listing Agent Sue Silberbusch COMPASS FLORIDA LLC

  1823 Sunset Dr, Winter Park, FL 32789
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  $1,640,000 Sold Sep 26, 2025

  101 S New York Ave Unit 313, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,147 Sq Ft
  • Built 2008

  Last Sold Summary

  • 3% Below List Price
  • $521/SF
  • 3 Days On Market

  Current Estimated Value $1,611,068

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

  101 S New York Ave Unit 313, Winter Park, FL 32789

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