Winter Park, FL Homes

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  $1,850,000

  • 5 Beds
  • 4.5 Baths
  • 3,851 Sq Ft

  1560 Woodland Ave, Winter Park, FL 32789

  Welcome to a one-of-a-kind opportunity inside the Winter Park city limits, where timeless character, meaningful updates, and an exceptional lifestyle and location come together in a perfect blend! Set on a beautifully landscaped 0.27-acre lot along Winter Park’s iconic tree lined, brick paved streets, this custom 5-bedroom, 4.5-bathroom residence with an office, a gym and attached in-law suite

  Chris Creegan CREEGAN GROUP

  1560 Woodland Ave, Winter Park, FL 32789
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  $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
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  /18

  Est $191,144 Not Listed For Sale

  7413 Belle River Ct Unit 3, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,151 Sq Ft
  • Built 1983

  7413 Belle River Ct Unit 3, Winter Park, FL 32792

  Last Sold Summary

  • 20% Below List Price
  • $209/SF
  • 2 Days On Market

  Last Sold Price $240,000

  Last Listing Agent John Goggin STOCKWORTH REALTY GROUP
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  $2,195,000

  • 3 Beds
  • 3.5 Baths
  • 2,714 Sq Ft

  660 Osceola Ave Unit 101, Winter Park, FL 32789

  Imagine waking, relaxing, and entertaining with serene lakefront views in this elegant ground-floor Perle du Lac residence. The refined 2,714-square-foot design includes hardwood and travertine flooring, ten-foot-high ceilings, and extensive millwork. The expansive open-plan living and dining room lets you configure your furniture however you’d like. A bank of glass doors leads to your covered

  Richard Traynor FLORIDA ONE REAL ESTATE LLC

  660 Osceola Ave Unit 101, Winter Park, FL 32789
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  $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
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  /5

  Est $417,456 Not Listed For Sale

  7494 Betty St, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,477 Sq Ft
  • Built 2023

  7494 Betty St, Winter Park, FL 32792

  Last Sold Summary

  • 7% Below List Price
  • $305/SF
  • 52 Days On Market

  Last Sold Price $450,000

  Last Listing Agent Douglas Herrold LIGHTHOUSE PROPERTY GRP INC
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  $3,800,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 3,413 Sq Ft

  1120 Palmer Ave, Winter Park, FL 32789

  Miami Beach/Coral Gables meets Winter Park high-end luxury for today's upscale lifestyle. Phil Kean completely re-imagined this 3400 sq ft one story home from top to bottom leaving virtually nothing untouched! If you are looking for one level living, all of the most up-to-date Bells and Whistles, in a #10 location, this will blow your socks off! Available to tour by appointment only. This is a

  Brad Grosberg PHIL KEAN REAL ESTATE LLC

  1120 Palmer Ave, Winter Park, FL 32789
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  $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
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  /3

  Est $2,242,616 Not Listed For Sale

  150 Whipple Ave, Winter Park, FL 32789

  • 4 Beds
  • Built 2025

  150 Whipple Ave, Winter Park, FL 32789

  Last Sold Summary

  • 15% Above List Price
  • $443/SF
  • 0 Days On Market

  Last Sold Price $1,950,000

  Last Listing Agent Adam Cole COLEDEV REAL ESTATE LLC
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  $1,550,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,985 Sq Ft

  507 Country Club Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Designed for elevated living in the heart of Winter Park, this custom-built pool home on the largest interior lot in the community combines timeless craftsmanship, modern comfort, and an unbeatable location just steps from premier shopping and dining. Featuring 4 bedrooms, 3.5 bathrooms, a private pool, and a spacious backyard, this stunning home is

  Lianna D'Angelo SOTERA LIVING

  507 Country Club Dr, Winter Park, FL 32789
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  $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
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  /2

  Est $761,801 Not Listed For Sale

  2352 Kestrel Perch Place, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 3,094 Sq Ft
  • Built 2023

  2352 Kestrel Perch Place, Winter Park, FL 32792

  Last Sold Summary

  • 2% Above List Price
  • $242/SF
  • 28 Days On Market

  Last Sold Price $750,000

  Last Listing Agent Angela Fettig KELLER WILLIAMS REALTY AT THE PARKS
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  $4,950,000 New Construction

  • 5 Beds
  • 6.5 Baths
  • 6,406 Sq Ft

  1660 Palmer Ave, Winter Park, FL 32789

  New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1660 Palmer Ave, Winter Park, FL 32789
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  $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
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  Est $775,410 Not Listed For Sale

  1155 Wildmeadow Run, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 2,894 Sq Ft
  • Built 2020

  1155 Wildmeadow Run, Winter Park, FL 32792

  Last Sold Summary

  • 7% Above List Price
  • $251/SF
  • 4 Days On Market

  Last Sold Price $726,700

  Last Listing Agent Jorge Perez Gonzalez TBRO REALTY 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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  $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
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  Est $1,281,495 Not Listed For Sale

  1464 Via Sangro Place, Winter Park, FL 32792

  • 7 Beds
  • 5 Baths
  • 5,111 Sq Ft
  • Built 2015

  1464 Via Sangro Place, Winter Park, FL 32792

  Last Sold Summary

  • 7% Above List Price
  • $235/SF
  • 18 Days On Market

  Last Sold Price $1,200,000

  Last Listing Agent Kimberley Beaudry ORLANDO REGIONAL REALTY
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  $1,699,000

  • 4 Beds
  • 3 Baths
  • 3,142 Sq Ft

  1016 Howell Branch Rd, Winter Park, FL 32789

  Canal Front Oasis on the Winter Park Chain of Lakes! (Seller Financing Available for Qualified Buyers) Welcome to 1016 Howell Branch Road, where every day feels like a getaway. This beautifully reimagined 4-bedroom, 3-bath residence offers 3,142 square feet of inspired living space set amid lush, tropical landscaping — all within the best of Winter Park and Maitland. *The canal allows for full

  Andrew Birr PLAID PROPERTIES, LLC

  1016 Howell Branch Rd, Winter Park, FL 32789
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  $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

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