28,301

Winter Park, FL Homes

Section Image
  • /88

    $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
  • /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
    • /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

  • /64

    $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
  • /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
    • /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

  • /38

    $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
  • /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
    • /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

  • /41

    $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
  • /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
    • /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

  • /48

    $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
  • /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
    • /54

      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

  • /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
  • /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
    • /67

      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

  • /61

    $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
  • /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

Showing Results 681 - 720, Page 18 of 18

How to Buy a Home How to Finance a Home How to Sell a Home