28,340

Winter Park, FL Homes

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    • /11

      Not Listed For Sale

      0 Dodd Rd Unit MFRO6144077, Winter Park, FL 32792

      0 Dodd Rd Unit MFRO6144077, Winter Park, FL 32792

      Last Sold Summary

      • 8 Days On Market
      • Last Sold Price $417,500
      • Nov 29, 2023

      Last Listing Agent John Muccigrosso RE/MAX

  • /57

    $1,870,000

    • 5 Beds
    • 4.5 Baths
    • 4,363 Sq Ft

    1177 Kenwood Ave, Winter Park, FL 32789

    Welcome to 1177 Kenwood Ave, a home that blends warmth, comfort, and thoughtful design. The inviting living room features a cozy fireplace, creating the perfect space to relax on cooler evenings. The kitchen is designed with both style and function in mind, stainless steel appliances and a center island ideal for meal preparation and gathering. The spacious primary suite serves as a retreat,

    Karen Albright OPENDOOR BROKERAGE LLC

    1177 Kenwood Ave, Winter Park, FL 32789
  • /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
    • /11

      Est $454,003 Not Listed For Sale

      2737 Bright Bird Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,782 Sq Ft
      • Built 2023
      2737 Bright Bird Ln, Winter Park, FL 32792

      Last Sold Summary

      • 5% Below List Price
      • $268/SF
      • 110 Days On Market
      • Last Sold Price $477,790
      • Feb 16, 2024

      Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES

  • /61

    $2,394,500 New Construction

    • 5 Beds
    • 6.5 Baths
    • 4,506 Sq Ft

    2412 Chantilly Ave, Winter Park, FL 32789

    Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom glass front door into the foyer leading to your main living area featuring a fireplace and sliding glass walls for indoor-outdoor living. This

    Tab Bish LLC REAL BROKER, LLC

    2412 Chantilly Ave, Winter Park, FL 32789
  • /2

    $625,000 Sold Mar 27, 2026

    1500 Berkshire Ave, Winter Park, FL 32789

    • 3 Beds
    • 1.5 Baths
    • 1,485 Sq Ft
    • Built 1925

    Last Sold Summary

    • $421/SF
    • 51 Days On Market

    Current Estimated Value $614,957

    Last Listing Agent Lianna D'Angelo SOTERA LIVING

    1500 Berkshire Ave, Winter Park, FL 32789
    • /2

      Est $6,222,655 Not Listed For Sale

      654 W Morse Blvd, Winter Park, FL 32789

      • 5 Beds
      • 7.5 Baths
      • 8,752 Sq Ft
      • Built 2022
      654 W Morse Blvd, Winter Park, FL 32789

      Last Sold Summary

      • 3% Above List Price
      • $691/SF
      • 120 Days On Market
      • Last Sold Price $6,050,000
      • Feb 10, 2025

      Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  • /23

    $339,000

    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    1760 Peruvian Ln, Winter Park, FL 32792

    Winter Park “Sweet Spot”, Priced to Sell: Rare 3/2 Opportunity in Eastbrook Discover the perfect blend of value, location, and versatility in Winter Park’s highly sought-after Eastbrook neighborhood. This 3-bedroom, 2-bathroom home is ideal for homebuyers looking to make new memories or savvy investors seeking a turn-key property. Move-in Ready: From the moment you step inside this roomy, open

    Moe Mossa SAVVY AVENUE, LLC

    1760 Peruvian Ln, Winter Park, FL 32792
  • /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 $1,449,623

    Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

    1011 Mckean Cir, Winter Park, FL 32789
    • /21

      Est $440,832 Not Listed For Sale

      2861 Clever Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,907 Sq Ft
      • Built 2023
      2861 Clever Ln, Winter Park, FL 32792

      Last Sold Summary

      • 4% Above List Price
      • $221/SF
      • 1 Day On Market
      • Last Sold Price $421,990
      • Oct 23, 2023

      Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC

  • /21

    $129,900

    • 2 Beds
    • 2 Baths
    • 1,030 Sq Ft

    3053 George Mason Ave Unit 8, Winter Park, FL 32792

    Updated 2-bedroom, 2-bath condo featuring modern finishes throughout! This condo features laminate floors, sleek granite countertops, and stainless steel appliances in the kitchen. A rare find with an in-unit washer and dryer for added convenience. Step out onto the brand new deck, upgraded with durable composite decking—perfect for relaxing or entertaining. Ideally located just minutes from Full

    Daniel Graves GRAVES REALTY

    3053 George Mason Ave Unit 8, Winter Park, FL 32792
  • /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 $439,314

    Last Listing Agent Carmen Gonzalez, Pa HORIZON WEST REALTY

    1945 Bering Ave, Winter Park, FL 32789
    • /23

      Est $296,432 Not Listed For Sale

      3197 Crown Jewel Ct, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,408 Sq Ft
      • Built 2019
      3197 Crown Jewel Ct, Winter Park, FL 32792

      Last Sold Summary

      • 13% Below List Price
      • $241/SF
      • 23 Days On Market
      • Last Sold Price $340,000
      • Oct 20, 2023

      Last Listing Agent Priscilla Chan FLORIDA REALTY INVESTMENTS

  • /31

    $599,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,556 Sq Ft

    1951 Staunton Ave, Winter Park, FL 32789

    Under contract-accepting backup offers. TRANSFERABLE TERMITE BOND INCLUDED. Welcome home to the charm and character of the bygone days. This 3-bedroom, 2-bathroom home offers 2,556 square feet, with the historic main home originally built in 1922. Featuring original antique wood floors, a classic fireplace, and a one of a kind upstairs loft, there's nothing quite like it! A charming front porch

    Veronica Figueroa EXP REALTY LLC

    1951 Staunton Ave, Winter Park, FL 32789
  • /2

    $570,000 Sold May 04, 2026

    1537 Bantam Way, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 2,312 Sq Ft
    • Built 2022

    Last Sold Summary

    • 20% Above List Price
    • $247/SF
    • 3 Days On Market

    Current Estimated Value $471,365

    Last Listing Agent Jared Dunn LIVE MVRK LLC

    1537 Bantam Way, Winter Park, FL 32792
    • /32

      Est $588,558 Not Listed For Sale

      1178 Wildmeadow Run, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,770 Sq Ft
      • Built 2021
      1178 Wildmeadow Run, Winter Park, FL 32792

      Last Sold Summary

      • 2% Below List Price
      • $340/SF
      • 6 Days On Market
      • Last Sold Price $601,000
      • Oct 27, 2023

      Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  • /64

    $444,900

    • 3 Beds
    • 2.5 Baths
    • 1,782 Sq Ft

    1951 Canny Cove, Winter Park, FL 32792

    Welcome to easy, light-filled living in this beautifully maintained 3-bedroom, 2.5-bath corner townhome in the gated Grayson Square community. Freshly painted and designed for comfort, the open living and dining spaces feel bright and inviting, flowing effortlessly to a covered lanai—perfect for relaxing evenings or casual gatherings. The kitchen offers a clean, modern look with stainless steel

    Denise Del Castillo LPT REALTY, LLC

    1951 Canny Cove, 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 $391,042

    Last Listing Agent Anne Jones COLDWELL BANKER HUBBARD HANSEN

    5563 Garden Grove Cir, Winter Park, FL 32792
    • /18

      Not Listed For Sale

      1411 Miller Ave, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 1,813 Sq Ft
      • Built 2023
      1411 Miller Ave, Winter Park, FL 32789

      Last Sold Summary

      • $430/SF
      • 30 Days On Market
      • Last Sold Price $779,900
      • Nov 14, 2023

      Last Listing Agent Kimberly Griffin RE/MAX

  • /17

    $6,950,000 New Construction

    • 5 Beds
    • 5.5 Baths
    • 5,905 Sq Ft

    40 Palmer Ave, Winter Park, FL 32789

    Under Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer represents a rare convergence of architectural significance, uncompromising craftsmanship, and premier Winter Park location. Built by Vimaro Homes, this extraordinary new construction estate is a statement piece that redefines what

    Julie Christensen ONE LUXURY INTERNATIONAL LLC

    40 Palmer Ave, 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 $2,546,833

    Last Listing Agent Julie Bettosini STOCKWORTH REALTY GROUP

    1341 Place Picardy, Winter Park, FL 32789
    • /2

      Est $95,313 Not Listed For Sale

      3035 George Mason Ave Unit 18, Winter Park, FL 32792

      • 1 Bed
      • 1 Bath
      • 549 Sq Ft
      • Built 1974
      3035 George Mason Ave Unit 18, Winter Park, FL 32792

      Last Sold Summary

      • 18% Below List Price
      • $211/SF
      • 196 Days On Market
      • Last Sold Price $116,000
      • Sep 10, 2024

      Last Listing Agent Margarita Morales OLYMPUS EXECUTIVE REALTY INC

  • /53

    $2,184,000 Pending

    • 5 Beds
    • 4 Baths
    • 4,026 Sq Ft

    2503 Versailles Ave, Winter Park, FL 32789

    Under contract-accepting backup offers. Back on the market—an exceptional opportunity in Winter Park. Now offered below appraised value, this residence has been thoughtfully refreshed with new carpet, interior paint, and thoughtful enhancements.Presented for the first time, this beautifully appointed 2014 David Weekley home is tucked away on a large corner lot within a rare cul-de-sac in the

    Sarah Tomlinson COMPASS FLORIDA LLC

    2503 Versailles Ave, Winter Park, FL 32789
  • /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 $448,669

    Last Listing Agent Benjamin Benami CHARLES RUTENBERG REALTY ORLANDO

    2209 Fairglenn Way, Winter Park, FL 32792
    • /18

      Est $447,697 Not Listed For Sale

      1916 Erudite Way, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,782 Sq Ft
      • Built 2024
      1916 Erudite Way, Winter Park, FL 32792

      Last Sold Summary

      • 4% Below List Price
      • $262/SF
      • 146 Days On Market
      • Last Sold Price $466,790
      • Mar 11, 2024

      Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC

  • /41

    $460,000

    • 3 Beds
    • 2 Baths
    • 1,263 Sq Ft

    5331 Oak Ct, Winter Park, FL 32792

    Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to

    Nataliya Voroshylo CHARLES RUTENBERG REALTY ORLANDO

    5331 Oak Ct, 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 $713,552

    Last Listing Agent Steven Ritz KELLER WILLIAMS WINTER PARK

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

      Est $537,990 Not Listed For Sale

      1051 Aragon Ave Unit 1051, Winter Park, FL 32789

      • 3 Beds
      • 2.5 Baths
      • 1,669 Sq Ft
      • Built 1987
      1051 Aragon Ave Unit 1051, Winter Park, FL 32789

      Last Sold Summary

      • 6% Below List Price
      • $342/SF
      • 104 Days On Market
      • Last Sold Price $570,000
      • Sep 16, 2024

      Last Listing Agent Maria Van Warner FANNIE HILLMAN & ASSOCIATES

  • /27

    $169,500

    • 2 Beds
    • 1.5 Baths
    • 990 Sq Ft

    3282 Oak Lake Place, Winter Park, FL 32792

    Welcome to Hidden Oaks! This beautifully updated 2-story condo offers the perfect blend of style and affordability. Featuring a fresh kitchen, renovated bathroom, and new flooring throughout, this move-in-ready home includes an in-unit washer/dryer for ultimate convenience. As a desirable end unit, you’ll enjoy extra privacy and a peaceful view of the adjacent conservation area. Relax on your

    Chad Busby BUSBY REALTY LLC

    3282 Oak Lake Place, 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 $234,932

    Last Listing Agent Jessica Geer A+ REALTY PROFESSIONALS, INC

    200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792
    • /2

      Est $369,461 Not Listed For Sale

      7632 Aloma Pines Ct, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,872 Sq Ft
      • Built 2018
      7632 Aloma Pines Ct, Winter Park, FL 32792

      Last Sold Summary

      • $198/SF
      • 129 Days On Market
      • Last Sold Price $370,000
      • Jan 30, 2025

      Last Listing Agent Dayanne Rivera PREFERRED REAL ESTATE BROKERS

  • /43

    $169,000 Pending

    • 1 Bed
    • 1 Bath
    • 793 Sq Ft

    200 Saint Andrews Blvd Unit 315, Winter Park, FL 32792

    **One or more photos were virtually stages**Experience elevated living in this beautifully appointed 1-bedroom, 1-bath residence located on the second floor in the heart of Winter Park, Florida. The home showcases elegant wood-look tile flooring throughout, creating a seamless, upscale aesthetic with both style and durability.The primary bedroom is enhanced with classic plantation shutters,

    Eric Zimmerman RE/MAX Advantage

    200 Saint Andrews Blvd Unit 315, 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 $538,464

    Last Listing Agent Renee Killiri RED BIRD REALTY OF FLORIDA INC

    4200 Bear Gully Rd, Winter Park, FL 32792
    • /32

      Est $457,540 Not Listed For Sale

      2445 Firstlight Way, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 2,010 Sq Ft
      • Built 2018
      2445 Firstlight Way, Winter Park, FL 32792

      Last Sold Summary

      • 1% Below List Price
      • $229/SF
      • 41 Days On Market
      • Last Sold Price $460,000
      • Oct 17, 2023

      Last Listing Agent Karen Wheeler RE/MAX CENTRAL REALTY

  • /27

    $470,000

    • 4 Beds
    • 2 Baths
    • 1,787 Sq Ft

    1032 Manchester Cir, Winter Park, FL 32792

    Welcome to this beautifully maintained 4-bedroom, 2-bath pool home nestled in one of the nice neighborhoods in Winter Park, located within Seminole County. Offering the perfect blend of comfort, space, and Florida living, this home is designed for both everyday enjoyment and effortless entertaining.Step inside to discover a spacious, light-filled floor plan featuring generous living areas,

    Nancy Morales BHHS FLORIDA REALTY

    1032 Manchester Cir, 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 $518,614

    Last Listing Agent Edwin Ayala, Jr EXP REALTY LLC

    4991 Tangerine Ave, Winter Park, FL 32792
    • /62

      Est $1,972,239 Not Listed For Sale

      2156 Talman Ct, Winter Park, FL 32792

      • 5 Beds
      • 8 Baths
      • 7,762 Sq Ft
      • Built 2008
      2156 Talman Ct, Winter Park, FL 32792

      Last Sold Summary

      • 4% Below List Price
      • $264/SF
      • 32 Days On Market
      • Last Sold Price $2,050,000
      • Oct 26, 2023

      Last Listing Agent Abby Nguyen AGENCYONE

  • /9

    $349,000

    • 2 Beds
    • 1 Bath
    • 749 Sq Ft

    811 Overspin Dr, Winter Park, FL 32789

    Charming Winter Park Opportunity in Desirable Dubsdread Heights! NEW ROOF NEW A/c new kitchen ,bath, floor Welcome to 811 Overspin Drive, a cozy and character-filled 2-bedroom, 1-bath single-family home nestled in the heart of Winter Park. This property offers approximately 700+ square feet of living space on a generously sized lot, providing endless potential for homeowners, investors, or those

    Rickey Singh RICK SINGH REAL ESTATE

    811 Overspin Dr, 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 $417,125

    Last Listing Agent Joey Bruno CHARLES RUTENBERG REALTY ORLANDO

    875 W Lyman Ave, Winter Park, FL 32789
    • /20

      Est $467,151 Not Listed For Sale

      2448 Firstlight Way, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 2,076 Sq Ft
      • Built 2020
      2448 Firstlight Way, Winter Park, FL 32792

      Last Sold Summary

      • 5% Above List Price
      • $214/SF
      • 89 Days On Market
      • Last Sold Price $445,000
      • Oct 30, 2023

      Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

Showing Results 641 - 680, Page 17 of 18

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