11,850

Homes in ZIP Code 32789

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    • /47

      Est $1,370,492

      Not Listed For Sale

      518 W Swoope Ave, Winter Park, FL 32789

      • 3 Beds
      • 2.5 Baths
      • 2,734 Sq Ft
      • Built 2021
      518 W Swoope Ave, Winter Park, FL 32789

      Last Sold Summary

      • 119 Days On Market

  • /22

    $1,795,000

    New Construction
    • 4 Beds
    • 4 Baths
    • 2,819 Sq Ft

    2501 Lafayette Ave, Winter Park, FL 32789

    Virtually Staged. A rare new construction offering in the heart of Winter Park — 2501 Lafayette Ave is a 2,810 sq ft architectural residence crafted by curated design firm - Catalyst Design, with 25-year experience and Parade of Homes judge across Naples, Daytona & Southwest Florida. 4 bed | 4 bath | office | 2-car garage | saltwater pool. Every detail built to a single standard: the highest one.

    Michael Elias CHARLES RUTENBERG REALTY ORLANDO

    2501 Lafayette Ave, Winter Park, FL 32789
  • /2

    $630,000

    Sold Aug 11, 2025

    1792 Killarney Dr, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,264 Sq Ft
    • Built 1958

    Last Sold Summary

    • 3% Below List Price
    • $278/SF
    • 1 Day On Market

    Current Estimated Value $664,443

    Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

    1792 Killarney Dr, Winter Park, FL 32789
    • /32

      Est $2,326,270

      Not Listed For Sale

      170 S Phelps Ave, Winter Park, FL 32789

      • 4 Beds
      • 4.5 Baths
      • 4,288 Sq Ft
      • Built 2023
      170 S Phelps Ave, Winter Park, FL 32789

      Last Sold Summary

      • 236 Days On Market

  • /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

    $2,185,000

    Sold May 21, 2026

    2722 Eastern Pkwy, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,334 Sq Ft
    • Built 2026

    Last Sold Summary

    • 5% Below List Price
    • $655/SF
    • 105 Days On Market

    Current Estimated Value $1,678,189

    Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    2722 Eastern Pkwy, Winter Park, FL 32789
    • /41

      Est $841,387

      Not Listed For Sale

      440 Shoreview Ave, Winter Park, FL 32789

      • 4 Beds
      • 3 Baths
      • 2,205 Sq Ft
      • Built 2014
      440 Shoreview Ave, Winter Park, FL 32789

      Last Sold Summary

      • 4 Days On Market

  • /10

    $5,500,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 4,775 Sq Ft

    313 Sylvan Dr, Winter Park, FL 32789

    Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37-acre (16,603± square foot) homesite, presents a rare opportunity to own a thoughtfully curated custom home by renowned builder Floridian Custom Homes, brought to life in collaboration with Winter Park Design, Brianna Michelle Interior Design and Signature Landscape. Offering 4,775 heated

    Mick Night PREMIER SOTHEBY'S INTL. REALTY

    313 Sylvan Dr, Winter Park, FL 32789
  • /2

    $755,000

    Sold Jul 18, 2025

    1000 Howell Branch Rd, Winter Park, FL 32789

    • Land
    • 23,958 Sq Ft
    • $1,372,727 per Acre

    Last Sold Summary

    • 30% Below List Price
    • 241 Days On Market

    Current Estimated Value $835,809

    Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

    1000 Howell Branch Rd, Winter Park, FL 32789
    • /2

      Est $1,426,939

      Not Listed For Sale

      1009 S Pennsylvania Ave, Winter Park, FL 32789

      • 4 Beds
      • 3 Baths
      • 3,023 Sq Ft
      • Built 2016
      1009 S Pennsylvania Ave, Winter Park, FL 32789

      Last Sold Summary

      • 5 Days On Market

  • /60

    $2,150,000

    $195K PRICE DROP Pending
    • 4 Beds
    • 3.5 Baths
    • 3,986 Sq Ft

    2299 Via Tuscany, Winter Park, FL 32789

    Under contract-accepting backup offers. BACK ON MARKET. Picture yourself unwinding in your private 0.41-acre yard, taking a dip in the pool, flipping through a good book, or hosting friends on a sunny afternoon. From there, stroll over to the Winter Park Racquet Club for tennis, pickleball, or lunch (kids are covered—there’s a sidewalk the whole way), or head to the deeded lake access launch for

    Vincent Scarlatos CORCORAN PREMIER REALTY

    2299 Via Tuscany, Winter Park, FL 32789
  • /2

    $975,000

    Sold Feb 10, 2026

    1150 Kenwood Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,557 Sq Ft
    • Built 1988

    Last Sold Summary

    • 24% Below List Price
    • $381/SF
    • 97 Days On Market

    Current Estimated Value $1,023,083

    Last Listing Agent JJ Mackle PREMIER SOTHEBY'S INTL. REALTY

    1150 Kenwood Ave, Winter Park, FL 32789
    • /2

      Est $1,895,202

      Not Listed For Sale

      643 Pansy Ave, Winter Park, FL 32789

      • 4 Beds
      • 3.5 Baths
      • 3,228 Sq Ft
      • Built 2015
      643 Pansy Ave, Winter Park, FL 32789

      Last Sold Summary

      • 10 Days On Market

  • /36

    $849,000

    Open Sat 2PM - 4PM
    • 3 Beds
    • 2.5 Baths
    • 1,904 Sq Ft

    437 N Capen Ave, Winter Park, FL 32789

    Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this exceptional residence delivers the walkable lifestyle that defines one of Central Florida’s most coveted communities. Leave the car behind and enjoy easy access to award-winning restaurants, boutique shopping, coffee shops, art galleries, Rollins College, the Winter Park Farmers’

    Brandon Geers COMPASS FLORIDA LLC

    437 N Capen Ave, Winter Park, FL 32789
  • /2

    $475,000

    Sold May 14, 2026

    665 W Lyman Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,119 Sq Ft
    • Built 1994

    Last Sold Summary

    • 6% Above List Price
    • $424/SF
    • 6 Days On Market

    Current Estimated Value $447,753

    Last Listing Agent Jonathan Nakhnoukh CENTRAL FLORIDA PRIME REAL ESTATE LLC

    665 W Lyman Ave, Winter Park, FL 32789
    • /31

      Est $922,382

      Not Listed For Sale

      842 English Ct, Winter Park, FL 32789

      • 3 Beds
      • 2.5 Baths
      • 1,903 Sq Ft
      • Built 2023
      842 English Ct, Winter Park, FL 32789

      Last Sold Summary

  • /29

    $515,000

    $65K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,818 Sq Ft

    1807 Hammerlin Ave Unit G, Winter Park, FL 32789

    Virtually Staged. **Price Improvement** Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events. Situated in the heart of Winter Park, this residence offers the perfect blend of lifestyle,

    Courtney Dietch ALL REAL ESTATE & INVESTMENTS

    1807 Hammerlin Ave Unit G, Winter Park, FL 32789
  • /2

    $475,000

    Sold Feb 02, 2026

    1740 Anzle Ave, Winter Park, FL 32789

    • 4 Beds
    • 2 Baths
    • 1,808 Sq Ft
    • Built 1956

    Last Sold Summary

    • 40% Below List Price
    • $263/SF
    • 109 Days On Market

    Current Estimated Value $607,200

    Last Listing Agent Freddy DeCoster GOYAL & DECOSTER REALTY

    1740 Anzle Ave, Winter Park, FL 32789
    • /2

      Est $1,576,592

      Not Listed For Sale

      1571 Sunset Dr, Winter Park, FL 32789

      • 4 Beds
      • 4 Baths
      • 2,700 Sq Ft
      • Built 2015
      1571 Sunset Dr, Winter Park, FL 32789

      Last Sold Summary

      • 79 Days On Market

  • /26

    $499,000

    $51K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,433 Sq Ft

    2974 Chantilly Ave, Winter Park, FL 32789

    Virtually Staged. WINTER PARK 32789 in the highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park High school district. This is the kind of home buyers hope to find but rarely do — a beautifully updated mid-century modern with the character of the 1960s and the peace of mind that comes from extensive major improvements already being completed. From the moment you arrive, the

    Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    2974 Chantilly Ave, Winter Park, FL 32789
  • /2

    $2,750,000

    Sold Jun 18, 2026

    151 Oakwood Way, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 4,129 Sq Ft
    • Built 2023

    Last Sold Summary

    • 14% Below List Price
    • $666/SF
    • 113 Days On Market

    Current Estimated Value $2,884,311

    Last Listing Agent Matthew Burks CORCORAN PREMIER REALTY

    151 Oakwood Way, Winter Park, FL 32789
    • /2

      Est $2,129,652

      Not Listed For Sale

      1770 Oakhurst Ave, Winter Park, FL 32789

      • 5 Beds
      • 4.5 Baths
      • 3,640 Sq Ft
      • Built 2019
      1770 Oakhurst Ave, Winter Park, FL 32789

      Last Sold Summary

      • 20 Days On Market

  • /50

    $1,425,000

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,170 Sq Ft

    1751 Goodrich Ave, Winter Park, FL 32789

    Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes

    Stephanie Baldner EXP REALTY LLC

    1751 Goodrich Ave, Winter Park, FL 32789
  • /2

    $325,000

    Sold Oct 03, 2025

    260 Killarney Bay Ct Unit 6, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,140 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Below List Price
    • $285/SF
    • 0 Days On Market

    Current Estimated Value $325,603

    Last Listing Agent Tyler Gibson LPT REALTY, LLC

    260 Killarney Bay Ct Unit 6, Winter Park, FL 32789
    • /2

      Est $1,154,413

      Not Listed For Sale

      1571 Oneco Ave, Winter Park, FL 32789

      • 4 Beds
      • 3 Baths
      • 2,510 Sq Ft
      • Built 2009
      1571 Oneco Ave, Winter Park, FL 32789

      Last Sold Summary

      • 41 Days On Market

  • /2

    $3,100,000

    New Construction Pending
    • 5 Beds
    • 4.5 Baths
    • 3,460 Sq Ft

    1351 Magnolia Ave, Winter Park, FL 32789

    Under Construction. Just completed and ready to impress, this stunning custom-built residence delivers elevated design and effortless luxury in one of Winter Park’s most sought-after locations. Featuring 5 bedrooms and 4.5 bathrooms, this home blends timeless architecture with a fresh, curated aesthetic.From the moment you step inside, you’re greeted by warm wood flooring, custom millwork,

    Nickolas McKee KELLER WILLIAMS WINTER PARK

    1351 Magnolia Ave, Winter Park, FL 32789
  • /2

    $1,725,000

    Sold Mar 05, 2026

    617 Worthington Dr, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,533 Sq Ft
    • Built 2018

    Last Sold Summary

    • 13% Below List Price
    • $488/SF
    • 215 Days On Market

    Current Estimated Value $1,755,958

    Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

    617 Worthington Dr, Winter Park, FL 32789
    • /29

      Est $592,757

      Not Listed For Sale

      1400 Indiana Ave, Winter Park, FL 32789

      • 3 Beds
      • 2.5 Baths
      • 2,054 Sq Ft
      • Built 2008
      1400 Indiana Ave, Winter Park, FL 32789

      Last Sold Summary

      • 1 Day On Market

  • /25

    $1,249,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,936 Sq Ft

    Winter Park, FL 32789

    Pre-Construction. To be built. NEW CONSTRUCTION! Introducing an exquisite new construction home in Winter Park Grove, Winter Park's newest community! This residence is carefully curated by SGC Development, a highly respected local builder known for their dedication to quality and craftsmanship. This residence combines luxury living with the utmost convenience, located within walking distance to

    Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

    Winter Park, FL 32789
  • /2

    $2,835,000

    Sold Nov 24, 2025

    255 Stirling Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 3,635 Sq Ft
    • Built 1982

    Last Sold Summary

    • 14% Below List Price
    • $780/SF
    • 25 Days On Market

    Current Estimated Value $2,868,037

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

    255 Stirling Ave, Winter Park, FL 32789
    • /2

      Est $560,057

      Not Listed For Sale

      1392 Indiana Ave, Winter Park, FL 32789

      • 3 Beds
      • 2.5 Baths
      • 1,936 Sq Ft
      • Built 2008
      1392 Indiana Ave, Winter Park, FL 32789

      Last Sold Summary

      • 123 Days On Market

  • /47

    $5,995,000

    $455K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 5,476 Sq Ft

    1200 Via Salerno, Winter Park, FL 32789

    Along one of the cobblestone brick streets in the prestigious Via’s of Winter Park, this completely renovated residence pairs timeless European influence with clean architectural lines and bespoke finishes throughout. A circular driveway and manicured grounds designed by Signature Landscapes create a graceful approach. Inside, a dramatic curved staircase crowned by a breathtaking 1960s vintage

    Mick Night PREMIER SOTHEBY'S INTL. REALTY

    1200 Via Salerno, 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 $615,808

    Last Listing Agent Lianna D'Angelo SOTERA LIVING

    1500 Berkshire Ave, Winter Park, FL 32789
    • /59

      Est $2,236,052

      Not Listed For Sale

      1411 Elizabeth Dr, Winter Park, FL 32789

      • 5 Beds
      • 4.5 Baths
      • 3,870 Sq Ft
      • Built 2008
      1411 Elizabeth Dr, Winter Park, FL 32789

      Last Sold Summary

      • 26 Days On Market

  • /29

    $2,695,000

    • 3 Beds
    • 3.5 Baths
    • 3,048 Sq Ft

    413 W Morse Blvd, Winter Park, FL 32789

    LUXURIOUS LIVING WITH FANTASTIC LOCATION This Winter Park three story townhouse is within walking distance to all the fun amenities of the city- the many restaurants, boutique shops, banks, post office, farmers market, Central Park and Rollins College. Designed by architect Phil Kean and built in 2017 the owners have embellished this townhome with custom millwork and finishes, wood floors, sound

    A.V. Blalock COLDWELL BANKER REALTY

    413 W Morse Blvd, Winter Park, FL 32789
  • /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 $1,470,576

    Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

    1011 Mckean Cir, Winter Park, FL 32789
    • /2

      Est $446,769

      Not Listed For Sale

      2112 Staunton Ave, Winter Park, FL 32789

      • 3 Beds
      • 1 Bath
      • 1,438 Sq Ft
      • Built 1954
      2112 Staunton Ave, Winter Park, FL 32789

      Last Sold Summary

      • 12 Days On Market

  • /34

    $745,000

    • 2 Beds
    • 3 Baths
    • 1,440 Sq Ft

    408 Holt Ave, Winter Park, FL 32789

    Rare investment opportunity in the heart of Winter Park/Rollins College area. This turnkey, fully renovated triplex is located within one of Winter Park’s highest-demand rental corridors, just steps from Rollins College, Park Avenue, and Lake Virginia. The property features three separate 1-bedroom, 1-bath units, each with its own private outdoor patio area, positioned on a charming brick street

    Brian Opre THE REAL ESTATE PRINCIPLE, INC

    408 Holt Ave, Winter Park, FL 32789
  • /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 $447,104

    Last Listing Agent Carmen Gonzalez, Pa HORIZON WEST REALTY

    1945 Bering Ave, Winter Park, FL 32789
    • /2

      Est $1,865,233

      Not Listed For Sale

      331 E Reading Way, Winter Park, FL 32789

      • 4 Beds
      • 4.5 Baths
      • 3,361 Sq Ft
      • Built 2007
      331 E Reading Way, Winter Park, FL 32789

      Last Sold Summary

      • 110 Days On Market

Showing Results 241 - 280, Page 7 of 18

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