11,849

Homes in ZIP Code 32789

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  • /42

    $1,695,000

    $100K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,807 Sq Ft

    1903 N Park Ave, Winter Park, FL 32789

    Completed in 2020, this beautifully designed contemporary residence on North Park Avenue offers refined finishes and seamless indoor-outdoor living just minutes from Park Avenue’s famed shopping and restaurant district as well as the vibrant retail and dining of Winter Park Village and Mills50. Positioned on a prominent corner lot with dual access from N Park Ave and N Denning Drive, the home

    Chris Creegan CREEGAN GROUP

    1903 N Park Ave, Winter Park, FL 32789
  • /2

    $4,720,000

    Sold May 15, 2026

    1302 Raintree Place, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 4,738 Sq Ft
    • Built 2025

    Last Sold Summary

    • 11% Below List Price
    • $996/SF
    • 182 Days On Market

    Current Estimated Value $5,026,636

    Last Listing Agent Rikhil Amin FANNIE HILLMAN & ASSOCIATES

    1302 Raintree Place, Winter Park, FL 32789
    • /22

      Est $247,287

      Not Listed For Sale

      1500 Gay Rd Unit 21B, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 1,026 Sq Ft
      • Built 1972
      1500 Gay Rd Unit 21B, Winter Park, FL 32789

      Last Sold Summary

      • 40 Days On Market

  • /28

    $338,000

    • 2 Beds
    • 1 Bath
    • 797 Sq Ft

    2006 Cornell Ave, Winter Park, FL 32789

    Welcome home to this charming and fully remodeled 2-bedroom, 1-bathroom gem nestled in the heart of Winter Park AND College Park. Located just minutes away from Downtown Orlando, Disney, Universal and Advent Health, this sought-after location offers convenience and comfort. This home boasts not only a prime location but also a cozy ambiance that will make you feel right at home. With its hardwood

    Stacia Stephenson FLORIDA HOME TEAM REALTY LLC

    2006 Cornell Ave, Winter Park, FL 32789
  • /2

    $341,000

    Sold Aug 08, 2025

    2827 Euston Rd, Winter Park, FL 32789

    • 4 Beds
    • 2 Baths
    • 1,568 Sq Ft
    • Built 1956

    Last Sold Summary

    • 20% Below List Price
    • $217/SF
    • 205 Days On Market

    Current Estimated Value $351,768

    Last Listing Agent Evelyn Tejada REGENCY REAL ESTATE LLC

    2827 Euston Rd, Winter Park, FL 32789
    • /28

      Est $596,722

      Not Listed For Sale

      102 S Interlachen Ave Unit 510, Winter Park, FL 32789

      • 2 Beds
      • 1 Bath
      • 901 Sq Ft
      • Built 1971
      102 S Interlachen Ave Unit 510, Winter Park, FL 32789

      Last Sold Summary

      • 2 Days On Market

  • /37

    $1,095,000

    • 3 Beds
    • 3.5 Baths
    • 2,213 Sq Ft

    1120 Wisconsin Ave, Winter Park, FL 32789

    Curated with intention and finished without compromise, 1120 Wisconsin Avenue is a rare opportunity to own a bespoke Winter Park residence where elevated design meets effortless everyday living. Every detail of this 2,213-square-foot, three-bedroom, three-and-a-half-bath home has been thoughtfully considered — from the custom Pella® multi-point entry door that welcomes you into a light-filled,

    Kelly Price KELLY PRICE & COMPANY LLC

    1120 Wisconsin Ave, Winter Park, FL 32789
  • /2

    $2,288,215

    Sold Dec 19, 2025

    1602 Alabama Dr Unit 404, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 2,709 Sq Ft
    • Built 1981

    Last Sold Summary

    • 8% Below List Price
    • $845/SF
    • 179 Days On Market

    Current Estimated Value $2,198,430

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    1602 Alabama Dr Unit 404, Winter Park, FL 32789
    • /2

      Est $1,455,560

      Not Listed For Sale

      662 Osceola Ave Unit 203, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 2,290 Sq Ft
      • Built 2003
      662 Osceola Ave Unit 203, Winter Park, FL 32789

      Last Sold Summary

      • 164 Days On Market

  • /2

    $599,999

    Pending
    • Land
    • 16,552 Sq Ft
    • $1,578,945 per Acre

    1821 Killarney Dr, Winter Park, FL 32789

    Under contract-accepting backup offers. Rare opportunity to own a cleared waterfront lot on the shores of Lake Killarney in the heart of Winter Park. Spanning approximately .38 acres, this exceptional property offers stunning lake views and the potential for a future custom residence, subject to buyer verification of building requirements and intended use. Enjoy direct access to Lake Killarney

    Karly Campbell NOVA REAL ESTATE SERVICES INC

    1821 Killarney Dr, Winter Park, FL 32789
  • /2

    $699,000

    Sold Jul 31, 2025

    1891 Bryan Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,622 Sq Ft
    • Built 1989

    Last Sold Summary

    • $431/SF
    • 14 Days On Market

    Current Estimated Value $715,350

    Last Listing Agent Jennifer King CORCORAN PREMIER REALTY

    1891 Bryan Ave, Winter Park, FL 32789
    • /2

      Est $210,108

      Not Listed For Sale

      700 Melrose Ave Unit F2, Winter Park, FL 32789

      • 1 Bed
      • 1 Bath
      • 730 Sq Ft
      • Built 1964
      700 Melrose Ave Unit F2, Winter Park, FL 32789

      Last Sold Summary

      • 193 Days On Market

  • /34

    $725,000

    $300K PRICE INCREASE Pending
    • 4 Beds
    • 2 Baths
    • 1,008 Sq Ft

    770 W Webster Ave, Winter Park, FL 32789

    Under contract-accepting backup offers. Stop the car! Develop your dream project on this hard to find R-3 lot! Adjacent 75x100 R-3 vacant lot (TAX ID 06-22-30-1168-02-023) on the south side to be purchased simultaneously, for a total of 75x200 or 15,000sq/ft. Next to the proposed Winter Park Commons project, walk to Winter Park Village, Hannibal Square, WP9 and Park Ave for top shopping, dining

    Lisa Gould KELLER WILLIAMS WINTER PARK

    770 W Webster Ave, Winter Park, FL 32789
  • /2

    $260,000

    Sold Jan 30, 2026

    1250 S Denning Dr Unit 213, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 908 Sq Ft
    • Built 1967

    Last Sold Summary

    • 5% Below List Price
    • $286/SF
    • 114 Days On Market

    Current Estimated Value $253,776

    Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY

    1250 S Denning Dr Unit 213, Winter Park, FL 32789
    • /27

      Est $348,133

      Not Listed For Sale

      700 Melrose Ave Unit J32, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 1,074 Sq Ft
      • Built 1964
      700 Melrose Ave Unit J32, Winter Park, FL 32789

      Last Sold Summary

      • 0 Days On Market

  • /45

    $689,000

    $70K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,124 Sq Ft

    2157 Lake Dr, Winter Park, FL 32789

    Welcome to this beautifully maintained Winter Park home in coveted 32789, offering over 2,600 square feet, peekaboo Lake Killarney views, and a peaceful setting on a quiet private lakefront street. From the moment you enter, pride of ownership shines through, with custom built-ins throughout creating stylish and functional living spaces.The heart of the home is the updated kitchen and dining

    Jake Johnson SHORES REAL ESTATE

    2157 Lake Dr, Winter Park, FL 32789
  • /2

    $615,000

    Sold Jun 24, 2026

    1780 Goodrich Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,283 Sq Ft
    • Built 1955

    Last Sold Summary

    • 2% Below List Price
    • $479/SF
    • 3 Days On Market

    Current Estimated Value $636,365

    Last Listing Agent Buddy Jerome, III SUMMERPARK HOMES REALTY LLC

    1780 Goodrich Ave, Winter Park, FL 32789
    • /2

      Est $447,382

      Not Listed For Sale

      690 Osceola Ave Unit 610, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 1,328 Sq Ft
      • Built 1969
      690 Osceola Ave Unit 610, Winter Park, FL 32789

      Last Sold Summary

      • 71 Days On Market

  • /24

    $595,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,434 Sq Ft

    1741 Westchester Ave, Winter Park, FL 32789

    In the sought-after Orwin Manor neighborhood, this beautifully updated one-story residence offers a seamless blend of comfort, style and convenience. Featuring three bedrooms and two baths, the home showcases an open-concept floor plan enhanced by engineered wood flooring that extends throughout every room, creating a cohesive and inviting living environment. The kitchen is thoughtfully updated

    Mick Night PREMIER SOTHEBY'S INTL. REALTY

    1741 Westchester Ave, Winter Park, FL 32789
  • /61

    $610,000

    Sold Feb 10, 2026

    1451 Cavendish Rd, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,437 Sq Ft
    • Built 1971

    Last Sold Summary

    • 2% Below List Price
    • $424/SF

    Current Estimated Value $605,243

    Last Listing Agent Spencer Flory LoKation

    1451 Cavendish Rd, Winter Park, FL 32789
    • /2

      Est $463,886

      Not Listed For Sale

      535 N Interlachen Ave Unit 101, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 968 Sq Ft
      • Built 1972
      535 N Interlachen Ave Unit 101, Winter Park, FL 32789

      Last Sold Summary

      • 250 Days On Market

  • /44

    $865,000

    • 3 Beds
    • 3 Baths
    • 2,017 Sq Ft

    338 Blue Heron Dr, Winter Park, FL 32789

    Step into timeless style and modern comfort in this stunning 3-bedroom, 3-bathroom Mid-Century Modern home nestled in the heart of Winter Park. Designed with character and functionality in mind, this unique residence features abundant natural light, clean architectural lines, and a striking pass-through fireplace that creates the perfect ambiance between living spaces. Enjoy true Florida living

    Samuel Kingsford STOCKWORTH REALTY GROUP

    338 Blue Heron Dr, Winter Park, FL 32789
  • /2

    $1,000,000

    Sold Nov 03, 2025

    215 Salvador Square, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,565 Sq Ft
    • Built 1973

    Last Sold Summary

    • 16% Below List Price
    • $390/SF
    • 44 Days On Market

    Current Estimated Value $1,098,564

    Last Listing Agent Carrie Bantel PREMIER SOTHEBY'S INTL. REALTY

    215 Salvador Square, Winter Park, FL 32789
    • /2

      Est $216,346

      Not Listed For Sale

      1250 S Denning Dr Unit 210, Winter Park, FL 32789

      • 2 Beds
      • 1.5 Baths
      • 908 Sq Ft
      • Built 1967
      1250 S Denning Dr Unit 210, Winter Park, FL 32789

      Last Sold Summary

      • 133 Days On Market

  • /43

    $999,000

    $340K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 2,292 Sq Ft

    67 Cypress Ln, Maitland, FL 32751

    Under contract-accepting backup offers. Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This architectural gem, expertly crafted from Western Red Cedar, offers two stories of thoughtfully designed living space with 4 bedrooms and 3 full baths.Step inside

    Kelly Price KELLY PRICE & COMPANY LLC

    67 Cypress Ln, Maitland, FL 32751
  • /2

    $1,776,000

    Sold Jun 26, 2026

    1177 Kenwood Ave, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 4,363 Sq Ft
    • Built 2007

    Last Sold Summary

    • 10% Below List Price
    • $407/SF
    • 69 Days On Market

    Current Estimated Value $1,812,519

    Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

    1177 Kenwood Ave, Winter Park, FL 32789
    • /19

      Est $189,223

      Not Listed For Sale

      2500 Lee Rd Unit 139, Winter Park, FL 32789

      • 2 Beds
      • 1 Bath
      • 851 Sq Ft
      • Built 1969
      2500 Lee Rd Unit 139, Winter Park, FL 32789

      Last Sold Summary

      • 16 Days On Market

  • /11

    $2,690,000

    $100K PRICE DROP
    • Land
    • 20,908 Sq Ft
    • $5,604,167 per Acre

    620 Pinetree Rd, Winter Park, FL 32789

    One of the last remaining opportunities to build on a truly exceptional street in the Winter Park Via’s, this .48-acre homesite offers a fantastic combination of a prime location, a large lot, and surrounded but gorgeous homes. The lot is cleared and ready to build! The current owners have thoughtfully commissioned architectural plans by renowned Winter Park architect Gary Hancock. With the

    MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    620 Pinetree Rd, Winter Park, FL 32789
  • /2

    $675,000

    Sold Nov 28, 2025

    2190 Temple Dr, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,442 Sq Ft
    • Built 1956

    Last Sold Summary

    • 4% Below List Price
    • $468/SF
    • 108 Days On Market

    Current Estimated Value $740,328

    Last Listing Agent Sharon Mikol MAINFRAME REAL ESTATE

    2190 Temple Dr, Winter Park, FL 32789
    • /35

      Est $176,388

      Not Listed For Sale

      2500 Lee Rd Unit 233, Winter Park, FL 32789

      • 1 Bed
      • 1 Bath
      • 645 Sq Ft
      • Built 1969
      2500 Lee Rd Unit 233, Winter Park, FL 32789

      Last Sold Summary

      • 3 Days On Market

  • /55

    $1,295,000

    $200K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    106 S Interlachen Ave Unit 118, Winter Park, FL 32789

    Experience lakefront living in the heart of Winter Park. One of only two residences in The Cloisters with soaring 9-foot ceilings, this first-floor, three-bedroom, two-bath home offers a rare blend of privacy, scale and panoramic Lake Osceola views. Just two blocks from Park Avenue and adjacent to the Alfond Inn, this condominium lives like a private residence with unmatched access to boutique

    Drew Henner PREMIER SOTHEBY'S INTL. REALTY

    106 S Interlachen Ave Unit 118, Winter Park, FL 32789
  • /2

    $380,000

    Sold Sep 26, 2025

    690 Osceola Ave Unit 209, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,148 Sq Ft
    • Built 1969

    Last Sold Summary

    • 11% Below List Price
    • $331/SF
    • 34 Days On Market

    Current Estimated Value $390,614

    Last Listing Agent Mike Wang LOKATION

    690 Osceola Ave Unit 209, Winter Park, FL 32789
    • /2

      Est $225,792

      Not Listed For Sale

      1250 S Denning Dr Unit 205, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 908 Sq Ft
      • Built 1967
      1250 S Denning Dr Unit 205, Winter Park, FL 32789

      Last Sold Summary

      • 53 Days On Market

  • /36

    $1,050,000

    $400K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 2,342 Sq Ft

    632 Country Club Dr, Winter Park, FL 32789

    Under contract-accepting backup offers. Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards

    Kristin Duncan KELLER WILLIAMS ADVANTAGE REALTY

    632 Country Club Dr, Winter Park, FL 32789
  • /2

    $440,000

    Sold Aug 22, 2025

    3019 Northwood Blvd, Winter Park, FL 32789

    • 3 Beds
    • 1.5 Baths
    • 1,662 Sq Ft
    • Built 1953

    Last Sold Summary

    • 35% Below List Price
    • $265/SF
    • 98 Days On Market

    Current Estimated Value $474,795

    Last Listing Agent Robert Arnold SAND DOLLAR REALTY GROUP INC

    3019 Northwood Blvd, Winter Park, FL 32789
    • /2

      Est $210,204

      Not Listed For Sale

      2500 Lee Rd Unit 107, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 956 Sq Ft
      • Built 1969
      2500 Lee Rd Unit 107, Winter Park, FL 32789

      Last Sold Summary

      • 110 Days On Market

  • /27

    $700,000

    • 3 Beds
    • 2 Baths
    • 1,407 Sq Ft

    865 S Pennsylvania Ave, Winter Park, FL 32789

    LOCATION, LOCATION, LOCATION...Desirable Winter Park "College Quarter" Historic District...Come take a tour of this wonderfully updated Bungalow with lots of windows for natural light, original hardwood floors, beautiful crown molding, and high ceilings. Did I mention the location, Walk to Park Ave, Rollins College, Hannibal Square, Mead Gardens, and Lake Virginia. Looking to "House Hack" then

    Jose Vega LPT REALTY, LLC

    865 S Pennsylvania Ave, Winter Park, FL 32789
  • /2

    $312,500

    Sold Oct 21, 2025

    1308 S Pennsylvania Ave Unit 3, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 823 Sq Ft
    • Built 1983

    Last Sold Summary

    • 4% Below List Price
    • $380/SF
    • 9 Days On Market

    Current Estimated Value $304,648

    Last Listing Agent Livia Petraru EXP REALTY LLC

    1308 S Pennsylvania Ave Unit 3, Winter Park, FL 32789
    • /2

      Est $205,854

      Not Listed For Sale

      1250 S Denning Dr Unit 124, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 903 Sq Ft
      • Built 1967
      1250 S Denning Dr Unit 124, Winter Park, FL 32789

      Last Sold Summary

      • 26 Days On Market

  • /43

    $1,569,000

    New Construction $81K PRICE DROP Pending
    • 4 Beds
    • 3.5 Baths
    • 2,249 Sq Ft

    1660 Walnut Ave, Winter Park, FL 32789

    Under contract-accepting backup offers. Introducing a standout new construction in Winter Park’s coveted Tree Streets! As you arrive the home’s modern façade is complemented by a charming front porch, creating a warm yet striking introduction that feels both inviting and intentional. Inside, the home unfolds with a highly functional floor plan designed to enhance everyday living while still

    Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    1660 Walnut Ave, Winter Park, FL 32789

Showing Results 361 - 400, Page 10 of 18

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