11,849

Homes in ZIP Code 32789

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    • /18

      Est $335,250

      Not Listed For Sale

      420 Killarney Bay Ct Unit 2, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 1,160 Sq Ft
      • Built 1986
      420 Killarney Bay Ct Unit 2, Winter Park, FL 32789

      Last Sold Summary

      • 0 Days On Market

  • /7

    $535,000

    • 2 Beds
    • 1 Bath
    • 857 Sq Ft

    981 Aragon Ave, Winter Park, FL 32789

    Charming renovated bungalow on a brick street in the heart of Winter Park! Recently updated with new finishes and appliances throughout. Move in ready, no HOA, and just a short stroll from Rollins College and beautiful Park Avenue. A rare must see opportunity!

    Thomas Bonner COLDWELL BANKER REALTY

    981 Aragon Ave, Winter Park, FL 32789
  • /2

    $2,495,000

    Sold Jul 22, 2025

    940 Lincoln Cir, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 3,551 Sq Ft
    • Built 1995

    Last Sold Summary

    • 26% Below List Price
    • $703/SF
    • 47 Days On Market

    Current Estimated Value $2,550,315

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    940 Lincoln Cir, Winter Park, FL 32789
    • /2

      Est $338,187

      Not Listed For Sale

      647 Huntington Ave Unit 8, Winter Park, FL 32789

      • 2 Beds
      • 2.5 Baths
      • 1,204 Sq Ft
      • Built 1981
      647 Huntington Ave Unit 8, Winter Park, FL 32789

      Last Sold Summary

      • 54 Days On Market

  • /41

    $2,250,000

    New Construction Open Sat 11AM - 2PM
    • 5 Beds
    • 4.5 Baths
    • 2,889 Sq Ft

    240 N Phelps Ave, Winter Park, FL 32789

    A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort. The open-concept living areas are filled

    Nickolas McKee KELLER WILLIAMS WINTER PARK

    240 N Phelps Ave, Winter Park, FL 32789
  • /2

    $450,000

    Sold Mar 31, 2026

    764 W Comstock Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 925 Sq Ft
    • Built 1935

    Last Sold Summary

    • 5% Below List Price
    • $486/SF
    • 17 Days On Market

    Current Estimated Value $465,382

    Last Listing Agent Manny del Valle KELLER WILLIAMS WINTER PARK

    764 W Comstock Ave, Winter Park, FL 32789
    • /2

      Est $832,198

      Not Listed For Sale

      1248 S Pennsylvania Ave Unit 7, Winter Park, FL 32789

      • 3 Beds
      • 2.5 Baths
      • 1,957 Sq Ft
      • Built 2007
      1248 S Pennsylvania Ave Unit 7, Winter Park, FL 32789

      Last Sold Summary

      • 16 Days On Market

  • /63

    $1,649,000

    $146K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,304 Sq Ft

    2501 Winter Park Rd, Winter Park, FL 32789

    PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUSTOM-BUILT home in Winter Park is rare. Finding one built this recently—with this level of craftsmanship, infrastructure, and thoughtful design—is even rarer. Built by Barefoot Brothers in 2014 and thoughtfully designed for an active family that values entertaining, work-from-home flexibility, and elevated

    Jill Healey KELLER WILLIAMS WINTER PARK

    2501 Winter Park Rd, Winter Park, FL 32789
  • /2

    $900,000

    Sold Aug 29, 2025

    3011 Temple Trail, Winter Park, FL 32789

    • 5 Beds
    • 2.5 Baths
    • 2,406 Sq Ft
    • Built 1965

    Last Sold Summary

    • 10% Below List Price
    • $374/SF
    • 83 Days On Market

    Current Estimated Value $921,436

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    3011 Temple Trail, Winter Park, FL 32789
    • /90

      Est $841,517

      Not Listed For Sale

      1264 S Pennsylvania Ave Unit 10, Winter Park, FL 32789

      • 3 Beds
      • 2.5 Baths
      • 1,957 Sq Ft
      • Built 2007
      1264 S Pennsylvania Ave Unit 10, Winter Park, FL 32789

      Last Sold Summary

      • 98 Days On Market

  • /46

    $2,499,000

    New Construction Open Sat 12PM - 2PM
    • 5 Beds
    • 4.5 Baths
    • 3,520 Sq Ft

    426 Worthington Dr, Winter Park, FL 32789

    Nestled within the highly sought-after Kenilworth Shores neighborhood, this extraordinary new construction home represents a rare opportunity to own one of Winter Park's finest new builds. Thoughtfully designed with an exceptional floor plan and uncompromising level of craftsmanship, detail, and finishes. This home is located just minutes from everything Winter Park has to offer. Step through the

    Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    426 Worthington Dr, Winter Park, FL 32789
  • /2

    $4,150,000

    Sold Feb 18, 2026

    702 Via Bella, Winter Park, FL 32789

    • 4 Beds
    • 5.5 Baths
    • 3,720 Sq Ft
    • Built 2025

    Last Sold Summary

    • 11% Below List Price
    • $1,116/SF
    • 149 Days On Market

    Current Estimated Value $4,006,725

    Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

    702 Via Bella, Winter Park, FL 32789
    • /37

      Est $303,574

      Not Listed For Sale

      1302 S Pennsylvania Ave Unit 4, Winter Park, FL 32789

      • 2 Beds
      • 1 Bath
      • 830 Sq Ft
      • Built 1983
      1302 S Pennsylvania Ave Unit 4, Winter Park, FL 32789

      Last Sold Summary

      • 4 Days On Market

  • /42

    $515,000

    • 3 Beds
    • 3 Baths
    • 1,786 Sq Ft

    525 Ololu Dr, Winter Park, FL 32789

    Back on market. Previous contract was canceled due to buyer circumstances. Seller is motivated and ready to move forward.Fully renovated and carefully reimagined, this 3 bedroom, 3 bath residence in the heart of Winter Park offers a compelling combination of quality, functionality, and long term value. Designed with intention and attention to detail, the property presents a refreshed, modern

    Gisela Rojas CAISSA REALTY INVESTMENT INC

    525 Ololu Dr, Winter Park, FL 32789
  • /2

    $190,000

    Sold Mar 20, 2026

    1250 S Denning Dr Unit 104, Winter Park, FL 32789

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

    Last Sold Summary

    • 17% Below List Price
    • $209/SF
    • 60 Days On Market

    Current Estimated Value $195,635

    Last Listing Agent John Harbuck SERHANT

    1250 S Denning Dr Unit 104, Winter Park, FL 32789
    • /2

      Est $612,779

      Not Listed For Sale

      1086 Azalea Ln, Winter Park, FL 32789

      • 3 Beds
      • 2 Baths
      • 1,785 Sq Ft
      • Built 1983
      1086 Azalea Ln, Winter Park, FL 32789

      Last Sold Summary

      • 17 Days On Market

  • /37

    $899,000

    Open Sat 12PM - 2PM
    • 3 Beds
    • 3.5 Baths
    • 1,824 Sq Ft

    1411 Miller Ave, Winter Park, FL 32789

    Built in 2023 by SGC Homes, this exceptionally livable modern Mediterranean townhome blends comfort and convenience in a classic architectural package, offering 3 bedrooms, 3-1/2 baths, and no shared internal walls, for perfect privacy. There is so much to love here. Situated on a tree-lined brick street in the walkable, convenient area of Minnesota Row, this beauty has been lightly occupied as a

    Sue Gilman KELLER WILLIAMS WINTER PARK

    1411 Miller Ave, Winter Park, FL 32789
  • /2

    $368,500

    Sold Apr 03, 2026

    958 Dupont Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,572 Sq Ft
    • Built 1956

    Last Sold Summary

    • 3% Below List Price
    • $234/SF
    • 49 Days On Market

    Current Estimated Value $369,630

    Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

    958 Dupont Ave, Winter Park, FL 32789
    • /2

      Est $510,330

      Not Listed For Sale

      213 E Canton Ave Unit 213, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 1,040 Sq Ft
      • Built 1971
      213 E Canton Ave Unit 213, Winter Park, FL 32789

      Last Sold Summary

      • 97 Days On Market

  • /70

    $3,500,000

    New Construction
    • 5 Beds
    • 6.5 Baths
    • 4,168 Sq Ft

    1836 Whitehall Dr, Winter Park, FL 32789

    Experience resort-style living at 1836 Whitehall Drive! Inspired by the warm breeze and seaside elegance of a tranquil island paradise, this new custom home by Urban Perch, A Boutique Home Builder, offers a timeless front elevation, exquisite finishes inside and out, and unobstructed views of the beautiful outdoors from almost every room. Totaling 4,168 square feet, this five-bedroom, five-bath

    Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

    1836 Whitehall Dr, Winter Park, FL 32789
  • /2

    $1,650,000

    Sold May 01, 2026

    1016 Howell Branch Rd, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 3,142 Sq Ft
    • Built 1959

    Last Sold Summary

    • 3% Below List Price
    • $525/SF
    • 7 Days On Market

    Current Estimated Value $1,661,660

    Last Listing Agent Andrew Birr PLAID PROPERTIES, LLC

    1016 Howell Branch Rd, Winter Park, FL 32789
    • /30

      Est $1,690,938

      Not Listed For Sale

      102 S Virginia Ave Unit 110, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 3,778 Sq Ft
      • Built 2008
      102 S Virginia Ave Unit 110, Winter Park, FL 32789

      Last Sold Summary

      • 70 Days On Market

  • /41

    $1,005,000

    $10K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 2,335 Sq Ft

    1725 Carollee Ln, Winter Park, FL 32789

    Nestled in one of Winter Park’s most sought-after neighborhoods, this charming and meticulously maintained home offers three bedrooms, two baths, an open floor plan, hardwood floors, and thoughtful updates throughout. Recent improvements include a new AC, new hot water heater, new driveway and walkway pavers, and refreshed front and backyard landscaping featuring a magnolia tree, camellias,

    Kyle Grafton FANNIE HILLMAN & ASSOCIATES

    1725 Carollee Ln, Winter Park, FL 32789
  • /2

    $810,000

    Sold Nov 26, 2025

    1314 Canterbury Rd, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,738 Sq Ft
    • Built 1950

    Last Sold Summary

    • $466/SF

    Current Estimated Value $808,157

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    1314 Canterbury Rd, Winter Park, FL 32789
    • /2

      Est $447,134

      Not Listed For Sale

      1216 Park Green Place, Winter Park, FL 32789

      • 3 Beds
      • 3 Baths
      • 2,020 Sq Ft
      • Built 1982
      1216 Park Green Place, Winter Park, FL 32789

      Last Sold Summary

      • 207 Days On Market

  • /47

    $675,000

    • 3 Beds
    • 2 Baths
    • 1,370 Sq Ft

    840 W Canton Ave, Winter Park, FL 32789

    Fully renovated 2 bedroom and 2 bathroom home with a bonus room, ideally located in the heart of Winter Park. Every detail has been updated, including new mechanical systems, electrical, plumbing, custom doors and windows, gutters, stucco finishes, fixtures, fresh landscaping, and new sod. Inside, you'll find an open-concept floor plan with professionally installed luxury vinyl plank flooring

    Ken Pozek REAL BROKER, LLC

    840 W Canton Ave, Winter Park, FL 32789
  • /2

    $2,495,000

    Sold Jul 21, 2025

    1690 Palm Ave, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 3,967 Sq Ft
    • Built 2020

    Last Sold Summary

    • 12% Below List Price
    • $629/SF
    • 56 Days On Market

    Current Estimated Value $2,542,761

    Last Listing Agent Daniel Robinson HOUWZER INC

    1690 Palm Ave, Winter Park, FL 32789
    • /68

      Est $1,006,778

      Not Listed For Sale

      645 N Interlachen Ave, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 1,766 Sq Ft
      • Built 1981
      645 N Interlachen Ave, Winter Park, FL 32789

      Last Sold Summary

      • 107 Days On Market

  • /26

    $1,895,000

    • 3 Beds
    • 3.5 Baths
    • 2,767 Sq Ft

    622 Penn Place, Winter Park, FL 32789

    Located just steps to the Golf Course and Park Avenue, in downtown Winter Park, 622 Penn Place is in the highly sought after Penn Place neighborhood. One of the few homes fronting the park with beautiful views from upper and lower porches, balconies and windows. This home provides the perfect balance of quiet privacy and convenient access to everything. The heart of the home features white

    Doug Addeo COMMUNITY REALTY ASSOCIATES

    622 Penn Place, Winter Park, FL 32789
  • /2

    $4,500,000

    Sold May 29, 2026

    1521 Harris Cir, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 3,922 Sq Ft
    • Built 2026

    Last Sold Summary

    • $1,147/SF
    • 0 Days On Market

    Current Estimated Value $1,839,735

    Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

    1521 Harris Cir, Winter Park, FL 32789
    • /47

      Est $2,283,941

      Not Listed For Sale

      200 S Interlachen Ave Unit 450, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 3,110 Sq Ft
      • Built 2001
      200 S Interlachen Ave Unit 450, Winter Park, FL 32789

      Last Sold Summary

      • 85 Days On Market

  • /29

    $925,000

    $24K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,086 Sq Ft

    560 Ololu Dr, Winter Park, FL 32789

    Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this

    Tiffany Yates COMPASS FLORIDA LLC

    560 Ololu Dr, Winter Park, FL 32789
  • /2

    $1,075,000

    Sold Jul 31, 2025

    1690 Oneco Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,703 Sq Ft
    • Built 1967

    Last Sold Summary

    • 10% Below List Price
    • $398/SF
    • 140 Days On Market

    Current Estimated Value $1,145,705

    Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

    1690 Oneco Ave, Winter Park, FL 32789
    • /38

      Est $847,250

      Not Listed For Sale

      1272 S Pennsylvania Ave Unit 11, Winter Park, FL 32789

      • 3 Beds
      • 2.5 Baths
      • 1,957 Sq Ft
      • Built 2007
      1272 S Pennsylvania Ave Unit 11, Winter Park, FL 32789

      Last Sold Summary

      • 60 Days On Market

  • /24

    $3,300,000

    New Construction
    • 5 Beds
    • 5.5 Baths
    • 3,421 Sq Ft

    1627 Mizell Ave, Winter Park, FL 32789

    One or more photo(s) has been virtually staged. Under Construction. Under construction. Experience approachable luxury combined with wellness-focused living in this newly crafted masterpiece by Urban Perch, a boutique home builder. In downtown Winter Park, this stunning new construction home offers 3,421 square feet of elegant, efficient living area. The primary residence features four bedrooms

    Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

    1627 Mizell Ave, Winter Park, FL 32789
  • /2

    $1,129,000

    Sold Dec 10, 2025

    100 S Virginia Ave Unit 314, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 2,615 Sq Ft
    • Built 2009

    Last Sold Summary

    • $432/SF
    • 4 Days On Market

    Current Estimated Value $1,135,646

    Last Listing Agent Julieta Knapp ACCUMARK PROPERTIES

    100 S Virginia Ave Unit 314, Winter Park, FL 32789
    • /66

      Est $1,490,124

      Not Listed For Sale

      101 S New York Ave Unit 301, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 3,176 Sq Ft
      • Built 2008
      101 S New York Ave Unit 301, Winter Park, FL 32789

      Last Sold Summary

      • 2 Days On Market

  • /49

    $175,000

    $55K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 956 Sq Ft

    2500 Lee Rd Unit 208, Winter Park, FL 32789

    This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water, cable and internet are included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents

    Debbie Fussell KELLER WILLIAMS REALTY AT THE PARKS

    2500 Lee Rd Unit 208, Winter Park, FL 32789
  • /2

    $702,050

    Sold Jan 23, 2026

    300 Carolina Ave Unit 201, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,305 Sq Ft
    • Built 1981

    Last Sold Summary

    • 5% Below List Price
    • $538/SF
    • 19 Days On Market

    Current Estimated Value $699,216

    Last Listing Agent Teri Webster LPT REALTY, LLC

    300 Carolina Ave Unit 201, Winter Park, FL 32789
    • /2

      Est $1,200,069

      Not Listed For Sale

      335 W Welbourne Ave Unit 103, Winter Park, FL 32789

      • 3 Beds
      • 3 Baths
      • 2,734 Sq Ft
      • Built 2008
      335 W Welbourne Ave Unit 103, Winter Park, FL 32789

      Last Sold Summary

      • 184 Days On Market

Showing Results 561 - 600, Page 15 of 18

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