11,849

Homes in ZIP Code 32789

Section Image
    • /39

      Est $311,073

      Not Listed For Sale

      700 Melrose Ave Unit K3, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 1,074 Sq Ft
      • Built 1964
      700 Melrose Ave Unit K3, Winter Park, FL 32789

      Last Sold Summary

      • 62 Days On Market

  • /29

    $534,900

    $4K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,660 Sq Ft

    1261 Indiana Ave, Winter Park, FL 32789

    Tucked in the heart of Harper Place, this 3-bedroom, 2.5 bath end unit townhome 1,660 sq ft of light-filled, low maintenance living in a thriving Winter Park location. The main level features a spacious living and dining room combo plus a separate family room and kitchen-perfect for entertaining. The kitchen includes a built-in desk and bookcase, pantry, gas cooktop and range hood, granite

    Megan Cross FANNIE HILLMAN & ASSOCIATES

    1261 Indiana Ave, Winter Park, FL 32789
  • /2

    $1,063,303

    Sold Dec 10, 2025

    1835 Karolina Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,662 Sq Ft
    • Built 2025

    Last Sold Summary

    • 23% Above List Price
    • $399/SF
    • 50 Days On Market

    Current Estimated Value $1,047,000

    Last Listing Agent Laura Hope COMPASS FLORIDA LLC

    1835 Karolina Ave, Winter Park, FL 32789
    • /2

      Est $175,711

      Not Listed For Sale

      700 Melrose Ave Unit G34, Winter Park, FL 32789

      • Studio
      • 1 Bath
      • 624 Sq Ft
      • Built 1964
      700 Melrose Ave Unit G34, Winter Park, FL 32789

      Last Sold Summary

      • 0 Days On Market

  • /50

    $2,490,000

    $360K PRICE DROP Pending
    • 5 Beds
    • 5.5 Baths
    • 4,389 Sq Ft

    1300 Mayfield Ave, Winter Park, FL 32789

    Under contract-accepting backup offers. Tucked behind towering hedges on a coveted brick-lined street, this estate sits on an approximately 1⁄2-acre corner lot, providing modern functionality, Old World charm, and an unmatched lifestyle. The main residence spans over 3,600+ SF with 4 bedrooms, 4 bathrooms, and an attached 2-car garage. Across the brick driveway is a detached, fully-equipped 700+

    MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    1300 Mayfield Ave, Winter Park, FL 32789
  • /2

    $275,000

    Sold Mar 31, 2026

    409 Sandlewood Cove Unit 3, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 1,413 Sq Ft
    • Built 1986

    Last Sold Summary

    • $195/SF

    Current Estimated Value $271,236

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

    409 Sandlewood Cove Unit 3, Winter Park, FL 32789
    • /20

      Est $372,738

      Not Listed For Sale

      700 Melrose Ave Unit C2, Winter Park, FL 32789

      • 3 Beds
      • 2.5 Baths
      • 1,448 Sq Ft
      • Built 1964
      700 Melrose Ave Unit C2, Winter Park, FL 32789

      Last Sold Summary

      • 35 Days On Market

  • /9

    $1,595,000

    • Land
    • 17,859 Sq Ft
    • $3,890,244 per Acre

    1113 Via Del Mar, Winter Park, FL 32789

    Exceptional opportunity in the heart of Winter Park - a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable

    David Barany BAY HILL REALTY LLC

    1113 Via Del Mar, Winter Park, FL 32789
  • /2

    $312,000

    Sold Oct 16, 2025

    1921 Dartmouth Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 987 Sq Ft
    • Built 1956

    Last Sold Summary

    • 16% Below List Price
    • $316/SF
    • 76 Days On Market

    Current Estimated Value $329,320

    Last Listing Agent Pat Hancock THOMAS LYNNE REALTY GROUP LLC

    1921 Dartmouth Ave, Winter Park, FL 32789
    • /44

      Est $2,224,933

      Not Listed For Sale

      200 S Interlachen Ave Unit 400, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 3,074 Sq Ft
      • Built 2001
      200 S Interlachen Ave Unit 400, Winter Park, FL 32789

      Last Sold Summary

      • 40 Days On Market

  • /51

    $549,000

    $50K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,920 Sq Ft

    423 Ololu Dr, Winter Park, FL 32789

    PRICE IMPROVEMENT! Welcome to this beautifully remodeled two story home in one of Winter Park’s most desirable upscale neighborhoods, offering timeless charm, modern upgrades, and no HOA restrictions. Completely renovated in 2019, this property features a newer roof, windows, A/C system, electrical, plumbing, driveway, and a fully fenced yard with a private entry gate, along with fresh exterior &

    Jill Healey KELLER WILLIAMS WINTER PARK

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

    $3,000,000

    Sold Aug 18, 2025

    1730 Winchester Dr, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 4,080 Sq Ft
    • Built 2024

    Last Sold Summary

    • 9% Below List Price
    • $735/SF
    • 313 Days On Market

    Current Estimated Value $3,070,665

    Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK

    1730 Winchester Dr, Winter Park, FL 32789
    • /2

      Est $2,600,303

      Not Listed For Sale

      315 E New England Ave Unit 30, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 3,130 Sq Ft
      • Built 2008
      315 E New England Ave Unit 30, Winter Park, FL 32789

      Last Sold Summary

      • 1 Day On Market

  • /28

    $1,245,000

    $105K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,667 Sq Ft

    2111 Mallard Cir, Winter Park, FL 32789

    One or more photos was virtually staged. Tucked away on a quiet circle in one of Winter Park's most sought-after neighborhoods, this distinctive pool home offers a rare opportunity. Set on an approximately .26-acre lot, the home features striking architectural lines, soaring wood ceilings with exposed beams, polished concrete flooring, and an abundance of natural light throughout. This is the

    Caroline Borling BREC PROPERTIES INC

    2111 Mallard Cir, Winter Park, FL 32789
  • /2

    $2,200,000

    Sold Sep 09, 2025

    1554 Lake Knowles Cir, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 3,155 Sq Ft
    • Built 1954

    Last Sold Summary

    • 12% Below List Price
    • $697/SF
    • 2 Days On Market

    Current Estimated Value $2,150,561

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

    1554 Lake Knowles Cir, Winter Park, FL 32789
    • /2

      Est $1,550,139

      Not Listed For Sale

      315 E New England Ave Unit 9, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 1,637 Sq Ft
      • Built 2007
      315 E New England Ave Unit 9, Winter Park, FL 32789

      Last Sold Summary

      • 5 Days On Market

  • /58

    $6,900,000

    • 6 Beds
    • 7 Baths
    • 6,396 Sq Ft

    1260 Alabama Dr, Winter Park, FL 32789

    Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue.From the

    Kelly Price KELLY PRICE & COMPANY LLC

    1260 Alabama Dr, Winter Park, FL 32789
  • /2

    $1,650,000

    Sold Jun 30, 2025

    2339 Lafayette Ave, Winter Park, FL 32789

    • 4 Beds
    • 6 Baths
    • 3,379 Sq Ft
    • Built 2005

    Last Sold Summary

    • 6% Below List Price
    • $488/SF
    • 15 Days On Market

    Current Estimated Value $1,694,236

    Last Listing Agent Skip Kirst COLLADO REAL ESTATE

    2339 Lafayette Ave, Winter Park, FL 32789
    • /100

      Est $3,006,364

      Not Listed For Sale

      300 S Interlachen Ave Unit 303, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 3,355 Sq Ft
      • Built 2005
      300 S Interlachen Ave Unit 303, Winter Park, FL 32789

      Last Sold Summary

      • 11 Days On Market

  • /39

    $1,849,900

    Open Sun 2PM - 4PM
    • 3 Beds
    • 3.5 Baths
    • 3,112 Sq Ft

    101 S New York Ave Unit 311, Winter Park, FL 32789

    Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank

    Tiffany Grindstaff KELLY PRICE & COMPANY LLC

    101 S New York Ave Unit 311, Winter Park, FL 32789
  • /2

    $3,100,001

    Sold Apr 13, 2026

    611 Williams Dr, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 4,686 Sq Ft
    • Built 2007

    Last Sold Summary

    • 4% Above List Price
    • $662/SF
    • 6 Days On Market

    Current Estimated Value $2,995,439

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    611 Williams Dr, Winter Park, FL 32789
    • /24

      Est $215,175

      Not Listed For Sale

      1250 S Denning Dr Unit 126, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 893 Sq Ft
      • Built 1967
      1250 S Denning Dr Unit 126, Winter Park, FL 32789

      Last Sold Summary

      • 66 Days On Market

  • /44

    $3,500,000

    • 3 Beds
    • 5 Baths
    • 3,180 Sq Ft

    649 N Park Ave, Winter Park, FL 32789

    Park Hill is one of Winter Park's most coveted addresses, a distinguished collection of luxury brownstones situated at the northern end of Park Avenue, moments from the city's finest boutiques, restaurants, cultural landmarks and the historic Winter Park Golf Course. Within this exclusive enclave, residence 649 occupies one of the community's most private settings. Beyond the stately brick

    Drew Henner PREMIER SOTHEBY'S INTL. REALTY

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

    $1,840,000

    Sold Jun 09, 2026

    640 Arjay Way, Winter Park, FL 32789

    • 5 Beds
    • 5 Baths
    • 3,953 Sq Ft
    • Built 1958

    Last Sold Summary

    • 8% Below List Price
    • $465/SF
    • 107 Days On Market

    Current Estimated Value $1,830,954

    Last Listing Agent Farah Bloom KELLER WILLIAMS WINTER PARK

    640 Arjay Way, Winter Park, FL 32789
    • /31

      Est $1,100,398

      Not Listed For Sale

      100 S Virginia Ave Unit 315, Winter Park, FL 32789

      • 3 Beds
      • 3 Baths
      • 2,599 Sq Ft
      • Built 2009
      100 S Virginia Ave Unit 315, Winter Park, FL 32789

      Last Sold Summary

      • 10 Days On Market

  • /45

    $449,900

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,491 Sq Ft

    405 Lake Fair Ln, Winter Park, FL 32789

    Virtually Staged. Fully rebuilt, not just renovated. This Winter Park home at 405 Lake Fair Ln has been completely transformed from top to bottom, with all major systems updated and no detail overlooked, enhanced by custom architectural wood paneling that gives the exterior a modern, high-end presence and standout curb appeal. Positioned on a quiet dead-end street with no side or rear neighbors,

    Donnamarie Leiba Gough EXP REALTY LLC

    405 Lake Fair Ln, Winter Park, FL 32789
  • /2

    $1,050,000

    Sold Aug 14, 2025

    2250 Forrest Rd, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,492 Sq Ft
    • Built 1950

    Last Sold Summary

    • 12% Below List Price
    • $704/SF
    • 0 Days On Market

    Current Estimated Value $1,023,691

    Last Listing Agent Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

    2250 Forrest Rd, Winter Park, FL 32789
    • /34

      Est $1,456,823

      Not Listed For Sale

      101 S New York Ave Unit 309, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 2,966 Sq Ft
      • Built 2008
      101 S New York Ave Unit 309, Winter Park, FL 32789

      Last Sold Summary

      • 16 Days On Market

  • /41

    $1,795,000

    • 3 Beds
    • 5 Baths
    • 2,756 Sq Ft

    641 Northwood Cir, Winter Park, FL 32789

    Tucked away on a peaceful cut-de-sac in the heart of Winter Park, this striking modern residence offers a rare blend of privacy, walkability and refined design. A private courtyard entrance sets the tone, creating a serene arrival and sense of retreat from the moment you step onto the property. Inside, polished concrete floors and an open, light-filled layout define the home's contemporary

    Sandra Cuba PREMIER SOTHEBY'S INTL. REALTY

    641 Northwood Cir, Winter Park, FL 32789
  • /2

    $389,000

    Sold Apr 02, 2026

    311 E Morse Blvd Unit 7-2, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • Built 1960

    Last Sold Summary

    • 25% Below List Price
    • $432/SF
    • 567 Days On Market

    Current Estimated Value $382,718

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    311 E Morse Blvd Unit 7-2, Winter Park, FL 32789
    • /22

      Est $1,541,651

      Not Listed For Sale

      101 S New York Ave Unit 304, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 3,118 Sq Ft
      • Built 2008
      101 S New York Ave Unit 304, Winter Park, FL 32789

      Last Sold Summary

      • 32 Days On Market

  • /27

    $235,900

    Pending
    • 1 Bed
    • 1 Bath
    • 787 Sq Ft

    700 Melrose Ave Unit F21, Winter Park, FL 32789

    Under contract-accepting backup offers. Click on virtual tour link. Floor-to-ceiling dazzling views, of sparkling pond, sweepiing oaks, towering cypress trees, and lush gardens — in the center of esteemed Winter Park.This beautifully updated upstairs unit sits within the serene Winter Park Gardens complex, where your views of the shimmering pond and pool anchor a lush sprawling landscape of

    Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

    700 Melrose Ave Unit F21, Winter Park, FL 32789
  • /2

    $965,000

    Sold Jul 07, 2025

    1760 Mondrian Cir, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 2,245 Sq Ft
    • Built 2024

    Last Sold Summary

    • 1% Below List Price
    • $430/SF
    • 11 Days On Market

    Current Estimated Value $945,805

    Last Listing Agent Brian Teach COLDWELL BANKER REALTY

    1760 Mondrian Cir, Winter Park, FL 32789
    • /2

      Est $1,149,212

      Not Listed For Sale

      100 S Virginia Ave Unit 201, Winter Park, FL 32789

      • 3 Beds
      • 3 Baths
      • 2,756 Sq Ft
      • Built 2008
      100 S Virginia Ave Unit 201, Winter Park, FL 32789

      Last Sold Summary

      • 51 Days On Market

  • /28

    $460,000

    Open Sat 1PM - 4PM $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,606 Sq Ft

    950 Hanover Ave, Winter Park, FL 32789

    Preferred lender credit available. Welcome home to your peaceful retreat tucked away near the end of a quiet street with views of Lake Wilderness. Completely updated in 2017, move-in ready so you can lock and leave with peace of mind to enjoy the everyday lifestyle of Winter Park and Central Florida this amazing location offers. Full updates made in 2017 include new roof, plumbing, electrical,

    Michael Domi COMPASS FLORIDA LLC

    950 Hanover Ave, Winter Park, FL 32789
  • /2

    $482,000

    Sold May 28, 2026

    958 Hanover Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 1,378 Sq Ft
    • Built 1956

    Last Sold Summary

    • 2% Below List Price
    • $350/SF
    • 9 Days On Market

    Current Estimated Value $479,538

    Last Listing Agent Christopher Lyons AGILE GROUP REALTY

    958 Hanover Ave, Winter Park, FL 32789
    • /17

      Est $291,820

      Not Listed For Sale

      500 N Pennsylvania Ave Unit F, Winter Park, FL 32789

      • 2 Beds
      • 1 Bath
      • 709 Sq Ft
      • Built 1981
      500 N Pennsylvania Ave Unit F, Winter Park, FL 32789

      Last Sold Summary

      • 24 Days On Market

  • /20

    $695,000

    $55K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,317 Sq Ft

    432 W Swoope Ave, Winter Park, FL 32789

    A short stroll to Park Avenue in 5 minutes. Beautiful townhome, move in ready. Spacious and open floor plan with 4 bedrooms and 3.5 baths.

    Thomas Bonner COLDWELL BANKER REALTY

    432 W Swoope Ave, Winter Park, FL 32789
  • /2

    $1,300,000

    Sold May 29, 2026

    1780 Mondrian Cir, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 2,310 Sq Ft
    • Built 2023

    Last Sold Summary

    • 7% Below List Price
    • $563/SF
    • 48 Days On Market

    Current Estimated Value $1,365,808

    Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

    1780 Mondrian Cir, Winter Park, FL 32789
    • /2

      Est $313,339

      Not Listed For Sale

      500 N Pennsylvania Ave Unit E, Winter Park, FL 32789

      • 2 Beds
      • 1 Bath
      • 709 Sq Ft
      • Built 1981
      500 N Pennsylvania Ave Unit E, Winter Park, FL 32789

      Last Sold Summary

      • 99 Days On Market

Showing Results 441 - 480, Page 12 of 18

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