11,850

Homes in ZIP Code 32789

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  • /32

    $470,000

    $80K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,718 Sq Ft

    240 Orange Terrace Dr, Winter Park, FL 32789

    MOVE IN READY - FENCED IN YARD - NO HOA, PRIME WINTER PARK LOCATION, CLOSE TO I-4! Nestled in the heart of Winter Park near Lake Killarney, this beautifully updated 4-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and style. Just minutes from Fairbanks and I-4, you’ll enjoy quick access to top shopping, dining, and all that Winter Park has to offer.Fully renovated in

    Susan Pinnock A+ REALTY PROFESSIONALS, INC

    240 Orange Terrace Dr, Winter Park, FL 32789
  • /2

    $560,000

    Sold Aug 19, 2025

    1339 Orchid Ave, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 789 Sq Ft
    • Built 1953

    Last Sold Summary

    • 12% Below List Price
    • $710/SF
    • 46 Days On Market

    Current Estimated Value $548,845

    Last Listing Agent Barbara Allen ABIDE REALTY

    1339 Orchid Ave, Winter Park, FL 32789
    • /2

      Est $131,067

      Not Listed For Sale

      1695 Lee Rd Unit D205, Winter Park, FL 32789

      • 2 Beds
      • 1 Bath
      • 881 Sq Ft
      • Built 1966
      1695 Lee Rd Unit D205, Winter Park, FL 32789

      Last Sold Summary

      • 11 Days On Market

  • /31

    $1,495,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 2,838 Sq Ft

    2408 Lafayette Ave, Winter Park, FL 32789

    This custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to create a harmonious flow, perfect for both entertaining and everyday life. The abundance of windows bathes the interiors in natural light, creating a bright and airy ambiance. The office/study is set apart for

    Matthew Burks CORCORAN PREMIER REALTY

    2408 Lafayette Ave, Winter Park, FL 32789
  • /2

    $975,000

    Sold Mar 25, 2026

    456 Carolina Ave, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 1,615 Sq Ft
    • Built 2004

    Last Sold Summary

    • 3% Below List Price
    • $604/SF
    • 9 Days On Market

    Current Estimated Value $972,808

    Last Listing Agent Heather Frazee FANNIE HILLMAN & ASSOCIATES

    456 Carolina Ave, Winter Park, FL 32789
    • /31

      Est $137,782

      Not Listed For Sale

      1695 Lee Rd Unit C203, Winter Park, FL 32789

      • 2 Beds
      • 1 Bath
      • 881 Sq Ft
      • Built 1966
      1695 Lee Rd Unit C203, Winter Park, FL 32789

      Last Sold Summary

      • 4 Days On Market

  • /37

    $2,750,000

    Pending
    • 5 Beds
    • 5 Baths
    • 4,917 Sq Ft

    1630 Lasbury Ave, Winter Park, FL 32789

    Under contract-accepting backup offers. The seller has just completed a full renovation.Bathrooms have been entirely gutted and updated with new tiles, fixtures, and lighting. All lighting throughout the home has been replaced, and fresh paint has been applied throughout. Situated on a spacious double lot spanning over 1/3 acres, this home offers a private retreat, complete with an impressive

    Teresa Chris Harralson COMPASS FLORIDA, LLC

    1630 Lasbury Ave, Winter Park, FL 32789
  • /2

    $475,000

    Sold Oct 14, 2025

    621 Symonds Ave, Winter Park, FL 32789

    • Land
    • 5,662 Sq Ft
    • $3,653,846 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 147 Days On Market

    Current Estimated Value $480,621

    Last Listing Agent Emily Williams FANNIE HILLMAN & ASSOCIATES

    621 Symonds Ave, Winter Park, FL 32789
    • /4

      Est $127,084

      Not Listed For Sale

      1695 Lee Rd Unit D109, Winter Park, FL 32789

      • 1 Bed
      • 1 Bath
      • 638 Sq Ft
      • Built 1966
      1695 Lee Rd Unit D109, Winter Park, FL 32789

      Last Sold Summary

      • 0 Days On Market

  • /37

    $1,185,999

    • 6 Beds
    • 4 Baths
    • 2,282 Sq Ft

    726 N Pennsylvania Ave, Winter Park, FL 32789

    Opportunities like this don’t come around often, this is currently the only duplex available within walking distance of Park Avenue and just minutes from Rollins College, placing it directly in one of the most consistent, high-demand rental pockets in Winter Park. With two 3-bedroom, 2-bathroom units (6 bedrooms total), this property is ideally positioned for strong, stable income. Live in one

    Brandon Geers COMPASS FLORIDA LLC

    726 N Pennsylvania Ave, Winter Park, FL 32789
  • /58

    $2,895,000

    Pending
    • 5 Beds
    • 4.5 Baths
    • 4,091 Sq Ft

    670 Williams Dr, Winter Park, FL 32789

    Graceful and timeless, this classic Southern-inspired residence by esteemed builder Charles Clayton sits on a generous lot in Winter Park’s coveted Park Grove neighborhood and makes a striking first impression with beautifully composed architecture, charming dormer windows, a sweeping front porch with historic reclaimed Detroit brick flooring, and curated landscaping. Inside, the foyer unfolds

    MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    670 Williams Dr, Winter Park, FL 32789
    • /27

      Est $193,079

      Not Listed For Sale

      1695 Lee Rd Unit A115, Winter Park, FL 32789

      • 3 Beds
      • 2 Baths
      • 1,149 Sq Ft
      • Built 1966
      1695 Lee Rd Unit A115, Winter Park, FL 32789

      Last Sold Summary

      • 167 Days On Market

  • /51

    $1,395,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 2,922 Sq Ft

    1347 Chapman Cir, Winter Park, FL 32789

    Under contract-accepting backup offers. Beautiful Windsong custom home completely reimagined with a sophisticated interior design overhaul that now presents as a true Winter Park boutique luxury residence. This stunning 4 bedroom, 3.5 bath home blends timeless elegance, thoughtful craftsmanship, and warm entertaining spaces in one of the area’s most sought-after neighborhoods. Every room feels

    Justin Pekarek ORLANDO PROPERTY ADVISORS

    1347 Chapman Cir, Winter Park, FL 32789
  • /2

    $1,740,000

    Sold Aug 29, 2025

    443 Beloit Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,964 Sq Ft
    • Built 1983

    Last Sold Summary

    • 3% Below List Price
    • $587/SF
    • 0 Days On Market

    Current Estimated Value $1,755,162

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    443 Beloit Ave, Winter Park, FL 32789
    • /2

      Est $249,708

      Not Listed For Sale

      1500 Gay Rd Unit 8B, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 1,026 Sq Ft
      • Built 1972
      1500 Gay Rd Unit 8B, Winter Park, FL 32789

      Last Sold Summary

      • 16 Days On Market

  • /78

    $2,500,000

    • 5 Beds
    • 6 Baths
    • 4,572 Sq Ft

    450 Lakewood Dr, Winter Park, FL 32789

    Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within walking distance of the world-class dining and boutiques of Park Avenue, views of Lake Osceola with easy lake access, with a coveted Winter Park location and top notch schools. This 5-bedroom, 4-full and 2-half-bath pool home

    Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

    450 Lakewood Dr, Winter Park, FL 32789
  • /2

    $940,000

    Sold Aug 29, 2025

    1840 Biscayne Dr, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,646 Sq Ft
    • Built 2024

    Last Sold Summary

    • 1% Below List Price
    • $355/SF
    • 17 Days On Market

    Current Estimated Value $949,972

    Last Listing Agent Jennifer King CORCORAN PREMIER REALTY

    1840 Biscayne Dr, Winter Park, FL 32789
    • /2

      Est $1,820,137

      Not Listed For Sale

      1764 Elizabeths Walk, Winter Park, FL 32789

      • 4 Beds
      • 4 Baths
      • 3,989 Sq Ft
      • Built 2012
      1764 Elizabeths Walk, Winter Park, FL 32789

      Last Sold Summary

      • 159 Days On Market

  • /22

    $499,000

    $80K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,514 Sq Ft

    2560 Franklin Ave, Winter Park, FL 32789

    Come see this charming 4 bed, 2 bath, 2 story home in Winter Park/ Lake Killarney location, 6 mins to downtown Winter park & Winter Park Village with an outdoor shopping center featuring many shops & restaurants. Convenience to Wholefood & Publix Supermarket. Quiet neighborhood with No HOA fees. Its stone elevation gives a captivating curb appeal. Situated on a generous 0.34 acres lot. The

    Jiraporn Wasserman LoKation

    2560 Franklin Ave, Winter Park, FL 32789
  • /2

    $669,000

    Sold Mar 26, 2026

    681 Overspin Dr, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 2,220 Sq Ft
    • Built 2004

    Last Sold Summary

    • 2% Below List Price
    • $301/SF
    • 34 Days On Market

    Current Estimated Value $666,441

    Last Listing Agent Gail Higley RE/MAX SELECT GROUP

    681 Overspin Dr, Winter Park, FL 32789
    • /11

      Est $249,747

      Not Listed For Sale

      287 Sandlewood Trail Unit 4, Winter Park, FL 32789

      • 2 Beds
      • 2.5 Baths
      • 960 Sq Ft
      • Built 1984
      287 Sandlewood Trail Unit 4, Winter Park, FL 32789

      Last Sold Summary

      • 182 Days On Market

  • /45

    $1,070,000

    Open Sun 2PM - 4PM $30K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,916 Sq Ft

    1611 Chestnut Ave, Winter Park, FL 32789

    Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this fully renovated 4-bedroom, 4-bath home delivers the rarest combination: the soul of an established neighborhood, unique charm and character, and the bones of new construction. Gutted to the studs and rebuilt with intention, every major system is new — electrical, Carrier ACs, roof, ductwork, drywall,

    Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

    1611 Chestnut Ave, Winter Park, FL 32789
  • /2

    $1,675,000

    Sold May 08, 2026

    1560 Woodland Ave, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,851 Sq Ft
    • Built 1990

    Last Sold Summary

    • 9% Below List Price
    • $435/SF
    • 16 Days On Market

    Current Estimated Value $1,793,602

    Last Listing Agent Chris Creegan CREEGAN GROUP

    1560 Woodland Ave, Winter Park, FL 32789
    • /35

      Est $255,666

      Not Listed For Sale

      215 Sandlewood Trail Unit 7, Winter Park, FL 32789

      • 2 Beds
      • 2.5 Baths
      • 960 Sq Ft
      • Built 1986
      215 Sandlewood Trail Unit 7, Winter Park, FL 32789

      Last Sold Summary

      • 5 Days On Market

  • /62

    $2,235,000

    $145K PRICE DROP Pending
    • 3 Beds
    • 3 Baths
    • 3,818 Sq Ft

    1624 Barcelona Way, Winter Park, FL 32789

    Under contract-accepting backup offers. Totally traditional luxury single-story home is located in the desirable Sevilla neighborhood in Winter Park. Sitting high and dry on approximately a half-acre beautifully landscaped lot. Original home was mostly gutted down to the studs in 2011-2012 and COMPLETELY re-done. Multi-generational potential as this home has a complete attached guesthouse.

    Jan Walker PREMIER SOTHEBY'S INTL. REALTY

    1624 Barcelona Way, Winter Park, FL 32789
  • /2

    $2,232,000

    Sold Apr 17, 2026

    660 Osceola Ave Unit 101, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 2,714 Sq Ft
    • Built 1999

    Last Sold Summary

    • 3% Below List Price
    • $822/SF
    • 145 Days On Market

    Current Estimated Value $2,214,577

    Last Listing Agent Richard Traynor FLORIDA ONE REAL ESTATE LLC

    660 Osceola Ave Unit 101, Winter Park, FL 32789
    • /2

      Est $265,975

      Not Listed For Sale

      311 Sandlewood Trail Unit 4, Winter Park, FL 32789

      • 2 Beds
      • 2.5 Baths
      • 980 Sq Ft
      • Built 1984
      311 Sandlewood Trail Unit 4, Winter Park, FL 32789

      Last Sold Summary

      • 5 Days On Market

  • /44

    $709,000

    $30K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft

    1701 Goodrich Ave, Winter Park, FL 32789

    Welcome to this thoughtfully updated Winter Park home ideally on a spacious corner lot with a two-car garage offering excellent storage and everyday convenience. This home offers a flexible layout featuring two bedrooms plus an office that can function as a third bedroom, ideal for working from home or accommodating guests. Hardwood floors run throughout, adding warmth and character. Major system

    Audra Wilks PREMIER SOTHEBY'S INTL. REALTY

    1701 Goodrich Ave, Winter Park, FL 32789
  • /2

    $300,000

    Sold Mar 27, 2026

    1313 S Denning Dr, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft
    • Built 1950

    Last Sold Summary

    • $176/SF

    Current Estimated Value $316,316

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

    1313 S Denning Dr, Winter Park, FL 32789
    • /2

      Est $587,436

      Not Listed For Sale

      777 S Denning Dr Unit B, Winter Park, FL 32789

      • 3 Beds
      • 3 Baths
      • 1,762 Sq Ft
      • Built 2004
      777 S Denning Dr Unit B, Winter Park, FL 32789

      Last Sold Summary

      • 37 Days On Market

  • /37

    $2,300,000

    Pending
    • 5 Beds
    • 4 Baths
    • 4,021 Sq Ft

    800 Juanita Rael, Winter Park, FL 32789

    Under contract-accepting backup offers. Welcome to an exceptional opportunity in the highly desirable Park Grove community, an impeccably updated one-story residence ideally situated just moments from the vibrant shops and dining of Park Avenue and all that downtown Winter Park has to offer. With charming curb appeal, pristine landscaping and timeless architectural appeal, this home makes a

    Mick Night PREMIER SOTHEBY'S INTL. REALTY

    800 Juanita Rael, Winter Park, FL 32789
  • /2

    $360,000

    Sold Nov 20, 2025

    611 Ololu Dr, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,145 Sq Ft
    • Built 1973

    Last Sold Summary

    • 1% Above List Price
    • $314/SF
    • 7 Days On Market

    Current Estimated Value $371,963

    Last Listing Agent Amanda Johnson HOMERUN REALTY, LLC

    611 Ololu Dr, Winter Park, FL 32789
    • /16

      Est $327,485

      Not Listed For Sale

      2038 Jewell Ave, Winter Park, FL 32789

      • 2 Beds
      • 1 Bath
      • 809 Sq Ft
      • Built 1956
      2038 Jewell Ave, Winter Park, FL 32789

      Last Sold Summary

      • 4 Days On Market

  • /89

    $8,950,000

    • 7 Beds
    • 11 Baths
    • 11,255 Sq Ft

    1120 Preserve Point Dr, Winter Park, FL 32789

    In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths.

    Hal George PREMIER SOTHEBY'S INTL. REALTY

    1120 Preserve Point Dr, Winter Park, FL 32789
  • /2

    $1,535,000

    Sold Mar 30, 2026

    507 Country Club Dr, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,985 Sq Ft
    • Built 2020

    Last Sold Summary

    • 1% Below List Price
    • $514/SF
    • 27 Days On Market

    Current Estimated Value $1,534,554

    Last Listing Agent Lianna D'Angelo SOTERA LIVING

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

      Est $707,734

      Not Listed For Sale

      1130 Washington Ave Unit 11C, Winter Park, FL 32789

      • 3 Beds
      • 2.5 Baths
      • 2,069 Sq Ft
      • Built 1981
      1130 Washington Ave Unit 11C, Winter Park, FL 32789

      Last Sold Summary

      • 6 Days On Market

  • /65

    $3,995,000

    $655K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,181 Sq Ft

    1161 Valencia Ave, Winter Park, FL 32789

    Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Meticulously maintained with great inspection. Completed in 2021, the residence has 4,181 square feet of thoughtfully designed living space, including four bedrooms each with a private ensuite bath and an

    Lisa Mahjoub THE REAL ESTATE COLLECTION LLC

    1161 Valencia Ave, Winter Park, FL 32789
  • /2

    $1,000,500

    Sold Dec 11, 2025

    210 E Rockwood Way, Winter Park, FL 32789

    • 3 Beds
    • 1.5 Baths
    • 1,431 Sq Ft
    • Built 1950

    Last Sold Summary

    • $699/SF
    • 0 Days On Market

    Current Estimated Value $994,487

    Last Listing Agent Penny Puente DALTON WADE INC

    210 E Rockwood Way, Winter Park, FL 32789
    • /2

      Est $981,459

      Not Listed For Sale

      627 N Interlachen Ave Unit B, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 1,610 Sq Ft
      • Built 1981
      627 N Interlachen Ave Unit B, Winter Park, FL 32789

      Last Sold Summary

      • 164 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

Showing Results 521 - 560, Page 14 of 18

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