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Winter Park, FL Homes for Sale — Page 13 | Realty.com
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3 bedsNew constructionWith a pool

Homes for Sale in Winter Park, FL

Homes for Sale in Winter Park, FL

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24 of 351 Listings
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Homes for Sale in Winter Park, FL

24 of 351 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 7327 Forest Hill Ct #223 — photoPrice Reduced24Active

    $175,000

    2 bd · 3 ba · 1,031 sqft

    7327 Forest Hill Ct #223, Winter Park, FL

    Leda Vaz · M L VAZ REALTY INC

  2. 450 Lakewood Dr — photo88Active

    $2,500,000

    5 bd · 6 ba · 4,572 sqft

    450 Lakewood Dr, Winter Park, FL

    Vonda Fields · CHARLES RUTENBERG REALTY ORLANDO

  3. 1864 Grinnell Ter — photo43Active

    $1,599,000

    5 bd · 4 ba · 3,028 sqft

    1864 Grinnell Ter, Winter Park, FL

    Robyn Brehne-Glass · COLDWELL BANKER REALTY

  4. 525 Ololu Dr — photoPrice Reduced40Active

    $490,900

    3 bd · 3 ba · 1,786 sqft

    525 Ololu Dr, Winter Park, FL

    Gisela Rojas · CAISSA REALTY INVESTMENT INC

  5. 446 Melrose Ave — photoPrice Reduced39Active

    $1,495,000

    4 bd · 2 ba · 2,640 sqft

    446 Melrose Ave, Winter Park, FL

    Audra Wilks · PREMIER SOTHEBY'S INTL. REALTY

  6. 811 Overspin Dr — photoPrice Reduced9Active

    $329,000

    2 bd · 1 ba · 749 sqft

    811 Overspin Dr, Winter Park, FL

    Rick Singh · RICK SINGH REAL ESTATE

  7. 1441 Cardinal Ct — photoPrice Reduced85Active

    $3,995,000

    4 bd · 6 ba · 4,066 sqft

    1441 Cardinal Ct, Winter Park, FL

    Damian Bergler · CHARLES RUTENBERG REALTY ORLANDO

  8. 7454 Wynnewood Sq #188 — photo29Active

    $229,000

    3 bd · 3 ba · 1,151 sqft

    7454 Wynnewood Sq #188, Winter Park, FL

    Manoj Patel · APPLE REALTY

  9. 5143 Lazy Oaks Dr #5143 — photoPrice Reduced41Active

    $275,000

    2 bd · 2 ba · 1,008 sqft

    5143 Lazy Oaks Dr #5143, Winter Park, FL

    Mindy Machock · KELLER WILLIAMS REALTY AT THE PARKS

  10. 102 Bell Pl — photoPrice ReducedOpen house Sat, Oct 3 · 2:00 AM39Active

    $1,299,000

    4 bd · 4 ba · 2,459 sqft

    102 Bell Pl, Winter Park, FL

    Nick McKee · KELLER WILLIAMS WINTER PARK

  11. 3021 Aaron Burr Ave #3 — photo21Active

    $140,000

    2 bd · 3 ba · 1,090 sqft

    3021 Aaron Burr Ave #3, Winter Park, FL

    Daiana Garcia Medrano · NAIM REAL ESTATE LLC

  12. 950 Hanover Ave — photoPrice Reduced25Active

    $439,000

    3 bd · 2 ba · 1,606 sqft

    950 Hanover Ave, Winter Park, FL

    Michael Domi · COMPASS FLORIDA LLC

  13. 2702 Parkland Dr — photoPrice Reduced48Active

    $1,049,000

    5 bd · 3 ba · 2,656 sqft

    2702 Parkland Dr, Winter Park, FL

    Elizabeth Nordquist · NORDQUIST & COMPANY INC

  14. 2600 Euston Rd — photo36Active

    $630,000

    6 bd · 3 ba · 3,145 sqft

    2600 Euston Rd, Winter Park, FL

    Suheil Flores · AROD PARTNERS REALTY

  15. 1881 Lake Spier Dr — photo25Active

    $1,350,000

    3 bd · 2 ba · 1,750 sqft

    1881 Lake Spier Dr, Winter Park, FL

    Rafael Zenke Pinhao · NOVA REAL ESTATE SERVICES INC

  16. 1695 Lee Rd #D211 — photoPrice Reduced28Active

    $102,500

    2 bd · 1 ba · 881 sqft

    1695 Lee Rd #D211, Winter Park, FL

    Brandy Ray · LOKATION

  17. 1369 Blue Stem Ln — photoPrice Reduced46Active

    $775,000

    4 bd · 4 ba · 2,589 sqft

    1369 Blue Stem Ln, Winter Park, FL

    He Gao · U S GLORY REALTY

  18. 7393 Grand Ave — photo10Active

    $325,000

    3 bd · 2 ba · 1,518 sqft

    7393 Grand Ave, Winter Park, FL

    Latisha Smith · DREAM HOME REALTY GROUP AND ASSOCIATES LLC

  19. 1870 Staunton Ave — photo10Active

    $1,250,000

    4 bd · 4 ba · 2,525 sqft

    1870 Staunton Ave, Winter Park, FL

    Vinny Lay · COMPASS FLORIDA LLC

  20. 1131 Wildmeadow Run — photo28Active

    $825,000

    4 bd · 4 ba · 2,589 sqft

    1131 Wildmeadow Run, Winter Park, FL

    Joann Beck · BECK REALTY LLC

  21. 1570 Palmer Ave — photoPrice Reduced36Active

    $1,595,000

    4 bd · 4 ba · 3,048 sqft

    1570 Palmer Ave, Winter Park, FL

    David Auerbach · PARK TOWN REAL ESTATE LLC

  22. 541 W Canton Ave — photoPrice Reduced51Active

    $2,495,000

    4 bd · 4 ba · 3,553 sqft

    541 W Canton Ave, Winter Park, FL

    Bianca Khoury · PREMIER SOTHEBY'S INTL. REALTY

  23. 1750 Carollee Lane — photoPrice Reduced46Active

    $1,750,000

    4 bd · 4 ba · 3,249 sqft

    1750 Carollee Lane, Winter Park, FL

    Michelle Hochfelder · PREMIER SOTHEBY'S INTL. REALTY

  24. 905 Enclave Pl — photo4Active

    $1,550,000

    4 bd · 4 ba · 2,756 sqft

    905 Enclave Pl, Winter Park, FL

    Matthew Burks · CORCORAN PREMIER REALTY

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    Thomas O'Leary

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    Lic. #BK3453168

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    Winter Park, FL community profile

    Population
    31,855
    Median income
    $98,252
    Housing units
    15,404
    People per sq. mi.
    1,409.5
    Area
    22.6 sq. mi.

    Source: HJN community data

    Winter Park housing market

    September 2026 · This period is still settling

    Winter Park 12-month median sale price trend

    Selling at 97.9% of asking price

    Buyers here are paying below asking. MLS · 73 sales · as of Sep 29, 2026

    Homes that sold · County records, as of Sep 16, 2026

    Median sale price
    $632,500$389,375–$1,088,750 typical range
    Price per sq. ft.
    $379
    Sales
    60
    Paid in cash
    50.0%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

    Median list price
    $630,000
    Homes for sale
    383
    Median days on market
    17 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    40.9%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

    Median home size
    1,731 sq. ft.

    Nearby areas

    ZIP codes

    • 34747 (2,170)
    • 34787 (1,390)
    • 34746 (1,138)
    • 33897 (841)
    • 34771 (693)
    • 32757 (595)
    • 32771 (551)
    • 34714 (551)

    Cities

    • Orlando (3,872)
    • ORLANDO (3,805)
    • Kissimmee (2,015)
    • KISSIMMEE (1,990)
    • Winter Garden (694)
    • WINTER GARDEN (648)
    • Davenport (614)
    • DAVENPORT (613)