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3 bedsNew constructionWith a pool
Luxury Homes in Winter Park, FL
73 listings

Luxury Homes in Winter Park, FL

Luxury Homes in Winter Park, FL

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24 of 73 Listings
Map

Luxury Homes in Winter Park, FL

24 of 73 Listings

  1. 1350 Lyndale Blvd — photo1Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$1,499,000

4 bd · 4 ba · 3,478 sqft

1350 Lyndale Blvd, Winter Park, FL

Gabriela Santiago · PREMIER BROKERS INTERNATIONAL

  • 1441 Grove Ter — photo16Active

    $5,950,000

    5 bd · 6 ba · 5,796 sqft

    1441 Grove Ter, Winter Park, FL

    Julie Christensen · ONE LUXURY INTERNATIONAL LLC

  • 1534 Miller Ave — photo8Active

    $1,379,900

    4 bd · 4 ba · 2,984 sqft

    1534 Miller Ave, Winter Park, FL

    Kim Griffin · RE/MAX EXCLUSIVE COLLECTION

  • 1441 Palm Ave — photo16Active

    $2,449,000

    5 bd · 5 ba · 3,391 sqft

    1441 Palm Ave, Winter Park, FL

    Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

  • 1355 Hibiscus Ave — photo69Active

    $2,100,000

    5 bd · 6 ba · 4,155 sqft

    1355 Hibiscus Ave, Winter Park, FL

    Nadia Moayeri · PALMANO GROUP RE BROKERAGE LLC

  • 541 Virginia Dr — photo99Active

    $5,695,000

    4 bd · 4 ba · 4,725 sqft

    541 Virginia Dr, Winter Park, FL

    Scott Brazdo · EXP REALTY LLC

  • 1735 Demetree Dr — photo41Active

    $1,050,000

    4 bd · 3 ba · 2,787 sqft

    1735 Demetree Dr, Winter Park, FL

    Melissa Johnson · EXP REALTY LLC

  • 1200 Via Salerno — photo56Active

    $5,995,000

    5 bd · 6 ba · 5,476 sqft

    1200 Via Salerno, Winter Park, FL

    Kelly Price · KELLY PRICE & COMPANY LLC

  • 1631 Hillcrest Ave — photo56Active

    $4,500,000

    5 bd · 6 ba · 4,754 sqft

    1631 Hillcrest Ave, Winter Park, FL

    Chris Quarles · CHRIS QUARLES PROPERTIES LLC

  • 1825 Whitehall Dr — photoOpen house Sat, Nov 7 · 12:00 PM98Active

    $3,195,000

    4 bd · 6 ba · 4,311 sqft

    1825 Whitehall Dr, Winter Park, FL

    Ahmad Hassan, PA · COMPASS FLORIDA LLC

  • 1600 Legion Dr — photo76Active

    $3,495,000

    5 bd · 6 ba · 4,483 sqft

    1600 Legion Dr, Winter Park, FL

    Brian Teach · COLDWELL BANKER REALTY

  • 1681 Woodland Ave — photo16Active

    $2,629,000

    5 bd · 5 ba · 3,682 sqft

    1681 Woodland Ave, Winter Park, FL

    Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

  • 1939 Woodcrest Dr — photo58Active

    $1,349,000

    4 bd · 4 ba · 2,575 sqft

    1939 Woodcrest Dr, Winter Park, FL

    Jose Martinez Rivera LLC · LA ROSA REALTY PREMIER LLC

  • 1445 Via Sangro Pl — photo44Active

    $1,249,000

    6 bd · 6 ba · 5,021 sqft

    1445 Via Sangro Pl, Winter Park, FL

    Kevin Asenjo · COLDWELL BANKER REALTY

  • 1011 McKean Cir — photo70Active

    $6,000,000

    5 bd · 7 ba · 4,806 sqft

    1011 McKean Cir, Winter Park, FL

    Clay Wooten · UNITED REAL ESTATE PREFERRED

  • 1751 Glencoe Rd — photo67Active

    $3,390,000

    5 bd · 7 ba · 4,520 sqft

    1751 Glencoe Rd, Winter Park, FL

    Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

  • 1737 Indiana Ave — photoOpen house Sun, Nov 15 · 12:00 PM38Active

    $1,399,900

    4 bd · 4 ba · 2,984 sqft

    1737 Indiana Ave, Winter Park, FL

    Tori Nguyen · LOKATION

  • 2823 Parkland Circle — photoOpen house Sat, Nov 7 · 12:00 PM46Active

    $3,250,000

    5 bd · 6 ba · 4,459 sqft

    2823 Parkland Circle, Winter Park, FL

    Sandra Cuba · PREMIER SOTHEBY'S INTL. REALTY

  • 2613 Lafayette Ave — photo24Active

    $1,699,900

    4 bd · 4 ba · 2,661 sqft

    2613 Lafayette Ave, Winter Park, FL

    Matt Tomaszewski · CORCORAN PREMIER REALTY

  • 918 Enclave Pl — photo8Active

    $2,125,000

    5 bd · 5 ba · 3,713 sqft

    918 Enclave Pl, Winter Park, FL

    Laura Earl · CORCORAN PREMIER REALTY

  • 2119 Howard Dr — photo11Active

    $3,195,000

    5 bd · 6 ba · 4,139 sqft

    2119 Howard Dr, Winter Park, FL

    Laura Earl · CORCORAN PREMIER REALTY

  • 2007 Edwin Blvd — photo4Active

    $1,995,000

    4 bd · 4 ba · 3,314 sqft

    2007 Edwin Blvd, Winter Park, FL

    Angela Rodriguez · DREAM FINDERS REALTY GROUP CORP

  • 513 Dunraven Dr — photo21Active

    $1,950,000

    5 bd · 5 ba · 3,560 sqft

    513 Dunraven Dr, Winter Park, FL

    Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY

  • 555 E Lake Sue Ave — photo96Active

    $2,095,000

    4 bd · 4 ba · 3,776 sqft

    555 E Lake Sue Ave, Winter Park, FL

    Claudia Davidson · KELLER WILLIAMS WINTER PARK

  • 12…4

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    By bedrooms

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    Thomas O'Leary

    Realty.com

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    Listing data & MLS disclosures

    Stellar MLS
    Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

    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

    October 2026 · This period is still settling

    Winter Park 12-month median sale price trend

    Selling at 96.8% of asking price

    Buyers here are paying below asking. MLS · 65 sales · as of Oct 30, 2026

    Homes that sold · County records, as of Oct 19, 2026

    Median sale price
    $510,000$355,250–$992,500 typical range
    Price per sq. ft.
    $313
    Sales
    44
    Paid in cash
    47.7%

    Homes on the market · MLS, as of Oct 18, 2026–Oct 30, 2026

    Median list price
    $587,000
    Homes for sale
    334
    Median days on market
    24 days

    Price trend · Assessor repeat sales, as of Oct 31, 2026

    Year-over-year
    -1.9%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

    Median home size
    1,731 sq. ft.