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

Luxury Homes in Winter Park, FL

Luxury Homes in Winter Park, FL

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24 of 108 Listings
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Luxury Homes in Winter Park, FL

24 of 108 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 1600 Legion Dr — photoNew76Active

    $3,495,000

    5 bd · 6 ba · 4,483 sqft

    1600 Legion Dr, Winter Park, FL

    Brian Teach · COLDWELL BANKER REALTY

  2. NewActive

    $4,695,000

    11 bd · 8 ba · 3,615 sqft

    617 N Interlachen Ave, Winter Park, FL

    Greg Owen · EASY REALTY

  3. 1681 Woodland Ave — photoNew16Active

    $2,629,000

    5 bd · 5 ba · 3,682 sqft

    1681 Woodland Ave, Winter Park, FL

    Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

  4. 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

  5. 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

  6. 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

  7. 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

  8. 1760 Oakhurst Ave — photo41Active

    $2,500,000

    5 bd · 5 ba · 3,700 sqft

    1760 Oakhurst Ave, Winter Park, FL

    Sylvester Harding · SIERRA REALTY GROUP LLC

  9. 2234 Howard Dr — photo17Active

    $2,295,000

    4 bd · 6 ba · 3,295 sqft

    2234 Howard Dr, Winter Park, FL

    Raquel Elliott · COLDWELL BANKER REALTY

  10. 1737 Indiana Ave — photo38Active

    $1,399,900

    4 bd · 4 ba · 2,984 sqft

    1737 Indiana Ave, Winter Park, FL

    Tori Nguyen · LOKATION

  11. 2823 Parkland Circle — photo46Active

    $3,250,000

    5 bd · 6 ba · 4,459 sqft

    2823 Parkland Circle, Winter Park, FL

    Sandra Cuba · PREMIER SOTHEBY'S INTL. REALTY

  12. 1602 Alabama Dr #107 — photo33Active

    $1,150,000

    2 bd · 2 ba · 993 sqft

    1602 Alabama Dr #107, Winter Park, FL

    Valerie Leary · CORCORAN PREMIER REALTY

  13. 2613 Lafayette Ave — photo12Active

    $1,699,900

    4 bd · 4 ba · 2,661 sqft

    2613 Lafayette Ave, Winter Park, FL

    Matt Tomaszewski · CORCORAN PREMIER REALTY

  14. 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

  15. 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

  16. 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

  17. 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

  18. 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

  19. 698 N New York Ave — photo52Active

    $6,195,000

    5 bd · 6 ba · 5,096 sqft

    698 N New York Ave, Winter Park, FL

    Mick Night · PREMIER SOTHEBY'S INTL. REALTY

  20. 2614 Parkland Dr — photo55Active

    $1,890,000

    4 bd · 4 ba · 3,307 sqft

    2614 Parkland Dr, Winter Park, FL

    Ryan Gaston · JW GASTON LLC

  21. 532 Langholm Dr — photo18Active

    $2,990,000

    5 bd · 5 ba · 4,050 sqft

    532 Langholm Dr, Winter Park, FL

    Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

  22. 100 S Virginia Ave #201 — photoOpen house Tue, Oct 20 · 12:30 PM39Active

    $1,450,000

    3 bd · 3 ba · 2,756 sqft

    100 S Virginia Ave #201, Winter Park, FL

    Tiffany Grindstaff · KELLY PRICE & COMPANY LLC

  23. 1951 Winter Park Rd — photo73Active

    $2,089,000

    4 bd · 4 ba · 3,479 sqft

    1951 Winter Park Rd, Winter Park, FL

    Holly Wilton · KELLER WILLIAMS WINTER PARK

  24. 120 Broadview Ave — photo34Active

    $1,250,000

    3 bd · 2 ba · 1,747 sqft

    120 Broadview Ave, Winter Park, FL

    Catherine D'Amico · FANNIE HILLMAN & ASSOCIATES

12…5

About Luxury Homes in Winter Park, FL

Luxury Homes in Winter Park, FL: 108 active listings as of October 19, 2026, 20:43 UTC.

Property types among these 108 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property typeListingsShare
Single Family Residence9588.0%
Townhouse87.4%
Condominium54.6%

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The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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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.
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    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

    Winter Park 12-month median sale price trend

    Selling at 97.9% of asking price

    Buyers here are paying below asking. MLS · 84 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 30, 2026

    Median sale price
    $566,750$404,625–$1,046,250 typical range
    Price per sq. ft.
    $342
    Sales
    108
    Paid in cash
    43.5%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

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

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

    Year-over-year
    27.8%

    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.