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3 bedsNew constructionWith a pool
Homes Under $2.5M in Winter Park, FL
315 listings

Homes Under $2.5M in Winter Park, FL

Homes Under $2.5M in Winter Park, FL

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24 of 315 Listings
Map

Homes Under $2.5M in Winter Park, FL

24 of 315 Listings

  1. 7560 Aloma Pines Ct — photo23

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$365,000

3 bd · 3 ba · 1,866 sqft

7560 Aloma Pines Ct, Winter Park, FL

Jessica Macias · KELLER WILLIAMS ADVANTAGE III

  • 100 S Interlachen Ave #401 — photoNew25Active

    $850,000

    3 bd · 2 ba · 1,639 sqft

    100 S Interlachen Ave #401, Winter Park, FL

    Mary Colton · FANNIE HILLMAN & ASSOCIATES

  • 2500 Lee Rd #123 — photoNew32Active

    $169,900

    1 bd · 1 ba · 645 sqft

    2500 Lee Rd #123, Winter Park, FL

    Scott Sheldon · HOME WISE REALTY GROUP, INC.

  • 3150 Shady Pine Ave — photoNew39Active

    $439,900

    4 bd · 2 ba · 1,624 sqft

    3150 Shady Pine Ave, Winter Park, FL

    Sarita Cabrera · WATSON REALTY CORP

  • 188 Sandlewood #1 — photo25Active

    $290,000

    2 bd · 3 ba · 1,133 sqft

    188 Sandlewood #1, Winter Park, FL

    Tom Noelke · NOELKE REALTY

  • 712 Baffie Ave — photoNew14Active

    $448,000

    3 bd · 1 ba · 1,304 sqft

    712 Baffie Ave, Winter Park, FL

    George Bateman, III · RP INVESTMENT REALTY LLC

  • 5405 Justine Way — photoNew21Active

    $399,900

    3 bd · 2 ba · 1,247 sqft

    5405 Justine Way, Winter Park, FL

    Yanira Suarez · LPT REALTY, LLC

  • 200 Saint Andrews Blvd #704 — photo40Active

    $159,000

    1 bd · 1 ba · 793 sqft

    200 Saint Andrews Blvd #704, Winter Park, FL

    Alexis Jacobsen · EXP REALTY LLC

  • 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

  • 1187 Sawmill Court — photo5Active

    $5,000

    3 bd · 2 ba · 1,229 sqft

    1187 Sawmill Court, Winter Park, FL

    Jaime L Boone · Jaime L Boone LLC

  • 870 N Phelps Ave — photo15Active

    $850,000

    4 bd · 3 ba · 2,301 sqft

    870 N Phelps Ave, Winter Park, FL

    Christina Frucci · RE/MAX TOWN & COUNTRY REALTY

  • 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

  • 7498 Aloma Pines Ct — photo39Active

    $364,900

    3 bd · 3 ba · 1,872 sqft

    7498 Aloma Pines Ct, Winter Park, FL

    Marian Coaxum · KELLER WILLIAMS REALTY AT THE PARKS

  • 266 N Ranger Blvd — photo33Active

    $724,900

    4 bd · 3 ba · 1,692 sqft

    266 N Ranger Blvd, Winter Park, FL

    Moises Rivera · ELITE PROPERTY REAL ESTATE LLC

  • 1256 S Pennsylvania Ave #9 — photo46Active

    $950,000

    3 bd · 3 ba · 1,957 sqft

    1256 S Pennsylvania Ave #9, Winter Park, FL

    Drew Henner · PREMIER SOTHEBY'S INTL. REALTY

  • 1695 Lee Rd #C206 — photo24Active

    $140,000

    2 bd · 1 ba · 881 sqft

    1695 Lee Rd #C206, Winter Park, FL

    Ingrid Garcia Rodriguez · INVESTMENT REALTY

  • 7786 Fox Knoll Pl — photo55Active

    $410,500

    4 bd · 2 ba · 1,301 sqft

    7786 Fox Knoll Pl, Winter Park, FL

    Eric Senate · NIZZ REALTY INC

  • 1225 Sharon Pl — photo78Active

    $1,749,000

    5 bd · 4 ba · 3,097 sqft

    1225 Sharon Pl, Winter Park, FL

    Anthony Consalvo · FLORIDA ONE REAL ESTATE LLC

  • 1003 Golfside Dr — photo28Active

    $769,900

    3 bd · 3 ba · 2,145 sqft

    1003 Golfside Dr, Winter Park, FL

    Lina Paeres · QP HOMES REALTY LLC

  • 173 Scottsdale Sq #173 — photo13Active

    $100,000

    1 bd · 1 ba · 785 sqft

    173 Scottsdale Sq #173, Winter Park, FL

    Paola Jimenez · AXEN REALTY, LLC

  • 1250 S Denning Dr #119 — photo31Active

    $265,000

    2 bd · 2 ba · 908 sqft

    1250 S Denning Dr #119, Winter Park, FL

    Justin McCarthy · FANNIE HILLMAN & ASSOCIATES

  • 1660 Orange Ave — photoOpen house Sat, Oct 3 · 1:00 PM61Active

    $479,900

    3 bd · 2 ba · 1,614 sqft

    1660 Orange Ave, Winter Park, FL

    Gaby Murillo · EXP REALTY LLC

  • 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

  • 739 Roughbeard Rd — photo45Active

    $780,000

    5 bd · 3 ba · 2,194 sqft

    739 Roughbeard Rd, Winter Park, FL

    John Harbuck · SERHANT

  • 12…14

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    Your local brokerage

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    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Listing data & MLS disclosures

    Space Coast MLS (Space Coast Association of REALTORS)
    IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
    Information is deemed reliable but not guaranteed.
    Listing information ©2026 Space Coast MLS, Inc®. All Rights Reserved. Last Updated: 2026-09-29 11:01:04 UTC
    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

    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.