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3 bedsNew constructionWith a pool
Homes Under $400K in Winter Garden, FL
182 listings

Homes Under $400K in Winter Garden, FL

Homes Under $400K in Winter Garden, FL

Show Map
24 of 182 Listings
Map

Homes Under $400K in Winter Garden, FL

24 of 182 Listings

  1. listing photoNew25

Your Winter Garden agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLCCall Veronica
Active

$239,900

3 bd · 1 ba · 814 sqft

Address withheld · Winter Garden, FL

Martha Grasty · EXP REALTY LLC

  • 159 9th St — photo40Active

    $369,900

    3 bd · 2 ba · 1,188 sqft

    159 9th St, Winter Garden, FL

    Martha Grasty · EXP REALTY LLC

  • 14445 Nieves Circle — photo35Active

    $158,000

    3 bd · — ba · — sqft

    14445 Nieves Circle, Winter Garden, FL

  • 14501 Grove Resort Ave #3239 — photo29Active

    $165,000

    2 bd · 2 ba · 1,375 sqft

    14501 Grove Resort Ave #3239, Winter Garden, FL

    Lesley O'Neal · FLARE PROPERTIES LLC

  • 5705 New Independence Pkwy — photo29Active

    $399,900

    3 bd · 2 ba · 1,751 sqft

    5705 New Independence Pkwy, Winter Garden, FL

    Charles Watson · MARK SPAIN REAL ESTATE

  • 14452 Vista Del Lago Blvd 3059 — photo14Active

    $149,900

    2 bd · — ba · — sqft

    14452 Vista Del Lago Blvd 3059, Winter Garden, FL

  • 87 Windtree Ln #K — photo19Active

    $189,000

    2 bd · 2 ba · 918 sqft

    87 Windtree Ln #K, Winter Garden, FL

    Shelley Dawson · COMPASS FLORIDA LLC

  • 14501 Grove Resort Ave #1440 — photo67Active

    $159,999

    2 bd · 2 ba · 1,375 sqft

    14501 Grove Resort Ave #1440, Winter Garden, FL

    James Donovan · TEAM DONOVAN

  • 14292 Vista Del Lago Blvd 4233 — photo14Active

    $157,000

    3 bd · — ba · 1,152 sqft

    14292 Vista Del Lago Blvd 4233, Winter Garden, FL

  • 16549 Menorca Drive 1104 — photo14Active

    $109,900

    3 bd · — ba · 1,512 sqft

    16549 Menorca Drive 1104, Winter Garden, FL

  • 1444 Kenny Ct — photo29Active

    $350,000

    3 bd · 2 ba · 1,352 sqft

    1444 Kenny Ct, Winter Garden, FL

    Jenny Wemert · WEMERT GROUP REALTY LLC

  • 15613 Boggy Oak Cir #110a — photo31Active

    $299,900

    2 bd · 2 ba · 1,216 sqft

    15613 Boggy Oak Cir #110a, Winter Garden, FL

    Aileen Frauman · COLEDEV REAL ESTATE LLC

  • 14732 Avenida de Palma 5036 — photo16Active

    $260,000

    2 bd · — ba · 1,568 sqft

    14732 Avenida de Palma 5036, Winter Garden, FL

  • 345 E Maple St — photo1Active

    $295,000

    2 bd · 1 ba · 556 sqft

    345 E Maple St, Winter Garden, FL

    Alexia Clemens · EXP REALTY LLC

  • 1300 Eastern Pecan Pl #208 — photoOpen house Sun, Nov 1 · 12:30 PM63Active

    $298,500

    3 bd · 2 ba · 1,453 sqft

    1300 Eastern Pecan Pl #208, Winter Garden, FL

    Mildred Hershiser · EXP REALTY LLC

  • 14630 Avenida De Palma 5049 — photo11Active

    $149,000

    3 bd · — ba · — sqft

    14630 Avenida De Palma 5049, Winter Garden, FL

  • 8067 Glenlloyd Ave — photoPrice Reduced25Active

    $394,000

    3 bd · 3 ba · 1,626 sqft

    8067 Glenlloyd Ave, Winter Garden, FL

    Jacquelyn Voigt · KELLER WILLIAMS REALTY AT THE LAKES

  • 14501 Grove Resort Ave #1218 — photo26Active

    $235,000

    2 bd · 2 ba · 1,265 sqft

    14501 Grove Resort Ave #1218, Winter Garden, FL

    Kim Goldin · KELLER WILLIAMS ADVANTAGE REALTY

  • 341 Southern Pecan Cir #202 — photoPrice Reduced39Active

    $210,000

    1 bd · 1 ba · 738 sqft

    341 Southern Pecan Cir #202, Winter Garden, FL

    Merly Esgro · IAD REAL ESTATE

  • 1069 Mildred Dixon Way — photo16Active

    $275,000

    3 bd · 2 ba · 1,036 sqft

    1069 Mildred Dixon Way, Winter Garden, FL

    Robert Christiano · COLDWELL BANKER REALTY

  • 14501 Grove Resort Ave #3631 — photo40Active

    $164,900

    2 bd · 2 ba · 1,375 sqft

    14501 Grove Resort Ave #3631, Winter Garden, FL

    Allan Sutton · SUN CREST FLORIDA PROPERTIES

  • 14501 Grove Resort #1723 — photo48Active

    $344,900

    3 bd · 3 ba · 1,544 sqft

    14501 Grove Resort #1723, Winter Garden, FL

    Ciro Noccioli Monteiro Alves · LPT REALTY, LLC

  • 14501 Grove Resort Ave #2539 — photo41Active

    $163,000

    2 bd · 2 ba · 1,375 sqft

    14501 Grove Resort Ave #2539, Winter Garden, FL

    Bill Traback · MBI REALTY LLC

  • 14066 Avenue Of The Groves — photoPrice Reduced46Active

    $329,000

    2 bd · 3 ba · 1,077 sqft

    14066 Avenue Of The Groves, Winter Garden, FL

    Russ Razzani · RAZZANI INTERNATIONAL REALTY

  • 12…8

    Explore Winter Garden homes

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    By feature

    • New Construction Homes
    • Homes with a Pool
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    • Open Houses
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    Your Winter Garden agent

    VF

    Veronica Figueroa

    The Figueroa Team LLC. eXp Realty, LLC

    The Figueroa Team LLC. eXp Realty, LLCCall Veronica

    Listing data & MLS disclosures

    NY State MLS
    The data relating to real estate for sale on this website comes in part from the Internet Data exchange (IDX) program of the New York State Alliance MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Real estate listings held by brokerage firms other than Realty.com, are indicated by detailed information about them such as the name of the listing firms. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither the listing broker(s) nor Realty.com shall be responsible for any typographical errors, misinformation, misprints, and shall be held totally harmless. Copyright © 2026 New York State Alliance and participating MLS's - CNYIS, UNYREIS and WNYREIS. All Rights Reserved.
    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 Garden, FL community profile

    Population
    50,261
    Median income
    $102,195
    Housing units
    18,962
    People per sq. mi.
    562.2
    Area
    89.4 sq. mi.

    Source: HJN community data

    Winter Garden housing market

    October 2026 · This period is still settling

    Winter Garden 12-month median sale price trend

    Selling at 97.9% of asking price

    Buyers here are paying below asking. MLS · 113 sales · as of Oct 23, 2026

    Homes that sold · County records, as of Oct 12, 2026

    Median sale price
    $620,000$453,767–$892,818 typical range
    Price per sq. ft.
    $253
    Sales
    95
    Paid in cash
    37.9%

    Homes on the market · MLS, as of Oct 18, 2026–Oct 23, 2026

    Median list price
    $575,000
    Homes for sale
    772
    Median days on market
    33 days

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

    Year-over-year
    -5.3%

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

    Median home size
    2,211 sq. ft.