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Buy

Start here

  • Homes for sale by state
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  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
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    3 bedsNew constructionWith a pool
    Sell

    Selling Options

    • What's my home worth?
    • Compare selling options
    • Get an instant cash offer
    • Buy before you sell

    Resources

    • How selling works
    • When should I sell?
    • Home selling tips
    • Pricing your home
    • What's worth fixing first
    • Find a seller's agent
    Home Loans
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    Homes Under $300K in Winter Garden, FL
    23 listings

    Homes Under $300K in Winter Garden, FL

    Homes Under $300K in Winter Garden, FL

    Hide Map
    23 Listings
    Map

    Homes Under $300K in Winter Garden, FL

    23 Listings

    1. 16637 La Trina Ct 5135 — photo26

    Your Winter Garden agent

    VF

    Veronica Figueroa

    The Figueroa Team LLC. eXp Realty, LLC

    The Figueroa Team LLC. eXp Realty, LLCCall Veronica
    Active

    $210,000

    3 bd · — ba · 1,876 sqft

    16637 La Trina Ct 5135, Winter Garden, FL

  • 16666 Tavira Dr 2002 — photo15Active

    $109,900

    3 bd · — ba · 1,456 sqft

    16666 Tavira Dr 2002, Winter Garden, FL

  • 16554 Avenida Del Lago 1022 — photo17Active

    $112,000

    2 bd · — ba · 1,248 sqft

    16554 Avenida Del Lago 1022, Winter Garden, FL

  • 16632 LaTrina Ct 5138 — photo23Active

    $129,900

    3 bd · — ba · 1,344 sqft

    16632 LaTrina Ct 5138, Winter Garden, FL

  • 16620 La Trina Ct 5141 — photo20Active

    $139,900

    3 bd · — ba · 1,344 sqft

    16620 La Trina Ct 5141, Winter Garden, FL

  • 16645 Rialto Drive 4296 — photo14Active

    $110,000

    — bd · — ba · 1,152 sqft

    16645 Rialto Drive 4296, Winter Garden, FL

  • 14918 Avenida de Palma 5017 — photo15Active

    $145,000

    3 bd · — ba · 1,568 sqft

    14918 Avenida de Palma 5017, Winter Garden, FL

  • 14360 Nieves Circle 4327 — photo10Active

    $105,000

    3 bd · — ba · 1,248 sqft

    14360 Nieves Circle 4327, Winter Garden, FL

  • 16604 Rialto Dr 4283 — photo17Active

    $104,900

    3 bd · — ba · 1,152 sqft

    16604 Rialto Dr 4283, Winter Garden, FL

  • 16664 Cordoba St 3128 — photoPrice Reduced16Active

    $119,900

    3 bd · — ba · 1,248 sqft

    16664 Cordoba St 3128, Winter Garden, FL

  • 16661 Tavira Dr 2117 — photo21Active

    $155,000

    3 bd · — ba · — sqft

    16661 Tavira Dr 2117, Winter Garden, FL

  • 14706 Sugura Dr 2072 — photo13Active

    $97,900

    2 bd · — ba · — sqft

    14706 Sugura Dr 2072, Winter Garden, FL

  • 14413 Palencia St 3074 — photo17Active

    $89,900

    2 bd · — ba · — sqft

    14413 Palencia St 3074, Winter Garden, FL

  • 16622 Cordoba Dr 3115 — photo21Active

    $139,900

    4 bd · — ba · — sqft

    16622 Cordoba Dr 3115, Winter Garden, FL

  • 16637 Tavira Drive 2122 — photo14Active

    $99,000

    2 bd · — ba · — sqft

    16637 Tavira Drive 2122, Winter Garden, FL

  • 14804 Sugura Dr 2108 — photoPrice Reduced19Active

    $145,000

    3 bd · — ba · 1,387 sqft

    14804 Sugura Dr 2108, Winter Garden, FL

  • 14249 Canarias Dr 1165 — photoPrice Reduced16Active

    $139,999

    3 bd · — ba · 1,352 sqft

    14249 Canarias Dr 1165, Winter Garden, FL

  • 14741 Avenida de Palma 5117 — photoPrice Reduced21Active

    $140,000

    3 bd · — ba · 1,344 sqft

    14741 Avenida de Palma 5117, Winter Garden, FL

  • 16612 Cordoba Street 3091 — photoPrice Reduced12Active

    $104,900

    3 bd · — ba · 1,232 sqft

    16612 Cordoba Street 3091, Winter Garden, FL

  • 14816 Sugura Dr 2111 — photoPrice Reduced13Active

    $99,000

    2 bd · — ba · — sqft

    14816 Sugura Dr 2111, Winter Garden, FL

  • 14438 Palos Place 3094 — photoPrice Reduced19Active

    $154,500

    4 bd · — ba · 1,680 sqft

    14438 Palos Place 3094, Winter Garden, FL

  • 16580 Menorca Dr 1140 — photoPrice Reduced17Active

    $82,500

    3 bd · — ba · — sqft

    16580 Menorca Dr 1140, Winter Garden, FL

  • 14800 Sugura Dr 2107 — photoPrice Reduced19Active

    $99,900

    2 bd · — ba · 960 sqft

    14800 Sugura Dr 2107, Winter Garden, FL

  • Explore Winter Garden homes

    By price

    • Under $300K
    • Under $500K
    • Under $700K
    • Luxury

    By bedrooms

    • 2 beds
    • 3 beds
    • 4 beds
    • 5 beds

    By type

    • Single family
    • Townhomes
    • Condos
    • Manufactured homes
    • Multi-family homes
    • Co-ops

    By feature

    • New construction
    • With a pool
    Realty.com

    L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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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.

    © 2026 Realty.com. All rights reserved.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

    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.

    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

    August 2026

    Winter Garden 12-month median sale price trend

    Selling at 99.1% of asking price

    Buyers here are paying below asking. MLS · 215 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 31, 2026

    Median sale price
    $637,500$482,250–$915,575 typical range
    Price per sq. ft.
    $263
    Sales
    252
    Paid in cash
    39.7%

    Homes on the market · MLS, as of Aug 31, 2026

    Median days on market
    33 days

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

    Year-over-year
    -4.0%