• HOME
  • SEARCH
    1. SEARCH HOMES IN OCALA, FL
    2. SEARCH HOMES IN JACKSONVILLE, FL
    3. SEARCH HOMES IN TAMPA, FL
    4. SEARCH HOMES IN SARASOTA, FL
    5. SEARCH HOMES IN FLORIDA KEYS
    6. SEARCH HOMES ACROSS ATLANTA, GA
    7. SEARCH OCEANFRONT HOMES IN FL
    8. OCALA LUXURY HOMES
    9. AFFORDABILITY CALCULATOR
  • ABOUT US
  • BUY
    1. FEATURED LISTINGS
    2. BUYERS
    3. ALL LISTINGS
    4. FINANCING
  • SELL
    1. SELLERS
    2. SELL MY HOME
    3. HOME VALUATION
    4. SOLD LISTINGS
  • AS SEEN ON HGTV 'SELLING FLORIDA'
  • EQUESTRIAN COLLECTION
  • REVIEWS
  • JOIN THE GAILEYS
  • MEDIA
  • CONTACT
    • Register
    • Sign In
    Filters Reset
    Save Search (2)
    Save your search to get Alerts
    1.2K Properties

    1,200 Properties Available In Winter Haven

    • Newest Listings
    • Default
    • Price-High To Low
    • Price-Low To High
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    FL >Winter Haven >
    Market Insights
    • 658 LAKE DEXTER CIR, Winter Haven, FL 33884
      1/36 36
      New

      $ 245,900

      3 Beds2 Baths1,131 SqFt

      658 LAKE DEXTER CIR, Winter Haven, FL 33884

      Single Family Home

      Listed by COLDWELL BANKER REALTY

      Stellar MLS
    • 1011 BILTMORE DR NW, Winter Haven, FL 33881
      1/22 22
      New

      $ 1,795

      3 Beds2 Baths1,605 SqFt

      1011 BILTMORE DR NW, Winter Haven, FL 33881

      Single Family Home

      Listed by SUPERIOR PROPERTY MGMT & SALES

      Stellar MLS
    • 1102 BERKLEY LN, Winter Haven, FL 33880
      1/57 57
      Open Sat 11AM-2PM

      $ 469,000

      5 Beds3 Baths2,589 SqFt

      1102 BERKLEY LN, Winter Haven, FL 33880

      Single Family Home

      Listed by OPULENT REALTY INTERNATIONAL

      Stellar MLS
    • 141 AVENUE E SW, Winter Haven, FL 33880
      1/9 9
      New

      $ 450,000

      800 SqFt

      141 AVENUE E SW, Winter Haven, FL 33880

      Commercial

      Listed by KELLER WILLIAMS REALTY SMART 1

      Stellar MLS
    • 141 AVENUE E SW, Winter Haven, FL 33880
      1/9 9
      New

      $ 24,000

      800 SqFt

      141 AVENUE E SW, Winter Haven, FL 33880

      Commercial

      Listed by KELLER WILLIAMS REALTY SMART 1

      Stellar MLS
    • 1938 SARAH ST, Winter Haven, FL 33884
      1/40 40
      New

      $ 2,100

      4 Beds3 Baths1,874 SqFt

      1938 SARAH ST, Winter Haven, FL 33884

      Single Family Home

      Listed by STAR REALTY OF WINTER HAVEN

      Stellar MLS
    • 2406 1ST ST N, Winter Haven, FL 33881
      1/7 7
      New

      $ 25,000

      0.1 Acres

      2406 1ST ST N, Winter Haven, FL 33881

      Vacant Land

      Listed by EMPIRE NETWORK REALTY

      Stellar MLS
    • 1476 AVENUE F NE, Winter Haven, FL 33881
      1/28 28
      New

      $ 435,900

      5 Beds2 Baths2,680 SqFt

      1476 AVENUE F NE, Winter Haven, FL 33881

      Single Family Home

      Listed by COLDWELL BANKER REALTY

      Stellar MLS
    • 1497 LEAMINGTON LN, Winter Haven, FL 33884
      1/21 21
      New

      $ 343,967

      4 Beds3 Baths2,405 SqFt

      1497 LEAMINGTON LN, Winter Haven, FL 33884

      Single Family Home

      Listed by ADAMS HOMES REALTY

      Stellar MLS
    • 2021 OLIVER PL, Winter Haven, FL 33881
      1/65 65
      New

      $ 269,900

      3 Beds2 Baths1,627 SqFt

      2021 OLIVER PL, Winter Haven, FL 33881

      Single Family Home

      Listed by C BUDDY JOHNSON REALTY, LLC

      Stellar MLS
    • 3029 PINETREE, Winter Haven, FL 33884
      1/29 29
      New

      $ 340,000

      3 Beds3 Baths1,942 SqFt

      3029 PINETREE, Winter Haven, FL 33884

      Single Family Home

      Listed by SAFETYNET REALTY

      Stellar MLS
    • 429 AVENUE B NE #Apt A, Winter Haven, FL 33881
      1/19 19
      New

      $ 1,300

      2 Beds1 Bath875 SqFt

      429 AVENUE B NE #Apt A, Winter Haven, FL 33881

      Single Family Home

      Listed by STAR REALTY OF WINTER HAVEN

      Stellar MLS
    • 4662 OSPREY WAY, Winter Haven, FL 33881
      1/34 34
      New

      $ 330,000

      4 Beds2 Baths1,999 SqFt

      4662 OSPREY WAY, Winter Haven, FL 33881

      Single Family Home

      Listed by BROKERS REALTY OF CENTRAL FLOR

      Stellar MLS
    • 4928 KAIA AVE, Winter Haven, FL 33884
      1/26 26
      New

      $ 330,990

      5 Beds3 Baths2,447 SqFt

      4928 KAIA AVE, Winter Haven, FL 33884

      Single Family Home

      Listed by DR HORTON REALTY OF CENTRAL FLORIDA LLC

      Stellar MLS
    • 6027 GRAND OAKS DR SE, Winter Haven, FL 33884
      1/35 35
      New

      $ 157,500

      2 Beds2 Baths1,188 SqFt

      6027 GRAND OAKS DR SE, Winter Haven, FL 33884

      Manufactured Home

      Listed by BROKERS REALTY OF CENTRAL FLOR

      Stellar MLS
    • 70 POWELL RD, Winter Haven, FL 33880
      1/22 22
      New

      $ 1,895

      3 Beds2 Baths1,568 SqFt

      70 POWELL RD, Winter Haven, FL 33880

      Single Family Home

      Listed by PMI ARRICO REALTY AND PRTP MGT

      Stellar MLS
    • 991 GOTTHARD PASS DR, Winter Haven, FL 33881
      1/26 26
      New

      $ 1,950

      4 Beds2 Baths1,717 SqFt

      991 GOTTHARD PASS DR, Winter Haven, FL 33881

      Single Family Home

      Listed by AVANTI WAY REALTY LLC

      Stellar MLS
    • 104 MORNING GLORY CIR, Winter Haven, FL 33884
      1/39 39
      New

      $ 328,000

      3 Beds2 Baths1,806 SqFt

      104 MORNING GLORY CIR, Winter Haven, FL 33884

      Single Family Home

      Listed by COLDWELL BANKER REALTY

      Stellar MLS
    • 131 AVENUE B NE, Winter Haven, FL 33881
      1/7 7
      New

      $ 900

      1 Bed1 Bath610 SqFt

      131 AVENUE B NE, Winter Haven, FL 33881

      Condo

      Listed by LOCKHART & ASSOCIATES INC

      Stellar MLS
    • 1357 SALISBURY DR, Winter Haven, FL 33881
      1/32 32
      New

      $ 2,200

      5 Beds4 Baths2,344 SqFt

      1357 SALISBURY DR, Winter Haven, FL 33881

      Single Family Home

      Listed by OLYMPUS EXECUTIVE REALTY INC

      Stellar MLS
    • 2169 ROSE BLVD, Winter Haven, FL 33881
      1/25 25
      New

      $ 335,000

      4 Beds3 Baths2,121 SqFt

      2169 ROSE BLVD, Winter Haven, FL 33881

      Single Family Home

      Listed by XPERT REALTY GROUP

      Stellar MLS
    • 248 LAKE THOMAS DR, Winter Haven, FL 33880
      1/16 16
      New

      $ 315,000

      3 Beds2 Baths1,474 SqFt

      248 LAKE THOMAS DR, Winter Haven, FL 33880

      Single Family Home

      Listed by NHR BROKERAGE LLC

      Stellar MLS
    • 3135 LAUREL OAK LN, Winter Haven, FL 33884
      1/7 7
      Price Dropped by $10K

      $ 307,900

      4 Beds2 Baths1,754 SqFt

      3135 LAUREL OAK LN, Winter Haven, FL 33884

      Single Family Home

      Listed by CAMBRIDGE REALTY OF CENTRAL FL

      Stellar MLS
    • 3158 LAUREL OAK LN, Winter Haven, FL 33884
      1/4 4
      Pending

      $ 343,040

      4 Beds2 Baths2,005 SqFt

      3158 LAUREL OAK LN, Winter Haven, FL 33884

      Single Family Home

      Listed by CAMBRIDGE REALTY OF CENTRAL FL

      Stellar MLS
    • 1
    • 2
    • 3
    • 4
    • 5
    • ...
    • 50

    explore listings in Winter Haven

    • Open House
    • Price Reduced
    • Virtual Tour
    • 3D Tour
    Gailey Enterprises_Logo
    Gailey Enterprises Real Estate
    Rhonda Gailey
    1414 SW Martin Luther King JR Ave, Ocala, Florida, 34471, USA

    +1(352) 897-2018

    rhonda@gaileyenterprises.com

    Get My App

    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

    Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

    Gailey Enterprises_Logo
    Gailey Enterprises Real Estate
    Rhonda Gailey
    1414 SW Martin Luther King JR Ave, Ocala, Florida, 34471, USA

    +1(352) 897-2018

    rhonda@gaileyenterprises.com

    Get My App

    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

    Powered by Lofty Inc. Copyright 2025. All Rights Reserved.