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Waterfront Homes in Winter Haven, FL
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3 bedsNew constructionWith a pool

Waterfront Homes in Winter Haven, FL

Waterfront Homes in Winter Haven, FL

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24 of 55 Listings
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Waterfront Homes in Winter Haven, FL

24 of 55 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 1921 Manor Cir SE — photo87Active

    $1,295,000

    3 bd · 3 ba · 2,375 sqft

    1921 Manor Cir SE, Winter Haven, FL

    Dee Norris · NEXTHOME NORRIS & COMPANY REAL

  2. 1400 Avenue D NE — photo76Active

    $337,500

    3 bd · 2 ba · 2,034 sqft

    1400 Avenue D NE, Winter Haven, FL

    Glenda Pruitt · FLORIDA HOME CHOICE REALTY

  3. 1020 W Lake Hamilton Dr — photoOpen house Sun, Oct 18 · 1:00 PM56Active

    $710,000

    4 bd · 3 ba · 3,428 sqft

    1020 W Lake Hamilton Dr, Winter Haven, FL

    Tony Insua, Jr · LOCKHART & ASSOCIATES INC

  4. 1097 Carefree Cove Dr — photoOpen house Sat, Oct 17 · 11:00 AM50Active

    $319,900

    3 bd · 2 ba · 1,484 sqft

    1097 Carefree Cove Dr, Winter Haven, FL

    Frankie Eizere · RE/MAX HERITAGE PROFESSIONALS

  5. 10 W Lake Hamilton Cir — photo36Active

    $485,000

    4 bd · 2 ba · 2,400 sqft

    10 W Lake Hamilton Cir, Winter Haven, FL

    John Keller, III · JACK KELLER INC

  6. 13 Bogey Dr — photo61Active

    $1,750,000

    4 bd · 4 ba · 3,476 sqft

    13 Bogey Dr, Winter Haven, FL

    Cathy Kluytenaar · THE K TEAM REAL ESTATE SERVICES LLC

  7. 4028 Phoenician Way — photo67Active

    $330,000

    2 bd · 2 ba · 1,784 sqft

    4028 Phoenician Way, Winter Haven, FL

    Lori Raath · LAKE ASHTON REALTY INC.

  8. 1475 Grand Cayman Cir — photo59Active

    $359,000

    3 bd · 2 ba · 2,066 sqft

    1475 Grand Cayman Cir, Winter Haven, FL

    Tina Heim, PA · KELLER WILLIAMS REALTY

  9. 900 Lake Martha Dr NE — photoPrice Reduced48Active

    $440,000

    4 bd · 4 ba · 3,408 sqft

    900 Lake Martha Dr NE, Winter Haven, FL

    Sam Daniels · KELLER WILLIAMS REALTY SMART 1

  10. 742 Santa Maria Dr — photoPrice Reduced59Active

    $399,900

    3 bd · 3 ba · 2,592 sqft

    742 Santa Maria Dr, Winter Haven, FL

    Rick Hemenway · CROSBY & ASSOCIATES, INC.

  11. 2215 Starboard Dr #29 — photo27Active

    $184,900

    2 bd · 2 ba · 1,436 sqft

    2215 Starboard Dr #29, Winter Haven, FL

    Scott Kline · KLINE REAL ESTATE SERVICES

  12. 333 Lake Howard Dr NW #302B — photoPrice Reduced12Active

    $99,000

    2 bd · 2 ba · 1,030 sqft

    333 Lake Howard Dr NW #302B, Winter Haven, FL

    Karen Myers · UNITED REALTY GROUP INC

  13. 2510 Cypress Gardens Blvd — photo93Active

    $865,000

    5 bd · 3 ba · 3,482 sqft

    2510 Cypress Gardens Blvd, Winter Haven, FL

    Steven Koleno · BEYCOME OF FLORIDA LLC

  14. 1016 S Lake Mariam Dr — photoPrice Reduced92Active

    $750,000

    5 bd · 4 ba · 3,694 sqft

    1016 S Lake Mariam Dr, Winter Haven, FL

    Kelly Jones · KELLER WILLIAMS REALTY SMART 1

  15. 25 Lakewood Cswy — photo52Active

    $849,900

    5 bd · 4 ba · 4,108 sqft

    25 Lakewood Cswy, Winter Haven, FL

    Melissa Meyer · KEENE'S POINTE REALTY

  16. 3640 Crump Rd — photo63Active

    $1,399,900

    4 bd · 3 ba · 3,309 sqft

    3640 Crump Rd, Winter Haven, FL

    Amy Reynolds · LOCKHART & ASSOCIATES INC

  17. 694 Lake Otis Dr SE — photo30Active

    $949,000

    4 bd · 3 ba · 3,483 sqft

    694 Lake Otis Dr SE, Winter Haven, FL

    Steve Lockhart · LOCKHART & ASSOCIATES INC

  18. 1019 W Lake Eloise Ter — photoPrice Reduced56Active

    $880,000

    2 bd · 3 ba · 2,768 sqft

    1019 W Lake Eloise Ter, Winter Haven, FL

    Ashley Adams · HOGAN & ASSOCIATES REAL ESTATE FIRM

  19. 228 W Lake Ina Dr — photoPrice Reduced64Active

    $389,000

    3 bd · 4 ba · 1,675 sqft

    228 W Lake Ina Dr, Winter Haven, FL

    Casandra Vann · KELLER WILLIAMS REALTY

  20. 4040 Palma Ceia Cir — photo100Active

    $749,000

    3 bd · 4 ba · 2,493 sqft

    4040 Palma Ceia Cir, Winter Haven, FL

    Deanna Stone · THE STONES REAL ESTATE FIRM

  21. 4123 Island Lakes Dr — photoOpen house Sun, Oct 18 · 12:00 PM48Active

    $470,000

    4 bd · 2 ba · 1,990 sqft

    4123 Island Lakes Dr, Winter Haven, FL

    Michelle Howard · KELLER WILLIAMS REALTY SMART 1

  22. 1103 Cypress Gardens Blvd #13 — photo14Active

    $124,800

    1 bd · 1 ba · 475 sqft

    1103 Cypress Gardens Blvd #13, Winter Haven, FL

    Linda Andre · COLDWELL BANKER REALTY

  23. 2820 Traditions Blvd S — photo44Active

    $309,900

    3 bd · 2 ba · 1,823 sqft

    2820 Traditions Blvd S, Winter Haven, FL

    Stephanie Bombinski · AGENT GROUP REALTY

  24. 2004 Leisure Dr — photoPrice Reduced44Active

    $675,000

    4 bd · 3 ba · 2,312 sqft

    2004 Leisure Dr, Winter Haven, FL

    Ralph Harvey · LISTWITHFREEDOM.COM

123

About Waterfront Homes in Winter Haven, FL

Waterfront Homes in Winter Haven, FL: 55 active listings as of October 17, 2026, 06:12 UTC.

Property types among these 55 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 Residence4276.4%
Condominium916.4%

Explore Winter Haven homes

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Listing data & MLS disclosures

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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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    Thomas O'Leary

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    Winter Haven, FL community profile

    Population
    58,351
    Median income
    $56,564
    Housing units
    26,800
    People per sq. mi.
    605.3
    Area
    96.4 sq. mi.

    Source: HJN community data

    Winter Haven housing market

    September 2026 · This period is still settling

    Winter Haven 12-month median sale price trend

    Selling at 99.9% of asking price

    Sales here are closing essentially at asking. MLS · 138 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 28, 2026

    Median sale price
    $270,000$196,000–$334,500 typical range
    Price per sq. ft.
    $160
    Sales
    175
    Paid in cash
    37.7%

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

    Median list price
    $294,400
    Homes for sale
    762
    Median days on market
    42 days

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

    Year-over-year
    -18.2%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

    Median home size
    1,632 sq. ft.