Realty.com
Buy

Start here

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

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
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
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Save search

Map layers

Safety

Safety & registry resources

Review official public-safety information for any area from these government sources:

  • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
  • FBI: state sex-offender registry directory
Realty.com
Buy

Start here

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

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Rentals
  • Commercial

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
Find an Agent
Save search
3 bedsNew constructionWith a pool
Open Houses in Winter Haven, FL
32 listings

Open Houses in Winter Haven, FL

Open Houses in Winter Haven, FL

Hide Map
24 of 32 Listings
Map

Open Houses in Winter Haven, FL

24 of 32 Listings

  1. 6216 Pinehurst Loop — photoOpen house Sat, Oct 10 · 10:00 AM68

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$429,000

3 bd · 2 ba · 2,045 sqft

6216 Pinehurst Loop, Winter Haven, FL

Lori Raath · LAKE ASHTON REALTY INC.

  • 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

  • 1331 Haines Dr — photoOpen house Sat, Oct 10 · 11:00 AM36Active

    $249,000

    3 bd · 2 ba · 1,471 sqft

    1331 Haines Dr, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  • 441 San Jose Dr — photoOpen house Sat, Oct 10 · 10:00 AM43Active

    $259,900

    2 bd · 2 ba · 1,843 sqft

    441 San Jose Dr, Winter Haven, FL

    Brian Cox · KELLER WILLIAMS REALTY SMART 1

  • 4302 Shadow Wood Ln — photoOpen house Sat, Oct 10 · 10:00 AM38Active

    $250,000

    2 bd · 2 ba · 1,507 sqft

    4302 Shadow Wood Ln, Winter Haven, FL

    Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

  • 6136 Pebble Beach Blvd — photoOpen house Sat, Oct 17 · 10:00 AM90Active

    $549,999

    3 bd · 3 ba · 2,682 sqft

    6136 Pebble Beach Blvd, Winter Haven, FL

    Lori Raath · LAKE ASHTON REALTY INC.

  • 1380 S Lake Roy Dr — photoPrice ReducedOpen house Sat, Oct 10 · 11:00 AM46Active

    $383,000

    4 bd · 3 ba · 2,468 sqft

    1380 S Lake Roy Dr, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  • 576 Ituna Cir — photoOpen house Sat, Oct 10 · 11:00 AM4Active

    $320,480

    3 bd · 2 ba · 1,545 sqft

    576 Ituna Cir, Winter Haven, FL

    George Lindsey, III · CAMBRIDGE REALTY OF CENTRAL FL

  • 5621 Forest Ridge Dr — photoPrice ReducedOpen house Sun, Oct 11 · 2:00 PM52Active

    $220,000

    3 bd · 2 ba · 1,256 sqft

    5621 Forest Ridge Dr, Winter Haven, FL

    Denise Spears · CENTURY 21 MYERS REALTY

  • 615 Avenue a NE — photoPrice ReducedOpen house Sat, Oct 10 · 2:00 PM39Active

    $260,000

    3 bd · 2 ba · 1,848 sqft

    615 Avenue a NE, Winter Haven, FL

    Chad Lindsey · LOKATION

  • 296 Meredith Blvd — photoPrice ReducedOpen house Sat, Oct 10 · 1:00 PM35Active

    $289,990

    4 bd · 2 ba · 1,625 sqft

    296 Meredith Blvd, Winter Haven, FL

    Nancy Pruitt, PA · OLYMPUS EXECUTIVE REALTY INC

  • 544 Ituna Cir — photoPrice ReducedOpen house Sun, Oct 11 · 2:00 PM4Active

    $336,900

    3 bd · 2 ba · 2,005 sqft

    544 Ituna Cir, Winter Haven, FL

    George Lindsey, III · CAMBRIDGE REALTY OF CENTRAL FL

  • 144 Waterside Cir — photoPrice ReducedOpen house Sat, Oct 10 · 1:00 PM37Active

    $299,000

    3 bd · 2 ba · 1,847 sqft

    144 Waterside Cir, Winter Haven, FL

    Ythamarie Rosario · KELLER WILLIAMS ADVANTAGE III

  • 297 Meadowbrook Blvd — photoPrice ReducedOpen house Sat, Oct 10 · 12:00 PM19Active

    $230,000

    3 bd · 2 ba · 1,426 sqft

    297 Meadowbrook Blvd, Winter Haven, FL

    Karina Alfonso · LPT REALTY, LLC

  • 1061 Sawgrass Dr — photoOpen house Sat, Oct 10 · 10:00 AM52Active

    $449,900

    3 bd · 2 ba · 2,069 sqft

    1061 Sawgrass Dr, Winter Haven, FL

    Barb Wiechmann · ROOST REALTY GROUP LLC

  • 937 Cattleman St — photoOpen house Sat, Oct 17 · 1:00 PM18Active

    $340,000

    4 bd · 2 ba · 1,828 sqft

    937 Cattleman St, Winter Haven, FL

    Isabelle Maye · BHHS FLORIDA PROPERTIES GROUP

  • 217 4th Jpv St — photoPrice ReducedOpen house Sat, Oct 10 · 2:00 PM20Active

    $214,000

    3 bd · 1 ba · 1,064 sqft

    217 4th Jpv St, Winter Haven, FL

    Tiffany Steck · BHHS FLORIDA PROPERTIES GROUP

  • 5118 Kinsley Dr — photoPrice ReducedOpen house Sat, Oct 10 · 11:00 AM26Active

    $389,999

    5 bd · 4 ba · 3,030 sqft

    5118 Kinsley Dr, Winter Haven, FL

    Stephanie Morales, LLC · AXEN REALTY, LLC

  • 5110 Kinsley Dr — photoPrice ReducedOpen house Sat, Oct 10 · 11:00 AM26Active

    $389,999

    5 bd · 4 ba · 3,030 sqft

    5110 Kinsley Dr, Winter Haven, FL

    Stephanie Morales, LLC · AXEN REALTY, LLC

  • 2121 River Hawk Loop — photoOpen house Sat, Oct 10 · 10:00 AM30Active

    $342,900

    3 bd · 2 ba · 1,741 sqft

    2121 River Hawk Loop, Winter Haven, FL

    Rodrigo Gomes De Almeida · KELLER WILLIAMS REALTY SMART 1

  • 2122 River Hawk Loop — photoOpen house Sat, Oct 10 · 10:00 AM46Active

    $344,900

    4 bd · 2 ba · 1,741 sqft

    2122 River Hawk Loop, Winter Haven, FL

    Rodrigo Gomes De Almeida · KELLER WILLIAMS REALTY SMART 1

  • 10 Enclave Dr — photoPrice ReducedOpen house Sun, Oct 11 · 2:00 PM33Active

    $214,900

    2 bd · 2 ba · 1,368 sqft

    10 Enclave Dr, Winter Haven, FL

    Erin Floyd · COLDWELL BANKER REALTY

  • 1100 Carefree Cove Dr — photoPrice ReducedOpen house Sat, Oct 10 · 9:00 AM13Active

    $200,000

    3 bd · 2 ba · 1,019 sqft

    1100 Carefree Cove Dr, Winter Haven, FL

    Karen Albright · OPENDOOR BROKERAGE LLC

  • 2108 River Hawk Loop — photoOpen house Sat, Oct 10 · 10:00 AM24Active

    $384,900

    4 bd · 2 ba · 2,032 sqft

    2108 River Hawk Loop, Winter Haven, FL

    Rodrigo Gomes De Almeida · KELLER WILLIAMS REALTY SMART 1

  • 12

    Explore Winter Haven homes

    By price

    • Homes Under $100K
    • Homes Under $200K
    • Homes Under $300K
    • Homes Under $400K

    By bedrooms

    • 2 Bedroom Homes
    • 3 Bedroom Homes
    • 4 Bedroom Homes
    • 5 Bedroom Homes

    By type

    • Single-Family Homes
    • Condos
    • Manufactured Homes

    By feature

    • New Construction Homes
    • Homes with a Pool
    • Waterfront Homes
    • Open Houses
    • Foreclosures & Short Sales
    • 55+ Community Homes
    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

    Equal Housing OpportunityEqual Housing Lender

    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 local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Listing data & MLS disclosures

    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 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 99.7% of asking price

    Sales here are closing essentially at asking. MLS · 137 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 18, 2026

    Median sale price
    $270,000$207,500–$329,495 typical range
    Price per sq. ft.
    $161
    Sales
    135
    Paid in cash
    36.3%

    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
    48 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.