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

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 search Advertise Sign In

Saved homes Saved searches Your tours Your inquiries Recently viewed Account settings

Rentals
Commercial

55 listings

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 beds New construction With a pool

5 Bedroom Homes in Winter Haven, FL

Hide Map

24 of 55 Listings

Map

24 of 55 Listings

Price Reduced26

5 Bedroom Homes in Winter Haven, FL — Page 2

55 listings

5 Bedroom Homes in Winter Haven, FL

Hide Map

24 of 55 Listings

Map

5 Bedroom Homes in Winter Haven, FL

24 of 55 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced26

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$346,000

5 bd · 4 ba · 3,756 sqft

5604 Royal Hills Dr, Winter Haven, FL

Jeff Jones · MARK SPAIN REAL ESTATE

22Active

$350,000

5 bd · 3 ba · 2,254 sqft

1187 Tyler Loop, Winter Haven, FL

Othner St. Fleurose · OSF REAL ESTATE SERVICE

32Active

$379,900

5 bd · 3 ba · 2,696 sqft

204 Inman Blvd, Winter Haven, FL

Veronica Bard · LA ROSA REALTY PRESTIGE

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced29Active

$300,000

5 bd · 3 ba · 2,577 sqft

6022 Grey Heron Dr, Winter Haven, FL

Xiomara Pichardo · LPT REALTY, LLC

16Active

$380,000

5 bd · 3 ba · 2,696 sqft

210 Meadowbrook Blvd, Winter Haven, FL

Lancey Lewis · HOMELIFE REALTY COASTAL PROPERTIES LLC

Price Reduced22Active

$354,900

5 bd · 3 ba · 2,523 sqft

1404 Axel Cir, Winter Haven, FL

Carlos DeJesus · EXIT REALTY 4CORNERS

80Active

$765,000

5 bd · 4 ba · 3,812 sqft

328 Hamilton Shores Dr NE, Winter Haven, FL

Michael Stone · THE STONES REAL ESTATE FIRM

Price Reduced35Active

$334,900

5 bd · 3 ba · 2,696 sqft

321 Alexzander Way, Winter Haven, FL

Joshua Nogowski · TAH FLORIDA LLC

32Active

$320,000

5 bd · 3 ba · 2,254 sqft

1454 Austin St, Winter Haven, FL

Carla Moreno Pineda · DALTON WADE INC

Price Reduced66Active

$405,000

5 bd · 2 ba · 2,992 sqft

199 8th St SE, Winter Haven, FL

Jenn Gibbs · SKYBROOK REALTY & ASSOCIATES, INC.

9Active

$200,000

5 bd · 2 ba · 1,700 sqft

1605 36th St NW, Winter Haven, FL

Martineau Dimanche · INTELLIGENCE CHOICE REALTY LLC

52Active

$589,500

5 bd · 5 ba · 2,626 sqft

1302 Lake Elbert Dr SE, Winter Haven, FL

Russ Yerton · ELEVATE REAL ESTATE BROKERS

Price Reduced57Active

$519,990

5 bd · 3 ba · 2,653 sqft

445 Talamone Dr, Winter Haven, FL

Jimmy Aguilar · 3D TEAM REALTY LLC

Price Reduced58Active

$419,000

5 bd · 3 ba · 2,577 sqft

3097 Buckeye Pointe Dr, Winter Haven, FL

Desiree Carlson · RE/MAX HERITAGE PROFESSIONALS

Price Reduced25Active

$370,900

5 bd · 3 ba · 2,336 sqft

1774 White Elephant Loop, Winter Haven, FL

Kennia Lozada Rivera · LA ROSA REALTY CW PROPERTIES L

67Active

$1,195,000

5 bd · 6 ba · 3,235 sqft

250 Brigham Rd NW, Winter Haven, FL

David Small · KELLER WILLIAMS REALTY SMART 1

Price Reduced26Active

$394,999

5 bd · 4 ba · 3,030 sqft

5118 Kinsley Dr, Winter Haven, FL

Stephanie Morales, LLC · AXEN REALTY, LLC

Price Reduced26Active

$394,999

5 bd · 4 ba · 3,030 sqft

5110 Kinsley Dr, Winter Haven, FL

Stephanie Morales, LLC · AXEN REALTY, LLC

Price Reduced62Active

$285,000

5 bd · 3 ba · 2,522 sqft

3365 Costello Cir, Winter Haven, FL

Emily Lietz · ENGEL & VOELKERS LAKELAND

Price ReducedOpen house Sun, Oct 25 · 1:00 PM33Active

$724,999

5 bd · 5 ba · 3,703 sqft

2656 Wyndsor Oaks Way, Winter Haven, FL

Jonathan Minerick · HOMECOIN.COM

Price Reduced31Active

$364,900

5 bd · 3 ba · 2,244 sqft

1783 White Elephant Loop, Winter Haven, FL

Gayle Van Wagenen · LGI REALTY- FLORIDA, LLC

Price Reduced37Active

$375,000

5 bd · 3 ba · 2,696 sqft

1328 Daisy Field Dr, Winter Haven, FL

David Small · KELLER WILLIAMS REALTY SMART 1

Price Reduced15Active

$299,000

5 bd · 2 ba · 4,053 sqft

1450 W Lake Cannon Dr NW, Winter Haven, FL

Veronica Davis · EXP REALTY LLC

Price Reduced69Active

$367,000

5 bd · 4 ba · 3,200 sqft

1015 Corso Dr, Winter Haven, FL

William Figueroa · SOVEREIGN REAL ESTATE GROUP

1 2 3

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 housing market

September 2026 · This period is still settling

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 30, 2026

Median sale price: $270,000$195,000–$332,030 typical range
Price per sq. ft.: $159
Sales: 200
Paid in cash: 38.0%

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.

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

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
Foreclosures & Short Sales
55+ Community Homes

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

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.

Your local brokerage

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

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 30, 2026

Median sale price: $270,000$195,000–$332,030 typical range
Price per sq. ft.: $159
Sales: 200
Paid in cash: 38.0%

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.