Homes for sale in
Winter Haven, Florida
Chain of Lakes living in the heart of Central Florida
772
Homes for sale
$285,000
Median list price
$172
Avg price / sqft
48
Median days on market
Winter Haven built its identity around water — a famous chain of interconnected lakes that shapes how people spend weekends here, from boating to fishing to lakeside dinners. It's a genuine Polk County town with an easygoing pace, yet you're roughly 46 minutes from Walt Disney World and under an hour from both downtown Tampa and downtown Orlando, which makes it a practical base for commuters and families alike.
For buyers, the market is refreshingly reachable: the median list price sits at $285,000 and 823 homes are active right now, spanning everything from starter properties to the occasional $1M+ listing. There's real range here — from waterfront homes on the lakes to a deep bench of new construction, plus plenty of single-family homes in the middle. With homes taking a median 48 days to sell and sellers getting 97% of asking, it's a market where patient buyers have room to negotiate.
Winter Haven is in Polk County, Florida.
Quick facts
$57,900 – $1.8M price range
1,673 sqft median home
$1,845/mo median rent
Leans seller right now
Drive times
Fresh on the market
Newest homes in Winter Haven
View all 772 homes →
$54,900
213 LAKESIDE RANCH CIRCLE, WINTER HAVEN
2 bd · 1 ba · 672 sqft
$335,000
121 LOWELL ROAD, WINTER HAVEN
3 bd · 2 ba · 1,980 sqft
$95,000
1100 MARTINIQUE DRIVE UNIT 117, WINTER HAVEN
1 bd · 1 ba · 1,078 sqft
$515,000
230 BROAD STREET, WINTER HAVEN
4 bd · 3 ba · 3,024 sqft
$250,000
146 8TH STREET, WINTER HAVEN
3 bd · 2 ba · 1,404 sqft
$115,000
4332 CHERRYWOOD STREET, WINTER HAVEN
2 bd · 2 ba · 1,150 sqft
$335,900$351,370
2820 SAN MARCO WAY E, WINTER HAVEN
4 bd · 3.5 ba · 2,227 sqft
$299,000
1104 TYLER LOOP, WINTER HAVEN
3 bd · 2 ba · 1,540 sqft
$289,900
2128 BRETTON RIDGE BOULEVARD, WINTER HAVEN
4 bd · 2 ba · 1,560 sqft
$260,000
307 STERLING DRIVE, WINTER HAVEN
3 bd · 2 ba · 1,444 sqft
$390,000
437 BROWARD TERRACE, WINTER HAVEN
4 bd · 2 ba · 1,687 sqft
$320,480
576 ITUNA CIRCLE, WINTER HAVEN
3 bd · 2 ba · 1,545 sqft
250 of 772 active listings shown
Open full map search →Find your fit
Most popular Winter Haven searches
Popular searches
Property features
The numbers that matter
The Winter Haven market
Leans seller
4.8 months of inventory
Demand still outpaces supply, but buyers have a little more room.
1,850
Sold, last 12 months
$280,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
48 days
Median time to sell
Winter Haven vs Polk County
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 1.8% yr/yr
Homes on the market
▼ 1.4% yr/yr
Homes sold per month
Live Stellar MLS data — listings and closed sales in Winter Haven, FL. Rolling medians smooth single-month swings in thin markets.
Where to look
Winter Haven neighborhoods
Neighborhood boundaries by edgeAI — listings matched to the actual polygon, not agent-entered subdivision names.
For the school run
School zones with homes for sale
Homes matched to official attendance boundaries — always verify zoning with the district.
Beyond the listings
Living in Winter Haven
Life on the water
With 60 active waterfront listings and dozens more with lake views, boating and fishing are part of everyday life on the Chain of Lakes.
Priced for real buyers
A $285,000 median list price and listings starting under $60,000 make Winter Haven one of the more attainable Central Florida markets.
Strong new-construction pipeline
With 136 new-construction homes active, buyers who want modern layouts and warranties have plenty to choose from.
Central to the theme parks
Walt Disney World is about 46 minutes away and Universal Orlando roughly 56, so day trips don't require an overnight.
Room for 55+ buyers
126 active 55+ listings give downsizers and retirees a solid selection of age-restricted options.
Population
52,846
Median age
40.6
Median income
$59,604
Median home value
$248,200
What people here are into
Entertainment
Top 23% in the U.S.Party Life
The party don't stop until the sun comes up. Loud music, crowds, and shots are a recipe for a great night out for these people.
Relationships
Love & Romance
Love is in the air when this population is present. Includes people expressing their feelings for significant others in special ways. Common activities include anniversaries and date nights.
Active
Fitness Obsession
Passionate about strength training, this population relies heavily on the encouragement of the exercise community. While these people seek the latest fitness techniques, they're also interested in supplements and equipment.
Appearance oriented
All About Hair
Passionate about all things hair, this population is talking about hair tutorials or the hottest celebrity blowout.
Food & Drink
Fueling for Fitness
A population characterized by healthy eating. Often pre-planning for meals for the purpose of fitness and convenience. Likely to participate in meal prep trends.
Attitudes
Volunteering & Giving
Expressing a desire to give back and do good for the community, this behavior emphasizes charity. Common activities include volunteering, fundraisers, and donations.
What it really costs
Owning here
Owning the median Winter Haven home
≈ $2,010/mo
$285,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
5%
In a FEMA flood zone
Most homes here sit outside high-risk zones
$1,845/mo
Median rent
181 homes for rent right now
People who close here
Our Winter Haven experts
Straight answers
Winter Haven real estate FAQs
Is Winter Haven a good place to live?+
It's a water-oriented town organized around a chain of lakes, with commuter access to Tampa (about 57 minutes) and Orlando (about 62 minutes). Assigned schools include Winter Haven Senior High School and Chain of Lakes Elementary, and neighborhoods range from established areas like Inwood and Jan Phyl Village to newer communities like Villamar and Lucerne Park Reserve.
Is Winter Haven expensive?+
Not by Central Florida standards — the median list price is $285,000 and the average price per square foot is $173. Listings run from $57,900 up to $1,799,900, so you can browse by price and still find plenty under $200,000.
What do homes cost in Winter Haven?+
The median home is about 1,673 square feet, and over the past year 1,830 homes sold at a median price of $280,000. Single-family homes dominate the market with 649 active, but you'll also find condos, townhomes, and homes with a pool across a wide price range.
How is the Winter Haven market right now?+
There are 823 active listings and homes take a median 48 days to sell, so buyers have time to shop. Sellers are getting 97% of asking on average, which leaves modest room to negotiate — and it's worth watching the just reduced listings for the sharpest deals.
What about HOA fees and property taxes?+
The median HOA is a low $58 per month, and many single-family neighborhoods carry no HOA at all. Median annual property tax runs about $2,856, and if you want more amenities the gated communities and 55+ options may carry higher dues.
Keep exploring
Nearby areas
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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS. Market statistics are computed from listing and sold data and change as the market moves.
Never miss a listing
New Winter Haven homes, in your inbox
A daily digest of every new listing in Winter Haven — straight from the MLS, hours after it goes live. Unsubscribe anytime.