Homes for sale in
Winter Haven, Florida
Chain of Lakes living in the heart of Central Florida
876
Homes for sale
$285,000
Median list price
$172
Avg price / sqft
42
Median days on market
Winter Haven sits in the middle of Polk County, a city built around its famous chain of connected lakes and an easygoing pace that draws boaters, retirees, and families alike. The waterfront homes along those lakes are a real draw, but so is the balance of small-city convenience and open water that makes daily life feel unhurried here.
For buyers, the market is approachable: with 876 active listings and a median list price of $285,000, Winter Haven runs well below Florida's coastal metros. There's genuine range too, from homes under $200K up to a handful of $1M-plus properties, and a steady supply of new construction if you want something turnkey. At a median 42 days on market, you have room to think without losing your leverage.
Winter Haven is in Polk County, Florida.
Within a 30-minute drive
Quick facts
$50,000 – $1.9M price range
1,653 sqft median home
$1,820/mo median rent
Balanced right now
Fresh on the market
Newest homes in Winter Haven
View all 876 homes →
$204,000$209,000
608 PATRICK AVENUE, WINTER HAVEN
2 bd · 1 ba · 980 sqft
$369,900
220 HARTRIDGE HILLS DR, WINTER HAVEN
3 bd · 2.5 ba · 2,383 sqft
$260,000
307 STERLING DRIVE, WINTER HAVEN
3 bd · 2 ba · 1,444 sqft
$95,000
1100 MARTINIQUE DRIVE UNIT 117, WINTER HAVEN
1 bd · 1 ba · 1,078 sqft
$289,900
2128 BRETTON RIDGE BOULEVARD, WINTER HAVEN
4 bd · 2 ba · 1,560 sqft
$310,000
709 SARNER PASS WAY, WINTER HAVEN
4 bd · 2.5 ba · 3,016 sqft
$299,000
1104 TYLER LOOP, WINTER HAVEN
3 bd · 2 ba · 1,540 sqft
$320,000
3365 COSTELLO CIRCLE, WINTER HAVEN
5 bd · 3 ba · 2,522 sqft
$220,000
719 AVENUE Q SE, WINTER HAVEN
2 bd · 2 ba · 1,181 sqft
$215,000
1328 3RD STREET NE, WINTER HAVEN
3 bd · 2 ba · 1,118 sqft
$325,000
2849 CATHY BOULEVARD, WINTER HAVEN
4 bd · 2 ba · 1,928 sqft
$110,000
333 LAKE HOWARD DR NW UNIT 102D, WINTER HAVEN
2 bd · 2 ba · 1,030 sqft
250 of 876 active listings shown
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Property features
The numbers that matter
The Winter Haven market
Balanced
6.5 months of inventory
Supply and demand are roughly even — negotiation cuts both ways.
1,841
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
▲ 2.7% yr/yr
Homes on the market
▼ 2.6% 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 Chain of Lakes
With 62 active waterfront listings, direct-access lake living is a realistic option, not a rare exception.
Room for every budget
List prices span $50,000 to $1,895,000, with a median of $285,000 that keeps most of the city within reach.
Strong new-construction pipeline
141 of the active listings are new construction, giving buyers plenty of move-in-ready and modern-layout choices.
Deep 55+ options
144 active 55-plus listings make Winter Haven a practical landing spot for retirees and downsizers.
Gated and pool homes aplenty
143 gated-community listings and 102 homes with a pool mean privacy and Florida backyard living are easy to find.
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.
On the calendar
Near Winter Haven
What it really costs
Owning here
Owning the median Winter Haven home
≈ $2,016/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
$1,820/mo
Median rent
206 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?+
Winter Haven pairs a walkable small-city feel with the recreation of its interconnected lakes, which is why it appeals to families, boaters, and retirees alike. Assigned schools include Winter Haven Senior High and Denison Middle, and the 55+ communities make it a common choice for downsizers. With 876 homes on the market, there's enough inventory to find the right fit.
Is Winter Haven expensive?+
Not by Florida standards — the median list price is $285,000 and the average price per square foot runs about $172. You'll find plenty at the lower end, with options in the under-$200K range, while only three current listings top $1 million.
What do homes cost in Winter Haven?+
The median list price is $285,000, spanning a wide range from $50,000 to $1,895,000, on a median home size of about 1,653 square feet. The market is mostly single-family homes — 674 of them — alongside 78 manufactured homes, 56 condos, and 30 townhouses. That mix keeps entry points varied depending on your budget.
How is the Winter Haven housing market right now?+
There are 876 active listings and the median time on market is 42 days, so buyers generally have time to compare rather than rush. If you want value, it's worth watching the just reduced listings and touring open houses this week to gauge how homes are priced.
What about HOA fees and property taxes?+
Costs here are modest: the median HOA runs about $58 per month and median property tax is around $2,951 per year. Fees vary by community, so expect higher dues in gated communities with shared amenities and lower or none in older neighborhoods.
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.
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