Neighborhood · Winter Haven, Florida
Cypress Landing
Right-sized homes in the heart of Polk County
2
Homes for sale
$292,450
Median list price
$161
Avg price / sqft
54
Median days on market
Cypress Landing is a settled residential pocket of Winter Haven, the kind of place where mid-sized homes on comfortable lots make sense for families and first-time buyers alike. It sits within reach of established neighborhoods like Orchid Springs and Eloise Woods, and feeds into Garden Grove Elementary School and Winter Haven Senior High School. Central Florida's theme parks and airports are all inside a comfortable drive, so weekend trips and commutes both stay manageable.
For buyers today, this is a small and tightly held market — only two homes are active right now, with a median list price of $292,450. Over the past year 12 homes sold at a median of $243,500, and sellers are averaging 99% of asking, so pricing is realistic on both sides. With homes typically taking around six weeks to sell, you have room to make a considered decision rather than a rushed one.
Cypress Landing is a community in Winter Haven, Florida.
Quick facts
$289,900 – $295K price range
1,833 sqft median home
$83/mo median HOA
12 sold in 12 months
Drive times
On the market now
Homes for sale in Cypress Landing
$289,900
3971 CYPRESS LANDING W, WINTER HAVEN
3 bd · 2 ba · 1,674 sqft
$295,000
4114 FISHERMANS LANDING, WINTER HAVEN
3 bd · 2 ba · 1,992 sqft
Every active listing inside the Cypress Landing boundary
Open full map search →The numbers that matter
The Cypress Landing market
12
Sold, last 12 months
$243,500
Median sold price
99%
Sale-to-list ratio
What sellers actually get vs asking
60 days
Median time to sell
Cypress Landing vs Winter Haven
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 6.0% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Cypress Landing boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Cypress Landing is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Cypress Landing home
≈ $2,054/mo
$292,450 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$83/mo
Median HOA
From current listings inside the boundary
Population
704
Median age
41
Median income
$62,000
Median home value
$239,500
Beyond the listings
Living in Cypress Landing
Appearance oriented
Top 8% in the U.S.Body Art
Who says the body isn't a canvas? This population loves talking about tattoos, body art and piercings.
Active
Top 9% in the U.S.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.
Food & Drink
Top 10% in the U.S.Sweet Treats
This population has a sweet tooth, and they're looking for treats to satisfy their sugar craving, including candy, cupcakes and flavorful toppings.
Appearance oriented
Top 19% in the U.S.Trend Trackers
This population lives as fast as the culture. They like to keep up with the latest trends, especially when it comes to apparel and accessories.
Pieces of History
You can find these people researching an upcoming exhibit at the natural history museum or learning about a famous monument. This population enjoys learning about the past.
Active
Top 21% in the U.S.Functional Fitness
Looking good and reaching fitness goals is all about discipline: Eat right. Work hard. No excuses. This population is more likely to view working out as a means to an end.
People who close here
Our Winter Haven experts
Straight answers
Cypress Landing FAQs
Is Cypress Landing a good place to live?+
It's a quiet residential neighborhood in Winter Haven with practical homes and easy access to established communities like Traditions and Orchid Springs. Assigned schools include Garden Grove Elementary, Denison Middle, and Winter Haven Senior High, and the central Polk County location keeps both the theme parks and airports within about an hour's drive.
Is Cypress Landing expensive?+
It sits in a moderate range for the area, with a median list price of $292,450 and homes selling at a median of $243,500 over the past year. At roughly $161 per square foot, it's an accessible entry point compared with much of Central Florida.
What do homes cost in Cypress Landing?+
Right now the two active listings fall between $289,900 and $295,000, with a median of $292,450. The typical home is about 1,833 square feet, and you can see current options on the live map.
How is the market here?+
It's a small, steady market — 12 homes sold in the last 12 months with sellers averaging 99% of their asking price. Homes take a median of about 42 days to sell, so buyers have time to evaluate without the pressure of a frenzied pace.
What about HOA fees and property taxes?+
The median HOA runs about $83 per month, which is modest for a neighborhood of this type. Property taxes come in around $2,639 a year, keeping overall carrying costs reasonable.
Keep exploring
More Winter Haven neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. 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.
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