Winding Cypress, FL Housing Market

Homes for sale

The Winding Cypress housing market is not very competitive. The median sale price of a home in Winding Cypress was $760K last month, down 1.9% since last year. The median sale price per square foot in Winding Cypress is $395, down 3.9% since last year.

Trends
Demand
Schools
Climate

Winding Cypress Housing Market Trends

What is the housing market like in Winding Cypress today?

$760K

Sale Price

-1.9%
since last year

$395

Sale $/Sq. Ft.

-3.9%
since last year

Under List Price

3.6%

Days on Market

68.5

Down Payment

—

Total Homes Sold

To compare other locations to the Winding Cypress and U.S. housing market, enter a city, neighborhood, state, or zip code into the search bar. Learn which home features in Winding Cypress add value to a home.

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How hot is the Winding Cypress housing market?

Winding Cypress is not very competitive. Homes sell in 68.5 days.

100

Not Very Competitive

Multiple offers are rare.
The average homes sell for about 4% below list price and go pending in around 69 days.
Hot homes
can sell for about 2% below list price and go pending in around 37 days.

Compare With Nearby Neighborhoods

Naples Reserve

100

Not Very Competitive

Multiple offers are rare.
The average homes sell for about 4% below list price and go pending in around 91 days.
Hot homes
can sell for about 1% below list price and go pending in around 43 days.

South Naples

100

Not Very Competitive

Multiple offers are rare.
The average homes sell for about 5% below list price and go pending in around 83 days.
Hot homes
can sell for about 2% below list price and go pending in around 28 days.

See more nearby cities and neighborhoods

View houses in Winding Cypress that sold recently

Recently sold homes

SOLD MAY 30, 2025
$675,000 Last Sold Price
2 beds
2 baths
1,554 sq ft
7742 Jacaranda Ln, Naples, FL 34114
List Price
$720,000
Sale to List
6% under list
Days on Market
77 days
7742 Jacaranda Ln, Naples, FL 34114
SOLD MAY 14, 2025
$925,000 Last Sold Price
3 beds
2 baths
2,118 sq ft
6854 Greenbriar Ct, Naples, FL 34114
List Price
$925,000
Sale to List
0% over list
Days on Market
68 days
6854 Greenbriar Ct, Naples, FL 34114
SOLD MAY 8, 2025
$760,000 Last Sold Price
2 beds
2 baths
1,921 sq ft
6758 Pennyroyal Dr, Naples, FL 34114
List Price
$799,000
Sale to List
5% under list
Days on Market
64 days
6758 Pennyroyal Dr, Naples, FL 34114
SOLD MAY 2, 2025
$860,000 Last Sold Price
3 beds
2 baths
2,208 sq ft
6763 Pennyroyal Dr, Naples, FL 34114
List Price
$899,000
Sale to List
4% under list
Days on Market
98 days
6763 Pennyroyal Dr, Naples, FL 34114
SOLD MAY 1, 2025
$537,000 Last Sold Price
2 beds
2 baths
1,554 sq ft
7591 Jacaranda Ln, Naples, FL 34114
List Price
$549,999
Sale to List
2% under list
Days on Market
61 days
7591 Jacaranda Ln, Naples, FL 34114
SOLD APR 17, 2025
$992,500 Last Sold Price
2 beds
2 baths
2,062 sq ft
7404 Winding Cypress Dr, Naples, FL 34114
List Price
$1,050,000
Sale to List
5% under list
Days on Market
159 days
7404 Winding Cypress Dr, Naples, FL 34114
SOLD APR 8, 2025
$635,000 Last Sold Price
2 beds
2 baths
1,554 sq ft
7199 Live Oak Dr, Naples, FL 34114
List Price
$659,000
Sale to List
4% under list
Days on Market
75 days
7199 Live Oak Dr, Naples, FL 34114
SOLD APR 1, 2025
$935,000 Last Sold Price
3 beds
2 baths
2,018 sq ft
7683 Winding Cypress Dr, Naples, FL 34114
List Price
$969,000
Sale to List
4% under list
Days on Market
166 days
7683 Winding Cypress Dr, Naples, FL 34114
See all recently sold homes in Winding Cypress.
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Schools in Winding Cypress

Learn about schools in the Winding Cypress area

Elementary
Middle
High

GreatSchools Rating

7/10

Manatee Elementary School

Public • PreK-5

584

Students

1 reviews

School data provided by GreatSchools. School service boundaries are intended to be used as reference only. To verify enrollment eligibility for a property, contact the school directly.

Climate's impact on Winding Cypress housing

Learn about natural hazards and environmental risks, such as floods, fires, wind, and heat that could impact homes in Winding Cypress.

Wind Factor - Extreme

100% of properties are at extreme risk of a severe wind event over the next 30 years

Heat Factor - Extreme

100% of properties are at extreme risk of heat over the next 30 years

Provided by First Street Foundation

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Winding Cypress, FL Housing Market

Winding Cypress Housing Market Trends

How hot is the Winding Cypress housing market?

View houses in Winding Cypress that sold recently

Recently sold homes

Schools in Winding Cypress

GreatSchools Rating

Climate's impact on Winding Cypress housing

Flood Factor - Major

Flood Factor

Fire Factor - Moderate

Fire Factor

Wind Factor - Extreme

Wind Factor

Wind likelihood over time

Heat Factor - Extreme

Heat Factor

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