House Prices

Winding Cypress Naples, FL House Prices & Home Values 2026


Average Data

average house price$514,935
average size per house2088 ft²
average price per ft²232 $ / ft²

04/14/2026 - The value range (VR) for house prices in Winding Cypress Naples, FL is $220.4/ sqft to $243.6/ sqft. An average home with 2088 sqft costs approximately $431,203 to $476,593. Naples, FL includes 1 ZIP codes and it is located in Collier county. The lowest prices are found in ZIP 34114, while the highest are in ZIP 34114. The average price per sqare feet is $232. Our analysis is based on 15 property listings.

Avergage prices by ZIP codes Winding Cypress Naples

34114225 $ / ft²




Historical development of home values in Winding Cypress Naples

Year Estimated value (USD) Change vs. 2025
2010 $239,145 -53.6%
2011 $229,897 -55.4%
2012 $229,278 -55.5%
2013 $237,848 -53.8%
2014 $249,675 -51.5%
2015 $262,489 -49.0%
2016 $276,188 -46.4%
2017 $291,095 -43.5%
2018 $307,188 -40.3%
2019 $321,432 -37.6%
2020 $338,048 -34.4%
2021 $384,494 -25.3%
2022 $448,233 -13.0%
2023 $472,683 -8.2%
2024 $500,028 -2.9%
2025 $514,935 0.0%

Graph: estimated home values in Winding Cypress Naples over time (USD)



Example: 100% financing house in Winding Cypress Naples

Loan amount: $514,935

Interest rate: 5.62%

Fixed monthly payment: $2,963.28

Breakdown in the 1st month:
Interest portion: $2,412.47  –  Principal portion: $550.81

Yearly breakdown (100% financing)

Year Interest per year ($) Principal per year ($) Remaining balance at year-end ($)
1 $28,776.64 $6,782.73 $508,152.27
2 $28,385.34 $7,174.04 $500,978.23
3 $27,971.45 $7,587.92 $493,390.31
4 $27,533.70 $8,025.68 $485,364.64
5 $27,070.68 $8,488.69 $476,875.95
6 $26,580.96 $8,978.42 $467,897.53
7 $26,062.98 $9,496.39 $458,401.14
8 $25,515.12 $10,044.25 $448,356.88
9 $24,935.65 $10,623.72 $437,733.16
10 $24,322.75 $11,236.62 $426,496.54
11 $23,674.49 $11,884.88 $414,611.66
12 $22,988.84 $12,570.54 $402,041.12
13 $22,263.62 $13,295.75 $388,745.37
14 $21,496.57 $14,062.80 $374,682.57
15 $20,685.27 $14,874.11 $359,808.47
16 $19,827.16 $15,732.22 $344,076.25
17 $18,919.54 $16,639.83 $327,436.42
18 $17,959.56 $17,599.81 $309,836.61
19 $16,944.21 $18,615.17 $291,221.45
20 $15,870.27 $19,689.10 $271,532.34
21 $14,734.37 $20,825.00 $250,707.34
22 $13,532.95 $22,026.42 $228,680.92
23 $12,262.21 $23,297.16 $205,383.76
24 $10,918.16 $24,641.21 $180,742.55
25 $9,496.57 $26,062.80 $154,679.75
26 $7,992.97 $27,566.40 $127,113.35
27 $6,402.62 $29,156.75 $97,956.60
28 $4,720.53 $30,838.85 $67,117.75
29 $2,941.39 $32,617.99 $34,499.77
30 $1,059.61 $34,499.77 $0.00

Note: The calculation is based on a standard annuity mortgage with a fixed monthly payment over the entire term. Extra payments, interest rate changes, and additional purchase costs (e.g. taxes, notary fees) are not included.


How to sell in Winding Cypress Naples, FL


1500 sqft3900 sqft
Ø selling price$394,552$839,320
Ø fast selling$358,684$755,388
Ø high price sale$430,421$923,252

In 2026, houses in Winding Cypress Naples, FL will be offered at an average price of $232 per square foot. A 1,500 sqft home priced at $394,552 is 21.55% more expensive per square foot than a 3,900 sqft home priced at $839,320. Home prices in Winding Cypress Naples, FL vary significantly depending on the property’s condition and exact location. For a quick sale, a 2,700 sqft home should be listed at around $581,068. Sellers who can wait longer may achieve a higher price of up to $710,194.


Winding Cypress in Naples, FL

Discover Winding Cypress, a gated community in Naples, FL known for its nature-rich setting and resort-inspired lifestyle.
Set amid preserves and lakes, the neighborhood offers a quiet South Naples address with quick access to beaches, dining, and everyday conveniences.

Amenities & Lifestyle

Residents enjoy a modern clubhouse, a resort-style pool, fitness options, and active social programming that make daily life feel like vacation.
Outdoor lovers appreciate walking paths, bike-friendly streets, and plentiful green space that showcase Southwest Florida?s natural beauty.
Courts for popular sports, community events, and pet-friendly features help foster a welcoming, connected atmosphere.

Location & Real Estate

Real estate in Winding Cypress Naples ranges from stylish single-family homes to low-maintenance villas, appealing to a variety of lifestyles.
Thoughtful floor plans, open living areas, and covered lanais support indoor-outdoor living that is ideal for the Florida climate.
The community?s convenient location near major corridors simplifies commuting to downtown Naples, Marco Island, and top Gulf Coast attractions.

Why Buyers Choose Winding Cypress

Homebuyers value the blend of newer construction, strong amenities, and natural surroundings that enhance long-term enjoyment and potential resale.
If you?re considering homes for sale in Winding Cypress, this sought-after Naples neighborhood delivers comfort, convenience, and a vibrant Southwest Florida lifestyle.



FAQ – Home Values in Winding Cypress Naples

What is the median home value in Winding Cypress Naples in 2026?

In 2026, the typical home value in Winding Cypress Naples is about $514,935 for an average home size of 2088 square feet. This corresponds to an average price of roughly $232 per square foot.

What is the average cost per square foot in Winding Cypress Naples?

In 2026, homes in Winding Cypress Naples sell for an average of around $232 per square foot, with a typical range between $220.4 and $243.6 per square foot, depending on the property’s location, condition, and lot size.

What is the average home size in Winding Cypress?

The average home size in Winding Cypress Naples is about 2088 square feet, with an estimated 2026 value around $514,935.



Neighborhoods close to Winding Cypress Naples, FL

Calusa Island Village Goodland, FL309 $ / ft²
Arlington Park Sarasota, FL434 $ / ft²
South Venice Venice, FL178 $ / ft²
Gator Circle Cape Coral, FL140 $ / ft²
ChampionsGate Davenport, FL129 $ / ft²
Bay Crest Park Tampa, FL198 $ / ft²
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