Theresa Bocka
William Raveis Real Estate
(239) 363-6919
53 Total Sales
45 in Winding Cypress
$460K - $1.6M Price Range
Estimated Value: $1,031,649 - $1,100,000
Introducing a luxury estate with landscaped privacy corner lot home in Winding Cypress with pool and spa. Step into elegance with this stunning Pinnacle model estate home, set in the prestigious, gated community of Winding Cypress. This home stands out with its soaring raised tray ceilings, rare privacy and spacious yard, impact glass for peace of mind, and an expansive open layout filled with natural light and outstanding upgrades. Designed for those who love to entertain, the chef-inspired gourmet kitchen features top-tier finishes, premium appliances, and a spacious expanded island, the ideal gathering space for family and friends. With three bedrooms, three baths, a versatile den and an upgraded oversized three-car garage, this home offers flexibility and space to suit your lifestyle. Outside, a private backyard oasis awaits, complete with lush landscaping, a serene water view and a sprawling grassy yard, a rare find in this community. Take a refreshing dip in your sparkling pool and spa, designed for ultimate relaxation in a peaceful setting. Beyond your doorstep, Winding Cypress offers resort-style living like no other. The nearly 18,000-square-foot clubhouse boasts a zero-entry infinity pool with a lap section, a poolside restaurant, beach cabanas and even a sandy beach. Stay active with numerous pickleball courts, clay tennis courts, bocce, an outdoor yoga movement studio, and a vibrant community hall managed by a full-time activity director. Winding Cypress is a resort gated community at the midpoint between Marco Island and downtown Naples, and this home delivers the ultimate combination of luxury, convenience and an unmatched lifestyle. Don’t miss your chance to own one of the desirable and private estate homes in Winding Cypress of Naples.
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Theresa Bocka
William Raveis Real Estate
(239) 363-6919
53 Total Sales
45 in Winding Cypress
$460K - $1.6M Price Range
Ryan Nordyke
John R Wood Properties
(239) 350-4985
48 Total Sales
2 in Winding Cypress
$992,500 Price Range
MaryBeth Baron
Achieve Realty LLC
(216) 306-5682
23 Total Sales
4 in Winding Cypress
$850K - $875K Price Range
ML Meade
Premier Sotheby's Int'l Realty
(239) 977-8398
359 Total Sales
3 in Winding Cypress
$679K - $739K Price Range
Vito A Galatro
Premier Sotheby's Int'l Realty
(239) 307-0455
48 Total Sales
1 in Winding Cypress
$1,100,000 Price
Steven Purcell
Re/Max Alliance Group
(239) 351-1178
69 Total Sales
7 in Winding Cypress
$1.2M - $1.7M Price Range
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Buyer | Sale Price | Title Company |
|---|---|---|---|
| $1,100,000 | None Listed On Document | ||
| -- | Accommodation | ||
| $580,315 | Pgp Title Of Florida Inc |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Borrower | Loan Amount |
|---|---|---|---|
| Previous Owner | $915,000 | ||
| Previous Owner | $298,687 |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 03/03/2026 03/03/26 | Sold | $1,100,000 | -5.2% | $441 / Sq Ft |
| 02/04/2026 02/04/26 | Pending | -- | -- | -- |
| 11/21/2025 11/21/25 | Price Changed | $1,160,000 | -2.1% | $465 / Sq Ft |
| 10/23/2025 10/23/25 | Price Changed | $1,185,000 | -0.4% | $475 / Sq Ft |
| 09/15/2025 09/15/25 | Price Changed | $1,190,000 | -0.4% | $477 / Sq Ft |
| 07/25/2025 07/25/25 | Price Changed | $1,195,000 | -0.3% | $479 / Sq Ft |
| 06/19/2025 06/19/25 | Price Changed | $1,199,000 | -4.0% | $480 / Sq Ft |
| 05/22/2025 05/22/25 | Price Changed | $1,249,000 | -3.8% | $500 / Sq Ft |
| 04/14/2025 04/14/25 | For Sale | $1,299,000 | -- | $520 / Sq Ft |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $5,476 | $360,070 | ||
| 2024 | $5,199 | $349,922 | ||
| 2023 | $5,199 | $339,730 | $0 | $0 |
| 2022 | $4,702 | $329,835 | $0 | $0 |
| 2021 | $4,726 | $320,228 | $0 | $0 |
| 2020 | $4,645 | $315,807 | $0 | $0 |
| 2019 | $4,583 | $308,707 | $0 | $0 |
| 2018 | $6,863 | $478,632 | $98,582 | $380,050 |
| 2017 | $2,696 | $129,878 | $129,878 | $0 |
| 2016 | $1,507 | $26,000 | $0 | $0 |
Seller's Agent in 2026
Taylor Smith
Premier Sotheby's Int'l Realty
(239) 450-8625
32 in this area
57 Total Sales
Buyer's Agent in 2026
Theresa Bocka
William Raveis Real Estate
(239) 351-4955
23 in this area
53 Total Sales
Source: Naples Area Board of REALTORS®
MLS Number: 225038123
APN: 82679010821
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