MaryBeth Baron
Achieve Realty LLC
(216) 306-5682
24 Total Sales
4 in Winding Cypress
$850K - $875K Price Range
Discover effortless luxury in this lovely villa—your private oasis in a premier gated Naples community, Winding Cypress. This inviting 2-bedroom + den, 2-bath home delivers exceptional comfort and versatility with a bright, open layout designed for effortless living and entertaining. Step into the expansive Great Room with high ceilings, creating an open, airy vibe—perfect for gathering with friends or unwinding after a day out in Naples. The chef's kitchen impresses with premium quartz countertops, solid wood soft-close cabinets, and natural gas cooking. High-traffic porcelain tile flooring flows seamlessly throughout the entire villa, paired with smooth-finish walls for a clean, modern, low-maintenance aesthetic. The flexible den, enclosed by beautiful glass panel doors, adapts effortlessly as a home office or third bedroom. Both bedrooms feature generous walk-in closets, and the bathrooms showcase floor-to-ceiling porcelain tile, glass showers, and spa-like sophistication. The master bath elevates your routine with a dramatic full-wall custom mirror and elegant drop-down designer lighting. Outside, this premium lot offers generous spacing between villas and captivating views over the community's second-largest lake—where serene water vistas create an unparalleled sense of tranquility and timeless appeal. The west-facing orientation captures breathtaking sunsets reflecting off the shimmering waters, while the south-facing exposure floods the interior with natural light. Plenty of space awaits an extended lanai or private pool, all enhanced by the soothing backdrop of the lake. Built for peace of mind: impact windows and doors boost energy efficiency, reduce noise, and lower insurance premiums—no flood insurance required in FEMA Zone X. Appliances, A/C, and water heater have performed flawlessly since new. Fiber optic connectivity ensures ultra-fast internet and seamless 4K streaming. Natural gas powers cooking, drying, hot water, and preps for a whole-home generator. Nestled in gated Winding Cypress—praised as Naples' best lifestyle value with remarkably low HOA fees that cover comprehensive maintenance (lawn care, irrigation, community upkeep) plus full access to extensive high-end amenities—you'll embrace the pet-friendly lifestyle with two dedicated dog parks, miles of scenic walking/biking trails across 800+ acres of preserved natural land, and a vibrant social calendar with events curated by the on-site activities director. Resort-style perks include the on-site Shady Palm Café for casual dining and drinks, state-of-the-art fitness center with movement/yoga room, sparkling resort pool and spa, lighted tennis and pickleball courts, bocce courts, community garden, fire pit, and more—all accessible by foot, bike, or golf cart. Conveniently located between downtown Naples and Marco Island, you're minutes from pristine beaches, upscale shopping, and fine dining. Paradise is calling.
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MaryBeth Baron
Achieve Realty LLC
(216) 306-5682
24 Total Sales
4 in Winding Cypress
$850K - $875K Price Range
ML Meade
Premier Sotheby's Int'l Realty
(239) 977-8398
357 Total Sales
2 in Winding Cypress
$680K - $739K Price Range
Vito A Galatro
Premier Sotheby's Int'l Realty
(239) 307-0455
47 Total Sales
1 in Winding Cypress
$1,100,000 Price
Steven Purcell
Re/Max Alliance Group
(239) 351-1178
67 Total Sales
7 in Winding Cypress
$1.2M - $1.7M Price Range
Zachary Dreier
Premier Sotheby's Int'l Realty
(239) 429-0267
144 Total Sales
1 in Winding Cypress
$1,300,000 Price
Brian Giacomello
William Raveis Real Estate
(239) 788-1693
70 Total Sales
2 in Winding Cypress
$470,000 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 | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $138,725 | Accommodation | |
| Warranty Deed | $363,075 | 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 | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $277,450 | New Conventional | |
| Previous Owner | $290,460 | New Conventional |
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 |
|---|---|---|---|---|
| 07/14/2026 07/14/26 | Sold | $565,000 | -3.4% | $364 / Sq Ft |
| 05/26/2026 05/26/26 | Pending | -- | -- | -- |
| 03/28/2026 03/28/26 | Price Changed | $585,000 | -2.5% | $376 / Sq Ft |
| 02/14/2026 02/14/26 | For Sale | $599,999 | -- | $386 / 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 |
|---|---|---|---|---|
| 2026 | $4,800 | $324,275 | ||
| 2025 | $4,800 | $315,750 | ||
| 2024 | $4,557 | $306,851 | ||
| 2023 | $4,557 | $297,914 | $0 | $0 |
| 2022 | $4,046 | $289,237 | $0 | $0 |
| 2021 | $4,065 | $280,813 | $0 | $0 |
| 2020 | $3,995 | $276,936 | $0 | $0 |
| 2019 | $3,940 | $270,710 | $72,754 | $197,956 |
| 2018 | $2,325 | $97,769 | $97,769 | $0 |
| 2017 | $1,222 | $19,378 | $19,378 | $0 |
Seller's Agent in 2026
Jeff Waldman
Premiere Plus Realty Company
(239) 537-3334
4 in this area
20 Total Sales
Source: Naples Area Board of REALTORS®
MLS Number: 226006913
APN: 82679017840
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