# 7564 Winding Cypress Drive, Naples, FL 34114 > **TL;DR:** 4bd/2ba single family, $1,060,000 ($475/sqft), built 2018, 2,230 sqft. > Pool, Spa, Waterfront, View. Est. $7,212/mo. Listed 7 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $1,060,000 | | Price/sqft | $475 | | Bedrooms | 4 | | Bathrooms | 2 full | | Square Feet | 2,230 | | Year Built | 2018 | | Lot Size | 6,752 sqft (0.16 acres) | | Stories | 1 | | Garage | 2-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 7 | ## Why This Home Stands Out - **Pool** - Porch, Patio - **Waterfront** - Waterfront location listed - **Views** - Lake ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $5,360 | | Estimated Insurance | $309 | | HOA | $1,543 | | **Total** | **$7,212** | ## Key Amenities - Pool - Spa - Waterfront - View - A/C - 2-car garage ## Property Highlights - Built in 2018 - 0.15 acre lot - Private pool - Waterfront ## Description ### Agent Description Most lake lots give you water. This one gives you the sunset. The western exposure at 7564 Winding Cypress Drive turns the back of the house into the best seat in the community every evening, and the extended lanai is built with no-see-um mesh in picture-window construction, so the horizon comes through without a frame across it. Behind that view is a one-owner 2018 DiVosta Summerwood, offered for the first time since it was built and expanded well past the standard plan: 2,230 square feet, four bedrooms, ten-foot ceilings, eight-foot doors, and an extended great room under a coffered ceiling with crown molding carried through every room. Arched openings, plantation shutters on every window, and porcelain plank floors give the interior a finished, architectural quality that reads as both coastal and modern. The kitchen was renovated after purchase and it shows: white shaker cabinetry, salt-and-pepper granite, a counter-to-ceiling white subway backsplash, an externally vented stainless chimney hood over a natural gas range, under-cabinet lighting, a wine fridge, a walk-in pantry, and an extended island with seating under glass pendants. The dining area sits beneath its own cluster chandelier, and the great room holds a full sectional, a game table, and a bar cabinet with room to spare. Outside, the lanai is a true second living room. A resort-style saltwater pool with an in-water sundeck, a spa placed on the sight line so the water reads as one composition from inside the house, a Silver River travertine deck, and a covered section deep enough for an outdoor sectional and a six-seat dining table. Natural gas outdoor is included as well. Foxtail and Christmas palms frame the lake beyond. New pool motor in 2024. Then the part that separates a Florida house from a Florida headache. Impact windows, custom window treatments and impact doors are installed throughout. StormSmart electric screens on the lanai and front vestibule. A whole-house and pool Generac generator. A flat concrete tile roof, tankless water heater, and centrally wired alarm. Close the house in May, fly north, and stop watching the tropics. The extended garage has its own split-system A/C; the attic has pull-down stairs and added insulation. The owner's suite carries a California Closets build-out, and every closet in the house has extra shelving. Dimmer switches throughout. The designer furnishings shown, indoors and out, are available under separate negotiation. Bring a suitcase if you like. Winding Cypress is a gated, natural-gas community of 766 homes set inside 800 acres of protected preserve and 80 acres of lakes. Residents have an on-site restaurant and bar, resort and lap pools with a spa and fire pit, an oversized fitness center, tennis, pickleball, bocce, two dog parks, a full activities calendar, and miles of boardwalk and preserve trail. Lawn care is included in the dues. Marco Island's beaches are ten minutes out; Fifth Avenue South is about fifteen. ## Location - **Address:** 7564 Winding Cypress Drive, Naples, FL 34114 - **County:** Collier - **Neighborhood:** WINDING CYPRESS - **Coordinates:** 26.062566, -81.673307 - **Google Maps:** https://www.google.com/maps?q=26.062566,-81.673307 ## Virtual Tour & Media - **Video Tour:** https://www.propertypanorama.com/instaview/fgcmls/2026039825 ## Listing Agent - **Name:** Alex Ollila · **License:** 230024248 - **Brokerage:** Gordon Pass Realty LLC - **Phone:** 7202750160 - **Broker Phone:** 702-275-0160 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/7564-Winding-Cypress-Dr_Naples_FL_34114_M58308-76199?f=listhub&s=FMSWFL&m=2026039825&c=propsimple) ## Photos ![7564 Winding Cypress Drive - Photo 1](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f2724760165r.jpg) ![7564 Winding Cypress Drive - Photo 2](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f55613700r.jpg) ![7564 Winding Cypress Drive - Photo 3](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f1612984637r.jpg) ![7564 Winding Cypress Drive - Photo 4](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f3889745126r.jpg) ![7564 Winding Cypress Drive - Photo 5](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f2124088649r.jpg) ![7564 Winding Cypress Drive - Photo 6](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f1821632727r.jpg) ![7564 Winding Cypress Drive - Photo 7](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f1729008178r.jpg) ![7564 Winding Cypress Drive - Photo 8](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f3256138328r.jpg) ![7564 Winding Cypress Drive - Photo 9](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f3720668746r.jpg) ![7564 Winding Cypress Drive - Photo 10](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f1694048090r.jpg) ![7564 Winding Cypress Drive - Photo 11](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f1701783513r.jpg) ![7564 Winding Cypress Drive - Photo 12](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f1308047965r.jpg) ![7564 Winding Cypress Drive - Photo 13](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f3071044047r.jpg) ![7564 Winding Cypress Drive - Photo 14](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f2571072694r.jpg) ![7564 Winding Cypress Drive - Photo 15](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f3011420903r.jpg) ![7564 Winding Cypress Drive - Photo 16](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f987386609r.jpg) ![7564 Winding Cypress Drive - Photo 17](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f3002066101r.jpg) ![7564 Winding Cypress Drive - Photo 18](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f2482180169r.jpg) ![7564 Winding Cypress Drive - Photo 19](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f2200020240r.jpg) ![7564 Winding Cypress Drive - Photo 20](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f961756816r.jpg) ![7564 Winding Cypress Drive - Photo 21](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f1911352079r.jpg) ![7564 Winding Cypress Drive - Photo 22](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f3259242365r.jpg) ![7564 Winding Cypress Drive - Photo 23](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f246879438r.jpg) ![7564 Winding Cypress Drive - Photo 24](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f3305346290r.jpg) ![7564 Winding Cypress Drive - Photo 25](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f992624285r.jpg) ![7564 Winding Cypress Drive - Photo 26](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f1001079780r.jpg) ![7564 Winding Cypress Drive - Photo 27](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f1346446965r.jpg) ![7564 Winding Cypress Drive - Photo 28](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f569027346r.jpg) ![7564 Winding Cypress Drive - Photo 29](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f485494436r.jpg) ![7564 Winding Cypress Drive - Photo 30](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f1621947230r.jpg) ![7564 Winding Cypress Drive - Photo 31](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f2458163253r.jpg) ![7564 Winding Cypress Drive - Photo 32](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f1341659998r.jpg) ![7564 Winding Cypress Drive - Photo 33](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f195140948r.jpg) ![7564 Winding Cypress Drive - Photo 34](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f1188031078r.jpg) ![7564 Winding Cypress Drive - Photo 35](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f999712421r.jpg) ![7564 Winding Cypress Drive - Photo 36](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f3871905412r.jpg) ![7564 Winding Cypress Drive - Photo 37](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f3987518288r.jpg) ![7564 Winding Cypress Drive - Photo 38](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f2632620825r.jpg) ![7564 Winding Cypress Drive - Photo 39](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f752913466r.jpg) ![7564 Winding Cypress Drive - Photo 40](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f947801870r.jpg) ![7564 Winding Cypress Drive - Photo 41](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f4219240813r.jpg) ![7564 Winding Cypress Drive - Photo 42](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f1256354034r.jpg) ![7564 Winding Cypress Drive - Photo 43](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f1827447468r.jpg) ![7564 Winding Cypress Drive - Photo 44](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f631190384r.jpg) ![7564 Winding Cypress Drive - Photo 45](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f2057892434r.jpg) ![7564 Winding Cypress Drive - Photo 46](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f3384505858r.jpg) ![7564 Winding Cypress Drive - Photo 47](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f1221246623r.jpg) ![7564 Winding Cypress Drive - Photo 48](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f2776645652r.jpg) ![7564 Winding Cypress Drive - Photo 49](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f3313588926r.jpg) ![7564 Winding Cypress Drive - Photo 50](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f3858198055r.jpg) ![7564 Winding Cypress Drive - Photo 51](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f3763897349r.jpg) ![7564 Winding Cypress Drive - Photo 52](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f2086605227r.jpg) ![7564 Winding Cypress Drive - Photo 53](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f587357813r.jpg) ![7564 Winding Cypress Drive - Photo 54](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f1061614930r.jpg) ![7564 Winding Cypress Drive - Photo 55](http://lh.rdcpix.com/25affdc7299ee4500de849c898e1f228l-f407353456r.jpg) --- **MLS#:** 2026039825 | **Updated:** 2026-09-27 **Source:** listhub *Copyright © 2026 Florida Gulf Coast Multiple Listing Service, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/7564-winding-cypress-drive-naples-fl-34114-26039825) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/7564-winding-cypress-drive-naples-fl-34114-26039825#listing", "url": "https://www.propertysimple.ai/listing/7564-winding-cypress-drive-naples-fl-34114-26039825", "name": "7564 Winding Cypress Drive, Naples, FL 34114", "description": "Most lake lots give you water. This one gives you the sunset. The western exposure at 7564 Winding Cypress Drive turns the back of the house into the best seat in the community every evening, and the extended lanai is built with no-see-um mesh in picture-window construction, so the horizon comes through without a frame across it. Behind that view is a one-owner 2018 DiVosta Summerwood, offered for the first time since it was built and expanded well past the standard plan: 2,230 square feet, four bedrooms, ten-foot ceilings, eight-foot doors, and an extended great room under a coffered ceiling with crown molding carried through every room. Arched openings, plantation shutters on every window, and porcelain plank floors give the interior a finished, architectural quality that reads as both coastal and modern. The kitchen was renovated after purchase and it shows: white shaker cabinetry, salt-and-pepper granite, a counter-to-ceiling white subway backsplash, an externally vented stainless chimney hood over a natural gas range, under-cabinet lighting, a wine fridge, a walk-in pantry, and an extended island with seating under glass pendants. The dining area sits beneath its own cluster chandelier, and the great room holds a full sectional, a game table, and a bar cabinet with room to spare. Outside, the lanai is a true second living room. A resort-style saltwater pool with an in-water sundeck, a spa placed on the sight line so the water reads as one composition from inside the house, a Silver River travertine deck, and a covered section deep enough for an outdoor sectional and a six-seat dining table. Natural gas outdoor is included as well. Foxtail and Christmas palms frame the lake beyond. New pool motor in 2024. Then the part that separates a Florida house from a Florida headache. Impact windows, custom window treatments and impact doors are installed throughout. StormSmart electric screens on the lanai and front vestibule. A whole-house and pool Generac generator. A flat concrete tile roof, tankless water heater, and centrally wired alarm. Close the house in May, fly north, and stop watching the tropics. The extended garage has its own split-system A/C; the attic has pull-down stairs and added insulation. The owner's suite carries a California Closets build-out, and every closet in the house has extra shelving. Dimmer switches throughout. The designer furnishings shown, indoors and out, are available under separate negotiation. Bring a suitcase if you like. Winding Cypress is a gated, natural-gas community of 766 homes set inside 800 acres of protected preserve and 80 acres of lakes. Residents have an on-site restaurant and bar, resort and lap pools with a spa and fire pit, an oversized fitness center, tennis, pickleball, bocce, two dog parks, a full activities calendar, and miles of boardwalk and preserve trail. Lawn care is included in the dues. 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