For Sale
Price CutPrice Drop: $30K (09/21)
Single family home for sale at 7564 Winding Cypress Dr, Naples, FL 34114 | MLS# 2026039825 | Listing updated on 2026-10-08
Photo 1 of Single family home for sale at 7564 Winding Cypress Dr, Naples, FL 34114 | MLS# 2026039825 | Listing updated on 2026-10-08
Photo 2 of Single family home for sale at 7564 Winding Cypress Dr, Naples, FL 34114 | MLS# 2026039825 | Listing updated on 2026-10-08
Photo 3 of Single family home for sale at 7564 Winding Cypress Dr, Naples, FL 34114 | MLS# 2026039825 | Listing updated on 2026-10-08
Photo 4 of Single family home for sale at 7564 Winding Cypress Dr, Naples, FL 34114 | MLS# 2026039825 | Listing updated on 2026-10-08
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$1,030,000

Monthly Est:$5,127

  • Beds Icon4 Beds
  • Beds Icon
    2 Baths
  • Beds Icon2,230sqft

7564 Winding Cypress Dr, Naples, FL 34114

$5,127/moEst:

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  • Single Family Residence

  • Built in 2018

  • $514.33/mo HOA

  • 0.15 acre lot

  • $462/sq.ft

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 sh
utters 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.

  • Houzeo last checked: 6 hours ago
  • Listing updated: October 8, 2026 at 12:55 pm
  • Listing Provided by: Alex Ollila (720) 275-0160 DRE #230024248 | Gordon Pass Realty LLC (702) 275-0160
  • Source: Florida Gulf Coast MLS, Fort Myers-FL | MLS#: 2026039825 Florida Gulf Coast MLS, Fort Myers-FL

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    1

  • County

    Collier County

  • City

    Naples

  • Neighborhood

    --

  • Year Built

    2018

  • HOA Fees

    $514.33/mo

  • Finished Area

    2,230 sqft

  • Lot Size

    0.15 acre lot

  • Basement Area

    - sqft

  • MLS Name

    Florida Gulf Coast MLS, Fort Myers

  • MLS Number

    2026039825

  • MLS Status

    Active

  • Days on Market

    16

  • Cumulative Days on Market

    17

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Location

HOA Management

N/A

HOA Fees

$1,543/ Quarterly

Amenities

Amenities and services may be covered by one or multiple associations and service providers.

Insurance Insurance

Park Playground Park Playground

Pool Pool

Tennis Tennis

Spa Spa

Trash Pickup Trash Pickup

Water Water

Internet Internet

Club House Club House

Maintenance Maintenance

Gym Gym

Sewer Sewer

Road Maintenance Road Maintenance

Security Guard Security Guard

Library Library

Restaurant Restaurant

Walk path Walk path

Sports Court Sports Court

LegalAccounting LegalAccounting

PestControl PestControl

ReserveFund ReserveFund

AssociationManagement AssociationManagement

StreetLights StreetLights

RecreationFacilities RecreationFacilities

Cabana Cabana

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 2

Interior

  • Sewer

    Public Sewer

  • Exterior Features

    Outdoor Grill, Patio, Shutters Electric, Gas Grill

  • Interior Features

    Built In Features, Bedroom On Main Level, Dual Sinks, Family Dining Room, Kitchen Island, Living Dining Room, Main Level Primary, Pantry, Sitting Area In Primary, Shower Only, Separate Shower, Walk In Pantry, Bar, Walk In Closets, Window Treatments, High Speed Internet, Split Bedrooms

  • Flooring

    Tile

  • Window Features

    Impact Glass, Window Coverings

  • Heating

    Central, Electric

  • Cooling

    Central Air, Ceiling Fans, Electric

  • Appliances

    Dryer, Dishwasher, Freezer, Gas Cooktop, Disposal, Ice Maker, Microwave, Refrigerator, Refrigerator With Ice Maker, Wine Cooler, Washer

Construction

  • Year Built

    Year Built: 2018

  • Home type

    Single Family Residence

  • Roof

    Tile

  • Architectural Style

    Ranch, One Story

  • Construction Materials

    Block, Concrete, Stucco

  • Property Condition

    Resale

Utilities & Energy

  • Pool Features

    Concrete, In Ground, Pool Equipment, Community

  • Security Features

    Security System, Smoke Detectors

  • Parking Features

    Attached, Deeded, Driveway, Garage, Paved, Two Spaces, On Street, Garage Door Opener

  • Laundry Features

    Inside

  • Association Amenities

    Bocce Court, Cabana, Clubhouse, Dog Park, Fitness Center, Library, Pickleball, Park, Pool, Restaurant, Spa Hot Tub, Sidewalks, Tennis Courts

  • Water Source

    Public

  • Utilities

    Cable Available, High Speed Internet Available, Underground Utilities

Other Features

  • Community Features

    Gated, Tennis Courts, Street Lights

  • Patio And Porch Features

    Lanai, Patio, Porch, Screened

  • Lot Features

    Rectangular Lot

  • Subdivision Name

    Winding Cypress

Price History

DateEventPrice

09/21/2026

Source: mls_logoFlorida Gulf Coast MLS, Fort Myers-FL #2026039825

Price Decreased

$1,030,000 -2.83%

$462/sqft

09/21/2026

Source: mls_logoFlorida Gulf Coast MLS, Fort Myers-FL #2026039825

Listed for Sale

$1,060,000

$475/sqft

Nearby Homes

Based on information from the Florida Gulf Coast Multiple Listing Service, Inc. through Oct 08, 2026, 11:00AM. IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information provided is deemed reliable but is not guaranteed and should be independently verified. Some IDX listings have been excluded from this website. © 2026 Florida Gulf Coast Multiple Listing Service - All Rights Reserved.

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