For Sale
No HOANo HOA
Single family home for sale at 7775 Winding Cypress Dr, Naples, FL 34114 | MLS# 226037594 | Listing updated on 2026-11-01
Photo 1 of Single family home for sale at 7775 Winding Cypress Dr, Naples, FL 34114 | MLS# 226037594 | Listing updated on 2026-11-01
Photo 2 of Single family home for sale at 7775 Winding Cypress Dr, Naples, FL 34114 | MLS# 226037594 | Listing updated on 2026-11-01
Photo 3 of Single family home for sale at 7775 Winding Cypress Dr, Naples, FL 34114 | MLS# 226037594 | Listing updated on 2026-11-01
Photo 4 of Single family home for sale at 7775 Winding Cypress Dr, Naples, FL 34114 | MLS# 226037594 | Listing updated on 2026-11-01
46+
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Street View

$990,000

Monthly Est:$4,928

  • Beds Icon4 Beds
  • Beds Icon
    3 Baths
  • Beds Icon3,206sqft

7775 Winding Cypress Dr, Naples, FL 34114

$4,928/moEst:

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  • Single Family Residence

  • Built in 2019

  • $514.33/mo HOA

  • 0.2 acre lot

  • $309/sq.ft

Description

Thank you for taking a look at the best value in sought after Winding Cypress! This pristine, 2-Story Summerwood Model, is loaded with options and is located on one of the nicest, private, and quiet lots in the entire community. This amazing home is perfectly situated on a lake's edge with a preserve backdrop. It's on a cul-de-sac with no thru traffic, and miles off of major roadways so it's incredibly quiet, private, with no road noise.
If you are looking for a luxurious and functional space to entertain guests, or have them spend some overnights visiting, this is the property for you. Pride of original ownership is clear. With over 3200 square feet there's incredible r
oom to entertain while also providing privacy for visitors. This home boasts 4 bedrooms, 3 full baths, and a large office or flex room that can be used as the new owner desires. The upstairs area is expansive with a huge gathering space that can be used as a theater room, craft area, media room, or office. The upstairs has it's own large bedroom and full bathroom. The 2nd floor also has it's own zoned climate control with a dedicated additional HVAC unit. The upgrades and amenities that this property offers are impressive. These features include: an upgraded kitchen package that adds optional cabinets, quartz counters & premium appliances, plank tile flooring, an incredible extended great room gathering space, built-in saltwater pool w/integral spa, a whole house generator, easy-use accordion shutters, hurricane rated electric shades enclosing the lanai, an outdoor summer kitchen, surround sound ceiling speakers, an upgraded, private owner's suite, built-in closet organizers, convenient interior plantation shutters, and a deep 2 car garage with epoxy flooring and a must have 2nd refrigerator.
Winding Cypress is an amenity rich, natural gas community and a hidden gem of Naples. Meet friends and neighbors at the resident's only, full-service restaurant and bar that's conveniently located at the edge of the incredible resort pool. Play pickleball, tennis, or bocce on the premium lighted courts. Take advantage of the world-class fitness center. Enjoy the nature trail boardwalk, dog parks, and community garden. Participate in any of the huge selection of activities that the community and HOA offers. Speaking of the HOA, you will not find a better value for cost anywhere in Naples. It's not even close. The HOA General Manager, Assistant Manager, Activities Director, and Support Staff are all full-time and on site to better assist the residents.
Winding Cypress is conveniently located just 10 minutes to the beaches and entertainment on Marco Island, 15 minutes to all that downtown Olde Naples has to offer, 10 minutes to I75, and just 35 minutes to RSW Airport.

  • Houzeo last checked: 10 hours ago
  • Listing updated: November 1, 2026 at 9:13 pm
  • Listing Provided by: Theresa Bocka (239) 351-4955 DRE #281531241, Paul Bocka (585) 576-4250 DRE #638511358 | William Raveis Real Estate (239) 231-3380
  • Source: Florida Gulf Coast MLS, Fort Myers-FL | MLS#: 226037594 Florida Gulf Coast MLS, Fort Myers-FL

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    2

  • County

    Collier County

  • City

    Naples

  • Neighborhood

    --

  • Year Built

    2019

  • HOA Fees

    $514.33/mo

  • Finished Area

    3,206 sqft

  • Lot Size

    0.2 acre lot

  • Basement Area

    - sqft

  • MLS Name

    Florida Gulf Coast MLS, Fort Myers

  • MLS Number

    226037594

  • MLS Status

    Active

  • Days on Market

    8

  • Cumulative Days on Market

    7

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Location

HOA Management

N/A

HOA Fees

$1,543.44/ Quarterly

Amenities

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

Tennis Tennis

Cable TV Cable TV

Club House Club House

Road Maintenance Road Maintenance

Maintenance Maintenance

Insurance Insurance

Spa Spa

Park Playground Park Playground

Security Guard Security Guard

Bike Trails Bike Trails

Gym Gym

Internet Internet

Pool Pool

Restaurant Restaurant

Library Library

Walk path Walk path

Sports Court Sports Court

Management Management

ReserveFund ReserveFund

LegalAccounting LegalAccounting

StreetLights StreetLights

RecreationFacilities RecreationFacilities

AssociationManagement AssociationManagement

IrrigationWater IrrigationWater

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: 3

Interior

  • Appliances

    Built In Oven, Double Oven, Dryer, Dishwasher, Gas Cooktop, Disposal, Ice Maker, Microwave, Range, Refrigerator, Refrigerator With Ice Maker, Self Cleaning Oven, Washer

  • Sewer

    Public Sewer

  • Cooling

    Central Air, Ceiling Fans, Electric

  • Heating

    Central, Electric, Gas, Zoned

  • Interior Features

    Breakfast Bar, Built In Features, Bedroom On Main Level, Dual Sinks, Eat In Kitchen, Family Dining Room, French Doors Atrium Doors, Kitchen Island, Living Dining Room, Main Level Primary, Pantry, Shower Only, Separate Shower, Walk In Closets, Wired For Sound, Window Treatments, High Speed Internet, Home Office, Split Bedrooms

  • Exterior Features

    Irrigation Sprinklers, Outdoor Kitchen, Patio, Shutters Electric, Shutters Manual, Water Feature

  • Window Features

    Single Hung, Shutters, Window Coverings

  • Flooring

    Carpet, Tile

Construction

  • Year Built

    Year Built: 2019

  • Home type

    Single Family Residence

  • Roof

    Tile

  • Property Condition

    Resale

  • Architectural Style

    Two Story

  • Construction Materials

    Block, Concrete, Stucco

Utilities & Energy

  • Pool Features

    Concrete, Gas Heat, Heated, In Ground, Salt Water, Community

  • Association Amenities

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

  • Security Features

    Security Gate, Gated With Guard, Gated Community, Smoke Detectors

  • Water Source

    Public

  • Utilities

    Cable Available, Natural Gas Available, High Speed Internet Available, Underground Utilities

  • Laundry Features

    Inside

  • Parking Features

    Attached, Driveway, Garage, Paved, Garage Door Opener

Other Features

  • Subdivision Name

    Winding Cypress

  • Community Features

    Gated, Street Lights

  • Disclosures

    Disclosure On File, Deed Restriction, Seller Disclosure

  • Lot Features

    Cul De Sac, Dead End, Sprinklers Automatic

  • Patio And Porch Features

    Lanai, Patio, Porch, Screened

Price History

DateEventPrice

10/25/2026

Source: mls_logoFlorida Gulf Coast MLS, Fort Myers-FL #226037594

Listed for Sale

$990,000

$309/sqft

Nearby Homes

Based on information from the Florida Gulf Coast Multiple Listing Service, Inc. through Nov 02, 2026, 02:15PM. 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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