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$4,995 /month

1789 Winding Oaks Way, Naples, FL 34109

Last Updated:

What This House Offers

CALLING ALL GOLFERS ** BEAUTIFUL SINGLE FAMILY PRIVATE HEATED POOL HOME IN STONEBRIDGE COUNTRY CLUB NAPLES ** GOLF TRANSFER HOME ** OFFERED SEASONAL OR ANNUALLY... **Seasonal or Annual Private Pool Home – Stonebridge Country Club,North Naples Experience resort-style living in this beautifully maintained 3-bedroom + office,2-bath single-family HEATED pool home located in the highly sought-after Stonebridge Country Club. This 1,937 sq ft private villa offers a southern exposure with tranquil preserve and pool views,providing the perfect blend of comfort,privacy,and luxury. Property Highlights: Large private heated pool for entertaining Tastefully furnished throughout Spacious open layout with volume ceilings Private screened pool and lanai with Smart TV 2-car garage Bundled golf membership (transfer fee applies) Small dog considered (subject to HOA and owner approval) Interior Features: Primary Suite: King bed,workspace/office area,large walk-in closet Primary Bath: Soaking tub,walk-in shower,dual vanities Guest Bedrooms: Second bedroom: Queen bed Third bedroom: Full bed Shared Jack & Jill bathroom Fully equipped kitchen with granite countertops & stainless steel appliances Smart TVs in primary bedroom,living room,and lanai Extras included: golf clubs,bicycle,pack-n-play,and highchair Location Perks: Just 3 miles to the beach 3 miles to Interstate 75 and Famous Mercato and From Seed to Table for shopping and entertainment Approximately 20 minutes to downtown Naples and 5th Avenue South Centrally located near top dining,shopping,and entertainment Community Amenities – Stonebridge Country Club: Enjoy an active,upscale lifestyle in this gated bundled golf community,featuring: 18-hole championship golf course (redesigned in 2023 by Kipp Schulties) Newly renovated clubhouse with multiple dining venues including pool bar\grill Resort-style pool & spa Five Har-Tru tennis courts + pickleball programs Raquetball and Bocce Modern fitness center with classes,trainers & Peloton bikes Scenic walking/jogging paths Vibrant social calendar with events,clubs,and entertainment This home offers the ideal Naples country club lifestyle—whether you're relaxing poolside,golfing,or enjoying nearby beaches and attractions. Rates & Availability: Jan-April: $12,995.00 a month Oct-Dec: $11,995.00 a month May-September: $6,495 a month OR Annual Rate: 12 month lease: $4995 a month Tenant responsible for Electricity,Water\Sewer Cable and Internet Owner responsible for lawn,pool and trash First,last and security deposit collected prior to move in ** HOME CANNOT BE OFFERED UNFURNISHED - SORRY **

Unit

  • $4,995 / month
  • 3 Beds
  • 2 Baths
  • 1937 sq. ft.
  • Available May 15

Home Features

  • Dishwasher
  • Disposal
  • Ice Maker
  • Microwave
  • Oven
  • Pantry
  • Range
  • Refrigerator
  • Sprinkler System
  • Walk-In Closets

Community Features

  • Clubhouse
  • Fitness Center
  • Pool
  • Putting Greens
  • Racquetball Court
  • Spa
  • Tennis Court

1789 Winding Oaks Way is a single-family home for rent in Naples, FL

Fees and Policies

The fees below are based on community-supplied data and may exclude additional fees and utilities.

One-Time Basics

Due at Move-In

  • Security Deposit - Refundable
    $4,995

Property Fee Disclaimer Based on community-supplied data and independent market research. Subject to change without notice. May exclude fees for mandatory or optional services and usage-based utilities.

Home Details

Views

  • Views

Home Design

  • Built in 1999
  • Villa

Interior Spaces

  • Vaulted Ceiling
  • Great Room
  • Screened Porch
  • Den
  • Entrance Foyer
  • Ceiling Fan
  • Property has 1 Level
  • Window Treatments

Kitchen

  • Range
  • Ice Maker
  • Microwave
  • Dishwasher
  • Self-Cleaning Oven
  • Disposal

Flooring

  • Tile
  • Carpet

Bedrooms and Bathrooms

  • In-Law or Guest Suite
  • Soaking Tub
  • Walk-In Closet
  • 2 Full Bathrooms
  • 3 Bedrooms | 2 Bathrooms
  • 3 Bedrooms

Laundry

  • Laundry in unit
  • Washer

Home Security

  • Fire and Smoke Detector

Parking

  • 2 Car Attached Garage

Pool

  • Concrete Pool
  • Heated In Ground Pool

Outdoor Features

  • Tennis Courts

Lot Details

  • Landscaped

Utilities

  • Central Heating and Cooling System
  • Cable TV Available
  • Underground Utilities

Listing and Financial Details

  • Assessor Parcel Number 74937007364
  • No Smoking Allowed

Community Details

Overview

  • Private Membership Available
  • Thornbrooke Subdivision
  • 2250 Sq Ft Building

Amenities

  • Clubhouse
  • Meeting Room
  • Restaurant

Recreation

  • Golf Course Community
  • Fitness Center
  • Community Pool
  • Community Spa
  • Tennis Courts
  • Putting Green
  • Racquetball

Pet Policy

  • Pets allowed on a case-by-case basis

Security

  • Gated Community

Matterport 3D Tours

Explore Commute Options

Destination Address
  • Drive Time
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  • Walk Time
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  • Bike Ride Time
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  • Public Transit
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What's nearby 1789 Winding Oaks Way

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Get In Touch

Property Address:
1789 Winding Oaks Way,
Naples, FL 34109
Listed by
Cheri Anne DeMonico | Premier Property Management
Phone Number: (239) 307-7155
FloridaGulfCoastMLS#FL

Information is provided by The Florida Gulf Coast Multiple Listing Service, Inc. Information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Listing(s) information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Copyright © 2026 The Florida Gulf Coast Multiple Listing Service, Inc. All rights reserved.

Area Scores

Walkability

Fairly walkable40 / 100

Driveability

Very drivable80 / 100

Bikeability

Fairly bikeable40 / 100

Scores provided by

Travel and Transit

Airport
Southwest Florida International
36 min Drive
Southwest Florida International

Local Education

Primary and Secondary Schools

10 rating

Pelican Marsh Elementary School

Grades PK-5

Public

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Cedar Montessori School

Grades PK-5

Private

9 rating

Pine Ridge Middle School

Grades 6-8

Public

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Aubrey Rogers High School

Grades 9-12

Public

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Journeys Academy

Grades K-12

Private

Data provided by GreatSchools.org © 2026. All rights reserved.

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Colleges and Universities

School

Commute Time (Distance)

Hodges University, Naples

Drive: 9 min (3.8 mi)

SW Fla. Coll., Bonita Springs

Drive: 21 min (11.9 mi)

Discover North Naples, Naples, FL

Shopping Centers

Shoppers will appreciate 1789 Winding Oaks Way proximity to Greentree Center, Piper's Crossing, and Uptown Center. Greentree Center is 1.4 miles away, and Piper's Crossing is within a 28 minute walk.

Airports

Living in North Naples provides easy access to Southwest Florida International, located just 36 minutes from 1789 Winding Oaks Way.

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