
1789 Winding Oaks Way, Naples, FL 34109
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
- Drive Time--
- Walk Time--
- Bike Ride Time--
- Public Transit--
Get In Touch
Naples, FL 34109

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
Travel and Transit

Local Education
Primary and Secondary Schools
Pelican Marsh Elementary School
Grades PK-5
Public
Cedar Montessori School
Grades PK-5
Private
Pine Ridge Middle School
Grades 6-8
Public
Aubrey Rogers High School
Grades 9-12
Public
Journeys Academy
Grades K-12
Private
Data provided by GreatSchools.org © 2026. All rights reserved.
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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