1789 Winding Oaks Way
Description
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,...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
- Listed by Cheri Anne DeMonico • Premier Property Management
Property Details for 1789 Winding Oaks Way
Property Details for 1789 Winding Oaks Way
| Status | Active |
|---|---|
| MLS # | 226019261 |
| Days on Market | 30 |
| Pet Policy | Allowed |
| Rental Incentives | - |
| Costs & Fees | - |
| Available Date | 05/12/2026 |
| Lease Term | Lease Length: 30 |
| Furnished | Unfurnished |
| Property Type | Rental |
| MLS Type | Residential Rental / Villa Detached |
| Year Built | 1999 |
| Lot Size | 0.00 AC / 0 SF |
| County | Collier County |
Location
Virtual Tour
Building Information for 1789 Winding Oaks Way
Property Information for 1789 Winding Oaks Way
- Amenities: Clubhouse, Pool, Community Room, Spa/Hot Tub, Fitness Center, Golf Course, Private Membership, Putting Green, Racquetball, Restaurant, Sidewalk, Streetlight, Tennis Court(s), Underground Utility
- Community Type: Clubhouse, Pool, Fitness Center, Golf Course, Putting Green, Racquetball, Restaurant, Sidewalks, Street Lights, Tennis, Gated
- Pets: With Approval
- Property Features: Cable Prewire
- Carport Desc: Attached
- Carport Spaces: 0
- Attached Garage: Yes
- Garage Spaces: 2
- Carport: No
- Covered Spaces: 2
- Garage: Yes
- Total Parking: 0
- Virtual Tour URL Branded: https://my.matterport.com/show/?m=W3czn7FJeeS&brand=0&mls=1&
- Laundry Features: Laundry in Residence
- Approx Living Area: 1937.0
- Living Area Units: Square Feet
- Bedrooms: 3 Bed
- Elevator: None
- Appliances: Dishwasher, Disposal, Microwave, Range, Refrigerator/Icemaker, Self Cleaning Oven, Washer
- Equipment: Auto Garage Door, Dishwasher, Disposal, Microwave, Range, Refrigerator/Icemaker, Self Cleaning Oven, Smoke Detector, Washer
- Flooring: Carpet, Tile
- Interior Features: Foyer, Pantry, Smoke Detectors, Volume Ceiling, Walk-In Closet, Window Coverings, Cable Prewire
- Spa Features: Community
- Num Unit Floor: 1
- Private Pool Desc: Community, Below Ground, Concrete, Electric Heat
- Private Pool: Yes
- Private Spa: No
- Total Floors: 1
- Baths Full: 2
- Half Bathrooms: 0
- Bathrooms Total Decimal: 2.00
- Bathrooms: 2
- Bedrooms Total: 3
- Fireplace: No
- View YN: Yes
- Additional Rooms: Den - Study, Great Room, Guest Bath, Guest Room, Laundry in Residence, Screened Lanai/Porch
- Exterior Features: Screened Lanai/Porch, Tennis Court(s)
- Windows: Window Coverings
- Cooling: Ceiling Fan(s), Central Electric
- Cooling YN: Yes
- Heat: Central Electric
- Heating YN: Yes
- Structure Type: Villa Detached
- Monthly Rate: $4,995.00
- Horse: No
- Smoking YN: No
- Min Days of Lease: 30
Property History for 1789 Winding Oaks Way
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| May 13, 2026 | Listed (Active) Naples Area Board of REALTORS #226019265 | $12,995 | — |
| May 12, 2026 | Listed (Active) Naples Area Board of REALTORS #226019261 | $4,995 | — |
| Date | Event & Source | Price |
|---|---|---|
| 05/13/2026 | Listed (Active) Naples Area Board of REALTORS #226019265 | $12,995 |
| 05/12/2026 | Listed (Active) Naples Area Board of REALTORS #226019261 | $4,995 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Schools near 1789 Winding Oaks Way
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 5 | |||
| Public - | 6 to 8 | |||
| Public - | 9 to 12 | |||
| Public - | 9 to 12 |
Rating | School | Distance |
|---|---|---|
Pelican Marsh Elementary School PublicPK to 5 | ||
Pine Ridge Middle School Public6 to 8 | ||
Aubrey Rogers High School Public9 to 12 | ||
Collier Virtual Instruction Course Offerings Public9 to 12 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the owner's discretion. No financial or legal advice provided. Equal Housing Opportunity.
Listing Courtesy of Premier Property Management, Cheri Anne DeMonico
The information is being provided in part by Southwest Florida Multiple Listing Service, Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2, and MarcoMls. Information deemed reliable but not guaranteed. Information is provided for consumers' personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2026 Southwest Florida Multiple Listing Service and MarcoMls. All Rights Reserved. The data relating to real estate for sale displayed on this website comes in part from the Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2 and MarcoMls. Properties listed with brokerage firms other than Compass are marked with the "BR House" logo. Detailed information about such properties includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties listed with brokerage firms participating in the Naples MLS BR Program, or contained in the database compilation of Naples MLS.
