5+ Days Ago
Highlights
- Fitness center
- Exceptional amenities
- Breathtaking golf course views
- Lake views
- Golf
Location
1585 Winding Oaks Way #203, Naples, FL 34109, USA|South Hampton
Tour 1585 Winding Oaks Way #203
Contact
Downing-Frye Realty Inc
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Property Overview
Featuring exceptional amenities, including a fitness center and stunning views of the golf course and lake, the property is situated in a vibrant community with accessible public spaces and a diverse mix of residents. With 43 photos available for a comprehensive view and a strong value per square foot ranking, it presents a compelling option for those seeking an active social life in a bustling neighborhood.
This summary uses Zumper’s proprietary data. “Things you’ll love” and “Great for” are based on our internal analyses of market trends and renter insights.
Things you’ll love
More space- Images Available
Great for
Social life
Amenities for 1585 Winding Oaks Way #203, South Hampton
Apartment Amenities
| Carpet | Central Air |
| Electric Heating | Furnished |
| Walk-in Closet |
Appliances
| Dishwasher | In-Unit Laundry |
Building
| Exterior Type: Block | Fitness Center |
| Four Units in Building |
Other
| Exterior Type: Concrete | Three Rooms |
| View Type: Golf Course | View Type: Lake |
Units, floor plans, amenities, dimensions, details, availability, and prices may be approximate and subject to change. Please contact a community representative for more information.
Policies and fees
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About 1585 Winding Oaks Way #203
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Apartments in Bonita Springs-NaplesSouth Hampton 1585 Winding Oaks Way #203, Naples, FL 34109, USA
Apartments in Bonita Springs-NaplesSouth Hampton 1585 Winding Oaks Way #203, Naples, FL 34109, USA
Sweet deal!
This listing is 17% below the median price for 3 bedroom apartments in South Hampton.
Property Status: Active Experience breathtaking golf course and lake views from this beautifully furnished and meticulously maintained 3-bedroom, 2-bathroom condo in the highly desirable Braeburn neighborhood of Stonebridge. This spacious second-floor unit offers approximately 2,182 square feet of living space and a total area of 2,600 square feet, making it perfect for seasonal or short-term renters seeking comfort and luxury. This turnkey condo features an open floor plan, stylish furnishings, and access to Stonebridge’s exceptional amenities, including golf, tennis, a fitness center, and dining. Conveniently located near Vanderbilt Beach, shopping, and fine dining, this property is the perfect retreat to enjoy the best of Naples living. Office Phone: (239) 261-2244 Copyright © 2025 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Property highlights
We compared every listing in the surrounding area to determine which amenities are most common. If a building lacks an amenity that most others in the area have, it is a con. If a building has an amenity most others in the area do not, it is a pro. Similarly, price, schools, and size are calculated relative to the size, price, and distance to schools of the other properties nearby.How 1585 Winding Oaks Way #203 compares to other nearby properties.
Positives
- More space
- The 3-bedroom is 472 sqft larger than other listings nearby
- Images Available
- There are at least 10 photos of this address
Considerations
- Greater distance from high schools
- The nearest high school is farther than 3 miles away
- Grow a garden indoors
- A balcony, backyard, or shared outdoor space isn't available
Address details
| Neighborhood | South Hampton |
|---|---|
| Zip code | 34109 |
| Type | Condo for rent |
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Rent trends in South Hampton
3-bedroom apartments at 1585 Winding Oaks Way #203 cost about 17% less than the average rent price for 3-bedroom apartments in Bonita Springs-Naples.
Median rents as of Oct 18 2025.
South Hampton
Bonita Springs-Naples
| Month | Median Rent |
|---|---|
| November 2023 | $6,700 |
| December 2023 | $6,955 |
| January 2024 | $6,950 |
| February 2024 | $7,000 |
| March 2024 | $7,000 |
| April 2024 | $6,737 |
| May 2024 | $6,591 |
| June 2024 | $7,040 |
| July 2024 | $6,550 |
| August 2024 | $6,623 |
| September 2024 | $6,387 |
| October 2024 | $6,675 |
| November 2024 | $6,700 |
| December 2024 | $6,998 |
| January 2025 | $6,862 |
| February 2025 | $6,923 |
| March 2025 | $7,150 |
| April 2025 | $6,500 |
| May 2025 | $6,136 |
| June 2025 | $6,123 |
| July 2025 | $5,885 |
| August 2025 | $6,065 |
| September 2025 | $6,062 |
| October 2025 | $6,312 |
| Month | Median Rent |
|---|---|
| November 2023 | $8,500 |
| December 2023 | $8,000 |
| February 2024 | $9,000 |
| March 2024 | $9,000 |
| June 2024 | $8,550 |
| August 2024 | $9,000 |
| June 2025 | $7,500 |
| August 2025 | $9,000 |
| September 2025 | $9,000 |
Affordability calculator
Can I afford to live at 1585 Winding Oaks Way #203?
Bedrooms
3 bedroomsRent-to-income ratio
30%
Slide to adjust the percentage of your monthly income you are willing to spend on rent.
The general rule of thumb is to spend around 30% or less of your income on rent.
Recommended income
$300,000/yr
With your selected rent-to-income ratio, you'd ideally want to make $300,000 annually to afford this 3-bedrooms monthly rent price of $7,500.
For more information on rent affordability, visit our rent calculator.
Rent history
The increase or decrease in monthly rent compared to the previous listing price.| 7 months ago | $7,500 |
Schools near 1585 Winding Oaks Way #203
Pelican Marsh Elementary School
9480 airport rd n
naples, FL, 34109
PK, K-5Public
A
Naples Area Teenage Parenting
2925 titan way
naples, FL, 34116
PK, 6-12Public
Collier Virtual School
3710 estey ave
naples, FL, 34104
K-12Public
C-
New Beginnings Alternative School - Naples
3710 estey ave
naples, FL, 34104
3-8Public
C+
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Internet available near 1585 Winding Oaks Way #203
Neighborhood
South Hampton | Bonita Springs-Naples, FL
NEIGHBORHOOD VIBE
Peaceful and quiet
Noise-canceling headphones not required in this mostly noise free area.
Getting around Naples near 1585 Winding Oaks Way #203
Walking
4/10
Some shops and stores are within a few minutes.
Driving
9/10
Commuting is easy with multiple accessible routes and plenty of parking.
Cycling
4/10
More spots are within biking distance and some roads are cyclist-friendly.
Transit
2/10
There are a few mass transit options within the area.
Points of interest for 1585 Winding Oaks Way #203, Naples
Groceries
3/10
At least one grocery store within a 30-minute walk
Shopping
4/10
Some shops within walking distance
Cafes
3/10
Few or no cafés within walking distance
Restaurants
4/10
Some restaurants within walking distance
Primary schools
5/10
At least one elementary school within a 30-minute walk
High schools
0/10
No high schools within a 30-minute walk
Nightlife
1/10
Few or no bars within walking distance
Explore the area around 1585 Winding Oaks Way #203
Sam's Club
2550 Immokalee Rd
BDC Marketplace LLC
129 Wading Bird Cir
European Food Market
5437 Airport Pulling Rd N
Founders Market
7947 Airport Pulling Rd N
Food & Thought Two
7941 Airport Rd N
Sam's Club
2550 Immokalee Rd
J D Bridal Boutique
2359 Vanderbilt Beach Rd
Kathryn's Collection Inc
2355 Vanderbilt Beach Rd
Mainstream Boutique
2355 Vanderbilt Beach Rd
Zazou
2355 Vanderbilt Beach Rd
Planet Smoothie
2400 Immokalee Rd
Foxtail Coffee
2700 Immokalee Rd
Aroma Coffee Service
9047 The Lane
eXpress(o)
2600 Tiburon Dr
Starbucks
2315 Vanderbilt Beach Rd
Bella Vista
2600 Tiburon Dr
Gold Golf Course
2620 Tiburon Dr
Sydney's Pub
2620 Tiburon Dr
Alamo Drafthouse Cinema Naples
9118 Strada Pl
Burntwood Tavern
9110 Strada Pl
Naples Olive Oil Company
2368 Immokalee Rd
Walmart Bakery
5420 Juliet Blvd
Pura Vida Miami
9118 Strada Pl
Kakes By Karen LLC
16273 Camden Lakes Cir
GNC
2405 Tarpon Bay Blvd
Italian Bean Delight
10254 Winterview Dr
Sam's Club Cafe
2550 Immokalee Rd
Boston Beer Garden
2396 Immokalee Rd
Joey D's
2356 Immokalee Rd
JZ of Naples, Inc
2396 Immokalee Rd
Winding Oaks
Airport-Creekside
Nottingham Dr
Airport-Creekside
Pelican Marsh
Airport-Creekside
Curling Ave
Airport-Creekside
Pelican Marsh
Airport-Creekside
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