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$999,000
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Property Description
In the heart of central Naples-minutes to the beach and located within one of the area's most established neighborhoods and an X flood zone (no insurance required) - this fully renovated two-story pool home offers a rare combination of location, modern upgrades, and outdoor space. With over $400,000 in renovations, this move-in-ready property stands out as a unique offering in today's market. The interior has been completely reimagined with a brand-new kitchen, all-new bathrooms, updated flooring, upgraded lighting with LED accents, barn doors, and thoughtfully selected finishes throughout. Spacious bedrooms include new closet doors, custom built-ins, and closet organization systems. The main level features two guest bedrooms and a refreshed full bath, while the upper level offers a unique flex loft space, and a primary suite with tropical views and a spa-inspired bathroom with a custom walk-in shower. Outdoor living is highlighted by an east-facing, saltwater heated pool with sun shelf, overflow spa, and water features. Expansive impact sliders open to a two-story lanai, creating a seamless connection between indoor and outdoor spaces. The fully fenced, estate-sized yard and rear garage access enhance both privacy and functionality. The property is located in Tall Pines, a community known for its tight-knit community feel and calendar of resident-led neighborhood events held throughout the year. Conveniently situated in walking or biking distance to shopping, dining, and easy access to Naples beaches, this home offers an exceptional blend of location, upgrades, and lifestyle.
Full Property Details
Full Property Details for 5900 Cypress Hollow Way
General
- Price: $999,000
- HOA FEE: $73/month
- HOA FEE FREQ.: Annually
- Taxes: (2024)
- Status: Active
- Type: Single Family
- Source: Bonita_Springs
- MLS ID: 225083898
- Updated: 12/30/2025
- Added to Site: 30 day(s) ago
Interior
- Interior Features: Den - Study, Family Room, Loft, Entrance Foyer, Pantry, Volume Ceiling, Walk-In Closet(s)
- Appliances: Electric Cooktop, Disposal, Double Oven, Dryer, Microwave, Refrigerator/Freezer, Self-Cleaning Oven, Washer
- Furnishings: Negotiable
- Flooring: Carpet, Tile, Vinyl, Wood
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
- Primary Bathroom: Dual Sinks
Bedrooms
- Total Bedrooms: 3
- Primary Bedroom: Master BR Upstairs
Other Rooms
- Kitchen: Kitchen Island, Pantry
- Dining Room: Dining - Family, Eat-in Kitchen
- Laundry: Inside, Sink
Additional Information
- Shared Amenities: Non-Gated
- Pool: Yes
- Private Pool: Yes
- Pool Description: In Ground, Concrete, Custom Upgrades, Equipment Stays, Electric Heat, Salt Water, Screen Enclosure
- Spa: Yes
- Spa Description: In Ground, Concrete, Equipment Stays, Heated (Electric), Integrated with Pool, Screened
- Security/Safety: Smoke Detector(s), Smoke Detectors
Exterior
- Exterior Features: Automatic Sprinkler
- Porch/Patio/Deck: Screened Lanai/Porch
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Driveway Paved, Garage Door Opener, Attached
Location
- Area: NA41 - GGE 3, 6, 7, 10, 11, 19, 20, 21, 37, 52, 53
- County: Collier
- Subdivision: TALL PINES
- Building Name: TALL PINES
- Driving Directions: From I75 head West on Pine Ridge, turn North on Airport Pulling and Tall Pines will be on your right at the intersection of Naples Blvd and Airport Pulling. Drive straight back and turn right on Cypress Hollow Way.
- Direction Faces: West
School Information
- Elementary School: OSCEOLA
- Middle School: PINE RIDGE
- High School: BARRON COLLIER
Community
- Association: Yes
- Assoc. Fees Include: Maintenance Grounds
- Units Assoc/Comm: 1
- Pets Allowed: Yes
- Management Type: Residents
Heating & Cooling
- Air Conditioning: Yes
- Cooling Type: Central Electric
- Heating Type: Central Electric
Utilities
- Sewer: Septic Tank
- Water: Central
- Cable Available: Yes
- Utility Description: Underground Utilities, Cable Available
Structural Information
- Description/Design: Single Family Residence
- Exterior Const.: Wood Frame, Wood Siding
- Roof: Metal
- Windows: Impact Resistant, Other, Single Hung, Skylight(s), Sliding, Solar Tinted, Impact Resistant Windows, Shutters - Manual, Window Coverings
- Doors: Impact Resistant Doors
- Stories/Levels: 2
- Stories in Building: 2
- Square Feet: 2,600
- Sq. Ft. Source: Survey
- Living Area: 2,600 Sq. Ft.
- Year Built: 1985
Lot Features
- Property View: Trees/Woods
- Lot Size (Acres): 0.34
- Lot Size (Sq. Ft.): 14,810
- Lot Size Source: Survey
- Lot Dimensions: 90 x 90 x 165 x 165
- Frontage: Public Road
- Frontage Feet: 90
- Fence: Yes
- Irrigation System: Other
- Lot Features: Regular
- Lot Description: Regular
- Fencing (Description): Fenced
Water Features
- Water Front Desc.: None
- Canal Width: None
Financial Considerations
- Association Fee: $875
- Assoc Fee Freq.: Annually
- Tax Year: 2024
- Terms: Buyer Finance/Cash, FHA, VA Loan
Disclosures and Reports
- Ownership: Single Family
- Legal Description: TALL PINES LOT 55 OR 1525 PG 781
- Property ID: 76363040003
- Section: 12
- Lot Number: 55
Listed by KW Elevate Luxury
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Schools
Schools serving 5900 Cypress Hollow Way
School District:Collier County School District
| Name | Grades | Distance |
|---|---|---|
Osceola Elementary School, Naples, FL 5770 Osceola Trail, Naples, FL 34109 | K-5 | 0.4 mi |
Pine Ridge Middle School 1515 Pine Ridge Road, Naples, FL 34109 | 6-8 | 1.4 mi |
Barron Collier High School 5600 Cougar Drive, Naples, FL 34109 | 9-12 | 0.2 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 5900 Cypress Hollow Way
Date
Details
Price
Change
Source
12/18/2025
Listed
$999,000
23.33%
MLS
2/01/2022
Sold
$810,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 5900 Cypress Hollow Way
Year
Property Taxes
Change
Tax Assessment
Change
2025
$8,103
—
$855,400
1%
2024
$8,103
-1%
$850,140
6%
2023
$8,179
186%
$799,881
189%
2021
$2,855
1%
$276,804
-3%
2022
$2,829
-1%
$285,108
4%
2021
$2,855
4%
$272,982
2%
2019
$2,738
-20%
$266,845
-19%
2018
$3,410
2%
$328,494
2%
2017
$3,358
49%
$321,738
43%
2016
$2,261
-1%
$224,302
1%
2015
$2,279
9%
$222,743
1%
2014
$2,097
—
$220,975
2%
2013
$2,087
—
$217,709
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 5900 Cypress Hollow Way
5900 Cypress Hollow Way, Naples, FL 34109 (MLS# 225083898) is a Single Family property with 3 bedrooms and 2 full bathrooms. 5900 Cypress Hollow Way is currently listed for $999,000 and was received on December 18, 2025. Want to learn more about 5900 Cypress Hollow Way? Do you have questions about finding other Single Family real estate for sale in Naples? You can browse all Naples real estate or contact a Coldwell Banker agent to request more information.

