5900 Cypress Hollow WAY
Naples, FL, 34109 $ 974,000
Bedrooms3 Baths2.0 Sq 2,600 Monthly Estimate*
$ 5,997
for $974,000 with 3 bedrooms and 2 full baths. This 2,600 square foot home was built in 1985 on a lot size of 0.34.
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. The home was updated with a brand new A/C system installed in 2026, offering comfort and efficiency year-round. 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.
See more
FeaturesInteriorInterior Amenities Foyer Laundry Tub Pantry Pull Down Stairs Smoke Detectors Volume Ceiling Walk-In Closet(s) Window Coverings
Flooring Carpet Tile Vinyl Wood
Furnished Y/N Negotiable
Total Stories 2
Air Conditioning Y/N Y
Heating Y/N Y
Window Features Skylight(s) Window Coverings
Fireplace Y/N N
Half Baths 0
Laundry Features Laundry in Residence Laundry Tub
Total Bedrooms 3
Total Baths 2
Dining Room Features Dining - Family Eat-in Kitchen
See more
GeneralSewer Septic Tank
Heating Central Electric
Cooling Central Electric
Roof Metal
Appliances Electric Cooktop Disposal Double Oven Dryer Microwave Refrigerator/Freezer Self Cleaning Oven Washer
HOA Fee 875
Garage Spaces 2
Architectural Style Two Story Single Family
Pool Features Pool/Spa Combo Below Ground Concrete Custom Upgrades Equipment Stays Electric Heat Salt Water Screen Enclosure
Security Features Smoke Detector(s)
Construction Materials Wood Frame Wood Siding
Pets Allowed Yes
Year Built 1985
View Trees/Woods
Levels 2
Property Subtype Single Family Residence
Tax Year 2024
Waterfront Features None
County Collier
New Construction N
Property Type Residential
Association Amenities Underground Utility
HOA Y
Attached Garage Y
Subdivision Name TALL PINES
Garage Y/N Y
Full Baths 2
Status Active
High School BARRON COLLIER
City NAPLES
Senior Community Y/N N
Number Of Units Total 1
MLS Area TALL PINES
Lot Size Units Acres
Lot Size Square Feet 14810
Carport Spaces 0
Carport Y/N N
Spa Features Below Ground Concrete Equipment Stays Heated Electric Pool Integrated Screened
Elementary School OSCEOLA
Land Lease Y/N N
Tax Annual Amount 8102.69
Middle/Junior High School PINE RIDGE
Ok to Lease Buyer Finance/Cash FHA VA
Additional Parcels Y/N N
Structure Type House
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
See more
ExteriorExterior Amenities Screened Lanai/Porch
Fencing Fenced
Parking Features Driveway Paved Attached
Lot Features Regular
Water Source Central
Total Parking 2
Lot Size Area 0.34
Park Name TALL PINES
Spa Y
Building Area Total 3900
Lot Size Acres 0.34
Waterfront Y/N N
Covered Spaces 2
Horse Y/N N
See more
* Excluded FeaturesAffordability Calculator
- Monthly Principal & Interest
- $5,997
- Monthly Property Taxes
- $675
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Naples, FL
Average List Price $2,229,788
Percent of Sale Price 129%
About Naples, FL 20,223 Population
-8% Since 2002
$ 92,989 Median Income
66.65 Median Age
8% Households with Children
Trends Information provided by ATTOM Data Solutions.
1022830 Elementary School
1022831 Middle School
Barron Collier High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 2/27/2026 | $974,000 | -2.50% | Price Down |
| 12/18/2025 | $999,000 | | Listed Price |