5900 Cypress Hollow WAY, Naples, FL, 34109 | $999,000

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.

Features

  • Amenities: Underground Utility
  • Bedrooms: 3
  • Baths: 2 full
  • Style: 2 Story
  • Development: TALL PINES
  • Year Built: 1985
  • Garage: 2.00 Attached
  • Heating: Central Electric
  • Cooling: Central Electric
  • Approx Sq. Feet: 2,600
  • Acreage: 0.34
  • Est. Taxes: $8,103
  • HOA Fee: $875 Annually
  • Lot Desc: Regular
  • View: Wooded Area
  • Community Type: Non-Gated
  • Elem. School: OSCEOLA
  • Middle School: PINE RIDGE
  • High School: BARRON COLLIER
  • Private Pool: Yes
  • Pet Policy: No Approval Needed
  • MLS#: 225083898
  • Website: https://www.raveis.com
    /prop/225083898/5900cypresshollowway_naples_fl?source=qrflyer
Copyright © 2026  The source of this real property information is the copyrighted and proprietary database compilation of the Southwest Florida MLS organizations Copyright Southwest Florida MLS organizations. All rights reserved.
Courtesy of KW Elevate Luxury

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Melissa CohnRVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 16953

917.838.7300

Melissa.Cohn@raveis.com

Our Executive Mortgage Banker:

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5900 Cypress Hollow WAY, Naples, FL, 34109

$999,000

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Melissa Cohn

RVP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 917.838.7300

Melissa.Cohn@raveis.com

NMLS Mortgage Loan Originator ID 16953

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $799,200 $799,200 $799,200
Term 360 months 360 months 180 months
Initial Interest Rate** 5.500% 6.000% 5.750%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.229% 6.098% 5.972%
Monthly Tax Payment $675 $675 $675
H/O Insurance Payment $92 $92 $92
Initial Principal & Interest Pmt $4,538 $4,792 $6,637
Total Monthly Payment $5,305 $5,559 $7,404

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.  The Total Monthly Payment does not include the estimated HOA/Common Charge payment.