3296 LOOKOUT LN, Naples, FL, 34112 | $18,500

Experience resort-style living in this beautifully updated custom home, now available for seasonal or annual rental in the prestigious Windstar on Naples Bay community. Offering a rare combination of luxury, comfort, and lifestyle amenities, this residence is perfect for those seeking an elevated Naples experience.
Inside, the home showcases refined craftsmanship with custom 8-foot solid-core doors, premium hardware, plantation shutters, and a striking marble-faced fireplace. The spacious chef’s kitchen is designed for both everyday living and entertaining, featuring custom cabinetry, a large walk-in pantry, and updated appliances. Skylights and custom lighting enhance the bright, inviting atmosphere, while a dedicated home office provides a quiet space for work or relaxation.
Seamless indoor-outdoor living is at the heart of this property. Expansive 10-foot sliding glass doors open to a private tropical courtyard complete with a heated pool, spa, and tranquil waterfall. A separate guest cabana offers ideal accommodations for visitors, creating a true retreat-like setting.
From the screened lanai, enjoy serene views of the golf course, lake, and surrounding mangroves—perfect for morning coffee or evening sunsets. Additional conveniences include storm shutters, a central vacuum system, brick paver driveway, a two-car garage, and an AquaLink system for effortless pool and spa control.
As a resident, you’ll have access to the exceptional amenities of Windstar, including a Tom Fazio-designed championship golf course, a newly renovated clubhouse overlooking Naples Bay, a deep-water marina with direct Gulf access in minutes, clay tennis courts, and a state-of-the-art fitness center. The private Keewaydin Island Beach Club, accessible via shuttle boat, offers a truly unique coastal experience.
A transferable golf membership may be available, allowing tenants to fully enjoy the exclusive lifestyle this community is known for.
This is a rare opportunity to lease a luxury home in one of Naples’ most sought-after gated waterfront and golf communities.

Features

  • Type: Single Family
  • Amenities: Beach - Private,Beach Club Included,Cabana,Exercise Room,Fitness Center Attended,Golf Course,Internet Access,Private Membership,Putting Green,Restaurant,Sidewalk,Streetlight,Tennis Court,Underground Utility
  • Bedrooms: 3
  • Baths: 3 full
  • Style: 1 Story/Ranch
  • Development: WINDSTAR
  • Year Built: 1999
  • Garage: 2-car Attached
  • Heating: Central Electric
  • Cooling: Ceiling Fans,Central Electric
  • Approx Sq. Feet: 2,647
  • View: Lake,Landscaped Area,Mangroves,Water
  • Community Type: Gated
  • Private Pool: Yes
  • Pet Policy: With Approval
  • MLS#: 226017051
  • Website: https://www.raveis.com
    /prop/226017051/3296lookoutln_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 John R Wood Properties

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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:

  • Is available to meet with you in our office, your home or office, evenings or weekends
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Our Insurance Division:

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3296 LOOKOUT LN, Naples, FL, 34112

$18,500

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 Conforming*
30 Year
Fixed-Rate Conforming
15 Year
Fixed-Rate Conforming
Loan Amount $14,800 $14,800 $14,800
Term 360 months 360 months 180 months
Initial Interest Rate** 6.250% 6.750% 5.875%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.634% 6.890% 6.078%
Monthly Tax Payment N/A N/A N/A
H/O Insurance Payment $75 $75 $75
Initial Principal & Interest Pmt $91 $96 $124
Total Monthly Payment $166 $171 $199

* 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.