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5 Beds
7 Baths
5,139 sqft

$5,995,000

1560 Osprey AVE, Naples FL, 34102

Price per sqft$1,166.57
Built in2001
Property size5,139 sqft
Property typeResidential

Overview

Active

Listed Oct 18, 2026

Updated 11h ago

Rarely available three-story waterfront residence in Oyster Bay offering exceptional scale, quality construction, and outstanding value in today’s market. With 5,139 SF of AC living area, an additional 1,659 SF of lower-level flex space, a 772 SF garage, more than 9,000 SF under roof, and over 10,000 SF of total usable space including the courtyard, this is a truly substantial property that would be extremely difficult to replicate today. Built with concrete construction on all three levels, the home sits high above flood elevation, with the main living level at approximately 15’6”, well above FEMA’s 10’ flood elevation. Features include impact windows and doors, newer roof, elevator access to all three floors, 80 feet of water frontage, and direct boatable access to Naples Bay with no bridges. The rear southern exposure brings excellent natural light to the home, pool area, and waterfront setting. The dock is ready to enjoy with a boat lift currently holding a 26-foot boat, plus a waterfront pergola with TV and a boathouse-style room with wet bar/kitchenette tucked beneath the main home. The elevated main level offers formal and casual living and dining spaces, a renovated kitchen, large pantry, abundant natural light, and a private guest/mother-in-law suite with its own entrance and staircase. Also on this level, the screened courtyard pool area features a large pool, full pool bath, oversized lanai, outdoor kitchen, and brick oven/fireplace. Upstairs includes two large en-suite guest bedrooms, a private office, and a spacious primary suite with steam shower and sauna. The lower level includes a two-car garage, gym, guest suite, and additional hangout space. Just a 3-minute walk to Naples Bay Club and less than a 20-minute walk to Fifth Avenue, this location is truly hard to beat as one of the few waterfront single-family properties this close to downtown Naples. The neighboring waterfront lot is also available separately, creating the opportunity for a larger compound with additional yard space and water frontage. Come experience the scale, setting, and lifestyle this property has to offer.

$39,885/mo

Est. mortgage payment based on a $5,995,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
226033737

Interior Features

Bedrooms
5
Bathrooms
7
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
0.26 Acres

Other Property Details

Taxes
$32,200
Tax Frequency
Annually
Secondary Association Fee
Not Listed
Garage
Yes
View
Yes
Pets Allowed
Yes
Pool
Yes
Waterfront
Yes
55+/Senior Community
No

Listed by Shay Trask, Gulf Coast International Prop

Listing Contact: (239) 572-1648 

All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) nor Marilyn Worley shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless.

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Data last updated 3:01 PM UTC, 10/21/2026

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