1975 Gulf Shore Boulevard S
About This Property
Designed by the esteemed Stofft Cooney Architects, the home is a masterwork of Old Florida style reimagined with a contemporary sensibility. From the moment you enter, warm wood floors, custom finishes, and elegant millwork set a tone of understated sophistication. Light pours in through expansive windows, drawing your gaze toward tranquil garden views and a perfectly positioned southern-exposed pool.
The heart of the home-a chef-inspired kitchen-seamlessly unites form and function with premium Wolf and Sub-Zero appliances, a generous island for casual gatherings, and both a butler's pantry and wine bar for elevated entertaining.
A series of open, flowing indoor and outdoor spaces create an inviting atmosphere for both intimate relaxation and grand celebrations. Outside, a private courtyard offers a lush tropical escape with a resort-style pool, summer kitchen, gas fireplace, and shaded dining areas designed for year-round enjoyment. Additionally, having a driveway placed on each side of this corner lot home allows for family & guests to maneuver with comfort and ease.
The owner's suite is a secluded retreat, complete with His & Hers baths, oversized closets, and a peaceful sitting area that invites morning coffee and quiet reflection. Guest accommodations are equally well-appointed, with a private first-floor suite, two additional ensuite bedrooms upstairs, and a private study that can easily transform into an additional bedroom. A separate guest residence with its own drive and entrance provides comfort and privacy for visitors or extended stays-complete with a spacious bedroom, sitting area, and full bath.
For the car enthusiast or collector, two separate two-car garages-one with a lift system-offer room for up to six vehicles, while a full-house generator ensures uninterrupted comfort and convenience.
Every detail of this home has been curated to reflect the relaxed luxury of life by the sea. Just a short stroll to the boutiques and restaurants of 3rd Street South, and mere steps from the beach, this is more than a home-it's your coastal sanctuary in the heart of Naples.
Payment Calculator
Your Estimated Monthly Payment
Cap Rate Calculator
What does this mean?
Based on our analysis, the cap rate of this property is 1.25%. A negative cap rate indicates that the property might not be feasible as an income-producing asset. The median cap rate for a near zip code 11238 is 4.23%.
How much can I actually make?
Actual monthly rental income may vary between $4,760 and $7,140 depending on unit-specific characteristics. You can change the amount using the slider to further explore.
How is cap rate calculated?
Cap Rate = Net Operating Income (NOI) / Property Asset Value.
When calculating the cap rate, we assume 100% occupancy. Leverage (mortgage) is not considered.
Cap Rate provided by RealtyHop and RentHop, learn more about cap rate here.
Price History
| Date / Event | Date | Event | Price |
|---|---|---|---|
| Mar 3, 2026 | Sold | ||
| Sold | |||
| Jan 20, 2026 | In contract | - | |
| In contract | |||
| Sep 15, 2025 | Listed by John R Wood Properties | $8,800,000 | |
| Listed by John R Wood Properties | |||
| Aug 28, 2025 | No longer available | - | |
| No longer available | |||
| Aug 3, 2025 | Price Decreased |
$9,199,000
↓ $291K
(3.1%) | |
| Price Decreased | |||
Property Highlights
Building Info
Comparables
Status
Price/ft²
Listed On
Sold On
Phone: 425-283-2930
Address: 335 Madison Avenue, New York, NY 10017