255 Cypress Drive
About This Property
Experience coastal living at its absolute finest in this extraordinary three-story turn-key beach retreat, perfectly positioned on one of the highest elevations in Cypress Dunes, offering some of the most breathtaking Gulf views in the entire community. From brilliant sunrise skies to unforgettable sunset panoramas, the views from this home are nothing short of spectacular.
Designed to fully embrace its premier setting, every level of this beautifully maintained residence captures the beauty of the Gulf, with expansive porches and elevated living spaces showcasing emerald waters, endless horizons, and soothing coastal breezes. The rare high-elevation homesite not only maximizes sweeping views but also provides an added sense of privacy, security, and distinction that is increasingly difficult to find. Whether as a primary residence, luxury second home, or investment property with outstanding rental potential, this is a rare opportunity to own one of Cypress Dunes' premier view properties at an exceptional price. Cosmetic updates can always be made--but a location and Gulf views like these are truly irreplaceable.
Beyond its beauty, this property presents a compelling investment opportunity. With documented 2025 rental projections of $100,000+ (part-time short-term rentals), this home offers exceptional income potential while serving as a luxurious personal retreat. Its desirable location, three-story layout, and panoramic Gulf views make it highly attractive to vacation renters seeking a premium coastal experience. Whether you're searching for a high-performing investment, a second home, or a legacy property to enjoy for generations, this elevated Gulf-view masterpiece delivers on every level.
Located in the highly sought-after community of Cypress Dunes in Santa Rosa Beach, this exceptional home seamlessly blends timeless architectural charm, thoughtful coastal design, and an unbeatable setting. Residents enjoy resort-style amenities, including a breathtaking Gulf-view infinity-edge pool, a fully equipped fitness center, and a relaxing spa tub--all designed to elevate everyday living.
If you're hosting unforgettable gatherings, savoring peaceful mornings with coffee while gazing out over the Gulf, or unwinding at day's end as the sky melts into brilliant sunset hues, this property captures the very essence of refined beachside living. Here, every moment feels like a getaway, and the coastal lifestyle you've dreamed of becomes your daily reality.
Opportunities to own a home with this level of elevation and view are rare--don't miss your chance to secure one of the best vantage points in Cypress Dunes!
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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 |
|---|---|---|---|
| Jun 30, 2026 | Price Decreased |
$1,750,000
↓ $140K
(7.4%) | |
| Price Decreased | |||
| May 29, 2026 | Price Decreased |
$1,890,000
↓ $59K
(3%) | |
| Price Decreased | |||
| May 5, 2026 | Price Decreased |
$1,949,000
↓ $50K
(2.5%) | |
| Price Decreased | |||
| Feb 18, 2026 | Listed by EXP Realty LLC | $1,999,000 | |
| Listed by EXP Realty LLC | |||
| Nov 15, 2025 | Price Decreased |
$1,999,000
↓ $101K
(4.8%) | |
| Price Decreased | |||
Phone: 425-283-2930
Address: 335 Madison Avenue, New York, NY 10017