Save THOUSANDS: Work with the Top Rated Military Real Estate Team

Let's Go!

255 Cypress Drive
Santa Rosa Beach, FL 32459

$1,999,000

Beds: 5
Baths: 5
Sq. Ft.: 3,217
Type: House
Listing #995769
Experience coastal living at its absolute finest in this extraordinary 3-story turn-key beach retreat, perfectly positioned on one of the highest elevations in Cypress Dunes--offering some of the most breathtaking Gulf of America 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 residence captures the beauty of the Gulf, with expansive porches and elevated vantage points 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 hard t 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!
Property Features
Location Information
County: Walton
Sub Area: 1701 Santa Rosa Beach S of 98 West of 393
MLS Area: 30A West
Latitude: 30.360641
Longitude: -86.269352
Project Name/Subdivision: CYPRESS DUNES
Directions: From U.S. Highway 98, turn south on Highway 30A. Proceed approx 1 mile. Turn right on Cypress Crossing, drive past mail kiosk to entrance gate, turn left on Cypress Drive, continue on Cypress Drive to property on left.
Interior Features
Total Rooms: 15
Interior: Breakfast Bar, Kitchen Island, Lighting Recessed, Owner's Closet, Pantry, Washer/Dryer Hookup, Woodwork Painted
Full Baths: 5
Cooling: Ceiling Fans, Central Air
Appliances: Auto Garage Door Opn, Dishwasher, Disposal, Dryer, Microwave, Oven Self Cleaning, Refrigerator W/IceMk, Smoke Detector, Stove/Oven Gas, Washer, Wine Refrigerator, Water Heater - Elect
Exterior Features
Style: Beach House
Stories: 3
Exterior: Balcony, BBQ Pit/Grill, Columns, Sprinkler System
Parking Description: Garage, Oversized
Has Garage: Yes
Garage Spaces: 2
Has a Pool: Yes
Pool Description: None
Lot Features: Covenants, See Remarks
Dimensions: 50/89/20/89
Zoning: Resid Single Family
Condition: Construction Complete
Has Waterfront: No
View Description: Gulf
Is One Story: No
School
Elementary School: Van R Butler
Middle School: Emerald Coast
High School: South Walton
Additional Information
Property Type: SFR
Year Built: 2006
Status: Active
Home Owners Association: Y
HOA Fee: $1,250
HOA Frequency: Quarterly
HOA Includes: Accounting, Ground Keeping, Land Recreation, Legal, Management, Recreational Faclty, Security, Trash
Tax Year: 2025
Tax Amount: $14,012.73
Community Features: Short Term Rental - Allowed, Pickle Ball, Community Room, Elevators, Exercise Room, Gated Community, Handicap Provisions, Pool, Tennis, TV Cable, Whirlpool


$ per month
Year Fixed. % Interest Rate.
Principal + Interest: $
Monthly Tax: $
Monthly Insurance: $
Term
yrs
Interest Rate
 % 
Down Payment
$
List Price:
$
Based on a fully amortized fixed rate loan. Ask your agent for the tax rates in your area. Insurance estimate is based on an average cost, your final premium cost will be determined by the type of coverage you select. This program only provides an estimate.
Listing Courtesy of EXP Realty LLC
© 2026 Emerald Coast Association of REALTORS®. All rights reserved.
Copyright 2026 Emerald Coast Association of REALTORS®. All rights reserved.
IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is Deemed Reliable, but is Not Guaranteed Accurate by the Emerald Coast Association of REALTORS® MLS. (iHomefinder, Inc Member Number 28165)
ECAR MLS data last updated at February 20, 2026, 8:51 AM CT