255 Cypress Drive Santa Rosa Beach, FL - Image 1255 Cypress Drive Santa Rosa Beach, FL - Image 2255 Cypress Drive Santa Rosa Beach, FL - Image 3255 Cypress Drive Santa Rosa Beach, FL - Image 4255 Cypress Drive Santa Rosa Beach, FL - Image 5255 Cypress Drive Santa Rosa Beach, FL - Image 6255 Cypress Drive Santa Rosa Beach, FL - Image 7255 Cypress Drive Santa Rosa Beach, FL - Image 8255 Cypress Drive Santa Rosa Beach, FL - Image 9255 Cypress Drive Santa Rosa Beach, FL - Image 10255 Cypress Drive Santa Rosa Beach, FL - Image 11255 Cypress Drive Santa Rosa Beach, FL - Image 12255 Cypress Drive Santa Rosa Beach, FL - Image 13255 Cypress Drive Santa Rosa Beach, FL - Image 14255 Cypress Drive Santa Rosa Beach, FL - Image 15255 Cypress Drive Santa Rosa Beach, FL - Image 16255 Cypress Drive Santa Rosa Beach, FL - Image 17255 Cypress Drive Santa Rosa Beach, FL - Image 18255 Cypress Drive Santa Rosa Beach, FL - Image 19255 Cypress Drive Santa Rosa Beach, FL - Image 20255 Cypress Drive Santa Rosa Beach, FL - Image 21255 Cypress Drive Santa Rosa Beach, FL - Image 22255 Cypress Drive Santa Rosa Beach, FL - Image 23255 Cypress Drive Santa Rosa Beach, FL - Image 24255 Cypress Drive Santa Rosa Beach, FL - Image 25255 Cypress Drive Santa Rosa Beach, FL - Image 26255 Cypress Drive Santa Rosa Beach, FL - Image 27255 Cypress Drive Santa Rosa Beach, FL - Image 28255 Cypress Drive Santa Rosa Beach, FL - Image 29255 Cypress Drive Santa Rosa Beach, FL - Image 30255 Cypress Drive Santa Rosa Beach, FL - Image 31255 Cypress Drive Santa Rosa Beach, FL - Image 32255 Cypress Drive Santa Rosa Beach, FL - Image 33255 Cypress Drive Santa Rosa Beach, FL - Image 34255 Cypress Drive Santa Rosa Beach, FL - Image 35255 Cypress Drive Santa Rosa Beach, FL - Image 36255 Cypress Drive Santa Rosa Beach, FL - Image 37255 Cypress Drive Santa Rosa Beach, FL - Image 38255 Cypress Drive Santa Rosa Beach, FL - Image 39255 Cypress Drive Santa Rosa Beach, FL - Image 40255 Cypress Drive Santa Rosa Beach, FL - Image 41255 Cypress Drive Santa Rosa Beach, FL - Image 42255 Cypress Drive Santa Rosa Beach, FL - Image 43255 Cypress Drive Santa Rosa Beach, FL - Image 44255 Cypress Drive Santa Rosa Beach, FL - Image 45255 Cypress Drive Santa Rosa Beach, FL - Image 46255 Cypress Drive Santa Rosa Beach, FL - Image 47255 Cypress Drive Santa Rosa Beach, FL - Image 48255 Cypress Drive Santa Rosa Beach, FL - Image 49255 Cypress Drive Santa Rosa Beach, FL - Image 50255 Cypress Drive Santa Rosa Beach, FL - Image 51255 Cypress Drive Santa Rosa Beach, FL - Image 52255 Cypress Drive Santa Rosa Beach, FL - Image 53255 Cypress Drive Santa Rosa Beach, FL - Image 54255 Cypress Drive Santa Rosa Beach, FL - Image 55255 Cypress Drive Santa Rosa Beach, FL - Image 56255 Cypress Drive Santa Rosa Beach, FL - Image 57255 Cypress Drive Santa Rosa Beach, FL - Image 58255 Cypress Drive Santa Rosa Beach, FL - Image 59255 Cypress Drive Santa Rosa Beach, FL - Image 60255 Cypress Drive Santa Rosa Beach, FL - Image 61255 Cypress Drive Santa Rosa Beach, FL - Image 62255 Cypress Drive Santa Rosa Beach, FL - Image 63255 Cypress Drive Santa Rosa Beach, FL - Image 64255 Cypress Drive Santa Rosa Beach, FL - Image 65255 Cypress Drive Santa Rosa Beach, FL - Image 66255 Cypress Drive Santa Rosa Beach, FL - Image 67255 Cypress Drive Santa Rosa Beach, FL - Image 68255 Cypress Drive Santa Rosa Beach, FL - Image 69255 Cypress Drive Santa Rosa Beach, FL - Image 70255 Cypress Drive Santa Rosa Beach, FL - Image 71255 Cypress Drive Santa Rosa Beach, FL - Image 72255 Cypress Drive Santa Rosa Beach, FL - Image 73255 Cypress Drive Santa Rosa Beach, FL - Image 74255 Cypress Drive Santa Rosa Beach, FL - Image 75255 Cypress Drive Santa Rosa Beach, FL - Image 76255 Cypress Drive Santa Rosa Beach, FL - Image 77255 Cypress Drive Santa Rosa Beach, FL - Image 78255 Cypress Drive Santa Rosa Beach, FL - Image 79255 Cypress Drive Santa Rosa Beach, FL - Image 80255 Cypress Drive Santa Rosa Beach, FL - Image 81

$1,750,000

5 Beds 5 Baths 3,217 SQFT 0.00 Acres
Type: Single Family

255 Cypress Drive
Santa Rosa Beach, FL 32459

MLS#: 995769
Brandon Hubbard
Brandon Hubbard
Brett/Robinson | Florida Real Estate
Phone: 251.269.0311
Office: 251.981.6180
Presented by: EXP Realty LLC

Property Description

 

NOW OFFERED AT $1,750,000 -- AN ADDITIONAL $140,000 PRICE REDUCTION! This remarkable price adjustment presents an exceptional opportunity to own one of Cypress Dunes' most scenic and elevated homes at an incredible value. The new price allows buyers the flexibility to update the bathrooms, refresh the interior with today's preferred neutral colors, and personalize the home to their own taste--all while securing one of the community's most coveted locations with extraordinary Gulf views that simply cannot be replicated. 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!


 

Interior Features

Bathrooms

Total Baths5

Other Interior Features

Air Conditioning Y/NYes
FlooringFloor Tile, Floor Vinyl
Furnished Y/NFurnished - All
Heating Y/NYes
Interior AmenitiesBreakfast Bar, Kitchen Island, Lighting Recessed, Owner's Closet, Pantry, Washer/Dryer Hookup, Woodwork Painted
Window FeaturesWindow Treatment All

General

Architectural StyleBeach House
Association Fee IncludesAccounting, Ground Keeping, Land Recreation, Legal, Management, Recreational Faclty, Security, Trash
Attached Garage Yes
Buyer FinancingConventional
Carport Y/NNo
CitySanta Rosa Beach
Community FeaturesShort Term Rental - Allowed, Pickle Ball, Community Room, Elevators, Exercise Room, Gated Community, Handicap Provisions, Pool, Tennis, TV Cable, Whirlpool
CoolingCeiling Fans, Central Air
CountyWalton
DirectionsFrom 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.
Elementary SchoolVan R Butler
Energy EfficientDoors
Garage Spaces2
HOAYes
HeatingCentral
High SchoolSouth Walton
Lot Size UnitsAcres
MLS Area17 - 30A West
MLS Area Minor1701 - Santa Rosa Beach S of 98 West of 393
Middle/Junior High SchoolEmerald Coast
New ConstructionNo
Patio/Porch FeaturesDeck Covered
Property ConditionConstruction Complete
Property SubtypeDetached Single Family
Property TypeResidential
SewerPublic Sewer
Standard StatusActive
StatusActive
Stories Count3
Subdivision NameCYPRESS DUNES
Tax Assessed Value$1,200
Tax Year2025
Total Rooms15
UtilitiesElectric, Gas - Natural, Public Water, TV Cable, Underground
ViewGulf
Year Built2006
ZoningResid Single Family

Exterior

Building Area Total3,217 sqft
Exterior AmenitiesBalcony, BBQ Pit/Grill, Columns, Sprinkler System
Foundation DetailsSlab
Lot Dimensions50/89/20/89
Lot FeaturesCovenants, See Remarks
Parking FeaturesGarage, Oversized
Road Surface TypePaved
Total Parking4

Additional Details

Price History

Schools 

Elementary School Van R Butler Elementary School

  

Similar Properties

$1,750,000

5 Beds 5 Baths 3,217 SQFT 0.00 Acres
Type: Single Family

255 Cypress Drive
Santa Rosa Beach, FL 32459

MLS#: 995769
Brandon Hubbard
Brandon Hubbard
Brett/Robinson | Florida Real Estate
Phone: 251.269.0311
Office: 251.981.6180