Main Content

255 Cypress Drive, Santa Rosa Beach, FL 32459 (MLS# 995769)


$1,890,000
255 Cypress Drive
Santa Rosa Beach, FL 32459
MLS# 995769
5 beds  |  5 baths  |  3217 sqft


Your PANORAMIC Gulf View Coastal Escape Awaits!
  1 / 82  
Your PANORAMIC Gulf View Coastal Escape Awaits! GORGEOUS PANORAMIC GULF VIEWS FROM ALL 3 LEVELS, WITH EACH LEVEL OFFERING MORE GULF VIEWS! 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 First Level Laundry Room, NEW front load washer & dryer, utility sink and overhead storage cabinets 255 Cypress Drive, Santa Rosa Beach, FL 32459 First Level Entry Foyer 255 Cypress Drive, Santa Rosa Beach, FL 32459 First Level 1st Guest Bedroom with Full Bath 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 First Level 2nd Guest Bedroom with Full Bath 255 Cypress Drive, Santa Rosa Beach, FL 32459 First Level Porch overlook Topsail Preserve 255 Cypress Drive, Santa Rosa Beach, FL 32459 Main Level 3rd Guest Bedroom with Full Bath 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 Main Level 4th Guest Bedroom with Full Bath 255 Cypress Drive, Santa Rosa Beach, FL 32459 Main Level Covered Porch 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 Main Level Kitchen featuring wine cooler and NEW 2025 side-by-side stainless steel refrigerator Main Level Kitchen, Dining and Living Rooms 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 Spacious Open Concept Living Area 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 Main Level Dining Room with added seating space at Center Island 255 Cypress Drive, Santa Rosa Beach, FL 32459 Main Level Center Island Seating 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 Peaceful Covered Porch with Gulf Views 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 Third Level Office Area Breathtaking Gulf views from 3rd Story Primary Bedroom Suite Balcony! 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 Primary Bedroom Coffee/Wine Bar 255 Cypress Drive, Santa Rosa Beach, FL 32459 Large Walk-In Primary Bedroom Closet Spacious Primary Bathroom Deluxe Spa Shower 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 Amenity Center, a short walk from property. Breathtaking infinity edge pool with Gulf views! 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 featuring infinity edge pool 255 Cypress Drive, Santa Rosa Beach, FL 32459 Covered seating area with fireplace Indoor recreation area Spa Hot Tub 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 Workout Gym Phase 2 Waterfall Pool 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459 255 Cypress Drive, Santa Rosa Beach, FL 32459

Property Description
NOW OFFERED WITH A SIGNIFICANT $109,000 TOTAL PRICE REDUCTION, presenting an exceptional opportunity for buyers to own one of Cypress Dunes' most scenic and elevated properties at an incredible value. Whether as a primary residence, luxury second home, or investment property, this is a rare chance to secure premier coastal living with unmatched views and timeless appeal. 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 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 & elevated vantage points showcasing emerald waters, endless horizons & 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 to find.

Details
Maps
Status Change Info
Status: Active
Contract Info
List Date: 2026-02-18
Current Price: $1,890,000
List Price: $1,890,000
List Price/SqFt: 587.5
Listing Board: Emerald Coast
Location Tax and Legal
Area: 17 - 30A West
Street #: 255
Street Name: Cypress
Street Suffix: Drive
State: FL
Zip Code: 32459
County: Walton
Project Name/Subdivision: CYPRESS DUNES
Parcel ID: 32-2S-20-33300-000-0330
General Property Info
Sub-Type: Detached Single Family
Design: Beach House
Apx SqFt(Htd/Cooled): 3217
SqFt Source: Appraiser
Bedrooms: 5
Full Baths: 5
Total Bathrooms: 5
# Stories: 3
Year Built: 2006
Immediate Occupancy: No
Garage: Yes
Carport: No
Garage Spaces: 2
Driveway Spaces: 2
userdefined76: 4
Pool: No
Pool Type: None
Property Features
Sale Type: Accept Backup Offers
Construction Status: Construction Complete
Lot Features: Covenants; See Remarks
Zoning: Resid Single Family
Waterview: Gulf
Parking Features: Garage; Garage Attached; Oversized
Project Facilities: Community Room; Elevators; Exercise Room; Gated Community; Handicap Provisions; Pickle Ball; Pool; Short Term Rental - Allowed; Tennis; TV Cable; Whirlpool
Exterior: Balcony; BBQ Pit/Grill; Columns; Deck Covered; Sprinkler System
Interior: Breakfast Bar; Floor Tile; Floor Vinyl; Furnished - All; Kitchen Island; Lighting Recessed; Owner's Closet; Pantry; Washer/Dryer Hookup; Window Treatment All; Woodwork Painted
Appliances: Auto Garage Door Opn; Dishwasher; Disposal; Dryer; Microwave; Oven Self Cleaning; Refrigerator W/IceMk; Smoke Detector; Stove/Oven Gas; Washer; Wine Refrigerator
Utilities: Electric; Gas - Natural; Public Sewer; Public Water; TV Cable; Underground
Energy: AC - 2 or More; AC - Central Elect; Ceiling Fans; Heat - Two or More; Heat Cntrl Electric; Insulated Doors; Water Heater - Elect
Master Bedroom: Third
Bedroom: First; Second
Kitchen: Second
Full Bathroom: First; Second
Rooms: Bedroom; Dining Room; Full Bathroom; Garage; Kitchen; Laundry; Master Bathroom; Master Bedroom; Office
Financing: Conventional
Fees Include: Accounting; Ground Keeping; Land Recreation; Legal; Management; Recreational Faclty; Security; Trash
Supplements
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!
Room Information
Room Name Level Dimensions Length Width Remarks Dimensions
Master BedroomThird22 x 1422.0014.00With added Coffee/Wine Bar22 x 14
Master BathroomThird20 x 920.009.00With Large Spa Shower20 x 9
OfficeThird10 x 510.005.00Office Area10 x 5
KitchenSecond14 x 914.009.00Large Center Island14 x 9
Dining RoomSecond26 x 1526.0015.00Dining/Living Combo26 x 15
BedroomSecond12 x 1112.0011.0012 x 11
Full BathroomSecond8 x 58.005.008 x 5
BedroomSecond12 x 1112.0011.0012 x 11
Full BathroomSecond8 x 78.007.008 x 7
BedroomFirst13 x 1113.0011.0013 x 11
Full BathroomFirst11 x 511.005.0011 x 5
BedroomFirst13 x 1113.0011.0013 x 11
Full BathroomFirst10 x 410.004.0010 x 4
LaundryFirst11 x 711.007.00New Front Load Washer & Dryer11 x 7
GarageFirst26 x 1926.0019.00Oversized26 x 19

Listing Office: EXP Realty LLC

Last Updated: May - 29 - 2026

All information is believed to be accurate but is not guaranteed. Protected by Copyright© 2026 and is owned either by the Emerald Coast Association of REALTORS®, Inc or by the developers of the software, FBS, Inc. All rights reserved.