255 Cypress Drive, Santa Rosa Beach, FL 32459
$1,949,000
Property Type:
Residential
Bedrooms:
5
Baths:
5
Square Footage:
3,217
Status:
Active
Current Price:
$1,949,000
List Date:
2/20/2026
Last Modified:
5/04/2026
Description
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!
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!
More Information MLS# 995769
General Property Info
Sub-Type: Detached Single Family
Design: Beach House
SqFt Source: Appraiser
Immediate Occupancy: No
Garage: Yes
Carport: No
Driveway Spaces: 2
Pool: No
Pool Type: None
Apx SqFt(Htd/Cooled): 3217
Bedrooms: 5
Full Baths: 5
Total Bathrooms: 5
# Stories: 3
Year Built: 2006
Garage Spaces: 2
Contract Info
Listing Board: Emerald Coast
List Price/SqFt: 605.84
List Date: 2026-02-18
Current Price: $1,949,000
List Price: $1,949,000
Location, Tax and Legal
Sub Area: 1701 - Santa Rosa Beach S of 98 West of 393
Elementary School: Van R Butler
Middle School: Emerald Coast
High School: South Walton
Legal Description: LOT 33 CYPRESS DUNES PB 15-74 REPLAT PB 16-43 OR 2699-3849 OR 3400-611 OR 3220-1298
Listing Info, Tax & Legal
Homestead: No
Is Subject Leased: No
Assessment Fees: Yes
Assessment Amount: 1200
Annual Assessment Amount: 4800
Assessment Paid: Quarterly
New Buyer Fee: Yes
New Buyer Fee Amt: 0.25
New Buyer Fee Paid: %
Last Taxes: 14012.73
Last Tax Year: 2025
Brokerage Interest: No Interest
As Is: No
Remarks & Misc
Remarks: 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!
Sale Type
Accept Backup Offers: 1
Construction Status
Construction Complete: 1
Parking Features
Garage: 1
Garage Attached: 1
Oversized: 1
Waterview
Gulf: 1
Lot/Parcel Access
Paved Road: 1
Lot Features
Covenants: 1
See Remarks: 1
Project Facilities
Community Room: 1
Elevators: 1
Exercise Room: 1
Gated Community: 1
Handicap Provisions: 1
Pickle Ball: 1
Pool: 1
Short Term Rental - Allowed: 1
Tennis: 1
TV Cable: 1
Whirlpool: 1
Construction/Siding
Roof Metal: 1
Slab: 1
Utilities
Electric: 1
Gas - Natural: 1
Public Sewer: 1
Public Water: 1
TV Cable: 1
Underground: 1
Zoning
Resid Single Family: 1
Exterior
Balcony: 1
BBQ Pit/Grill: 1
Columns: 1
Deck Covered: 1
Sprinkler System: 1
Interior
Breakfast Bar: 1
Floor Tile: 1
Floor Vinyl: 1
Furnished - All: 1
Kitchen Island: 1
Lighting Recessed: 1
Owner's Closet: 1
Pantry: 1
Washer/Dryer Hookup: 1
Window Treatment All: 1
Woodwork Painted: 1
Financing
Conventional: 1
Appliances
Auto Garage Door Opn: 1
Dishwasher: 1
Disposal: 1
Dryer: 1
Microwave: 1
Oven Self Cleaning: 1
Refrigerator W/IceMk: 1
Smoke Detector: 1
Stove/Oven Gas: 1
Washer: 1
Wine Refrigerator: 1
Energy
AC - 2 or More: 1
AC - Central Elect: 1
Ceiling Fans: 1
Heat - Two or More: 1
Heat Cntrl Electric: 1
Insulated Doors: 1
Water Heater - Elect: 1
Mstr Bdrm/Mstr Bath
MBath Sauna/Steam: 1
MBath Shower Only: 1
MBath Tile: 1
MBath Walk-In Closet: 1
MBed Balcony: 1
MBed Sitting Area: 1
MBed Walk-in Closet: 1
MBed Waterfront: 1
Master Bedroom
Third: 1
Bedroom
First: 1
Second: 1
Kitchen
Second: 1
Full Bathroom
First: 1
Second: 1
Rooms
Bedroom: 1
Dining Room: 1
Full Bathroom: 1
Garage: 1
Kitchen: 1
Laundry: 1
Master Bathroom: 1
Master Bedroom: 1
Office: 1
Fees Include
Accounting: 1
Ground Keeping: 1
Land Recreation: 1
Legal: 1
Management: 1
Recreational Faclty: 1
Security: 1
Trash: 1
Status Change Info
Status: Active
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
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
Room Information
Master Bedroom
Level: Third
Dimensions: 22 x 14
Length: 22.00
Width: 14.00
Remarks: With added Coffee/Wine Bar
Dimensions: 22 x 14
Master Bathroom
Level: Third
Dimensions: 20 x 9
Length: 20.00
Width: 9.00
Remarks: With Large Spa Shower
Dimensions: 20 x 9
Office
Level: Third
Dimensions: 10 x 5
Length: 10.00
Width: 5.00
Remarks: Office Area
Dimensions: 10 x 5
Kitchen
Level: Second
Dimensions: 14 x 9
Length: 14.00
Width: 9.00
Remarks: Large Center Island
Dimensions: 14 x 9
Dining Room
Level: Second
Dimensions: 26 x 15
Length: 26.00
Width: 15.00
Remarks: Dining/Living Combo
Dimensions: 26 x 15
Bedroom
Level: Second
Dimensions: 12 x 11
Length: 12.00
Width: 11.00
Dimensions: 12 x 11
Full Bathroom
Level: Second
Dimensions: 8 x 5
Length: 8.00
Width: 5.00
Dimensions: 8 x 5
Bedroom
Level: Second
Dimensions: 12 x 11
Length: 12.00
Width: 11.00
Dimensions: 12 x 11
Full Bathroom
Level: Second
Dimensions: 8 x 7
Length: 8.00
Width: 7.00
Dimensions: 8 x 7
Bedroom
Level: First
Dimensions: 13 x 11
Length: 13.00
Width: 11.00
Dimensions: 13 x 11
Full Bathroom
Level: First
Dimensions: 11 x 5
Length: 11.00
Width: 5.00
Dimensions: 11 x 5
Bedroom
Level: First
Dimensions: 13 x 11
Length: 13.00
Width: 11.00
Dimensions: 13 x 11
Full Bathroom
Level: First
Dimensions: 10 x 4
Length: 10.00
Width: 4.00
Dimensions: 10 x 4
Laundry
Level: First
Dimensions: 11 x 7
Length: 11.00
Width: 7.00
Remarks: New Front Load Washer & Dryer
Dimensions: 11 x 7
Garage
Level: First
Dimensions: 26 x 19
Length: 26.00
Width: 19.00
Remarks: Oversized
Dimensions: 26 x 19
Listing Office:
EXP Realty LLC
Listing Agent:
Shelley A Stipes
Last Updated: May - 04 - 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.