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$1,949,000

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 5 Full Baths
  • 3,217 Sq. Ft.
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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! 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!

Full Property Details for 255 Cypress Dr

General

  • Price: $1,949,000
  • Taxes: $14,012 (2025)
  • Status: Active
  • Type: Single Family
  • Source: Emerald_Coast
  • MLS ID: 995769
  • Updated: 5/4/2026
  • Added to Site: 96 day(s) ago

Rental Information

  • Complex Features: Short Term Rental - Allowed, Pickle Ball, Community Room, Elevators, Exercise Room, Gated Community, Handicap Provisions, Pool, Tennis, TV Cable, Whirlpool

Interior

  • Number of Rooms: 15
  • Interior Features: Breakfast Bar, Kitchen Island, Lighting Recessed, Owner's Closet, Pantry, Washer/Dryer Hookup, 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, Water Heater - Elect
  • Furnishings: Furnished - All
  • Flooring: Floor Tile, Floor Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 5

Bedrooms

  • Total Bedrooms: 5

Exterior

  • Exterior Features: Balcony, BBQ Pit/Grill, Columns, Sprinkler System
  • Porch/Patio/Deck: Deck Covered

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking Features: Garage, Oversized

Location

  • Area: 17 - 30A West
  • County: Walton
  • Subdivision: CYPRESS DUNES
  • Driving 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.

School Information

  • Elementary School: Van R Butler
  • Middle School: Emerald Coast
  • High School: South Walton

Community

  • Association: Yes
  • Assoc. Fees Include: Accounting, Ground Keeping, Land Recreation, Legal, Management, Recreational Faclty, Security, Trash

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Ceiling Fans, Central Air
  • Heating Type: Central
  • Heating/Cooling: Central, Ceiling Fans, Central Air

Utilities

  • Sewer: Public Sewer
  • Utility Description: Electric, Gas - Natural, Public Water, TV Cable, Underground

Structural Information

  • Architectural Style: Beach House
  • Stories/Levels: 3
  • Square Feet: 3,217
  • Sq. Ft. Source: Appraiser
  • Year Built: 2006

Lot Features

  • Property View: Gulf
  • Lot Dimensions: 50/89/20/89
  • Street/Road Desc.: Paved
  • Lot Features: Covenants, See Remarks
  • Zoning: Resid Single Family

Water Features

  • Water View: Yes

Green Features

  • Energy Efficient: Doors

Financial Considerations

  • Assessment Amount: $1,200
  • Tax Amount: $14,012.73
  • Tax Year: 2025

Disclosures and Reports

  • Special Conditions: Accept Backup Offers
  • Legal Description: LOT 33 CYPRESS DUNES PB 15-74 REPLAT PB 16-43 OR 2699-3849 OR 3400-611 OR 3220-1298
  • APN: 32-2S-20-33300-000-0330
  • Property ID: 32-2S-20-33300-000-0330

Listed by EXP Realty LLC

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Listing agent

— 255 Cypress Dr —

  • EXP Realty LLC

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 255 Cypress Dr

School District:Walton County School District
NameGradesDistance
Van R. Butler Elementary School
6694 West County Highway 30A, Santa Rosa Beach, FL 32459
K-50.5 mi
Emerald Coast Middle School
4019 US Highway 98 East, Santa Rosa Beach, FL 32459
6-89.3 mi
South Walton High School
645 Greenway Trail, Santa Rosa Beach, FL 32459
9-125.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 255 Cypress Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/04/2026
Price Reduced
$1,949,000
-2.5%
MLS
2/20/2026
Listed
$1,999,000
145.28%
MLS
3/08/2016
Sold
$815,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 255 Cypress Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$14,833
—
$1,550,818
-4%
2024
$14,833
-4%
$1,623,877
-8%
2023
$15,400
59%
$1,770,571
77%
2021
$9,677
-29%
$999,764
-32%
2022
$13,718
42%
$1,480,198
58%
2021
$9,677
9%
$939,275
5%
2019
$8,862
3%
$892,390
4%
2018
$8,595
4%
$861,951
3%
2017
$8,265
9%
$833,855
3%
2016
$7,602
8%
$811,621
9%
2015
$7,056
18%
$743,283
28%
2014
$5,995
-1%
$581,515
-1%
2013
$6,080
—
$586,084
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by EXP Realty LLC

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255 Cypress Drive, Santa Rosa Beach, FL 32459 (MLS# 995769) is a Single Family property with 5 bedrooms and 5 full bathrooms. 255 Cypress Drive is currently listed for $1,949,000 and was received on February 20, 2026. Want to learn more about 255 Cypress Drive? Do you have questions about finding other Single Family real estate for sale in Santa Rosa Beach? You can browse all Santa Rosa Beach real estate or contact a Coldwell Banker agent to request more information.

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