Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$1,999,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 5 Full Baths
  • 3,217 Sq. Ft.
  • Updated 4 hours ago
See This Home
Save This Home
See This Home
Save This Home
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!

Full Property Details for 255 Cypress Dr

General

  • Price: $1,999,000
  • Taxes: $14,012 (2025)
  • Status: Active
  • Type: Single Family
  • Source: Emerald_Coast
  • MLS ID: 995769
  • Updated: Today (2/20/2026)
  • Added to Site: Today

Interior

  • Rooms/Areas: Bedroom, Dining Room, Full Bathroom, Garage, Kitchen, Laundry, Master Bathroom, Master Bedroom, Office
  • Interior Features: 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

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 5

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Kitchen: Kitchen
  • Dining Room: Dining Room
  • Office: Office

Additional Information

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

Exterior

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

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking: Garage, Garage Attached, 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

Heating & Cooling

  • Heating/Cooling: AC - 2 or More, AC - Central Elect, Ceiling Fans, Heat - Two or More, Heat Cntrl Electric, Insulated Doors, Water Heater - Elect

Utilities

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

Structural Information

  • Architectural Style: Beach House
  • Construction: Roof Metal, Slab
  • 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 Road
  • Lot Features: Covenants, See Remarks
  • Zoning: Resid Single Family

Financial Considerations

  • Assessment Amount: $1,250
  • Assmt Payment Freq: Quarterly
  • Tax Amount: $14,012
  • Tax Year: 2025
  • Terms: Conventional

Disclosures and Reports

  • Legal Description: LOT 33 CYPRESS DUNES PB 15-74 REPLAT PB 16-43 OR 2699-3849 OR 3400-611 OR 3220-1298
  • Assessment: Yes
  • APN: 32-2S-20-33300-000-0330

Listed by EXP Realty LLC

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

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 Pitney Bowes 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
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.

Estimate the Cost for 255 Cypress Dr

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by EXP Realty LLC

Similar Properties near 255 Cypress Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

6192 W County Hwy 30A W, Santa Rosa Beach, FL 32459 - Photo 1
$1,995,000

6192 W County Hwy 30A W  Santa Rosa Beach, FL 32459

  • Single Family
  • Active
  • 5
    Beds
  • 5
    Total Baths
  • 2,597
    Sq. Ft.
180 Tang-O-Mar Dr, Miramar Beach, FL 32550 - Photo 1 Just Listed
$2,050,000

180 Tang-O-Mar Dr  Miramar Beach, FL 32550

  • Single Family
  • Active
  • Updated 1 day ago
  • 5
    Beds
  • 5
    Total Baths
  • 3,048
    Sq. Ft.
181 Plantation Cir, Santa Rosa Beach, FL 32459 - Photo 1
$1,900,000

181 Plantation Cir  Santa Rosa Beach, FL 32459

  • Single Family
  • Active
  • Updated 3 days ago
  • 5
    Beds
  • 5
    Total Baths
  • 3,645
    Sq. Ft.
220 N Saint Francis Dr N, Miramar Beach, FL 32550 - Photo 1
$1,985,000

220 N Saint Francis Dr N  Miramar Beach, FL 32550

  • Single Family
  • Active
  • 5
    Beds
  • 4
    Total Baths
  • 3,136
    Sq. Ft.

Just Listed near 255 Cypress Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

107 Holley Grv Ln, Point Washington, FL 32459 - Photo 1 Just Listed
$478,900

107 Holley Grv Ln  Point Washington, FL 32459

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,856
    Sq. Ft.
9800 Grand Sandestin Blvd, Miramar Beach, FL 32550 - Photo 1 Just Listed
$289,000

9800 Grand Sandestin Blvd  #UNIT 5109  Miramar Beach, FL 32550

  • Condo / Townhouse
  • Active
  • Updated 18 hours ago
  • 1
    Bed
  • 1
    Total Bath
  • 772
    Sq. Ft.
Listed by Michael Tomlin (850) 499-2432
5000 S Sandestin Blvd S, Miramar Beach, FL 32550 - Photo 1 Just Listed
$289,000

5000 S Sandestin Blvd S  #7505  Miramar Beach, FL 32550

  • Condo / Townhouse
  • Active
  • Updated 6 days ago
  • 1
    Total Bath
  • 469
    Sq. Ft.
732 Scenic Gulf Dr, Miramar Beach, FL 32550 - Photo 1 Just Listed
$699,900

732 Scenic Gulf Dr  #UNIT A401  Miramar Beach, FL 32550

  • Condo / Townhouse
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,324
    Sq. Ft.
Listed by Beycome of Florida LLC

Price Reduced near 255 Cypress Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

147 Holley Grove Ln, Point Washington, FL 32459 - Photo 1 Price Reduced
-$53,355 (-10.24%)
$467,900

147 Holley Grove Ln  Point Washington, FL 32459

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 2,108
    Sq. Ft.
353 Holley Grove Ln, Point Washington, FL 32459 - Photo 1 Price Reduced
-$5,000 (-1.04%)
$474,900

353 Holley Grove Ln  Point Washington, FL 32459

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 2,108
    Sq. Ft.
9800 Grand Sandestin Blvd, Miramar Beach, FL 32550 - Photo 1 Price Reduced
-$5,000 (-1.65%)
$298,750

9800 Grand Sandestin Blvd  #UNIT 5609  Miramar Beach, FL 32550

  • Condo / Townhouse
  • Active
  • Updated 20 hours ago
  • 1
    Bed
  • 1
    Total Bath
  • 772
    Sq. Ft.
152 S Driftwood Bay S, Miramar Beach, FL 32550 - Photo 1 Price Reduced
-$7,000 (-1%)
$692,700

152 S Driftwood Bay S  #UNIT 148  Miramar Beach, FL 32550

  • Condo / Townhouse
  • Active
  • Updated 6 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,040
    Sq. Ft.

Recent Sales near 255 Cypress Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

343 Cypress Dr, Santa Rosa Beach, FL 32459 - Photo 1 Sold
$1,750,000

343 Cypress Dr  Santa Rosa Beach, FL 32459

  • Single Family
  • Closed
  • Updated 2 days ago
  • 5
    Beds
  • 5
    Total Baths
  • 2,801
    Sq. Ft.
391 Cypress Dr, Santa Rosa Beach, FL 32459 - Photo 1 Sold
$1,775,000

391 Cypress Dr  Santa Rosa Beach, FL 32459

  • Single Family
  • Closed
  • 5
    Beds
  • 5
    Total Baths
  • 3,042
    Sq. Ft.
40 S Bishop Road S, Santa Rosa Beach, FL 32459 - Photo 1 Sold
$1,800,000

40 S Bishop Road S  Santa Rosa Beach, FL 32459

  • Vacant Land
  • Closed
  • 0.38
    Acres
129 Oyster Lake Dr, Santa Rosa Beach, FL 32459 - Photo 1 Sold
$1,850,000

129 Oyster Lake Dr  Santa Rosa Beach, FL 32459

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 3,350
    Sq. Ft.

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 $1,999,000 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.

Tour this property