255 Cypress Dr

Santa Rosa Beach, FL 32459

$1,999,000
Price
5
Beds
3,217 Sq. Ft.
$621 / Sq. Ft.
3,217
Sq. Ft.
$621
per Sq. Ft.
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GORGEOUS PANOREMIC VIEWS FROM 3 LEVELS!
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a bedroom with a bed dresser and a window
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a view of a chair and table in the balcony
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a bathroom with a sink and a mirror
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a kitchen with stainless steel appliances kitchen island granite countertop a refrigerator and a stove top oven
a open kitchen with stainless steel appliances granite countertop a stove and a large window
a kitchen with stainless steel appliances granite countertop a sink a stove and a refrigerator
a kitchen with stainless steel appliances granite countertop a refrigerator a stove a sink and white cabinets with wooden floor
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a kitchen with stainless steel appliances granite countertop a stove a sink and a wooden floors
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a view of swimming pool with outdoor seating
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a living room with furniture
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Infinity Edge Pool
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a spacious bedroom with a bed a balcony with furniture and a fireplace
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Waterfall Pool
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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 very well maintained residence captures the beauty of the Gulf,...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 very well maintained residence captures the beauty of the Gulf, with expansive porches & 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 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!
  1. Listed by Shelley A Stipes • Brokerage DRE #no data • EXP Realty LLC
    P: (636)-578-1238 C: (636)-578-1238 shelley.stipes@exprealty.com

Property Details for 255 Cypress Drive

View
Gulf
Zoning
Resid Single Family
Architectural Style
Beach House
Subdivision Name
CYPRESS DUNES
LISTING UPDATED: 03/10/2026 12:34 PM

Property Details for 255 Cypress Drive

StatusActive
MLS #995769
Days on Market49
Taxes$14,013 / year
HOA Fees$1,250 / quarter
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Detached Single Family
Year Built2006
Lot Size50.00 AC / 2,178,000 SF
CountyWalton County
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Location

Listing Courtesy of EXP Realty LLC
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Building Information for 255 Cypress Drive

Stories3Year Built2006Building Size-Lot Size50.00 AC / 2,178,000 SF

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$11,650 per month

30 year fixed, 6.46% Interest

Principal and Interest

$10,066

Property Taxes

$1,168

HOA Dues

$417

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Property Information for 255 Cypress Drive

Summary
Location and General Information
  • Community Features: Short Term Rental - Allowed, Pickle Ball, Community Room, Elevators, Exercise Room, Gated Community, Handicap Provisions, Pool, Tennis, TV Cable, Whirlpool
  • 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.
  • MLS Area Minor: 1701 - Santa Rosa Beach S of 98 West of 393
  • MLS Area Major: 17 - 30A West
  • Latitude: 30.360641
  • Longitude: -86.269352
  • Location Tax and Legal:Sub Area: 1701 - Santa Rosa Beach S of 98 West of 393
  • Location Tax and Legal:Elementary School: Van R Butler
  • Location Tax and Legal:Middle School: Emerald Coast
  • Location Tax and Legal:High School: South Walton
  • Location Tax and Legal:Legal Description: LOT 33 CYPRESS DUNES PB 15-74 REPLAT PB 16-43 OR 2699-3849 OR 3400-611 OR 3220-1298
  • Project Facilities: Community Room, Elevators, Exercise Room, Gated Community, Handicap Provisions2, Pickle Ball, Pool2, Short Term Rental - Allowed, Tennis, TV Cable3, Whirlpool
  • Garage: true
Taxes and HOA
  • Association Fee Frequency: Quarterly
  • Association Fee Includes: Accounting, Ground Keeping, Land Recreation, Legal, Management, Recreational Faclty, Security, Trash
  • Association Fee2: $1,250
  • Tax Legal Description: LOT 33 CYPRESS DUNES PB 15-74 REPLAT PB 16-43 OR 2699-3849 OR 3400-611 OR 3220-1298
  • Parcel Number: 32-2S-20-33300-000-0330
  • Association Fee: $0
  • Association YN: Yes
  • Tax Annual Amount: $14,013
  • Listing Info Tax Legal:Last Taxes: $14,013
  • Listing Info Tax Legal:Last Tax Year: 2025.0
School Information
  • Elementary School: Van R Butler
  • Middle Or Junior School: Emerald Coast
  • High School: South Walton
Parking
  • Carport YN: No
  • Attached Garage YN: Yes
  • Parking Features: Garage, Oversized
  • Garage Spaces: 2.0
  • General Property Info:Driveway Spaces: 2.0
  • Parking Features: Garage3, Garage Attached, Oversized
Property
Lot Information
  • Building Area Source: Appraiser
  • Lot Size Dimensions: 50/89/20/89
  • Lot Size Units: Acres
  • Property Condition: Construction Complete
  • Lot Features: Covenants, See Remarks
  • Building Area Total: 3217.0
  • General Property Info:SqFt Source: Appraiser
  • Waterview: Gulf2
  • LotParcel Access: Paved Road
  • Lot Features: Covenants, See Remarks6
Property and Assessments
  • Road Surface Type: Paved
  • Tax Year: 2025.0
  • Floor Plans Count: 0.0
  • Property Type: Residential
  • Year Built: 2006.0
  • Property Sub Type: Detached Single Family
  • New Construction YN: No
  • General Property Info:Sub-Type: Detached Single Family
  • General Property Info:Design: Beach House
  • Listing Info Tax Legal:Homestead: false
  • Construction Status: Construction Complete
  • Construction Siding: Roof Metal, Slab
  • Occupancy Status: Occupied
Green Features
  • Green Energy Efficient: Doors
Utilities
  • Sewer: Public Sewer
  • Utilities: Electric, Gas - Natural, Public Water, TV Cable, Underground
  • Electric: True
  • 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
Interior and Exterior Features
Exterior Features
  • Exterior Features: Balcony, BBQ Pit/Grill, Columns, Sprinkler System
  • Foundation Details: Slab
  • Stories: 3.0
  • Patio And Porch Features: Deck Covered
  • General Property Info:Pool: No
  • General Property Info:Pool Type: None
  • Exterior: Balcony, BBQ PitGrill, Columns, Deck Covered, Sprinkler System
Interior Features
  • Heating: Central
  • Cooling: Ceiling Fans, Central Air
  • Interior Features: Breakfast Bar, Kitchen Island, Lighting Recessed, Owner's Closet, Pantry, Washer/Dryer Hookup, Woodwork Painted
  • Flooring: Floor Tile, Floor Vinyl
  • Window Features: Window Treatment All
  • Room Type: Master Bedroom, Master Bathroom, Office, Kitchen, Dining Room, Bedroom, Full Bathroom, Laundry, Garage
  • Rooms Total: 15.0
  • Bathrooms Total Integer: 5.0
  • Bathrooms Total Decimal: 5.0
  • Bathrooms Total Notational: 5.0
  • Cooling YN: Yes
  • Heating YN: Yes
  • Bedrooms Total: 5.0
  • Bathrooms Full: 5.0
  • Bathrooms Half: 0.0
  • Interior: Breakfast Bar, Floor Tile, Floor Vinyl, Furnished - All, Kitchen Island, Lighting Recessed, Owner's Closet, Pantry, WasherDryer Hookup, Window Treatment All, Woodwork Painted
  • Appliances: Auto Garage Door Opn, Dishwasher, Disposal, Dryer, Microwave, Oven Self Cleaning, Refrigerator WIceMk, Smoke Detector, StoveOven Gas, Washer, Wine Refrigerator
Room Information
Room 1
  • Room Type: Master Bedroom
  • Room Level: Third
  • Room Length: 22.0
  • Room Width: 14.0
  • Room Description: With added Coffee/Wine Bar
  • Room Dimensions: 22 x 14
Room 2
  • Room Type: Master Bathroom
  • Room Level: Third
  • Room Length: 20.0
  • Room Width: 9.0
  • Room Description: With Large Spa Shower
  • Room Dimensions: 20 x 9
Room 3
  • Room Type: Office
  • Room Level: Third
  • Room Length: 10.0
  • Room Width: 5.0
  • Room Description: Office Area
  • Room Dimensions: 10 x 5
Room 4
  • Room Type: Kitchen
  • Room Level: Second
  • Room Length: 14.0
  • Room Width: 9.0
  • Room Description: Large Center Island
  • Room Dimensions: 14 x 9
Room 5
  • Room Type: Dining Room
  • Room Level: Second
  • Room Length: 26.0
  • Room Width: 15.0
  • Room Description: Dining/Living Combo
  • Room Dimensions: 26 x 15
Room 6
  • Room Type: Bedroom
  • Room Level: Second
  • Room Length: 12.0
  • Room Width: 11.0
  • Room Dimensions: 12 x 11
Room 7
  • Room Type: Full Bathroom
  • Room Level: Second
  • Room Length: 8.0
  • Room Dimensions: 8 x 5
Room 8
  • Room Type: Bedroom
  • Room Level: Second
  • Room Length: 12.0
  • Room Width: 11.0
  • Room Dimensions: 12 x 11
Room 9
  • Room Type: Full Bathroom
  • Room Level: Second
  • Room Length: 8.0
  • Room Width: 7.0
  • Room Dimensions: 8 x 7
Room 10
  • Room Type: Bedroom
  • Room Level: First
  • Room Length: 13.0
  • Room Width: 11.0
  • Room Dimensions: 13 x 11
Room 11
  • Room Type: Full Bathroom
  • Room Level: First
  • Room Length: 11.0
  • Room Width: 5.0
  • Room Dimensions: 11 x 5
Room 12
  • Room Type: Bedroom
  • Room Level: First
  • Room Length: 13.0
  • Room Width: 11.0
  • Room Dimensions: 13 x 11
Multi Family
Multi Family Information
  • Furnished: Furnished - All
Rental
Rent Information
  • General Property Info:Immediate Occupancy: false
  • Listing Info Tax Legal:Is Subject Leased: false

Property History for 255 Cypress Drive

DateEvent & SourcePriceAppreciation
Feb 20, 2026

Listed (Active)

ECAR #995769

$1,999,000—
Dec 5, 2025

Withdrawn

ECAR #983913

$1,999,000—
Sep 23, 2025

Price Change

ECAR #983913

$2,100,000—
Sep 8, 2025

Listed (Active)

ECAR #983913

$2,200,000—
Mar 8, 2016

Sold (Public Record)

Public Record #567535784

$815,000

-1.2% / yr

Mar 8, 2016

Sold

ECAR #722464

$815,000—
Jan 26, 2016

Pending

ECAR #722464

—
Feb 4, 2015

Listed (Active)

ECAR #722464

$910,000—
Dec 6, 2014

Expired

ECAR #597767

$899,999—
May 30, 2013

Listed (Active)

ECAR #597767

$949,000—
May 26, 2013

Expired

ECAR #588054

$915,000—
Dec 11, 2012

Listed (Active)

ECAR #588054

$995,000—
Oct 27, 2009

Expired

ECAR #514957

—
Apr 21, 2009

Listed (Active)

ECAR #514957

$1,825,000—
Mar 30, 2009

Expired

ECAR #502907

—
Sep 29, 2008

Listed (Active)

ECAR #502907

$2,140,000—
Dec 1, 2005

Sold (Public Record)

Public Record #189917902

$925,000—
DateEvent & SourcePrice
02/20/2026

Listed (Active)

ECAR #995769

$1,999,000
12/05/2025

Withdrawn

ECAR #983913

$1,999,000
09/23/2025

Price Change

ECAR #983913

$2,100,000
09/08/2025

Listed (Active)

ECAR #983913

$2,200,000
03/08/2016

Sold (Public Record)

Public Record #567535784

$815,000

-1.2% / yr

03/08/2016

Sold

ECAR #722464

$815,000
01/26/2016

Pending

ECAR #722464

—
02/04/2015

Listed (Active)

ECAR #722464

$910,000
12/06/2014

Expired

ECAR #597767

$899,999
05/30/2013

Listed (Active)

ECAR #597767

$949,000
05/26/2013

Expired

ECAR #588054

$915,000
12/11/2012

Listed (Active)

ECAR #588054

$995,000
10/27/2009

Expired

ECAR #514957

—
04/21/2009

Listed (Active)

ECAR #514957

$1,825,000
03/30/2009

Expired

ECAR #502907

—
09/29/2008

Listed (Active)

ECAR #502907

$2,140,000
12/01/2005

Sold (Public Record)

Public Record #189917902

$925,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 255 Cypress Drive

Taxable ValueLand$550,000Additions$1,000,818Total$1,550,818
Tax Record2024$14,833 ($1,236 / month)
Home Facts
Beds5Total Finished SqFt3,217 SqFtAbove Grade Finished SqFt3,217 SqFtStories3Lot Size3,790 SqFtStyleSingle Family ResidenceYear Built2006CountyWALTONAPN32-2S-20-33300-000-0330

Schools near 255 Cypress Drive

This home is within Walton.
Rating
School
Type
Grades
Distance
Van R. Butler Elementary School
Public - K to 5
Emerald Coast Middle School
Public - 6 to 8
South Walton High School
Public - 9 to 12
Seaside Neighborhood School
Charter - 5 to 12
Rating
School
Distance
Van R. Butler Elementary School
PublicK to 5

Emerald Coast Middle School
Public6 to 8

South Walton High School
Public9 to 12

Seaside Neighborhood School
Charter5 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 255 Cypress Drive, Santa Rosa Beach, FL 32459

255 Cypress Drive is a single family home for sale in Santa Rosa Beach, FL 32459. This property was listed for sale on February 20, 2026 by EXP Realty LLC, it's currently listed at $1,999,000. It has been on the market for a total of 49 days and was last sold on March 8, 2016. This listing's school district is Walton. Nearby schools include Van R. Butler Elementary School, Emerald Coast Middle School and South Walton High School. 255 Cypress Drive is a 5-bed, 5-bath, 3,217 sqft single family home built in 2006.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of EXP Realty LLC

The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the Emerald Coast Association of REALTORS, Central Panhandle Association of REALTORS, Pensacola Association of REALTORS and Capital Area Technology & REALTOR Services. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Information deemed reliable but not guaranteed. Copyright© 2026 Emerald Coast Association of REALTORS, Central Panhandle Association of REALTORS, Pensacola Association of REALTORS and Capital Area Technology & REALTOR Services. All Rights Reserved.