255 Cypress Drive

3 Stories w/Coastal Gulf Views!
PANOREMIC VIEWS FROM 2ND FLOOR BALCONY
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GORGEOUS PANOREMIC VIEWS FROM 3 LEVELS!
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MORE GULF VIEWS!
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Infinity Edge Pool
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Waterfall Pool
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Active
$1,750,000
5 beds3,217 sqft
255 Cypress Dr, Santa Rosa Beach, FL 32459
Est: $10,211/moGet pre-approved
Single FamilyProperty Type
50 acresLot Size
2006Year Built
$544/sq ftPrice per sq ft
4 carsParking Spaces

Description

Now offered at $1,750,000 -- an additional $140,000 price reduction! This remarkable price adjustment presents an exceptional opportunity to own one of Cypress Dunes' most scenic and elevated homes at an incredible value. The new price allows buyers the flexibility to update the bathrooms, refresh the interior with today's preferred neutral colors, and personalize the home to their own taste--all while securing one of the community's most coveted locations with extraordinary Gulf views that simply...Now offered at $1,750,000 -- an additional $140,000 price reduction! This remarkable price adjustment presents an exceptional opportunity to own one of Cypress Dunes' most scenic and elevated homes at an incredible value. The new price allows buyers the flexibility to update the bathrooms, refresh the interior with today's preferred neutral colors, and personalize the home to their own taste--all while securing one of the community's most coveted locations with extraordinary Gulf views that simply cannot be replicated. Experience coastal living at its absolute finest in this extraordinary three-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 and elevated living spaces 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 difficult to find.
212 days on Market
  • Listed by: Shelley A Stipes 636.578.1238 shelley.stipes@exprealty.com Brokerage DRE #no data • EXP Realty LLC
Last updated: 09/09/2026 05:37 PM • Source: ECAR, MLS#: 995769

Location

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

Property Details
  • Taxes: $14,013 / year
  • MLS Type: Residential / Detached Single Family
  • County: Walton County
  • View: Gulf
  • Zoning: Resid Single Family
  • Architectural Style: Beach House
  • Subdivision Name: CYPRESS DUNES
Building Information
  • Stories: 3
  • Year Built: 2006
  • Lot Size: 50.00 AC / 2,178,000 SF
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 Includes: Accounting, Ground Keeping, Land Recreation, Legal, Management, Recreational Faclty, Security, Trash
  • 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
  • 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
  • Property Type Label: Residential
  • 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
  • Roof: Roof Metal
  • 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
  • Kitchen 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
  • 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
  • Furnished: Furnished - All
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
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
Jun 29, 2026

Price Change

ECAR #995769

$1,750,000—
May 28, 2026

Price Change

ECAR #995769

$1,890,000—
May 4, 2026

Price Change

ECAR #995769

$1,949,000—
DateEvent & SourcePrice
06/29/2026

Price Change

ECAR #995769

$1,750,000
05/28/2026

Price Change

ECAR #995769

$1,890,000
05/04/2026

Price Change

ECAR #995769

$1,949,000

For completeness, we 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 $1,750,000. It has been on the market for a total of 212 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 any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. 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.