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For sale
  • Price cut: $140K (6/29)
    $1,750,000

    255 Cypress Dr, Santa Rosa Beach, FL 32459

    5beds
    3,217sqft
    : 
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    Single Family Residence
    Built in 2006
    -- sqft lot
    $-- Zestimate®
    $544/sqft
    $-- HOA

    What's special

    Panoramic gulf viewsBreathtaking gulf viewsThree-story turn-key beach retreatBeautifully maintained residenceThree-story layoutExpansive porchesExtraordinary gulf views
    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. Whether as a primary residence, luxury second home, or investment property with outstanding rental potential, this is a rare opportunity to own one of Cypress Dunes' premier view properties at an exceptional price. Cosmetic updates can always be made--but a location and Gulf views like these are truly irreplaceable. 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!
    133 days
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    516
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    28
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    Zillow last checked:

    Listing updated:

    Listed by:

    Shelley A Stipes 636-578-1238,

    EXP Realty LLC

    Source: ECAOR,MLS#: 995769MLS Logo

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 5
      • Full bathrooms: 5
      Primary bedroom
      • Description: With added Coffee/Wine Bar
      • Level: Third
      • Area: 308 Square Feet
      • Dimensions: 22 x 14
      Bedroom
      • Level: Second
      • Area: 132 Square Feet
      • Dimensions: 12 x 11
      Bedroom
      • Level: Second
      • Area: 132 Square Feet
      • Dimensions: 12 x 11
      Bedroom
      • Level: First
      • Area: 143 Square Feet
      • Dimensions: 13 x 11
      Bedroom
      • Level: First
      • Area: 143 Square Feet
      • Dimensions: 13 x 11
      Primary bathroom
      • Description: With Large Spa Shower
      • Level: Third
      • Area: 180 Square Feet
      • Dimensions: 20 x 9
      Bathroom
      • Level: Second
      • Area: 40 Square Feet
      • Dimensions: 8 x 5
      Bathroom
      • Level: Second
      • Area: 56 Square Feet
      • Dimensions: 8 x 7
      Bathroom
      • Level: First
      • Area: 55 Square Feet
      • Dimensions: 11 x 5
      Bathroom
      • Level: First
      • Area: 40 Square Feet
      • Dimensions: 10 x 4
      Dining room
      • Description: Dining/Living Combo
      • Level: Second
      • Area: 390 Square Feet
      • Dimensions: 26 x 15
      Garage
      • Description: Oversized
      • Level: First
      • Area: 494 Square Feet
      • Dimensions: 26 x 19
      Kitchen
      • Description: Large Center Island
      • Level: Second
      • Area: 126 Square Feet
      • Dimensions: 14 x 9
      Laundry
      • Description: New Front Load Washer & Dryer
      • Level: First
      • Area: 77 Square Feet
      • Dimensions: 11 x 7
      Office
      • Description: Office Area
      • Level: Third
      • Area: 50 Square Feet
      • Dimensions: 10 x 5
      Heating
      • Central, Natural Gas
      Cooling
      • Central Air, Ceiling Fan(s)
      Appliances
      • Included: Dishwasher, Disposal, Dryer, Microwave, Washer, Electric Water Heater
      • Laundry: Washer/Dryer Hookup
      Features
      • Breakfast Bar, Kitchen Island, Recessed Lighting, Owner's Closet, Pantry, Woodwork Painted
      • Flooring: Tile, Vinyl
      • Windows: Window Treatments
      • Furnished: Yes
      • Common walls with other units/homes: No Common Walls
      Interior area
      • Total structure area: 3,217
      • Total interior livable area: 3,217 sqft

      Property

      Parking
      • Total spaces: 4
      • Parking features: Garage Door Opener, Oversized, Garage
      • Attached garage spaces: 2
      Features
      • Stories: 3
      • Patio & porch: Covered
      • Exterior features: Outdoor Grill, Balcony, Columns, Sprinkler System
      • Has view: Yes
      • View description: Gulf
      • Has water view: Yes
      • Water view: Gulf
      Lot
      • Dimensions: 50/89/20/89
      • Features: Covenants, See Remarks
      Details
      • Parcel number: 322S20333000000330
      • Zoning description: Resid Single Family
      • Special conditions: Accept Backup Offers

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Beach House
      • Property subtype: Single Family Residence
      Materials
      • Foundation: Slab
      • Roof: Metal
      Condition
      • Construction Complete
      • New construction: No
      • Year built: 2006

      Utilities & green energy

      • Water: Public
      Green energy
      • Energy efficient items: Doors

      Community & HOA

      Community
      • Features: Community Room, Elevators, Fitness Center, Gated, Handicap Provisions, Pool, TV Cable, Tennis Court(s), Whirlpool, Pickleball, Short Term Rental - Allowed
      • Security: Smoke Detector(s)
      • Subdivision: CYPRESS DUNES
      HOA
      • Has HOA: Yes
      • Services included: Maintenance Grounds, Land Recreation, Legal, Management, Recreational Faclty, Security, Trash
      Location
      • Region: Santa Rosa Beach

      Financial & listing details

      • Price per square foot: $544/sqft
      • Tax assessed value: $1,550,818
      • Annual tax amount: $14,012
      • Date on market: 2/20/2026
      • Road surface type: Paved

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        6/29/2026Price change$1,750,000-7.4%$544/sqft
        Source: ECAOR #995769 Report a problem
        5/29/2026Price change$1,890,000-3%$588/sqft
        Source: ECAOR #995769 Report a problem
        5/4/2026Price change$1,949,000-2.5%$606/sqft
        Source: ECAOR #995769 Report a problem
        2/20/2026Listed for sale$1,999,000$621/sqft
        Source: eXp Realty #995769 Report a problem
        12/5/2025Listing removed$1,999,000$621/sqft
        Source: ECAOR #983913 Report a problem
        11/14/2025Price change$1,999,000-4.8%$621/sqft
        Source: ECAOR #983913 Report a problem
        9/23/2025Price change$2,100,000-4.5%$653/sqft
        Source: ECAOR #983913 Report a problem
        9/8/2025Listed for sale$2,200,000+169.9%$684/sqft
        Source: ECAOR #983913 Report a problem
        3/8/2016Sold$815,000-4.7%$253/sqft
        Source: Forgotten Coast Realtor Association #256181 Report a problem
        3/3/2016Pending sale$855,000$266/sqft
        Source: Better Homes and Gardens Real Estate Emerald Coast #722464 Report a problem
        9/2/2015Price change$855,000-6%$266/sqft
        Source: Better Homes and Gardens Real Estate Emerald Coast #722464 Report a problem
        6/3/2015Pending sale$910,000$283/sqft
        Source: Better Homes and Gardens Real Estate Emerald Coast #722464 Report a problem
        2/6/2015Listed for sale$910,000+1.1%$283/sqft
        Source: Better Homes and Gardens Real Estate Emerald Coast #722464 Report a problem
        12/6/2014Listing removed$899,999$280/sqft
        Source: 30A Local Properties #597767 Report a problem
        3/4/2014Listed for sale$899,999-9.5%$280/sqft
        Source: 30A Local Properties Inc #597767 Report a problem
        1/16/2013Listing removed$994,500$309/sqft
        Source: Military For Sale by Owner #40459 Report a problem
        12/14/2012Price change$994,500-0.1%$309/sqft
        Source: FlatFee.com #3259 Report a problem
        12/12/2012Price change$995,000+2.1%$309/sqft
        Source: FlatFee.com #3259 Report a problem
        5/19/2012Price change$975,000-99%$303/sqft
        Source: Owner Report a problem
        5/9/2012Price change$97,500,000+8025%$30,308/sqft
        Source: Owner Report a problem
        1/12/2012Price change$1,200,000-7.6%$373/sqft
        Source: Owner Report a problem
        9/29/2011Listed for sale$1,299,000-39.3%$404/sqft
        Source: Owner Report a problem
        4/2/2009Listing removed$2,140,000$665/sqft
        Source: Prudential Real Estate #502907 Report a problem
        10/14/2008Listed for sale$2,140,000+131.4%$665/sqft
        Source: Prudential Real Estate #502907 Report a problem
        12/1/2005Sold$925,000$288/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$14,013 -5.5%$1,550,818 -4.5%
        2024$14,833 -3.7%$1,623,877 -0.3%
        2023$15,400 +12.3%$1,628,218 +10%
        2022$13,718 +41.7%$1,480,198 +48.1%
        2021$9,677 +3.2%$999,764 +6.4%
        2020$9,376 +5.8%$939,275 +5.3%
        2019$8,862 $892,390 +3.5%
        2018$8,862 +3.1%$861,951 +3.4%
        2017$8,595 +4%$833,855 +2.7%
        2016$8,265 +8.7%$811,621 +9.2%
        2015$7,602 +7.7%$743,283 +27.8%
        2014$7,056 $581,515 -0.8%
        2013-- $586,084 +3%
        2012-- $568,834 -5.8%
        2011-- $603,834 +4.5%
        2010-- $578,036 -24.3%
        2009-- $763,437 -32.3%
        2008-- $1,128,140 -12.6%
        2007-- $1,291,465 +68.8%
        2005-- $765,000 +11050%
        2004-- $6,861

        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 32459

        Getting around

        8 / 100
        Car-Dependent
        30 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Van R Butler
        • Middle: Emerald Coast
        • High: South Walton

        Source: ECAOR. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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