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For sale
    • $2,995,000

    85 Trailhead Dr, Watersound, FL 32461

    5beds
    4,394sqft
    : 
    $18,495/mo
    Get pre-qualified
    Single Family Residence
    Built in 2020
    0.27 Acres Lot
    $-- Zestimate®
    $682/sqft
    $-- HOA

    What's special

    Wraparound porchWell-appointed guest suiteSummer kitchenExpansive custom closetCustom cabinetryPremium appliancesDetached carriage house
    Where luxury meets effortless coastal living, this 4,394-square-foot custom residence unfolds with a quiet confidence, where every detail has been thoughtfully considered and every space invites you to slow down and stay awhile. From the moment you arrive, the wraparound porch sets the tone, offering a warm, welcoming introduction that feels both refined and relaxed. Inside, natural light pours through expansive windows, illuminating soaring ceilings and a seamless, open-concept design. The kitchen anchors the home as both a gathering place and a showpiece, outfitted with premium appliances, custom cabinetry, and a generously sized butler's pantry that keeps everything effortlessly within reach while maintaining a clean, elevated aesthetic. The main level offers a well-appointed guest suite, creating a private and comfortable space for visitors, while the rest of the home unfolds with an easy, intuitive flow designed for both everyday living and entertaining. Just beyond the doors, the backyard transforms into a private retreat. Fully fenced and backing to a serene wooded setting, the outdoor space feels tucked away and protected. A saltwater pool becomes the centerpiece, complemented by a summer kitchen and a covered lounge with a fireplace, where evenings linger a little longer and gatherings come together with ease. Upstairs, the primary suite is designed as a true escape, where mornings begin softly and evenings wind down in a spa-inspired bath and expansive custom closet. Additional guest rooms, a charming balcony, and a detached carriage house offer flexibility for hosting, working, or simply creating space to spread out. Set within Watersound Origins, the home is part of a community that balances natural beauty with thoughtful design, offering access to golf, dining, and the nearby beaches of 30A. It's a place where the pace feels just right, and where everyday living carries a sense of ease, intention, and understated luxury.
    135 days
    |
    415
    |
    19
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Dahler & Co. dahlerandco@scenicsir.com,

    Scenic Sotheby's International Realty

    Source: ECAOR,MLS#: 999707MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 6
      • Full bathrooms: 4
      • 1/2 bathrooms: 2
      Primary bedroom
      • Level: Second
      • Area: 263.2 Square Feet
      • Dimensions: 18.8 x 14
      Bedroom
      • Level: First
      • Area: 209.76 Square Feet
      • Dimensions: 13.11 x 16
      Bedroom
      • Level: Second
      • Area: 180.7 Square Feet
      • Dimensions: 13.9 x 13
      Bedroom
      • Level: Second
      • Area: 191.41 Square Feet
      • Dimensions: 13.11 x 14.6
      Primary bathroom
      • Level: Second
      • Area: 115.44 Square Feet
      • Dimensions: 7.4 x 15.6
      Bathroom
      • Level: First
      • Area: 28.62 Square Feet
      • Dimensions: 5.4 x 5.3
      Kitchen
      • Level: First
      • Area: 220 Square Feet
      • Dimensions: 11 x 20
      Living room
      • Level: First
      • Area: 522 Square Feet
      • Dimensions: 26.1 x 20
      Pantry
      • Level: First
      • Area: 99.64 Square Feet
      • Dimensions: 9.4 x 10.6
      Other
      • Level: Second
      • Area: 494.1 Square Feet
      • Dimensions: 27 x 18.3
      Heating
      • Natural Gas
      Cooling
      • Central Air
      Appliances
      • Included: Cooktop, Dishwasher, Disposal, Freezer, Microwave, Range Hood, Tankless Water Heater
      • Laundry: Washer/Dryer Hookup
      Features
      • Beamed Ceilings, Crown Molding, Vaulted Ceiling(s), Kitchen Island, Newly Painted, Owner's Closet, Wet Bar
      • Flooring: Hardwood
      • Has fireplace: Yes
      • Fireplace features: EPA Qualified Fireplace, Gas
      • Common walls with other units/homes: No Common Walls
      Interior area
      • Total structure area: 4,394
      • Total interior livable area: 4,394 sqft

      Property

      Parking
      • Total spaces: 8
      • Parking features: Garage Door Opener
      • Attached garage spaces: 2
      Features
      • Stories: 2
      • Patio & porch: Covered, Porch, Screened
      • Exterior features: Private Yard, Outdoor Shower, Sprinkler System, Outdoor Kitchen
      • Pool features: In Ground
      Lot
      • Size: 0.27 Acres
      • Dimensions: 99 x 120 x 66 x 152
      Details
      • Parcel number: 243S18161000000020
      • Zoning description: Resid Single Family

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Florida Cottage
      • Property subtype: Single Family Residence
      Materials
      • Frame, Siding CmntFbrHrdBrd
      • Foundation: Slab
      • Roof: Shingle
      Condition
      • Construction Complete
      • New construction: No
      • Year built: 2020

      Community & HOA

      Community
      • Features: BBQ Pit/Grill, Community Room, Dock, Fitness Center, Fishing, Golf, Short Term Rental - Not Allowed, Pavillion/Gazebo, Picnic Area, Playground, Pool, Tennis Court(s), Whirlpool
      • Security: Security System, Smoke Detector(s)
      • Subdivision: WATERSOUND ORIGINS
      HOA
      • Has HOA: Yes
      • Services included: Management
      Location
      • Region: Watersound

      Financial & listing details

      • Price per square foot: $682/sqft
      • Tax assessed value: $2,632,654
      • Annual tax amount: $23,312
      • Date on market: 4/3/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        4/3/2026Listed for sale$2,995,000-0.2%$682/sqft
        Source: ECAOR #999707 Report a problem
        4/3/2023Sold$3,000,000+100.7%$683/sqft
        Source: Public Record Report a problem
        8/17/2020Sold$1,495,000-3.5%$340/sqft
        Source: Public Record Report a problem
        6/26/2020Pending sale$1,549,000$353/sqft
        Source: Beach Properties of Florida #837223 Report a problem
        6/26/2020Price change$1,549,000-3.1%$353/sqft
        Source: Beach Properties of Florida #837223 Report a problem
        4/24/2020Listed for sale$1,599,000+699.5%$364/sqft
        Source: Berkshire Hathaway Home Services Beach Properties of Florida #837223 Report a problem
        5/16/2019Sold$200,000$46/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$23,788 +2.5%$2,632,654 +3.6%
        2024$23,205 +90.5%$2,540,409 +84.2%
        2023$12,182 +1.1%$1,379,006 +3%
        2022$12,054 -1.3%$1,338,841 +3%
        2021$12,218 +729.5%$1,299,846 +780.9%
        2020$1,473 +15.1%$147,552 +27.8%
        2019$1,279 $115,433 +10%
        2018$1,279 $104,939
        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.
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        Climate risks

        Neighborhood: 32461

        Getting around

        5 / 100
        Car-Dependent
        48 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Dune Lakes
        • 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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