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85 Trailhead DR Watersound, FL 32461 Active

UPDATED: 04/06/2026 03:28 PM ON MARKET: 10 days on market

$2,995,000

5 Beds6 Baths4,394 SqFt

Key Details

Property Type Single Family Home

Sub Type Detached Single Family

Listing Status Active

Purchase Type For Sale

Square Footage 4,394 sqft

Price per Sqft $681

Subdivision Watersound Origins

MLS Listing ID 999707

Style Florida Cottage

Bedrooms 5

Full Baths 4

Half Baths 2

HOA Y/N Yes

Year Built 2020

Annual Tax Amount $23,312

Tax Year 2025

Lot Size 0.270 Acres

Acres 0.27

Lot Dimensions 99 x 120 x 66 x 152

Property Sub-Type Detached Single Family

Source Emerald Coast Association of REALTORS®

Land Area 4394

Location

State FL

County Walton

Community Short Term Rental - Not Allowed,Bbq Pit/Grill,Community Room,Dock,Exercise Room,Fishing,Golf,Pavillion/Gazebo,Pets Allowed,Picnic Area,Playground,Pool,Tennis,Whirlpool

Area 18 - 30A East

Zoning Resid Single Family

Direction From Sandestin, head east on Hwy 98 approximately 19 miles. Watersound Origins is located along the north side of Hwy 98. Head north into the community, turn right onto Pathways Drive and then a left on Trailhead, its the second house on the left.

Rooms

Primary Bedroom Level Upper

Master Bedroom true

Kitchen true

Interior

Interior Features Ceiling Beamed,Ceiling Crwn Molding,Ceiling Vaulted,Kitchen Island,Newly Painted,Owner's Closet,Washer/Dryer Hookup,Wet Bar

Cooling Central Air

Flooring Floor Hardwood

Fireplaces Type Fireplace Gas,Fireplace

Fireplace Yes

Appliance Auto Garage Door Opn,Cooktop,Dishwasher,Disposal,Freezer,Ice Machine,Microwave,Range Hood,Refrigerator W/IceMk,Security System,Smoke Detector,Stove/Oven Gas,Wine Refrigerator,Water Heater - Tnkls

Exterior

Exterior Feature Fenced Back Yard,Shower,Sprinkler System,Summer Kitchen, In-Ground Pool, Covered Deck, Open Porch, Screened Porch, Fenced Backyard, Summer Kitchen, Exterior Fireplace, Outdoor Shower, Sprinkler System

Garage Spaces 2.0

Pool Pool - In-Ground,Pool Type

Community Features Short Term Rental - Not Allowed,BBQ Pit/Grill,Community Room,Dock,Exercise Room,Fishing,Golf,Pavillion/Gazebo,Pets Allowed,Picnic Area,Playground,Pool,Tennis,Whirlpool

Utilities Available Community Water,Electric,Gas - Natural,Gas - Propane

Roof Type Dimensional Shingle

Porch Deck Covered,Porch Open,Porch Screened

Garage Yes

Building

Faces From Sandestin, head east on Hwy 98 approximately 19 miles. Watersound Origins is located along the north side of Hwy 98. Head north into the community, turn right onto Pathways Drive and then a left on Trailhead, its the second house on the left.

Story 2

Foundation Slab

Architectural Style Florida Cottage

New Construction No

Schools

Elementary Schools Dune Lakes

Middle Schools Emerald Coast

High Schools South Walton

Others

Pets Allowed No

HOA Fee Include Management

Tax ID 24-3S-18-16100-000-0020

Miscellaneous 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.

Virtual Tour https://my.matterport.com/show/?m=afqUdrcgb8G&brand=0&mls=1&

Property Description

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.