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85 Trailhead Drive, 
Watersound, FL 32461

$2,995,000


5

Beds


6

Baths


4,394

Sq Ft


Single Family

Active

Listed by

Dahler & Co.

Scenic Sotheby'S International Realty

Last updated:

April 22, 2026, 02:44 PM

MLS#

999707

Source:

FL ECAR

About This Home

85 Trailhead Drive

Where luxury meets effortless coastal living, this 4,394-square-foot custom Watersound Origins residence unfolds with quiet confidence — every detail thoughtfully considered, every space inviting 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 anchors the outdoor experience, complemented by a summer kitchen and a covered lounge with a fireplace — evenings linger and gatherings unfold with ease. Upstairs, the primary suite serves as a true retreat, with mornings beginning softly and evenings winding 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, this home is part of a community that balances natural beauty with thoughtful design, offering access to golf, dining, and the nearby beaches of Scenic Highway 30A. It’s a place where the pace feels just right, and where everyday living carries a sense of ease, intention, and understated luxury.

Home Facts

Single Family

6 Baths

5 Bedrooms

Built in 2020

Price Summary

2,995,000

$681 per Sq. Ft.

MLS #:

999707

Last Updated:

April 22, 2026, 02:44 PM

Added:

20 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

6

Full Bathrooms:

4

Interior

Living Area:

4,394 Sq. Ft.


Structure

Structure

Architectural Style:

Florida Cottage

Building Area:

4,394 Sq. Ft.

Year Built:

2020


Lot

Lot Size (Sq. Ft):

11,761


Finances & Disclosures

Finances

Price:

$2,995,000

Price per Sq. Ft:

$681 per Sq. Ft.

Source:FL ECAR
The information being provided by Emerald Coast Association Of REALTORS® is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Emerald Coast Association Of REALTORS®. Scenic Sotheby'S International Realty is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Scenic Sotheby'S International Realty, a broker participant of Emerald Coast Association Of REALTORS®. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by Emerald Coast Association Of REALTORS® and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited. Properties in listings may have been sold or may no longer be available. Copyright 2026 Emerald Coast Association Of REALTORS®. All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.