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$2,995,000

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 2 Partial Baths
  • 4,394 Sq. Ft.
  • Updated 2 days ago
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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.

Full Property Details for 85 Trailhead Dr

General

  • Price: $2,995,000
  • Taxes: $23,312 (2025)
  • Status: Active
  • Type: Single Family
  • Source: Emerald_Coast
  • MLS ID: 999707
  • Updated: 4/13/2026
  • Added to Site: 21 day(s) ago

Rental Information

  • Complex 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

Interior

  • Number of Rooms: 10
  • Interior Features: Ceiling Beamed, Ceiling Crwn Molding, Ceiling Vaulted, Kitchen Island, Newly Painted, Owner's Closet, Washer/Dryer Hookup, Wet Bar
  • Fireplace: Yes
  • Fireplace(s): Fireplace Gas, Fireplace
  • Appliances: 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
  • Flooring: Floor Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 6
  • Full Bathrooms: 4
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 5

Additional Information

  • Pool: Yes
  • Pool Description: Pool - In-Ground, Pool Type

Exterior

  • Exterior Features: Fenced Back Yard, Shower, Sprinkler System, Summer Kitchen
  • Porch/Patio/Deck: Deck Covered, Porch Open, Porch Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2

Location

  • Area: 18 - 30A East
  • County: Walton
  • Subdivision: WATERSOUND ORIGINS
  • Driving Directions: 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.

School Information

  • Elementary School: Dune Lakes
  • Middle School: Emerald Coast
  • High School: South Walton

Community

  • Association: Yes
  • Assoc. Fees Include: Management

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Central Air
  • Heating/Cooling: Central Air

Utilities

  • Utility Description: Community Water, Electric, Gas - Natural, Gas - Propane

Structural Information

  • Architectural Style: Florida Cottage
  • Construction: Frame, Siding CmntFbrHrdBrd
  • Exterior Const.: Frame, Siding CmntFbrHrdBrd
  • Stories/Levels: 2
  • Square Feet: 4,394
  • Sq. Ft. Source: County PA Records
  • Year Built: 2020

Lot Features

  • Lot Size (Acres): 0.27
  • Lot Size (Sq. Ft.): 11,761.2
  • Lot Dimensions: 99 x 120 x 66 x 152
  • Zoning: Resid Single Family

Financial Considerations

  • Assessment Amount: $680
  • Tax Amount: $23,312.11
  • Tax Year: 2025

Disclosures and Reports

  • Legal Description: LOT 2 PATHWAYS AT WATERSOUND PH 1 PB 20-34 OR 3053-3166 OR 3105-3426
  • APN: 24-3S-18-16100-000-0020
  • Property ID: 24-3S-18-16100-000-0020

Listed by Scenic Sotheby's International Realty

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Listing agent

— 85 Trailhead Dr —

  • Scenic Sotheby's International Realty

dahlerandco@scenicsir.com

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 85 Trailhead Dr

School District:Walton County School District
NameGradesDistance
Bay Elementary School
6565 US Highway 98 East, Santa Rosa Beach, FL 32459
K-55.1 mi
Emerald Coast Middle School
4019 US Highway 98 East, Santa Rosa Beach, FL 32459
6-87.4 mi
South Walton High School
645 Greenway Trail, Santa Rosa Beach, FL 32459
9-1211.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 85 Trailhead Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/03/2026
Listed
$2,995,000
-0.17%
MLS
4/03/2023
Sold
$3,000,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 85 Trailhead Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$23,205
—
$2,632,654
4%
2024
$23,205
90%
$2,540,409
-8%
2023
$12,182
—
$2,759,507
112%
2021
$12,218
1%
$1,299,846
-39%
2022
$12,054
-1%
$2,144,161
1353%
2021
$12,218
855%
$147,552
28%
2019
$1,279
22%
$115,433
10%
2018
$1,046
—
$104,939
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Scenic Sotheby's International Realty

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85 Trailhead Drive, Watersound, FL 32461 (MLS# 999707) is a Single Family property with 5 bedrooms, 4 full bathrooms and 2 partial bathrooms. 85 Trailhead Drive is currently listed for $2,995,000 and was received on April 03, 2026. Want to learn more about 85 Trailhead Drive? Do you have questions about finding other Single Family real estate for sale in Watersound? You can browse all Watersound real estate or contact a Coldwell Banker agent to request more information.

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