85 Trailhead Dr

Watersound, FL 32461

$2,995,000
Price
5
Beds
4,394 Sq. Ft.
$682 / Sq. Ft.
4,394
Sq. Ft.
$682
per Sq. Ft.
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Virtual Tour
Virtual Tour
a front view of a house with a yard
a view of a swimming pool with chairs in patio
a living room with furniture and a flat screen tv
a kitchen with a dining table chairs and white cabinets
a bedroom with furniture and a chandelier
a living room with furniture and a large window
a kitchen with a stove a refrigerator and wooden floor
a view of backyard with a patio
a front view of a house with potted plants
a living room with a bed and a dresser
a bedroom with furniture and a large window
a bathroom with a sink and a mirror
a bathroom with a shower
a kitchen with stainless steel appliances a dining table chairs sink and cabinets
a kitchen with stainless steel appliances a stove a sink and a refrigerator
a view of an empty walk in closet
a kitchen with white cabinets and white appliances
a living room with furniture flat screen tv and a fireplace
a living room with furniture and a flat screen tv
a view of a dining room with furniture and wooden floor
a spacious bedroom with a bed and a chandelier
a spacious bedroom with a bed and a chandelier
a room with a furniture and a chandelier
a bathroom with a bathtub and a flat screen tv
a spacious bathroom with a granite countertop sink a large mirror and a light fixture
a bedroom with a bed and wooden floor
a bedroom with a bed and a flat screen tv
a bed room with a bed window and a flat screen tv
a view of swimming pool from a balcony
a bathroom with a double vanity sink mirror and
a white bath tub sitting next to a white toilet and a shower
a view of an empty walk in closet
a living room with furniture a flat screen tv and floor to ceiling windows
a living room with furniture and a flat screen tv
a view of a backyard with sitting area
a living room with furniture and a flat screen tv
a living room with furniture and a flat screen tv
a bathroom with a bathtub shower sink vanity and toilet
a view of an outdoor space
a view of a balcony with two chairs and a table
a front view of a house with a yard
a view of lake with green space
a view of an ocean
a view of a lake with a city
a view of an outdoor space and tennis court
view of a city
a view of a swimming pool with a patio
an aerial view of a swimming pool

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...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.
  1. Listed by Dahler & Co. • Brokerage DRE #1007656 • Scenic Sotheby's International Realty
    P: (850)-842-0420 dahlerandco@scenicsir.com

Property Details for 85 Trailhead Drive

Zoning
Resid Single Family
Architectural Style
Florida Cottage
Subdivision Name
WATERSOUND ORIGINS
LISTING UPDATED: 05/11/2026 11:27 AM

Property Details for 85 Trailhead Drive

StatusActive
MLS #999707
Days on Market48
Taxes$23,312 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Detached Single Family
Year Built2020
Lot Size0.27 AC / 11,761 SF
CountyWalton County
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Location

Listing Courtesy of Scenic Sotheby's International Realty
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Building Information for 85 Trailhead Drive

Stories2Year Built2020Building Size-Lot Size0.27 AC / 11,761 SF

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$16,867 per month

30 year fixed, 6.36% Interest

Principal and Interest

$14,924

Property Taxes

$1,943

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 85 Trailhead Drive

Summary
Location and General Information
  • 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
  • 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.
  • MLS Area Minor: 1805 - N of Hwy 98
  • MLS Area Major: 18 - 30A East
  • Latitude: 30.298474
  • Longitude: -86.009337
  • Location Tax and Legal:Sub Area: 1805 - N of Hwy 98
  • Location Tax and Legal:Elementary School: Dune Lakes
  • Location Tax and Legal:Middle School: Emerald Coast
  • Location Tax and Legal:High School: South Walton
  • Location Tax and Legal:Legal Description: LOT 2 PATHWAYS AT WATERSOUND PH 1 PB 20-34 OR 3053-3166 OR 3105-3426
  • Project Facilities: BBQ PitGrill2, Community Room, Dock2, Exercise Room, Fishing, Golf, PavillionGazebo2, Pets Allowed2, Picnic Area, Playground, Pool2, Short Term Rental - Not Allowed, Tennis, Whirlpool
  • Garage: true
Taxes and HOA
  • Association Fee Includes: Management
  • Tax Legal Description: LOT 2 PATHWAYS AT WATERSOUND PH 1 PB 20-34 OR 3053-3166 OR 3105-3426
  • Parcel Number: 24-3S-18-16100-000-0020
  • Association Fee: $0
  • Association YN: Yes
  • Tax Annual Amount: $23,312
  • Listing Info Tax Legal:Last Taxes: $23,312
  • Listing Info Tax Legal:Last Tax Year: 2025.0
School Information
  • Elementary School: Dune Lakes
  • Middle Or Junior School: Emerald Coast
  • High School: South Walton
Parking
  • Carport YN: No
  • Attached Garage YN: Yes
  • Garage Spaces: 2.0
  • General Property Info:Driveway Spaces: 6.0
  • Parking Features: Garage Attached
Virtual Tour
Property
Lot Information
  • Building Area Source: County PA Records
  • Lot Size Dimensions: 99 x 120 x 66 x 152
  • Lot Size Acres: 0.27
  • Lot Size Area: 0.27
  • Lot Size Units: Acres
  • Property Condition: Construction Complete
  • Building Area Total: 4394.0
  • Lot Size Square Feet: 11761.2
  • General Property Info:SqFt Source: County PA Records
Property and Assessments
  • Tax Year: 2025.0
  • Floor Plans Count: 0.0
  • Property Type: Residential
  • Year Built: 2020.0
  • Property Sub Type: Detached Single Family
  • New Construction YN: No
  • General Property Info:Sub-Type: Detached Single Family
  • General Property Info:Design: Florida Cottage
  • Construction Status: Construction Complete
  • Construction Siding: Frame, Roof Dimensional Shg, Siding CmntFbrHrdBrd, Slab
  • Occupancy Status: Occupied
Utilities
  • Utilities: Community Water, Electric, Gas - Natural, Gas - Propane
  • Electric: True
  • Utilities: Community Water, Electric, Gas - Natural, Gas - Propane
  • Energy: AC - 2 or More, AC - Central Elect, Water Heater - Tnkls
Interior and Exterior Features
Exterior Features
  • Exterior Features: Fenced Back Yard, Shower, Sprinkler System, Summer Kitchen
  • Construction Materials: Frame, Siding CmntFbrHrdBrd
  • Foundation Details: Slab
  • Stories: 2.0
  • Pool Features: Pool - In-Ground, Pool Type
  • Patio And Porch Features: Deck Covered, Porch Open, Porch Screened
  • General Property Info:Pool: Yes
  • General Property Info:Pool Type: Private
  • Exterior: Deck Covered, Fenced Back Yard, Fireplace2, Pool - In-Ground, Porch Open, Porch Screened, Shower, Sprinkler System, Summer Kitchen
Interior Features
  • Cooling: Central Air
  • Interior Features: Ceiling Beamed, Ceiling Crwn Molding, Ceiling Vaulted, Kitchen Island, Newly Painted, Owner's Closet, Washer/Dryer Hookup, Wet Bar
  • Fireplace Features: Fireplace Gas, Fireplace
  • Flooring: Floor Hardwood
  • Room Type: Living Room, Kitchen, Pantry, Bedroom, Full Bathroom, Master Bedroom, Master Bathroom, Separate Apartment
  • Rooms Total: 10.0
  • Bathrooms Total Integer: 6.0
  • Bathrooms Total Decimal: 5.0
  • Bathrooms Total Notational: 4.2
  • Cooling YN: Yes
  • Fireplace YN: Yes
  • Bedrooms Total: 5.0
  • Bathrooms Full: 4.0
  • Bathrooms Half: 2.0
  • Interior: Ceiling Beamed, Ceiling Crwn Molding, Ceiling Vaulted, Fireplace Gas, Floor Hardwood, Kitchen Island, Newly Painted, Owner's Closet, WasherDryer Hookup, Wet Bar
  • Appliances: Auto Garage Door Opn, Cooktop, Dishwasher, Disposal, Freezer, Ice Machine, Microwave, Range Hood, Refrigerator WIceMk, Security System, Smoke Detector, StoveOven Gas, Wine Refrigerator
Room Information
Room 1
  • Room Type: Living Room
  • Room Level: First
  • Room Length: 26.1
  • Room Width: 20.0
  • Room Dimensions: 26.1 x 20
Room 2
  • Room Type: Kitchen
  • Room Level: First
  • Room Length: 11.0
  • Room Width: 20.0
  • Room Dimensions: 11 x 20
Room 3
  • Room Type: Pantry
  • Room Level: First
  • Room Length: 9.4
  • Room Width: 10.6
  • Room Dimensions: 9.4 x 10.6
Room 4
  • Room Type: Bedroom
  • Room Level: First
  • Room Length: 13.11
  • Room Width: 16.0
  • Room Dimensions: 13.11 x 16
Room 5
  • Room Type: Full Bathroom
  • Room Level: First
  • Room Length: 5.4
  • Room Width: 5.3
  • Room Dimensions: 5.4 x 5.3
Room 6
  • Room Type: Bedroom
  • Room Level: Second
  • Room Length: 13.9
  • Room Width: 13.0
  • Room Dimensions: 13.9 x 13
Room 7
  • Room Type: Bedroom
  • Room Level: Second
  • Room Length: 13.11
  • Room Dimensions: 13.11 x 14.6
Room 8
  • Room Type: Master Bedroom
  • Room Level: Second
  • Room Length: 18.8
  • Room Width: 14.0
  • Room Dimensions: 18.8 x 14
Room 9
  • Room Type: Master Bathroom
  • Room Level: Second
  • Room Length: 7.4
  • Room Width: 15.6
  • Room Dimensions: 7.4 x 15.6
Room 10
  • Room Type: Separate Apartment
  • Room Level: Second
  • Room Length: 27.0
  • Room Width: 18.3
  • Room Dimensions: 27 x 18.3
Rental
Rent Information
  • Listing Info Tax Legal:Is Subject Leased: false

Property History for 85 Trailhead Drive

DateEvent & SourcePriceAppreciation
Apr 3, 2026

Listed (Active)

ECAR #999707

$2,995,000—
Apr 3, 2023

Sold (Public Record)

Public Record #1508941567

$3,000,000

+30.3% / yr

Aug 14, 2020

Sold (Public Record)

Public Record #677296674

$1,495,000—
DateEvent & SourcePrice
04/03/2026

Listed (Active)

ECAR #999707

$2,995,000
04/03/2023

Sold (Public Record)

Public Record #1508941567

$3,000,000

+30.3% / yr

08/14/2020

Sold (Public Record)

Public Record #677296674

$1,495,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 85 Trailhead Drive

Taxable ValueLand$297,562Additions$2,335,092Total$2,632,654
Tax Record2024$23,205 ($1,934 / month)
Home Facts
Beds4Total Finished SqFt4,394 SqFtAbove Grade Finished SqFt4,394 SqFtStories2Lot Size12,023 SqFtStyleSingle Family ResidenceYear Built2020CountyWALTONAPN24-3S-18-16100-000-0020

Schools near 85 Trailhead Drive

This home is within Walton.
Rating
School
Type
Grades
Distance
Dune Lakes Elementary School
Public - K to 5
Emerald Coast Middle School
Public - 6 to 8
South Walton High School
Public - 9 to 12
Seaside Neighborhood School
Charter - 5 to 12
Rating
School
Distance
Dune Lakes Elementary School
PublicK to 5

Emerald Coast Middle School
Public6 to 8

South Walton High School
Public9 to 12

Seaside Neighborhood School
Charter5 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 85 Trailhead Drive, Watersound, FL 32461

85 Trailhead Drive is a single family home for sale in Watersound, FL 32461. This property was listed for sale on April 3, 2026 by Scenic Sotheby's International Realty, it's currently listed at $2,995,000. It has been on the market for a total of 48 days and was last sold on April 3, 2023. This listing's school district is Walton. Nearby schools include Dune Lakes Elementary School, Emerald Coast Middle School and South Walton High School. 85 Trailhead Drive is a 5-bed, 6-bath, 4,394 sqft single family home built in 2020.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Scenic Sotheby's International Realty

The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the Emerald Coast Association of REALTORS, Central Panhandle Association of REALTORS, Pensacola Association of REALTORS and Capital Area Technology & REALTOR Services. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Information deemed reliable but not guaranteed. Copyright© 2026 Emerald Coast Association of REALTORS, Central Panhandle Association of REALTORS, Pensacola Association of REALTORS and Capital Area Technology & REALTOR Services. All Rights Reserved.