85 Trailhead Dr
Watersound, FL 32461
5 Beds
5 Baths
4,394 sqft (on 0.27 acres)
5 Beds
5 Baths
4,394 sqft
(on 0.27 acres)
We estimate this home will sell faster than 96% nearby.
Local Information
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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.
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.
We estimate this home will sell faster than 96% nearby.
Home Highlights
Parking
2 Car Garage
Outdoor
Porch, Pool
View
No Info
HOA
None
Price/Sqft
$682
Listed
35 days ago
Home Details for 85 Trailhead Dr
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Interior Details Number of Rooms: 10Types of Rooms: Master Bedroom, Bedroom, Master Bathroom, Bathroom, Kitchen, Living Room, Pantry, Separate ApartmentWet Bar |
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 4Number of Bathrooms (half): 2 |
Dimensions and Layout Living Area: 4394 Square Feet |
Appliances & Utilities Appliances: Cooktop, Dishwasher, Disposal, Freezer, Microwave, Range Hood, Tankless Water HeaterDishwasherDisposalLaundry: Washer/Dryer HookupMicrowave |
Heating & Cooling Heating: Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Natural Gas |
Fireplace & Spa Fireplace: EPA Qualified Fireplace, GasHas a Fireplace |
Windows, Doors, Floors & Walls Flooring: HardwoodCommon Walls: No Common Walls |
Levels, Entrance, & Accessibility Stories: 2Floors: Hardwood |
View No View |
Security Security: Security System, Smoke Detector(s) |
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Exterior Home Features Roof: ShinglePatio / Porch: Covered, Porch, ScreenedExterior: Private Yard, Outdoor Shower, Sprinkler System, Outdoor KitchenFoundation: SlabSprinkler System |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Door Opener |
Pool Pool: In GroundPool |
Frontage Not on Waterfront |
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Days on Market: 35 |
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Year Built Year Built: 2020 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Florida Cottage |
Building Construction Materials: Frame, Siding CmntFbrHrdBrdNot a New ConstructionNot Attached Property |
Property Information Condition: Construction CompleteParcel Number: 243S18161000000020 |
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Price List Price: $2,995,000Price Per Sqft: $682 |
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MLS Status: Active |
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Direction & Address City: WatersoundCommunity: WATERSOUND ORIGINS |
School Information Elementary School: Dune LakesJr High / Middle School: Emerald CoastHigh School: South Walton |
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Listing Agent Listing ID: 999707 |
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Building Area Building Area: 4394 Square Feet |
Community rooms Fitness Center |
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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 |
Other Playground |
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HOA Fee Includes: Management |
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Lot Area: 0.27 acres |
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Mls Number: 999707Attribution Contact: dahlerandco@scenicsir.com |
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BBQ Pit/GrillCommunity RoomDockFishingGolfShort Term Rental - Not AllowedPavillion/GazeboPicnic AreaPlaygroundPoolTennis Court(s)Whirlpool |
Last check for updates: about 8 hours ago
Listing courtesy of Dahler & Co.
Scenic Sotheby's International Realty
Source: ECAOR, MLS#999707
Also Listed on ECAOR.
Price History for 85 Trailhead Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 04/03/2026 | $2,995,000 | Listed For Sale | ECAOR #999707 |
| 04/03/2023 | $3,000,000 | Sold | N/A |
| 08/17/2020 | $1,495,000 | Sold | N/A |
| 06/26/2020 | $1,549,000 | Pending | Agent Provided |
| 06/26/2020 | $1,549,000 | PriceChange | Agent Provided |
| 04/24/2020 | $1,599,000 | Listed For Sale | Agent Provided |
| 05/16/2019 | $200,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $23,205 |
| Assessment | $2,540,409 |
Home facts updated by county records
Comparable Sales for 85 Trailhead Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.17 | Single-Family Home | $1,850,000 | 03/30/26 | 5 | 5 | 3,702 | |
0.25 | Single-Family Home | $3,530,000 | 10/15/25 | 5 | 6 | 4,660 | |
0.26 | Single-Family Home | $3,700,000 | 06/06/25 | 5 | 6.5 | 5,292 | |
0.39 | Single-Family Home | $2,300,000 | 04/03/26 | 5 | 4.5 | 4,192 | |
0.21 | Single-Family Home | $1,650,000 | 03/30/26 | 5 | 4 | 3,732 | |
0.41 | Single-Family Home | $2,280,000 | 09/04/25 | 4 | 5 | 4,069 | |
0.44 | Single-Family Home | $2,265,000 | 04/13/26 | 4 | 4.5 | 3,827 | |
0.35 | Single-Family Home | $1,425,000 | 12/11/25 | 4 | 4.5 | 3,397 |
Assigned Schools
These are the assigned schools for 85 Trailhead Dr.
- South Walton High School
- 9-12
- Public
- 1017 Students
8/10GreatSchools RatingParent Rating AverageThe freshman AP History teacher is a disrespectful bully and an ineffective teacher. Avoid him at all costs. This school is does not prepare students for today's world.Student Review7mo ago - Bay Elementary School
- K-5
- Public
- 911 Students
10/10GreatSchools RatingParent Rating AverageWonderful school. We are actually in a different zone but enrolled our child here.Parent Review8y ago - Emerald Coast Middle School
- 6-8
- Public
- 910 Students
8/10GreatSchools RatingParent Rating AverageThe school does not have a welcoming and good educational environment. The interaction of the students is clique, which makes it hard for new students to assimilate. The teachers seem very interested in helping the students learn but there is an issue with the administrative staff. They will question your child and intimidate them so advise your child to have a parent present if questioned. The Staff appears to be enthusiastic for the school and students but below the surface we did not find a very caring place for our student to excel.Parent Review2y ago 
Check out schools near 85 Trailhead Dr.
What Locals Say about Inlet Beach
At least 28 Trulia users voted on each feature.
89 % Say it's dog friendly
79 % Say it's walkable to restaurants
79 % Say parking is easy
79 % Say people would walk alone at night
77 % Say yards are well-kept
77 % Say car is needed
74 % Say there are sidewalks
73 % Say it's quiet
66 % Say kids play outside
53 % Say they plan to stay for at least 5 years
53 % Say there's holiday spirit
49 % Say there are community events
45 % Say streets are well-lit
43 % Say there's wildlife
39 % Say neighbors are friendly
30 % Say it's walkable to grocery stores
Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Dahler & Co., Scenic Sotheby's International Realty
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Member number: 28189
85 Trailhead Dr, Watersound, FL 32461 is a 5 bedroom, 6 bathroom, 4,394 sqft single-family home built in 2020. This property is currently available for sale and was listed by ECAOR on Apr 3, 2026. The MLS # for this home is MLS# 999707.