286 VALE Drive, St. Augustine, FL 32095

• 5 beds |
• 5 baths |
• 3,781 sqft

Property Description

Tucked behind lush landscaping and designed for both privacy and connection, this exceptional John Kenny Custom Home offers a living experience unlike any other. From the moment you arrive, you're welcomed into a stunning courtyard centered around a sparkling pool--the heart of the home. The main residence is thoughtfully positioned on one side, while a private ''Casita'' sits on the other, creating a retreat-style setting ideal for guests, extended family, a home office, or multigenerational living. A whole-house Generac generator delivers reliable backup power, allowing you to enjoy your home year-round without interruption. Offered for the very first time by its original owners, this meticulously maintained property features a total of 5 bedrooms, 4.5 bathrooms, and a 3 car garage. The main home includes a first-floor bedroom and full bath, with two additional bedrooms and two baths upstairs. Across the courtyard, the detached casita offers a first-floor bedroom and full bath, while the oversized upper-level suite features its own full bath and built-in kitchenette, providing ample space to be used as a guest suite, office or entertaining flex space. Inside, wood flooring flows throughout the main living areas, where a gas fireplace serves as the centerpiece of the family room. The thoughtfully designed floor plan includes an eat-in kitchen for casual dining as well as a separate dining room for special occasions. Beautiful exposed wood beam ceilings showcase the craftsmanship and character expected in a John Kenny custom home. This truly is a rare opportunity to own a one-of-a-kind property offering flexibility, privacy, and timeless design.

Listing Status:

Active

Date Added:

June 4, 2026

Data Last Updated:

June 14, 2026 at 3:37AM

Listing Office:

COMPASS FLORIDA LLC : 904-413-0119

Listing Agent:

CRICKETT HUFF : 904-728-3333

MLS ID:

2148803

Interior

• General: Breakfast BarBuilt-in FeaturesCeiling Fan(s)Entrance FoyerEat-in KitchenHis and Hers ClosetsIn-Law FloorplanKitchen IslandPantryPrimary DownstairsSmart ThermostatVaulted Ceiling(s)Wet BarWalk-In Closet(s)Primary Bathroom -Tub with Separate ShowerSplit BedroomsBreakfast NookGuest SuiteJack and Jill Bath
• Appliances: Convection OvenDryerDisposalDishwasherGas CooktopGas OvenGas Water HeaterMicrowaveRefrigeratorWasher
• Laundry: Lower LevelIn Unit
• Flooring: CarpetTileWood
• A/C: Central AirMulti UnitsZoned
• Heating:
• Fireplace: GasFireplaceFireplaces: 1

Exterior

• General: CourtyardGuest House
• Style: Multi Generational
• Pool: HeatedIn GroundPool SweepScreen EnclosureWaterfall

Construction

• Roofing: Shingle
• General: Frame2

Location

• Road/Access: County Road
• HOA Amenities: Dog ParkFitness CenterParkPlaygroundSpa/Hot TubTennis Court(s)TrashPickleballChildren's PoolManagement - Off SitePoolMaintenance StructureSecuritySewerTrashWater125.0Annually
• Originating MLS: realMLS (Northeast Florida Multiple Listing Service)
• County: St. Johns

Lot

• Zoning: 0720940170
• View: PoolProtected Preserve
• Current Use: ResidentialSingle Family

Utilities

• Utilities: Cable AvailableElectricity AvailableElectricity ConnectedNatural Gas AvailableSewer ConnectedWater AvailableWater ConnectedWhole House Generator
• Water: Public
• Sewer: Public Sewer

Financial

• Source: realMLS (Northeast Florida Multiple Listing Service)