17737 DEER ISLE CIRCLE, Winter Garden, FL 34787

• 5 beds |
• 5 baths |
• 4,886 sqft

Property Description

Experience over an acre of elevated direct sunset lakefront luxury living on the naturally spring-fed waters of John’s Lake. Offered publicly for the first time, this fully custom estate represents a rare convergence of beauty, privacy and enduring design. Nearly 5,000 square feet of interior living space unfold effortlessly into an additional 1,000 square feet of exceptionally well-appointed enclosed outdoor living, creating seamless indoor to outdoor living. Positioned within the private gated enclave of Deer Island and presented in impeccable condition since its 2015 construction, the home reflects meticulous care and pride of ownership. Thoughtfully designed for a life well lived by owners and guests alike, every detail was executed with intention. Arrival is elegant and memorable, welcomed by a central fountain and expansive motor court leading to an oversized three-car garage, while two bedrooms on the main level, including the primary and guest suite, provide comfort, privacy and effortless livability for generations. Designed for entertaining, walls of fully retractable sliding glass doors dissolve the boundary between indoors and out, allowing the living and great rooms to open to the terrace beyond. The covered outdoor lounge, finished with a wood-paneled ceiling, gas fireplace and fully equipped outdoor kitchen, extends daily living outdoors. The infinity pool and spa, framed by gas fire bowls, merge seamlessly with the lake view itself, while a dedicated pool access bath enhances convenience. Privately positioned to capture sweeping lake views, the primary suite opens directly to the lanai and features dual walk-in closets. Its bath is anchored by a freestanding copper soaking tub, hammered copper sinks set within custom vanities, and a full stone walk-in shower with multiple showerheads and built-in bench. The kitchen features custom wood cabinetry, oversized island, induction cooktop, separate built-in refrigerator and freezer, professional-grade appliances, and walk in pantry. Architectural details include travertine flooring, coffered and tray ceilings, refined millwork and wrought iron staircase. All closets feature custom built-ins. The second-floor media room may also serve as a spacious fifth bedroom with private balcony overlooking the lake. Beyond the terrace, tiered gardens descend toward the shoreline, where Four Seasons marble statuary is thoughtfully placed throughout the grounds, like a work of art set within the landscape. A private putting green, fire pit and manicured lawn enhance the setting. The composite dock includes dual lifts for boat and jet ski, water and electric service, and upper level sun deck positioned for sunset views. John’s Lake spans over 2,500 acres and is known for exceptional clarity, ideal for skiing, boating, water sports and fishing. Deer Island offers gated entry with waterside tennis, pickleball and basketball courts. The home is serviced by a private well. Less than one mile from the Florida Turnpike and 25 minutes to downtown Orlando. Contact for your private viewing.

Listing Status:

Active

Date Added:

February 25, 2026

Data Last Updated:

February 27, 2026 at 10:23PM

Listing Office:

PREMIER SOTHEBY'S INTL. REALTY : 407-644-3295

Listing Agent:

Candace Cassidy : 407-529-8630

MLS ID:

O6381953

Interior

• General: Cathedral Ceiling(s)Ceiling Fans(s)Coffered Ceiling(s)Crown MoldingEat-in KitchenHigh CeilingsIn Wall Pest SystemKitchen/Family Room ComboOpen FloorplanPrimary Bedroom Main FloorSolid Surface CountersSplit BedroomStone CountersThermostatTray Ceiling(s)Walk-In Closet(s)Window Treatments
• Rooms: Den/Library/OfficeFormal Dining Room SeparateFormal Living Room SeparateGreat Room
• Appliances: Built-In OvenConvection OvenCooktopDishwasherDisposalElectric Water HeaterExhaust FanFreezerMicrowaveRefrigeratorTankless Water HeaterWater Softener
• Laundry: Electric Dryer HookupInsideLaundry RoomWasher Hookup
• Flooring: TravertineWood
• A/C: Central AirZoned
• Heating: CentralElectricZoned
• Fireplace: GasLiving RoomOutsideFireplace
• Eco/Green Feature: HVACLightingThermostatWater HeaterWindows

Exterior

• General: BalconyFire PitLightingOutdoor GrillOutdoor KitchenPrivate MailboxRain GuttersSliding DoorsHeatedIn Ground
• Style: Mediterranean
• Other Structures: Outdoor KitchenScreenedCovered
• Pool: Chlorine FreeIn GroundInfinityLightingOutside Bath AccessPool AlarmSalt WaterScreen EnclosureSelf Cleaning
• Parking: DrivewayGarage Door OpenerGarage Faces Side

Construction

• Roofing: Tile
• Windows: Double Pane WindowsInsulated WindowsLow-Emissivity WindowsShuttersThermal WindowsTinted Windows
• General: BlockStuccoFrameTwoSlab

Location

• Road/Access: Asphalt
• HOA Amenities: GatedPickleball Court(s)Private Road1240.0Semi-Annually
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: P-DDEER ISLAND 15/63 LOT 11 & THAT PART OFOCCUPIED LAND LYING BETWEEN THE LOT ANDTHE ORDINARY HIGH WATER LINE OF JOHNS LAKE BOUNDED BY THE EXTENSIONS OF THE LOTLINES EXTENDED TO THE OHWL30-22-27-1985-00-110
• View: Water

Utilities

• Utilities: Cable ConnectedElectricity ConnectedPropaneSprinkler Well
• Water: Well
• Sewer: Aerobic SepticSeptic Tank

Financial

• Source: Stellar MLS
• Ownership: Fee Simple