2068 ROBERTS POINT DRIVE, Windermere, FL 34786

• 5 beds |
• 4 baths |
• 4,876 sqft

Property Description

One or more photo(s) has been virtually staged. Private Windermere Estate in Guard-Gated Waterford Pointe with Detached Guest Casita and Lake Access. A rare opportunity in one of Windermere’s most established guard-gated communities, this private estate offers the space, flexibility, and lifestyle today’s luxury buyers are actively seeking. Set on over an acre within Waterford Pointe, the property combines architectural presence, exceptional privacy, and resort-inspired living in a peaceful enclave known for estate-sized homes, mature landscaping, and private access to Lake Roberts. Designed around a dramatic courtyard pool, the home creates a true indoor-outdoor lifestyle experience, ideal for both grand entertaining and everyday living. The detached guest casita is a standout feature, offering exceptional flexibility for guests, private office use, wellness retreat, creative studio, or evolving lifestyle needs. Inside, soaring ceilings, polished marble tile flooring, detailed crown molding, and dramatic two-story living spaces create a sense of scale and elegance throughout. The thoughtfully updated chef’s kitchen is designed for gathering, featuring quartz countertops, an oversized island, premium KitchenAid and Bosch appliances, double ovens, wine refrigeration, and seamless connection to the expansive family room with custom built-ins and fireplace. The private first-floor primary suite serves as a true retreat, offering direct courtyard and pool access, a spacious custom walk-in closet, and a beautifully appointed bath with dual vanities, jetted soaking tub, and walk-in shower. A second first-floor suite provides ideal accommodations for guests or family. Upstairs, expansive, flexible living spaces include a large game room overlooking the courtyard, a dedicated office with custom built-ins, a private fitness room with balcony access, and additional secondary bedrooms thoughtfully arranged for privacy and functionality. Outdoor living is equally compelling, with a screened resort-style saltwater pool and heated spa with waterfall, covered summer kitchen, multiple entertaining spaces, and the privacy that only a homesite of this scale can provide. Waterford Pointe residents enjoy an exceptional lifestyle with private access to Lake Roberts, a waterfront clubhouse, tennis courts, playground, and beautifully tree-lined streets—all within one of Windermere’s most desirable gated communities. Additional highlights include a 4-car garage, a new whole-house generator, three HVAC systems, a newly painted exterior courtyard, and highly regarded local schools. For buyers seeking privacy, architectural character, flexible living, and established Windermere luxury—without the premium of direct lakefront pricing—this is a compelling opportunity. **Private tours available by appointment**

Listing Status:

Active

Date Added:

April 16, 2026

Data Last Updated:

June 25, 2026 at 4:24AM

Listing Office:

CENTURY 21 CARIOTI : 407-573-2121

Listing Agent:

David Dorman : 407-948-8295

MLS ID:

O6397543

Interior

• General: Built-in FeaturesCathedral Ceiling(s)Ceiling Fans(s)Chair RailCrown MoldingDry BarEat-in KitchenHigh CeilingsKitchen/Family Room ComboOpen FloorplanPrimary Bedroom Main FloorSplit BedroomStone CountersThermostatTray Ceiling(s)Walk-In Closet(s)
• Rooms: Bonus RoomDen/Library/OfficeFamily RoomFormal Dining Room SeparateFormal Living Room SeparateInside UtilityInterior In-Law Suite w/Private EntryStorage Rooms
• Appliances: Built-In OvenConvection OvenCooktopDishwasherDisposalElectric Water HeaterMicrowaveRange HoodRefrigeratorWater Filtration SystemWhole House R.O. SystemWine Refrigerator
• Laundry: Electric Dryer HookupLaundry Room
• Flooring: BrickCarpetCeramic TileWood
• A/C: Central AirZoned
• Heating: ElectricHeat PumpZoned
• Fireplace: ElectricFamily RoomNon Wood BurningFireplace
• Eco/Green Feature: ThermostatLow-Flow FixturesWhole House Water Purification

Exterior

• General: BalconyCourtyardFire PitFrench DoorsLightingOutdoor GrillOutdoor KitchenPrivate EntrancePrivate MailboxRain GuttersSidewalkHeatedIn Ground
• Style: CourtyardCustomFloridaOtherTraditional
• Other Structures: CabanaOtherEnclosedScreenedPatioSide PorchCovered
• Pool: Child Safety FenceGuniteHeatedIn GroundLightingOtherOutside Bath AccessSalt WaterScreen EnclosureSelf Cleaning
• Parking: BoatCircular DrivewayDrivewayGarage Door OpenerGarage Faces SideGolf Cart ParkingGuestParking Pad

Construction

• Roofing: Tile
• Windows: BlindsShadesShutters
• General: BlockStoneStuccoTwoSlab

Location

• Road/Access: AsphaltPaved
• HOA Amenities: ClubhouseFence RestrictionsGatedParkPlaygroundRecreation FacilitiesSecurityTennis Court(s)Vehicle RestrictionsGuard - 24 HourPrivate RoadRecreational Facilities325.0Monthly
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: R-CEWATERFORD POINTE PH 2 REPLAT 34/125 LOT5601-23-27-9110-00-560
• View: Trees/Woods
• Fencing: Other

Utilities

• Utilities: Cable AvailableElectricity ConnectedPhone AvailablePropaneSprinkler WellUnderground UtilitiesWater Connected
• Water: Public
• Sewer: Septic Tank

Financial

• Source: Stellar MLS
• Ownership: Fee Simple