39851 & 39855 DARLINGTON AVENUE, Lady Lake, FL 32159

• 5 beds |
• 6 baths |
• 5,278 sqft

Property Description

Welcome to a rare opportunity in Central Florida real estate, welcome to the private, gated, exclusive community of Windsor Greene in Lady Lake, offering two separate residences, RV and boat storage, and fully insulated three-car garage on 2.35 scenic hilltop acres. Just minutes from The Villages, and within an hour of Orlando International Airport and Disney World, this one-of-a-kind property is ideal for multi-generational living, snowbirds with RVs, car or motorcycle collectors, or those seeking a quiet, natural setting with easy access to Ocala’s equestrian life and major urban amenities. The main residence spans 3,426 feet and features a hybrid open layout with three en-suite bedrooms and 3.5 baths. Thoughtful details include 12-foot ceilings, 8-foot solid core doors, custom walk-in closets, and 32-by-32-inch porcelain slab floors with onyx finish throughout. The kitchen flows with a partial wall opening to the main salon, finished with high-grade stone countertops and porcelain tile baths that blend function with subtle elegance. A porcelain slab with onyx finish fireplace anchors the living room, flanked by French doors opening to a lanai with tranquil views and a newly planted tree line that enhances privacy and green space. All windows are vinyl, double glass, tinted and fiberglass doors for easy maintenance. The second home is 1,720 interior square feet, offering a split floor plan with an open-concept living area and an attached two-car (or oversized truck) garage, ideal for guests, extended family, rental income, or a home office for remote work or a family business. Both homes feature bright, well-designed laundry rooms that elevate everyday tasks. The detached garage structure includes 16-foot ceilings, commercial-grade doors rated to 150 mph and is fully insulated, making it ideal for vehicle collectors, secure storage or hobbyist use. Built with concrete block construction and TPO commercial-grade roofs, this property is engineered for durability and long-term value. Windsor Green is a private gated enclave on a lovely hilltop. The location is unmatched for those who enjoy boating, golfing or a more relaxed pace of life while staying close to shopping, dining and top-tier healthcare facilities. Restyle the classic architecture with your personal vision and taste. Enjoy the good life in a natural setting, refined Florida living, built for comfort, flexibility and long-term potential.

Listing Status:

Active

Date Added:

November 7, 2025 at 06:00AM

Listing Office:

PREMIER SOTHEBYS INT'L REALTY : 407-581-7888

Listing Agent:

Keith Caulk : 352-431-8539

MLS ID:

G5104061

Interior

• General: Built-in FeaturesCeiling Fans(s)Central VaccumHigh CeilingsPrimary Bedroom Main FloorSolid Surface CountersSolid Wood CabinetsSplit BedroomStone CountersWalk-In Closet(s)Window Treatments
• Rooms: Bonus RoomDen/Library/OfficeFormal Dining Room Separate
• Appliances: Built-In OvenConvection OvenCooktopDishwasherDisposalDryerElectric Water HeaterMicrowaveRange HoodRefrigeratorWasherWine Refrigerator
• Laundry: Electric Dryer HookupInsideLaundry RoomWasher Hookup
• Flooring: Tile
• A/C: Central Air
• Heating: CentralElectricZoned
• Fireplace: ElectricLiving RoomFireplace

Exterior

• General: French DoorsLighting
• Style: French Provincial
• Other Structures: Additional Single Family HomeFinished RV PortGuest HouseRear PorchCovered
• Parking: Circular DrivewayDrivewayElectric Vehicle Charging Station(s)Garage Door OpenerOversizedRV Garage

Construction

• Roofing: Membrane
• Windows: Double Pane Windows
• General: BlockConcreteStuccoOneSlabStem Wall

Location

• Road/Access: Asphalt
• HOA Amenities: Gated206.0Monthly
• Originating MLS: Stellar MLS
• County: Lake

Lot

• Zoning: R-1WINDSOR GREEN PHASE 1 PB 61 PG 3-8 LOT 13 ORB 6194 PG 67810-18-24-0200-000-01300
• View: GardenTrees/Woods

Utilities

• Utilities: Electricity ConnectedPublic
• Water: PrivateWell
• Sewer: Private Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple

This listing courtesy of Keith Caulk, PREMIER SOTHEBYS INT'L REALTY