39851 & 39855 Darlington Avenue, Lady Lake, FL 32159
For Sale $2,535,717
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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.
Built-in Features
Ceiling Fans(s)
Central Vaccum
High Ceilings
Primary Bedroom Main Floor
Solid Surface Counters
Solid Wood Cabinets
Split Bedroom
Stone Counters
Walk-In Closet(s)
Window Treatments
Gated
Taxes: $14.00
Tax Year: 2024
HOA Fee 1: $206.00
HOA Frequency 1: Monthly
Condo Fee Frequency: Monthly
French Doors
Lighting
Built-In Oven
Convection Oven
Cooktop
Dishwasher
Disposal
Dryer
Electric Water Heater
Microwave
Range Hood
Refrigerator
Washer
Wine Refrigerator
Garden
Trees/Woods
Elementary School: Villages Elem Of Lady Lake
Middle School: Carver Middle
Junior High: Carver Middle
High School: Leesburg High
MLS Area: 32159 - Lady Lake (The Villages)
Price per Square Feet: $480.43
Water: Private, Well
Lot Desc.: Cleared, In County, Landscaped, Private, Street Dead-End, Paved
Construction: Block, Concrete, Stucco
Date Listed: 2025-11-07 19:29:54
Pool: No
Private Spa: No
Windows: Double Pane Windows
Parking: Circular Driveway, Driveway, Electric Vehicle Charging Station(S), Garage Door Opener, Oversized, Rv Garage
Garage Spaces: 6
Flooring: Tile
Roof: Membrane
Heating: Central, Electric, Zoned
Cooling: Central Air
Pets: Yes
Sewer: Private Sewer
Amenities: Gated
Listing Courtesy Of: Premier Sothebys Intl Realty
kacaulkrealtor@gmail.com
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.
Property Details
Price: $2,535,717
Sq Ft: 5,278
($480 per sqft)
Bedrooms: 5
Bathrooms: 5
Partial Baths: 1
City: Lady Lake
County: Lake
Type: Single Family Reside
Development: Windsor Green
Acres: 2.35
Virtual Tour/Floorplan: View
Year Built: 2023
Listing Number: G5104061
Status Code: A-Active
Taxes: $14.00
Tax Year: 2024
Garage:
6
Pets Allowed: Yes
Interior Features:
Built-in Features
Ceiling Fans(s)
Central Vaccum
High Ceilings
Primary Bedroom Main Floor
Solid Surface Counters
Solid Wood Cabinets
Split Bedroom
Stone Counters
Walk-In Closet(s)
Window Treatments
Amenities:
Gated
Financial Information:
Taxes: $14.00
Tax Year: 2024
HOA Fee 1: $206.00
HOA Frequency 1: Monthly
Condo Fee Frequency: Monthly
Exterior Features:
French Doors
Lighting
Equipment:
Built-In Oven
Convection Oven
Cooktop
Dishwasher
Disposal
Dryer
Electric Water Heater
Microwave
Range Hood
Refrigerator
Washer
Wine Refrigerator
View:
Garden
Trees/Woods
School Information:
Elementary School: Villages Elem Of Lady Lake
Middle School: Carver Middle
Junior High: Carver Middle
High School: Leesburg High
Additional Information:
MLS Area: 32159 - Lady Lake (The Villages)
Price per Square Feet: $480.43
Water: Private, Well
Lot Desc.: Cleared, In County, Landscaped, Private, Street Dead-End, Paved
Construction: Block, Concrete, Stucco
Date Listed: 2025-11-07 19:29:54
Pool: No
Private Spa: No
Windows: Double Pane Windows
Parking: Circular Driveway, Driveway, Electric Vehicle Charging Station(S), Garage Door Opener, Oversized, Rv Garage
Garage Spaces: 6
Flooring: Tile
Roof: Membrane
Heating: Central, Electric, Zoned
Cooling: Central Air
Pets: Yes
Sewer: Private Sewer
Amenities: Gated
Map of 39851 & 39855 Darlington Avenue, Lady Lake, FL 32159
Listing Courtesy Of: Premier Sothebys Intl Realty
kacaulkrealtor@gmail.com