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Jamie Deihl
REALTOR®
(719) 468-9744
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39851 & 39855 Darlington Avenue, Lady Lake, FL 32159

$2,135,000

54 Total Photos [Click to View All]

Property Description

Looking for RV/Boat storage, Mutli-generational living? 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.

39851 & 39855 Darlington Avenue | MLS# G5104061

This single family home located at 39851 & 39855 Darlington Avenue, Lady Lake, FL 32159 is currently listed for sale with an asking price of $2,135,000. This property was built in 2023 and has 5 bedrooms and 5 full and 1 partial baths with 5278 sq. ft. & 39855 Darlington Avenue is located in the WINDSOR GREEN subdivision. Search WINDSOR GREEN real estate on jamiedeihl.watsonrealtycorp.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air
Garage: 6 car attached
Heating: Central, Electric, Zoned
Home Style: French Provincial
Lot Size: 2.35 Acres
Roof Type: Membrane
Stories: 1.0
Taxes: $14,853
Year Built: 2023
Square Feet: 5,278

Amenities

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
French Doors
Lighting

Feature Descriptions

Additional Rooms: Bonus Room, Den/Library/Office, Formal Dining Room Separate
Appliances: Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range Hood, Refrigerator, Washer, Wine Refrigerator
Association Amenities: Gated
Community Features: Deed Restrictions, Gated Community - No Guard
Days on Site: 123
Directions: From HWY 441 turn on Lemon St, L on Lake Griffin Rd, L on Darlington Ave, home on left.
Exterior: Block, Concrete, Stucco
Fireplace: Electric, Living Room
Fireplace Y/N: Yes
Flood Zone Code: X
Flooring: Tile
Foundation: Slab, Stem Wall
HOA Fee: 206/ Monthly
HOA Y/N: Yes
Home Warranty Y/N: No
Listing Terms: Cash, Conventional, VA Loan
Lot: Cleared, In County, Landscaped, Private, Street Dead-End, Paved
Lot Dimensions: 2.35
Number of Septics: 1
Number of Wells: 1
Other Equipment: Irrigation Equipment
Other Structures: Additional Single Family Home, Finished RV Port, Guest House
Ownership: Fee Simple
Parking: Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Oversized, RV Garage
Parking Notes: Circular Driveway, Driveway, Electric Vehicle Chargi
Patio/Porch: Covered, Rear Porch
Pets Allowed: Yes
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Security: Security System, Security System Owned
Sewer: Private Sewer
Showing Instructions: 24 Hour Notice, Appointment Only, Listing Agent Must Accompany, ShowingTime
Special Sale Provisions: None
Utilities: Electricity Connected, Public
Water: Private, Well
Water Access Y/N: No
Windows: Double Pane Windows
Zoning: R-1

Local Schools

High School: Leesburg High
Middle School: Carver Middle
Elementary School: Villages Elem of Lady Lake

Listed By / Shown By

Listed By

Agency Name: PREMIER SOTHEBYS INT'L REALTY
Agency Contact: 407-581-7888

Shown By

Agent Name: Jamie Deihl
Agent Phone: (719) 468-9744
Agency Title: Watson Realty Corp., REALTORS ®

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Estimated Payment

$ 12,155.75 per month $10,295.29 Principal & Interest $1,237.75 Property Tax $622.71 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 03/10/2026. The listing information on this page last changed on 03/10/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 03/10/2026 12:42:09 AM EST) or GAMLS (last updated Mon 03/09/2026 11:14:58 PM EST) or Stellar MLS (last updated Tue 03/10/2026 12:29:11 AM EST) or SPC MLS (last updated Mon 03/09/2026 11:20:30 PM EST) or Martin MLS (last updated Mon 03/09/2026 11:38:19 PM EST) or Indian River MLS (last updated Mon 03/09/2026 11:30:27 PM EST) or Daytona MLS (last updated Mon 03/09/2026 11:36:51 PM EST) or Northeast Florida MLS (last updated Tue 03/10/2026 12:18:46 AM EST) or Beaches MLS (last updated Tue 03/10/2026 12:35:40 AM EST) or BORMLS (last updated Mon 03/09/2026 11:15:20 PM EST) or Golden Isles MLS (last updated Mon 03/09/2026 11:26:41 PM EST) or Amelia/Nassau MLS (last updated Mon 03/09/2026 11:25:21 PM EST) or Dixie Gilchrist Levy MLS (last updated Mon 03/09/2026 11:42:28 PM EST). Real estate listings held by brokerage firms other than Watson Realty Corp., REALTORS ® may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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