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$2,535,717

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 5 Full Baths
  • 1 Partial Bath
  • 5,278 Sq. Ft.
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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.

Full Property Details for 39851 & 39855 Darlington Ave

General

  • Price: $2,535,717
  • HOA FEE: $206/month
  • Taxes: $14,853 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: G5104061
  • Updated: 11/11/2025
  • Added to Site: 73 day(s) ago

Rental Information

  • Min. Lease: 1 Month

Interior

  • Number of Rooms: 13
  • Interior Features: Built-in Features, Ceiling Fan(s), Central Vacuum, High Ceilings, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Walk-In Closet(s), Window Treatments
  • Fireplace: Yes
  • Fireplace(s): Electric, Living Room
  • Appliances: Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range Hood, Refrigerator, Washer, Wine Refrigerator
  • Flooring: Porcelain Tile

Rooms

Bathrooms

  • Total Bathrooms: 6
  • Full Bathrooms: 5
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup

Additional Information

  • Shared Amenities: Gated
  • Security/Safety: Security System, Security System Owned

Exterior

  • Exterior Features: French Doors, Irrigation System, Lighting
  • Deck/Patio: Covered, Rear Porch
  • Porch/Patio/Deck: Covered, Rear Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 6
  • Covered Spaces: 6
  • Parking Features: Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Oversized, RV Garage

Location

  • Area: 32159 - Lady Lake (The Villages)
  • County: Lake
  • Development Name: 32159 - Lady Lake (The Villages)
  • Subdivision: WINDSOR GREEN
  • Driving Directions: From HWY 441 turn on Lemon St, L on Lake Griffin Rd, L on Darlington Ave, home on left.
  • Direction Faces: East

School Information

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

Community

  • Community Name: 32159 - Lady Lake (The Villages)
  • Community Features: Deed Restrictions, Gated Community - No Guard
  • Optional Amenities: Gated
  • Association: Yes
  • Assoc. Name: Windsor Green Prop. Owners Association

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric, Zoned

Utilities

  • Sewer: Private Sewer
  • Water: Private, Well
  • Utility Description: Electricity Connected, Public

Structural Information

  • Architectural Info: French Provincial
  • Architectural Style: French Provincial
  • Exterior Const.: Block, Concrete, Stucco
  • Roof: Membrane
  • Windows: Double Pane Windows
  • Stories/Levels: One
  • Square Feet: 5,278
  • Sq. Ft. Source: Owner
  • Year Built: 2023

Additional Structures

  • Other Structures: Additional Single Family Home, Finished RV Port, Guest House

Lot Features

  • Property View: Garden, Trees/Woods
  • Lot Size (Acres): 2.35
  • Lot Size (Sq. Ft.): 102,366
  • Lot Size: 2.35
  • Frontage: Street Dead-End, Street Paved, Private Road
  • Street/Road Desc.: Paved, Asphalt

Financial Considerations

  • Association Fee: $206
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $14,853.65
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: WINDSOR GREEN PHASE 1 PB 61 PG 3-8 LOT 13 ORB 6194 PG 678
  • Flood Zone Info: X
  • APN: 101824020000001300
  • Property ID: 101824020000001300

Listed by Premier Sothebys Int'l Realty and Premier Sotheby's International Realty

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Listing agents

— 39851 & 39855 Darlington Ave —

  • Premier Sothebys Int'l Realty

  • Premier Sotheby's International Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 39851 & 39855 Darlington Ave

School District:Lake County School District
NameGradesDistance
The Villages Elementary Of Lady Lake School
695 Rolling Acres Road, Lady Lake, FL 32159
PK-51.9 mi
Carver Middle School, Leesburg, FL
1200 Beecher Street, Leesburg, FL 34748
6-87 mi
Leesburg High School
1401 Yellow Jacket Way, Leesburg, FL 34748
9-128.4 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 39851 & 39855 Darlington Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/07/2025
Listed
$2,535,717
1850.55%
MLS
2/24/2022
Sold
$130,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 39851 & 39855 Darlington Ave

Year
Property Taxes
Change
Tax Assessment
Change
2024
$14,854
546%
$982,430
1038%
2023
$2,300
157%
$86,363
—
2022
$896
-4%
$86,363
—
2021
$936
—
$86,363
31%
2021
$936
62%
$65,800
87%
2018
$576
1%
$35,250
—
2017
$573
-3%
$35,250
—
2019
$590
11%
$35,250
—
2016
$533
-28%
$35,250
-25%
2015
$736
-1%
$47,000
—
2014
$742
6%
$47,000
—
2013
$699
—
$47,000
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Premier Sothebys Int'l Realty and Premier Sotheby's International Realty

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39851 & 39855 Darlington Avenue, Lady Lake, FL 32159 (MLS# G5104061) is a Single Family property with 5 bedrooms, 5 full bathrooms and 1 partial bathroom. 39851 & 39855 Darlington Avenue is currently listed for $2,535,717 and was received on November 07, 2025. Want to learn more about 39851 & 39855 Darlington Avenue? Do you have questions about finding other Single Family real estate for sale in Lady Lake? You can browse all Lady Lake real estate or contact a Coldwell Banker agent to request more information.

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