Gabriella Massaro

Gabriella Massaro Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

$2,135,000.00
39851 & 39855 DARLINGTON AVENUE, LADY LAKE, FL - 32159
5 beds
5.5 baths
5,278 sqft
$2,135,000.00
39851 & 39855 DARLINGTON AVENUE, LADY LAKE, FL - 32159
Gabriella Massaro
$2,135,000.00
5 beds
5.5 baths
5,278 sqft
39851 & 39855 DARLINGTON AVENUE, LADY LAKE, FL - 32159
For Sale
Photo 1
  • Built in 2023
  • 6 garage spaces
  • $404.51/sqft
  • Lot size: 2.35 acres
  • 142 days on market

Set on 2.35 private acres on a quiet hilltop within the gated community of Windsor Greene, this rare Central Florida offering brings together space, structure, and flexibility—designed for those with multiple vehicles, RVs or boats, and a need for multi-generational living, with two residences and a substantial detached storage garage. The property is organized for both independence and function, offering a combination that is increasingly difficult to find. The main residence spans 3,426 square feet with three en-suite bedrooms and 3.5 baths, arranged in a thoughtful layout that is open yet naturally defined, allowing spaces to flow easily from one room to the next. Interior features include 12-foot ceilings, 8-foot solid core doors, custom walkin closets, and large-format porcelain slab flooring with an onyx finish throughout. The kitchen connects seamlessly to the main living area, finished with high-grade stone surfaces and durable materials. A porcelain slab fireplace anchors the living room, with French doors opening to the lanai and a newly planted tree line that enhances privacy and green space. The second residence offers 1,720 square feet with a split floor plan, open living area, and an attached two-car garage suitable for larger vehicles or trucks. It provides true separation for extended family, guests, rental use, or a dedicated work-from-home environment. Both homes include well-designed laundry rooms with a focus on everyday function. A defining feature of the property is the detached garage structure, built with 16-foot ceilings, commercial-grade doors rated to 150 mph, and full insulation. This space accommodates RVs, boats, multiple vehicles, or equipment with ease—purpose-built for collectors, hobbyists, or those who require secure, substantial storage. Constructed by the owner with concrete block and finished with TPO commercial-grade roofing, the property reflects a clear focus on strength, durability, and long-term performance. Set within a private gated enclave and positioned on gentle elevation, the setting is quiet and intentionally removed, yet highly accessible—just minutes to The Villages, approximately 50 minutes to Ocala, and under an hour to Orlando International Airport and major attractions.

  • Directions: From HWY 441 turn on Lemon St, L on Lake Griffin Rd, L on Darlington Ave, home on left.
  • County: Lake
  • Geo subdivision: WINDSOR GREEN

Nearby Schools

Villages Elem of Lady Lake

Carver Middle

Leesburg High

Features

Financial

Let's get in touch!

Gabriella Massaro

Gabriella Massaro

Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

See also

For Sale
12730 E HIGHWAY 25, OCKLAWAHA, FL - 32179
$1,950,000.00
6 bds
6.5 ba
4,954 sqft
12730 E HIGHWAY 25, OCKLAWAHA, FL - 32179
For Sale
1568 BLACK LAKE DRIVE, THE VILLAGES, FL - 32162
$2,250,000.00
4 bds
4.5 ba
4,654 sqft
1568 BLACK LAKE DRIVE, THE VILLAGES, FL - 32162
For Sale
683 KRIETEMEYER PATH, THE VILLAGES, FL - 32163
$2,000,000.00
4 bds
3.0 ba
3,345 sqft
683 KRIETEMEYER PATH, THE VILLAGES, FL - 32163
Stellar MLS
  • Source: Stellar MLS
  • MLS #: G5104061
Listing updated: March 29, 2026 at 10:48PM
Listing provided by: Keith Caulk, PREMIER SOTHEBYS INT'L REALTY
Last checked 3 days ago
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