
39851 & 39855 DARLINGTON AVENUE, LADY LAKE, FL, 32159
Active2 days on marketListed Nov 5, 2026MLS #OM734370
About this home
39851 & 39855 DARLINGTON AVENUE
Privately situated on 2.35 elevated acres within the gated community of Windsor Greene, this distinctive Central Florida estate presents an exceptional combination of architectural refinement, two independent residences and substantial accommodations for automotive collections, recreational vehicles and boats. Thoughtfully designed and constructed with an emphasis on quality, versatility and lasting performance, the property offers a rare opportunity to enjoy expansive living spaces within a secluded hilltop setting. The 3,426-square-foot main residence showcases sophisticated finishes and carefully considered architectural details. Soaring 12-foot ceilings, 8-foot solid-core doors and large-format porcelain slab flooring with an onyx finish establish a cohesive interior aesthetic. Three generously proportioned en-suite bedrooms provide private accommodations, complemented by a half bath and custom walk-in closets. The flowing floor plan connects the principal living areas while maintaining definition between spaces. In the kitchen, premium stone surfaces and quality materials complement the home's contemporary design. A porcelain slab fireplace creates a striking focal point in the living room, while French doors open to the lanai and landscaped grounds. The planted tree line provides an additional layer of natural privacy. The separate 1,720-square-foot residence offers a complete living environment with two bedrooms, two baths, a full kitchen, dedicated living and dining areas, a laundry room and an attached two-car garage designed to accommodate larger vehicles. Its split floor plan provides flexibility for extended family, guests or other residential needs while maintaining separation from the main home. An extraordinary feature of the estate is the approximately 1,782-square-foot detached garage, measuring 54 by 33 feet. Built for substantial vehicle and equipment storage, this fully insulated structure features 16-foot ceilings and commercial-grade garage doors rated to withstand winds of up to 150 mph. The generous dimensions accommodate a variety of automotive, boating and recreational storage requirements. Owner-built with concrete block construction, all three structures feature a commercial-grade PTO weld membrane roof, reflecting a consistent commitment to durable materials and construction standards. The property's gently elevated setting, established landscaping and gated surroundings contribute to its private estate atmosphere. Conveniently located near The Villages, with access to Ocala, Orlando International Airport and Central Florida's recreational destinations, this property brings together refined residential living, independent accommodations and specialized storage facilities on 2.35 acres.
Facts & features
The home at a glance
5
Bedrooms
5.5
Bathrooms
5,146
Sqft
2.35 ac
Lot size
8
Garage
2023
Year built
One
Levels
$360
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record and the real association fee — not generic estimates.
$13,933 /mo · 10% down Conventional, 30-yr fixed at 7.5%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:

Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$13,933/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Can I afford this home? → See what you can comfortably afford from your income, debts and savings.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
$/sqft vs Lady Lake actives
$360 vs $207
Days on market
2 vs 84 typical
Where $360/sqft sits among the 152 Lady Lake actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Lady Lake
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Lady Lake. See the full Lady Lake guide →
LADY LAKE 32159 — neighborhood snapshot
Population
32,107
Median age
69
Median income
$58,518
Median home value
$289,600
Avg household
1.83
Households w/ children
1,450
For the school run
Lake County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Lady Lake market
$315K → $307K
Lady Lake median sold, yr/yr
97.2%
Sale-to-list ratio (12 mo)
81 of 152
Lady Lake actives have cut their price
Median sold price, Lady Lake, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 497% above the LADY LAKE 32159 median. See the full Lady Lake market guide →
Paper trail
This home's history
Reality check
What actually sold near 39851 & 39855 DARLINGTON AVENUE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Mar ’26$500,000
2901 GRIFFIN VIEW DRIVE
6 bd · 5 ba · 3,752 sqft · $133/sqft · 175 DOM
Sold · Dec ’25$755,000
3000 PINE GROVE LANE
4 bd · 4.5 ba · 3,294 sqft · $229/sqft · 5 DOM
Sold · Nov ’25$760,000
1921 SMITTY ROAD
5 bd · 3 ba · 3,090 sqft · $246/sqft · 504 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Seth Cabrera - Rothschild
Realtor · CENTURY 21 Edge
Tours, negotiation, and every question about 39851 & 39855 DARLINGTON AVENUE — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 39851 & 39855 DARLINGTON AVENUE — before you fall in love.
See it in person
Schedule a tour
Live availability from Seth's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
39851 & 39855 DARLINGTON AVENUE FAQs
What would the monthly payment be for 39851 & 39855 DARLINGTON AVENUE?+
With 10% down on a 30-year Conventional loan at 7.5%, the all-in payment lands around $13,933/mo — principal and interest, the actual property-tax bill, the $206/mo association fee and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
How much are the HOA fees at 39851 & 39855 DARLINGTON AVENUE?+
The association fee works out to $206 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 39851 & 39855 DARLINGTON AVENUE?+
The most recent tax bill on record (2025) was $14,778. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 39851 & 39855 DARLINGTON AVENUE?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Lady Lake?+
At $1,850,000, this home is listed about 432% above the Lady Lake median of $347,700. The market section on this page shows how the area is trending.
Which schools are assigned to 39851 & 39855 DARLINGTON AVENUE?+
The Villages Elementary Of Lady Lake School (elementary), Carver Middle School (middle), Leesburg High School (high) — Lake County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$1,850,000 runs 497% above the LADY LAKE 32159 median — but at 5,146 sqft it's also nearly 3 times the size of the typical Lady Lake listing.
02Garden & Trees/Woods views
The garden and trees/woods view is part of what you're buying — views hold value independently of the structure.
03Fresh on the market
Only 2 days on market in a Lady Lake market that averages 84 — if it fits, move quickly.
Keep looking
Similar homes nearby
Listing courtesy of PREMIER SOTHEBY'S INTERNATIONA · Angela Rose. MLS #OM734370.
IDX information is provided exclusively 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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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