
9508 WINDY RIDGE ROAD, WINDERMERE, FL, 34786
Active52 days on marketListed Jun 2, 2026MLS #O6411343
About this home
9508 WINDY RIDGE ROAD
Showcasing Central Florida’s most iconic lakefront estate: an 18-acre compound with 614 feet of pristine frontage on Lake Down on The Butler Chain of Lakes. The Windy Ridge Estate is comprised of multiple buildings spanning 51,000 square feet of space including an expansive 20,333 square-foot Georgian-style Plantation mansion that is a showplace residence with generous luxurious spaces, classic elegance, and the ultimate in security and serenity. The walled entry opens to a grand foyer with a floating mahogany staircase, marble floors, paneled walls, and Murano chandeliers. An art gallery leads to a spacious living room featuring rich mahogany millwork and expansive lake vistas. Gourmet kitchen: salamander, dual double convection ovens, commercial icemaker, full-size refrigerator, and freezer. The main level includes one of two owners' suites, plus a library-lounge or a possible sixth bedroom. Dual staircases or a Thyssenkrupp elevator provide access to the upper level, which features four-bedroom suites, including the primary retreat. An 85-foot parlor with 20-foot ceilings, built-in bookshelves, and a wet bar provide a dramatic entertaining space. Screened porch captures southern lake views and Disney fireworks. Breezeway connects to a 5,600 SF rustic lodge with a bar, catering kitchen, entertainment hall, and locker facilities. Outdoor amenities: Junior Olympic pool, spa, decorative fountain, architectural lighting, direct lake access. The vast and open water location offers an ideal space for seaplane arrivals and departures. Additional structures include a 4,000 SF paneled garage with 20-foot ceilings, an office, and a guest apartment; a 3,800 SF storage building; three separate garages accommodating motor coach and car collection; and staff quarters with a private courtyard. A rare fusion of Southern grandeur, lakefront serenity, and equestrian potential—without any interference of an HOA. Truly a legacy compound crafted for those who demand the extraordinary.
Facts & features
The home at a glance
7
Bedrooms
13
Bathrooms
51,000
Sqft
18.16 ac
Lot size
12
Garage
2011
Year built
Two
Levels
$588
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 — not generic estimates.
$186,836 /mo · 10% down Conventional, 30-yr fixed at 6%
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
$186,836/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.
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 N/A
$588 vs $286
Days on market
52 vs 32 typical
Where $588/sqft sits among the 229 homes for sale in N/A
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 Windermere
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Windermere. See the full Windermere guide →
WINDERMERE 34786 — neighborhood snapshot
Population
43,700
Median age
37.9
Median income
$131,409
Median home value
$621,300
Avg household
2.9
Households w/ children
6,277
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Windermere market
$839K → $1.0M
Windermere median sold, yr/yr
96.4%
Sale-to-list ratio (12 mo)
109 of 229
N/A have cut their price
Median sold price, Windermere, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 3650% above the WINDERMERE 34786 median. See the full Windermere market guide →
Paper trail
This home's history
Reality check
What actually sold near 9508 WINDY RIDGE ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Dec ’25$357,275
10699 SW 76TH · same community
4 bd · 3 ba · 13,676 sqft · $26/sqft · 0 DOM
Sold · Dec ’25$3,721,000
5303 NW 73RD TERRACE · same community
5 bd · 5.5 ba · 6,930 sqft · $537/sqft · 0 DOM
Sold · Dec ’25$573,000
2202 OLD TAVARES ROAD · same community
4 bd · 4.5 ba · 3,337 sqft · $172/sqft · 109 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
Eric Chery
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 9508 WINDY RIDGE ROAD — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 9508 WINDY RIDGE ROAD — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Eric's phone and CRM.
Straight answers
9508 WINDY RIDGE ROAD FAQs
What would the monthly payment be for 9508 WINDY RIDGE ROAD?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $186,836/mo — principal and interest, the actual property-tax bill 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.
What are the property taxes on 9508 WINDY RIDGE ROAD?+
The most recent tax bill on record (2024) was $162,563. 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 9508 WINDY RIDGE ROAD?+
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 Windermere?+
At $30,000,000, this home is listed about 2629% above the Windermere median of $1,099,500. The market section on this page shows how the area is trending.
Which schools are assigned to 9508 WINDY RIDGE ROAD?+
Windermere Elementary (elementary), Olympia High (high), Gotha Middle (middle) — Orange 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
$30,000,000 runs 3650% above the WINDERMERE 34786 median — but at 51,000 sqft it's also nearly 16 times the size of the typical Windermere listing.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Strong assigned schools
Windermere Elementary, Olympia High, Gotha Middle — Windermere Elementary rates 5 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of STOCKWORTH REALTY GROUP · Rob Rahter. MLS #O6411343.
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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