NOT LISTED FOR SALE

9508 Windy Ridge Rd Windermere, FL 34786

Estimated Value: $2,276,000 - $10,693,171

6 Beds
14 Baths
20,865 Sq Ft
$311/Sq Ft Est. Value

About This Home

Discover this Perfectly positioned Georgian Estate situated on 12 acres (additional 6 acres available) of lakefront property with meticulously manicured grounds. This walled and gated compound includes approx 614 feet of pristine lake frontage and panoramic views on Lake Down of the Butler Chain of Lakes. The magnificent sprawling primary residence pairs classic Georgian architecture with modern amenities to achieve the ultimate lakeside retreat. Immediately you are greeted by the finest materials and finishes inside an elegant entryway which opens into a grand interior boasting a floating mahogany staircase, marble floors and paneled walls all framed by stunning Murano chandeliers. An art gallery leads into a spacious living room lined with mahogany walls and boasts expansive waterfront vistas. The gourmet kitchen is a chefs delight featuring a salamander for warming and broiling, two double convection ovens, a large commercial icemaker and a commercial refrigerator and freezer. Downstairs also includes one of two owner's suites along with a spacious library-lounge or possible 6th bedroom suite. Dual staircases or a commercial Thyssenkrupp elevator offer access to the second level featuring four more expansive bedroom suites, including the main owner's retreat, and an 85-foot parlor highlighted by 20-foot ceilings, bookshelves and a wet bar the perfect venue for hosting family and friends. A screened porch captures spectacular southern lakefront views and nightly fireworks displays from Walt Disney World. Connected by a breezeway, a grand rustic lodge comprised of 5,600 square feet and equipped with a large bar, catering kitchen, entertainment hall and locker facilities offer limitless potential. The outdoors is the ultimate playground complete with a Junior Olympic pool and spa while a fountain and light features await. Additional amenities include a 3,800-square-foot storage building with 20-foot ceilings, staff quarters with 576 square feet of living space, a patio area and courtyard and a 4,000-square-foot paneled garage with separate office, guest apartment and 20-foot ceilings for the auto aficionados treasured collection with 3 separate garages including room for a full-size motor coach and car collection. Situated in one of Central Floridas most sought-after locations, this truly exceptional estate epitomizes luxury, privacy and sophistication to offer an enviable lakefront lifestyle.

Ownership History

Date Name Owned For Owner Type

Purchase Details

Closed on
Jun 18, 2010
Sold by
Samanthas Windy Ridge Llc
Bought by
Gelman Jeffrey B
Current Estimated Value
$6,484,586

Purchase Details

Closed on
Apr 15, 2005
Sold by
Via Verde Llc
Bought by
Samanthas Windy Ridge Llc

Purchase Details

Closed on
Sep 18, 2003
Sold by
Ansari Tahir S and Ansari Jasmine Eslait
Bought by
Via Verde Llc

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$2,100,000
Interest Rate
6.33%
Mortgage Type
Purchase Money Mortgage

Purchase Details

Closed on
Oct 29, 1998
Sold by
Cafaro John J
Bought by
Ansari Tahir S and Ansari Jasmine E

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$750,000
Interest Rate
6.61%
Mortgage Type
New Conventional

Purchase Details

Closed on
Aug 16, 1996
Sold by
Cafaro John J
Bought by
Joseph George P and Joseph Sandra K

Purchase Details

Closed on
Aug 7, 1996
Sold by
Leahy Cornelia L and Lyle Cornelius R
Bought by
Cafaro John J
Source: Public Records

Range of Values:

--
Value Increase
--
Percent Increase
--
Adjusted for Inflation
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Average Value
Not Available
List Price
Sold Price
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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Purchase History

Date Buyer Sale Price Title Company
Gelman Jeffrey B -- Attorney
Samanthas Windy Ridge Llc $6,000,000 --
Via Verde Llc $2,500,000 --
Ansari Tahir S $1,400,000 --
Joseph George P $636,000 --
Joseph George P $100 --
Cafaro John J $100 --
Source: Public Records

Mortgage History

Date Status Borrower Loan Amount
Previous Owner Via Verde Llc $2,100,000
Previous Owner Cafaro John J $750,000
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft
11/30/2025 11/30/25 Price Changed $19,995,000 -13.0% $958 / Sq Ft
10/30/2025 10/30/25 For Sale $22,995,000 -- $1,102 / Sq Ft

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $167,320 $10,496,622 -- --
2024 $151,649 $10,200,799 -- --
2023 $151,649 $9,624,576 $0 $0
2022 $147,553 $9,344,249 $0 $0
2021 $145,965 $9,072,086 $0 $0
2020 $139,296 $8,946,830 $0 $0
2019 $144,106 $8,745,679 $0 $0
2018 $143,162 $8,582,609 $0 $0
2017 $141,763 $9,064,612 $4,600,000 $4,464,612
2016 $141,772 $8,932,764 $4,600,000 $4,332,764
2015 $144,100 $8,837,130 $4,500,000 $4,337,130
2014 -- $8,265,519 $4,000,000 $4,265,519
Source: Public Records

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