How many active listings are available in this area?

There are 9 active listings in this area.

What is the average listing price in this area?

The average listing price for the displayed results is $3,369,667.

Home Florida Lake Bessie

Lake Bessie

Looking for lakefront homes on Lake Bessie? Find lake estate for sale here. Located in Orange County, Florida. Discover the best lake front listings - properties, land, and acreage to build your dream lake house, cottage or cabin on. Search for an agent who specializes in lake property to help you buy or sell a home.

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Showing 1-9 of 9 Homes For Sale

For Sale

Set along Isleworth's signature 12th fairway, this fully - photo 1

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$5,500,000

4 Beds | 5.0 Baths | 4,330 Sqft

Lake Bessie

5138 FAIRWAY OAKS DR, Windermere, FL, 34786

Set along Isleworth's signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club--recognized among the...

Ad#: 7627798 • Added: 04/25/2026 • Updated: 05/26/2026

For Sale

Set within the gates of renowned Isleworth, this beautifully - photo 1

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$5,300,000

6 Beds | 7.0 Baths | 4,665 Sqft

Lake Bessie

5199 LATROBE DR, Windermere, FL, 34786

Set within the gates of renowned Isleworth, this beautifully reimagined golf-front estate presents an exceptional opportunity to experience refined Central Florida living at its finest. Perfectly...

Ad#: 7783414 • Added: 05/28/2026 • Updated: 05/28/2026

For Sale

Positioned along the stunning 4th fairway of the renowned - photo 1

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$3,900,000

4 Beds | 5.0 Baths | 5,301 Sqft

Lake Bessie

5151 LATROBE DR, Windermere, FL, 34786

Positioned along the stunning 4th fairway of the renowned Isleworth Golf & Country Club, this exceptional single-story estate offers four bedrooms and more than 5,300 square feet of meticulously...

Ad#: 7450005 • Added: 03/20/2026 • Updated: 05/26/2026

For Sale

Situated on the 6th fairway along the course of Isleworth Golf & - photo 1

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Situated on the 6th fairway along the course of Isleworth Golf & - photo 40

$3,390,000

4 Beds | 5.0 Baths | 3,365 Sqft

Lake Bessie

5050 ISLEWORTH COUNTRY CLUB DR, Windermere, FL, 34786

Situated on the 6th fairway along the course of Isleworth Golf & Country Club, this updated golf front sparkles with new porcelain tile throughout and modern chandeliers. This single-story residence...

Ad#: 7113455 • Added: 01/10/2026 • Updated: 05/26/2026

For Sale

Set on an elevated corner homesite within Isleworth, this - photo 1

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$2,999,000

4 Beds | 6.0 Baths | 4,706 Sqft

Lake Bessie

5073 LATROBE DR, Windermere, FL, 34786

Set on an elevated corner homesite within Isleworth, this four-bedroom residence presents a unique opportunity to secure a coveted address in one of Central Florida's most distinguished private golf...

Ad#: 7839306 • Added: 06/05/2026 • Updated: 06/06/2026

For Sale

Architecturally refined and thoughtfully designed, this custom - photo 1

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$2,175,000

6 Beds | 6.0 Baths | 5,031 Sqft

Lake Bessie

713 MAIN ST, Windermere, FL, 34786

Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere with...

Ad#: 6992662 • Added: 12/19/2025 • Updated: 05/26/2026

For Sale

Modern style blends with Windermere charm. This totally - photo 1

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$1,198,000

4 Beds | 4.0 Baths | 2,791 Sqft

Lake Bessie

109 E 12TH AVE, Windermere, FL, 34786

Modern style blends with Windermere charm. This totally renovated home is located just steps from Lake Bessie in the Town of Windermere. Set on a beautifully landscaped corner lot with no HOA, this...

Ad#: 7572665 • Added: 04/15/2026 • Updated: 05/20/2026

For Sale

Set on a prominent corner lot in one of Windermere's most - photo 1

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$965,000

4 Beds | 3.0 Baths | 3,516 Sqft

Lake Bessie

1002 OAKDALE ST, Windermere, FL, 34786

Set on a prominent corner lot in one of Windermere's most sought-after enclaves, this thoughtfully updated residence blends timeless character with modern upgrades, enormous walk out bottom level...

Ad#: 7567354 • Added: 04/14/2026 • Updated: 06/23/2026

Waterfront Sale Pending

Under contract-accepting backup offers. Within the gates of the - photo 1

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$4,900,000

5 Beds | 5.0 Baths | 5,548 Sqft

Lake Bessie

5036 LATROBE DR, Windermere, FL, 34786

Under contract-accepting backup offers. Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living...

Ad#: 6686619 • Added: 10/06/2025 • Updated: 10/06/2025

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