Exclusive listings. Exceptional living.
Exclusive listings. Exceptional living.
About Lakeside Realty Windermere
Luxury Modern Home in Windermere

About Lakeside Realty Windermere

Lakeside Realty Windermere is a boutique real estate office in downtown Windermere. Since 2006, founders Loren Williams and Kevin Sullivan have built a team known for deep knowledge of Southwest Orange County and beyond. From lakefront estates on the Butler Chain to new homes in Horizon West, our focus is simple: putting clients' needs first.

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500+
Properties Sold
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1000+
Satisfied Clients
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25+
Years Experience

About Lakeside Windermere Realty

We are Central Florida's premier real estate experts, dedicated to helping you find your dream home in the region's most sought-after communities. With decades of experience and a commitment to personalized service, we turn your real estate goals into reality.

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500+
Properties Sold
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1000+
Satisfied Clients
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25+
Years Experience
Lakeside Windermere Realty

Premier Communities

Premier Communities

Clermont
Clermont

Nestled among gentle hills and sparkling lakes, Clermont offers a stunning setting for refined lakeside living.

  • Scenic Hills
  • Waterfront Communities
  • Resort Comforts
Windermere
Windermere

An exclusive lakefront community known for luxury estates, pristine golf courses, and the famous Butler Chain of Lakes.

  • Luxury Estates
  • Golf Communities
  • Lake Access
Winter Garden
Winter Garden

Historic charm meets modern luxury in this vibrant community featuring downtown attractions and upscale neighborhoods.

  • Historic Downtown
  • New Developments
  • Family Friendly
Winter Park
Winter Park

Cultural sophistication, boutique shopping, and tree-lined streets with elegant historic homes and luxury condos.

  • Cultural District
  • Boutique Shopping
  • Historic Charm

Quick Searches

Quick Searches

Featured Properties

Featured Properties

Luxury condo at 1925 S Atlantic Ave Unit 502, Daytona Beach
$1,500,000
1925 S Atlantic Ave Unit 502
Daytona Beach, FL 32118
Bedrooms 4 Beds
Bathrooms 3 Baths
Square feet 2,927 sqft
Beautiful home at 17556 Deer Isle Cir, Winter Garden
$1,299,999
17556 Deer Isle Cir
Winter Garden, FL 34787
Bedrooms 4 Beds
Bathrooms 4 Baths
Square feet 3,214 sqft
Property at 15305 Shady Ln, Tavares
$768,900
15305 Shady Ln
Tavares, FL 32778
Bedrooms 4 Beds
Bathrooms 3 Baths
Square feet 2,601 sqft

Start Your Journey Today

From starter homes to luxury estates, we’re

here to help you find the place that feels right.

Get In Touch

Book a Private Consultation - Lakeside Windermere Realty
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With Our Team?

Let us help you find your dream home or sell your property with our expert guidance and personalized service.

© 2025 My Florida Regional MLS DBA Stellar MLS, Inc.. All rights reserved. The data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of My Florida Regional MLS DBA Stellar MLS, Inc. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.9/21/2025 11:14 AM CST

© 2025 My Florida Regional MLS DBA Stellar MLS, Inc.. All rights reserved. The data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of My Florida Regional MLS DBA Stellar MLS, Inc. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.9/21/2025 11:14 AM CST

 

Lakeside Realty Windermere

430 Main St. Windermere, FL 34786

 

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© 2025 Lakeside Windermere Realty. All Rights Reserved. Powered by Qorus

© 2025 Lakeside Windermere Realty. All Rights Reserved. Powered by Qorus