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Harbor Isle Windermere

Located in Windermere, just north of the Dr. Philips area of Orlando, and overlooking the beautiful Lake Down is Harbor Isle real estate. This gorgeous gated community is geographically situated at Orlando’s highest point, affording these 3,500 to 6,000+ square foot homes for sale some of the finest views of magnificent sunsets and scenery. Harbor Isle is a small and intimate community adorned with custom-built lakefront and estate homes erected from the late 1990’s to the early 2000’s. 

Harbor Isle Homes for Sale

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Harbor Isle Community Information

Location: Apopka Vineland Road - North of Conroy Windermere
Surrounding Lakes: Butler Chain of Lakes - Lake Down
Year Built: 1996 - 2003
Square Footage: 3,500 - 6,000+
HOA Fee's: $2,000 Annual *subject to change
Community Amenities: Gated Community

Residents of Harbor Isle in Windermere, FL enjoy privacy and seclusion while maintaining proximity to all of Central Florida’s fine dining, shopping, and family attractions. The areas top rated schools and small town feel make Harbor Isle an ideal place for professionals and families alike.

Orange County Public Schools

  • Thornebrooke Elementary School: Grades PreK - 5  Distance: 3.1 miles
  • Gotha Middle School: Grades 5 - 8  Distance: 2 miles
  • Olympia High School: Grades 9 - 12  Distance: .5 mile

Dining and Shopping

  • The Grove at Isleworth with Publix Grocery Store - Distance: .7 mile
  • Restaurant Row - Distance: 4.2 miles
  • The Mall at Millenia, Retail Shopping Centers, & BJ's Wholesale Club - Distance: 5.8 miles
  • Winter Garden Village Retail Shopping Center with Super Target - Distance: 7.5 miles
  • Downtown Orlando - Distance: 10 miles

Parks and Recreation

  • Dr. P. Phillips Community Park, Sporting Fields, Fountain Water Park, Dog Park - Distance: 7.3 miles
  • Bill Frederick Park at Turkey Lake, Community Pool, Boat Rentals, Camping, & Fishing Pier - Distance: 3.1 miles
  • Rose Place Orange County Park & Sporting Fields - Distance: 2.5 miles
  • Lake Down Public Access Boat Ramp - Distance: 1.6 miles
  • Dr. P. Phillips YMCA Family Center - Distance: 3.6 miles


  • Dr. P. Phillips Hospital - Distance: 7 miles
  • Health Central Hospital - Distance: 5.2 miles

*Distances are approximately measured from the Harbor Isle community entrance