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John's Landing Winter Garden Real Estate

John's Landing is a picturesque neighborhood located on Johns Lake in the city of Oakland, Florida. Featuring neighboring Winter Garden real estate at its best, this beautiful, gated community of single-family homes was constructed between 2000-2006. Perfectly situated on quarter to half-acre lots, the homes range in size from approximately 2,100 to 5,400 square feet and feature 3 - 6 bedrooms and 2 -3 car garages.

John's Landing Homes for Sale

4 Properties Found. Page 1 of 1.
Photo of Listing #O6127867
MLS® # O6127867
5 Beds, 4 Baths, 3,285 Sf
Photo of Listing #O6123908
Reduced 2.7%

645 Strihal Loop

MLS® # O6123908
4 Beds, 3 Baths, 2,606 Sf
Photo of Listing #O6118911
Reduced 3.9%
MLS® # O6118911
4 Beds, 4 Baths, 3,008 Sf
Photo of Listing #R4906404
Reduced 11.3%
MLS® # R4906404
5 Beds, 4 Baths, 4,475 Sf


John's Landing features 272 homesites and includes an abundance of natural foliage and large ponds interspersed throughout the property. The Central Florida community offers a variety of architectural style homes. Neighborhood amenities include a community boat ramp, colorful playground, Tennis Courts, and water access to John’s Landing. Sidewalks offer a perfect place to take a stroll or bike ride around the community.

Convenient access to the Florida Turnpike, Hwy 50, and the 408 and 429 Expressways make Florida's major attractions easily accessible. Just 19 miles from Downtown Orlando and short drives to Walt Disney World and Universal Orlando Resort brings residents close to all of the Orlando fun.

The community is surrounded by a variety of options making daily living easy. Families take advantage close proximity to top-rated Orange County schools and medical facilities. The nearest shopping center with grocery store is only 4 miles away at West Point Commons.

Residents enjoy a multitude of fun and recreational opportunities at John's Landing. From visiting the local theme parks, boating in John's Lake, or playing golf at the surrounding area courses, the entire family can stay active. Downtown Winter Garden and Winter Garden Village feature top-quality restaurants and shopping for great nights out.

Find a great location and beautiful homes at John's Landing.

John's Landing Community Information

  • Location: Remington Road & John’s Landing Way
  • Surrounding Lakes: Johns Lake
  • Number of Homesites: 272 
  • Built: 2000 - 2005
  • Square Footage: 2,100 to 5,400
  • HOA: Yes 
  • Amenities: Lakefront community, private boat ramp, dock, water access, playground, and tennis courts

Orange County Area Schools

  • Tildenville Elementary Grades Pre-K - 5th - Distance: 3 miles
  • Lakeview Middle School Grades 6-8 - Distance: 4 miles
  • West Orange High School: Grades 9th - 12th - Distance: 6 miles

Dining and Shopping

  • West Point Commons with Publix Grocery-Distance 4 miles
  • Winter Garden Village Retail Shopping Center with Super Target - Distance: 6 miles
  • Stoneybrook West Village Shopping Center with Publix Grocery - Distance: 8 miles
  • Downtown Winter Garden: 4 miles
  • Restaurant Row - Distance: 19 miles
  • The Mall at Millenia, Retail Shopping Centers, & BJ's Wholesale Club - Distance: 17 miles
  • Downtown Orlando - Distance: 18 miles

Parks and Recreation

  • Johns Lake Conservation Area - Distance: 6 miles
  • Horizon West Park & Sportsplex - Distance: 8 miles
  • West Orange Trail - Distance: 11 miles
  • Roper YMCA Family Center - Distance: 6 miles
  • Walt Disney World - Distance: 18.5 miles


  • Health Central Hospital - Distance: 8 miles
  • AdventHealth Winter Garden - Distance: 6.5 miles

*Distances are approximately measured from John's Landing community entrance

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 consumer 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.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on September 25th, 2023 at 2:34am EDT.