John's Landing

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

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New
301 New Providence Promenade 301, DAVENPORT

$159,900

301 New Providence Promenade 301, DAVENPORT

2 Beds 2 Baths 1,372 SqFt Residential MLS® # O6448381
New
2222 Majestic Eagle Circle, CLERMONT

$340,000

2222 Majestic Eagle Circle, CLERMONT

3 Beds 2 Baths 1,564 SqFt Residential MLS® # C7531749
New
5446 Knotty Oak Street, MOUNT DORA

$483,990

5446 Knotty Oak Street, MOUNT DORA

3 Beds 2 Baths 2,123 SqFt Residential MLS® # TB8556245
New
5836 Daughtery Downs Loop, LAKELAND

$315,000

5836 Daughtery Downs Loop, LAKELAND

3 Beds 2 Baths 1,686 SqFt Residential MLS® # A4708911
New
1795 Grandiose Drive, LAKE HAMILTON

$298,490

1795 Grandiose Drive, LAKE HAMILTON

4 Beds 2 Baths 1,574 SqFt Residential MLS® # O6448438
New Open House
715 Drawdy Road, BABSON PARK

$247,000

715 Drawdy Road, BABSON PARK

3 Beds 2 Baths 1,858 SqFt Residential MLS® # O6447953
New
1787 Grandiose Drive, LAKE HAMILTON

$296,990

1787 Grandiose Drive, LAKE HAMILTON

4 Beds 2 Baths 1,574 SqFt Residential MLS® # O6448442
New
2463 Aveeno Avenue, HAINES CITY

$432,490

2463 Aveeno Avenue, HAINES CITY

5 Beds 4 Baths 2,878 SqFt Residential MLS® # O6448378
New
26717 Wetlands Way, LEESBURG

$365,000

26717 Wetlands Way, LEESBURG

3 Beds 3 Baths 2,620 SqFt Residential MLS® # G5118826
New
798 Millhorn Loop, THE VILLAGES

$359,000

798 Millhorn Loop, THE VILLAGES

3 Beds 2 Baths 1,500 SqFt Residential MLS® # G5118816
New
7624 Rex Hill Trail, ORLANDO

$350,000

7624 Rex Hill Trail, ORLANDO

3 Beds 2 Baths 1,299 SqFt Residential MLS® # O6448419
New
Timberlane Road, LAKE WALES

$215,000

Timberlane Road, LAKE WALES

0 Beds 0 Baths 0 SqFt Land MLS® # O6448344
New
Timberlane Road, LAKE WALES

$269,000

Timberlane Road, LAKE WALES

0 Beds 0 Baths 0 SqFt Land MLS® # O6448343
New Open House
20 Walden, ORMOND BEACH

$349,900

20 Walden, ORMOND BEACH

3 Beds 2 Baths 1,874 SqFt Residential
Sat, Oct 10th, 2026 @ 12pm - 3pm
MLS® # V4951731
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447200
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447201
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447198
Pending
1624 Sterns Drive, LEESBURG

$285,000

1624 Sterns Drive, LEESBURG

4 Beds 2 Baths 2,936 SqFt Residential MLS® # O6425853
New
3110 Emerald Acres Lane, SANFORD

$374,500

3110 Emerald Acres Lane, SANFORD

3 Beds 3 Baths 1,682 SqFt Residential MLS® # S5159186
New
5714 Cattle Ranch Drive, ST CLOUD

$3,095

5714 Cattle Ranch Drive, ST CLOUD

4 Beds 4 Baths 3,058 SqFt Residential MLS® # O6448300
1211 Nixonton Street, DELTONA

$440,000

1211 Nixonton Street, DELTONA

3 Beds 3 Baths 2,208 SqFt Residential MLS® # V4951068
New
140 Bombay Avenue, WINTER SPRINGS

$355,000

140 Bombay Avenue, WINTER SPRINGS

3 Beds 2 Baths 1,373 SqFt Residential MLS® # O6448262
New
31744 Boadwater Ave, LEESBURG

$369,900

31744 Boadwater Ave, LEESBURG

4 Beds 3 Baths 2,626 SqFt Residential MLS® # O6447594
New
5381 Maddie Drive, HAINES CITY

$399,900

5381 Maddie Drive, HAINES CITY

5 Beds 3 Baths 3,011 SqFt Residential MLS® # O6446669
New Open House
1249 Waterwitch Cove Circle, ORLANDO

$874,900

1249 Waterwitch Cove Circle, ORLANDO

3 Beds 3 Baths 2,715 SqFt Residential
Sat, Oct 10th, 2026 @ 1pm - 4pm
MLS® # O6446291
New
1881 Red Canyon Drive, KISSIMMEE

$310,000

1881 Red Canyon Drive, KISSIMMEE

3 Beds 3 Baths 1,624 SqFt Residential MLS® # O6448530
New
251 Patterson Road D4, HAINES CITY

$105,000

251 Patterson Road D4, HAINES CITY

1 Bed 2 Baths 836 SqFt Residential MLS® # P4940061
344 Sky Valley Street, CLERMONT

$345,000

344 Sky Valley Street, CLERMONT

3 Beds 2 Baths 1,581 SqFt Residential MLS® # O6423173
New
814 Texas Avenue, LAKELAND

$145,000

814 Texas Avenue, LAKELAND

4 Beds 2 Baths 1,312 SqFt Residential MLS® # O6448654
New
14 Apple Hill Hollow, CASSELBERRY

$375,000

14 Apple Hill Hollow, CASSELBERRY

3 Beds 2 Baths 1,288 SqFt Residential MLS® # O6448584

Sold Homes in Isles of John's Landing Winter Garden

John's Landing Real Estate Market Statistics

Average Price $695K
Lowest Price $540K
Highest Price $996K
Total Listings 4
Avg. Days On Market 124
Avg. Price/SQFT $211
List to Sell Price Percentage 98 %

Property Types (active listings)

Winter Garden Communities


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

Hospitals

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

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

Orlando - Windermere Home

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