Waterside Winter Garden

Waterside is a gated community offering luxury lakefront real estate in Winter Garden, FL. Situated along the shores of Johns Lake, Waterside real estate provides homeowners with two distinct neighborhoods: The Landings and The Strand. Floor plans  range from 4 - 5 bedrooms, 3 - 7 bathrooms, and generous square footages spanning from 2,697 - 6,145 in size. The Waterside on Johns Lake neighborhood is sure to please residents with its gorgeous natural landscapes, community pool, pavilion, and convenient proximity to Downtown Orlando, HWY 429, and the many highly sought after local hot spots throughout the Southwest Orlando region.

Waterside 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

Waterside Real Estate Market Statistics

Average Price $652K
Lowest Price $64.9K
Highest Price $2.8M
Total Listings 51
Avg. Days On Market 172
Avg. Price/SQFT $253
List to Sell Price Percentage 97 %

Property Types (active listings)

Winter Garden Communities

Waterside on Johns Lake Community Information

Location: Marsh Road & Harbor Oak Way, Just West of Avalon Road
Surrounding Lakes: Johns Lake
Number of Homesites: 34 Lakefront Homesites, 105 Interior Homesites
Year(s) Built: 2015 - 2022
HOA: Yes
Square Footage: 1,692 - 8,200+
Community Amenities: Lakefront Community, Gated Community, Community Pool & Pavilion, Playground, Trails, Dock, Fitness Center
Standard Pacific Models & Floorplans: Carlisle, Brighton, Richmond, Southport, Preston, Champlain, Mansfield, Geneva, Killarney, Lucerne, and Victoria

Orange County Public Schools

  • Hamlin Elementary: Grades Pre-K - 5th Distance: 6 miles
  • Hamlin Middle School: Grades 6th - 8th Distance: 5.5 miles
  • West Orange High School: Grades 9th - 12th Distance: 6 miles

Dining and Shopping

  • Stoneybrook West Village Shopping Center with Publix Grocery - Distance: 1 mile
  • Downtown Winter Garden: 6 miles
  • Restaurant Row - Distance: 19 miles
  • The Mall at Millenia, Retail Shopping Centers, & BJ's Wholesale Club - Distance: 17 miles
  • Winter Garden Village Retail Shopping Center with Super Target - Distance: 3 miles
  • Downtown Orlando - Distance: 19 miles

Parks and Recreation

  • West Orange Trail - Distance: 5 miles
  • Roper YMCA Family Center - Distance: 6 miles

Hospitals

  • AdventHealth Winter Garden Hospital: Distance: 3 miles
  • Health Central Hospital - Distance: 8 miles

*Distances are approximately measured from the Waterside community entrance. 

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