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 Open House
16924 Tradewind Point, WINTER GARDEN

$724,999

16924 Tradewind Point, WINTER GARDEN

4 Beds 4 Baths 2,958 SqFt Residential
Sat, Sep 12th, 2026 @ 11am - 3pm
MLS® # O6439183
New Pending
1527 Viscaya Cove Boulevard, WINTER GARDEN

$635,000

1527 Viscaya Cove Boulevard, WINTER GARDEN

4 Beds 4 Baths 2,478 SqFt Residential MLS® # O6440090
New
16795 Turtle Hatch Drive, WINTER GARDEN

$1,249,990

16795 Turtle Hatch Drive, WINTER GARDEN

5 Beds 5 Baths 3,615 SqFt Residential MLS® # O6438512
New Pending
16753 Turtle Hatch Drive, WINTER GARDEN

$1,159,000

16753 Turtle Hatch Drive, WINTER GARDEN

4 Beds 4 Baths 2,954 SqFt Residential MLS® # O6438081
New
1374 Viscaya Cove Boulevard, WINTER GARDEN

$545,000

1374 Viscaya Cove Boulevard, WINTER GARDEN

4 Beds 4 Baths 2,492 SqFt Residential MLS® # O6438465
New Pending
1372 Roxy Lane, WINTER GARDEN

$519,900

1372 Roxy Lane, WINTER GARDEN

4 Beds 3 Baths 2,030 SqFt Residential MLS® # O6437028
New
16730 Rusty Anchor Road, WINTER GARDEN

$1,350,000

16730 Rusty Anchor Road, WINTER GARDEN

6 Beds 5 Baths 4,451 SqFt Residential MLS® # S5156404
Open House
17307 Bal Harbour Drive, WINTER GARDEN

$660,000

17307 Bal Harbour Drive, WINTER GARDEN

3 Beds 2 Baths 2,123 SqFt Residential
Sun, Sep 13th, 2026 @ 12pm - 3pm
MLS® # O6436527
Pending
16954 Tradewind Point, WINTER GARDEN

$482,000

16954 Tradewind Point, WINTER GARDEN

3 Beds 2 Baths 1,692 SqFt Residential MLS® # O6431248
Pending
16971 Tradewind Point, WINTER GARDEN

$703,000

16971 Tradewind Point, WINTER GARDEN

4 Beds 4 Baths 2,782 SqFt Residential MLS® # O6426531
Pending
16936 Tradewind Point, WINTER GARDEN

$639,000

↓ $6,000

16936 Tradewind Point, WINTER GARDEN

4 Beds 4 Baths 2,930 SqFt Residential MLS® # O6424578
Pending
17059 Harbor Oak Parkway, WINTER GARDEN

$620,000

↓ $10,000

17059 Harbor Oak Parkway, WINTER GARDEN

4 Beds 3 Baths 2,692 SqFt Residential MLS® # G5114379
16614 Harbor Sail Way, WINTER GARDEN

$1,399,000

↓ $51,000

16614 Harbor Sail Way, WINTER GARDEN

6 Beds 6 Baths 4,882 SqFt Residential MLS® # O6414639
Pending
17035 Harbor Oak Parkway, WINTER GARDEN

$485,000

↓ $14,999

17035 Harbor Oak Parkway, WINTER GARDEN

3 Beds 2 Baths 1,692 SqFt Residential MLS® # O6411409

Waterside Real Estate Market Statistics

Average Price $586K
Lowest Price $50K
Highest Price $6M
Total Listings 135
Avg. Days On Market 188
Avg. Price/SQFT $239
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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