Waterside Winter Garden

Waterside is a community of single family homes in Winter Garden, Florida, with a range of options priced between $539,990 and $1,850,000. There are currently a total of 7 homes for sale in Waterside. The smallest Waterside home presently available is a three bedroom two bathroom residence that is 2,492 square feet (1,692SF Under Air living space), and the largest of the Waterside homes currently on the market has five beds and five baths and is a 5,379 square foot (3,800SF Under Air) residence.

Property management fees in Orange County vary depending on the community and the subdivision within the community and sometimes vary between homes in the subdivision. The current HOA fees for homes in Waterside range from $210 to $373. This fee includes common area maintenance, grounds maintenance, building maintenance, maintaining the community roads, the community pool, and security. Also included is real estate taxes for common areas, property insurance, trash removal, Cable TV, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Waterside home.

Waterside amenities include a clubhouse, swimming pool, and a state-of-the-art fitness center. There is also a community park, a playground, a dog park, as well as walking or jogging trails.

The Waterside Master HOA does allow pets, however the various subdivision may impose their own pet restrictions, so check the individual listings for specifics.

There is also a subdivision within Waterside that is called The Cove.

There are four commercial airports that serve Waterside - Orlando Executive (ORL), which is nineteen miles away; Kissimmee Gateway (ISM), which is twenty miles away; Orlando International (MCO), which is twenty one miles away, and Orlando Sanford International (SFB), which is 30 miles away from Waterside.

Waterside real estate activity on the Winter Garden MLS during the past year (as of January 2026) reflects twenty seven homes changing hands, with an average asking price of $1,292,256 and an average selling price of $1,045,149. This represents a list-to-sell price ratio of 81% and $240 per square foot. During this period, Waterside homes for sale have taken an average of 80 days to sell.

In addition, there are numerous other communities in Winter Garden to choose from, or you may browse all available Winter Garden Real Estate, including some new construction opportunities. Homes for sale in Waterside are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Waterside hits the market. You can also always contact your ZFC Real Estate agent, who would happily assist you further with all your Central Florida real estate needs.

Waterside Homes For Sale

Under Contract

$1,850,000

MLS#MFRO6367848

16743 Broadwater Ave
Winter Garden, FL 34787

5

6

3

5,379 SqFt

Pool

Water Front

0.46 Acres

34 Days

Under Contract

$685,000

$689,000

MLS#MFRO6367040

17344 Bal Harbour Dr
Winter Garden, FL 34787

4

3

2

2,817 SqFt

0.16 Acres

36 Days

Reduced

$575,000

$585,000

The Cove

1413 Viscaya Cove Blvd
Winter Garden, FL 34787

4

4

2

3,065 SqFt

0.11 Acres

109 Days

$570,000

The Cove

17058 Quicksilver Ave
Winter Garden, FL 34787

4

4

2

2,492 SqFt

0.11 Acres

42 Days

Under Contract

$569,000

$579,000

The Cove

1527 Viscaya Cove Blvd
Winter Garden, FL 34787

4

4

2

3,058 SqFt

0.16 Acres

49 Days

$540,000

MLS#MFRO6367439

16912 Tradewind Pt
Winter Garden, FL 34787

3

2

2

4,597 SqFt

0.11 Acres

33 Days

Under Contract

$539,990

The Cove

1373 Williams Rd
Winter Garden, FL 34787

4

4

2

3,065 SqFt

0.11 Acres

18 Days

You may also be interested in Waterside in Boca Raton, Waterside in Vero Beach, Waterside in West Palm Beach, Waterside in Boynton Beach, Waterside in Homestead, Waterside in Orlando, Waterside in St Petersburg, Waterside in Indian Shores or Waterside in Tampa.

7 Active Listings in Waterside