Waterside Winter Garden

Waterside is a community of single family homes in Winter Garden, Florida, with a range of options priced between $475,000 and $9,900,000. There are currently a total of 9 homes for sale in Waterside. The smallest Waterside home presently available is a three bedroom two bathroom residence that is 2,451 square feet (1,692SF Under Air living space), and the largest of the Waterside homes currently on the market has seven beds and five baths and is a 9,874 square foot (6,977SF 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 $158 to $368. 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 September 2025) reflects twenty three homes changing hands, with an average asking price of $937,531 and an average selling price of $906,788. This represents a healthy list-to-sell price ratio of 97% and $210 per square foot. During this period, Waterside homes for sale have taken an average of 65 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

$9.9 Million

$12,000,000

MLS#MFRO6254855

17017 Marsh Rd
Winter Garden, FL 34787

6

6

9,874 SqFt

Pool

Water Front

17.88 Acres

304 Days

Under Contract

$2.995 Million

MLS#MFRO6328819

16821 Broadwater Ave
Winter Garden, FL 34787

7

6

3

8,369 SqFt

Pool

Water Front

0.49 Acres

38 Days

Reduced

$1,749,000

$1,925,000

MLS#MFRO6310760

16761 Broadwater Ave
Winter Garden, FL 34787

5

6

3

4,879 SqFt

Pool

Water Front

0.47 Acres

106 Days

Reduced

$949,900

$969,900

MLS#MFRO6330658

16712 Rusty Anchor Rd
Winter Garden, FL 34787

4

4

3

4,224 SqFt

0.21 Acres

40 Days

Under Contract

$879,000

$999,000

MLS#MFRO6308256

16696 Otterchase Ln
Winter Garden, FL 34787

4

4

3

4,144 SqFt

0.2 Acres

112 Days

$650,000

MLS#MFRO6330396

1565 Bayfront Park Aly
Winter Garden, FL 34787

4

4

2

3,796 SqFt

0.16 Acres

39 Days

Reduced

$559,900

$574,900

The Cove

1373 Williams Rd
Winter Garden, FL 34787

4

4

2

3,065 SqFt

0.11 Acres

114 Days

Reduced

$489,999

$514,999

MLS#MFRO6323499

1559 Bayfront Park Aly
Winter Garden, FL 34787

3

2

2

2,451 SqFt

0.16 Acres

65 Days

Reduced

$475,000

$485,000

MLS#MFRO6334355

17047 Harbor Oak Pkwy
Winter Garden, FL 34787

3

2

2

2,511 SqFt

0.11 Acres

28 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 or Waterside in Indian Shores.

9 Active Listings in Waterside