Watermark Winter Garden

Watermark is a community of single family homes, and townhomes in Winter Garden, Florida, with a range of options priced between $399,900 and $1,495,000. There are currently a total of 30 homes for sale in Watermark. The smallest Watermark home presently available is a three bedroom two bathroom residence that is 2,060 square feet (1,696SF Under Air living space), and the largest of the Watermark homes currently on the market has six beds and five baths and is a 6,688 square foot (4,493SF 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 Watermark range from $145 to $160 and $159 to $404 for a townhome. This fee includes common area maintenance, grounds maintenance, building maintenance, the community pool, security, and real estate taxes for common areas. Also included is property insurance, water, trash removal, sewer, Cable TV, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Watermark home.

Watermark amenities include a clubhouse, swimming pool, spa / hot tub, a state-of-the-art fitness center, and laundry facilities. Sports facilities include tennis courts, racquetball, and basketball court. There is also a community park, a playground, a dog park, as well as walking or jogging trails.

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

There are three subdivisions within the Watermark community, they are: Esplanade, Lakeside, and Watermark Terrace.

There are four commercial airports that serve Watermark - Kissimmee Gateway (ISM), which is fifteen miles away; Orlando Executive (ORL), which is nineteen miles away; Orlando International (MCO), which is nineteen miles away, and Orlando Sanford International (SFB), which is 34 miles away from Watermark.

Watermark real estate activity on the Winter Garden MLS during the past year (as of September 2025) reflects 40 homes changing hands, with an average asking price of $617,510 and an average selling price of $597,658. This represents a healthy list-to-sell price ratio of 97% and $180 per square foot. During this period, Watermark homes for sale have taken an average of 69 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 Watermark are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Watermark 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.

Watermark Homes For Sale

$1,495,000

Watermark Terrace

10139 Austrina Oak Loop
Winter Garden, FL 34787

6

5

2

5,591 SqFt

Pool

0.31 Acres

151 Days

Under Contract

$1,295,000

$1,690,000

MLS#MFRO6304725

9574 Meadow Hunt Way
Winter Garden, FL 34787

5

6

3

6,688 SqFt

Pool

0.26 Acres

146 Days

Reduced

$1,225,000

$1,250,000

Watermark Terrace

9845 Emerald Berry Dr
Winter Garden, FL 34787

5

5

2

6,013 SqFt

Pool

0.14 Acres

136 Days

Under Contract

$1,190,000

$1,199,000

MLS#MFRO6324372

14507 Winter Stay Dr
Winter Garden, FL 34787

5

4

2

5,059 SqFt

Pool

0.19 Acres

86 Days

$1,150,000

MLS#MFRS5133686

14612 Glade Hill Park Way
Winter Garden, FL 34787

5

5

2

4,729 SqFt

0.17 Acres

30 Days

$1,100,000

Watermark Terrace

10037 Austrina Oak Loop
Winter Garden, FL 34787

5

4

3

4,305 SqFt

0.31 Acres

42 Days

Reduced

$899,999

$1,099,000

MLS#MFRO6277173

9573 Meadow Hunt Way
Winter Garden, FL 34787

5

4

3

5,308 SqFt

Pool

0.17 Acres

234 Days

$890,000

MLS#MFRO6343171

9182 Holliston Creek Pl
Winter Garden, FL 34787

4

4

2

4,080 SqFt

Pool

0.14 Acres

1 Days

Reduced

$887,000

$959,000

MLS#MFRO6291068

14645 Scott Key Dr
Winter Garden, FL 34787

4

4

2

4,564 SqFt

Pool

0.14 Acres

194 Days

Reduced

$849,000

$890,000

Watermark Terrace

9870 Summerlake Groves St
Winter Garden, FL 34787

4

4

2

4,503 SqFt

Pool

0.14 Acres

177 Days

Reduced

$780,000

$820,000

MLS#MFRO6287859

14602 Winter Stay Dr
Winter Garden, FL 34787

4

4

2

4,512 SqFt

0.14 Acres

205 Days

Under Contract

$775,000

MLS#MFRO6333211

14757 Glade Hill Park Way
Winter Garden, FL 34787

4

4

2

4,080 SqFt

Pool

0.17 Acres

54 Days

You may also be interested in Watermark in Fort Myers, Watermark in Bradenton or Watermark in Cocoa.

30 Active Listings in Watermark