Watermark Winter Garden

Watermark is a community of single family homes, and townhomes in Winter Garden, Florida, with a range of options priced between $380,900 and $1,190,000. There are currently a total of 20 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 5,724 square foot (4,305SF 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 $142 to $165 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 February 2026) reflects 44 homes changing hands, with an average asking price of $663,161 and an average selling price of $640,792. This represents a healthy list-to-sell price ratio of 97% and $181 per square foot. During this period, Watermark homes for sale have taken an average of 82 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

$1,190,000

Watermark Terrace

10067 Austrina Oak Loop
Winter Garden, FL 34787

6

5

3

5,724 SqFt

0.31 Acres

84 Days

Under Contract

$1,050,000

Watermark Terrace

10037 Austrina Oak Loop
Winter Garden, FL 34787

5

4

3

5,724 SqFt

0.31 Acres

133 Days

$1 Million

MLS#MFRO6366636

9207 Busaco Park Way
Winter Garden, FL 34787

5

4

2

4,859 SqFt

Water Front

0.17 Acres

62 Days

$977,000

MLS#MFRG5106818

14645 Scott Key Dr
Winter Garden, FL 34787

4

4

2

4,564 SqFt

Pool

0.14 Acres

27 Days

$925,000

Watermark Terrace

9929 Summerlake Groves St
Winter Garden, FL 34787

5

5

2

4,114 SqFt

0.17 Acres

93 Days

Under Contract

$798,000

$820,000

Watermark Terrace

14963 Guava Bay Dr
Winter Garden, FL 34787

4

4

2

3,810 SqFt

0.14 Acres

76 Days

Under Contract

$785,000

$789,000

MLS#MFRTB8455422

9282 Woodcrane Dr
Winter Garden, FL 34787

4

4

2

3,810 SqFt

Pool

0.14 Acres

52 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

342 Days

Reduced

$749,000

$759,000

MLS#MFRS5138514

14710 Scott Key Dr
Winter Garden, FL 34787

5

4

2

4,216 SqFt

0.14 Acres

91 Days

Under Contract

$699,999

$715,000

MLS#MFRO6370598

14673 Glade Hill Park Way
Winter Garden, FL 34787

5

3

2

3,906 SqFt

0.14 Acres

38 Days

$545,000

Watermark Terrace

9803 Amber Chestnut Way
Winter Garden, FL 34787

4

4

2

3,252 SqFt

0.07 Acres

5 Days

Reduced

$525,000

$550,000

Watermark Terrace

14954 Guava Bay Dr
Winter Garden, FL 34787

4

3

2

2,866 SqFt

0.09 Acres

218 Days

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

20 Active Listings in Watermark