Deer Island

Deer Island is a luxury gated community of single family homes in Winter Garden, Florida, with a range of options priced between $469,000 and $1,800,000. The smallest Deer Island home in the community is a four bedroom two bathroom residence that is 3,576 square feet (2,051SF Under Air living space), and the largest of the Deer Island homes has four beds and two baths and is a 7,796 square foot (4,945SF Under Air) residence.

Property management fees in Orange County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Deer Island are $1,240. This fee includes grounds maintenance, maintaining the community roads, the community pool, real estate taxes for common areas, Cable TV & internet, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Deer Island home.

Sports facilities include tennis courts, racquetball, and basketball court. There is also a community park, as well as walking or jogging trails.

The Deer Island HOA rules do allow homeowners to have pets. Dogs and cats are allowed.

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

Deer Island real estate activity on the Winter Garden MLS during the past year (as of June 2026) reflects ten homes changing hands, with an average asking price of $1,327,368 and an average selling price of $1,227,761. This represents a healthy list-to-sell price ratio of 92% and $275 per square foot. During this period, Deer Island homes for sale have taken an average of 149 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 Deer Island are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Deer Island hits the market. You can also always contact your BEX Realty agent, who would happily assist you further with all your Central Florida real estate needs.

Deer Island Homes For Sale

SOLD 11/27/23

$1,795,000

$2,175,000

MLS#MFRO6124895

17667 Deer Isle Cir
Winter Garden, FL 34787

5

4

4

5,077 SqFt

Pool

Water Front

1.17 Acres

SOLD 01/09/12

$550,000

$685,000

MLS#MFRO5001531

17675 Deer Isle Cir
Winter Garden, FL 34787

4

5

3

3,842 SqFt

Pool

Water Front

1.02 Acres

SOLD 06/10/05

$725,000

MLS#MFRO4617066

17623 Deer Isle Cir
Winter Garden, FL 34787

3

3

2

2,237 SqFt

Pool

Water Front

1.3 Acres

SOLD 12/29/23

$1,399,999

$1,575,000

MLS#MFRO6143692

17691 Deer Isle Cir
Winter Garden, FL 34787

5

3

3

5,608 SqFt

Water Front

0.99 Acres

SOLD 06/10/26

$1,025,000

$1,100,000

MLS#MFRO6350825

17608 Deer Isle Cir
Winter Garden, FL 34787

4

3

3

4,060 SqFt

Pool

1.08 Acres

SOLD 11/20/13

$469,000

MLS#MFRO5184617

17589 Deer Isle Cir
Winter Garden, FL 34787

3

4

3

3,576 SqFt

Water Front

1.01 Acres

SOLD 01/05/26

$2,199,900

MLS#MFRO6336529

17585 Deer Isle Cir
Winter Garden, FL 34787

5

4

2

5,472 SqFt

Pool

1 Acre

SOLD 08/21/19

$838,500

MLS#MFRNS1050565

17729 Deer Isle Cir
Winter Garden, FL 34787

4

3

4,281 SqFt

Pool

Water Front

2.25 Acres

SOLD 01/26/18

$775,000

MLS#MFRO5550463

17704 Deer Isle Cir
Winter Garden, FL 34787

4

3

3

4,806 SqFt

Pool

1.05 Acres

SOLD 02/27/26

$1,225,000

$1,400,000

MLS#MFRO6332919

17556 Deer Isle Cir
Winter Garden, FL 34787

4

4

2

4,610 SqFt

Pool

1.03 Acres

SOLD 10/06/16

$849,900

$874,900

MLS#MFRO5446672

17548 Deer Isle Cir
Winter Garden, FL 34787

4

4

3

6,198 SqFt

Pool

1.04 Acres

SOLD 09/29/23

$895,500

$969,900

MLS#MFRO6126280

17712 Deer Isle Cir
Winter Garden, FL 34787

4

3

3

4,134 SqFt

1.03 Acres

SOLD 03/09/22

$1,050,000

MLS#MFRO5996560

17814 Westbay Ct
Winter Garden, FL 34787

3

2

2

3,764 SqFt

Pool

Water Front

0.9 Acres

SOLD 05/28/23

$1,295,000

MLS#MFRO6097934

17818 Westbay Ct
Winter Garden, FL 34787

4

3

3

3,753 SqFt

Pool

Water Front

1 Acre

SOLD 03/17/23

$1,800,000

$1,975,000

MLS#MFRO6067795

17716 Deer Isle Cir
Winter Garden, FL 34787

4

4

4

7,387 SqFt

Pool

1.03 Acres

SOLD 08/22/25

$858,126

MLS#MFRO6299635

11009 Hollow Bay Dr
Winter Garden, FL 34787

5

5

2

3,690 SqFt

0.24 Acres

New Construction

SOLD 08/14/25

$903,071

MLS#MFRO6299660

11015 Hollow Bay Dr
Winter Garden, FL 34787

4

4

2

3,790 SqFt

0.22 Acres

New Construction

SOLD 10/30/25

$549,990

$568,950

MLS#MFRO6308482

11176 Hollow Bay Dr
Winter Garden, FL 34787

3

3

2

2,490 SqFt

0.12 Acres

New Construction

SOLD 09/26/25

$646,075

MLS#MFRO6334522

11194 Hollow Bay Dr
Winter Garden, FL 34787

4

4

2

2,890 SqFt

0.12 Acres

New Construction

SOLD 10/22/25

$916,521

MLS#MFRO6336045

11093 Hollow Bay Dr
Winter Garden, FL 34787

4

4

2

3,790 SqFt

0.36 Acres

New Construction

SOLD 11/22/24

$1,350,000

$1,700,000

MLS#MFRO6181053

17732 Deer Isle Cir
Winter Garden, FL 34787

5

4

3

6,156 SqFt

Pool

1.01 Acres

SOLD 10/18/13

$485,000

$499,000

MLS#MFRG4696462

17512 Deer Isle Cir
Winter Garden, FL 34787

4

4

3

4,382 SqFt

Pool

1.02 Acres

SOLD 12/29/21

$1,150,000

MLS#MFRO5975996

17811 Westbay Ct
Winter Garden, FL 34787

5

3

3

5,306 SqFt

Pool

Water Front

1.34 Acres

SOLD 04/27/26

$2.95 Million

MLS#MFRO6381953

17737 Deer Isle Cir
Winter Garden, FL 34787

5

5

3

7,790 SqFt

Pool

Water Front

1.02 Acres

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We do not have any properties available for sale in Deer Island.

0 Active Listings in Deer Island