Bear Gully Pointe

Bear Gully Pointe is a gated community of single family homes in Winter Park, Florida, with a range of options priced between $584,900 and $2,250,000. The smallest Bear Gully Pointe home in the community is a four bedroom three bathroom residence that is 4,634 square feet (3,321SF Under Air living space), and the largest of the Bear Gully Pointe homes has four beds and six baths and is a 9,376 square foot (6,252SF 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 Bear Gully Pointe range from $400 to $500. This fee includes grounds maintenance, and real estate taxes for common areas. Please check the individual listing pages for the exact homeowners association fees for a particular Bear Gully Pointe home.

Sports facilities include tennis courts.

The Bear Gully Pointe HOA rules do allow homeowners to have pets.

There are four commercial airports that serve Bear Gully Pointe - Orlando Executive (ORL), which is six miles away; Orlando Sanford International (SFB), which is eleven miles away; Orlando International (MCO), which is thirteen miles away, and Kissimmee Gateway (ISM), which is twenty five miles away from Bear Gully Pointe.

Bear Gully Pointe real estate activity on the Winter Park MLS during the past year (as of October 2025) reflects five homes changing hands, with an average asking price of $1,116,700 and an average selling price of $1,073,880. This represents a healthy list-to-sell price ratio of 96% and $210 per square foot. During this period, Bear Gully Pointe homes for sale have taken an average of 54 days to sell.

In addition, there are numerous other communities in Winter Park to choose from, or you may browse all available Winter Park Real Estate, including some new construction opportunities. Homes for sale in Bear Gully Pointe are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Bear Gully Pointe 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.

Bear Gully Pointe Homes For Sale

SOLD 11/16/21

$765,000

MLS#MFRO5970264

4027 Gilder Rose Pl
Winter Park, FL 32792

4

5

3

3,369 SqFt

Pool

0.51 Acres

SOLD 12/09/24

$1,095,000

MLS#MFRO6254459

4032 Gilder Rose Pl
Winter Park, FL 32792

4

4

3

5,542 SqFt

Pool

0.42 Acres

SOLD 09/15/23

$1,195,000

MLS#MFRO6131465

2894 Wild Ginger Ct
Winter Park, FL 32792

4

4

3

5,653 SqFt

Pool

0.41 Acres

SOLD 04/29/16

$584,900

$589,900

MLS#MFRO5395207

2889 Old Castle Dr
Winter Park, FL 32792

4

4

3

4,861 SqFt

Pool

0.47 Acres

SOLD 10/09/25

$999,500

$1,225,000

MLS#MFRO6321617

2890 Wild Ginger Ct
Winter Park, FL 32792

4

5

3

4,634 SqFt

Pool

0.38 Acres

SOLD 10/17/24

$1,178,000

MLS#MFRO6233722

2884 Old Castle Dr
Winter Park, FL 32792

4

4

3

5,951 SqFt

Pool

0.43 Acres

SOLD 09/30/25

$1,100,000

$1,125,000

MLS#MFRO6313631

2880 Old Castle Dr
Winter Park, FL 32792

5

5

3

5,133 SqFt

Pool

0.41 Acres

SOLD 07/31/25

$1,199,000

$1,250,000

MLS#MFRO6312182

4052 Gilder Rose Pl
Winter Park, FL 32792

4

5

3

5,405 SqFt

Pool

0.55 Acres

SOLD 10/15/25

$1,190,000

$1,210,000

MLS#MFRO6316911

4048 Gilder Rose Pl
Winter Park, FL 32792

4

4

3

4,879 SqFt

Pool

0.72 Acres

SOLD 10/08/21

$924,900

MLS#MFRO5964971

2872 Old Castle Dr
Winter Park, FL 32792

4

5

3

4,227 SqFt

Pool

0.5 Acres

SOLD 08/09/24

$1.5 Million

$1,599,000

MLS#MFRO6180611

4091 Scarlet Iris Pl
Winter Park, FL 32792

6

6

3

9,376 SqFt

Pool

0.68 Acres

SOLD 03/01/22

$2,250,000

$2,500,000

MLS#MFRA4518427

4078 Scarlet Iris Pl
Winter Park, FL 32792

4

6

4

7,895 SqFt

Pool

Water Front

3.06 Acres

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We do not have any properties available for sale in Bear Gully Pointe.

0 Active Listings in Bear Gully Pointe