Bayside Osprey

Bayside is a luxury gated community of single family homes in Osprey, Florida, with a range of options priced between $997,000 and $1,367,500. The smallest Bayside home in the community is a three bedroom three bathroom residence that is 2,950 square feet (2,115SF Under Air living space), and the largest of the Bayside homes has three beds and three baths and is a 3,593 square foot (2,391SF Under Air) residence.

Property management fees in Sarasota County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Bayside range from $1,309 to $1,343. This fee includes grounds maintenance, building maintenance, maintaining the community roads, and real estate taxes for common areas. Please check the individual listing pages for the exact homeowners association fees for a particular Bayside home.

The Bayside HOA rules do allow homeowners to have pets although there are certain breed restrictions. There is a limit of how many pets you may have. Dogs and cats are allowed.

There are two commercial airports that serve Bayside - Sarasota Bradenton International (SRQ), which is fifteen miles away, and Punta Gorda (PGD), which is 36 miles away.

Bayside real estate activity on the Osprey MLS during the past year (as of September 2025) reflects two homes changing hands, with an average asking price of $1,108,500 and an average selling price of $1,092,500. This represents a healthy list-to-sell price ratio of 99% and $311 per square foot. During this period, Bayside homes for sale have taken an average of 111 days to sell.

In addition, there are numerous other communities in Osprey to choose from, or you may browse all available Osprey Real Estate, including some new construction opportunities. Homes for sale in Bayside are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Bayside hits the market. You can also always contact your ZFC Real Estate agent, who would happily assist you further with all your Florida real estate needs.

Bayside Homes For Sale

SOLD 05/07/24

$1,250,000

$1,295,000

MLS#MFRA4599137

3925 Waypoint Ave
Osprey, FL 34229

3

3

2

3,248 SqFt

Pool

0.18 Acres

SOLD 12/30/22

$1 Million

$1,100,000

MLS#MFRA4547021

3929 Waypoint Ave
Osprey, FL 34229

3

4

2

2,115 SqFt

Pool

0.22 Acres

SOLD 09/23/24

$1,220,000

MLS#MFRA4615178

3933 Waypoint Ave
Osprey, FL 34229

3

3

3

3,424 SqFt

Pool

0.19 Acres

SOLD 04/24/24

$1,250,000

$1,310,000

MLS#MFRA4593940

3937 Waypoint Ave
Osprey, FL 34229

3

3

2

3,311 SqFt

Pool

0.17 Acres

SOLD 08/08/25

$997,000

$1,189,000

MLS#MFRA4636439

3904 Waypoint Ave
Osprey, FL 34229

3

3

3

3,593 SqFt

Pool

Water Front

0.17 Acres

SOLD 05/21/24

$1,159,000

$1,365,000

MLS#MFRA4584138

3961 Waypoint Ave
Osprey, FL 34229

3

3

3

3,408 SqFt

Pool

0.18 Acres

SOLD 04/01/24

$1,100,000

$1,200,000

MLS#MFRA4589382

3973 Waypoint Ave
Osprey, FL 34229

3

3

2

2,950 SqFt

Pool

0.2 Acres

SOLD 08/31/23

$1,367,500

MLS#MFRA4578201

3932 Waypoint Ave
Osprey, FL 34229

3

3

3

3,400 SqFt

Pool

Water Front

0.19 Acres

SOLD 09/26/22

$1,300,000

MLS#MFRA4544067

3932 Waypoint Ave
Osprey, FL 34229

3

3

3

3,400 SqFt

Pool

Water Front

0.19 Acres

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We do not have any properties available for sale in Bayside.

You may also be interested in Bayside in Port Orange, Bayside in Clearwater or Bayside in Cape Canaveral.

0 Active Listings in Bayside