The Oaks Club

The Oaks Club is a gated community of single family homes and condos in Osprey, Florida, with a range of options priced between $300,000 and $3,995,000. There are currently a total of 14 homes for sale in The Oaks Club. The smallest Oaks Club home presently available is a two bedroom two bathroom residence that is 677 square feet (623SF Under Air living space), and the largest of the The Oaks Club homes currently on the market has six beds and six baths and is a 11,650 square foot (9,081SF 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 The Oaks Club range from $399 to $850 and $425 for a The Oaks Club condo. This fee includes common area maintenance, grounds maintenance, building maintenance, maintaining the community roads, the community pool, and security. Also included is a 24-hour guard, real estate taxes for common areas, property insurance, water, trash removal, sewer, pest control, internet, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular The Oaks Club home.

The Oaks Club amenities include a clubhouse, swimming pool, spa / hot tub, a state-of-the-art fitness center, and sauna. Sports facilities include a championship golf course, tennis courts, pickleball courts, racquetball, and basketball court.

The Oaks Club HOA rules do allow homeowners to have pets. There is a limit of how many pets you may have, and there is a restriction on pet size. Dogs and cats are allowed.

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

The Oaks Club real estate activity on the Osprey MLS during the past year (as of February 2026) reflects seventeen homes changing hands, with an average asking price of $2,030,412 and an average selling price of $1,885,235. This represents a healthy list-to-sell price ratio of 93% and $330 per square foot. During this period, The Oaks Club homes for sale have taken an average of 64 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 The Oaks Club are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in The Oaks Club 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.

The Oaks Club Homes For Sale

Under Contract

$3.995 Million

MLS#MFRA4668477

691 Eagle Watch Ln
Osprey, FL 34229

4

7

4

9,482 SqFt

Pool

0.78 Acres

111 Days

Reduced

$3,890,000

$3,950,000

MLS#MFRA4668918

854 Macewen Dr
Osprey, FL 34229

4

6

4

11,650 SqFt

Pool

0.78 Acres

128 Days

Reduced

$2,700,000

$2,900,000

MLS#MFRA4644125

236 Saint James Park
Osprey, FL 34229

6

7

2

9,589 SqFt

Pool

0.56 Acres

334 Days

Reduced

$2,495,000

$2,550,000

MLS#MFRA4659276

852 Macewen Dr
Osprey, FL 34229

3

4

3

6,019 SqFt

Pool

0.64 Acres

219 Days

$2,450,000

MLS#MFRA4679288

896 Macewen Dr
Osprey, FL 34229

4

6

3

6,688 SqFt

Pool

0.59 Acres

33 Days

$2,400,000

MLS#MFRA4683029

530 N Mac Ewen Dr
Osprey, FL 34229

4

6

3

5,837 SqFt

Pool

0.61 Acres

4 Days

$2,250,000

MLS#MFRA4676505

433 E Macewen Dr
Osprey, FL 34229

4

4

3

5,670 SqFt

Pool

0.61 Acres

56 Days

$2,249,000

MLS#MFRA4676567

362 Macewen Dr
Osprey, FL 34229

4

4

3

5,478 SqFt

Pool

0.59 Acres

43 Days

$2,195,000

MLS#MFRA4668497

600 Eagle Watch Ln
Osprey, FL 34229

3

3

3

5,157 SqFt

Pool

0.71 Acres

126 Days

Reduced

$2,100,000

$2,300,000

MLS#MFRA4669491

538 Dove Pointe Dr
Osprey, FL 34229

4

6

3

5,837 SqFt

Pool

0.83 Acres

109 Days

$1,800,000

MLS#MFRA4680312

401 Walls Way
Osprey, FL 34229

4

4

3

5,403 SqFt

Pool

0.6 Acres

25 Days

Reduced

$1,695,000

$1,795,000

MLS#MFRA4621683

909 Macewen Dr
Osprey, FL 34229

3

4

2

5,495 SqFt

Pool

0.56 Acres

529 Days

14 Active Listings in The Oaks Club