The Oaks Club - Osprey FL Real Estate

Located in Osprey on the east and west sides of Hwy 41, homes in the Oaks Country Club are dynamic, from contemporary to Georgian design. The grounds comprise a gated golf course community and consists of over 1,000 acres and a portion of the property is on Little Sarasota Bay. The community offers residents championship golf on the Eagle and the Heron courses, Har-Tru tennis courts, pool, croquet and a fabulous clubhouse. Single family homes are priced from high $500,000s.

A natural habitat for eagles, egrets, blue heron, bobcats, you'll see more than you can imagine in this gorgeous neighborhood. The Oaks is an active community where families and retirees enjoy a complete resort lifestyle.

Club Amenities

  • Two Championship golf courses
  • 12 Har-Tru tennis courts
  • Swimming Pool
  • Regulation Croquet Court
  • Multiple Dining Venues
  • Golf & Tennis Pro Shops
Browse all homes for sale in the Oaks Club. Check out your options and call or email us if you would like details on any of these properties. You can also click the "Request More Info" button for a quick reply on any property.
The Oaks Club January 16, 2019
41
Listed
183
Avg. DOM
$260.34
Avg. $ / Sq.Ft.
$1,050,000
Med. List Price
41 Properties Found. Showing 1-12
Sort By:
112 Osprey Point Drive
Osprey, FL 34229
112 Osprey Point Drive Osprey, FL 34229
1 of 50
$4,450,000
Subdivision: Oaks
BEDS
6
BATHS
7
SQ.FT.
8,973
BUILT
1989
ON SITE
51Days
MLS
A4419954
Most desirable location in The Oaks Bayside Country Club; truly a boater's Dream! Featuring your own Private Dock with 3 Power Lifts..12,000/16,000. Driving thru this Private Gated Community you are...
136 Osprey Point Drive
Osprey, FL 34229
136 Osprey Point Drive Osprey, FL 34229
1 of 50
$2,790,000
Subdivision: Oaks
BEDS
5
BATHS
8
SQ.FT.
6,461
BUILT
2005
ON SITE
38Days
MLS
A4420948
Opportunity of a Life Time! This magnificent three-level mansion is located in the exclusive private gated community Oaks Bayside. This home is priced to sell and is below market and replacement...
91 Osprey Point Drive
Osprey, FL 34229
91 Osprey Point Drive Osprey, FL 34229
1 of 25
$1,995,000 ( $380,000 )
Subdivision: Oaks
BEDS
4
BATHS
6
SQ.FT.
5,100
BUILT
1983
ON SITE
355Days
MLS
A4208052
Iconic architecture in Sarasota's premiere golf and country club. This magnificent 4-bedroom estate was designed and built by Bo MacEwen and brims with the essence of warm, Southern hospitality. Bo...
95 Osprey Point Drive
Osprey, FL 34229
95 Osprey Point Drive Osprey, FL 34229
1 of 50
$1,900,000 ( $200,000 )
Subdivision: Oaks
BEDS
5
BATHS
6
SQ.FT.
7,531
BUILT
1990
ON SITE
116Days
MLS
A4413743
A FRENCH CHATEAU/PRIVATE MINI ESTATE. 4 car garage. A 3/4 ACRE PARCEL (2 lots) newly landscaped viewing the saltwater pool and large lake. Main house 6500 SQ FT and with guest house 7531 SQ FT....
168 Coastal Hammock Court
Osprey, FL 34229
168 Coastal Hammock Court Osprey, FL 34229
1 of 24
$1,599,000
Subdivision: Oaks
BEDS
3
BATHS
4
SQ.FT.
4,924
BUILT
1993
ON SITE
63Days
MLS
A4419256
Bayfront in the Oaks. Custom designed walled Mizner-style estate in private cul-de-sac location with a 5 stop elevator. Views from several areas showcasing the gulf and bay. Very livable floor plan...
676 Eagle Watch Lane
Osprey, FL 34229
676 Eagle Watch Lane Osprey, FL 34229
1 of 25
$1,445,000
Subdivision: Oaks 2
BEDS
5
BATHS
7
SQ.FT.
5,399
BUILT
1992
ON SITE
16Days
MLS
A4215527
Just Reduced $100,000. Classic elegance at The Oaks Club Side! This custom built 5400sf single story has been extensively renovated to include fresh interior paint throughout, new high-end hardwood...
586 N Macewen Drive
Osprey, FL 34229
586 N Macewen Drive Osprey, FL 34229
1 of 44
$1,425,000 ( $100,000 )
Subdivision: Oaks
BEDS
4
BATHS
6
SQ.FT.
4,163
BUILT
2001
ON SITE
163Days
MLS
A4410275
Exceptional and meticulously maintained best describes this fabulous 4100+ sf, 4 bedroom, 5 1/2 bath, 5-car garage residence with golf course views in the highly acclaimed gated golf community - The...
419 Walls Way
Osprey, FL 34229
419 Walls Way Osprey, FL 34229
1 of 42
$1,400,000 ( $250,000 )
Subdivision: Oaks 2
BEDS
4
BATHS
5
SQ.FT.
5,523
BUILT
1988
ON SITE
380Days
MLS
A4203589
A recent price reduction makes this spectacular 4 bedroom, 4.5 bath colonial, with over $1,000,000 in renovations, an opportunity too good to pass by! If you are a discriminating buyer, seeking the...
497 Webbs Cove
Osprey, FL 34229
497 Webbs Cove Osprey, FL 34229
1 of 25
$1,390,000
Subdivision: Oaks
BEDS
6
BATHS
7
SQ.FT.
6,863
BUILT
1992
ON SITE
10Days
MLS
A4423128
Seller will pay $25k toward club membership with approved contract. Located in the exclusive gated community of The Oaks Bayside. Totally remodeled home with too many improvements to list, everything...
340 Osprey Point Drive
Osprey, FL 34229
340 Osprey Point Drive Osprey, FL 34229
1 of 50
$1,350,000 ( $150,000 )
Subdivision: Oaks
BEDS
5
BATHS
7
SQ.FT.
6,002
BUILT
1998
ON SITE
352Days
MLS
A4207974
If you want to live an enviable lifestyle with the comfort of being surrounded by nature, combined with the elegance of country club living, this 5 bedroom French Country styled home, with 5 full and...
388 Bunker Hill
Osprey, FL 34229
388 Bunker Hill Osprey, FL 34229
1 of 25
$1,300,000
Subdivision: Oaks 2
BEDS
4
BATHS
6
SQ.FT.
4,937
BUILT
1999
ON SITE
171Days
MLS
A4409213
Lush, luxurious, and private. This beautiful residence located in the much sought-after Oaks Club community offers a large, warm home situated at the end of a cul-de-sac on lushly landscaped grounds....
644 Fernwalk Lane
Osprey, FL 34229
644 Fernwalk Lane Osprey, FL 34229
1 of 40
$1,200,000
Subdivision: Oaks
BEDS
3
BATHS
4
SQ.FT.
3,793
BUILT
1989
ON SITE
22Days
MLS
A4420718
This traditional 3/4 bedroom, 4 bath home in The Oaks Bayside offers elegant country club living, with panoramic vistas of the lake and golf course. From the moment you drive down the private...

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