The Oaks Club

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The Oaks Club Real Estate for Sale – Osprey, Florida 34229

The Oaks Club Real Estate

The Oaks Club highly regarded as a golf and residential real estate gem in Osprey, Sarasota County, brings the legacy of an incomparable lifestyle to this world class location. This is why The Oaks Club real estate development is one to rave about. The development was founded at the turn of the 20th century by Bertha Honoré Palmer, one of the early pioneers who owned a substantial parcel of Sarasota real estate.

The Oaks Club merges the allure of a golf and waterfront community with its delightful setting on the shores of the peaceful Intracoastal waterway. Located in Osprey, it’s far enough to the south of Sarasota to get you away from all the US-41, Bee Ridge, Fruitville, and downtown Sarasota traffic. With The Oaks Club situated directly on the Intracostal Waterway, the cool breezes off the water will bring enormous relief during the sizzling Sarasota summers.

The heart of social life at The Oaks is in its majestic, 34,000 square foot clubhouse. The distinguished confines of the club presents a refined range of social amenities for entertaining and dining suiting diverse occasions and tastes. Formal dining is featured in The Glen Room and informal or more casual dining is enjoyed in The Tavern or The Grill Room where friends can swap golf stories and avail of the liberal collections of wines and spirits.

Filling the busy social calendar for members are activities like lively dinner dances and theme parties, as well as more informal pursuits such as competitive bridge and mah-jong games. The club also holds various special events throughout the year through several local social associations. For more physically active members, sporting amenities abound in the tennis center featuring 12 Har-Tru tennis courts with 4 being lighted for night play, a tournament croquet court, and a sparkling junior Olympic-size swimming pool with an adjacent children’s playground.

For those who are considering owning real estate at The Oaks Club and will be looking for membership, the 2 options are equity and social and either is mandatory if you wish to reside in the community. There are associate memberships available for non-residents for golf, tennis, and junior tennis.

The Oaks Club Golf Courses

The Oaks Club Real Estate

The championship golf courses that are woven into the fabric of The Oaks’ community are comprised of 2 challenging, 18-hole, par 72 layouts. The Eagle, designed by world famous course architect, Arthur Hills, is acclaimed as one of the best in Southwest Florida. The course features a slope rating of 147, measures out at 5,022 yards from the front tees, and extends to a beautiful 7,003 yards from the back markers, enabling options to fit the skill sets of all duffers.

Officially opened in 1984, the Heron course was thoughtfully designed by another heralded course architect, William Byrd. Comparable options are obtainable at this course which measures 6,695 yards from the farthest tees and 4,986 yards from the nearest. It has a set of five tee boxes with a slope rating of 136.

Additional member privileges at The Oaks Club include state of the art equipment and weekly golf clinics available at the practice facilities. Along with the expansive, full service locker rooms, there is a pro shop with a wealth of cutting edge golf equipment, contemporary sports accessories, and the latest in fashionable apparel. The club also features reciprocal summer play agreements with other golf clubs in the immediate area.

The Oaks Club Real Estate

The Oaks Club Real Estate

Numerous and diverse lifestyle preferences and options await those seeking to buy real estate in The Oaks Club. This gated residential community is composed of three unique neighborhoods namely the Oaks Bayside, the Oaks Clubside, and the Oaks Preserve.

Boasting 4 distinct subdivisions, most of The Oaks Club real estate options are offered at the Oaks Preserve. One subdivision, The Bishopscourt, is composed of ranch type villas and 2 story homes while the Bishopscourt Townhomes encompasses a mini-complex of two maintenance free residential buildings, a clubhouse, and a pool. The Emerald Woods subdivision consists of maintenance free villas and the Meridian is an enclave taking in 4, 10 story condos overlooking Sarasota Bay.

Real estate for sale at the Oaks Club can include condos with price points in the $300,000 range or a mansion sized estate home priced at over $7 million.


The Oaks Club Homes for Sale

The Oaks Club consists of three gated neighborhoods, The Oaks Bayside features 197 homes sites with many homes directly on Little Sarasota Bay. The Oaks Clubside features 358 estate sized home sites bordering The Oaks Club golf courses. The Oaks Preserve features preserve home sites in a natural estuary. Meridian at The Oaks Preserve is a bay front condominium development within the preserve.

80 listings found

MLS# A4419954 - Status: Active View Property Details Add to Favorites View Map

  • 112 OSPREY POINT DR
  • Price: $4,450,000
  • Zip Code: 34229
  • 8973 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 6 Baths: 6+
  • 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 surrounded by a Canopy of Mature Oak trees. The Gra ... Read More
  • Listing courtesy of: BERKSHIRE HATHAWAY HOMESERVICE

MLS# A4420948 - Status: Active View Property Details Add to Favorites View Map

  • 136 OSPREY POINT DR
  • Price: $2,790,000
  • Zip Code: 34229
  • 6461 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 5+
  • 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 value. Exquisite Brazillan cherry wood flooring through ... Read More
  • Listing courtesy of: BERKSHIRE HATHAWAY HOMESERVICE

MLS# A4205202 View Property Details Add to Favorites View Map

  • N POINT RD
  • Price: $2,495,000
  • Zip Code: 34229
  • 0 Acres
  • The Oaks Preserve Phase IV - Located behind the gates of The Oaks, this 3.12 acre development site is entitled for 30 single family residential units. The zoning allows for up to four stories and great flexibility in the type of home product includin ... Read More
  • Listing courtesy of: SVN Commercial Advisory Group

MLS# A4208052 - Status: Active View Property Details Add to Favorites View Map

  • 91 OSPREY POINT DR
  • Price: $1,995,000
  • Zip Code: 34229
  • 5100 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 5+
  • 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 was the original architect for The Oaks and he creat ... Read More
  • Listing courtesy of: Michael Saunders & Company

MLS# A4413743 - Status: Active View Property Details Add to Favorites View Map

  • 95 OSPREY POINT DR
  • Price: $1,900,000
  • Zip Code: 34229
  • 7531 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 5+
  • 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. Place your long term guests in the separate 1000 SQ FT ... Read More
  • Listing courtesy of: MY REALTY COMPANY

MLS# A4419256 - Status: Active View Property Details Add to Favorites View Map

  • 168 COASTAL HAMMOCK CT
  • Price: $1,599,000
  • Zip Code: 34229
  • 4924 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 3 Baths: 3+
  • 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 with expansive master suite offering a separate sitt ... Read More
  • Listing courtesy of: CROWN PROPERTIES GROUP INC

MLS# A4208738 - Status: Active View Property Details Add to Favorites View Map

  • 409 N POINT RD #1003
  • Price: $1,500,000
  • Zip Code: 34229
  • 2778 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3
  • $150K price improvement! Owner wants it sold - bring all offers! The best views in all of Meridian! Experience the luxurious Florida lifestyle with gorgeous open views that encompass Casey Key, Siesta Key, Downtown Sarasota, Little Sarasota Bay & t ... Read More
  • Listing courtesy of: RE/MAX Alliance Group

MLS# A4215527 - Status: Active View Property Details Add to Favorites View Map

  • 676 EAGLE WATCH LN
  • Price: $1,445,000
  • Zip Code: 34229
  • 5399 Square Feet
  • Subdivision: OAKS 2 PH 2
  • Bedrooms: 5 Baths: 6+
  • 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 floors and new bathrooms. Master suite has 2 large ... Read More
  • Listing courtesy of: Charles Rutenberg Realty Inc

MLS# A4410275 - Status: Active View Property Details Add to Favorites View Map

  • 586 N MACEWEN DR
  • Price: $1,425,000
  • Zip Code: 34229
  • 4163 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 5+
  • 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 Oaks Club. A serene and private setting, with gol ... Read More
  • Listing courtesy of: BERKSHIRE HATHAWAY HOMESERVICE

MLS# A4203589 - Status: Active View Property Details Add to Favorites View Map

  • 419 WALLS WAY
  • Price: $1,400,000
  • Zip Code: 34229
  • 5523 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 4 Baths: 4+
  • 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 utmost in fine, country club living, you need to loo ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4423128 - Status: Active View Property Details Add to Favorites View Map

  • 497 WEBBS CV
  • Price: $1,390,000
  • Zip Code: 34229
  • 6863 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 6 Baths: 6+
  • 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 is new including; new roof, air conditioners, new ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4207974 - Status: Active View Property Details Add to Favorites View Map

  • 340 OSPREY POINT DR
  • Price: $1,350,000
  • Zip Code: 34229
  • 6002 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 5+
  • 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 2 half baths is perfect for you! Play an early rou ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4409213 - Status: Active View Property Details Add to Favorites View Map

  • 388 BUNKER HL
  • Price: $1,300,000
  • Zip Code: 34229
  • 4937 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 4 Baths: 4+
  • 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. High ceilings, marble flooring, crown molding and ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4420718 - Status: Active View Property Details Add to Favorites View Map

  • 644 FERNWALK LN
  • Price: $1,200,000
  • Zip Code: 34229
  • 3793 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 3 Baths: 4
  • 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 cul-de-sac street, and get your first view of this home, y ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4410358 - Status: Active View Property Details Add to Favorites View Map

  • 97 SUGAR MILL DR
  • Price: $1,180,000
  • Zip Code: 34229
  • 4902 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 5+
  • A storybook modern day estate awaits behind the gates of The Oaks Bayside, an opulent country club community in Osprey. Discover this beautifully proportioned architectural gem perfectly nestled amid luxuriant mature landscaping. Two paver driveways ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4423415 - Status: Active View Property Details Add to Favorites View Map

  • 384 BUNKER HILL
  • Price: $1,175,000
  • Zip Code: 34229
  • 3794 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 4 Baths: 3+
  • Looking for true country club living... this 4 bedroom, 3 1/2 bath home is a must see. Located behind the gates of the Oaks with views of the lake and the third green of the Eagle golf course. This Arthur Rutenberg home is well appointed and meticulo ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4199246 - Status: Active View Property Details Add to Favorites View Map

  • 738 N MACEWEN DR
  • Price: $1,175,000
  • Zip Code: 34229
  • 4614 Square Feet
  • Subdivision: OAKS 2 PH 4-C PT 2
  • Bedrooms: 5 Baths: 5+
  • Imagine how you'd like to live the ultimate Florida lifestyle. Your vision can become a reality in this 5 bedroom, 5.5 bath two story home in The Oaks Clubside. Set back on a cul-de-sac lot, with gorgeous lake and golf views, the floor plan offers fl ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4419253 - Status: Active View Property Details Add to Favorites View Map

  • 922 MACEWEN DR
  • Price: $1,150,000
  • Zip Code: 34229
  • 4520 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 4+
  • Style and sophistication exude on this gorgeous Oaks clubside home that is perfectly situated on a lushly landscaped oversized lot with views of golf and lake beyond. This five bedroom, four full bath, two half bath home will provide the perfect atmo ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4422927 - Status: Active View Property Details Add to Favorites View Map

  • 566 EAGLE WATCH LN
  • Price: $1,100,000
  • Zip Code: 34229
  • 4553 Square Feet
  • Subdivision: OAKS 2 PH 2
  • Bedrooms: 4 Baths: 4+
  • This 4 bedroom, 4.5 custom-built home is a study in elegance. From the impressive marble entryway to the magnificent large lanai with pool spa and gorgeous golf course views, this home has all the touches you would expect in a luxurious county club h ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4422405 - Status: Active View Property Details Add to Favorites View Map

  • 464 WALLS WAY
  • Price: $1,100,000
  • Zip Code: 34229
  • 4826 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 3 Baths: 3+
  • This uniquely designed, custom built 4 bedroom, 3.5 bath home is a country club enthusiast's dream come true! Situated on a cul-de-sac on the Heron Course in The Oaks Clubside, this magnificent home was built by Baron Construction. The impressive ex ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4411229 - Status: Active View Property Details Add to Favorites View Map

  • 401 N POINT RD #1003B3
  • Price: $1,100,000
  • Zip Code: 34229
  • 2778 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 4 Baths: 3
  • Penthouse, please. Just two little words and one big smile the next time you're on the elevator and someone asks you what floor?. Yes, you have arrived. As the elevator delivers you directly to your door, on entering your eye is first drawn to seemin ... Read More
  • Listing courtesy of: RE/MAX ALLIANCE GROUP

MLS# A4400278 - Status: Active View Property Details Add to Favorites View Map

  • 67 SUGAR MILL DR
  • Price: $1,100,000
  • Zip Code: 34229
  • 4020 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 3+
  • This traditional 4 bedroom, 3.5 bath (plus pool bath) home exudes sophistication. From the moment you approach, the style & grace of this masterpiece is apparent. Pass through the columned entrance way, open the front door & imagine what it would be ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4201268 - Status: Active View Property Details Add to Favorites View Map

  • 165 SUGAR MILL DR
  • Price: $1,100,000
  • Zip Code: 34229
  • 3912 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 4+
  • Picture this. Gracious country club living on the Bayside of The Oaks Club in this 4 bedroom, 4.5 bath home. As you enter the new paver circular driveway, with three car side entry garage, it is evident how special this house is. Ideally situated ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4423391 - Status: Active View Property Details Add to Favorites View Map

  • 852 MACEWEN DR
  • Price: $1,050,000
  • Zip Code: 34229
  • 4519 Square Feet
  • Subdivision: OAKS 2 PH 2
  • Bedrooms: 3 Baths: 3+
  • Elegant Family Home locate in the desirable Oaks Golf & Country Club. This spectacular home features 3 bedrooms and 3.5 baths sits on an oversized lot over looking the Heron Golf Course. Enjoy the open living/dining area with beautiful hardwood floo ... Read More
  • Listing courtesy of: BRIGHT REALTY

MLS# A4415404 - Status: Active View Property Details Add to Favorites View Map

  • 466 E MACEWEN DR
  • Price: $1,050,000
  • Zip Code: 34229
  • 3754 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 4
  • Welcome to The Oaks, Sarasota's only 2019-2020 Platinum Clubs of America Recipient. This custom built Garry Group home boasts 4 bedroom 4 bathroom and is truly a Southern charmer. Traditional combined with perfectly symmetrical style with 3700+ sq. f ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

80 listings found