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.

75 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 HOMESERVICES FLORIDA REALTY

MLS# A4454431 - Status: Active View Property Details Add to Favorites View Map

  • 552 EAGLE WATCH LN
  • Price: $3,790,000
  • Zip Code: 34229
  • 6340 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 4+
  • The ultimate in luxury, location and design. As you open the 13' cast iron front doors, you will immediately feel the grandeur of this expansive residence - custom crafted to perfection. Each of the 12 rooms, plus 4.5 baths, are thoughtfully designed ... Read More
  • Listing courtesy of: BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

MLS# A4455608 - Status: Active View Property Details Add to Favorites View Map

  • 68 OSPREY POINT
  • Price: $1,950,000
  • Zip Code: 34229
  • 4571 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 3+
  • Set gracefully amidst lush tropical landscaping in the gated waterfront community of The Oaks Bayside, this stunning residence has been masterfully designed to blend classic architectural elements and exceptional finishes with grand scale and light t ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4456074 - Status: Active View Property Details Add to Favorites View Map

  • 318 OSPREY POINT DR
  • Price: $1,940,000
  • Zip Code: 34229
  • 6981 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 5+
  • Welcome to an exquisite lifestyle at a price you won't believe; all in the world-class, incredibly private Oaks Bayside community. At 318 Osprey Point, you will live without limits across almost 7,000 square feet of stunning space. Encompassing 5 bed ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4456557 - Status: Active View Property Details Add to Favorites View Map

  • 562 N MACEWEN DR
  • Price: $1,700,000
  • Zip Code: 34229
  • 6416 Square Feet
  • Subdivision: OAKS 2
  • Bedrooms: 5 Baths: 6+
  • WHITE GLOVE showings available. The Oaks...Exceptional home, custom built on one of the most beautiful lots in the Oaks Clubside with a private setting w/lake & golf beyond. Over 6200 SF, 5/6 BDRS, 6 BA, 2 offices, 4 car-garages. This remarkable flo ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4456744 - Status: Active View Property Details Add to Favorites View Map

  • 285 SUGAR MILL DR
  • Price: $1,695,000
  • Zip Code: 34229
  • 5578 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 5+
  • 2 BR 2 BATH GUEST HOUSE, 4 CAR GARAGE, AND WALLED MOTOR COURT! You will feel like nobility when you enter this gated lakeside estate in The Oaks Bayside. This spacious 4 bedroom, 5.5 bath gives you all the amenities of an exclusive resort, and the w ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4444745 - Status: Active View Property Details Add to Favorites View Map

  • 350 SUGAR MILL DR
  • Price: $1,450,000
  • Zip Code: 34229
  • 4100 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 3+
  • Pre-Construction. To be built. The Oaks Bayside. One of the few remaining homesites available to build your Dream Home with Henson Contractors. There is no time requirement for building and there is freedom to select another builder of your choice. ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4439437 - Status: Active View Property Details Add to Favorites View Map

  • 860 MACEWEN DR
  • Price: $1,450,000
  • Zip Code: 34229
  • 5084 Square Feet
  • Subdivision: OAKS 2 PH 2
  • Bedrooms: 4 Baths: 6+
  • THE EXCLUSIVE OAKS GOLF & TENNIS COUNTRY CLUB! Only Platinum and Elite club in the Sarasota Area (Top 10 Nationwide). This well designed home with gourmet kitchen has top of the line appliances with adjoining breakfast area, and is open convenientl ... Read More
  • Listing courtesy of: BRIGHT REALTY

MLS# A4428519 - Status: Active View Property Details Add to Favorites View Map

  • 425 MACEWEN DR
  • Price: $1,450,000
  • Zip Code: 34229
  • 5153 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 5+
  • RECENTLY REDUCED! This spacious 5 bedroom, 5.5 bath home offers over 5,100 square feet of living space and overlooks the par 3 fourth hole of The Oaks Heron Course. The huge gourmet kitchen features top of the line stainless steel appliances includin ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4457045 - Status: Active View Property Details Add to Favorites View Map

  • 497 WEBBS CV
  • Price: $1,300,000
  • Zip Code: 34229
  • 6863 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 6 Baths: 6+
  • 6 CAR GARAGE, 2BR 2 BATH GUEST HOUSE ! you seeking a one-of-a-kind home located in the tropics equipped to entertain, and accommodate, all the guests you want to share your luxury lifestyle with? Then you will love this large, unique home in The Oak ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4452379 - Status: Active View Property Details Add to Favorites View Map

  • 676 EAGLE WATCH LN
  • Price: $1,298,575
  • Zip Code: 34229
  • 5399 Square Feet
  • Subdivision: OAKS 2 PH 2
  • Bedrooms: 5 Baths: 6+
  • RECENT 100K PRICE ADJUSTMENT. 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 ... Read More
  • Listing courtesy of: CHARLES RUTENBERG REALTY INC

MLS# A4461840 - Status: Active View Property Details Add to Favorites View Map

  • 689 EAGLE WATCH LN
  • Price: $1,290,000
  • Zip Code: 34229
  • 4975 Square Feet
  • Subdivision: OAKS 2 PH 2
  • Bedrooms: 4 Baths: 3+
  • This spectacular Cape Dutch-style residence is in the sought-after Oaks Club community in Osprey, FL. The spacious and immaculate home is situated at the end of a cul-de-sac overlooking the 7th fairway of one of the two 18-hole championship golf cour ... 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: $1,250,000
  • 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 REALTY

MLS# A4459688 - Status: Active View Property Details Add to Favorites View Map

  • 628 N MACEWEN DR
  • Price: $1,150,000
  • Zip Code: 34229
  • 4486 Square Feet
  • Subdivision: OAKS 2 PH 4-C PT 3
  • Bedrooms: 5 Baths: 4+
  • The OAKS is the most luxurious GOLF and TENNIS community in Sarasota county located on two outstanding golf courses. The Oaks Club was awarded the Distinguished Emerald Club of the World Designation Award. Is the only West Central Florida Country Clu ... Read More
  • Listing courtesy of: HORIZON REALTY INTERNATIONAL

MLS# A4454887 View Property Details Add to Favorites View Map

  • N POINT RD
  • Price: $1,150,000
  • Zip Code: 34229
  • 0 Acres
  • DRAMATIC PRICE REDUCTION, Seller says bring all offers. - The Oaks Preserve Phase IV - Located behind the gates of The Oaks, this 3.12 acre development site is the last remaining developer site in the Oaks and is entitled for 30 single family residen ... Read More
  • Listing courtesy of: SVN COMMERCIAL ADVISORY GROUP

MLS# A4447540 - Status: Active View Property Details Add to Favorites View Map

  • 398 MACEWEN DR
  • Price: $1,150,000
  • Zip Code: 34229
  • 4743 Square Feet
  • Subdivision: OAKS 2 PH 3
  • Bedrooms: 4 Baths: 5+
  • Incredible 4 bedroom, 5.5 bath home with separate guest quarters located behind the gates of the Oaks Clubside. Situated on the 4th fairway of the Eagle course. There is a great deal to love about this large 4,743 square foot house. Custom-built in 1 ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4445561 - Status: Active View Property Details Add to Favorites View Map

  • 413 MACEWEN DR
  • Price: $1,100,000
  • Zip Code: 34229
  • 4152 Square Feet
  • Subdivision: OAKS 2 PH 3
  • Bedrooms: 3 Baths: 3+
  • RECENTLY REDUCED! You will love the incredible light that fills this 3 bedroom plus office, 3.5 bath home in The Oaks Clubside. Situated on a beautiful lot, it offers stunning views of the lake/pond and golf course. With a young roof, refinished po ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4442718 - Status: Active View Property Details Add to Favorites View Map

  • 402 WALLS WAY
  • Price: $1,100,000
  • Zip Code: 34229
  • 3464 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 4 Baths: 3+
  • NEW PRICE makes this home a MUST SEE! Built in 2014 by Todd Johnston Homes, this spectacular courtyard style waterfront property has a separate casita that may be used as a guest quarters, artists studio or in law suite. Situated on a premier corner ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

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 3 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 REALTY

MLS# A4448390 - Status: Active View Property Details Add to Favorites View Map

  • 894 MACEWEN DR
  • Price: $1,075,000
  • Zip Code: 34229
  • 3095 Square Feet
  • Subdivision: OAKS 2 PH 2
  • Bedrooms: 3 Baths: 3
  • 3 Reasons to fall in love...1. LOCATION: The only private, member-owned golf community located minutes from Siesta Key Beach and Downtown Sarasota with easy access to I-75. 2. THE OAKS CLUB: A truly unique lifestyle offering two championship golf cou ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

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

  • 388 BUNKER HILL
  • Price: $990,000
  • 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# A4429579 - Status: Active View Property Details Add to Favorites View Map

  • 53 FAIRWAY OAKS LN
  • Price: $985,000
  • Zip Code: 34229
  • 3774 Square Feet
  • Subdivision: OAKS 2 PH 4-A
  • Bedrooms: 4 Baths: 3+
  • Welcome to The Oaks Sarasota's only 2019-2020 Platinum Clubs of America Recipient. This Custom built home set on a private cul-de-sac is lushly landscaped and boasts over 3700 Sq. Ft. The elegant entrance is lined with columns leading to the covered ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4460109 - Status: Active View Property Details Add to Favorites View Map

  • 401 N POINT RD #901
  • Price: $950,000
  • Zip Code: 34229
  • 2594 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3
  • TWO CAR PRIVATE GARAGE, Are you dreaming of living the luxury condo lifestyle in coastal Florida? If so, open your eyes and look at this opulent 3 bedroom plus den, 3 bath penthouse-level end unit in Meridian at The Oaks Preserve. A dream come true, ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4453855 - Status: Active View Property Details Add to Favorites View Map

  • 566 EAGLE WATCH LN
  • Price: $950,000
  • Zip Code: 34229
  • 4553 Square Feet
  • Subdivision: OAKS 2 PH 2
  • Bedrooms: 4 Baths: 4+
  • BRAND NEW ROOF! 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 lux ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4446588 - Status: Active View Property Details Add to Favorites View Map

  • 366 MACEWEN DR
  • Price: $947,000
  • Zip Code: 34229
  • 3517 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 3 Baths: 3+
  • ENJOY the incredible 3D VIRTUAL TOUR and AERIAL VIDEO of this STUNNING, Custom-Built, 3 Bed / 3.5 Bath, Pool/Spa home situated on the 3rd tee of the Eagle Golf Course. Located Very Close to the Clubhouse, this is the perfect home for entertaining an ... Read More
  • Listing courtesy of: GENEROUS PROPERTY

75 listings found