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.

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

  • 285 SUGAR MILL DR
  • Price: $1,895,000
  • Zip Code: 34229
  • 5578 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 5+
  • This custom designed home is the must-see property in The Oaks. With space for family, working from home and for guests or multigenerational living, this private sanctuary has everything--style, luxury, and a great location, minutes from downtown and ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

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

  • 318 OSPREY POINT DR
  • Price: $1,840,000
  • Zip Code: 34229
  • 6981 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 5+
  • Built in 2008, the NEWEST resale home available in The Oaks Club. Located on a super private street with a 24-7 manned gate entrance in one of Sarasota's most highly regarded golf & country club neighborhoods. If you haven't heard it yet, West of Tra ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4466028 - Status: Active View Property Details Add to Favorites View Map

  • 468 WALLS WAY
  • Price: $1,600,000
  • Zip Code: 34229
  • 5698 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 5 Baths: 4+
  • This 4 bedroom home with 4 baths, and 2 half bath enjoys one of the best locations in the Oaks Clubside. Idyllically situated at the end of a cul-de-sac, on a beautifully landscaped half acre lot, this home offers privacy, tranquility and beautiful ... 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: $1,550,000
  • Zip Code: 34229
  • 6416 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 6+
  • THE PERFECT HOME FOR QUARANTINE AND WORKING FROM HOME WITH 2 SEPARATE OFFICES, STUDIO/EXERCISE ROOM, BONUS ROOM FOR HOME SCHOOLING, 5 BEDROOMS!! Exceptional home in the Oaks, custom built on one of the most beautiful lots in the Oaks Clubside w/a pr ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4462606 - Status: Active View Property Details Add to Favorites View Map

  • 597 N MACEWEN DR
  • Price: $1,395,000
  • Zip Code: 34229
  • 5610 Square Feet
  • Subdivision: OAKS 2 PH 4-C PT 3
  • Bedrooms: 5 Baths: 5+
  • ENJOY the 3D VIRTUAL TOUR of this ELEGANT, Custom-Built, 5-6 Bed / 5.5 Bath, Pool/Spa, Luxury Estate situated on the 16th fairway of the Heron Golf Course. Relish in the coveted lifestyle of The Oaks Club, featuring Luxury Coastal Living in the Heart ... Read More
  • Listing courtesy of: GENEROUS PROPERTY

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

  • 676 EAGLE WATCH LN
  • Price: $1,295,000
  • Zip Code: 34229
  • 5399 Square Feet
  • Subdivision: OAKS 2 PH 2
  • Bedrooms: 5 Baths: 6+
  • RECENT PRICE ADJUSTMENT. Classic elegance at The Oaks Club Side! Owner will entertain owner financing, or a trade for smaller residential or commercial property. This custom built 5400sf single story has been extensively renovated to include fresh in ... Read More
  • Listing courtesy of: CHARLES RUTENBERG REALTY INC

MLS# A4474975 - Status: Active View Property Details Add to Favorites View Map

  • 933 BLUE HERON OVERLOOK
  • Price: $1,275,000
  • Zip Code: 34229
  • 4856 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 5 Baths: 4+
  • What would the lot premium be for this location if you were building new?...Premier Cul de Sac location in The Oaks Clubside - Picturesque sunset views from 2900 sqft Lanai that also overlooks Heron's#1 Green - Entertaining is a breeze in single floo ... Read More
  • Listing courtesy of: WADE F DIRR LIC R.E. BROKER

MLS# A4478203 - Status: Active View Property Details Add to Favorites View Map

  • 689 EAGLE WATCH LN
  • Price: $1,185,000
  • 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# A4476281 - Status: Active View Property Details Add to Favorites View Map

  • 388 BUNKER HILL
  • Price: $1,150,000
  • Zip Code: 34229
  • 4937 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 5 Baths: 4+
  • Situated at the end of a cul-de-sac behind the gates of The Oaks, this 5 bedroom home with four full and two half baths, exudes warm and charm. Beautifully set on a verdant lot, the rich vegetation gives the home a feeling of calm, tropical privacy. ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

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# A4476819 - Status: Active View Property Details Add to Favorites View Map

  • 721 N MACEWEN DR
  • Price: $1,125,000
  • Zip Code: 34229
  • 4813 Square Feet
  • Subdivision: OAKS 2 PH 4-C PT 1
  • Bedrooms: 5 Baths: 4+
  • *ENJOY the 3D VIRTUAL TOUR* of this UPDATED and SPACIOUS, 5-Bed / 6-Bath, Pool/Spa home with ideal South-facing lanai, situated on the 17th Fairway of the Heron Golf Course - with breathtaking golf course views! Relish in the coveted lifestyle of The ... Read More
  • Listing courtesy of: GENEROUS PROPERTY

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

  • 398 MACEWEN DR
  • Price: $1,100,000
  • Zip Code: 34229
  • 4743 Square Feet
  • Subdivision: OAKS 2 PH 3
  • Bedrooms: 4 Baths: 5+
  • One or more photo(s) has been virtually staged. SELLER WILL CREDIT WILL BUYER $40,000 TOWARDS OAKS CLUB DUES! Incredible 4 bedroom, 5.5 bath home with separate guest quarters located behind the gates of the Oaks Clubside. Situated on the 4th fairway ... 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# A4476879 - Status: Active View Property Details Add to Favorites View Map

  • 34 OSPREY POINT DR
  • Price: $1,050,000
  • Zip Code: 34229
  • 4696 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 3 Baths: 3+
  • This incredible 3 bedroom, 3.5 bath true brick home is in a class by itself. Distinctly different from other homes in the community, you can enjoy all the unique features of living here, plus all the amenities of living in The Oaks Bayside. Majestica ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4472012 - Status: Active View Property Details Add to Favorites View Map

  • 393 N POINT RD #801
  • Price: $1,000,000
  • Zip Code: 34229
  • 3029 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3
  • Rare in every way, this 3 bedroom, 3 bath penthouse, with private two car garage, is only one of six units in Meridian that enjoys this incredible floor plan. The elegant interior is punctuated by spectacular views. This residence provides everything ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4472373 - Status: Active View Property Details Add to Favorites View Map

  • 558 DOVE POINTE
  • Price: $899,000
  • Zip Code: 34229
  • 3654 Square Feet
  • Subdivision: OAKS 2 PH 4-C PT 3
  • Bedrooms: 3 Baths: 3
  • Located in the winding estate neighborhood of The Oaks, this exceptional home sits on a prime 3/4-acre corner lot with serene water and preserve views. The circular drive and double-entry front doors provide a perfect entrance to the gracious custom ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4471323 - Status: Active View Property Details Add to Favorites View Map

  • 431 MACEWEN DR
  • Price: $850,000
  • Zip Code: 34229
  • 4184 Square Feet
  • Subdivision: OAKS 2 PH 3
  • Bedrooms: 3 Baths: 4
  • Located on the par three, 4th hole of the Heron Golf Course, this 3 bedroom, 4 bath former model, built by Rivolta, is simply grand. Soaring 12ft ceilings throughout, flooding each room with sunlight. The perfect home for entertaining as all the mai ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4445704 - Status: Active View Property Details Add to Favorites View Map

  • 423 MACEWEN DR
  • Price: $850,000
  • Zip Code: 34229
  • 3832 Square Feet
  • Subdivision: OAKS 2 PH 3
  • Bedrooms: 4 Baths: 3+
  • Recently reduced by motivated seller. Don't wait to take advantage of this incredible opportunity to live the luxury country club lifestyle on the gorgeous Gulf Coast! Set back on a beautiful corner cul-de-sac lot in The Oaks Clubside, this custom bu ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4438190 - Status: Active View Property Details Add to Favorites View Map

  • 353 SUGAR MILL DR
  • Price: $850,000
  • Zip Code: 34229
  • 3667 Square Feet
  • Subdivision: OAKS CLUB
  • Bedrooms: 3 Baths: 3+
  • RECENTLY REDUCED! Stunning lake views and a parklike setting add the exclamation point to this beautiful 3 bedroom, 3.5 bath home, designed and built by Arthur Rutenberg. A circular driveway with a 3-car side entry garage, surrounded by lush mature l ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4474830 - Status: Active View Property Details Add to Favorites View Map

  • 731 N MACEWEN DR
  • Price: $849,900
  • Zip Code: 34229
  • 3192 Square Feet
  • Subdivision: OAKS 2 PH 4-C PT 1
  • Bedrooms: 4 Baths: 4
  • ENJOY the 3D VIRTUAL TOUR of this ELEGANT, Beautifully UPDATED, 4 Bed / 4 Bath, Luxury Estate situated on the 17th fairway of the Heron Golf Course. **$40,000 Membership PAID BY SELLER with suitable offer. Relish in the coveted lifestyle of The Oaks ... Read More
  • Listing courtesy of: GENEROUS PROPERTY

MLS# A4423394 - Status: Active View Property Details Add to Favorites View Map

  • 222 SAINT JAMES PARK
  • Price: $847,000
  • Zip Code: 34229
  • 3665 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 3 Baths: 3+
  • **MOVE-IN CONDITION** ENJOY the 3D TOUR and AERIAL VIDEO of this Classic ARTHUR RUTENBERG built, architecturally-inspired, meticulously-maintained, 3 bedroom and 3-1/2 bath gorgeous pool home offering picturesque, golf course views on a quiet, cul de ... Read More
  • Listing courtesy of: GENEROUS PROPERTY

MLS# A4477328 - Status: Active View Property Details Add to Favorites View Map

  • 472 E MACEWEN DR
  • Price: $825,000
  • Zip Code: 34229
  • 3028 Square Feet
  • Subdivision: OAKS 2 PH 4-B
  • Bedrooms: 4 Baths: 3
  • Experience the ultimate in country club living as soon as you pass through the manned security gates of The Oaks. Upon entering this open and inviting home you are immediately drawn to the long views past the pool over the lake to the wide expanse of ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

57 listings found