The Oaks Club

Listings For SaleSold History and Market Report

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.

46 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# A4482771 - Status: Active View Property Details Add to Favorites View Map

  • 95 OSPREY POINT DR
  • Price: $2,450,000
  • Zip Code: 34229
  • 7231 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 5+
  • Presenting a rare opportunity for the discerning buyer to own two waterfront homes on one private estate in the luxurious Oaks Bayside spanning well over 7,000 SqFt on a double lot. Architectural masterpieces, both tucked away in a storybook setting, ... 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: $1,798,000
  • Zip Code: 34229
  • 6981 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 5+
  • Located on a private street with a 24-7 guard gate entrance in Sarasota's iconic community, custom built in 2008 by John Cannon, it is the NEWEST home available for sale in The Oaks Club. This five bedroom property features a spacious pool area with ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4483236 - Status: Active View Property Details Add to Favorites View Map

  • 548 EAGLE WATCH LN
  • Price: $1,400,000
  • Zip Code: 34229
  • 4681 Square Feet
  • Subdivision: OAKS 2 PH 2
  • Bedrooms: 4 Baths: 3+
  • From the moment you see this 4 bedroom, 3.5 bath home you will be enchanted. Custom-built by Baron Construction, it is situated on a large lot that is just over three quarters of an acre. On a corner of a cul-de-sac, it is ideally positioned to provi ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# D6114951 - 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+
  • Executive home located in the premier Oaks Club in Osprey awaits a buyer that needs room for everyone. Home has 6 bedrooms with 5 baths, custom kitchen, separate dining room, kitchen family room combination, living room with architectural elements & ... Read More
  • Listing courtesy of: PARADISE EXCLUSIVE INC

MLS# A4483742 - Status: Active View Property Details Add to Favorites View Map

  • 658 FERNWALK LN
  • Price: $1,349,000
  • Zip Code: 34229
  • 3612 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 3+
  • This distinguished residence is sited at the end of a cul-de-sac in the Oaks. From the moment you step through the double doors youwill be taken in by the warm of this home. The open floor plan, high ceilings make the interior light and bright, creat ... Read More
  • Listing courtesy of: BETTER HOMES & GARDENS REAL ESTATE ATCHLEY PROPERT

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

  • 676 EAGLE WATCH LN
  • Price: $1,329,000
  • 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 short term owner financing. This custom built 5400sf single story has been extensively renovated to include fresh interior paint throughout, new high-end hardwood f ... Read More
  • Listing courtesy of: CHARLES RUTENBERG REALTY INC

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

  • 398 MACEWEN DR
  • Price: $1,060,000
  • Zip Code: 34229
  • 4743 Square Feet
  • Subdivision: OAKS 2 PH 3
  • Bedrooms: 4 Baths: 5+
  • One or more photo(s) has been virtually staged. 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 ... 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# A4483385 - Status: Active View Property Details Add to Favorites View Map

  • 393 N POINT RD #801
  • Price: $1,025,000
  • 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# A4482204 - Status: Active View Property Details Add to Favorites View Map

  • 644 TARLETON LN
  • Price: $935,000
  • Zip Code: 34229
  • 3744 Square Feet
  • Subdivision: OAKS 2 PH 2
  • Bedrooms: 3 Baths: 3+
  • ENJOY the 3D VIRTUAL TOUR of this elegant and timeless, 3 Bed / 3.5 Bath, Luxury Estate situated on the Heron Golf Course. Relish in the coveted lifestyle of The Oaks Club, featuring Luxury Coastal Living in the Heart of Sarasota County. This proper ... Read More
  • Listing courtesy of: GENEROUS PROPERTY

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. **PLENTY OF ROOM to build the POOL OF YOUR ... Read More
  • Listing courtesy of: GENEROUS PROPERTY

MLS# A4481376 - Status: Active View Property Details Add to Favorites View Map

  • 140 SUGAR MILL DR
  • Price: $800,000
  • Zip Code: 34229
  • 3286 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 4
  • Beautiful custom designed and built 4 bedroom, 4 bath home in The Oaks Bayside with light-filled contemporary space and elegant classic details; crown moldings, high ceilings and mahogany wood floors. Dramatic cathedral ceilings in the family room an ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4474001 - Status: Active View Property Details Add to Favorites View Map

  • 3603 N POINT RD #602
  • Price: $699,000
  • Zip Code: 34229
  • 2545 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3
  • Unending views of Little Sarasota Bay, Casey Key, and the Gulf of Mexico set the stage for unmatched elegance in this sophisticated residence within The Oaks Country Club. Perched on the sixth floor of the newest Meridian tower, gracious spaces for e ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4475783 - Status: Active View Property Details Add to Favorites View Map

  • 63 SUGAR MILL DR #Dr
  • Price: $675,000
  • Zip Code: 34229
  • 3125 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 3 Baths: 3
  • Seller Credit towards membership of choice with an acceptable offer! Start living your best life in your Oaks Bay Side home! Available for immediate occupancy and offers a beautiful, private master suite, spacious chefs kitchen with adjoining family ... Read More
  • Listing courtesy of: HUNT BROTHERS REALTY, INC.

MLS# A4484546 - Status: Active View Property Details Add to Favorites View Map

  • 12 BISHOPS COURT RD
  • Price: $634,900
  • Zip Code: 34229
  • 3182 Square Feet
  • Subdivision: BISHOPS COURT AT OAKS PRESERVE
  • Bedrooms: 3 Baths: 3+
  • Beautiful Home in the Oaks Preserve Country Club Community! As you enter, you are greeted with a gorgeous private courtyard pool/hot tub area with a Casita (BR/BA) for guests. Then, continuing on your path into the home, through a bank of glass F ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4483908 - Status: Active View Property Details Add to Favorites View Map

  • 401 N POINT RD #304
  • Price: $625,000
  • Zip Code: 34229
  • 2778 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3
  • Give yourself the gift of luxury living! This 2,778 square foot residence is the largest non-penthouse floor plan available in Meridian at The Oaks Preserve. With three bedroom, plus a dining room and an office/den, this unit offers all the space yo ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4456917 - Status: Active View Property Details Add to Favorites View Map

  • 3603 N POINT RD #302
  • Price: $599,000
  • Zip Code: 34229
  • 2545 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3
  • Value Opportunity! Great new price! What makes THIS residence special? It's location in Tower VI the newest building, completed in 2007 & placed on the Southwestern-most spot available on the Preserve at the end of North Point Road for a very quiet ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# N6109590 - Status: Active View Property Details Add to Favorites View Map

  • 73 SUGAR MILL DR
  • Price: $585,000
  • Zip Code: 34229
  • 3861 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 3 Baths: 2+
  • Peace and serenity abound as you drive amongst the canopied and winding streets of the Oaks, Bayside. As you enter through the double solid mahogany doors you will notice the quality craftsmanship and superior finishes throughout. Gorgeous wood floor ... Read More
  • Listing courtesy of: EXIT KING REALTY

MLS# A4459800 - Status: Active View Property Details Add to Favorites View Map

  • 219 SAINT JAMES PARK
  • Price: $500,000
  • Zip Code: 34229
  • 3300 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 3 Baths: 3+
  • RECENTLY REDUCED by motivated seller, the only thing this house needs is you to come and make it your own! What would make your dreams come true? How about your own little dose of the sweet south, in one of the finest golf and country club communitie ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4413096 View Property Details Add to Favorites View Map

  • 132 OSPREY POINT DR
  • Price: $500,000
  • Zip Code: 34229
  • 0 Acres
  • Build your dream home behind the gates of The Oaks Bayside. The lot has been cleared and is ready to build on. Adjoining lot is also available, allowing you to create a 1.5 acre estate. Lots are offered at $500,000 individually or $950,000 if purchas ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4413092 View Property Details Add to Favorites View Map

  • 128 OSPREY POINT DR
  • Price: $500,000
  • Zip Code: 34229
  • 0 Acres
  • Build your dream home behind the gates of The Oaks Bayside. The lot has been cleared and is ready to build on. Adjoining lot is also available, allowing you to create a 1.5 acre estate. Lots are offered at $500,000 individually or $950,000 if purchas ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

46 listings found