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.

32 listings found

MLS# A4600730 - Status: Active View Property Details Add to Favorites View Map

  • 601 FERNWALK LN
  • Price: $3,995,000
  • Zip Code: 34229
  • 5453 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 5+
  • **EXQUISITELY DESIGNED ESTATE BOASTS MODERN & CONTEMPORARY ELEGANCE** This FULLY UPDATED Residence features a MAIN HOUSE with 3Beds/4.5Baths plus GUEST HOUSE (1Bed/1Bath, Kitchen/Laundry, Living area) and is situated on an Oversized, Private and Sere ... Read More
  • Listing courtesy of: GENEROUS PROPERTY

MLS# A4603537 - Status: Active View Property Details Add to Favorites View Map

  • 497 WEBBS CV
  • Price: $3,600,000
  • Zip Code: 34229
  • 6863 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 6+
  • MAGNIFICENT UPDATED ESTATE! Located in the highly sought after Oaks Country Club! As you enter the Double Doors you will be Amazed at this Master-Piece that words alone can not describe This 5-Bedroom 6.5 Bath with 6-car Garage residence. Also includ ... Read More
  • Listing courtesy of: BERKSHIRE HATHAWAY HOMESERVICE

MLS# A4601108 - Status: Active View Property Details Add to Favorites View Map

  • 101 SUGAR MILL DR
  • Price: $3,200,000
  • Zip Code: 34229
  • 3875 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 3 Baths: 3
  • New. Notable. No Waiting for your Dream Home! Rare opportunity for a luxury Florida lifestyle with this just completed John Cannon custom build. A coveted West of Trail location in The Oaks Bayside positions you in one of the area's only country cl ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4603094 - Status: Active View Property Details Add to Favorites View Map

  • 165 SUGAR MILL DR
  • Price: $1,995,000
  • Zip Code: 34229
  • 3912 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 4+
  • This 4 bedroom, 4.5 bath home in The Oaks Bayside has been continuously updated and redecorated over the past several years, making it a pristine, elegant showcase. This is the perfect home for the refined country club lifestyle you seek to live. As ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4584850 - Status: Active View Property Details Add to Favorites View Map

  • 401 N POINT RD #901
  • Price: $1,750,000
  • Zip Code: 34229
  • 2594 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3
  • This opulent 3 bedroom plus den, 3 bath residence with a PRIVATE 2 CAR GARAGE located in Meridian at The Oaks Preserve, is a dream come true! A penthouse-level end unit situated on the north side of the building, it has been carefully updated and met ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4584509 - Status: Active View Property Details Add to Favorites View Map

  • 452 BLUE GARDEN LN
  • Price: $1,750,000
  • Zip Code: 34229
  • 3910 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 3 Baths: 3+
  • PRIVACY ABOUNDS IN THIS COMPLETELY UPDATED HOME W/NEWER ROOF located behind the gates of The Oaks Bayside. This custom-built 3 bedroom, 3.5 bath home with enormous office/den is the personification of a Sarasota dream come true! And it is move in re ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4601618 - Status: Active View Property Details Add to Favorites View Map

  • 325 OSPREY POINT DR
  • Price: $1,689,900
  • Zip Code: 34229
  • 3905 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 3 Baths: 4+
  • **BEAUTIFULLY UPDATED ESTATE with WATER VIEW and STUNNING ARCHITECTURAL DETAILS** is located in the COVETED, OAKS BAYSIDE Country Club Neighborhood on Little Sarasota Bay. Enjoy the Private and Tranquil, Lake-front setting of this Meticulously Maint ... Read More
  • Listing courtesy of: GENEROUS PROPERTY

MLS# A4594469 - Status: Active View Property Details Add to Favorites View Map

  • 360 N POINT RD
  • Price: $1,645,000
  • Zip Code: 34229
  • 2913 Square Feet
  • Subdivision: OAKS 3 PH 1
  • Bedrooms: 3 Baths: 3+
  • One or more photo(s) has been virtually staged. Discover the quality and convenience of a home that blends classic allure with modern comfort, providing the perfect canvas for your luxury lifestyle in this brand-new, never-lived-in masterpiece on a r ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4570326 - Status: Active View Property Details Add to Favorites View Map

  • 67 SUGAR MILL DR
  • Price: $1,625,000
  • Zip Code: 34229
  • 4020 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 3+
  • **ELEGANT, TRADITIONAL, CUSTOM-BUILT ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood on Sarasota Bay Waters is sure to impress, boasting MANY UPDATES and Remarkable Architectural Detail throughout and consists of 4 Beds + 3 Full Baths + ... Read More
  • Listing courtesy of: GENEROUS PROPERTY

MLS# A4593090 - Status: Active View Property Details Add to Favorites View Map

  • 607 N MACEWEN DR
  • Price: $1,595,000
  • Zip Code: 34229
  • 3574 Square Feet
  • Subdivision: OAKS 2 PH 4-C PT 3
  • Bedrooms: 4 Baths: 4
  • **YOU CAN CHANGE ANYTHING IN A HOUSE, BUT YOU CANNOT CHANGE THE VIEW.** This Golf Course Estate has a very private backyard with a wide and long extended golf course and water view! Ideally situated on the interior, Heron Golf Course and with South- ... Read More
  • Listing courtesy of: GENEROUS PROPERTY

MLS# A4597633 - Status: Active View Property Details Add to Favorites View Map

  • 401 N POINT RD #701
  • Price: $1,400,000
  • Zip Code: 34229
  • 2594 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3
  • Enjoy luxury living at its finest in this TOTALLY RENOVATED 3 bedroom, 3 bath residence with a PRIVATE ONE CAR GARAGE plus one parking space under the building. Located in Meridian, behind the secure gates of The Oaks Preserve, you truly feel like y ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4601227 - Status: Active View Property Details Add to Favorites View Map

  • 84 BISHOPS COURT RD
  • Price: $1,295,000
  • Zip Code: 34229
  • 2573 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 3 Baths: 3
  • Splendid is in the details of this lovely three bedroom, three bath, move in ready home in The Oaks Preserve. No need to be concerned with remodeling, as this wonderful home underwent a total and complete interior and exterior renovation in 2023. Thi ... Read More
  • Listing courtesy of: COLDWELL BANKER SARASOTA CENT.

MLS# A4596761 - Status: Active View Property Details Add to Favorites View Map

  • 401 N POINT RD #903
  • Price: $1,250,000
  • Zip Code: 34229
  • 2203 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3
  • BEAUTIFULLY UPDATED 3 bedroom, 3 bath 9th floor penthouse with PRIVATE 2 CAR GARAGE in Meridian at The Oaks Preserve offers the perfect living space for those who seek luxury and comfort in a country club community. RECENTLY RENOVATED and meticulousl ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4593249 - Status: Active View Property Details Add to Favorites View Map

  • 409 N POINT RD #702
  • Price: $1,200,000
  • Zip Code: 34229
  • 2055 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3
  • One or more photo(s) has been virtually staged. Sweeping views of the Intracoastal and Gulf welcome you as you enter this impeccably kept seventh floor Meridian unit with its own private entrance. Pride of ownership is evident at every turn. Beautifu ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4600762 - Status: Active View Property Details Add to Favorites View Map

  • 385 N POINT RD #404
  • Price: $1,150,000
  • Zip Code: 34229
  • 2778 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 4 Baths: 3
  • 4th floor residence offers an uncommon feature, water views of THREE waterways, North Creek, the Intracoastal and the Gulf! And, unlike some units at this level, you won't have to play peek-a-boo to take in the spectacular views of water, surroundin ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4600972 - Status: Active View Property Details Add to Favorites View Map

  • 201 SAINT JAMES PARK
  • Price: $1,095,000
  • Zip Code: 34229
  • 2855 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 3 Baths: 3
  • Welcome home to your sanctuary located behind the gates of the Exclusive Oaks Country Club. This corner lot in SAINT JAMES PARK is situated close to the CLUB, TENNIS, and all the amenities the community has to offer. As you approach the home the lush ... Read More
  • Listing courtesy of: ROSEBAY INTERNATIONAL REALTY INC

MLS# A4604256 - Status: Active View Property Details Add to Favorites View Map

  • 12 BISHOPS COURT RD RD
  • Price: $995,000
  • Zip Code: 34229
  • 3182 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 3 Baths: 3+
  • Welcome to the Oaks Preserve, a wonderful neighborhood of natural beauty and lush canopied surroundings, yet close to Sarasota's #1 beaches and the ideal location for easy living! This gracious and charming courtyard home with a separate guest/casita ... Read More
  • Listing courtesy of: COLDWELL BANKER SARASOTA CENT.

MLS# A4600038 View Property Details Add to Favorites View Map

  • N POINT RD
  • Price: $980,000
  • Zip Code: 34229
  • 3.13 Acres
  • The Oaks Preserve - Located behind the gates of the Oaks Club, the best priced and largest development site of this stunning community. Build your dream custom home on this stunning 3.12 acres lot or build a couple homes and enjoy the privacy and con ... Read More
  • Listing courtesy of: CUADRA GROUP LLC

MLS# A4570004 - Status: Active View Property Details Add to Favorites View Map

  • 401 N POINT RD #603
  • Price: $950,000
  • Zip Code: 34229
  • 2203 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3
  • One or more photo(s) has been virtually staged. BEAUTIFUL FULL WATER VIEW AND 2ND FLOOR PRIVATE 2 CAR GARAGE! This incredible offering has everything you need to live a luxury condominium lifestyle in comfort and ease; 3 bedrooms, 3 full baths and a ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4595119 - Status: Active View Property Details Add to Favorites View Map

  • 393 N POINT RD #602
  • Price: $899,000
  • Zip Code: 34229
  • 2055 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3
  • Experience the sought-after lifestyle of The Oaks Club, seamlessly blended with the convenience and perks of a maintenance-free condominium, in this remarkable residence at The Meridian. This fully renovated three-bedroom, three-bath condominium is a ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# N6126537 View Property Details Add to Favorites View Map

  • 148 OSPREY POINT DR
  • Price: $890,000
  • Zip Code: 34229
  • 0.74 Acres
  • Dreaming of building a new home? Now is the time to purchase the last remaining lot behind the gates of the Oaks Bayside. The Oaks Bayside is on the west side of Tamiami Trail and is surrounded on three sides by water. Residents have use of the commu ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4587942 View Property Details Add to Favorites View Map

  • 147 OSPREY POINT DR
  • Price: $850,000
  • Zip Code: 34229
  • 0.47 Acres
  • Your dream homesite awaits! This lot is located within the Oaks Bayside, one of Southwest Florida's most exclusive private, gated communities. This amazing property is near the community dock and fountain and is surrounded by some of the most grand a ... Read More
  • Listing courtesy of: BRIGHT REALTY

MLS# A4575407 - Status: Active View Property Details Add to Favorites View Map

  • 3603 N POINT RD #202
  • Price: $839,000
  • Zip Code: 34229
  • 3147 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3
  • **ELEGANT and SPACIOUS CORNER CONDO UNIT - NEARLY 3200sf - With MULTIPLE BALCONIES** found behind the gates of the highly sought after Oaks-Preserve neighborhood. This Light and Bright Open Floorplan offers 3 En Suite Bedrooms, 3 Baths, 2 assigned P ... Read More
  • Listing courtesy of: GENEROUS PROPERTY

MLS# A4589564 - Status: Active View Property Details Add to Favorites View Map

  • 393 N POINT RD #503
  • Price: $798,000
  • Zip Code: 34229
  • 2203 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3
  • This condo in Meridian at The Oaks Preserve is an excellent choice! Enter through the secure foyer and take the private elevator to the fifth floor where you will find this charming 3 bedroom, 3 bath residence with dining room and two under the build ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4601891 - Status: Active View Property Details Add to Favorites View Map

  • 409 N POINT RD #603
  • Price: $785,000
  • Zip Code: 34229
  • 2203 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3
  • BEAUTIFUL FULL WATER VIEWS OF NORTH CREEK, SARASOTA BAY, AND THE GULF FROM THE LOWEST PRICED CONDO WITH A WATER VIEW IN THE MERIDIAN. Watch the eagles and osprey fish and enjoy truly stunning sunsets from the balcony of this condo with 3 bedrooms, 3 ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

32 listings found