The Oaks Club

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

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 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

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.

45 listings found

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MLS# A4627698 - Status: Active View Property Details Add to Favorites View Map

• 854 MACEWEN DR
• Price: $4,495,000
• Zip Code: 34229
• 9081 Square Feet
• Subdivision: OAKS 2 PH 2
• Bedrooms: 4 Baths: 4+
• One or more photo(s) has been virtually staged. **NEWLY RENOVATED, SPACIOUS, GOLF COURSE ESTATE** Boasts OVER 9,000sf and is situated on a prominent, private cul de sac lot of Over 3/4 Acres. Expansive room abounds in this LIGHT and BRIGHT Open Floor ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4635707 - Status: Active View Property Details Add to Favorites View Map

• 662 FERNWALK LN
• Price: $3,150,000
• Zip Code: 34229
• 4684 Square Feet
• Subdivision: OAKS
• Bedrooms: 4 Baths: 4
• **FANTASTIC, FULLY RENOVATED ESTATE of Nearly 4700sf with LAKE / GARDEN VIEW is situated on a SERENE, INTERIOR, CUL-DE-SAC lot with NO FLOOD concern (Zone "X") behind the Secure Gates of the highly sought after Bayside neighborhood within The Oaks Co ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4636184 - Status: Active View Property Details Add to Favorites View Map

• 370 SUGAR MILL DR
• Price: $2,650,000
• Zip Code: 34229
• 4783 Square Feet
• Subdivision: OAKS
• Bedrooms: 5 Baths: 5+
• **TIMELESS ELEGANCE! METICULOUSLY MAINTAINED, ARCHITECTURAL GEM FEATURES MANY RECENT UPDATES/UPGRADES** Built by BARON Construction, one of Sarasota's Finest Custom Builders, this Spectacular Estate features 5-BEDS, 5 FULL and 1 HALF BATHS, PLUS expa ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4637260 - Status: Active View Property Details Add to Favorites View Map

• 230 OSPREY POINT DR
• Price: $2,495,000
• Zip Code: 34229
• 3586 Square Feet
• Subdivision: OAKS
• Bedrooms: 3 Baths: 3+
• **IMMACULATE ESTATE -- NEWER CONSTRUCTION (2014) -- METICULOUSLY MAINTAINED, MOVE-IN READY, CUSTOM Residence Designed by LAS CASITAS Architects** offers exceptional quality craftsmanship throughout and is located behind the Secure Gates of THE OAKS-B ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4635026 - Status: Active View Property Details Add to Favorites View Map

• 654 TRENTON WAY
• Price: $2,450,000
• Zip Code: 34229
• 3582 Square Feet
• Subdivision: OAKS 2 PHASE 2
• Bedrooms: 4 Baths: 3+
• **STUNNING, UPDATED and METICULOUSLY MAINTAINED GOLF COURSE ESTATE with INCREDIBLE OUTDOOR OASIS in the Highly Sought-After OAKS COUNTRY CLUB Community** is Situated on an Over Acre Lot on a tranquil, cul de sac street with Ideal Southern-Exposure a ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4629641 - Status: Active View Property Details Add to Favorites View Map

• 703 MACEWEN DR
• Price: $2,350,000
• Zip Code: 34229
• 4641 Square Feet
• Subdivision: OAKS
• Bedrooms: 4 Baths: 3+
• Bathed in natural light, with highly sought after southern lanai exposure, is this stunning and meticulously maintained custom built John Cannon home in The Oaks Clubside. With 4 bedrooms, and 3 full and one half bathrooms, there is room for loved o ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4632694 - Status: Active View Property Details Add to Favorites View Map

• 85 SUGAR MILL DR
• Price: $2,150,000
• Zip Code: 34229
• 4191 Square Feet
• Subdivision: OAKS
• Bedrooms: 3 Baths: 3
• **STUNNINGLY DESIGNED and UPDATED -- ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Little Sarasota Bay waters features 3 BEDS plus DEN/OFFICE, 3 FULL BATHS and incredible detail throughout including beautiful crown m ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4631057 - Status: Active View Property Details Add to Favorites View Map

• 401 WALLS WAY
• Price: $1,825,000
• Zip Code: 34229
• 4388 Square Feet
• Subdivision: OAKS 2 PH 1
• Bedrooms: 4 Baths: 3+
• Recently appraised for over 2 million, Seller relocating. Exquisite Executive Home in The Oaks Clubside, Step into elegance and luxury with this stunning two-story masterpiece. Perfectly situated to capture breathtaking views of the 9th Fairway on t ... Read More
• Listing courtesy of: RE/MAX ALLIANCE GROUP

MLS# A4608902 - Status: Active View Property Details Add to Favorites View Map

• 97 SUGAR MILL DR
• Price: $1,800,000
• Zip Code: 34229
• 4885 Square Feet
• Subdivision: OAKS
• Bedrooms: 5 Baths: 6
• Welcome home to The Oaks Bayside!! This home offers the perfect blend of luxury and comfort. Fall in love with this stately two-story custom pool home. On entry, you are immediately greeted by soaring 24' ceilings, floor to ceiling Palladian windows ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4628121 - Status: Active View Property Details Add to Favorites View Map

• 75 OSPREY POINT DR
• Price: $1,795,000
• Zip Code: 34229
• 4001 Square Feet
• Subdivision: OAKS
• Bedrooms: 4 Baths: 4
• Welcome to 75 Osprey Point, a residence that epitomizes timeless elegance and thoughtful design within the prestigious Oaks Bayside. On two expansive lots totaling over three-quarters of an acre, this architectural estate was originally designed by r ... Read More
• Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4621683 - Status: Active View Property Details Add to Favorites View Map

• 909 MACEWEN DR
• Price: $1,795,000
• Zip Code: 34229
• 4241 Square Feet
• Subdivision: OAKS 2 PHASE 2
• Bedrooms: 3 Baths: 3+
• **STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this s ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4613147 - Status: Active View Property Details Add to Favorites View Map

• 402 WALLS WAY
• Price: $1,795,000
• Zip Code: 34229
• 3464 Square Feet
• Subdivision: OAKS 2 PH 1
• Bedrooms: 4 Baths: 3+
• **NEWER CONSTRUCTION (2014) -- IMPRESSIVE, CUSTOM "COURTYARD STYLE" GOLF COURSE ESTATE w/ WATER VIEW built by TODD JOHNSON HOMES** is situated on an Oversized, 0.64 Acre, LAKESIDE CORNER LOT behind the Secure gates of THE OAKS COUNTRY CLUB Community. ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4637839 - Status: Active View Property Details Add to Favorites View Map

• 282 SHELL MIDDEN CT
• Price: $1,700,000
• Zip Code: 34229
• 3699 Square Feet
• Subdivision: OAKS
• Bedrooms: 4 Baths: 5
• One or more photo(s) has been virtually staged. It is rare to find such an incredible combination of privacy and spectacular views as you will find in this 4 bedroom, 5 bath home. Located on a quiet dead-end street in The Oaks Bayside, the tradition ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4626405 - Status: Active View Property Details Add to Favorites View Map

• 325 OSPREY POINT DR
• Price: $1,649,000
• 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 Mainta ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4617671 - Status: Active View Property Details Add to Favorites View Map

• 360 N POINT RD
• Price: $1,595,000
• Zip Code: 34229
• 2913 Square Feet
• Subdivision: OAKS 3 PH 1
• Bedrooms: 3 Baths: 3+
• **DON'T WAIT TO BUILD!** EXQUISITE, NEWLY-CONSTRUCTED and NEVER LIVED-IN, SPANISH MISSION STYLE home behind the Secure Gates of the COVETED, OAKS PRESERVE Country Club Neighborhood on Sarasota Bay waters offers superb attention to detail. This Custo ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4626382 - Status: Active View Property Details Add to Favorites View Map

• 393 N POINT RD #801
• Price: $1,549,000
• 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# A4584850 - Status: Active View Property Details Add to Favorites View Map

• 401 N POINT RD #901
• Price: $1,549,000
• 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# G5084149 - Status: Active View Property Details Add to Favorites View Map

• 1108 BAYHEAD LN
• Price: $1,500,000
• Zip Code: 34229
• 3541 Square Feet
• Subdivision: BISHOPS COURT AT OAKS PRESERVE
• Bedrooms: 4 Baths: 4
• **Luxurious Turnkey Home in The Oaks, Sarasota** Amazing Sunsets ** Fine accessories & furniture w/leather & textured fabrics **Dream Bathroom and Dressing rooms with Fantastic Built-In's ** Large 2 car garage w/storage ** Solar Heated Salt water po ... Read More
• Listing courtesy of: ILLUSTRATED PROPERTIES LLC (CO

MLS# A4638035 - Status: Active View Property Details Add to Favorites View Map

• 393 N POINT RD #604
• Price: $1,300,000
• Zip Code: 34229
• 2778 Square Feet
• Subdivision: MERIDIAN AT THE OAKS PRESERVE
• Bedrooms: 3 Baths: 3
• Immerse yourself in the unparalleled, unobstructed views of Little Sarasota Bay, the Gulf of Mexico and Midnight Pass, with Casey Key and Siesta Key gracing the horizon from this 6th-Floor Corner Unit Condo. Marvel at the gorgeous water views during ... Read More
• Listing courtesy of: ROBERT SLACK LLC

MLS# A4622032 - Status: Active View Property Details Add to Favorites View Map

• 409 NORTH POINT RD #902
• Price: $1,275,000
• Zip Code: 34229
• 2055 Square Feet
• Subdivision: MERIDIAN AT THE OAKS PRESERVE
• Bedrooms: 3 Baths: 3
• A rare offering, Ninth floor UPDATED Penthouse with private 2 car garage. Enjoy the ultimate unobstructed views of Little Sarasota Bay that includes the Gulf of Mexico & Midnight Pass with Casey Key and Siesta Key in the vista. This upper-level Pen ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4635743 - Status: Active View Property Details Add to Favorites View Map

• 227 SAINT JAMES PARK
• Price: $1,225,000
• Zip Code: 34229
• 2071 Square Feet
• Subdivision: OAKS
• Bedrooms: 2 Baths: 2
• **TURNKEY FURNISHED, ELEGANT and TRADITIONAL ESTATE by Famed Architect, Bo MacEwen, on the Single Largest 0.32 Acre Cul De Sac Lot in the Popular SAINT JAMES PARK neighborhood in The Oaks Country Club. NEW ROOF (2024), HURRICANE IMPACT WINDOWS and S ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4635820 - Status: Active View Property Details Add to Favorites View Map

• 32 BAYHEAD LN
• Price: $1,195,000
• Zip Code: 34229
• 2570 Square Feet
• Subdivision: OAKS
• Bedrooms: 3 Baths: 3+
• Divine is in the details of this lovely 3 bedroom, 3 bath professionally redesigned home in the Oaks Preserve. No need to be concerned with remodeling, as this home underwent a complete renovation in 2023. This exceptional property meets the demands ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4632891 - Status: Active View Property Details Add to Favorites View Map

• 385 N POINT RD #404
• Price: $998,500
• Zip Code: 34229
• 2778 Square Feet
• Subdivision: MERIDIAN AT THE OAKS PRESERVE
• Bedrooms: 4 Baths: 3
• Discover this unique condominium in the Oaks Preserve overlooking Little Sarasota Bay, Gulf of Mexico sunsets, the Intracoastal Waterway, and the opportunity to awaken to panoramic views of undisturbed landscape. Enter your private foyer and enjoy ch ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4611618 - Status: Active View Property Details Add to Favorites View Map

• 409 N POINT RD #501
• Price: $995,000
• Zip Code: 34229
• 2594 Square Feet
• Subdivision: MERIDIAN AT THE OAKS PRESERVE
• Bedrooms: 3 Baths: 3
• One or more photo(s) has been virtually staged. Welcome to luxury condo living in The Oaks Preserve. This 3 bedroom, 3 bath corner unit with office, offers everything you need to live the country club lifestyle with comfort and ease. Take your priva ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4627082 - Status: Active View Property Details Add to Favorites View Map

• 21 BAYHEAD LN
• Price: $959,000
• Zip Code: 34229
• 2216 Square Feet
• Subdivision: OAKS
• Bedrooms: 3 Baths: 2
• This incredible newly updated house with many upgrades and amenities is the home you have been waiting for! Ideally located in the beautiful Oaks Preserve between Siesta Key and Casey Key, the private enclave is in a shaded neighborhood where reside ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

45 listings found

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