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.

42 listings found

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MLS# A4639897 - Status: Active View Property Details Add to Favorites View Map

• 101 OSPREY POINT DR
• Price: $5,300,000
• Zip Code: 34229
• 5087 Square Feet
• Subdivision: THE OAKS
• Bedrooms: 4 Baths: 5+
• One or more photo(s) has been virtually staged. Indulge in the epitome of sophistication and timeless elegance with this magnificent luxury home with 4 bedrooms, 5 full and 1 half bath. Meticulously crafted with unparalleled attention to detail by Bo ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

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

• 854 MACEWEN DR
• Price: $4,195,000
• Zip Code: 34229
• 9081 Square Feet
• Subdivision: OAKS 2 PH 2
• Bedrooms: 4 Baths: 4+
• One or more photo(s) has been virtually staged. **SELLER WILL PAY 100% OF THE MANDATORY SOCIAL MEMBERSHIP - WORTH $80,000 - IF CLOSING BY JUNE 2ND, 2025** NEWLY RENOVATED, SPACIOUS, GOLF COURSE ESTATE Boasts OVER 9,000sf and is situated on a prominen ... Read More
• Listing courtesy of: GENEROUS PROPERTY

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

• 662 FERNWALK LN
• Price: $2,995,000
• Zip Code: 34229
• 4359 Square Feet
• Subdivision: OAKS
• Bedrooms: 4 Baths: 4
• **FANTASTIC, FULLY RENOVATED ESTATE 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 Country Club commun ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4644125 - Status: Active View Property Details Add to Favorites View Map

• 236 SAINT JAMES PARK
• Price: $2,900,000
• Zip Code: 34229
• 6246 Square Feet
• Subdivision: OAKS 2 PH 1
• Bedrooms: 6 Baths: 6+
• Tucked away in a quiet cul-de-sac on a double lot beneath majestic oaks, this almost 5,000 sq ft, timeless 2-story home blends sophistication with modern comfort. Situated on the first hole of Heron Golf Course, the home features soaring 11-ft ceilin ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4642364 - Status: Active View Property Details Add to Favorites View Map

• 49 OSPREY POINT DR
• Price: $2,795,000
• Zip Code: 34229
• 3953 Square Feet
• Subdivision: OAKS
• Bedrooms: 4 Baths: 3+
• Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almo ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4647690 - Status: Active View Property Details Add to Favorites View Map

• 340 OSPREY POINT DR
• Price: $2,500,000
• Zip Code: 34229
• 6001 Square Feet
• Subdivision: OAKS
• Bedrooms: 5 Baths: 5+
• Introducing The Grand Estate at The Oaks Bayside--a true masterpiece of refined living within one of Sarasota's most prestigious gated communities. Surrounded by majestic oak trees and lush tropical landscaping, this extraordinary residence offers th ... Read More
• Listing courtesy of: RE/MAX ALLIANCE GROUP

MLS# A4647789 - Status: Active View Property Details Add to Favorites View Map

• 600 EAGLE WATCH LN
• Price: $2,395,000
• Zip Code: 34229
• 3681 Square Feet
• Subdivision: OAKS 2 PH 2
• Bedrooms: 3 Baths: 3
• Located on one of the most desirable streets in The Oaks Clubside, this completely renovated pool home sits on a generous 0.71-acre lot with wide views of the third hole of the Heron Golf Course. Nearly every aspect of the property has been updated-- ... 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# A4639504 - Status: Active View Property Details Add to Favorites View Map

• 67 SUGAR MILL DR
• Price: $1,995,000
• Zip Code: 34229
• 4020 Square Feet
• Subdivision: OAKS
• Bedrooms: 4 Baths: 3+
• Bring your clubs and come see this beautifully remodeled home in the Oaks Club (Bayside). Move in ready with all the amenities you need. This home boast all the room you need with 4 bedroom and a study/Bourbon room. Totally secluded back yard for enj ... Read More
• Listing courtesy of: MAPP REALTY & INVESTMENT CO

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# 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# 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: 3 Baths: 4+
• 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 3 bedroom, 4.5 bath home. Located on a quiet dead-end street in The Oaks Bayside, the traditi ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4644989 - Status: Active View Property Details Add to Favorites View Map

• 402 WALLS WAY
• Price: $1,695,000
• Zip Code: 34229
• 3464 Square Feet
• Subdivision: OAKS 2 PH 1
• Bedrooms: 4 Baths: 3+
• This captivating 4 bedroom (plus den/office), 3.5 bathroom home is ready to welcome you into its charm and warmth. Built in 2014 by Todd Johnson Homes, this courtyard-style residence effortlessly blends country modern flair with timeless elegance. Si ... 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: $1,649,000
• 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# A4641594 - Status: Active View Property Details Add to Favorites View Map

• 20 BAYHEAD LN
• Price: $1,625,000
• Zip Code: 34229
• 3486 Square Feet
• Subdivision: OAKS
• Bedrooms: 4 Baths: 3
• Discover the perfect blend of luxury and tranquility in this stunning 2017 custom home built by owner, nestled on an oversized 17,512 sq. ft. lakefront lot in the exclusive gated Oaks Preserve community. Boasting breathtaking water views and total ba ... Read More
• Listing courtesy of: SARASOTA LAND AND HOMES LLC

MLS# A4648895 - Status: Active View Property Details Add to Favorites View Map

• 228 SAINT JAMES PARK
• Price: $1,595,000
• Zip Code: 34229
• 2425 Square Feet
• Subdivision: OAKS 2 PH 1
• Bedrooms: 3 Baths: 2+
• Experience the unparalleled charm and convenience of this golf course home in The Oaks Club, the country club community designed by noted Sarasota architect Bo MacEwen. 228 Saint James Park is an original Bo MacEwen design, is located on the leafy an ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

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# A4642397 - Status: Active View Property Details Add to Favorites View Map

• 3603 N POINT RD #702
• Price: $1,395,000
• Zip Code: 34229
• 2545 Square Feet
• Subdivision: MERIDIAN AT THE OAKS PRESERVE
• Bedrooms: 3 Baths: 3
• **MAGNIFICENT VIEW from this 7th FLOOR, PENTHOUSE CONDO** Offering 3 EN SUITE BEDROOMS, 3 FULL BATHS and a treasured PRIVATE 2-CAR GARAGE! Located behind the gates of the highly sought after Oaks-Preserve, country club neighborhood in the Newest Meri ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4647780 - Status: Active View Property Details Add to Favorites View Map

• 3621 NORTH POINT RD #603
• Price: $1,350,000
• Zip Code: 34229
• 2680 Square Feet
• Subdivision: MERIDIAN AT THE OAKS PRESERVE
• Bedrooms: 3 Baths: 3
• Prepare to be captivated by this COMPLETELY UPDATED, meticulously maintained, and thoughtfully appointed 3 bedroom, 3 bath condo located in Meridian at The Oaks Preserve. This spacious residence has everything you need to embrace a carefree, luxury l ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

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# A4648471 - Status: Active View Property Details Add to Favorites View Map

• 223 SAINT JAMES PARK
• Price: $1,299,000
• Zip Code: 34229
• 3321 Square Feet
• Subdivision: OAKS 2 PH 1
• Bedrooms: 3 Baths: 3+
• Luxury Clubside Living at The Oaks - featuring Elegance and Comfort! Stunning Clubside residence in the upscale Oaks Club, offering the perfect blend of estate charm and modern luxury. Nestled among grand oak trees with partial lake and full golf co ... Read More
• Listing courtesy of: RE/MAX ALLIANCE GROUP

MLS# A4649389 - Status: Active View Property Details Add to Favorites View Map

• 385 N POINT RD #903
• Price: $1,295,000
• Zip Code: 34229
• 2778 Square Feet
• Subdivision: MERIDIAN AT THE OAKS PRESERVE
• Bedrooms: 3 Baths: 3
• From the moment the private elevator doors open, the panorama of the view has you at 'hello," with a northwest-facing expanse over the preserve, the lagoon below, Sarasota Bay and the Gulf beyond. This orientation brings cooler interiors, dramatic na ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

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

• 227 SAINT JAMES PARK
• Price: $1,045,000
• 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

42 listings found

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