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# A4664424 - Status: Active View Property Details Add to Favorites View Map

• 101 OSPREY POINT DR
• Price: $5,000,000
• Zip Code: 34229
• 5087 Square Feet
• Subdivision: THE OAKS
• Bedrooms: 4 Baths: 5+
• A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within the private gates of The Oaks Bayside. Designed by architect Bo MacEwen, this one-of-a-kind home spans more than 5,000 square feet, ... Read More
• Listing courtesy of: DOUGLAS ELLIMAN

MLS# A4668477 - Status: Active View Property Details Add to Favorites View Map

• 691 EAGLE WATCH LN
• Price: $3,995,000
• Zip Code: 34229
• 6705 Square Feet
• Subdivision: OAKS 2 PH 2
• Bedrooms: 4 Baths: 5+
• Nestled within the exclusive gated community of the Oaks Club in Osprey, Florida. This singular estate represents a masterful confluence of architectural refinement and modern luxury, encompassing nearly 7000 ft. of conditioned living space, the resi ... Read More
• Listing courtesy of: SARASOTA TRUST REALTY COMPANY

MLS# A4668918 - Status: Active View Property Details Add to Favorites View Map

• 854 MACEWEN DR
• Price: $3,950,000
• Zip Code: 34229
• 9081 Square Feet
• Subdivision: OAKS 2 PH 2
• Bedrooms: 4 Baths: 4+
• One or more photo(s) has been virtually staged. Set on a private cul-de-sac within The Oaks, this revitalized estate captures the essence of elegant Florida living. From the moment you enter, the home's light-filled, open design and thoughtful update ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

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

• 236 SAINT JAMES PARK
• Price: $2,700,000
• 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 sprawling double lot beneath majestic oaks, this nearly 5,000 sq ft timeless 2-story residence blends classic elegance with modern luxury. Perfectly positioned on the first hole of one of Sarasota's most sought- ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4671762 - Status: Active View Property Details Add to Favorites View Map

• 49 OSPREY POINT DR
• Price: $2,595,000
• 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# A4659276 - Status: Active View Property Details Add to Favorites View Map

• 852 MACEWEN DR
• Price: $2,495,000
• Zip Code: 34229
• 4519 Square Feet
• Subdivision: OAKS 2 PH 2
• Bedrooms: 3 Baths: 3+
• **CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4667964 - Status: Active View Property Details Add to Favorites View Map

• 393 N POINT RD #1002
• Price: $2,350,000
• Zip Code: 34229
• 3738 Square Feet
• Subdivision: MERIDIAN AT THE OAKS
• Bedrooms: 3 Baths: 2+
• Experience Unmatched Luxury in this Meridian Penthouse! Welcome to the epitome of luxury living at Meridian at The Oaks Preserve. This stunning 3 bedroom, 2.5 bath penthouse offers a private 2-car garage and is designed for the discerning buyer who v ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4676505 - Status: Active View Property Details Add to Favorites View Map

• 433 E MACEWEN DR
• Price: $2,250,000
• Zip Code: 34229
• 4012 Square Feet
• Subdivision: OAKS
• Bedrooms: 4 Baths: 3+
• An exceptionally well maintained 4,012sf residence with 4 bedrooms 3 full and a half baths situated on the interior Heron golf course on a 0.61 acre lot in the private Oaks Club community. It has golf course and water views and 24 hr gated security. ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4676567 - Status: Active View Property Details Add to Favorites View Map

• 362 MACEWEN DR
• Price: $2,249,000
• Zip Code: 34229
• 4117 Square Feet
• Subdivision: OAKS 2 PH 1
• Bedrooms: 4 Baths: 3+
• Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4668497 - Status: Active View Property Details Add to Favorites View Map

• 600 EAGLE WATCH LN
• Price: $2,195,000
• Zip Code: 34229
• 3681 Square Feet
• Subdivision: OAKS 2 PH 2
• Bedrooms: 3 Baths: 3
• One or more photo(s) has been virtually staged. **BRILLIANTLY UPDATED, MOVE-IN READY, GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** offers an Ideal Southern-Exposure and View across the 3rd Fairway of the Interior, HERON ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4667740 - 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# A4669491 - Status: Active View Property Details Add to Favorites View Map

• 538 DOVE POINTE DR
• Price: $2,100,000
• Zip Code: 34229
• 4346 Square Feet
• Subdivision: OAKS 2 PH 4-C PT 3
• Bedrooms: 4 Baths: 5+
• **ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous .83-acre elevated lot, ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4655736 - Status: Active View Property Details Add to Favorites View Map

• 140 SUGAR MILL DR
• Price: $1,970,000
• Zip Code: 34229
• 3286 Square Feet
• Subdivision: OAKS
• Bedrooms: 4 Baths: 4
• **BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE RESIDENCE with Lush Garden Landscape** is located behind the Secure Gates of The Oaks Bayside, Country Club neighborhood. Featuring 4 BEDROOMS (2 En Suite) and 4 FULL BATHS, this Open Floorp ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4672439 - Status: Active View Property Details Add to Favorites View Map

• 75 OSPREY POINT DR
• Price: $1,775,000
• Zip Code: 34229
• 4001 Square Feet
• Subdivision: OAKS
• Bedrooms: 4 Baths: 4
• **STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Sarasota Bay waters... situated on TWO LOTS totaling over 3/4 acres, the Main House on Lot #1 features 3 Beds / 3 Baths while the separate Guest House on adjac ... Read More
• Listing courtesy of: GENEROUS PROPERTY

MLS# A4678423 - Status: Active View Property Details Add to Favorites View Map

• 25 SUGAR MILL DR
• Price: $1,695,000
• Zip Code: 34229
• 3066 Square Feet
• Subdivision: OAKS
• Bedrooms: 3 Baths: 3+
• METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESERVE VIEWS. Located in Flood Zone "X" (no flood insurance required), the home is tucked behind the secure ... Read More
• Listing courtesy of: GENEROUS PROPERTY

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

• 909 MACEWEN DR
• Price: $1,695,000
• 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# A4672843 - Status: Active View Property Details Add to Favorites View Map

• 76 OSPREY POINT DR
• Price: $1,690,000
• Zip Code: 34229
• 4364 Square Feet
• Subdivision: THE OAKS BAYSIDE
• Bedrooms: 3 Baths: 4+
• COMPLETELY UPGRADED IS NOT AN EXAGGERATION! This Bo MacEwen-designed 3-bedroom, 4.5-bath home has been updated from top (RE-TILED ROOF) to bottom, with new luxury flooring surfaces throughout and over $650,000 in renovations. No expense was spared in ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4674649 - Status: Active View Property Details Add to Favorites View Map

• 20 BAYHEAD LN
• Price: $1,575,000
• Zip Code: 34229
• 3486 Square Feet
• Subdivision: BISHOPS COURT AT THE OAKS PRESERVE
• Bedrooms: 4 Baths: 3
• A rare opportunity to own a significantly newer, custom-built residence inside the exclusive The Oaks Club Preserve, where most surrounding homes were built decades earlier. Completed in 2017 and set on a lakefront lot in a non-flood zone, this move- ... Read More
• Listing courtesy of: EXP REALTY LLC

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

• 360 N POINT RD
• Price: $1,570,000
• 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# A4671431 - Status: Active View Property Details Add to Favorites View Map

• 385 N POINT RD #704
• Price: $1,500,000
• Zip Code: 34229
• 2778 Square Feet
• Subdivision: MERIDIAN AT THE OAKS PRESERVE
• Bedrooms: 3 Baths: 3
• Experience breathtaking views of the Bay and Gulf from this spacious 3 bedroom, 3 bath end unit, featuring a separate dining room and den. Completely updated and meticulously maintained, this unit is beautifully appointed and custom features abound. ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4669444 - Status: Active View Property Details Add to Favorites View Map

• 137 OSPREY POINT DR
• Price: $1,425,000
• Zip Code: 34229
• 3303 Square Feet
• Subdivision: THE OAKS BAYSIDE
• Bedrooms: 4 Baths: 3
• Although built in the 20th century, this home looks as authentic as the French manor house it was modeled after. The faade features a soft, light-colored stucco exterior accented by rustic stonework, creating a warm and inviting presence. Gracefully ... 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# A4664295 - Status: Active View Property Details Add to Favorites View Map

• 133 OSPREY POINT DR
• Price: $1,350,000
• Zip Code: 34229
• 3679 Square Feet
• Subdivision: OAKS
• Bedrooms: 4 Baths: 3
• One or more photo(s) has been virtually staged. Custom Home located in the exclusive gated community of The Oaks Bayside with a private pool and spa. Just across the street from Sarasota Bay. Recent improvements include updated bathrooms and a newer ... Read More
• Listing courtesy of: OWN SRQ LLC

MLS# A4676710 - Status: Active View Property Details Add to Favorites View Map

• 17 BAYHEAD LN
• Price: $1,300,000
• Zip Code: 34229
• 2850 Square Feet
• Subdivision: BISHOPS COURT AT OAKS PRESERVE
• Bedrooms: 3 Baths: 2
• Impeccable is the only way to describe this charming, completely remodeled 3-bedroom, 2-bath residence that blends luxury with everyday comfort. No detail was overlooked in the renovation, resulting in a truly beautiful and thoughtfully designed home ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4678161 - Status: Active View Property Details Add to Favorites View Map

• 3621 N POINT RD #603
• Price: $1,295,000
• Zip Code: 34229
• 2680 Square Feet
• Subdivision: MERIDIAN AT THE OAKS PRESERVE
• Bedrooms: 3 Baths: 3
• COMPLETELY UPDATED WITH GORGEOUS VIEWS! Prepare to be captivated by this updated 3 bedroom, 3 bath condo in Meridian at The Oaks Preserve. This spacious residence offers a carefree, luxury lifestyle with a private elevator, open layout, and stunning ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

45 listings found

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