The Oaks Club

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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.

87 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# A4420948 - Status: Active View Property Details Add to Favorites View Map

  • 136 OSPREY POINT DR
  • Price: $2,790,000
  • Zip Code: 34229
  • 6461 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 5+
  • Opportunity of a Life Time! This magnificent three-level mansion is located in the exclusive private gated community Oaks Bayside. This home is priced to sell and is below market and replacement value. Exquisite Brazillan cherry wood flooring through ... Read More
  • Listing courtesy of: BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

MLS# A4443045 - Status: Active View Property Details Add to Favorites View Map

  • 285 SUGAR MILL DR
  • Price: $1,695,000
  • Zip Code: 34229
  • 5578 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 5+
  • Escape to Paradise. Located in the waterfront community of Oaks Bayside, this one-of-a-kind walled and gated estate is a private oasis perfect for entertaining guests or for multi-generational living. The expansive open pool and patio area is positio ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4441248 - Status: Active View Property Details Add to Favorites View Map

  • 643 FERNWALK LN
  • Price: $1,695,000
  • Zip Code: 34229
  • 5246 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 4+
  • Elegantly defined, european and traditional, custom build home in the cul-de sac private street of the gated community of The Oaks. The moment you pull into the circular paver driveway and porte cochere, set on the lush tropical landscaping, you will ... Read More
  • Listing courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

MLS# A4208052 - Status: Active View Property Details Add to Favorites View Map

  • 91 OSPREY POINT DR
  • Price: $1,695,000
  • Zip Code: 34229
  • 5100 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 5+
  • Iconic architecture in Sarasota's premiere golf and country club. This magnificent 4-bedroom estate was designed and built by Bo MacEwen and brims with the essence of warm, Southern hospitality. Bo was the original architect for The Oaks and he creat ... Read More
  • Listing courtesy of: Michael Saunders & Company

MLS# A4428519 - Status: Active View Property Details Add to Favorites View Map

  • 425 MACEWEN DR
  • Price: $1,500,000
  • Zip Code: 34229
  • 5153 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 5+
  • This spacious 5 bedroom, 5.5 bath home offers over 5,100 square feet of living space and overlooks the par 3 fourth hole of The Oaks Heron Course. The huge gourmet kitchen features top of the line stainless steel appliances including a gas range. You ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4444745 - Status: Active View Property Details Add to Favorites View Map

  • 350 SUGAR MILL DR
  • Price: $1,498,246
  • Zip Code: 34229
  • 4100 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 3+
  • Pre-Construction. To be built. The Oaks Bayside. One of the few remaining homesites available to build your Dream Home with Henson Contractors. There is no time requirement for building and there is freedom to select another builder of your choice. ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4439437 - Status: Active View Property Details Add to Favorites View Map

  • 860 MACEWEN DR
  • Price: $1,450,000
  • Zip Code: 34229
  • 5084 Square Feet
  • Subdivision: OAKS 2 PH 2
  • Bedrooms: 4 Baths: 6+
  • THE EXCLUSIVE OAKS GOLF & TENNIS COUNTRY CLUB! Only Platinum and Elite club in the Sarasota Area (Top 10 Nationwide). This well designed home with gourmet kitchen has top of the line appliances with adjoining breakfast area, and is open convenientl ... Read More
  • Listing courtesy of: BRIGHT REALTY

MLS# N6106697 - Status: Active View Property Details Add to Favorites View Map

  • 854 MACEWEN DR
  • Price: $1,350,000
  • Zip Code: 34229
  • 9081 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 4+
  • Offering over 9,000 square feet of exquisite living space, this richly-detailed custom home is nestled on a guarded, private cul-de-sac. Entertain guests or simply relax as a family in the multitude of well-designed rooms from the living room with in ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4423128 - Status: Active View Property Details Add to Favorites View Map

  • 497 WEBBS CV
  • Price: $1,340,000
  • Zip Code: 34229
  • 6863 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 6 Baths: 6+
  • Seller will pay $25k toward club membership with approved contract. Located in the exclusive gated community of The Oaks Bayside. Totally remodeled home with too many improvements to list, everything is new including; new roof, air conditioners, new ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4207974 - Status: Active View Property Details Add to Favorites View Map

  • 340 OSPREY POINT DR
  • Price: $1,295,000
  • Zip Code: 34229
  • 6002 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 5+
  • If you want to live an enviable lifestyle with the comfort of being surrounded by nature, combined with the elegance of country club living, this 5 bedroom French Country styled home, with 5 full and 2 half baths is perfect for you! Play an early rou ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4442718 - Status: Active View Property Details Add to Favorites View Map

  • 402 WALLS WAY
  • Price: $1,263,000
  • Zip Code: 34229
  • 3464 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 4 Baths: 3+
  • Built in 2014 by Todd Johnston Homes, this spectacular courtyard style waterfront property has a separate casita that may be used as a guest quarters, artists studio or in law suite. Situated on a premier one acre lot, outdoor lighting showcases the ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4448933 - Status: Active View Property Details Add to Favorites View Map

  • 783 N MACEWEN DR
  • Price: $1,250,000
  • Zip Code: 34229
  • 4088 Square Feet
  • Subdivision: OAKS 2 PH 4-C PT 1
  • Bedrooms: 4 Baths: 4+
  • Impeccably maintained 4B/4.5 bath estate on a premium oversized lot with privacy on both sides and southern exposure to the rear. Gorgeous marble floors throughout, Lutron system for lights and shades, sound system with speakers though house and on l ... Read More
  • Listing courtesy of: CROWN PROPERTIES GROUP INC

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

  • 398 MACEWEN DR
  • Price: $1,250,000
  • Zip Code: 34229
  • 4743 Square Feet
  • Subdivision: OAKS 2 PH 3
  • Bedrooms: 4 Baths: 5+
  • Incredible 4 bedroom, 5.5 bath home with SEPARATE GUEST HOUSE 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 large 4,743 square foot house. Custom-built in 1998 ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4203589 - Status: Active View Property Details Add to Favorites View Map

  • 419 WALLS WAY
  • Price: $1,200,000
  • Zip Code: 34229
  • 5523 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 4 Baths: 4+
  • A recent price reduction makes this spectacular 4 bedroom, 4.5 bath colonial an opportunity too good to pass by! If you are a discriminating buyer, seeking the utmost in fine, country club living, you need to look no further. There is a reason this c ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4451482 - Status: Active View Property Details Add to Favorites View Map

  • 586 N MACEWEN DR
  • Price: $1,195,000
  • Zip Code: 34229
  • 4163 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 5+
  • Visualize yourself living on a beautiful golf course, surrounded by lush tropical landscape with sounds of a waterfall and nature beyond. That is exactly what this fabulous home offers. Set on cul-de-sac, this half-acre lot has flourishing plants and ... Read More
  • Listing courtesy of: BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

MLS# A4445561 - Status: Active View Property Details Add to Favorites View Map

  • 413 MACEWEN DR
  • Price: $1,150,000
  • Zip Code: 34229
  • 4152 Square Feet
  • Subdivision: OAKS 2 PH 3
  • Bedrooms: 3 Baths: 3+
  • You will love the incredible light that fills this 3 bedroom plus office, 3.5 bath home in The Oaks Clubside. Situated on a beautiful lot, it offers stunning views of the lake/pond and golf course. With a young roof, refinished pool with new equipme ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4448481 - Status: Active View Property Details Add to Favorites View Map

  • 165 SUGAR MILL DR
  • Price: $1,100,000
  • Zip Code: 34229
  • 3912 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 4+
  • Picture this. Gracious country club living on the Bayside of The Oaks Club in this 4 bedroom, 4.5 bath home. As you enter the new paver circular driveway, with three car side entry garage, it is evident how special this house is. Ideally situated on ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4448390 - Status: Active View Property Details Add to Favorites View Map

  • 894 MACEWEN DR
  • Price: $1,100,000
  • Zip Code: 34229
  • 3095 Square Feet
  • Subdivision: OAKS 2 PH 2
  • Bedrooms: 3 Baths: 3
  • Welcome to The Oaks with over 1,000 acres of luxury, shady oaks, rich flower beds, and impeccably maintained homes, none more than 894 MacEwen Drive. Enter through the hand carved mahogany doors to discover a completely transformed, contemporary home ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

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 RES R E

MLS# A4448792 - Status: Active View Property Details Add to Favorites View Map

  • 384 BUNKER HL
  • Price: $1,085,000
  • Zip Code: 34229
  • 3794 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 4 Baths: 3+
  • An amazing combination of cozy cottage and contemporary chic, this custom 4 bedroom, plus office, 3.5 bath home is situated on beautiful private lot in The Oaks Clubside. Nestled under oaks and beautifully landscaped, you will be enchanted by the ex ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4432972 - Status: Active View Property Details Add to Favorites View Map

  • 794 LYTHAM CIR
  • Price: $1,050,000
  • Zip Code: 34229
  • 3543 Square Feet
  • Subdivision: OAKS 2 PH 4C PART 1
  • Bedrooms: 4 Baths: 4
  • Well appointed, and completely updated, this 4 bedroom, 4 bath beauty will please the most discriminating buyer. You will be intrigued when you pull into the new pavered circular driveway with fountain. Once you enter though the double front doors, ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4429579 - Status: Active View Property Details Add to Favorites View Map

  • 53 FAIRWAY OAKS LN
  • Price: $1,019,000
  • Zip Code: 34229
  • 3774 Square Feet
  • Subdivision: OAKS 2 PH 4-A
  • Bedrooms: 4 Baths: 3+
  • Welcome to The Oaks Sarasota's only 2019-2020 Platinum Clubs of America Recipient. This Custom built home set on a private cul-de-sac is lushly landscaped and boasts over 3700 Sq. Ft. The elegant entrance is lined with columns leading to the covered ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4451164 - Status: Active View Property Details Add to Favorites View Map

  • 280 SARATOGA CT
  • Price: $1,000,000
  • Zip Code: 34229
  • 3970 Square Feet
  • Subdivision: OAKS 2 PH 2
  • Bedrooms: 4 Baths: 3+
  • Florida living: Custom built - Arthur Rutenberg Carlisle plan on quiet, private cul-de-sac Saratoga Court. Gorgeous home & lot which offer panoramic lake & golf course views. The sunny southwestern exposure is a delightful backdrop to the large open ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4447295 - Status: Active View Property Details Add to Favorites View Map

  • 922 MACEWEN DR
  • Price: $999,000
  • Zip Code: 34229
  • 4520 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 4+
  • Style and sophistication exude on this gorgeous Oaks clubside home that is perfectly situated on a lushly landscaped oversized lot with views of golf and lake beyond. This five bedroom, four full bath, two half bath home will provide the perfect atmo ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

87 listings found