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.

82 listings found

MLS# A4174521 - Status: Active View Property Details Add to Favorites View Map

  • 136 OSPREY POINT DR
  • Price: $3,199,900
  • Zip Code: 34229
  • 8843 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 7 Baths: 6+
  • Fantastic opportunity to own this prestigious home in The Oaks Bayside. You will be immediately impressed with the Georgian style of architecture as you first approach the circular driveway and the lush tropical foliage. The front facade of this home ... Read More
  • Listing courtesy of: Keller Williams On The Water

MLS# A4183696 - Status: Active View Property Details Add to Favorites View Map

  • 162 OSPREY POINT DR
  • Price: $3,000,000
  • Zip Code: 34229
  • 8057 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 4+
  • Secluded sanctuary for nature lovers. Luxury home can often be an oxymoron. The luxury may exist, but what makes a house a "home"? This property answers that question, as it embodies the true meaning of the phrase. The classic elegance of this reside ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4145623 View Property Details Add to Favorites View Map

  • N POINT RD
  • Price: $2,495,000
  • Zip Code: 34229
  • 0 Acres
  • The Oaks Preserve Phase IV - Located behind the gates of the Oaks, this 3.12 acre development sitewas acquired through forclosure. The site is entitled for 30 single family residential units. The zoning allowsfor up to four stories and great flexibil ... Read More
  • Listing courtesy of: SVN Commercial Advisory Group

MLS# A4173121 - Status: Active View Property Details Add to Favorites View Map

  • 285 SUGAR MILL DR
  • Price: $1,971,000
  • Zip Code: 34229
  • 5578 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 5+
  • Set gracefully amidst the lush landscaping in The Oaks Bayside, this stunning residence embodies style, sophistication and understated elegance at every turn. Idyllically positioned, this walled and gated lakefront estate features a beautifully desig ... Read More
  • Listing courtesy of: Premier Sothebys Intl Realty

MLS# A4167288 - Status: Active View Property Details Add to Favorites View Map

  • 324 OSPREY POINT DR
  • Price: $1,895,000
  • Zip Code: 34229
  • 5758 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 5
  • Perfectly positioned along North Creek in the Oaks Bayside, this architecturally significant and beautifully designed residence is uniquely representative of what modern buyers are looking for in a home. Understated elegance, clean lines, dramatic wi ... Read More
  • Listing courtesy of: Premier Sothebys Intl Realty

MLS# A4170988 - Status: Active View Property Details Add to Favorites View Map

  • 854 MACEWEN DR
  • Price: $1,825,000
  • Zip Code: 34229
  • 9081 Square Feet
  • Subdivision: OAKS 2 PH 2
  • Bedrooms: 4 Baths: 4+
  • Immerse yourself in luxury! One of the most exquisite estate offerings is nestled within the Oaks most distinguished Clubside enclaves. This incomparable dream unfolds over 9,000 square feet of quality craftsmanship including automated smart home ... Read More
  • Listing courtesy of: GENEROUS PROPERTY

MLS# A4174238 - Status: Active View Property Details Add to Favorites View Map

  • 168 COASTAL HAMMOCK CT
  • Price: $1,800,000
  • Zip Code: 34229
  • 4924 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 3 Baths: 3+
  • Bayfront in the Oaks. Custom designed walled Mediterranean estate in private cul-de-sac location with a 5 stop elevator. Views from several locations showcasing the gulf and the bay. Very livable floor plan with expansive master suite offering a sepa ... Read More
  • Listing courtesy of: CROWN PROPERTIES GROUP INC

MLS# A4180175 - Status: Active View Property Details Add to Favorites View Map

  • 468 WALLS WAY
  • Price: $1,795,000
  • Zip Code: 34229
  • 5698 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 4 Baths: 4+
  • This elegant home is nestled on more than a half-acre of property overlooking tranquil lake waters of The Oaks, featuring an array of beautiful finishes throughout. Majestic dcor greets you at every turn, including cathedral ceilings, a grand spiral ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4173463 - Status: Active View Property Details Add to Favorites View Map

  • 393 NORTH POINT RD #1002
  • Price: $1,690,000
  • Zip Code: 34229
  • 3738 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS
  • Bedrooms: 3 Baths: 2+
  • Discover this unique, sophisticated penthouse overlooking the wildlife of pristine Little Sarasota Bay. Beautiful Gulf of Mexico sunsets are yours to enjoy year round. Through a private elevator foyer the interiors are a welcoming experience in chic ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4146053 - Status: Active View Property Details Add to Favorites View Map

  • 340 OSPREY POINT DR
  • Price: $1,599,900
  • Zip Code: 34229
  • 6001 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 5 Baths: 5+
  • Timeless grandeur! This exquisite traditional estate was designed to perfection for luxury living with 5 bedrooms and 5.2 baths in the highly desirable Oaks Bayside. Volume ceilings, crown molding and architectural details are evident throughout th ... Read More
  • Listing courtesy of: Generous Property

MLS# A4172028 - Status: Active View Property Details Add to Favorites View Map

  • 221 OSPREY POINT DR
  • Price: $1,549,000
  • Zip Code: 34229
  • 4811 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 4+
  • Located in the prestigious district for 'Pine View School For The Gifted', the famed and consistently top rated high school nationwide, this extraordinary home presents a caliber of quality usually only reserved for multi-million dollar estates. A me ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4152178 - Status: Active View Property Details Add to Favorites View Map

  • 497 WEBBS CV
  • Price: $1,549,000
  • Zip Code: 34229
  • 6341 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 6 Baths: 6+
  • 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 flooring, new kitchens and baths, new pool, lanai screens, new trave ... Read More
  • Listing courtesy of: Premier Plus Realty

MLS# N5911132 - Status: Active View Property Details Add to Favorites View Map

  • 244 OSPREY POINT DR
  • Price: $1,259,118
  • Zip Code: 34229
  • 3132 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 3 Baths: 3
  • MOVE IN READY. Gracious living awaits you in this NEW construction home sited amidst the tree lined streets of The Oaks Bayside. You'll enjoy the privacy of this preserve homesite that backs to North Creek. The Ventalo plan offers a stylish open layo ... Read More
  • Listing courtesy of: EMERALD REALTY OF SOUTHWEST FLORIDA LLC

MLS# N5911141 - Status: Active View Property Details Add to Favorites View Map

  • 42 OSPREY POINT DR
  • Price: $1,258,310
  • Zip Code: 34229
  • 3692 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 3 Baths: 3
  • MOVE IN READY! The beauty of The Oaks Bayside awaits you in this NEW construction Villa Serena floorplan. Private homesite backs to natural woodlands and eagle preserve. Through the gorgeous iron & glass double-door entry, you'll find a spacious sing ... Read More
  • Listing courtesy of: EMERALD REALTY OF SOUTHWEST FLORIDA LLC

MLS# A4176551 - Status: Active View Property Details Add to Favorites View Map

  • 401 N POINT RD #1003
  • Price: $1,200,000
  • Zip Code: 34229
  • 2778 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3
  • Penthouse with PRIVATE TWO CAR GARAGE on the second floor of the building; this 3 bedroom, 3 bath condo in Meridian at The Oaks Preserve is truly a unique offering. Enjoy gorgeous views from the large screened balcony and almost every other room in t ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4166466 - Status: Active View Property Details Add to Favorites View Map

  • 398 E MACEWEN DR
  • Price: $1,200,000
  • Zip Code: 34229
  • 4743 Square Feet
  • Subdivision: OAKS 2 PH 3
  • Bedrooms: 4 Baths: 5+
  • Gorgeous golf course home with ENORMOUS BONUS ROOM! Large 4,743 sq ft house with 4 bedrooms, 5.5 baths, 5 car attached garage, on the 4th fairway of the Eagle course. All bedrooms are en suite, tile and wood floors throughout, office, over-sized lau ... Read More
  • Listing courtesy of: Coldwell Banker Res R E

MLS# A4174463 - Status: Active View Property Details Add to Favorites View Map

  • 133 OSPREY POINT DR
  • Price: $1,125,000
  • Zip Code: 34229
  • 4099 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 3
  • PRICE REDUCED!!! THE OAKS... Completely remodeled home located in the exclusive gated community of The Oaks Bayside with a private awesome pool with rock waterfall, spa and slide. Just across the street from Sarasota Bay. Recent improvements include ... Read More
  • Listing courtesy of: REGENCY REALTY SERVICES

MLS# A4187124 - Status: Active View Property Details Add to Favorites View Map

  • 677 TRENTON WAY
  • Price: $1,100,000
  • Zip Code: 34229
  • 5045 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 4 Baths: 4+
  • When you look up light and bright in the dictionary there is a photo of this home! A huge circular drive leads to the front of this majestic home with a 20+ foot columned entry with leaded glass doors and a large curved transom. As you enter the home ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4184148 - Status: Active View Property Details Add to Favorites View Map

  • 431 E MACEWEN DR
  • Price: $1,100,000
  • Zip Code: 34229
  • 4184 Square Feet
  • Subdivision: OAKS 2 PH 3
  • Bedrooms: 3 Baths: 4
  • This 3 bedroom plus office, 4 bath home is a former Tivoli model. Open and airy, it features large, spacious rooms. The living room, dining room, and family room have disappearing sliders that pocket behind the wall opening up the whole area to the ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# N5908759 - Status: Active View Property Details Add to Favorites View Map

  • 3603 N POINT RD #801BD6
  • Price: $1,100,000
  • Zip Code: 34229
  • 3991 Square Feet
  • Subdivision: MERIDIAN AT THE OAKS PRESERVE
  • Bedrooms: 3 Baths: 3+
  • SHORT SALE ** Magnificent panoramic views are waiting for you at this 4BR 3B PH unit atop this Meridian at the Oaks Preserve Building. Pleasantly appointed as you step in from the double door entry to the spacious, tray ceiling foyer, 10 ft ceilings ... Read More
  • Listing courtesy of: Gulf Coast Realty Team

MLS# A4181531 - Status: Active View Property Details Add to Favorites View Map

  • 34 OSPREY POINT DRIVE
  • Price: $1,099,995
  • Zip Code: 34229
  • 4515 Square Feet
  • Subdivision: OAKS
  • Bedrooms: 3 Baths: 3+
  • This gracious French-Provincial-inspired house teams with elegance and custom details including coffered ceilings, paneled walls, and hand-made solid-wood cabinets. The oversized living room with gas fireplace offers soaring ceilings and a graceful e ... Read More
  • Listing courtesy of: Mount Vernon Property Mgmt Inc

MLS# A4175498 - Status: Active View Property Details Add to Favorites View Map

  • 464 WALLS WAY
  • Price: $1,099,000
  • Zip Code: 34229
  • 4826 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 3 Baths: 3+
  • Step out of the boredom of predictable floor plans and into the elegance of a custom designed home that will excite and delight with originality, quality and presence. Situated on one of the most desirable cul de sac locations in the heart of the Oak ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4183489 - Status: Active View Property Details Add to Favorites View Map

  • 426 WALLS WAY
  • Price: $1,050,000
  • Zip Code: 34229
  • 4034 Square Feet
  • Subdivision: OAKS 2 PH 1
  • Bedrooms: 3 Baths: 4
  • Too hip to be square. This 3 bedroom, 4 bath home in The Oaks Clubside has a cachet of cool. The open floor design with eclectic finishes and appointments makes this unique space the ideal place for every way you want to live the country club lifest ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4167468 - Status: Active View Property Details Add to Favorites View Map

  • 896 MAC EWEN DR
  • Price: $1,050,000
  • Zip Code: 34229
  • 5174 Square Feet
  • Subdivision: THE OAKS
  • Bedrooms: 4 Baths: 5+
  • RECENTLY REDUCED! This exquisite custom-designed 4 bedroom, 5.5 bath in The Oaks offers magnificent golf course views. Serenity and luxury await you in this home that has extensive architectural details throughout. Beautiful 19marble and pecan wood ... Read More
  • Listing courtesy of: Coldwell Banker Res R E

MLS# A4170013 - Status: Active View Property Details Add to Favorites View Map

  • 457 MACEWEN DR
  • Price: $975,000
  • Zip Code: 34229
  • 3788 Square Feet
  • Subdivision: OAKS 2 PH 4-B
  • Bedrooms: 3 Baths: 3
  • The perfect Country Club lifestyle awaits in the gated Oaks Club of Sarasota. This beautifully executed custom built home by Tivoli is ideally situated on a prime site with sweeping Heron golf course views. Designed for open living and comfortable en ... Read More
  • Listing courtesy of: Michael Saunders & Company

82 listings found