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Sarasota - The Oaks Real Estate Search

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Home  >  Sarasota  >  Osprey/Nokomis  >  The Oaks

The Oaks in Sarasota

The Oaks is known for fine upscale custom executive homes on sprawling lots behind a secure gated entry amongst the backdrop of a world-class member-owned thirty-six-hole championship golf course.  You know you “have arrived” when you call The Oaks home.  Three distinct subdivisions make up the Oaks.

The Oaks has mandatory membership for all homeowners.  See the latest fee schedule for membership at the Oaks here.

The Oaks Clubside – is home to single-family dwellings and surrounds the golf course to the east of US 41.  Driving through the main gates onto MacEwen Drive, you are first greeted with a stunning unobstructed view of the nearly 30,000 square foot clubhouse that recently underwent an $11 million dollar makeover.  Custom homes range from just over 2,000 up to over 9,000 square feet with two, three, or four-car garages.  Expect modem open designs with grand kitchens and tantalizing master suites. Homes were first built in 1986, and the latest home was completed in 2006.  The settings for each of the homesites are extremely well maintained to an exacting level of care, which is evident driving through on the tree-lined streets.  Lots will generally start in the 11,000-square-foot range and can top over an acre.

The Oaks Bayside and The Preserve have the feel and charm of a different time.  Heavily wooded in many areas, the developers chose a path for the streets to go around the mature Spanish moss-draped Oak trees rather than cut them down.  There is still the executive feel of the grand custom homes here, but the golf course atmosphere is not as prevalent.  It is not unusual to find homes with a Georgian-inspired design (as is the main clubhouse) or the flair of a Sonoma, California, wine country estate.  The western most homes will have views of the inter-coastal waterway and Siesta Key amongst the mangroves.

Membership to the club is mandatory in The Oaks, and you have a choice of a full membership or a slightly less expensive social membership.  Details and up-to-date pricing information can be found on The Oaks Club website.

Find similar gated golf course community homes for sale in the Sarasota area
The latest home sales in The Oaks
See the latest market analysis for The Oaks real estate market in Sarasota County Florida

Location-wise, you just cannot beat the Osprey location. The lifestyle here is reserved for the privileged few, as homes are scarce and in demand.  Siesta Key Beach is just 10 minutes away and you will drive right by the convenient Westfield Mall to get there. Access to the I-75 interstate is just 15 minutes away via Clark Road.

Schools in The Oaks are Laurel Elementary and Middle Schools, and the high school in Venice.

Be sure to take a look at recent sales and our market reports for The Oaks Clubside, Bayside, and condos. It just makes sense to know what the real estate market is doing prior to buying or selling.

We are the local experts when it comes to The Oaks. We love the Sarasota Real Estate market and welcome the opportunity to work with you and find that special place to call home. 

The Newest MLS Listings for The Oaks

409 N Point Road Unit 803, Osprey image
409 N Point Road Unit 803, Osprey — Meridian Iv $985,000

ENJOY BREATHTAKING SUNSET VIEWS ACROSS LITTLE SARASOTA BAY AND THE GULF FROM THIS STUNNING 8TH-FLOOR PENTHOUSE! This exceptional 2,203SF Condominium offers 3 Bedrooms, 3 ...

  • 3 Beds
  • 3 Baths
  • Meridian At The Oaks Preserve SubDv.
  • 34229 Zip Code
401 N Point Road Unit 504, Osprey image
401 N Point Road Unit 504, Osprey — Meridian At The Oaks Preserve $795,000 ▼

INCREDIBLE OPPORTUNITY AND A MUST SEE AT THE MERIDIAN AT THE OAKS - GREAT PRICE, BAY VIEW, UPDATED KITCHEN, PRIVATE 2 CAR GARAGE AND MORE! Beautifully updated and thought...

  • 3 Beds
  • 3 Baths
  • Meridian At The Oaks Preserve SubDv.
  • 34229 Zip Code
143 Osprey Point Drive, Osprey image
143 Osprey Point Drive, Osprey $575,000

One of the last available homesites in The Oaks Bayside. Almost 1/2 acre, at 17,647-square-feet, this exceptional lot presents a rare opportunity to build a custom luxury...

  • Oaks SubDv.
  • 34229 Zip Code
360 N Point Road, Osprey image
360 N Point Road, Osprey $1,495,000

Virtually Staged. A unique offering! This like-new, never lived in Spanish mission style home is a rare find. Move in ready and set on a private .63 acre lot in The Oaks ...

  • 3 Beds
  • 4 Baths
  • Oaks SubDv.
  • 34229 Zip Code
216 Osprey Point Drive, Osprey image
216 Osprey Point Drive, Osprey $695,000

One of the last remaining opportunities to build a custom luxury estate in The Oaks Bayside, one of Sarasota’s distinguished private country club communities. Behind 24-h...

  • Oaks The SubDv.
  • 34229 Zip Code
101 Osprey Point Drive, Osprey image
101 Osprey Point Drive, Osprey $4,790,000

Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates o...

  • 4 Beds
  • 6 Baths
  • Oaks SubDv.
  • 34229 Zip Code
103 Bishops Court Road, Osprey image
103 Bishops Court Road, Osprey $749,000

**LOCATED IN A DESIRABLE, MAINTENANCE-FREE, COUNTRY CLUB COMMUNITY** this Charming and Cozy 3-Bedroom, 2-Full Bath home sits on a premium Corner Lot directly across from ...

  • 3 Beds
  • 2 Baths
  • Oaks SubDv.
  • 34229 Zip Code
409 North Point Road Unit 401, Osprey image
409 North Point Road Unit 401, Osprey — Iv $560,000 ▼

Nestled at treetop level, in Meridian behind the gates of The Oaks Preserve, you will find this elegant residence waiting for you to make it your own. With a spacious ma...

  • 3 Beds
  • 3 Baths
  • Meridian At The Oaks Preserve SubDv.
  • 34229 Zip Code
3621 N Point Road Unit 301, Osprey image
3621 N Point Road Unit 301, Osprey — 3621 $525,000 ▼

Ready to live a stress-free luxury condo lifestyle? There is no place better to do it than this 3 bedroom, 3 bath residence in Meridian at The Oaks Preserve. Nestled amon...

  • 3 Beds
  • 3 Baths
  • Meridian At The Oaks Preserve SubDv.
  • 34229 Zip Code
409 N Point Road Unit 601, Osprey image
409 N Point Road Unit 601, Osprey — Meridian Iv $1,250,000

**FANTASTIC GULF AND BAY VIEWS FROM THIS UPDATED 6TH-FLOOR CORNER RESIDENCE** This spacious, light-filled corner unit offers nearly 2,600 sq. ft. of living space and feat...

  • 3 Beds
  • 3 Baths
  • Meridian At The Oaks Preserve SubDv.
  • 34229 Zip Code
401 N Point Road Unit 1001, Osprey image
401 N Point Road Unit 1001, Osprey — Meridian 3 $1,995,000

**Rarely available 10th-floor penthouse corner residence offering 3,029 square feet with sweeping Gulf and Bay views.** Ideally situated behind the secure gates of the hi...

  • 3 Beds
  • 3 Baths
  • Meridian At The Oaks Preserve SubDv.
  • 34229 Zip Code
385 N Point Road Unit 304, Osprey image
385 N Point Road Unit 304, Osprey — Meridian I $1,100,000 ▼

**MAGNIFICENTLY UPDATED, EXPANSIVE CORNER CONDO RESIDENCE OFFERING NEARLY 2,800 SQ FT OF REFINED LIVING SPACE** features 3 Bedrooms, 3 Full Baths, PLUS a Study/Den (or op...

  • 3 Beds
  • 3 Baths
  • Meridian At The Oaks Preserve SubDv.
  • 34229 Zip Code
401 N Point Road Unit 603, Osprey image
401 N Point Road Unit 603, Osprey — Iii $629,000 ▼

Virtually Staged. This incredible offering has everything you need to live a luxury condominium lifestyle in comfort and ease; 3 bedrooms, 3 full baths, a formal dining r...

  • 3 Beds
  • 3 Baths
  • Meridian At The Oaks Preserve SubDv.
  • 34229 Zip Code
538 Dove Pointe Drive, Osprey image
538 Dove Pointe Drive, Osprey $1,950,000 ▼

**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 Cou...

  • 4 Beds
  • 6 Baths
  • Oaks SubDv.
  • 34229 Zip Code
236 Saint James Park, Osprey image
236 Saint James Park, Osprey $2,700,000 ▼

Multigenerational living behind the gates of The Oaks Golf & Country Club. Set on a rare double lot at the end of a quiet cul-de-sac, this exceptional home is perfectly p...

  • 6 Beds
  • 7 Baths
  • Oaks SubDv.
  • 34229 Zip Code

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