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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 that 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 what 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 complete 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 to 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 at 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 is Venice.

Be sure to take a look at recent solds 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

221 Osprey Point Drive, Osprey image
221 Osprey Point Drive, Osprey $2,595,000

**EXQUISITE AND SOPHISTICATED COUNTRY CLUB ESTATE** Custom Built in 2007 by Renowned Tandem Construction as found behind the gates of the coveted OAKS-BAYSIDE Neighborhoo...

  • 4 Beds
  • 4.5 Baths
  • Oaks SubDv.
  • 34229 Zip Code
3621 North Point Road Unit 301, Osprey image
3621 North Point Road Unit 301, Osprey — 3621 $850,000

Welcome to your slice of paradise. 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...

  • 3 Beds
  • 3 Baths
  • Meridian At The Oaks Preserve SubDv.
  • 34229 Zip Code
134 Marys Chapel Court, Osprey image
134 Marys Chapel Court, Osprey $2,625,000

**STRIKING, MOVE-IN READY, CONTEMPORARY, FULLY-RENOVATED ESTATE** found behind the gates of the coveted OAKS-BAYSIDE Country Club Neighborhood on Sarasota Bay waters… ent...

  • 5 Beds
  • 6.5 Baths
  • Oaks SubDv.
  • 34229 Zip Code
393 N Point Road Unit 602, Osprey image
393 N Point Road Unit 602, Osprey — Meridian Ii $949,900

**DAZZLING WATER AND SUNSET VIEWS FROM THIS GORGEOUS, CUSTOM-RENOVATED, UPPER FLOOR CONDO UNIT** may be found behind the gates of The Oaks Preserve. This re-imagined, be...

  • 3 Beds
  • 3 Baths
  • Meridian At The Oaks Preserve SubDv.
  • 34229 Zip Code
854 Macewen Drive, Osprey image
854 Macewen Drive, Osprey $3,850,000

**SPACIOUS, LUXURIOUS and BEAUTIFULLY RENOVATED, GOLF COURSE ESTATE** Boasts OVER 9,000sf and is situated on a prominent, private cul de sac lot of Over 3/4 Acres. Expan...

  • 4 Beds
  • 4.5 Baths
  • Oaks SubDv.
  • 34229 Zip Code
871 Macewen Drive, Osprey image
871 Macewen Drive, Osprey $2,725,000

Sited on arguably one of the best lots in The Oaks Club, this beautifully updated Georgian-style home and guest house blend perfectly with the surrounding landscape to de...

  • 5 Beds
  • 5.5 Baths
  • Oaks SubDv.
  • 34229 Zip Code
419 E Macewen Drive, Osprey image
419 E Macewen Drive, Osprey $1,995,000 ▼

BEAUTIFUL CUSTOM-BUILT HOME situated at the end of a cul-de-sac on a Premium .72-acre golf course and lake homesite. This 4,201 SF of living space home has a 3-car side e...

  • 4 Beds
  • 4.5 Baths
  • Oaks SubDv.
  • 34229 Zip Code
628 N Macewen Drive, Osprey image
628 N Macewen Drive, Osprey $2,099,000 ▼

**BEAUTIFULLY UPDATED GOLF COURSE ESTATE** This Ideal, SINGLE-STORY Home features 4 Beds + 4.5 Baths + 1 Office + 1 Den/Bonus Room + 3-Car Oversized Garage. With its LIG...

  • 4 Beds
  • 4.5 Baths
  • Oaks SubDv.
  • 34229 Zip Code
401 N Point Road Unit 301, Osprey image
401 N Point Road Unit 301, Osprey — 401 $850,000 ▼

3 Bed / 3 Bath Luxury High Rise condo offers 2,594 SqFt of living space and is located in the serene, gated community of The Oaks Preserve. The Condos in this community a...

  • 3 Beds
  • 3 Baths
  • Meridian At The Oaks Preserve SubDv.
  • 34229 Zip Code
340 Osprey Point Dr, Osprey image
340 Osprey Point Dr, Osprey $2,595,000 ▼

This grand estate is just as one might expect tucked behind the gates of The Oaks Bayside. Set back from the street and surrounded by lush landscaping which includes mat...

  • 5 Beds
  • 5.5 Baths
  • Oaks The SubDv.
  • 34229 Zip Code
Sugar Mill Drive, Osprey image
Sugar Mill Drive, Osprey $795,000

Rare opportunity to acquire one of the last remaining vacant parcels in prestigious Oaks Bayside. Build your Florida dream home using the builder of your choice within th...

  • Oaks SubDv.
  • 34229 Zip Code

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