The Oaks Club, Osprey: A Local Realtor's Guide to Living and Buying
The Oaks is a 24-hour guard-gated, member-owned country club community in Osprey, about 12 miles south of downtown Sarasota, set among the grand oaks along Sarasota Bay. It has two 18-hole championship golf courses, the Eagle and the Heron, plus one of the area's most respected racquets programs and a large clubhouse with several dining venues. Homes range from condos and maintenance-free villas to golf-course and bayside estates. Below is what I tell my own buyers, plus every Oaks property currently for sale.
By Grace Bonaccorso, Realtor, Preferred Shore Real Estate. Updated October 2026.
The Club
The Oaks Club is owned by its members. Beyond its two golf courses, it offers Har-Tru tennis courts, pickleball, an official croquet green, a heated community pool, a large fitness center, and fine and casual dining with an active social calendar. It has earned national recognition among private clubs.
Here's the most important difference from other Sarasota golf communities: at The Oaks, club membership is required with your home purchase. Buyers choose a golf or social membership, and the cost of that membership should be part of your budget from day one.
The Oaks Market Snapshot (October 2026)
As of mid-October 2026, about 28 properties are listed for sale inside The Oaks, including homes, villas, condos and a few homesites. Prices run from about $235,000 for a small condo to about $4.8 million for a bayside estate. The average is around $1.6 million, or roughly $465 per square foot. Most homes date from the mid-1980s to the early 2000s, with a handful of new custom homes built in the last few years. These figures change often, so treat them as a snapshot, not a guarantee.
The Neighborhoods Inside The Oaks
The golf neighborhoods line the Eagle and Heron courses, with many homes on half-acre or larger lots overlooking the fairways.
The Oaks Bayside is a separately gated enclave near Sarasota Bay, surrounded by water on three sides, with a community day dock. Some of the community's most valuable estates are here.
The Preserve includes maintenance-free villa neighborhoods such as Bishops Court, along with condominium residences, some with Gulf and Bay views.
Condos and villas throughout the community offer a lower-maintenance and lower-cost way into the club lifestyle.
Grace's Insider Notes for Oaks Buyers
Budget for the membership. Because membership is required, compare homes on total cost: price, membership, dues, HOA, taxes and insurance. Membership terms change, and recent listings have noted no waitlist, but I'll get current details straight from the club for you.
Near the bay, check elevation and flood insurance first. Bayside and lower-lying properties can carry very different flood zones and insurance costs from homes a few streets away. I have clients get elevation information and flood and homeowners quotes early in the inspection period.
Older homes mean opportunity. Many Oaks homes were built in the 1980s and 1990s on beautiful, mature lots. Some buyers renovate, and others build new. A few new custom homes went up recently, and homesites do come up. Roof, windows and systems age also affect your insurance, so we look at those closely.
The Oaks offers the widest range of any club community I cover. You can join a top private club with a villa or condo under $1 million, or buy a waterfront estate. That makes it a great fit for many different buyers, from active retirees to families.
What It's Like to Live in The Oaks
Life at The Oaks centers on the club, with golf, tennis, pickleball, croquet, fitness classes and a full social calendar, all under a canopy of old oaks. Outside the gates, Osprey offers easy access to the Legacy Trail for biking and walking, Oscar Scherer State Park, Historic Spanish Point, and the beaches of Siesta Key, Casey Key and Nokomis. Downtown Sarasota is about 12 miles north and downtown Venice is a short drive south.
Schools
The Oaks is in Sarasota County and is served by Sarasota County Schools. It's also close to Pine View School in Osprey, a nationally recognized public school for gifted students with its own eligibility requirements. Always confirm current school zoning and admission criteria for a specific address and student.
Is The Oaks Right for You?
The Oaks is a strong fit if you want an established, member-owned club with two golf courses, excellent racquet sports, a bayside setting and a wide choice of home types and prices. If you'd rather keep club membership optional, look at Laurel Oak or The Founders Club. If you want four courses to choose from, consider Lakewood Ranch Country Club.
The Oaks FAQ
Where is The Oaks?
The Oaks is in Osprey, Florida, zip code 34229, about 12 miles south of downtown Sarasota near Sarasota Bay.
Is membership required at The Oaks?
Yes. Membership in The Oaks Club is required with a home purchase. Buyers choose golf or social membership. Confirm current categories and costs with the club.
How many golf courses does The Oaks have?
Two 18-hole championship courses, the Eagle and the Heron.
Is The Oaks gated?
Yes. The Oaks has 24-hour guarded gates, and The Oaks Bayside has its own separate gate.
What do homes in The Oaks cost?
As of October 2026, properties for sale range from about $235,000 for a small condo to about $4.8 million for a bayside estate, averaging around $1.6 million.
