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Grey Oaks Luxury Estate Homes for Sale

A Straightforward Guide to Grey Oaks Real Estate and Community Living

Grey Oaks is one of Naples’ most exclusive private country club communities, known for its estate homes, championship golf, and refined lifestyle. Spanning roughly 1,000 acres in the heart of Naples in Collier County, Grey Oaks offers gated privacy, resort amenities, and custom residences that often exceed $2 million. With three courses designed by Bob Cupp, a state-of-the-art wellness center, tennis, pickleball, and fine dining, Grey Oaks combines luxury living with a strong social calendar and active lifestyle opportunities. Its central location keeps downtown Naples, 5th Avenue, and Gulf beaches within easy reach.

Inside Grey Oaks

  • Location: Central Naples, east of US 41, bordered by Golden Gate Parkway and Airport Pulling Road, minutes to downtown and Gulf beaches
  • Size & Homes: ~1,000 acres with ~900 luxury residences, including custom estates, villas, and coach homes
  • Prices: Villas from $1.5M+; custom estates commonly $3M–$10M+ depending on size and location
  • Amenities: Three private 18-hole golf courses (Pine, Palm, and Estuary – all designed by Bob Cupp); Grey Oaks Country Club with dining, 30,000+ sq ft wellness center, spa, racquet complex, and resort-style pool
  • Distinctive Feature: One of Naples’ few communities with three private 18-hole golf courses and multiple clubhouses, emphasizing exclusivity and estate-scale living
Aerial view of luxury custom estates and private golf course at Grey Oaks, a gated equity country club community with homes for sale in Naples, FL

Types of Homes in Grey Oaks

Grey Oaks is organized into three main enclaves, each with its own character. The original Grey Oaks neighborhood features Mediterranean-inspired custom estates on golf and lakefront sites. The Estuary at Grey Oaks is the most private section, with expansive custom homes on preserve and lakefront lots, often priced well above $10 million. Miramonte offers luxury villas with lower-maintenance living but no compromise on finishes. Developed in the early 1990s by the Barron Collier Companies, Grey Oaks has grown into one of Naples’ most respected master-planned luxury communities. Across the community, buyers will find coach homes, villas, and custom estates featuring impact glass, expansive lanais, guest casitas, and private pools. Prices begin around $1.5 million for villas and exceed $10 million for estate properties.

What You’ll Find Living in Grey Oaks

Life in Grey Oaks centers on its private club and resort-style amenities. Residents enjoy three Bob Cupp–designed golf courses, practice facilities, and a full-service pro shop. The Grey Oaks Country Club features a 30,000+ square-foot wellness center with spa, fitness programs, and a resort pool. The racquet complex includes tennis and pickleball courts with instruction and organized play. Dining spans formal and casual options, including terraces overlooking the fairways. Social life is active, with wine tastings, seasonal galas, and a full calendar of member events. Just outside the gates, Naples’ 5th Avenue, Waterside Shops, and Gulf beaches are minutes away.

What to Know About Grey Oaks

Grey Oaks delivers one of Naples’ most prestigious addresses, but exclusivity comes at a premium. Membership in the equity country club is mandatory, with substantial initiation fees and ongoing dues. Costs are higher than bundled or semi-private golf communities in Naples, reflecting its three private courses and comprehensive amenities. HOA fees are also elevated, covering 24-hour security, common-area maintenance, and full-service upkeep. Seasonal traffic on Golden Gate Parkway and Airport Pulling Road can be a consideration, though the central location provides quick access to shopping, dining, and the beaches. Compared with Pelican Bay, which emphasizes beachfront access and private trams, Grey Oaks appeals to those seeking private golf and custom estates. Against Lely Resort, it offers more exclusivity and fewer homes but at higher cost.

Practical Considerations for Grey Oaks Buyers

  • HOA & Club Fees: Grey Oaks is a mandatory equity club community with initiation and annual dues; HOA fees vary by enclave
  • Golf: Three private 18-hole golf courses; membership required
  • CDD: None — community infrastructure is privately maintained through HOA/club funding
  • Transportation: About 4 miles (14 minutes) to Waterside Shops, 6 miles (18 minutes) to Naples Beach & Pier, and 28 miles (35 minutes) to RSW Airport.
  • Schools: Served by Collier County Public Schools
  • Healthcare: NCH Baker Downtown (~10 minutes) and Physicians Regional Pine Ridge (~15 minutes)
Aerial view of Grey Oaks in Naples, FL, an exclusive private country club community with homes for sale near the Gulf of Mexico, featuring championship golf courses and luxury estates

Frequently Asked Questions about Grey Oaks

Is Grey Oaks a gated community?

Grey Oaks is fully gated with 24-hour staffed security and multiple controlled entry points.

How many golf courses does Grey Oaks have?

Three private championship courses — the Pine, Palm, and Estuary — all designed by Bob Cupp.

Is membership required at Grey Oaks?

Yes. Grey Oaks is an equity membership community, and joining the country club is mandatory for homeowners.

What types of homes are in Grey Oaks?

Options include luxury villas and coach homes (starting around $1.5M) and custom estates (ranging $3M–$10M+). The Estuary enclave contains the community’s most exclusive lakefront and preserve-view estates.

Are rentals allowed in Grey Oaks?

Rental policies vary by enclave. Some neighborhoods allow annual rentals, while others have restrictions. Buyers should verify HOA rules before purchase, as policies can impact flexibility and resale value.

How do Grey Oaks club costs compare to other communities?

Club initiation and dues are higher than in bundled or semi-private golf communities, reflecting its three private courses, multiple clubhouses, and large-scale amenities.

Find Your Home in Grey Oaks

Grey Oaks homes for sale in Naples deliver premier country club living with custom estates, world-class amenities, and one of the city’s most prestigious addresses. From luxury villas in Miramonte to expansive estates in the Estuary, the community combines privacy, elegance, and a strong social scene in a central location. Worthington Realty can help you understand membership details, home options, and lifestyle benefits so you can move forward with clarity.

Most homeowners feel overwhelmed when it’s time to move. At Worthington Realty, we provide personalized guidance and clear communication so that you feel heard, valued, and confident in your decisions.