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YOUR 2026 GUIDE TO IN-TOWN LUXURY AND CLUB LIFESTYLE
Objective Perspective: The 2026 Grey Oaks Lifestyle
As of May 2026, Grey Oaks remains the premier in-town club destination in Naples. While generic sites use automated estimates, we provide the actual boots-on-the-ground reality. With a median sold price holding steady around $4,500,000, buyers prioritize this community for its three championship courses and the strictly managed 780 membership cap.
In the 2026 market, value is dictated by mechanical readiness. The social heart of the neighborhood, the Grey Oaks Clubhouse and the Wellness Center, have seen $60M+ in recent reinvestment, ensuring the community maintains its status as a top-tier North Naples destination.
Live Grey Oaks Insider Data: May 2026
Our live tracking shows active inventory moving at a pace of 116 days on market. Don't rely on automated estimates; see the actual contract prices and local trends.
ACCESS FULL GREY OAKS MARKET REPORT →*Data updated daily from FlexMLS for 100% accuracy.
Financial Essentials
- 2026 Initiation: $375,000 (Equity Golf)
- Annual Dues: Approximately $32,504/yr
- HOA: Varies by neighborhood enclave
- Focus: Mechanical health & Building code compliance
Town Center & Amenities
- Dining: Three distinct venues including indoor/outdoor dining
- Fitness: 30,000 Sq Ft Wellness Center & Lagoon Pool
- Racquet: 8 Har-Tru Courts & Championship Pickleball Center
- Security: 24/7 guard-gated & patrolled security
The Grey Oaks Property Breakdown
Understanding the distinct enclaves is essential for buyers. While the community features Coach Homes (starting at $2M) and Villas, the flagship is The Estuary at Grey Oaks, which offers custom estates ranging from $10M to $25M+.
Includes high-res community photos, amenity views, and original floor plan layouts.
Current Grey Oaks Listings
This impressive West Indies–style estate, designed and built by London Bay in 2009, is ideally situated on a private cul-de-sac in one of Grey Oaks’ most exclusive neighb...
- 5 Beds
- 6.5 Baths
- 226029006 MLS
Set within Traditions at Grey Oaks, this elegant residence offers immediate golf membership eligibility, providing the rare opportunity to bypass the club's multi-year go...
- 3 Beds
- 3.5 Baths
- 226025144 MLS
Welcome to perfection at 1385 Great Egret Trail, a custom estate in the exclusive gated enclave of Estuary at Grey Oaks. Inspired by timeless Santa Barbara architecture, ...
- 5 Beds
- 6.5 Baths
- 226024518 MLS
Welcome to Resort Style Living, Welcome to Grey Oaks! Walk to the Club from this exceptional estate with golf cart included. Also offering the rare opportunity to obtain...
- 4 Beds
- 5.5 Baths
- 226014131 MLS
An incredible 3+large den lakefront estate in Grey Oaks, with the opportunity for an IMMEDIATE GOLF MEMBERSHIP, available separately. This residence has been reimagined t...
- 3 Beds
- 3.5 Baths
- 226018715 MLS
Perfectly positioned within the sought-after Avila neighborhood of Grey Oaks Country Club, this Landmark-built courtyard residence offers a true front-row center seat to ...
- 3 Beds
- 3 Baths
- 226015203 MLS
Presenting an exceptional opportunity within the gates of the prestigious Grey Oaks Country Club—a professionally curated, turnkey-furnished residence designed for the mo...
- 4 Beds
- 3.5 Baths
- 226007565 MLS
Bright, refreshed and beautiful! Newly painted neutral interior and premium LED lighting enhance every living space throughout this stunning residence. Exceptional value ...
- 3 Beds
- 2.5 Baths
- 226003782 MLS
Welcome to Resort Style Living, Welcome to Grey Oaks! Beautifully furnished, this luxury home offers an ideal retreat in a peaceful setting. Designed with timeless fin...
- 3 Beds
- 3.5 Baths
- 225067730 MLS
Grey Oaks Golf & Country Club – Premier Cul-de-Sac Estate This estate residence is perfectly situated on one of the most coveted cul-de-sac lots in all of Grey Oaks Golf...
- 5 Beds
- 3.5 Baths
- 225066978 MLS