$1,195,000
2 Bed 2 Bath Condominium for Sale in WINDWARD CAY, FL
4460 YACHT HARBOR Drive, Naples, FL, 34112
About this home
Welcome to 4460 Yacht Harbor Drive in desirable Windward Cay enclave in Windstar on Naples Bay. If you are considering Gulf Shore Blvd, Moorings or Park Shore condo living Windstar offers the waterfront lifestyle while being set back and protected from the bay for true peace of mind. This redesigned and fully renovated corner end-unit penthouse unit is located in a boutique 6-unit elevator building with only 2 units per floor and features 2 Bedrooms+den and 2 Baths in almost 2200 square feet of truly luxurious living space. Enter into a welcoming foyer to a truly fabulous open-concept living space with a contemporary light and airy vibe with soaring vaulted ceilings and stunning natural views all around. Spacious living room with walls of glass boasting unparalleled Audubon Society-certified views overlooking the serene 8th fairway, lake and tropical mangroves. A true chef's eat-in kitchen replete with custom shaker cabinetry, GE Monogram stainless steel appliances, pot filler, contemporary quartz countertops, open shelving with lighting, breakfast bar and custom built-in Brazilian walnut dining table ideal for daily dining and entertaining. Custom built-in office nook ideal for today's work from home lifestyle. Convenient laundry room with side by side washer/dryer, custom built-in cabinetry and counter affording great storage. Master suite oasis features spacious bedroom, dual walk-in closets with California custom built-ins and a spa-like master bath with a gorgeous oversized walk-in shower with dual rain heads, contemporary floating double vanity and freestanding soaking tub. Large guest bedroom with a gorgeous view plus a lovely full hall bathroom. Air conditioned glassed-in lanai currently used as a TV room could also be set up as a home office or additional guest quarters. Oversized covered parking for 2 vehicles and electrical outlet for your golf cart. No expense spared in this truly custom renovation with the finest of materials and craftsmanship a rarity to find this level of high-design and finish in a condo in Windstar. Windstar on Naples Bay is the only gated golf community with Tom Fazio designed 18-hole golf course that offers direct bay access, a private beach plus dock on Keewaydin Island with seasonal October-July boat shuttle included in your Windstar HOA plus a full service 73-slip deep water marina. Newly renovated clubhouse (separate membership) with multiple dining areas with stunning views of Naples Bay and Port Royal, 6 Har-Tru tennis courts, 3 bocce courts and a new state of the art fitness center slated for late 2026 completion. Preferred location just a short 2 mile drive via car, bike or golf cart to downtown's 5th Avenue South and 3rd Street South known worldwide for its fine dining, shopping and beaches. Situated in the vibrant Bayshore Arts District, Windstar is walkable to Naples Botanical Garden and Naples Pickleball Center home of the pickleball US Open. Easy access to I-75, Naples and Fort Myers airports.
Property details
- Type
- Condominium
- Year built
- 1987
- Interior
- 2,166 sqft
- Lot size
- Not specified
- Acreage
- Not specified
- Garage
- None
- Days on market
- 133
- Total association fees
- $20,324/yr (~$1,694/mo)
- CDD
- None
- Est. taxes (1.4%)
- $16,730/yr
- Flood zone (area est.)
- Not available
- Storm protection
- Impact Windows/Doors
- Exposure
- Northwest
- Waterfront
- No
- Gulf access
- No
- Gulf access type
- N/A
- Pool
- No
- Spa
- No
- Natural gas
- No
- Water
- Public
- Sewer
- Public Sewer
- New construction
- No
- Pets
- Call, Conditional
- County
- Collier
Total association fees sums the core association dues the MLS feed provides (HOA, condo/master association, and land lease), normalized to a yearly figure. These are separate from and additional to specialty charges — mandatory club or food-and-beverage minimums, special assessments, and rec-lease fees — which the IDX feed does not carry. Always confirm the full fee schedule with the HOA or listing agent.
Maintenance included in the fee
What the association dues cover, per the MLS. Confirm the full schedule with the HOA.
Amenities
Based on the $/sqft of 5 comparable homes sold nearby in the last 12 months. Indicative, not an appraisal.
Seeing several homes? Build a tour and we'll route it for you.
Your notes on this home
Keep private notes on this home — what you love, what to ask about — saved to your account and shared with your agent.
Recently sold nearby
Closed comparable sales within ~1 mile in the last 12 months — similar price, size, beds/baths, and age.
| Address | Sold | Sold price | Beds/Baths | Sq ft | $/sqft |
|---|---|---|---|---|---|
| 4451 Yacht Harbor Drive | Jun 2026 | $1,137,000 | 3/2 | 2,345 | $485 |
| 3876 Clipper Cove Drive | Dec 2025 | $1,480,000 | 3/3 | 2,286 | $647 |
| 1737 YORK ISLAND Drive | Dec 2025 | $1,375,000 | 3/2 | 2,336 | $589 |
| 3722 Haldeman Creek Drive NV3 | Dec 2025 | $1,325,000 | 2/2 | 2,156 | $615 |
| 2472 Breakwater Way 11102 | Jun 2026 | $1,200,000 | 2/2 | 2,348 | $511 |
| Average | 5 comps | $1,303,400 | $569 |
Market trends — Naples
Median of closed MLS sales each month over the available window. Months with too few sales are omitted; the range extends automatically as more sales close.
Live area medians from the MLS · see all listings. Indicative, not an appraisal.
Price & status history
Down $120,000 (10%) from the original list price.
| Feb 12, 2026 | Sold | $1,075,000 |
| Sep 9, 2025 | Listed | $1,195,000 |
The good, the trade-offs & the location
- Storm protection: Impact Windows/Doors
- Built 1987 — pre-2002 construction may carry older wind codes and higher insurance
- No garage listed
- Higher association fees (~$20,324/yr)
Straight-line distances to major SWFL amenities — approximate; actual drive times vary.
Nearby schools
Get more information on their programs, scores, and extracurriculars on each school's page · browse the full schools directory.
Similar homes nearby
$1,000,000
MLS# 2250850002499 Pine Street, Naples, FL, 34112
$1,100,000
MLS# 226014670850 6th Avenue 204, Naples, FL, 34102
$989,000
MLS# 2260124551225 Sandpiper Street, Naples, FL, 34102
$1,375,000
MLS# 20260232714700 Yacht Harbor Drive 622, Naples, FL, 34112
$1,150,000
MLS# 2250658084936 Tamiami Trail 213, Naples, FL, 34113
$1,290,000
MLS# 2260050591260 Forest Avenue, Naples, FL, 34102
Listing information is provided in part by the Florida Gulf Coast Multiple Listing Service (MLS) through its Broker Reciprocity / Internet Data Exchange (IDX) program. Properties displayed may be listed by brokerages other than SWFL Relocation Team. Data is deemed reliable but is not guaranteed accurate by the MLS or this brokerage and should be independently verified. Fees, flood zones, taxes, square footage, and school assignments are estimates from the feed and must be confirmed. © 2026 SWFL Relocation Team. All rights reserved.