14540 Headwater Bay Ln, Fort Myers, FL 33908
For Sale $2,600,000
The Club At Olde Cypress
Lively. Friendly. Welcoming.
- 18 Holes of Golf by P.B. Dye
- Renovated Clubhouse & Vibrant Events
- Pickleball, Tennis, Bocce, Pool, & Fitness
- Year-Round Social Calendar with Events
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Melissa Hansen SCHEDULE A TOUR
“Her true love is meeting and connecting with people. Melissa enjoys introducing new members to the community and helping them feel right at home.”
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CONTACT MEMBERSHIP DIRECTORDisclaimer: The Club at Olde Cypress provides the club-related content featured on this page. All real estate information, including property listings and marketing services, is offered exclusively by Club Properties, an independent and neutral real estate brokerage. The Club is not engaged in the sale or rental of any properties and does not act as a real estate broker. Club Properties is solely responsible for the real estate content presented.
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Contact the Listing Agent directly:
Listing Agent: Elise Starr
Agent Phone:
(239) 209-3960
Agent Email:
elise.luxuryproperty@gmail.com
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14540 HEADWATER BAY | Gulf Harbour Yacht & Country Club Experience elevated courtyard living in this beautifully upgraded residence located in the exclusive, gated Gulf Harbour Yacht & Country Club. Designed for privacy, luxury, and effortless indoor-outdoor living, this home wraps around an expansive central courtyard featuring a sparkling pool, relaxing hot tub, and a fully equipped outdoor kitchen, your own private retreat at the heart of the home. Step inside to discover a stunning, completely remodeled kitchen, anchored by a dramatic waterfall-edge quartz island and featuring premium finishes throughout. The kitchen is outfitted with a Monogram induction cooktop, pot filler, modern cabinetry, updated lighting, and sleek appliances that make both cooking and entertaining a joy. Porcelain tile flooring flows seamlessly throughout the main living spaces, creating a clean and cohesive feel. Elegant French doors lead into the formal dining room, while a stylish bar area, complete with a temperature-controlled wine chiller, offers the perfect space for evening gatherings. The primary suite is a private sanctuary featuring a luxurious bathroom with tumbled porcelain tile, a relaxing soaking tub, and shower that doubles as an impressive steam shower, providing a true spa-like experience. The additional guest bedrooms are located on the second-floor wing and connect to the casita via a charming upper-level lanai, offering unique indoor-outdoor flow and privacy for guests. The separate casita is exceptionally well-appointed with its own microwave, sink, refrigerator, and stackable washer/dryer, making it perfect for long-term guests, family, or live-in support. An additional office area off the main house provides a quiet and functional workspace, ideal for those who work remotely or need a dedicated study. Completing the home are 2 spacious, 2-car garages, offering ample storage and room for vehicles, golf carts, bikes, and more. Located within one of Southwest Florida’s most sought-after communities, residents of Gulf Harbour enjoy access to championship golf, a deep-water marina, tennis, fitness center, spa, clubhouse dining, and vibrant social events. Golf and Sport memberships opportunities are be available, offering the rare chance to enjoy the full lifestyle without the standard waitlist. 14540 Headwater Bay offers a rare fusion of luxury, comfort, and architectural character- an exceptional courtyard home designed for refined Florida living.
Bar
Built-In Cabinets
Foyer
Beach - Private
Spa/Hot Tub
Fitness Center
Full Service Spa
Golf Course
Internet Access
Shopping
Streetlight
Underground Utility
Marina
Play Area
Private Membership
Putting Green
Restaurant
Sauna
Taxes: $19,153.32
Tax Year: 2025
Master Association Fees: $1,730.00
Association Fee: $1,074.00
Association Fee Frequency: Annually
Screened Lanai/Porch
Built In Grill
Courtyard
Outdoor Kitchen
Dishwasher
Double Oven
Microwave
Range
Refrigerator/Freezer
Golf Course
Building Design: Single Family
Community Type: Boating, Gated, Golf Course, Tennis
MLS Area: Fm09 - Fort Myers Area
Price per Square Feet: $533.99
Total Floors: 2
Water: Central
Construction: Concrete Block, Stucco
Foreclosure: No
Short Sale: No
Date Listed: 2026-01-09 00:00:00
Pool: Yes
Pool Type: Below Ground, Equipment Stays, Salt Water
Pool Description: Below Ground, Equipment Stays, Salt Water
Private Spa: Yes
Furnished: Negotiable
Parking: Attached
Garage Description: Attached
Garage Spaces: 4
Flooring: Carpet, Vinyl
Roof: Tile
Heating: Central Electric
Cooling: Central Electric
Fireplace: No
Storm Protection: None
Security: Gated Community
Laundry: Laundry In Residence
Irrigation: Reclaimed
55+ Community: No
Pets: Yes
Restrictions: Architectural, Deeded, No Commercial, No Rv
Maintenance: Legal/Accounting, Manager, Reserve, Street Maintenance
Rear Exposure: Sw
Lot Desc.: Zero Lot Line
Amenities: Beach - Private, Spa/Hot Tub, Fitness Center, Full Service Spa, Golf Course, Internet Access, Shopping, Streetlight, Underground Utility, Marina, Play Area, Private Membership, Putting Green, Restaurant, Sauna
Listing Courtesy Of: John R. Wood Properties
elise.luxuryproperty@gmail.com
14540 HEADWATER BAY | Gulf Harbour Yacht & Country Club Experience elevated courtyard living in this beautifully upgraded residence located in the exclusive, gated Gulf Harbour Yacht & Country Club. Designed for privacy, luxury, and effortless indoor-outdoor living, this home wraps around an expansive central courtyard featuring a sparkling pool, relaxing hot tub, and a fully equipped outdoor kitchen, your own private retreat at the heart of the home. Step inside to discover a stunning, completely remodeled kitchen, anchored by a dramatic waterfall-edge quartz island and featuring premium finishes throughout. The kitchen is outfitted with a Monogram induction cooktop, pot filler, modern cabinetry, updated lighting, and sleek appliances that make both cooking and entertaining a joy. Porcelain tile flooring flows seamlessly throughout the main living spaces, creating a clean and cohesive feel. Elegant French doors lead into the formal dining room, while a stylish bar area, complete with a temperature-controlled wine chiller, offers the perfect space for evening gatherings. The primary suite is a private sanctuary featuring a luxurious bathroom with tumbled porcelain tile, a relaxing soaking tub, and shower that doubles as an impressive steam shower, providing a true spa-like experience. The additional guest bedrooms are located on the second-floor wing and connect to the casita via a charming upper-level lanai, offering unique indoor-outdoor flow and privacy for guests. The separate casita is exceptionally well-appointed with its own microwave, sink, refrigerator, and stackable washer/dryer, making it perfect for long-term guests, family, or live-in support. An additional office area off the main house provides a quiet and functional workspace, ideal for those who work remotely or need a dedicated study. Completing the home are 2 spacious, 2-car garages, offering ample storage and room for vehicles, golf carts, bikes, and more. Located within one of Southwest Florida’s most sought-after communities, residents of Gulf Harbour enjoy access to championship golf, a deep-water marina, tennis, fitness center, spa, clubhouse dining, and vibrant social events. Golf and Sport memberships opportunities are be available, offering the rare chance to enjoy the full lifestyle without the standard waitlist. 14540 Headwater Bay offers a rare fusion of luxury, comfort, and architectural character- an exceptional courtyard home designed for refined Florida living.
Property Details
Price: $2,600,000
Sq Ft: 4,869
($534 per sqft)
Bedrooms: 4
Bathrooms: 3
Partial Baths: 1
City: Fort Myers
County: Lee
Type: Single Family
Development: Gulf Harbour Yacht And Country Club
Subdivision: Edgewater
Acres: 0.36
Virtual Tour/Floorplan: View
Year Built: 1996
Listing Number: 2025020711
Status Code: A-Active
Taxes: $19,153.32
Tax Year: 2025
Garage:
4
/
Attached
Furnishings: Negotiable
Pets Allowed: Yes
Interior Features:
Bar
Built-In Cabinets
Foyer
Amenities:
Beach - Private
Spa/Hot Tub
Fitness Center
Full Service Spa
Golf Course
Internet Access
Shopping
Streetlight
Underground Utility
Marina
Play Area
Private Membership
Putting Green
Restaurant
Sauna
Financial Information:
Taxes: $19,153.32
Tax Year: 2025
Master Association Fees: $1,730.00
Association Fee: $1,074.00
Association Fee Frequency: Annually
Exterior Features:
Screened Lanai/Porch
Built In Grill
Courtyard
Outdoor Kitchen
Equipment:
Dishwasher
Double Oven
Microwave
Range
Refrigerator/Freezer
View:
Golf Course
Additional Information:
Building Design: Single Family
Community Type: Boating, Gated, Golf Course, Tennis
MLS Area: Fm09 - Fort Myers Area
Price per Square Feet: $533.99
Total Floors: 2
Water: Central
Construction: Concrete Block, Stucco
Foreclosure: No
Short Sale: No
Date Listed: 2026-01-09 00:00:00
Pool: Yes
Pool Type: Below Ground, Equipment Stays, Salt Water
Pool Description: Below Ground, Equipment Stays, Salt Water
Private Spa: Yes
Furnished: Negotiable
Parking: Attached
Garage Description: Attached
Garage Spaces: 4
Flooring: Carpet, Vinyl
Roof: Tile
Heating: Central Electric
Cooling: Central Electric
Fireplace: No
Storm Protection: None
Security: Gated Community
Laundry: Laundry In Residence
Irrigation: Reclaimed
55+ Community: No
Pets: Yes
Restrictions: Architectural, Deeded, No Commercial, No Rv
Maintenance: Legal/Accounting, Manager, Reserve, Street Maintenance
Rear Exposure: Sw
Lot Desc.: Zero Lot Line
Amenities: Beach - Private, Spa/Hot Tub, Fitness Center, Full Service Spa, Golf Course, Internet Access, Shopping, Streetlight, Underground Utility, Marina, Play Area, Private Membership, Putting Green, Restaurant, Sauna
Map of 14540 Headwater Bay Ln, Fort Myers, FL 33908
Listing Courtesy Of: John R. Wood Properties
elise.luxuryproperty@gmail.com