5950 Trailwinds Dr #222, Fort Myers, FL 33907
For Sale $279,900
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Beautifully updated and rarely available, this highly sought-after second-floor “D” unit offers sweeping pond and golf course views within the golf community of The Hideaway Country Club.. One of the standout features is the full set of hurricane-impact windows and sliders—a rare and valuable upgrade in a community where many condos still have original windows and shutters—providing peace of mind, energy efficiency, and a quiet interior. The redesigned lanai has been seamlessly incorporated into the living area, creating a bright and expansive space with a dramatic wall of windows that immediately showcases the stunning water and fairway views the moment you enter. Extensively updated throughout, the home features luxury vinyl plank flooring, fresh interior paint, recessed lighting, plantation shutters in all bedrooms, updated kitchen appliances including a modern induction cooktop, and tastefully renovated bathrooms. Impeccably maintained and move-in ready, this condo combines comfort, style, and functionality. Residents of Greenbriar enjoy their own private pool and tiki bar, plus a separate grilling and gathering area. For golf enthusiasts, the community offers one of the area’s most enjoyable and affordable golf memberships—while still allowing residents the flexibility of optional membership with no mandatory golf fees. A golf cart is included, adding convenience and enhancing the country club lifestyle. Ideally located in Fort Myers, just minutes from shopping, dining, RSW International Airport, and Southwest Florida’s beautiful beaches, this property is perfect as a full-time residence or seasonal retreat. A full list of upgrades and improvements is available in the MLS supplements.
Smoke Detectors
Volume Ceiling
Walk- In Closet(s)
Window Coverings
Clubhouse
Pool
Community Room
Fitness Center
Storage
Golf Course
Internet Access
Putting Green
Restaurant
Streetlight
Tennis Court(s)
Car Wash Area
Taxes: $1,727.00
Tax Year: 2025
Master Association Fees: $5,325.00
Association Fee: $10,893.00
Association Description: Mandatory
Cooktop
Dishwasher
Disposal
Dryer
Microwave
Range
Refrigerator
Safe
Self Cleaning Oven
Washer
Y
Building Description: Two Story, Low Rise (1-3)
Building Design: Low Rise (1-3 Floors)
Community Type: Gated, Golf Course
MLS Area: The Hideaway Country Club
Total Square Footage: 1,436
Total Floors: 1
Water: Assessment Paid
Construction: Concrete Block, Stucco
Date Listed: 2026-05-06 00:00:00
Pool Description: Community
Furnished: Negotiable
Windows: Window Coverings
Parking: 1 Assigned, Covered, Golf Cart, Guest, Paved, Detached Carport
Roof: Shingle
Heating: Central Electric
Cooling: Ceiling Fan(S), Central Electric
Storm Protection: Impact Resistant Windows
Security: Smoke Detector(S), Gated Community
Laundry: Washer/ Dryer Hookup, Laundry In Residence
Irrigation: Central
Pets: Limits
Restrictions: No Commercial, No R V
Maintenance: Cable, Insurance, Internet/ Wi Fi Access, Lawn/ Land Maintenance, Legal/ Accounting, Pest Control Exterior, Rec Facilities, Reserve, Street Lights, Street Maintenance
Rear Exposure: E
Lot Desc.: Golf Course
Amenities: Clubhouse, Pool, Community Room, Fitness Center, Storage, Golf Course, Internet Access, Putting Green, Restaurant, Streetlight, Tennis Court(S), Car Wash Area
Listing Courtesy Of: Realty One Group Mvp
homesbychrisjackson@gmail.com
Beautifully updated and rarely available, this highly sought-after second-floor “D” unit offers sweeping pond and golf course views within the golf community of The Hideaway Country Club.. One of the standout features is the full set of hurricane-impact windows and sliders—a rare and valuable upgrade in a community where many condos still have original windows and shutters—providing peace of mind, energy efficiency, and a quiet interior. The redesigned lanai has been seamlessly incorporated into the living area, creating a bright and expansive space with a dramatic wall of windows that immediately showcases the stunning water and fairway views the moment you enter. Extensively updated throughout, the home features luxury vinyl plank flooring, fresh interior paint, recessed lighting, plantation shutters in all bedrooms, updated kitchen appliances including a modern induction cooktop, and tastefully renovated bathrooms. Impeccably maintained and move-in ready, this condo combines comfort, style, and functionality. Residents of Greenbriar enjoy their own private pool and tiki bar, plus a separate grilling and gathering area. For golf enthusiasts, the community offers one of the area’s most enjoyable and affordable golf memberships—while still allowing residents the flexibility of optional membership with no mandatory golf fees. A golf cart is included, adding convenience and enhancing the country club lifestyle. Ideally located in Fort Myers, just minutes from shopping, dining, RSW International Airport, and Southwest Florida’s beautiful beaches, this property is perfect as a full-time residence or seasonal retreat. A full list of upgrades and improvements is available in the MLS supplements.
Property Details
Price: $279,900
Sq Ft: 1,436
($195 per
sqft)
Bedrooms: 3
Bathrooms: 2
City: Fort Myers
County: Lee
Type: Condo
Development: The Hideaway Country Club
Subdivision: Greenbriar Village
Acres: 0.1959
Virtual Tour/Floorplan: View
Year Built: 1988
Listing Number: 226017663
Status Code: A-Active
Taxes: $1,727.00
Tax Year: 2025
Garage:
Furnishings: Negotiable
Pets Allowed: Limits
Interior Features:
Smoke Detectors
Volume Ceiling
Walk- In Closet(s)
Window Coverings
Amenities:
Clubhouse
Pool
Community Room
Fitness Center
Storage
Golf Course
Internet Access
Putting Green
Restaurant
Streetlight
Tennis Court(s)
Car Wash Area
Financial Information:
Taxes: $1,727.00
Tax Year: 2025
Master Association Fees: $5,325.00
Association Fee: $10,893.00
Association Description: Mandatory
Equipment:
Cooktop
Dishwasher
Disposal
Dryer
Microwave
Range
Refrigerator
Safe
Self Cleaning Oven
Washer
View:
Y
Additional Information:
Building Description: Two Story, Low Rise (1-3)
Building Design: Low Rise (1-3 Floors)
Community Type: Gated, Golf Course
MLS Area: The Hideaway Country Club
Total Square Footage: 1,436
Total Floors: 1
Water: Assessment Paid
Construction: Concrete Block, Stucco
Date Listed: 2026-05-06 00:00:00
Pool Description: Community
Furnished: Negotiable
Windows: Window Coverings
Parking: 1 Assigned, Covered, Golf Cart, Guest, Paved, Detached Carport
Roof: Shingle
Heating: Central Electric
Cooling: Ceiling Fan(S), Central Electric
Storm Protection: Impact Resistant Windows
Security: Smoke Detector(S), Gated Community
Laundry: Washer/ Dryer Hookup, Laundry In Residence
Irrigation: Central
Pets: Limits
Restrictions: No Commercial, No R V
Maintenance: Cable, Insurance, Internet/ Wi Fi Access, Lawn/ Land Maintenance, Legal/ Accounting, Pest Control Exterior, Rec Facilities, Reserve, Street Lights, Street Maintenance
Rear Exposure: E
Lot Desc.: Golf Course
Amenities: Clubhouse, Pool, Community Room, Fitness Center, Storage, Golf Course, Internet Access, Putting Green, Restaurant, Streetlight, Tennis Court(S), Car Wash Area
Map of 5950 Trailwinds Dr #222, Fort Myers, FL 33907
Listing Courtesy Of: Realty One Group Mvp
homesbychrisjackson@gmail.com