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$279,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,436 Sq. Ft.
  • Updated 5 days ago
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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.

Full Property Details for 5950 Trailwinds Dr #222

General

  • Price: $279,900
  • HOA FEE: $414/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $1,727 (2025)
  • Status: Active
  • Type: Single Family
  • Source: Bonita_Springs
  • MLS ID: 226017663
  • Updated: 5/6/2026
  • Added to Site: 6 day(s) ago

Rental Information

  • Lease/Rent Term: 30
  • Min. Lease (Days): 30

Interior

  • Interior Features: Split Bedrooms, Wired for Data, Volume Ceiling, Walk-In Closet(s)
  • Appliances: Cooktop, Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Self-Cleaning Oven, Washer
  • Furnishings: Negotiable
  • Flooring: Other

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Primary Bathroom: Dual Sinks, Shower Only

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Dining Room: Breakfast Bar, Dining - Living
  • Laundry: Washer/Dryer Hookup, Inside

Additional Information

  • Shared Amenities: Golf Non Equity, Clubhouse, Pool, Community Room, Fitness Center, Extra Storage, Golf, Internet Access, Putting Green, Restaurant, Street Lights, Tennis Court(s), Vehicle Wash Area, Gated, Golf Course
  • Tennis: Yes
  • Security/Safety: Safe, Smoke Detector(s), Smoke Detectors

Exterior

  • Porch/Patio/Deck: Patio

Parking

  • Carports: Yes
  • Carport Spaces: 1
  • Covered Spaces: 1
  • Parking Features: 1 Assigned, Covered, Golf Cart Garage, Guest, Paved, Detached Carport

Location

  • Area: FM07 - Fort Myers Area
  • County: Lee
  • Subdivision: GREENBRIAR VILLAGE
  • Building Name: THE HIDEAWAY COUNTRY CLUB
  • Driving Directions: Metro Pkwy or S Cleveland Ave. to Crystal Dr., N on Wooddale, E on Treehaven, N on New Pine Lake Rd, NE on Trailwinds Dr.- Follow straight to Bldg 5950 at the end of road
  • Direction Faces: West

Community

  • Association: Yes
  • Assoc. Fees Include: Cable TV, Insurance, Internet, Maintenance Grounds, Legal/Accounting, Pest Control Exterior, Rec Facilities, Reserve, Street Lights, Street Maintenance
  • Units Assoc/Comm: 496
  • Pets Allowed: Yes
  • Number of Pets: 2
  • Management Type: Professional

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Ceiling Fan(s), Central Electric
  • Heating Type: Central Electric
  • Ceiling Fan(s): 5

Utilities

  • Sewer: Assessment Paid
  • Water: Assessment Paid
  • Cable Available: Yes
  • Utility Description: Cable Available

Structural Information

  • Description/Design: Low Rise (1-3)
  • Exterior Const.: Concrete Block, Stucco
  • Roof: Shingle
  • Windows: Impact Resistant, Impact Resistant Windows, Window Coverings
  • Entry Floor Number: 2
  • Stories/Levels: 2
  • Stories in Building: 1
  • Square Feet: 1,436
  • Sq. Ft. Source: Developer Brochure
  • Living Area: 1,436 Sq. Ft.
  • Year Built: 1988

Lot Features

  • Property View: Golf Course, Pond
  • Lot Size (Acres): 0.1959
  • Lot Size (Sq. Ft.): 8,533
  • Lot Size Source: Condo Documents
  • Street/Road Desc.: Paved
  • Irrigation System: Central
  • Lot Features: On Golf Course
  • Lot Description: On Golf Course

Water Features

  • Water Front Desc.: None, Pond
  • Canal Width: None

Financial Considerations

  • Association Fee: $1,242
  • Assoc Fee Freq.: Quarterly
  • Other Assoc Fees: $5,325
  • Application Fee: $150
  • Other Fee Freq.: Annually
  • Tax Amount: $1,727
  • Tax Year: 2025
  • Terms: Buyer Finance/Cash

Disclosures and Reports

  • Ownership: Condo
  • Legal Description: GREENBRIAR VILLAGE OR 1966 PG 3038 BLDG 2 UNIT 222
  • Property ID: 12-45-24-27-00002.2220
  • Section: 12
  • Block: 2
  • Lot Number: 222

Listed by Realty One Group MVP

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— 5950 Trailwinds Dr #222 —

  • Realty One Group MVP

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NMLS#: 1598647

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Be ready to buy your new home!

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NMLS#: 1598647

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Schools serving 5950 Trailwinds Dr #222

School District:Lee County School District, Fort Myers, FL
NameGradesDistance
Villas Elementary School
8385 Beacon Boulevard, Fort Myers, FL 33907
K-50.7 mi
Tanglewood Elementary School
1620 Manchester Boulevard, Fort Myers, FL 33919
K-51.7 mi
Heights Elementary School
15200 Alexandria Court, Fort Myers, FL 33908
K-55.5 mi
Cypress Lake Middle School
8901 Cypress Lake Drive, Fort Myers, FL 33919
6-83.3 mi
Lexington Middle School
16351 Summerlin Road, Fort Myers, FL 33908
6-86.2 mi
South Fort Myers High School
14020 Plantation Road, Fort Myers, FL 33912
9-122.3 mi
Cypress Lake High School
6750 Panther Lane, Fort Myers, FL 33919
9-123.5 mi
Fort Myers High School
2635 Cortez Boulevard, Fort Myers, FL 33901
9-124.1 mi
Rayma C. Page Elementary School
17000 South Tamiami Trail, Fort Myers, FL 33908
K-55.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5950 Trailwinds Dr #222 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/06/2026
Listed
$279,900
21.75%
MLS
8/26/2021
Sold
$229,900
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5950 Trailwinds Dr #222

Year
Property Taxes
Change
Tax Assessment
Change
2025
$1,746
4%
$169,349
3%
2024
$1,686
2%
$164,576
3%
2023
$1,645
2%
$159,783
41%
2021
$1,620
-7%
$113,019
-27%
2022
$1,736
7%
$155,129
44%
2021
$1,620
-14%
$107,398
-14%
2018
$1,878
1%
$124,355
-1%
2017
$1,861
6%
$125,163
7%
2016
$1,750
-4%
$117,164
-5%
2019
$1,832
18%
$123,548
29%
2015
$1,555
17%
$95,800
14%
2014
$1,332
100%
$84,100
-6%
2013
$667
—
$89,900
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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5950 Trailwinds Dr #222, Fort Myers, FL 33907 (MLS# 226017663) is a Single Family property with 3 bedrooms and 2 full bathrooms. 5950 Trailwinds Dr #222 is currently listed for $279,900 and was received on May 06, 2026. Want to learn more about 5950 Trailwinds Dr #222? Do you have questions about finding other Single Family real estate for sale in Fort Myers? You can browse all Fort Myers real estate or contact a Coldwell Banker agent to request more information.

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