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5950 Trailwinds Drive Fort Myers FL 33907

$279,900
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5950 Trailwinds Drive, Fort Myers, FL 33907 - MLS#226017663 5950 Trailwinds Drive, Fort Myers, FL 33907 - MLS#226017663 5950 Trailwinds Drive, Fort Myers, FL 33907 - MLS#226017663 5950 Trailwinds Drive, Fort Myers, FL 33907 - MLS#226017663

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
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Overview of 5950 Trailwinds Dr 222

3 Bedrooms
2 Bathrooms
0 Car Garage
1,436 Square Feet
1,436SF Living Area
Pool:
No
Water: None
Year Built 1988
Listed For 0 Days

Don't miss this condo for sale in The Hideaway Country Club! 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.

This lovely condo was built in 1988 and features 3 bedrooms, and 2 full bathrooms. This condo for sale is 1,436 square feet, with 1,436 sq ft being air conditioned living space. The condo does not have a private swimming pool, although there is a community pool in the complex for use by residents.

Directions to this property are as follows: 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.

Please contact your ZFC agent for more information about MLS# 226017663 or any other condos for sale in Fort Myers or elsewhere in the Lee County area.

Features & Amenities

Appliances

Cooktop, Dryer, Dishwasher, Disposal, Microwave, Range, Refrigerator, Self Cleaning Oven, Washer

Architecture

Two Story, Low Rise

Cooling

Central Air, Ceiling Fans, Electric

Heating

Central, Electric

Flooring

Other

Parking

Assigned, Covered, Golf Cart Garage, Guest, Paved, One Space, Detached Carport

Lot Size

Acres

View

Golf Course, Pond view

Construction Materials

Block, Concrete, Stucco

Security Features

Security Gate, Gated Community, Smoke Detectors

Interior Features

Breakfast Bar, Dual Sinks, High Ceilings, Living Dining Room, Shower Only, Separate Shower, Cable Tv, Walk In Closets, Window Treatments, High Speed Internet, Split Bedrooms

Furnished

Negotiable

Exterior Features

Outdoor Grill, Patio

Lot Features

On Golf Course, Pond On Lot

Property Condition

Resale

Patio And Porch Features

Patio

Pool Features

Community

Roof

Shingle

Window Features

Impact Glass, Window Coverings

Utilities

Cable Available, High Speed Internet Available

Waterfront Features

None

Irrigation Source

Municipal

Laundry

Washer Hookup, Dryer Hookup, Inside

Number Of Stories

2

Year Built

1988

Pets Allowed

Call, Conditional

Annual Real Estate Taxes

$1,727 (2025)

Legal Description

Greenbriar Village Or 1966 Pg 3038 Bldg 2 Unit 222

Property Type

Condominium

HOA Fees

$5,325 /Annually

Other Association Fee

$1,242 /Quarterly

Association Fee Includes

Cable Tv, Insurance, Internet, Legal Accounting, Maintenance Grounds, Pest Control, Recreation Facilities, Reserve Fund, Road Maintenance, Street Lights

Association Amenities

Clubhouse, Fitness Center, Golf Course, Pool, Putting Greens, Restaurant, Storage, Tennis Courts, Vehicle Wash Area, Management

Community Features

Golf, Gated, Street Lights

Direction Faces

West

MLS Number

226017663

Universal Property Id

U S-12071-N-12452427000022220-R-N

Community Name

Greenbriar Village

Property Manager

(330) 550-1170

5950 Trailwinds Dr Price Calculator

Get Mortgage Quote For This Condo

The payment calculator figures for 5950 Trailwinds Dr 222 should be used as an estimate only. Loan terms including interest rate, and required downpayment will vary with each lender and/or individual. RE taxes for this condo for sale are estimated based on the actual property taxes for this property for the tax year 2025 which are $1,727 but will likely change when this condo sells. These estimations are calculated from a list price of $279,900 and a 25% down payment and do not include homeowners insurance which will vary greatly depending on the condo characteristics and location.

Recent Condo Sales near 5950 Trailwinds Dr

Address Sale Price Bed Bth Size Location Sale Date
5910 Trailwinds DR 422 $Log in to view 3 2/0 1,425SF Greenbriar Village 03/02/2026
5830 Trailwinds DR 813 $Log in to view 3 2/0 1,099SF Greenbriar Village 12/31/2025
5810 Trailwinds DR 912 $Log in to view 2 2/0 813SF Greenbriar Village 03/25/2026
5870 Trailwinds DR 614 $Log in to view 2 2/0 813SF Greenbriar Village 10/22/2025
1608 Park Meadows DR 1 $Log in to view 3 2/1 1,758SF Parkwoods 06/10/2025
13891 Lake Mahogany BLVD 3123 $Log in to view 3 2/0 1,749SF Reflection Lakes 08/19/2025
13911 Lake Mahogany BLVD 2922 $Log in to view 3 2/0 1,749SF Reflection Lakes 07/17/2025
13831 Lake Mahogany BLVD 3723 $Log in to view 3 2/0 1,736SF Reflection Lakes 01/20/2026
113 Pinebrook DR $Log in to view 3 2/0 1,634SF Pinebrook 05/13/2025
5348 Governors DR $Log in to view 3 2/0 1,578SF Pinebrook 10/03/2025
13991 Lake Mahogany BLVD 2413 $Log in to view 3 2/0 1,496SF Reflection Lakes 05/16/2025
5865 Trailwinds DR 623 $Log in to view 3 2/0 1,435SF Oakmont Village 12/30/2025

MLS# 226017663 Listing History

05/06/2026 Listed for sale by Realty One Group MVP with MLS# 226017663 with a list price of $279,900.

Lee County Schools

Elementary School

Middle School

Public Transportation

Lee County Transit:

SFMT to Edison Mal

Lee County Transit:

SFMT to Edison Mal

Lee County Transit:

SFMT to Edison Mal

Lee County Transit:

SFMT to Edison Mal

Lee County Transit:

SFMT to Edison Mal

This listing of 5950 Trailwinds Dr Fort Myers FL 33907 was last updated on 2026-05-06 10:00:33. Listing courtesy of Realty One Group MVP.
MLS

Map of 5950 Trailwinds Dr Fort Myers FL 33907

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Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
Call Me
Text Me
Email Me
When clicking Submit Request, you are registering to this website and agreeing that ZFC Real Estate, its affiliates or associated third parties may contact you, including with calls or texts by automated means. You also agree to our Terms of Use and Privacy Policy

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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