5905 Trailwinds Dr, Unit 824

Fort Myers, FL 33907

$249,000
Price
2
Beds
1,100 Sq. Ft.
$226 / Sq. Ft.
1,100
Sq. Ft.
$226
per Sq. Ft.
a view of a car park from a balcony
a view of a cars park in front of a building
a view of a dining room with furniture window and outside view
a view of a hallway with a glass door and a window
a view of hallway with stairs
a view of a hallway and a livingroom with furniture
a bedroom with a bed and a chandelier
a bedroom with a bed and a window
a bathroom with a sink a toilet a mirror a bathtub and shower
a spacious bedroom with a large bed and a window
a bedroom with bed and a chandelier
a bedroom with a bed and a flat screen tv
a living room with furniture and a table
a kitchen with a sink and chandelier
a bathroom with a toilet and a shower
a bathroom with a sink and a mirror
a bathroom with a bathtub and a sink
a view of a workspace with furniture and wooden floor
a living room with furniture and a large window
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture window and wooden floor
a living room with furniture a floor to ceiling window and wooden floor
a living room with furniture and wooden floor
a living room with furniture and a view of kitchen
a living room with furniture and kitchen view
a living room with furniture a rug and a chandelier
a living room with furniture fireplace and large windows
a living room with furniture and a large window
a dining room with furniture a chandelier and wooden floor
a view of a kitchen and dining room
a view of a dining room with furniture and chandelier
a view of a dining room with furniture
a view of a dining room with furniture window and outside view
a kitchen with stainless steel appliances a refrigerator sink and microwave
a kitchen with stainless steel appliances granite countertop a sink and stove top oven
a kitchen with stainless steel appliances granite countertop a refrigerator a stove top oven a sink and dishwasher
a utility room with dryer and washer
a front view of a house with a yard
a view of a lake with a yard
a view of a roof deck with furniture
a view of a roof deck with couches and city view
a view of a room with gym equipment
a view of a dining room with furniture
a outdoor dining with lots of furniture and white walls
a view of a dining room with furniture
a view of a room with lots of stuff and hardwood floor
a view of a tennis court
a view of a street
a view of a chairs and table in patio
a view of a swimming pool with a table and chairs under an umbrella

Description

Welcome to luxury living at The Hideaway Country Club! Tucked away in a peaceful and beautifully maintained community, this stunning 2-bedroom, 2-bathroom condo offers a perfect blend of elegance, comfort, and convenience. Located on the second floor, this bright and airy residence welcomes you with an abundance of natural light and sweeping views of the golf course and water. Situated right off one of the community’s few elevators—and in one of the only pet-friendly buildings—this unit offers exceptional...Welcome to luxury living at The Hideaway Country Club! Tucked away in a peaceful and beautifully maintained community, this stunning 2-bedroom, 2-bathroom condo offers a perfect blend of elegance, comfort, and convenience. Located on the second floor, this bright and airy residence welcomes you with an abundance of natural light and sweeping views of the golf course and water. Situated right off one of the community’s few elevators—and in one of the only pet-friendly buildings—this unit offers exceptional accessibility and ease. At the heart of the home is a fully updated kitchen designed to impress any culinary enthusiast. With sleek granite countertops, a stylish backsplash, and stainless-steel appliances, this space is both functional and beautiful. Offered turnkey, this move-in-ready retreat allows you to settle in effortlessly—just bring your clothes and toothbrush. A sparkling pool is just steps away, inviting you to enjoy a refreshing swim whenever you please. Living at The Hideaway Country Club means more than owning a home—it’s embracing a lifestyle. Separate golf and tennis memberships are available for active residents, while a fitness center, pickleball courts, card/social room, and a fantastic on-site restaurant provide endless opportunities for leisure and connection. Don’t miss your chance to experience resort-style living in one of Fort Myers’ most sought-after communities. Schedule your private showing today and discover the unmatched charm of this exceptional condo.

Property Details for 5905 Trailwinds Drive, Unit 824

Development
THE HIDEAWAY COUNTRY CLUB
Building Design
Low Rise (1-3)
Community Type
Gated, Golf Course, Tennis
Waterfront
No
Waterfront Desc
None
Waterfront Desc
None
View
Golf, Lake
Garage Spaces
.00
LISTING UPDATED: 12/08/2025 05:44 PM

Property Details for 5905 Trailwinds Drive, Unit 824

StatusActive
MLS #2025014529
Days on Market62
Taxes$2,851 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeCondo
MLS TypeResidential / Condo
Year Built1990
CountyLee County

Location

Listing Courtesy of Treeline Realty Corp, Jenn Swartz; Treeline Realty Corp, Jenna Scharf
Add your commute

Building Information for 5905 Trailwinds Drive, Unit 824

Building/Complex5905 Trailwinds DrFloor2Stories3Residences12Pet PolicyAllowedPet Policy DetailsCall,ConditionalYear Built1990

Payment Calculator

$1,468 per month

30 year fixed, 6.28% Interest

Principal and Interest

$1,230

Property Taxes

$238

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 5905 Trailwinds Drive, Unit 824

Summary
Location and General Information
  • City: Fort Myers
  • Directions: From 41 Turn onto Crystal Dr, Left on Beacon, Right on Trailwinds Dr. Virtual gate guard,give your name and name of your brokerage.
  • Human Modified: Yes
  • Latitude: 26.57
  • Longitude: -81.86
  • MLS Area Major: FM07 - Fort Myers Area
  • Pets: Limits, With Approval
  • Postal Code: 33907
  • Street Name: Trailwinds
  • Street Number: 5905
  • Street Suffix: DR
  • Block: 0
  • Unit Number: 824
  • Full Address: 5905 Trailwinds DR 824
  • View: Yes
Parking
  • Carport Spaces: 1.00
  • Carport: Yes
  • Covered Spaces: 1.00
  • Garage: No
  • Parking Features: Detached Carport
Taxes and HOA Information
  • Amenity Rec Fee: $.00
  • Application Fee: $225.00
  • Association Fee Total: $14,036.00
  • Association Fee Total Frequency: Annually
  • Association Fee 2: $.00
  • Primary HOA Fee Freq: Annually
  • Maintenance: Cable Tv, Insurance, Irrigation Water, Maintenance Grounds, Pest Control, Reserve Fund, Street Lights, Trash, Water
  • Association Mngmt Phone: (239)461-8700
  • Mandatory HOA: Yes
  • Tax Annual Amount: $2,851.36
  • Tax Year: 2024
  • Transfer Fee: $3,500.00
  • Association Fee 3: $2,234.00
  • Association Fee 3 Frequency: Quarterly
Property
Lot Information
  • Source of Measure Total Area: Appraiser
  • Development Name: THE HIDEAWAY COUNTRY CLUB
  • Parcel Number: 12-45-24-28-00000.8240
  • Property Type: Residential
  • Section: 12
  • Lot Unit: 824
  • Source of Measure Living Area: Appraiser
  • Source of Measure Lot Dimensions: Appraiser
  • Lot Desc: Zero Lot Line, Sprinklers Automatic
  • Acres: 0.1908
  • Lot Size Area: 0.1908
  • Source of Measurements: Appraiser
  • Lot Size Units: Acres
  • Legal Desc: OAKMONT VILLAGE CONDO NO.8 OR 2190 PG 4277 UNIT 824
Property and Assessments
  • Total Area: 1100.0
  • Rear Exposure: E
  • Approx Living Area: 1100.0
  • Possession: Close Of Escrow
  • Property Condition: Resale
  • Property Sub Type: Condominium
  • Township: 45
  • Senior Community: false
  • Range: 24E
  • Special Assessment: 0.00
  • Sub Condo Name: OAKMONT VILLAGE
  • Year Built Numeric: 1990
  • Property Sub Type Additional: Condominium
  • Restrictions: Architectural, Deed Restrictions
Lease Information
  • Land Lease Fee: $.00
  • One Time Land Lease Fee: $.00
  • One Time Mandatory Club Fee: $.00
  • One Time Othe Fee: $.00
  • One Time Special Assessment Fee: $.00
Utilities
  • Sewer: Central
  • Utilities: Cable Available, High Speed Internet Available
  • Water Source: Public
  • Water: Central
Multi Family
Multi-Family Information
  • Common Interest: Condominium
  • Num Unit Floor: 2
  • Golf Type: Golf Non Equity
  • Annual Food And Beverage Minimum: 400.00
  • Units in Complex: 496
  • Total Floors: 3
  • Total One Time Fees: $3,725.00
  • Units in Building: 12
  • Unit Location: 2
Interior and Exterior Features
Exterior Features
  • Architectural Style: Other, Low Rise
  • Association Amenities: Clubhouse, Fitness Center, Golf Course, Barbecue, Picnic Area, Pickleball, Private Membership, Pool, Putting Greens, Restaurant, Storage, Sidewalks, Tennis Courts, Vehicle Wash Area, Management
  • Canal Width: None
  • Community Features: Elevator, Golf, Gated, Tennis Courts, Street Lights
  • Construction: Poured Concrete, Concrete Block
  • Exterior Features: Sprinkler Irrigation, Storage, Shutters Electric, Shutters Manual
  • Exterior Features: Storage, Sprinklers Auto
  • Irrigation Source: Municipal
  • Pool Features: Community
  • Private Pool: No
  • Roof: Shingle
  • Security Features: Security Gate, Gated Community, Smoke Detectors
  • Structure Type: Low Rise
  • Gulf Access: No
  • Spa: No
Interior Features
  • Appliances: Dryer, Dishwasher, Freezer, Disposal, Microwave, Range, Refrigerator, Self Cleaning Oven, Washer
  • Baths Full: 2
  • Bathrooms Half: 0
  • Bathrooms Total Integer: 2.0
  • Beds Total: 2
  • Bedrooms: 2 Bed
  • Cooling: Central Air, Ceiling Fans, Electric
  • Cooling: Yes
  • Elevator Text Details: Common
  • Flooring: Laminate, Tile
  • Furnished Desc: Furnished
  • Heating: Central, Electric
  • Heating: Yes
  • Interior Features: Living Dining Room, Pantry, Shower Only, Separate Shower, Cable Tv, Walk In Closets, Window Treatments, High Speed Internet
  • Interior Features: Pantry, Walk-In Closet, High Speed Available, Smoke Detectors, Window Coverings
  • Laundry Features: Inside
  • Rooms Total: 0
  • Window Features: Single Hung, Sliding, Window Coverings
Rental
Rental Information
  • One Time Rec Lease Fee: $.00

Property History for 5905 Trailwinds Drive, Unit 824

DateEvent & SourcePriceAppreciation
Oct 10, 2025

Listed (Active)

FORTMLS #2025014529

$249,000—
Apr 18, 2025

Expired

FORTMLS #224093697

$249,900—
Nov 19, 2024

Listed (Active)

FORTMLS #224093697

$265,000—
Sep 15, 2024

Expired

FORTMLS #224047965

$269,000—
Jun 1, 2024

Listed (Active)

FORTMLS #224047965

$269,000—
May 20, 2024

Withdrawn

FORTMLS #224021583

$274,900—
Mar 9, 2024

Listed (Active)

FORTMLS #224021583

$274,900—
May 12, 2021

Sold

FORTMLS #221026218

$172,000—
May 12, 2021

Pending

FORTMLS #221026218

—
Apr 9, 2021

Listed (Active)

FORTMLS #221026218

$169,750—
Mar 12, 2021

Sold (Public Record)

Public Record #1460062835

$172,000

+2.9% / yr

Apr 22, 2014

Sold (Public Record)

Public Record #415398306

$141,000

-0.5% / yr

Oct 30, 2013

Expired

FORTMLS #201309136

$137,000—
Jan 31, 2013

Expired

FORTMLS #201205499

$148,000—
Jan 31, 2012

Expired

FORTMLS #201103606

$159,000—
Jan 15, 2011

Expired

FORTMLS #201020466

$175,000—
Mar 1, 2005

Sold (Public Record)

Public Record #153541452

$147,500—
Sep 15, 1999

Expired

FORTMLS #60035962

$99,900—
Sep 15, 1999

Expired

FORTMLS #90035962

$99,900—
Mar 15, 1999

Listed (Active)

FORTMLS #60035962

$99,900—
DateEvent & SourcePrice
10/10/2025

Listed (Active)

FORTMLS #2025014529

$249,000
04/18/2025

Expired

FORTMLS #224093697

$249,900
11/19/2024

Listed (Active)

FORTMLS #224093697

$265,000
09/15/2024

Expired

FORTMLS #224047965

$269,000
06/01/2024

Listed (Active)

FORTMLS #224047965

$269,000
05/20/2024

Withdrawn

FORTMLS #224021583

$274,900
03/09/2024

Listed (Active)

FORTMLS #224021583

$274,900
05/12/2021

Sold

FORTMLS #221026218

$172,000
05/12/2021

Pending

FORTMLS #221026218

—
04/09/2021

Listed (Active)

FORTMLS #221026218

$169,750
03/12/2021

Sold (Public Record)

Public Record #1460062835

$172,000

+2.9% / yr

04/22/2014

Sold (Public Record)

Public Record #415398306

$141,000

-0.5% / yr

10/30/2013

Expired

FORTMLS #201309136

$137,000
01/31/2013

Expired

FORTMLS #201205499

$148,000
01/31/2012

Expired

FORTMLS #201103606

$159,000
01/15/2011

Expired

FORTMLS #201020466

$175,000
03/01/2005

Sold (Public Record)

Public Record #153541452

$147,500
09/15/1999

Expired

FORTMLS #60035962

$99,900
09/15/1999

Expired

FORTMLS #90035962

$99,900
03/15/1999

Listed (Active)

FORTMLS #60035962

$99,900

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 5905 Trailwinds Drive, Unit 824

Taxable ValueLand-Additions$215,251Total-
Tax Record2024$2,851 ($238 / month)
Home Facts
Beds2Total Finished SqFt1,098 SqFtAbove Grade Finished SqFt1,098 SqFtStories3Lot Size8,295 SqFtStyleCondominiumYear Built1990CountyLEEAPN12-45-24-28-00000.8240

Schools near 5905 Trailwinds Drive, Unit 824

This home is within School District of Lee County.
Rating
School
Type
Grades
Distance
Tanglewood Elementary School
Public - PK to 5
Orangewood Elementary School
Public - PK to 5
Colonial Elementary School
Public - PK to 5
Villas Elementary School
Public - PK to 5
Rating
School
Distance
Tanglewood Elementary School
PublicPK to 5

Orangewood Elementary School
PublicPK to 5

Colonial Elementary School
PublicPK to 5

Villas Elementary School
PublicPK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 5905 Trailwinds Drive, Unit 824, Fort Myers, FL 33907

5905 Trailwinds Drive, Unit 824 is a condo for sale in Fort Myers, FL 33907. This property was listed for sale on October 10, 2025 by Treeline Realty Corp, it's currently listed at $249,000. It has been on the market for a total of 62 days and was last sold on May 12, 2021. This listing's school district is School District of Lee County. Nearby schools include Tanglewood Elementary School, Orangewood Elementary School and Colonial Elementary School. 5905 Trailwinds Drive, Unit 824 is a 2-bed, 2-bath, 1,100 sqft condo built in 1990.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Treeline Realty Corp, Jenn Swartz; Treeline Realty Corp, Jenna Scharf

The information is being provided in part by Southwest Florida Multiple Listing Service, Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2, and MarcoMls. Information deemed reliable but not guaranteed. Information is provided for consumers' personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2025 Southwest Florida Multiple Listing Service and MarcoMls. All Rights Reserved. The data relating to real estate for sale displayed on this website comes in part from the Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2 and MarcoMls. Properties listed with brokerage firms other than Compass are marked with the "BR House" logo. Detailed information about such properties includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties listed with brokerage firms participating in the Naples MLS BR Program, or contained in the database compilation of Naples MLS.