5905 Trailwinds Dr, Unit 816

$194,900
Price
3
Beds
1,330 Sq. Ft.
$147 / Sq. Ft.
1,330
Sq. Ft.
$147
per Sq. Ft.

Description

Welcome to 5905 Trailwinds Dr. #816 — a rare first-floor end unit in Oakmont Village, offering unbeatable value and breathtaking lake and golf course views. This spacious 3-bedroom, 2-bath condo is just steps from the sparkling village pool and patio, making it perfect for both relaxation and socializing. Inside, you’ll find low-maintenance laminate and tile flooring throughout (no carpet!) , a beautifully updated guest bath, and an air-conditioned Florida Room that expands your living space year-round....Welcome to 5905 Trailwinds Dr. #816 — a rare first-floor end unit in Oakmont Village, offering unbeatable value and breathtaking lake and golf course views. This spacious 3-bedroom, 2-bath condo is just steps from the sparkling village pool and patio, making it perfect for both relaxation and socializing. Inside, you’ll find low-maintenance laminate and tile flooring throughout (no carpet!) , a beautifully updated guest bath, and an air-conditioned Florida Room that expands your living space year-round. Enjoy your morning coffee while watching the sunrise over the fairway, or unwind in the evenings with tranquil water views. Additional perks include a private outside storage closet and a dedicated golf cart parking space. The Hideaway Country Club offers optional memberships for golf and tennis, plus a clubhouse and on-site dining for all residents. Centrally located in the heart of Fort Myers, this home is close to shopping, dining, and the best of Southwest Florida living. Don’t miss your chance to own the most affordable 3-bedroom in this sought-after community! Realtors please see remarks!

Property Details for 5905 Trailwinds Drive, Unit 816

Development
THE HIDEAWAY COUNTRY CLUB
Building Design
Low Rise (1-3)
Community Type
Gated, Golf Course, Tennis
Waterfront
Yes
Waterfront Desc
Lake
Waterfront Desc
Lake
View
Golf, Landscaped Area, Lake
Garage Spaces
.00
LISTING UPDATED: 12/10/2025 12:56 PM

Property Details for 5905 Trailwinds Drive, Unit 816

StatusActive
MLS #2025005046
Days on Market125
Taxes$2,569 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeCondo
MLS TypeResidential / Condo
Year Built1990
CountyLee County

Location

Listing Courtesy of Keller Williams Realty Fort Myers and the Islands, Jessica Steinberg
Add your commute

Building Information for 5905 Trailwinds Drive, Unit 816

Building/Complex5905 Trailwinds DrFloor1Stories1Residences18Pet PolicyAllowedPet Policy DetailsCall,ConditionalYear Built1990

Payment Calculator

$1,177 per month

30 year fixed, 6.28% Interest

Principal and Interest

$963

Property Taxes

$214

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 5905 Trailwinds Drive, Unit 816

Summary
Location and General Information
  • City: Fort Myers
  • Elementary School: PROXIMITY
  • High School: PROXIMITY
  • Human Modified: Yes
  • Latitude: 26.57
  • Longitude: -81.86
  • Middle School: PROXIITY
  • MLS Area Major: FM07 - Fort Myers Area
  • Pets: Limits, With Approval
  • Postal Code: 33907
  • Road Surface Type: Paved
  • Street Name: Trailwinds
  • Street Number: 5905
  • Street Suffix: DR
  • Unit Number: 816
  • Full Address: 5905 Trailwinds DR 816
  • View: Yes
Parking
  • Carport Spaces: 1.00
  • Carport: Yes
  • Covered Spaces: 1.00
  • Garage: No
  • Parking Features: Assigned, Covered, Golf Cart Garage, One Space, Detached Carport
Taxes and HOA Information
  • Amenity Rec Fee: $.00
  • Application Fee: $225.00
  • Association Fee Total: $14,691.00
  • Association Fee Total Frequency: Annually
  • Association Fee 2: $.00
  • Primary HOA Fee Freq: Annually
  • Maintenance: Cable Tv, Internet, Irrigation Water, Maintenance Grounds, Pest Control, Recreation Facilities, Reserve Fund, Road Maintenance, Sewer, Street Lights, Trash, Water
  • Association Mngmt Phone: (239) 461-8700
  • Mandatory HOA: Yes
  • HOA Desc: Mandatory
  • Tax Annual Amount: $2,568.69
  • Tax Year: 2024
  • Transfer Fee: $6,000.00
  • 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: 12-45-24-28-00000.8160
  • Property Type: Residential
  • Section: 12
  • Lot Unit: 816
  • Source of Measure Living Area: Appraiser
  • Source of Measure Lot Dimensions: Appraiser
  • Lot Desc: Zero Lot Line
  • Source of Measurements: Appraiser
  • Lot Size Units: Acres
  • Legal Desc: OAKMONT VILLAGE CONDO NO.8 OR 2190 PG 4277 UNIT 816
Property and Assessments
  • Total Area: 1330.0
  • Rear Exposure: E
  • Approx Living Area: 1330.0
  • 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: Deed Restrictions, No Commercial, No Motorcycles, No Rv
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: 1
  • Golf Type: Golf Non Equity
  • Annual Food And Beverage Minimum: 600.00
  • Units in Complex: 152
  • Total Floors: 1
  • Total One Time Fees: $6,225.00
  • Units in Building: 18
  • Unit Location: 1
Interior and Exterior Features
Exterior Features
  • Architectural Style: Other, Low Rise
  • Association Amenities: Clubhouse, Fitness Center, Golf Course, Barbecue, Picnic Area, Pickleball, Pool, Putting Greens, Restaurant, Storage, Sidewalks, Tennis Courts, Vehicle Wash Area, Management
  • Canal Width: N, o, n, e
  • Community Features: Elevator, Golf, Gated, Tennis Courts, Street Lights
  • Construction: Poured Concrete, Concrete Block
  • Exterior Features: None
  • Exterior Features: None
  • Irrigation Source: Other
  • 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, Washer
  • Baths Full: 2
  • Bathrooms Half: 0
  • Bathrooms Total Integer: 2.0
  • Beds Total: 3
  • Bedrooms: 3 Bed
  • Cooling: Central Air, Electric
  • Cooling: Yes
  • Elevator Text Details: Common
  • Flooring: Laminate, Tile
  • Furnished Desc: Furnished
  • Heating: Central, Electric
  • Heating: Yes
  • Interior Features: Breakfast Bar, Built In Features, Bedroom On Main Level, Dual Sinks, Living Dining Room, Main Level Primary, Pantry, Shower Only, Separate Shower, Walk In Closets, Window Treatments
  • Interior Features: Pantry, Walk-In Closet, Smoke Detectors, Window Coverings
  • Laundry Features: Washer Hookup, Dryer Hookup, Inside
  • Rooms Total: 0
  • Window Features: Single Hung, Window Coverings
Rental
Rental Information
  • One Time Rec Lease Fee: $.00

Property History for 5905 Trailwinds Drive, Unit 816

DateEvent & SourcePriceAppreciation
Aug 8, 2025

Listed (Active)

FORTMLS #2025005046

$194,900—
May 30, 2025

Withdrawn

FORTMLS #224053919

$199,900—
Mar 11, 2025

Price Change

FORTMLS #224053919

$209,900—
Jan 31, 2025

Price Change

FORTMLS #224053919

$219,900—
Dec 17, 2024

Price Change

FORTMLS #224053919

$229,900—
Nov 8, 2024

Price Change

FORTMLS #224053919

$239,900—
Oct 14, 2024

Price Change

FORTMLS #224053919

$249,900—
Jul 22, 2024

Price Change

FORTMLS #224053919

$259,900—
Jul 10, 2024

Price Change

FORTMLS #224053919

$269,900—
Jun 25, 2024

Listed (Active)

FORTMLS #224053919

$279,900—
DateEvent & SourcePrice
08/08/2025

Listed (Active)

FORTMLS #2025005046

$194,900
05/30/2025

Withdrawn

FORTMLS #224053919

$199,900
03/11/2025

Price Change

FORTMLS #224053919

$209,900
01/31/2025

Price Change

FORTMLS #224053919

$219,900
12/17/2024

Price Change

FORTMLS #224053919

$229,900
11/08/2024

Price Change

FORTMLS #224053919

$239,900
10/14/2024

Price Change

FORTMLS #224053919

$249,900
07/22/2024

Price Change

FORTMLS #224053919

$259,900
07/10/2024

Price Change

FORTMLS #224053919

$269,900
06/25/2024

Listed (Active)

FORTMLS #224053919

$279,900

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

Public Records for 5905 Trailwinds Drive, Unit 816

Taxable ValueLand-Additions$238,788Total-
Tax Record2024$2,569 ($214 / month)
Home Facts
Beds3Total Finished SqFt1,193 SqFtAbove Grade Finished SqFt1,193 SqFtStories3Lot Size8,295 SqFtStyleCondominiumYear Built1990CountyLEEAPN12-45-24-28-00000.8160

Schools near 5905 Trailwinds Drive, Unit 816

This home is within School District of Lee County.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - PK to 5
Public - PK to 5
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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5905 Trailwinds Drive, Unit 816 is a condo for sale in Fort Myers, FL 33907. This property was listed for sale on August 8, 2025 by Keller Williams Realty Fort Myers and the Islands, it's currently listed at $194,900. 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 816 is a 3-bed, 2-bath, 1,330 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. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Keller Williams Realty Fort Myers and the Islands, Jessica Steinberg

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.