5925 Trailwinds Dr #925, photo 1
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Overview

3 bd2 ba1,435 sqftCondominium
TypeCondominium
HOA$1,632/qtr
Built1989
Lot8,614 sqft
Living area1,435 sqft
Price / sqft$73

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

Ceiling Fans(s)Eat-in KitchenLiving Room/Dining Room ComboOpen FloorplanSplit BedroomVaulted Ceiling(s)Walk-in Closet(s)Window Treatments

5925 Trailwinds Dr #925 is a 1989-built home in Oakmont Village Condo, Fort Myers. Inside you'll find 3 bedrooms, 2 bathrooms, and 1,435 square feet of living space. Listed at $105,000 (about $73/sqft), 37 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $1,632 quarterly.

From the listing

AGENTS - PLEASE VIEW REALTOR REMARKS IN THE MLS. Wake up to peaceful water and golf course views from this beautifully maintained second floor condo in Oakmont Village at The Hideaway Country Club. Featuring 3 bedrooms and 2 bathrooms, this bright and spacious residence provides a comfortable layout filled with natural light and inviting Florida charm. The open living and dining area features a vaulted ceiling, neutral finishes, tile flooring, ceiling fans, and large sliding glass doors that showcase the scenic surroundings. The kitchen provides abundant cabinet and counter space, a breakfast bar, appliances, and an open connection to the main living area. The spacious primary bedroom includes a ceiling fan, generous closet space, and convenient access to a private bathroom with an extended vanity and walk in shower. The additional bedroom is bright and comfortably sized, guest area, reading room, or hobby space. An interior laundry area adds everyday convenience. Step through the sliding glass doors onto the private screened lanai and enjoy relaxing views of the landscaped grounds, and golf course. Whether enjoying a quiet morning or unwinding at the end of the day, this outdoor space is a standout feature of the home. Additional highlights include covered assigned parking, a community pool, maintained tropical landscaping, and a gated golf community setting. Conveniently located near shopping, dining, entertainment, major roadways, the airport, and Southwest Florida beaches, this condo combines comfort, scenery, and convenience. Clean, welcoming, and ready for its next owner, this property is a wonderful choice for a primary residence, seasonal getaway, or investment opportunity. Schedule your private showing and experience everything this Fort Myers condo provides! Offers may be entered ONLINE through Tuesday, October 20, 2026 at 5:00 pm. AT SELLER'S DISCRETION, A SUBMISSION MAY BE ACCEPTED AT ANY TIME.

The essentials

Built
1989
Price / sqft
$73
On market
37 days
Annual tax
$1,241
HOA
$1,632/qtr
Flood zone
X · Low risk
Lot
8,614 sqft
Type
Condominium

At a glance

Condo
Built 1989
Waterfront
Lake Front
Community pool
Fitness center too
Private balcony
Outdoor space
1,435 sqft
Living area

Payment

Est. monthly payment
$1,248/mo
Down payment (20%)
$21,000
Property taxes
$103/mo
HOA
$1,632/qtr
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Condominium
Year Built
1989
Lot
8,614 sqft
Cooling
Central Air
Heating
Electric
Parking
-
Waterfront
Lake Front
Days on Market
37
Ceiling Fans(s)
Eat-in Kitchen
Living Room/Dining Room Combo
Open Floorplan
Split Bedroom
Vaulted Ceiling(s)
Walk-in Closet(s)
Window Treatments
Balcony
Lighting
Sidewalk
Storage
Buyer Approval Required
Clubhouse
Community Mailbox
Deed Restrictions
Fitness Center
Gated Community - Guard
Golf Carts OK
Golf
Irrigation-reclaimed Water
No Truck/Rv/Motorcycle Parking
Pool
Restaurant
Sidewalks
Tennis Court(s)
Convection Oven
Dishwasher
Dryer
Microwave
Refrigerator
Washer
Elementary
Villas Elementary
Middle
Cypress Lake Middle School
High
Fort Myers High School

Districts can re-zone, so verify directly with the district before relying on these.

Homestead exemption on file Flood Zone X
Annual Tax (2025)
$1,241
Parcel #
12-45-24-28-00000.9250

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Oakmont Village Condo
County
Lee
MLS Area
33907 - Fort Myers
Lot Size
8,614 sqft
HOA
$1,632/qtr
Oakmont Village

Price history

Date
Event
Price
9/24/2026
Price change
Source: Stellar MLS #TB8545518
$105,000-41.0%
$73/sqft
-
Price change
Source: Stellar MLS #TB8545518
$178,000-0.6%
$124/sqft
9/3/2026
Listed for sale
Source: Stellar MLS #TB8545518
$179,000
$125/sqft

Neighborhood

5925 Trailwinds Dr #925
Fort Myers, FL, 33907 · 33907 - Fort Myers

Market insights

Offer Insights

Choose an offer strength

List price: $105,000
$103,000 – $105,000
97.8% – 100% of listTops out right at the list price
80% of listList price
11 of the last 20 condo closings in Fort Myers landed at this number or higher (55%). The median one sat 81 days before it went under contract, and this one is on day 37 after a $74,000 cut.

Sample: 20 closed condo sales in Fort Myers over the last 8 months, Stellar MLS. Widened past this ZIP to get a usable sample. A small sample in a thin market. A starting point, not a guarantee.

Talk through an offer with our team

Calculator

Est. monthly payment
$1,248/mo
Principal & interest$548
Property taxes$103
Insurance$53
HOA$544
Down payment20% · $21,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. HOA is the fee reported on the listing. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$105,000

$73 per sq ft

Beds and baths

3 beds, 2 baths

Size

1,435 sq ft

Time on market

37 days

Year built

1989

Monthly payment

About $1,248/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $1,241 annual tax bill, insurance, and the $1,632/qtr HOA fee.

HOA fee

$1,632/qtr

Managed by Oakmont Village.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

What should I offer?

Have another question?

Brokered byDIVINE ESTATES REALTY LLCListing agent: Eman HelalyListing data from Stellar MLS, MLS# TB8545518.

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