5925 TRAILWINDS DRIVE UNIT 925, FORT MYERS, FL, 33907
Active17 days on marketListed Sep 3, 2026MLS #TB8545518
About this home
5925 TRAILWINDS DRIVE UNIT 925
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, while the separate den provides flexible space for a home office, 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!
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,435
Sqft
0.2 ac
Lot size
1989
Year built
One
Levels
$124
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record and the real association fee — not generic estimates.
$1,934 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$1,934/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
$/sqft vs Fort Myers actives
$124 vs $207
Days on market
17 vs 41 typical
Where $124/sqft sits among the 130 Fort Myers actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside The Hideaway Country Club
Get to know Fort Myers. See the full Fort Myers guide →
The Hideaway Country Club — neighborhood snapshot
Population
609
Median age
49
Median income
$61,357
Median home value
$192,285
Avg household
3
Households w/ children
92%
For the school run
Lee County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Fort Myers market
$325K → $317K
Fort Myers median sold, yr/yr
95.9%
Sale-to-list ratio (12 mo)
61 of 130
Fort Myers actives have cut their price
Median sold price, Fort Myers, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 7% below the FORT MYERS 33907 median. See the full Fort Myers market guide →
Paper trail
This home's history
Reality check
What actually sold near 5925 TRAILWINDS DRIVE UNIT 925
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Nov ’25$295,000
2207 WOODLAND BOULEVARD
3 bd · 2 ba · 1,350 sqft · $219/sqft · 89 DOM
Sold · Jan ’26$370,000
2451 JASPER AVENUE
3 bd · 2 ba · 1,578 sqft · $234/sqft · 0 DOM
Sold · Aug ’26$359,000
11655 SOLANO DRIVE
2 bd · 2 ba · 1,632 sqft · $220/sqft · 170 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Shawn Headley
Realtor · CENTURY 21 Edge
Tours, negotiation, and every question about 5925 TRAILWINDS DRIVE UNIT 925 — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 5925 TRAILWINDS DRIVE UNIT 925 — before you fall in love.
See it in person
Schedule a tour
Live availability from Shawn's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
5925 TRAILWINDS DRIVE UNIT 925 FAQs
What would the monthly payment be for 5925 TRAILWINDS DRIVE UNIT 925?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $1,934/mo — principal and interest, the actual property-tax bill, the $544/mo association fee and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
How much are the HOA fees at 5925 TRAILWINDS DRIVE UNIT 925?+
The association fee works out to $544 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 5925 TRAILWINDS DRIVE UNIT 925?+
The most recent tax bill on record (2025) was $1,241. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 5925 TRAILWINDS DRIVE UNIT 925?+
The listing reports pets: Cats OK, Dogs OK, Number Limit, Size Limit, Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Fort Myers?+
At $178,000, this home is listed about 49% below the Fort Myers median of $350,000. The market section on this page shows how the area is trending.
Which schools are assigned to 5925 TRAILWINDS DRIVE UNIT 925?+
Villas Elementary School (elementary), Tanglewood Elementary School (elementary), South Fort Myers High School (high), Cypress Lake Middle School (middle), Cypress Lake High School (high), Fort Myers High School (high), Dunbar High School (high), Heights Elementary School (elementary), Rayma C. Page Elementary School (elementary), Lexington Middle School (middle), San Carlos Park Elementary School (elementary), Three Oaks Middle School (middle), Three Oaks Elementary School (elementary) — Lee County School District. Always verify school assignments with the district before relying on them.
The brief
Five things that matter here
01Under the FORT MYERS 33907 market on paper
$178,000 is 7% below the FORT MYERS 33907 median of $191,450, and at $124/sqft it sits under the Fort Myers average of $251.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Know the monthly fee
The association fee is $544/mo. That usually buys real services — verify what's covered before comparing this home against fee-free alternatives.
04Strong assigned schools
Villas Elementary School, Tanglewood Elementary School, South Fort Myers High School, Cypress Lake Middle School, Cypress Lake High School, Fort Myers High School, Dunbar High School, Heights Elementary School, Rayma C. Page Elementary School, Lexington Middle School, San Carlos Park Elementary School, Three Oaks Middle School, Three Oaks Elementary School — Cypress Lake Middle School rates 4 of 5. Always verify assignments with the district.
05The price has already moved
Listed at $179,000, now $178,000 — a $1K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of DIVINE ESTATES REALTY LLC · Eman Helaly. MLS #TB8545518.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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