Fort Myers, FL · Single-Family Neighborhoods (Non-Gated)
Trailwinds
Subdivision off Williams Ave
Market Snapshot
Trailwinds market data
Live from the MLS · updated continuously. See all 33 listings →
Figures reflect current active listings (and recent closed sales where available) tagged to Trailwinds. Medians are indicative, not an appraisal, ask Rick for a comparative market analysis on a specific home.
On the Map
Where Trailwinds sits
Available Now
Homes for sale in Trailwinds(33)
Newest listings first, showing 12 of 33.
- For SaleNew Today
$225,000
MLS# 20260356113 bd2 ba1,410 sqft8524 Dominican Court, Fort Myers, FL, 33907
- For SaleNew Today
$89,000
MLS# 2260296032 bd2 ba1,107 sqft2100 Barkeley Lane 1, Fort Myers, FL, 33907
- For SaleNew TodayPool
$430,000
MLS# 20260371783 bd2 ba1,464 sqft2230 Crystal Drive, Fort Myers, FL, 33907
- For SaleNew TodayWaterfront
$179,000
MLS# 20260379793 bd2 ba1,187 sqft5585 Trailwinds Drive 324, Fort Myers, FL, 33907
- For SaleNew Today
$159,999
MLS# 20260378011 bd1 ba1,068 sqft2111 Barkeley Lane 13, Fort Myers, FL, 33907
- For SaleNew Today
$269,900
MLS# 20260394782 bd1 ba1,091 sqft2124 Sunrise Boulevard, Fort Myers, FL, 33907
- For SaleNew This WeekPool
$199,900
MLS# 20260381993 bd2 ba1,738 sqft2215 Treehaven Circle, Fort Myers, FL, 33907
- For SaleNew This WeekPool
$480,000
MLS# 20260393255 bd3 ba2,800 sqft2212 Crystal Drive, Fort Myers, FL, 33907
- For SaleNew This WeekPool
$425,000
MLS# 20260383363 bd2 ba1,581 sqft2439 Ephraim Avenue, Fort Myers, FL, 33907
- For Sale
$220,000
MLS# 20260349912 bd2 ba1,132 sqft5730 Trailwinds Drive 411, Fort Myers, FL, 33907
- For SaleWaterfront
$154,000
MLS# 20260342812 bd2 ba836 sqft5550 Trailwinds Drive 615, Fort Myers, FL, 33907
- For Sale
$244,900
MLS# 20260319894 bd2 ba1,312 sqft1846 Maple Drive, Fort Myers, FL, 33907
- +21more homes for saleSee the full Trailwinds search →
Swipe to see more →
Recently Sold
Recent sales in Trailwinds
| Home | Bd / Ba | Sq Ft | Sold | Sold Price |
|---|---|---|---|---|
| 2456 Chandler Avenue, Fort Myers | 3 / 2 | 2,034 | Aug 2026 | $410,000 |
| 2100 Barkeley Lane 3, Fort Myers | 1 / 1 | 887 | Aug 2026 | $58,000 |
| 5830 Trailwinds Drive 814, Fort Myers | 3 / 2 | 1,099 | Aug 2026 | $235,000 |
| 2259 Chandler Avenue, Fort Myers | 3 / 2 | 1,164 | Aug 2026 | $315,000 |
Closed sales from the last 12 months. Ask Rick for a full comparable-sales report on any home you're considering.
At a Glance
Trailwinds at a glance
Amenities & Lifestyle
What you get living in Trailwinds
Amenity details vary by HOA / phase. Contact for current specs.
Drive Times
Location & access
- 🏖️ Nearest Beach26 min
- ✈️ RSW Airport22 min
- 🏙️ Downtown Fort Myers12 min
- 🏥 Nearest Hospital10 min
- 🛣️ I-75 Access17 min
Cost of Ownership
Estimated yearly costs for a entry-tier home
Florida estimates based on a $350,000 home in Trailwinds. Actual numbers vary, book a Strategy Session for a live, parcel-specific quote.
Estimates only. Florida Homestead Exemption (when you qualify) can knock $750-1,500 off the annual tax bill.
⚠️ Flood Zone Accuracy Note
Trailwinds is mapped primarily in Zone X
All sample points within Trailwinds returned Zone X. Individual parcels may differ, flood zones are assigned per parcel by FEMA, not per community.
Before making an offer, always verify the exact flood zone for the specific property address:
Source: FEMA National Flood Hazard Layer · sampled at 5 points per community · confidence: high
Schools Nearby
Top schools within 8 miles of Trailwinds
Villas Elementary School
0.3 miTanglewood Elementary School
1.6 miCanterbury School
1.8 miBishop Verot Catholic High School
1.9 miOrangewood Elementary School
2.5 miSouthwest Florida Christian Academy
2.6 miCompare
Similar communities to consider
Ready to Look Closer?
Get live numbers for Trailwinds
HOA dues, current listings, recent sales, builder incentives, all change weekly. Book a free Strategy Session and I'll pull a live snapshot for Trailwinds tailored to your timeline and budget.
Good Questions
Trailwinds, frequently asked questions
- What are home prices like in Trailwinds?
- Trailwinds is in the entry price tier, typically Typically $200K – $450K. List prices vary by size, age, condition, and current inventory; search current listings or ask Rick for live comps.
- What FEMA flood zone is Trailwinds in?
- Trailwinds is mapped primarily in FEMA Zone X, Minimal flood risk. Individual parcels can differ; Rick verifies the exact zone for any address.
- What schools are near Trailwinds?
- Closest schools include Villas Elementary School (0.3 mi), Tanglewood Elementary School (1.6 mi), Canterbury School (1.8 mi). Browse all on the schools directory.
- What does it cost to own a home in Trailwinds?
- For a $350,000 home, estimate roughly $4,550/yr property tax, $1,750-$3,850/yr insurance, and $0-$150/mo HOA. Full breakdown in the SWFL cost cheatsheet.
- What amenities does Trailwinds offer?
- Amenities vary, refer to HOA documents or explore similar communities.