Key West Rooftop Bungalows-3 new construction, hurricane-resistant, storm-strong, steel built, rooftop-deck bungalows in Englewood, FL—sit under 2 miles from Manasota Key Beach and ~20 minutes from Billionaire Boca Grande. It’s the perfect blend of unique, experience-forward design and blue-water access that keeps calendars full and rates premium. The construction EXCEEDS Miami Dabe hurricane codes and is built well above the 100-year FEMA flood tables! Perfect STR portfolio:
Most-Likely Financial Snapshot (2026)
NOI: ~$158,351
Cap Rate: ~15.8% on $1,000,000
Cash-on-Cash: ~45% (20% down)
Modeled IRS§179/Bonus: up to $900,000 Yr-1 deductions ? ~$360,000 tax savings at a 40% bracket*
Why this location wins!
Boca Grande • Manasota Key • Englewood — a hidden gem on Florida’s Gulf Coast. Guests step onto sugar-sand beaches, launch boats/jet skis into Lemon Bay, kayak mangrove tunnels, and spend luxe afternoons in Boca Grande’s lighthouse village.
At a glance:
Manasota Key Beach: ~2 miles (quick drive or bike)
Stump Pass Beach State Park: ~10 minutes
Boca Grande (Gasparilla Island): ~20 minutes
Water: Lemon Bay/ICW marinas + boat & jet ski rentals + SUP/kayak eco-tours minutes away
Waterfront Dining: Farlow’s on the Water, Lock ’N Key (Englewood Beach), Magnolia’s on the Bay (Manasota), Pink Elephant (Boca)
Regional access: Sarasota, Venice, Fort Myers, Cape Coral — under 1 hour. Tampa & Naples — under 2 hours.
For sale by owner
$1,000,000
1741 Winstan Ave, Englewood, FL 34223
6beds
3,840sqft
Est.:
Commercial
Built in 2025
-- sqft lot
$-- Zestimate®
$260/sqft
$-- HOA
What's special
Rooftop-deck bungalowsKayak mangrove tunnelsSugar-sand beaches
What the owner loves about this home
Timing is everything and with the “Big Beautiful Bill,” investors may pursue up to $900,000 of first-year deductions in 2025 via IRS§179 and bonus depreciation when supported by cost segregation and proper qualification (investor-specific; consult your CPA).
Why the product stands out
Steel construction: hurricane-resistant, low-maintenance, no rot/termites; watertight roof-deck design.
Experience-led stays: rooftop sunset decks + vibrant Key West vibe; exactly the “wow” factor that wins online**.
Turnkey portfolio: three matching 2BR/1BA units (sleep 6) with housekeeping & lodging tax passed through to guests.
Place in service by December 31, 2025 to pursue 2025 deductions with your CPA. Please share this deep dive with The Real Estate CPA with your CPA to ensure your qualification:
https://www.therealestatecpa.com/blog/short-term-rental-tax-loophole/
WRITE-OFF UP TO $900,000 on either your 2025 or 2026 taxes! Send your money to Washington, DC or own the coolest Key West Roof Top Bungalows on the Cape Haze Peninsula
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