30 photos
Prospect analysis

216 Newfound Blvd

Asking$875,000

Big Pine Key · Big Pine Key, FL · 3 bd · 2 ba · 1,360 sq ft · Built 1991

Underwritten as a short-term rental

Turnkey 3-bedroom pool home in Big Pine Key with established vacation rental performance and canal access.

This property offers a proven short-term rental track record, a private pool, and direct canal access for paddle sports, positioned at a mid-to-upper tier price point. Underwriting metrics indicate strong projected cash flow and cash-on-cash returns, though performance is sensitive to occupancy and nightly rate assumptions.

Est. ADR
$545
Est. occupancy
68%
Gross rev / mo
$11,272
Cash-on-cash
27.9%

Airfolio market estimates · 20% down · detail in the underwriting panel.

Investment thesis

This Big Pine Key property is well-suited for investors seeking a turnkey short-term rental with immediate guest appeal, featuring a pool, spa, and canal access for kayaking and paddle boarding. The home is currently operating as a successful vacation rental, supporting high-confidence income projections. Its open floor plan, updated finishes, and outdoor amenities enhance its rental competitiveness. The primary caveat is that the price point requires sustained strong rental performance to justify returns, and investors should confirm ongoing STR regulatory compliance and operational logistics.

Highlights

  • 3 bedrooms, 2 bathrooms, 1,360 sqft layout
  • Private 14x30 custom pool with heater, chiller, and spa
  • Plugged canal frontage with 15x40 dock (non-boating, paddle sports access)
  • Turnkey offering with established vacation rental history
  • Updated kitchen and bathrooms, impact windows, and open floor plan
  • RV parking with connections and ample storage
  • Covered balcony patio for outdoor dining and entertaining
  • Listed at $875,000, with a Zestimate below list

Risks

STR permitting: verify local ordinance and zoning allow short-term rental at this address before offering. Not verified.
STR regulations and licensing requirements should be verified for ongoing operation
Returns are sensitive to occupancy and ADR assumptions; market seasonality may impact performance
Higher price point limits buyer pool and exit flexibility
Older construction (1991) may require ongoing maintenance
Competition from newer or more waterfront-accessible inventory could pressure pricing
Operational complexity with pool, spa, and canal amenities

Market

Big Pine Key, FL is a well-established vacation rental market in the Florida Keys, attracting guests seeking water access and a relaxed island atmosphere. This property type—single-family home with pool and canal frontage—caters to families and groups seeking privacy and amenities. The market supports premium nightly rates, but performance is closely tied to seasonality and regulatory environment. Confidence in income projections is high due to the property's established rental history and strong amenity set.

Neighborhood

The property's residential setting offers privacy and tranquility, with lush landscaping and fenced yard enhancing guest appeal. Canal frontage supports paddle sports but not boating, which may limit some guest segments. The area is likely to attract families and groups seeking a quiet Keys experience with easy access to outdoor activities. Conclusions about neighborhood-specific demand are moderate-confidence due to limited detailed location signals, but overall guest appeal is strong given the amenity mix.

Underwriting notes

At a list price of $875,000, underwriting projects a monthly expected income of $11,272 and cash flow of $4,076, with a projected cash-on-cash return of 27.9% under high-confidence assumptions (68% occupancy, $545 ADR, 25% expense ratio, 20% down, 6.4% interest). These figures are driven by the property's established STR performance and amenity package. Returns are highly sensitive to occupancy and nightly rate; investors should confirm that current rental demand and regulatory conditions are sustainable. Expense ratio assumes efficient management and may vary with operational complexity.

Sign up free to adjust these assumptions and save your own underwriting.

Figures are Airfolio market estimates modeled from listing, record, and market data, not investment advice · Analysis Aug 20, 2026.
Airfolio is a product of Trusty Labs, Inc. · CA DRE #01527508

Prospect analyses and a concierge for short-term-rental investors.

We’ll send Today’s Deal Flow twice a week — underwritten opportunities, filtered to your markets. Unsubscribe anytime.

Airfolio is a product of Trusty Labs, Inc., a licensed California real estate brokerage · CA DRE #01527508. Concierge introductions to agents, lenders, and property managers are referrals, and Trusty Labs may receive referral fees. Revenue and return figures are Airfolio market estimates from public records, listing data, and market modeling, not offers, appraisals, or investment advice. Verify all figures independently.
© 2026 Trusty Labs, Inc.
548 Market St PMB 40276, San Francisco, CA 94104-5401