Issue No. 78 · The Deal Drop
4
Properties
$250K
Top Revenue
33%
Top ROI
📋 What’s Inside This Drop
Four different angles, four different markets — here’s the quick read on what’s worth a deeper look this drop.
Property 1 —Pigeon Forge, TN: $444K STR opportunity generating projected ~$80K/year (~18% ROI) with a unique Dolly-inspired theme, proven rental history, and a prime location minutes from the Parkway.
Property 2 — Gulf Shores, AL: $615K STR opportunity generating projected ~$128K/year (~21% ROI) with a 2024-built coastal cottage, private beach access, and nearly half an acre just steps from the Gulf.
Property 3 — Frankfort, KY: $525K STR opportunity generating projected ~$175K/year (~33% ROI) with 4,700+ sqft, a finished basement, and significant upside along the Bourbon Trail.
Property 4 — St. Augustine, FL: $1.73M STR opportunity generating projected ~$250K/year (~15% ROI) with beach access steps away, a heated pool, and a brand-new luxury build.
🏠 The Properties
We pressure-tested hundreds of listings this week. Here’s the shortlist — ranked by projected ROI after expenses.
📋 2 Beds • 2 Baths • 986 sqft
🏷️ Price: $444,000
💵 Projected Annual: $80K
📈 Est. Gross ROI: 18%
Why it made the cut:
Proven STR with 115+ Airbnb reviews and a 4.98 rating
Top 5% on Airbnb with strong rental history
Unique Dolly-inspired design creates a memorable, highly marketable guest experience
Turnkey 2BR/2BA with themed bedrooms and Instagram-worthy spaces
Less than 5 minutes from the Pigeon Forge Parkway and close to Dollywood, dining, and attractions
Rare sub-$450K entry point in one of the Smokies' strongest STR markets
📋 3 Beds • 2 Baths • 1,077 sqft
🏷️ Price: $615,000
💵 Projected Annual: $128K
📈 Est. Gross ROI: 21%
Why it made the cut:
2024 construction with a turnkey 3BR/2BA layout
~0.46-acre lot offers rare space and privacy near the beach
Short walk to private community beach access in Surfside Shores
Strong guest appeal from white-sand beaches, golf, and outdoor recreation
Close to Bon Secour National Wildlife Refuge, Kiva Dunes, and Fort Morgan
21% projected gross ROI at a $615K entry price
📋 4 Beds • 3 Baths • 4,704 sqft
🏷️ Price: $525,000
💵 Projected Annual: $175K
📈 Est. Gross ROI: 33%
Why it made the cut:
4BR/3BA renovated home with 4,704 sqft at just ~$112/sqft
Blank-slate backyard ready for high-impact amenities like a hot tub, fire pit, and Mod Pool
Same street as a high-performing STR, providing a strong nearby comp
Just minutes from Buffalo Trace Distillery and within easy reach of Georgetown and Lexington
Finished basement adds substantial space for games, entertainment, or additional guest amenities
Strong potential to create a high-end Bourbon Trail STR with professional design and furnishing
📋 4 Beds • 4 Baths • 2,763 sqft
🏷️ Price: $1,725,000
💵 Projected Annual: $250K
📈 Est. Gross ROI: 15%
Why it made the cut:
Built in 2024 with high-end finishes and a professionally designed interior
Just one house from the beach with boardwalk access steps away
Heated pool, fire pit, outdoor shower, and spacious deck create a strong resort-style guest experience
Elevator serving all three levels adds convenience for groups and families
Flexible first-floor space can function as a 5th bedroom, cabana, or additional gathering space
Quiet dead-end street close to St. Augustine Beach dining, shopping, and attractions
Want the full deal packet? Reply “DEAL + Property #” and we’ll send the numbers, photos & comps.
Prefer to skip the reply and get matched to deals like these on autopilot?
📍 Market of the Week: Morganton, GA
Why Frankfort continues to stand out: a 98 Submarket Score, 97 Investability Score, and 88 Rental Demand Score point to strong underlying fundamentals in a small, supply-constrained market with multiple year-round demand drivers.
The three levers driving performance right now:
Elite investment fundamentals — A 97 Investability Score and 88 Rental Demand Score make Frankfort one of the stronger-scoring submarkets for investors looking for an established Kentucky STR market.
Diversified tourism drivers — Kentucky's state capital, historic downtown, bourbon tourism, Buffalo Trace, and local events create multiple reasons for visitors to stay in the area beyond traditional leisure travel.
Small competitive set — With just 92 active listings, Frankfort remains a relatively small STR market, giving individual properties the opportunity to differentiate through location, amenities, and guest experience.
Frankfort is a high-scoring, small-market STR opportunity with strong investability and diversified demand, where careful property selection matters as the market works through recent revenue softness.
🎯 YOUR SHORTCUT: THE MARKET MATCH CALL
Skip the guesswork. Tell us your budget, risk tolerance, and the kind of returns you’re chasing — we’ll match you with markets and deals that actually fit, before they hit the wider market.
💡Webinar Spotlight
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— The Deal Drop Team 💧