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$710,900
4 Beds ⋅ 4 Baths ⋅ 2146405 MLS
At this price point, duplexes on the island are incredibly rare--and finding one with a coveted, active short-term rental (STR) license is nearly impossible. This turnkey, fully furnished property is an absolute powerhouse. Each unit features 2 bedrooms, 2 bathrooms, an oversized driveway, and a spacious, fully fenced backyard. Tucked away on a quiet dead-end street, it offers guests a peaceful, secluded oasis that is still just an effortless stroll from the beach and the premier new dining options at Anastasia Plaza. It is no surprise this has been a stellar, high-yield income producer since 2023. Schedule your private tour today! Buyer to verify all measurements.

6 Lisbon Street Unit A/B, St. Augustine
$649,000
2 Beds ⋅ 1 Baths ⋅ 2132516 MLS
Historic charm meets modern performance in this 1925 St. Augustine treasure. Fully restored and upgraded with a new roof, windows, electrical, plumbing, siding, and more--bringing it up to 2025 standards. The first floor is leased as office space through October 2026, providing steady income. Upstairs, a beautifully furnished two-bedroom apartment operates as a vacation rental, consistently achieving nearly 250 booked nights each year. Located within easy reach of St. Augustine's historic district, dining, and attractions, this property offers a rare combination of character and cash flow. Showings by appointment only. Financial details available to qualified buyers.

55 S Dixie Highway, St. Augustine
$949,000
4 Beds ⋅ 2 Baths ⋅ 2128943 MLS
Rare downtown St. Augustine duplex — fully furnished, fully restored, and full of opportunity. Just one block from the nation's oldest street and two blocks from the bayfront, this historic property delivers an unbeatable location with flexible income potential. Each of the two apartments features 2 bedrooms, 1 bath, a full kitchen, living room, eat-in area, and private laundry. Property has up to four parking spots. The owner has preserved the historic character while upgrading electrical, plumbing, and HVAC — each unit has its own electric meter and central heat & air. Enjoy over 1,880 sqft of living space with covered porches, a balcony, and a private back patio perfect for grilling or pets. Rent both units for maximum returns, live in one and rent the other, or convert to a single-family home with ease. All appliances included. Minutes to the beaches, steps to dining, shopping, and everything that makes St. Augustine one of the most desirable locations in Florida.

251 Charlotte Street, St. Augustine
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