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$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

Listing courtesy of ENDLESS SUMMER REALTY.

$358,000
5 Beds ⋅ 2 Baths ⋅ 2130699 MLS
Welcome to 17 Aviles Drive, a rare 1928 cottage offering timeless character, flexible living, and exceptional income potential in the heart of St. Augustine. This 5-bedroom, 2-bath home is thoughtfully configured for multigenerational living or house hacking, featuring three total kitchens and a fully functional basement with a private entrance, ideal for extended family, guests, or rental use. Original charm blends seamlessly with modern practicality, including no carpet throughout the entire home, making maintenance simple. The layout allows multiple living zones while still feeling cohesive, offering versatility rarely found in historic homes. Centrally located just minutes from downtown St. Augustine and approximately 15 minutes to St. Augustine Beach, this property puts you close to dining, shopping, historic attractions, and the coast. Zoned RS-2, it allows weekly rentals, opening the door to short-term income opportunities in one of Florida's most sought-after markets. Whether you're looking for a unique primary residence, a multi-generational setup, or a strategic investment, 17 Aviles Drive delivers charm, flexibility, and location in one compelling package. All information pertaining to the property is deemed reliable, but not guaranteed. Information to be verified by the Buyer. Be advised that cameras may exist recording audio and video inside/outside the property, such as ring doorbells. Photos are digitally enhanced and could be altered, please verify.

17 Aviles Drive, St. Augustine

Listing courtesy of DJ & LINDSEY REAL ESTATE.

Selling Office: .

$340,000
3 Beds ⋅ 2 Baths ⋅ 2128665 MLS
Historic 1912 home in the heart of Downtown St. Augustine. This beautifully maintained and fully furnished 3-bedroom, 2-bath residence blends original charm with modern updates and is currently operating as a successful Airbnb. Ideal for investors, a second home, or full-time living. Recent upgrades include AC (3 years), roof (6 years), and water heater (4 years). Prime walkable location near Flagler College, dining, shopping, and historic attractions, with Vilano Beach just minutes away. A rare opportunity to own a piece of St. Augustine history.

22 Marion Street, St. Augustine

Listing courtesy of EXP REALTY LLC.

Selling Office: .

$538,000
4 Beds ⋅ 3 Baths ⋅ 2062987 MLS
For sale is our fully furnished property in the up and coming West St. Augustine. 24 Marion consists of two units; the main house and a back apartment that sits over two single garages. The main house is a charming 1928 3 bedroom, 2 bath house that has been successful as a mid-term and short term rental. The back apartment has enjoyed 100% occupancy with yearly leases. Opportunities abound with this property - house hack, turn apartment into a STR to increase income, bill for garage storage, or move in to the whole place and use the apartment as a guest cottage. Located 1 mile from San Sebastian Winery, this property offers an excellent opportunity. Viewing availability will be dependent on vacancy as we want to respect our guests privacy.

24 Marion Street, St. Augustine

Listing courtesy of HOME SOLD REALTY LLC.

Selling Office: .

$400,000
2 Beds ⋅ 1 Baths ⋅ 2005648 MLS
Welcome to a piece of history in the heart of St. Augustine! This enchanting 1928 cottage, with 2 bedrooms and 1 bath, is a timeless gem that seamlessly blends vintage charm with modern comforts. As you step inside, be greeted by the warmth of original hardwood floors, a testament to the character that has withstood the test of time. The heart of the home is the generously sized kitchen, a chef's dream with ample space and storage. Whether you're preparing a gourmet meal or a quick snack, this kitchen is both functional and inviting. Located on a quiet street, this cottage offers a peaceful escape while being less than 1 mile from historic downtown St. Augustine. Immerse yourself in the rich history, charming boutiques, and delectable dining options that the area has to offer. Plus, with the beach just under 5 miles away, you're never far from the sun, sea, and sand. For those seeking a turnkey vacation rental property, your search ends here. This cottage is being sold fully furnished, making it a hassle-free investment opportunity. Whether you're yearning for a permanent residence with character or a savvy investment in the vacation rental market, this 1928 cottage is your gateway to a timeless lifestyle in St. Augustine. Don't miss the chance to make it yours!

21 Aviles Drive, St. Augustine

Listing courtesy of ENDLESS SUMMER REALTY.

Selling Office: .

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