Uptown, FL homes for sale & real estate

Uptown, FL Homes for Sale

Downtown St. Augustine Bungalow - Airbnb-Ready with Multi-Unit Potential Located in the heart of Historic St. Augustine, this charming 3 bed, 2 bath bungalow offers a rare opportunity for both personal enjoyment and serious investment. Just a short stroll to the city's best shops, restaurants, and attractions, this is exactly where travelers want to be. The layout provides a unique opportunity: With a little vision and renovation, this home can be transformed into two separate units—a 2 bed, 1 bath space downstairs and a 1 bed, 1 bath with an office upstairs. Live in one, rent the other, or maximize your returns by offering two Airbnb listings under one roof. Whether you're a seaso

Uptown, FL Homes for Sale

Charming Downtown Bungalow - A Rare Airbnb Investment Opportunity Nestled in the heart of Historic St. Augustine, this 2 bed, 1 bath bungalow is brimming with charm, potential, and opportunity. Just a short walk to the shops, restaurants, and vibrant attractions of the nation's oldest city, this location is everything for guests seeking that perfect St. Augustine experience. The home itself needs a little love, but savvy investors will immediately see the equity upside with some thoughtful updates. Whether you're dreaming of creating your own cozy vacation rental or a personal weekend getaway, this is a diamond ready to shine. Here's what makes it even more exciting: This property is one

Uptown, FL Homes for Sale

Step into the storybook charm of this 1908-built home, perfectly located in the heart of Downtown St. Augustine. Rich in character and thoughtfully updated, this property offers the ideal blend of timeless architecture, everyday comfort, and flexible living. Inside, original hardwood floors and period details set a warm, welcoming tone. The formal dining room is perfect for hosting, while the downstairs bedroom—with a private bath—offers versatility as a guest room, home office, or cozy retreat. Upstairs, the primary suite is a light-filled sanctuary featuring a wall of windows and a private balcony—an ideal spot for morning coffee or an evening wind-down. Each bedroom inc

Uptown, FL Homes for Sale

Beautifully restored and renovated 1919 vintage Florida Bungalow! Offering 2-bedrooms, 1.5-bathroom, this charming home is ideally located in the heart of Historic Downtown St. Augustine. Thoughtfully designed living space, this property offers both comfort and convenience—currently operating as a successful short-term rental! A screened front porch sets the tone for relaxed Florida living, welcoming you into a bright interior with hardwood flooring throughout. The living room flows into a cozy dining area, creating a warm, open feel. Head back to the kitchen, complete with stainless steel appliances, a breakfast bar, and a convenient half bath. A door off the kitchen opens to the bac