Search St. Augustine Investment Properties For Sale, $400,000 – $500,000

Beautiful Duplex for sale within very close proximity to downtown St Augustine! This proven AirBnb/VRBO short-term-rental features 2 total bedrooms and bathrooms. Completely turn key property zoned commercial on A1A/Anastasia Blvd in Davis Shores neighborhood. Very convenient walk to multiple restaurants, shops and bars around the old city of St. Augustine. Multiple upgrades include new exterior doors, windows, bathroom vanities, toilets, paint, appliances, heating/ac wall mounted units installed by Glacier Heating and Air and fenced back yard. Some updated electric and plumbing. Encapsulated crawl space with dehumidifier installed by Alpha Foundations. No water intrusion on the property including during Hurricane Ian. All furniture and appliances stay, turn key opportunity. Buyer to verify info. $479,000 Active

313 ANASTASIA Boulevard A & B St Augustine, Florida

916 SqFt 0.11 Acres

Fantastic Duplex in a Growing Community with Top-Rated Schools! Investors and homeowners alike, don't miss this incredible opportunity to own a well-maintained duplex in a thriving area! Situated on a large corner lot, this property offers two spacious units—each with modern updates and functional layouts. Both units feature remodeled kitchens, solid flooring throughout, and enclosed porches—perfect for extra living space or relaxation. Each unit also enjoys the convenience of separate laundry rooms, adding privacy and value for tenants or homeowners. Located in a fast-growing neighborhood with highly rated public schools, this duplex is an ideal investment, whether you're looking for rental income or a multi-generational living solution. Enjoy the benefits of an established community with easy access to shopping, dining, and local parks. Don't wait—duplexes like this are a rare find! Contact us today for more details or to schedule a private showing. $475,000 Active

4588 FIRST Avenue St Augustine, Florida

5 Beds 2 Baths 1,340 SqFt 0.15 Acres

This vintage 1940's Duplex situated on two lots is the best investment opportunity in the City of St. Augustine. Located a stone's throw from Historic Downtown in the heart of booming West Augustine, this renovated cottage with Airbnb guest house offers the perfect opportunity to step into St. Augustine life with immediate built-in income. Tucked away on the coveted and quiet Live Oak Street, walk out your front doorstep and take a leisurely stroll to enjoy the vibrant energy of West King Street with boutiques, cafes, neighborhood pubs and local brewery. Recently fully updated with modern wood-toned flooring, new roof, HVAC, kitchen, baths and more, this home offers low-maintenance urban living while maintaining Old Town charm. The oversized double lot is surrounded by towering Grandaddy live oaks and a serene backdrop of mature tropical foilage. The property offers plenty of off-street parking, privacy, room for entertaining or a pool. Whether this lucrative multi-family property is to be a full-time primary residence or income-producing investment, every bit of this charming Duplex near Historic Downtown symbolizes the quintessential St. Augustine lifestyle. Situated steps away from local favorites like Buena Onda, Bog Brewery, The West Egg and The Blue Hen, this bungalow is the perfect opportunity to create your new life in St. Augustine. Nothing Compares. $469,000 Active

509 LIVE OAK Street St Augustine, Florida

3 Beds 1 Baths 1,472 SqFt 0.13 Acres

View All