Vintage homes for sale & real estate in St. James City, FL

Vintage Home for sale in St. James City, FL:

Welcome to 2631 Bayshore Drive, a classic Matlacha cottage that perfectly blends Old-Florida charm with the waterfront lifestyle this island is famous for. This beautifully maintained home offers three bedrooms, two bathrooms, and an inviting, open layout filled with natural light. The living room features a cozy fireplace, creating a warm focal point for gatherings. The kitchen and bathrooms have been thoughtfully updated, combining modern functionality with coastal style, while the home’s warm character and classic touches create a relaxing environment that instantly feels like home. Situated on a generous lot, the property offers an exceptional waterfront setup complete with a priv

Vintage Home for sale in St. James City, FL:

Island living with unforgettable sunsets! Completely remodeled with marvelous style, this 2-bedroom + 2 dens, 2-bathroom 1952 home is tucked away on a coveted peninsula in the island community of Matlacha. Surrounded by the bay, this is true paradise for boaters, kayakers, and fishermen alike. Cathedral ceilings and an abundance of natural light make the home feel even more spacious, while upgraded modern light fixtures add a fresh, stylish touch. Every detail has been thoughtfully updated—LVP floors throughout, an all-new kitchen with 42” cabinets, Seaglass quartz counters, a large apron sink, and sleek finishes. Bathrooms feature spa-inspired touches like natural pebble shower

Vintage Home for sale in St. James City, FL:

Located in the heart of Matlacha, 11494 May Street is a designated historic cottage that captures the character and charm of Old Florida. The home’s original features have been well cared for and have served the sellers comfortably for years. The new owners can enjoy its vintage appeal as is or choose to enhance and modernize it to their taste. With its historical designation, buyers can also raise the home for additional parking or storage, which is a popular trend on the island. Whether you’re a fishing captain, weekend paddler, or simply someone drawn to the leisurely pace of island living, Island Time Begins Here, and this property offers endless potential in one of Southwes

Vintage Home for sale in St. James City, FL:

Sitting on the Dock of the Bay — the Best Seat in the House! Welcome to your slice of paradise! This fully remodeled and beautifully updated coastal cottage offers never-ending views of the water and breathtaking sunsets — right from your own backyard. Whether you’re dreaming of a laid-back island lifestyle or looking for a fantastic vacation rental (VRBO) opportunity, this home is pure perfection. Two cozy bedrooms, one stylish bath, and an unbeatable location for anyone whose heart belongs to the water — boating, fishing, or simply soaking in the coastal beauty. Rebuilt after Hurricane Milton, this gem features all-new everything — including a brand-new dock

Vintage Home for sale in St. James City, FL:

Enjoy the breathtaking sunset views from this amazing Matlacha property. Its's all about location and this is the location to be. Just a few steps from downtown Matlacha and just a few minutes to the open waters of the gulf. The property has a historic home on it. The home can be lifted and repaired or you may choose to start fresh and build your own million dollar dream home. With this view, a well built home would have incredible value! Whichever the case you will have a great island get-away. The pool could easily be left and built around to save time and money! The custom pool is perfect for enjoying those lazy summer days. Watch the dolphins play as you take a dip. Make this property y

Vintage Home for sale in St. James City, FL:

Own a Piece of Paradise on Matlacha Island! Welcome to island living at its finest! This beautiful 2-bedroom, 1.5-bath waterfront home offers direct Gulf access with no bridges—a true dream for boating and fishing enthusiasts. Located in the heart of vibrant Matlacha, this charming property is ideal as a full-time island retreat or a relaxing second home. Step out your back door to your private boat lift with a protective canopy, making it easy to hit the water anytime while keeping your vessel safe from the elements. Whether you're heading out for a day of fishing or a sunset cruise, your boating lifestyle starts right here. Inside, enjoy a cozy and open layout designed for easy