Historic South Side Homes under $500,000

Historic South Side Homes under $500,000

Welcome to the Historic South Side of Apalachicola, Florida—a charming neighborhood steeped in rich history and Southern hospitality. Nestled along the picturesque shores of the Gulf of Mexico, this vibrant community is known for its stunning architecture, tree-lined streets, and a sense of timelessness that beckons residents and visitors alike.

The Historic South Side features an eclectic mix of homes that reflect the area's storied past, with many properties showcasing beautiful Victorian and Craftsman-style designs. Here, you can find an array of homes available for under $500,000, making it an attractive option for first-time buyers, families, and retirees seeking a tranquil lifestyle. Whether you’re looking for a cozy cottage or a spacious family home, this neighborhood offers a variety of choices that cater to diverse tastes and budgets.

Living in the Historic South Side means enjoying the best of both worlds—peaceful suburban living combined with easy access to Apalachicola's bustling downtown. Residents can stroll through charming streets filled with local boutiques, art galleries, and delightful eateries serving up fresh seafood and Southern cuisine. Plus, the nearby Apalachicola River and pristine beaches provide endless opportunities for outdoor activities, from fishing and kayaking to leisurely beachcombing.

Experience the warmth and charm of the Historic South Side, where you can find your dream home at an affordable price while immersing yourself in the beauty and culture of this unique coastal town. Discover the perfect blend of history, community, and affordability in one of Florida's hidden gems!

Newest Historic South Side Homes under $500,000

50 15th St, Apalachicola
$275,000
2 Beds ⋅ 1 Baths ⋅ 329566 MLS
For Sale: Located in the desirable South Historic District, this authentic Apalachicola cottage is ready for renovation. See the potential in its high ceilings, open floorplan, original windows and a covered front porch. This special cottage also retains its original tongue and groove pine floors, walls and ceilings. Location is key, Lafayette Park is less than 2 blocks away where you can enjoy the serenity of Apalachicola Bay. Call today for an appointment!

50 15th St, Apalachicola
141 Ave D, Apalachicola
$310,000
3 Beds ⋅ 2 Baths ⋅ 327749 MLS
Located in the coveted southside of Apalachicola's Historic District, this corner property sits at Ave D and 11th Street with convenient alley access and the easygoing charm that defines this coastal town. Freshly painted and well maintained, this 3-bedroom, 1.5 bath home offers a wonderful opportunity to step into the Apalachicola lifestyle while adding your own personal touches over time. Built in 1985, the home features 1,056 sq ft heated and cooled (1,660 total) with a comfortable semi-open living, kitchen, and dining space that feels welcoming the moment you walk in. The primary bedroom includes a private half bath, while the full bathroom is conveniently located in the hallway and easily accessible for guests and the additional bedrooms. Outside, the property continues to offer practical and flexible spaces. The utility room sits conveniently under the carport, and an additional storage building provides the perfect spot for a golf cart, small workshop, or extra storage. The partially fenced backyard includes a concrete pad ready for outdoor living, grilling, or a safe space for your pooch to enjoy. A new HVAC system was installed in 2025, and a new hot water heater installed in 2023 along with new vinyl siding. With solid bones, a desirable Southside location, and room to make it your own, this Apalachicola home is ready for its next chapter. Buyer to verify all information through inspections, survey, appraisal, or preferred due diligence. Taxes and insurance are specific to the current owner and may change at closing.

141 Ave D, Apalachicola
59 Ave D, Apalachicola
$499,000
4 Beds ⋅ 4 Baths ⋅ 323808 MLS
HEART of historic Apalachicola—59 Ave D presents an exceptional multi-unit property that combines charm, convenience, and thoughtful modern upgrades in one of the Gulf Coast's most beloved small towns. Recently remodeled, each of the four 1-bedroom, 1-bath units blends contemporary finishes with classic Apalachicola character. Every unit features its own kitchen and living area for privacy and comfort, plus an efficient mini-split HVAC system, a washer and dryer, and a private porch or balcony—perfect for relaxing and soaking in the neighborhood's appeal. Units A and B come fully furnished, offering immediate move-in or rental income potential. A tankless Rinnai on-demand hot water system provides energy-efficient comfort throughout. The lush backyard green space creates a peaceful retreat for gardening, unwinding, or enjoying the Florida sunshine, while the inviting shared porches—upstairs and down—offer the perfect spot for morning coffee, friendly chats, or watching the quiet street life go by. With no short-term rentals permitted, the setting remains serene and community-focused, making this an ideal choice for stable, long-term investment or multi-generational living. Just steps from vibrant downtown Apalachicola, you'll enjoy easy access to boutique shops, acclaimed restaurants, art galleries, and the scenic riverfront. From weekend markets to lively festivals, everything that defines the town's laid-back coastal lifestyle is within walking distance. Whether you choose to live in one unit and lease the others or secure a fully updated property in a prime location, 59 Ave D is a rare opportunity. Be sure to check out the high def 3D video tour. Call for your private tour & LIVE THE BEACH LIFE! *Seller in the LLC is a licensed real estate agent in the state of Florida.

59 Ave D, Apalachicola
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