5 Southwest Florida Investment Finds from Fort Myers to Sarasota

In the heart of Fort Myers, this well-maintained, fully occupied six-unit building is designed for straightforward, durable ownership. Built of solid concrete block and professionally managed, it’s positioned to deliver consistent cash flow with long-term tenant stability, supported by a stated 6.87% cap rate. Across 14 bedrooms and 10 bathrooms, each residence is arranged with a practical, easy-to-maintain layout that suits everyday living. On-site parking adds welcome convenience for tenants, while the location near major roadways keeps the city within easy reach. Shopping, restaurants, public transportation, and downtown Fort Myers are all close by, reinforcing day-to-day accessibility and ongoing rental demand. It’s a property that quietly performs, offering an urban rhythm shaped by connectivity and consistency.

Price: Contact for pricing

On Boca Grande, this residence is positioned to capture sweeping, unobstructed views of the shimmering Gasparilla Sound. The setting invites an easy rhythm—mornings framed by open water, afternoons watching light shift across the Sound, and evenings that feel naturally expansive thanks to the uninterrupted outlook. Equally suited for full-time living or as an investment property, it offers the rare appeal of ownership in a coveted coastal locale with a clear focus on what matters most: the view. With Boca Grande just outside your door, the everyday experience centers on island atmosphere and the calming presence of the water. It’s a place designed to be lived in lightly and returned to often, where the Sound becomes a constant, luminous backdrop.

Steps from 5th Avenue, Cambier Park, and the beach, this spacious one-bedroom condo places you in the heart of Olde Naples’ most walkable, charming surroundings. Inside, the residence is flooded with natural light, and the space has already been cleared and prepped—an inviting blank canvas for anyone eager to design a personal retreat. A private outdoor patio extends the living area, offering an easy spot for morning coffee or a quiet evening wind-down. The building’s flexible rental policy adds welcome freedom: enjoy it as your own Naples escape and rent it out when you’re away. Pet-friendly living rounds out the everyday ease, so four-legged companions can share in the neighborhood rhythm. It’s a setting that encourages simple days on foot and a home shaped entirely by your vision.

Price: Contact for pricing

Set on a wide, picturesque acreage in Naples, this land is framed by the ever-popular Picayune Strand State Forest, creating a setting that feels immersed in Southwest Florida’s natural rhythms. Days here come with an abundance of wildlife—black bear, deer, wild boar, possum, raccoons, and a sky alive with exotic birds and eagles—offering an unfiltered connection to the landscape. The oversized parcel is presented as an investment opportunity with a range of stated possibilities, from farming and agriculture to a single-family home. For those drawn to the outdoors, the description also envisions a hunting or sports camp, even noting the concept of one cabin per acre. Walk the land, take in the quiet, and imagine a life shaped by nature and open-ended potential.

Size: 20.34 acres

In Sarasota’s River Forest neighborhood, this thoughtfully reimagined, block-constructed residence balances discretion with day-to-day ease. Tastefully and comprehensively renovated with an emphasis on comfort, cohesion, and quiet luxury, the interiors revolve around an open, flowing floor plan where living, dining, and kitchen spaces connect seamlessly for both everyday routines and relaxed entertaining. A four-seat breakfast bar in the kitchen encourages casual gatherings, while the living room’s peaceful sunset views bring a gentle close to the day. The setting keeps you close to the area’s treasured coastal and boating destinations, with multiple access points that make getting around feel effortless. Just 1/2 mile from Phillippi Estate Park, under a mile to Phillippi Harbor Club, and less than two miles to Siesta Key Beach, it’s a place where privacy and proximity naturally coexist.