Riverside is one of the most desirable single-family home neighborhoods within the gated Caloosa Yacht & Racquet Club community in Fort Myers, Florida. Known for its spacious homes, private waterfront and preserve settings, mature tropical landscaping, and exceptional boating lifestyle, Riverside offers homeowners a unique combination of privacy, luxury, and resort-style amenities. Developed primarily during the late 1980s and early 1990s, this exclusive neighborhood features a limited collection of custom residences that reflect the timeless character and relaxed elegance of one of Fort Myers' premier waterfront communities.
Conveniently located off McGregor Boulevard near College Parkway, Riverside enjoys one of South Fort Myers' most desirable locations. Residents are just minutes from Downtown Fort Myers' Historic River District, Fort Myers Beach, the Sanibel Causeway, Cape Coral, Bell Tower Shops, Barbara B. Mann Performing Arts Hall, HealthPark Medical Center, and Southwest Florida International Airport (RSW). The community offers outstanding access to shopping, dining, healthcare, and entertainment while maintaining the peaceful atmosphere of a private, gated waterfront neighborhood.
Constructed primarily between the late 1980s and early 1990s, Riverside features custom-built single-family homes with a variety of architectural styles, including Mediterranean and Florida Coastal designs. Homes generally range from approximately 1,800 to over 3,500 square feet of living space and commonly feature three- and four-bedroom floor plans, attached two- and three-car garages, soaring ceilings, expansive screened lanais, gourmet kitchens, generous primary suites, and private swimming pools. Many residences have been extensively updated with quartz or granite countertops, custom cabinetry, impact-resistant windows and doors, luxury flooring, smart-home technology, and designer coastal finishes that complement the community's waterfront setting.
One of Riverside's defining characteristics is its peaceful setting. Many homes overlook scenic canals, lakes, or protected preserve areas, while others enjoy beautifully landscaped streets lined with mature oak trees and tropical palms. The neighborhood offers a quiet residential atmosphere where homeowners regularly enjoy sightings of herons, egrets, pelicans, dolphins, manatees, and other native Florida wildlife. Large homesites and mature landscaping provide a level of privacy rarely found in newer Southwest Florida communities.
A major advantage of living in Riverside is access to Caloosa Yacht & Racquet Club's outstanding boating amenities. Residents have access to the community's 56-slip deep-water marina, where boat slips are available to residents on a first-come, first-served basis. The marina provides direct access to the Caloosahatchee River, the Intracoastal Waterway, and the Gulf of Mexico, making it easy to enjoy boating excursions to Fort Myers Beach, Sanibel Island, Captiva Island, Cabbage Key, and numerous waterfront restaurants throughout Southwest Florida.
Residents of Riverside also enjoy the exceptional amenities offered throughout Caloosa Yacht & Racquet Club. These include four tennis courts, active pickleball programs, an Olympic-size heated swimming pool, shuffleboard courts, scenic walking paths, a waterfront park, fishing pier, kayak launch, and beautifully maintained tropical common areas. The community hosts an active calendar of boating events, tennis leagues, pickleball play, and neighborhood social gatherings that foster a welcoming and close-knit atmosphere.
One of the community's signature amenities is the private Blue Coyote Supper Club, located directly within Caloosa Yacht & Racquet Club. Overlooking the marina and Caloosahatchee River, this members-only waterfront restaurant provides exceptional dining in a relaxed yet elegant atmosphere. Residents enjoy the convenience of walking, biking, or arriving by boat for dinner while taking in spectacular waterfront views, making the Blue Coyote one of the most distinctive lifestyle amenities available in any Fort Myers waterfront community.
Unlike many newer developments, Riverside offers the character of an established neighborhood with mature landscaping, generous lot sizes, and timeless architecture. The combination of gated security, marina access, low-density development, and outstanding recreational amenities continues to make Riverside one of the most sought-after neighborhoods within Caloosa Yacht & Racquet Club. Limited inventory and strong buyer demand contribute to excellent long-term property values and enduring appeal among both seasonal and year-round residents.
Real estate within Riverside remains highly desirable because of its spacious homes, peaceful surroundings, boating amenities, and exceptional South Fort Myers location. Whether buyers are searching for a primary residence, seasonal retreat, or waterfront investment property, Riverside offers one of the finest boating lifestyles available within Caloosa Yacht & Racquet Club.
Lifestyle at Riverside
Life at Riverside revolves around Southwest Florida's relaxed waterfront lifestyle. Residents spend their mornings walking beneath mature shade trees, launching kayaks, or heading out for a day on the Caloosahatchee River. Afternoons are often spent playing tennis or pickleball, relaxing by the heated community pool, fishing from the pier, or enjoying the marina. Evenings bring spectacular river sunsets and waterfront dining at the Blue Coyote Supper Club. Whether boating to nearby islands, enjoying an active social calendar, or relaxing from a private lanai overlooking the water, homeowners experience one of Fort Myers' most unique and rewarding waterfront lifestyles.
Your Local Fort Myers Waterfront Real Estate Experts
The McGreevy and Comisar Team at Domain Realty is led by Jesse McGreevy and Marc Comisar, Southwest Florida real estate specialists with extensive experience throughout Fort Myers, Estero, Bonita Springs, Naples, Cape Coral, and the region's premier waterfront and boating communities. Together, they have completed more than 1,700 transactions and over $860 million in career sales throughout Southwest Florida.
Jesse and Marc regularly help buyers and sellers navigate Riverside at Caloosa Yacht & Racquet Club real estate, providing expert guidance on waterfront homes, boating communities, marina access, HOA considerations, investment opportunities, seasonal and year-round living, and long-term property values. Their local expertise helps clients understand the unique advantages of owning within one of Fort Myers' most established and desirable riverfront communities.
