Harbourside is one of the premier single-family home neighborhoods within the gated Caloosa Yacht & Racquet Club community in Fort Myers, Florida. Known for its spacious waterfront homes, private canal views, boating lifestyle, and mature tropical surroundings, Harbourside offers homeowners an exceptional combination of luxury, privacy, and resort-style living. Developed primarily during the early 1990s, this exclusive enclave features a limited collection of single-family residences that enjoy access to one of Southwest Florida's most unique waterfront communities.
Conveniently located along the historic McGregor Boulevard corridor near College Parkway, Harbourside enjoys one of South Fort Myers' most desirable locations. Residents are only minutes from Downtown Fort Myers' River District, Fort Myers Beach, the Sanibel Causeway, Bell Tower Shops, Barbara B. Mann Performing Arts Hall, HealthPark Medical Center, Cape Coral, and Southwest Florida International Airport (RSW). The community provides easy access to shopping, dining, healthcare, and entertainment while maintaining the peaceful atmosphere of a private gated waterfront neighborhood.
Constructed primarily in the early 1990s, Harbourside features beautifully designed single-family homes with open floor plans, concrete block construction, tile roofs, attached two-car garages, screened lanais, and spacious outdoor living areas. Homes generally offer approximately 1,700 to over 4,000 square feet of living space with thoughtfully designed three- and four-bedroom floor plans. Many residences feature soaring ceilings, gourmet kitchens, generous primary suites, private swimming pools, and expansive lanais overlooking canals or lush tropical landscaping. Numerous homes have been extensively updated with quartz or granite countertops, custom cabinetry, luxury flooring, impact-resistant windows and doors, smart-home technology, and designer coastal finishes.
One of Harbourside's defining characteristics is its peaceful waterfront setting. Many homes are situated along intersecting canals that provide beautiful water views and an authentic coastal atmosphere. Mature oak trees, royal palms, colorful tropical landscaping, and quiet streets create a serene environment where residents frequently enjoy sightings of herons, egrets, pelicans, dolphins, and manatees. Several homes feature private pools and generous outdoor entertaining areas designed to maximize Southwest Florida's year-round indoor-outdoor lifestyle.
A major advantage of living in Harbourside is access to the community's outstanding boating amenities. Residents may lease available slips at the private 56-slip deep-water marina, which offers protected dockage for vessels up to approximately 36 feet. The marina provides direct access to the Caloosahatchee River, the Intracoastal Waterway, and the Gulf of Mexico, making it easy to enjoy boating adventures to Fort Myers Beach, Sanibel Island, Captiva Island, Cabbage Key, and numerous waterfront restaurants throughout Southwest Florida. Marina slips are offered on a first-come, first-served basis at competitive rates for residents.
Residents of Harbourside also enjoy the extensive recreational amenities offered throughout Caloosa Yacht & Racquet Club. These include four tennis courts, an active pickleball program, an Olympic-size heated swimming pool, shuffleboard, a scenic lakefront park with walking paths, picnic and barbecue areas, a kayak launch, fishing opportunities, and beautifully maintained tropical common areas. The community maintains an active social calendar featuring boating events, tennis leagues, neighborhood gatherings, and seasonal celebrations that foster a close-knit atmosphere.
One of the community's most unique features 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 an elegant yet relaxed setting. Residents enjoy the convenience of walking, biking, or arriving by boat for dinner while taking in panoramic waterfront views, making the Blue Coyote one of the community's signature lifestyle amenities.
Unlike many newer developments, Harbourside offers an established neighborhood with mature landscaping, generous lot sizes, and timeless architecture. The combination of gated security, marina access, waterfront views, and low-density development continues to make Harbourside one of Fort Myers' most desirable boating neighborhoods. 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 Harbourside remains highly sought after due to its canal-front setting, spacious homes, boating amenities, and outstanding South Fort Myers location. Whether buyers are searching for a full-time residence, seasonal retreat, or waterfront investment property, Harbourside offers one of the finest boating lifestyles available within Caloosa Yacht & Racquet Club.
Lifestyle at Harbourside
Life at Harbourside revolves around Southwest Florida's relaxed waterfront lifestyle. Residents enjoy morning walks beneath mature oak trees, afternoons boating along the Caloosahatchee River, tennis and pickleball matches with neighbors, kayaking from the community launch, fishing from nearby docks, and evenings dining at the Blue Coyote Supper Club while watching spectacular river sunsets. Whether spending the day exploring nearby barrier islands or relaxing beside a private pool overlooking the canal, homeowners enjoy one of Fort Myers' most distinctive 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 Harbourside 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 exclusive and sought-after waterfront neighborhoods.
