Florida Real Estate & Lifestyle Blog

    The fourth quarter, October through December, marks an important transition for luxury real estate on Longboat Key and Siesta Key. As Sarasota's winter visitor season approaches, seasonal residents, second-home buyers, and relocation prospects begin returning to Southwest Florida. That creates o

    October 2026 brings beach volleyball, seasonal displays, markets, live music, art festivals and Halloween events to Siesta Key and the Sarasota area. On the island, highlights include the month-long Siesta Key Scarecrow Stroll, the SSOVA Fall College Club Nationals at Siesta Beach and Siesta Key

    Some of the best golf courses near Siesta Key include TPC Prestancia, Bobby Jones Golf Club, Serenoa Golf Club, Stoneybrook Golf & Country Club, Misty Creek Country Club, and Bent Tree Golf Club. Siesta Key itself is known for Gulf beaches rather than golf courses, but mainland Sarasota provides

    Fishermans Haven is a gated, 36-residence condominium at 9150 Blind Pass Road near Turtle Beach on the southern end of Siesta Key. Built in 1975, the seven-story building occupies an unusual waterfront setting, with Gulf beach frontage to the west and protected water with boating access to the e

    Harbor Towers Yacht & Racquet Club is a bayside condominium community at 5855 Midnight Pass Road on Siesta Key, combining Intracoastal waterfront with one of the island's larger condominium marinas. Built in 1976, Harbor Towers also offers two heated outdoor pools, Har-Tru tennis courts, fitness

    Gulf and Bay Club Bayside is a gated condominium community on the Intracoastal side of Siesta Key, combining a bayside waterfront setting with access to Siesta Key Beach across Midnight Pass Road. The community features low-rise residences among landscaped grounds, two swimming pools, tennis and

    Turtle Cove is a small waterfront condominium community at 9000 Midnight Pass Road on the south end of Siesta Key in Sarasota, Florida. With only seven townhome-style residences, a community pool, waterfront setting, boat docks, and close proximity to Turtle Beach Park, Turtle Cove offers a dist

    Siesta Towers is an established high-rise condominium at 4822 Ocean Boulevard on the northern portion of Siesta Key in Sarasota, Florida. Its waterfront setting, elevated views from many residences, community amenities, and proximity to Siesta Key Village give buyers an alternative to lower-rise

    Hamilton Club is an intimate waterfront condominium community on the northern portion of Siesta Key, with just 18 residences arranged in a gated setting near Coconut Bayou and the Intracoastal Waterway. Its multi-level residences are substantially larger than many traditional island condos and c

    Harbour Towne is a gated waterfront condominium community on Siesta Key designed around a protected marina and private boat docks. Located off Midnight Pass Road along Dockside Place, the approximately 50-residence community combines boating access with attached garages, a heated pool and spa, t

    Whispering Sands combines two features that are difficult to duplicate on Siesta Key, a gated beachfront setting and a location immediately convenient to Siesta Key Village. Developed from 1968 to 1973, the community includes 267 residences across condominium buildings and villas, with private G

    Fisherman's Cove occupies an unusual waterfront setting at Turtle Beach on the southern end of Siesta Key. The condominium community sits between the Gulf shoreline and Blind Pass Lagoon, giving residents direct access to the beach while also providing boat slips, kayak launching, and a connecti

    Turtle Bay is a waterfront condominium community on the southern end of Siesta Key, positioned along Little Sarasota Bay near Turtle Beach. The community combines bayfront living with boat docks, a fishing pier, kayak access, a heated pool and spa, tennis and pickleball facilities, tropical grou

    Somerset Cay is a boutique waterfront condominium community at 9122 Midnight Pass Road on the southern end of Siesta Key in Sarasota, Florida. Completed in 2002 with just 17 residences, Somerset Cay combines spacious condominium living with waterfront access, a resort-style pool and spa, fitness

    Tortuga is a beach-to-bay condominium community on the southern portion of Siesta Key in Sarasota, Florida. Located along Midnight Pass Road, the community combines deeded Gulf beach access with access to Little Sarasota Bay and the Intracoastal Waterway, including boat-dock facilities and a fis

  Siesta Sands is a Gulf-side condominium property at 1001 Point of Rocks Road on the southern portion of Siesta Key in Sarasota, Florida. Positioned directly on Crescent Beach near Point of Rocks, the property combines direct shoreline access with two heated pools and individually configured condom

    Summer Cove is a gated waterfront condominium community on Siesta Key in Sarasota, Florida, with 45 residences in two buildings along Little Sarasota Bay. Completed in 2007, the community combines spacious luxury condos with private elevator access, two-car garages, large terraces, a resort-styl

  Siesta Gulf View is an established Gulf-front condominium community at 420 Beach Road on Siesta Key in Sarasota, Florida. Although the community is sometimes described in relation to nearby Siesta Beach, an important distinction for buyers is that Siesta Gulf View itself has direct private access

    A $1 million budget around Siesta Key can put buyers into a surprisingly varied real estate search, but it does not buy the same property everywhere. In 2026, that budget may compete for condominiums on Siesta Key, properties away from direct Gulf frontage, or single-family homes in Sarasota nei

    Windward Passage is a boutique waterfront condominium community at the north end of Siesta Key, offering expansive views across Big Pass while keeping Siesta Key Village close by. Located at 4708 and 4712 Ocean Boulevard, the community combines a relatively small number of residences with waterf