Sarasota County, Florida
Sarasota County
Florida’s cultural capital — world-class arts, barrier island beaches, historic bayfront estates, and some of the most sought-after real estate on the Gulf Coast. From the powdery white sand of Siesta Key to the refined elegance of Longboat Key, Sarasota County offers six distinct lifestyle zones within one market.
6
Distinct Areas
#1
Siesta Key — America’s Best Beach
12mi
Longboat Key Shoreline
$500k+
County Median Home Price
Also exploring neighboring markets? Visit our guides for Anna Maria Island, Lakewood Ranch, and Bradenton — all expertly covered by Sea to Sky Realty.
Browse by Area
Explore Sarasota County
Longboat Key
Longboat Key is Sarasota County’s most exclusive barrier island — 12 miles of pristine Gulf shoreline anchored by the legendary Longboat Key Club resort. Estate homes, luxury condominiums, and private gated communities define this refined enclave.
Short-term rental activity is highly restricted throughout most of the island, making Longboat Key a stable, owner-occupied community with strong long-term value.
Longboat Key connects directly to Anna Maria Island to the north via the Cortez Bridge. Explore our Anna Maria Island Area Guide for the neighboring barrier island market.
Longboat Key Club
Premier gated resort community on the southern tip of Longboat Key, featuring golf, tennis, and beach access.
View Listings →Bay Isles
Prestigious waterfront enclave behind the gates of the Longboat Key Club with direct bay access.
View Listings →Longbeach Village
Historic bohemian village on the northern tip of Longboat Key with old-Florida character and charm.
View Listings →Harbour Villa Club
Boutique bayfront community offering deep-water boat slips and refined coastal living.
View Listings →Whitney Beach
Quiet north-end community with deeded beach access and laid-back Gulf Coast lifestyle.
View Listings →Live MLS Data · Updated Daily
Longboat Key Listings
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Lido Key & St. Armands
Lido Key and Bird Key sit just west of downtown Sarasota, connected via the John Ringling Causeway. St. Armands Circle anchors this sophisticated island enclave where upscale condominiums and estate homes command prime Gulf-front positions.
The 34236 ZIP code is one of Sarasota’s most prestigious addresses, blending walkable beach-town charm with access to the best of downtown cultural life.
Looking for barrier island options further north? Explore Anna Maria Island or Longboat Key — both expertly covered by Sea to Sky Realty.
Bird Key
Exclusive island community in Sarasota Bay featuring estate homes on deep-water lots.
View Listings →Lido Shores
Upscale waterfront neighborhood with Gulf and bay access, no HOA restrictions, and strong investment appeal.
View Listings →Ritz-Carlton Beach Club Residences
Ultra-luxury beachfront residences managed by the Ritz-Carlton brand on Lido Key.
View Listings →St. Armands Circle Area
Vibrant mixed-use district surrounding the iconic St. Armands Circle with boutique shops and fine dining.
View Listings →Lido Beach Condominiums
Mid-rise and high-rise Gulf-front condominiums offering direct beach access and resort-style amenities.
View Listings →Orchid Beach Club
Exclusive boutique Gulf-front tower with only 29 residences offering unparalleled privacy and luxury.
View Listings →Live MLS Data · Updated Daily
Lido Key & St. Armands Listings
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Siesta Key
Siesta Key consistently earns the title of America’s Best Beach for its remarkable quartz-crystal sand. This eight-mile barrier island delivers world-class beaches, a vibrant village atmosphere, and a diverse real estate market ranging from oceanfront cottages to multimillion-dollar estates.
The island’s rental market is robust, with many communities permitting short-term rentals. Always verify zoning compliance before purchasing as an investment property.
⚠️ STR Licensing Note: Short-term rental licensing on Siesta Key is governed by Sarasota County zoning ordinances. Requirements change regularly. Always verify current licensing requirements and confirm with HOA governing documents before purchase.
Siesta Village Area
The heart of Siesta Key with walkable beach access, shops, and restaurants — popular with vacation rental investors.
View Listings →Midnight Cove
Gulf-front condominium community with STR-friendly policies and strong rental income potential.
View Listings →Siesta Isles
Established residential neighborhood with canals, no-bridge water access, and STR-permitted lots.
View Listings →Gulf & Bay Club
Beachfront resort-style condominium community with direct Gulf access and active rental program.
View Listings →Point of Rocks
Southernmost tip of Siesta Key with spectacular natural rock formations and snorkeling — no HOA.
View Listings →Whispering Sands
Quiet north-end enclave known for its pristine beach and serene residential atmosphere.
View Listings →Live MLS Data · Updated Daily
Siesta Key Listings
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Downtown Sarasota
Downtown Sarasota is one of Florida’s most culturally vibrant urban cores — home to the Van Wezel Performing Arts Hall, world-class museums, award-winning restaurants, and a thriving arts scene centered on the Ringling legacy.
The downtown market spans the Rosemary District arts neighborhood, established Burns Court bungalows, and ultra-luxury branded residences. Most buildings are long-term rental communities.
Just minutes from downtown: explore Lido Key & St. Armands for Gulf-front island living, or Siesta Key for America’s top-rated beach.
The Mark Sarasota
Award-winning luxury high-rise in the heart of downtown with rooftop amenities and walkable urban lifestyle.
View Listings →One Park Sarasota
New luxury tower adjacent to The Bay Park, offering panoramic bay views and world-class amenities.
View Listings →Ritz-Carlton Residences Sarasota
Branded ultra-luxury residences offering Ritz-Carlton service and bayfront grandeur.
View Listings →Rosemary District
Sarasota’s arts and innovation quarter — a walkable neighborhood of galleries, studios, and new residential development.
View Listings →Burns Court
Historic bungalow district with tree-lined streets, no-HOA homes, and proximity to the Burns Court Cinema.
View Listings →Alinari at Rosemary Place
Boutique mid-rise condominium in the Rosemary District with a curated arts-forward community identity.
View Listings →Live MLS Data · Updated Daily
Downtown Sarasota Listings
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West of Trail Sarasota
West of Trail refers to the prestigious residential neighborhoods situated between US-41 (Tamiami Trail) and Sarasota Bay — one of the most coveted addresses in all of Sarasota. This enclave of historic homes, canopied streets, and architectural gems sits within walking or biking distance of the bay.
The area encompasses several distinct neighborhood identities — from the estate homes of Harbor Acres and McClellan Park to the artisan character of the Flower Streets. Most properties carry no HOA, offering significant flexibility for buyers.
Harbor Acres
Grand bayfront estates on Sarasota Bay with deep-water docks, majestic oaks, and no-HOA flexibility.
View Listings →McClellan Park
Historic neighborhood of architecturally significant homes and tree-canopied streets close to Southside Village.
View Listings →Cherokee Park
Established residential enclave with large lots, mature landscaping, and a quiet neighborhood character.
View Listings →Avondale
Charming neighborhood with no HOA, strong rental demand, and proximity to Southside Village.
View Listings →DeSoto Park
Bayfront and near-bay properties with exceptional value and access to Sarasota’s best waterfront parks.
View Listings →Southside Village / Flower Streets
Walkable arts district with eclectic bungalows, boutique retail, and a vibrant community identity.
View Listings →Live MLS Data · Updated Daily
West of Trail Sarasota Listings
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North Sarasota
North Sarasota stretches from downtown northward toward Sarasota-Bradenton International Airport, encompassing historic neighborhoods, emerging arts districts, and affordable residential communities. Indian Beach and Sapphire Shores are among Florida’s most architecturally significant historic districts.
The area offers excellent value compared to the barrier islands, with long-term rental demand driven by proximity to the airport and the University Parkway corridor.
North Sarasota borders Bradenton to the north. Explore the full Bradenton neighborhoods guide for the neighboring Manatee County market covered by Sea to Sky Realty.
Sapphire Shores
Bayfront enclave of mid-century and historic homes adjacent to the Ringling Museum of Art on Sarasota Bay.
View Listings →Indian Beach Historic District
One of Sarasota’s most architecturally diverse neighborhoods, recognized for its historic character and bay proximity.
View Listings →Whitfield Estates
Established waterfront community along Sarasota Bay with boating access and a strong neighborhood identity.
View Listings →Bay Haven
Affordable single-family neighborhood with easy airport access and strong owner-occupant community identity.
View Listings →Sarasota Springs
Growing residential area with strong long-term rental demand from the local workforce.
View Listings →University Parkway Corridor
Active mixed-use corridor along University Parkway anchored by higher education and commercial development.
View Listings →Live MLS Data · Updated Daily
North Sarasota Listings
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Explore Neighboring Markets
Anna Maria Island
Seven barrier island communities on Florida’s Gulf Coast — from historic Bridge Street to the natural beauty of Bean Point. Manatee County’s crown jewel.
Bradenton
From downtown Bradenton’s arts scene to the waterfront village of Cortez and the beaches of Anna Maria Island — Manatee County’s diverse coastal market.
Lakewood Ranch
America’s best-selling master-planned community — a lifestyle-driven destination spanning Manatee and Sarasota counties with exceptional amenities.
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We cover all six Sarasota County areas — Longboat Key, Lido Key, Siesta Key, Downtown Sarasota, West of Trail, and North Sarasota. Share your criteria and we’ll match you with the right community.