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Southside Village is Sarasota's oldest shopping district, along Osprey Avenue and Hillview Street behind Sarasota Memorial Hospital. We're Eric and Traci Bolen of Sand + Sea Homes with eXp Realty, a husband-and-wife team, and we'd love to help you buy or sell here.
What it is. A walkable shopping and dining district rather than a subdivision: a gourmet market, boutiques, jewelers, galleries, cafes and restaurants.
Location. Just south of downtown, between US-41 and Osprey Avenue.
Market
Price Range
We don't have reliable neighborhood-level market data to publish for Southside Village yet, so we don't quote a median here. Ask us for recent sales of homes with a similar plan, size and location.
Many downtown-area neighborhoods have voluntary associations rather than HOAs, while condos have their own associations, so we check these details with you line by line:
Tax bill and assessments. Ask for the latest property tax bill and check for CDD, stewardship district or other special assessments. Florida taxes also reset after a sale.
Association documents. Review the HOA budget, reserves, what the dues cover, and the leasing, pet and architectural rules before your inspection period ends. Condos and some neighborhoods have an extra association.
Insurance and flood zone. Get insurance quotes, and flood quotes where needed, before you're under contract. Flood zones are assigned home by home. Our post on whether Florida home insurance rates are coming down explains the current picture.
Zoned public schools for Southside Village, from Sarasota County Schools' School Zone Locator (checked Oct 20, 2026 using addresses inside the neighborhood):
Elementary: Southside Elementary School
Middle: Sarasota Middle School
High: Sarasota High School
Sarasota County choice options include Pine View School in Osprey, the district's gifted magnet for grades 2-12 (eligibility testing required), and Booker Middle School's audition-based Visual and Performing Arts magnet. School boundaries change, so always confirm the assigned schools for a specific address with Sarasota County Schools before you buy.
Southside Village is one of the neighborhoods on our Downtown Sarasota list. Head back to our Downtown Sarasota homes and living guide for the big picture, or explore more of Downtown Sarasota:
Along Osprey Avenue and Hillview Street behind Sarasota Memorial Hospital.
Is Southside Village the same as the Southside neighborhood?
No. Southside Village is the shopping district; Southside is the surrounding residential area.
Which schools are zoned for Southside Village?
Based on Sarasota County Schools' School Zone Locator (checked Oct 20, 2026), Southside Village is zoned for Southside Elementary School, Sarasota Middle School and Sarasota High School. Boundaries change, so confirm the schools for a specific address with Sarasota County Schools.
