Downtown Sarasota Investment Opportunity! Updated Gillespie Park property with rare 7-day minimum rental flexibility, ADU potential, and strong investment appeal just minutes from downtown Sarasota, The Bay Park, St. Armands Circle, and Lido Beach. This updated home blends classic mid-century character with modern upgrades including terrazzo floors, renovated kitchen with granite countertops, newer appliances, flexible living spaces, and a newer primary suite addition with walk-in closet and private bath. The private backyard offers room for a future pool and possible accessory dwelling unit (ADU), subject to City approval, creating additional long-term value and rental potential. Recent updates include windows, HVAC, hot water heater, washer, and dryer for added move-in-ready convenience. Ideal as a primary residence, seasonal retreat, or income-producing Sarasota investment property in one of downtown’s most desirable neighborhoods. Buyer to verify all measurements, rental restrictions, zoning, ADU potential, and all property information. Property may have audio and/or video surveillance.
- Built in 1954
- $699.41/sqft
- Lot size: 7,920 sqft
- 111 days on market
- Directions: From Fruitville Road, head north on N Osprey Avenue. Continue approximately 0.4 miles.
- County: Sarasota
- Geo subdivision: INWOOD PARK FIRST ADD
Nearby Schools
Alta Vista Elementary
Booker Middle
Booker High
Features
Interior
Exterior
Utilities
Structure
Pets, Accessibility & Amenities
Financial
Lease Information
Tax, Legal & Financing
Let's get in touch!
Let's get in touch!

Jessica Giraldo
Realtor®
- Source: Stellar MLS
- MLS #: A4682221
Listing updated: June 8, 2026 at 2:13PM
Listing provided by: Rex Glasson, DOUGLAS ELLIMAN
Last checked 5 hours ago
Listing provided by: Rex Glasson, DOUGLAS ELLIMAN
Last checked 5 hours ago
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.







