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A Rare Piece of Sarasota History with current income of over 167,000 / yr. Four turn-key furnished residences. Three City Lots. One Extraordinary Piece of Sarasota History. Welcome to 941 Virginia Drive, a truly unique historic property originally built by John Ringling Jr., offering vintage Sarasota charm paired with modern flexibility and lucrative income. Set on three city lots, this 125-foot-long masonry residence creates an extraordinary private compound with four distinct living spaces. The main residence features two bedrooms, one and a half bathrooms, and an office or den, highlighted by timeless architectural details including stone porches, arched doorways, pecky cypress paneling, tall vaulted beamed ceilings and a wood-burning fireplace. Modern updates complement the historic character with stainless steel appliances, granite countertops, and updated fixtures. The property is designed for lifestyle, opportunity and flexibility for extended family, guests or continued successful short-term rental business. In addition to the main home, the estate includes three separate guest residences providing privacy and versatility. There are two in-law suites that feature full kitchens, a private pool, hot tub, outdoor shower, patio access and a private bathroom; one offers one bedroom and the other two bedrooms. There is an additional one-bedroom dwelling with a convenient kitchenette, private bathroom and laundry. Located just two miles north of downtown Sarasota, the property offers easy access to Lido Key, Longboat Key, St. Armands Circle, and the vibrant dining, arts, and cultural scene of downtown Sarasota. Whether you envision a private historic estate, a multi-generational compound or a unique established vacation rental business, this rare property offers exceptional character, privacy and opportunity in one of Sarasota's most desirable locations. Don't miss this opportunity to Own a Piece of Ringling History "” A Private Sarasota Compound with Vintage Charm and Resort-Style Living.
| DAYS ON MARKET | 19 | LAST UPDATED | 3/13/2026 |
|---|---|---|---|
| TRACT | BAY HAVEN | YEAR BUILT | 1945 |
| COMMUNITY | 34234 - Sarasota | COUNTY | Sarasota |
| STATUS | Active | PROPERTY TYPE(S) | Single Family |
| Elementary School | Emma E. Booker Elementary |
|---|---|
| Jr. High School | Booker Middle |
| High School | Booker High |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer |
| AREA | 34234 - Sarasota |
| CONSTRUCTION | Block |
| EXTERIOR | Lighting, Outdoor Grill, Outdoor Shower, Private Yard, Rain Gutters, Storage |
| FIREPLACE | Yes |
| HEAT | Central, Electric |
| INTERIOR | Built-in Features, Coffered Ceiling(s), Vaulted Ceiling(s) |
| LOT | 0.37 acre(s) |
| LOT DESCRIPTION | Corner Lot, Landscaped, Paved |
| LOT DIMENSIONS | 149x100 |
| PARKING | Driveway |
| POOL | Yes |
| POOL DESCRIPTION | Gunite, Heated, In Ground, Salt Water, Screen Enclosure, Private |
| SEWER | Public Sewer |
| STORIES | 1 |
| STYLE | Florida, Mid-Century Modern |
| SUBDIVISION | BAY HAVEN |
| TAXES | 9216.86 |
| UTILITIES | Cable Available, Natural Gas Available, Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected |
| VIEW | Yes |
| VIEW DESCRIPTION | Pool, Trees/Woods |
| WATER | Public |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listing provided by Angela Adams, MICHAEL SAUNDERS & COMPANY, 941-951-6660
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 3/14/26 12:55 PM PDT.
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