One or more photo(s) has been virtually staged. In Sarasota's

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Home For Sale

1655 SOUTH DR

Sarasota, Florida 34239

Sarasota County

Community: CHEROKEE PARK

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$5,900,000 5 br, 9.0 bath 6355 sq. ft. 0.340 acres

One or more photo(s) has been virtually staged. In Sarasota's desired West of Trail enclave of Cherokee Park, 1655 South Drive, masterfully designed three-story estate where thoughtful architecture meets effortless luxury. Positioned on a homesite that is not in a Special Flood Hazard Area and enhanced with full home hurricane-impact glass and a whole-home generator, this residence offers the rare combination of refinement and peace of mind. Spanning 6,355+ square feet, the home features five bedrooms, five full baths and four half baths, with a layout tailored for grand entertaining and everyday ease. A rear three-car garage, accessed discreetly from South Lodge Drive, preserves the home's striking street presence. Inside, the main level unfolds into a wide-open living experience with a great room with wet bar, formal dining, and a showpiece chef's kitchen outfitted with Wolf dual-oven six-burner range, dual side by side 36* Sub-Zero Over-and-Under Refrigerator/Freezers, a Wolf microwave drawer, a Wolf warming drawer, and built-in Miele espresso machine. The first-floor primary suite is a private retreat, complete with an in-home gym, a spa-inspired bath and dual custom-fitted closets. A beautifully appointed guest suite (fifth bedroom) with en-suite bath also anchors the main level. Access to the upper floors is seamless via a dramatic staircase with custom wrought-iron railings or the private elevator. Upstairs, three additional en-suite bedrooms include custom walk-in closets, one thoughtfully designed with built-in bunk beds, plus a bonus club room with built-in desks and additional laundry for added convenience. Outdoors, the property transforms into a walled and gated resort-style oasis featuring a gas-heated saltwater pool with sun shelf and spa, and an artificial turf lounge/play area. A screened entertainment lounge with a convenient half pool bath connects to a full outdoor kitchen with sink, TV and gas grill, all complemented by a pergola and a mosquito misting system, ideal for Sarasota's seasons. Above the garage, a spectacular casita-style retreat, accessible by the home's second private interior elevator or exterior spiral staircase, elevates entertaining to an entirely new level with a 2,000-bottle refrigerated wine room, a fully equipped wet bar, mini- fridge, clear ice maker, and dishwasher. Go onto the covered terrace with a gas fireplace, then unwind on the third floor in the private, pool-like infinity-edge spa, an experience that feels equal parts boutique resort and private club. Ideally in walking distance to A-rated Southside Elementary School, Southside Village, Sarasota Memorial Hospital, downtown Sarasota and short drive to the world-famous sands of Siesta Key Beach, this is a rare opportunity to own a bespoke residence in one of Sarasota's treasured neighborhoods.

Interior:
  • Bedrooms: 5
  • Baths: 9.0
  • Sq Ft: 6355
  • Year Built: 2011
  • Utilities: 
  • Fireplaces: Has Fireplace
  • Stories: 
  • Heat/AC: Central, Electric (Heating), Fireplace(s), Natural Gas, Zoned (Heating)
  • Garage: Garage, Garage - Attached
Exterior:
  • Lot Size: 0.340 acre
  • Lot Dimensions: 
  • View Types: 
  • Yard: 
  • Siding: Block, Stone, Stucco
  • Roof: Membrane, Metal, Tile
  • Property Taxes: $34,625
  • Yearly HOA Fee: $324
  • Swimming Pool: Yes
  • MLS #: A4684423
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Contact Information:
Beach Home For Sale in Sarasota, Florida
Listing Agent: Katy McBrayer, Premier Sotheby's International Realty, 941-400-2406, 941-364-4000 Listing Site, Listing Status: Active
Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Ad Number: 7674865
Viewed 9 times.
Updated: May 06, 2026

This property is a Home located at 1655 SOUTH DR, Sarasota, Florida 34239, and is currently For Sale at $5,900,000. This Home has 5 bedrooms, 9.0 baths, 6355 sq ft.