1655 South Drive, Sarasota, FL 34239
$5,900,000 - For Sale
Property Details
Price: $5,900,000
Sq Ft: 6,355
($928 per sqft)
Bedrooms: 5
Bathrooms: 5
Partial Baths: 4
City:Sarasota
County:Sarasota
Type:Single Family
Development:Cherokee Park
Subdivision:Cherokee Park
Acres:0.3400
Virtual Tour/Floorplan:View
Year Built:2011
Listing Number:A4684423
Status Code:A-Active
Taxes:$34,624.73
Tax Year: 2025
Garage: 3
/ Y
Furnishings: Unfurnished
Pets Allowed: Yes
Total Recurring Fees: $27
Total Recurring Fee Frequency: 0.00
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Equipment:
Bar Fridge
Built-In Oven
Cooktop
Dishwasher
Disposal
Dryer
Gas Water Heater
Microwave
Range
Range Hood
Refrigerator
Tankless Water Heater
Washer
Interior Features:
Built-in Features
Cathedral Ceiling(s)
Ceiling Fans(s)
Crown Molding
Dry Bar
Elevator
High Ceilings
Open Floorplan
Primary Bedroom Main Floor
Solid Surface Counters
Solid Wood Cabinets
Split Bedroom
Stone Counters
Thermostat
Tray Ceiling(s)
Vaulted Ceiling(s)
Walk-In Closet(s)
Wet Bar
Window Treatments
Exterior Features:
Balcony
French Doors
Lighting
Misting System
Other
Outdoor Grill
Outdoor Kitchen
Outdoor Shower
Rain Gutters
Sidewalk
Sliding Doors
View:
Garden
Pool
Trees/Woods
Financial Information:
Taxes: $34,624.73
Tax Year: 2025
Association Fee: $325.00
Association Fee Frequency: Annually
Room Dimensions:
Laundry: Inside, Laundry Room, Other, Upper Level
School Information:
Elementary School: Southside Elementary
Middle School: Brookside Middle
Junior High: Brookside Middle
High School: Sarasota High
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View Virtual Tour
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.
Building Description: Custom, Other
MLS Area: 34239 - Sarasota/Pinecraft
Total Square Footage: 8,306
Price per Square Feet: $928.40
Total Floors: 3
Water: Public, Well
Lot Desc.: Flood Zone, City Limits, Near Public Transit, Sidewalk, Street Dead-End, Paved
Construction: Block, Stone, Stucco
Date Listed: 2026-03-01 00:00:00
Pool: Y
Pool Description: Deck, Gunite, Heated, In Ground, Lighting, Other, Outside Bath Access
Private Spa: Y
Furnished: Unfurnished
Windows: Blinds, Energy Star Qualified Windows, Storm Window(S), Thermal Windows
Parking: Garage Door Opener, Garage Faces Rear, Garage Faces Side, Ground Level
Garage Description: Y
Garage Spaces: 3
Flooring: Concrete, Hardwood, Tile, Travertine, Wood
Roof: Membrane, Metal, Tile
Heating: Central, Electric, Natural Gas, Zoned
Cooling: Central Air, Zoned
Pets: Yes
Sewer: Public Sewer
Listing Courtesy Of: Premier Sotheby's International Realty
katy.mcbrayer@premiersir.com
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.
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Additional Information:
Building Description: Custom, Other
MLS Area: 34239 - Sarasota/Pinecraft
Total Square Footage: 8,306
Price per Square Feet: $928.40
Total Floors: 3
Water: Public, Well
Lot Desc.: Flood Zone, City Limits, Near Public Transit, Sidewalk, Street Dead-End, Paved
Construction: Block, Stone, Stucco
Date Listed: 2026-03-01 00:00:00
Pool: Y
Pool Description: Deck, Gunite, Heated, In Ground, Lighting, Other, Outside Bath Access
Private Spa: Y
Furnished: Unfurnished
Windows: Blinds, Energy Star Qualified Windows, Storm Window(S), Thermal Windows
Parking: Garage Door Opener, Garage Faces Rear, Garage Faces Side, Ground Level
Garage Description: Y
Garage Spaces: 3
Flooring: Concrete, Hardwood, Tile, Travertine, Wood
Roof: Membrane, Metal, Tile
Heating: Central, Electric, Natural Gas, Zoned
Cooling: Central Air, Zoned
Pets: Yes
Sewer: Public Sewer
Map of 1655 South Drive, Sarasota, FL 34239
Listing Courtesy Of: Premier Sotheby's International Realty
katy.mcbrayer@premiersir.com
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Location
2100 Constitution Boulevard
Sarasota, FL 34231
Contact
Jennifer Leblanc, Broker
941-400-0374
IDX information is provided exclusively for consumers’ personal, noncommercial 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. The data relating to real estate for sale on this Website comes in part from the Broker Reciprocity Program (BR Program) of My Florida Regional MLS DBA Stellar MLS. The source of this real property information is the copyrighted and proprietary database compilation of the My Florida Regional MLS DBA Stellar MLS and © 2026. Information last refreshed: 2026-05-14 16:03:09
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