1655 SOUTH DRIVE SARASOTA FL 34239 MLS #A4684423

1655 SOUTH DRIVE
SARASOTA, FL, 34239
$5,900,000
5 Beds
7 Baths
6,355 SqFt
0.34 Acres
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MLS #A4684423 image #0
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.

Property Details

Price:
$5,900,000
MLS #:
A4684423
Status:
Active
Beds:
5
Baths:
7
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
CHEROKEE PARK
Neighborhood:
34239sarasotapinecraft
Listed Date:
Mar 1, 2026
Finished Sq Ft:
6,355
Total Sq Ft:
8,306
Lot Size:
15,000 sqft / 0.34 acres (approx)
Year Built:
2011
PoolPrimary Bedroom Main Floor34239 – Sarasota/pinecraft34239sarasotapinecraftCherokee ParkSouthside ElementaryBrookside MiddleSarasota HighNo MinimumPets Allowed

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Schools

Elementary School:
Southside Elementary
Middle School:
Brookside Middle
High School:
Sarasota High

Interior

Appliances
Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer
Bathrooms
5 Full Bathrooms, 4 Half Bathrooms
Cooling
Central Air, Zoned
Flooring
Concrete, Engineered Hardwood, Porcelain Tile, Travertine, Hardwood
Heating
Central, Electric, Natural Gas, Zoned
Interior Features
Built-in Features, Cathedral Ceiling(s), Ceiling Fan(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
Laundry Features
Inside, Laundry Room, Other, Upper Level
Levels
Three Or More

Exterior

Architectural Style
Custom, Other
Attached Garage YN
1
Construction Materials
Block, Stone, Stucco
Covered Spaces
3
Direction Faces
South
Exterior Features
Balcony, French Doors, Irrigation System, Lighting, Misting System, Other, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Rain Gutters, Sidewalk, Sliding Doors
Fencing
Electric, Fenced, Masonry, Stone
Garage Spaces
3
Green Energy Efficient
Appliances, HVAC, Roof, Thermostat, Windows
Lot Features
FloodZone, City Lot, Near Public Transit, Sidewalk, Street Dead-End
Parking Features
Garage Door Opener, Garage Faces Rear, Garage Faces Side, Ground Level
Patio And Porch Features
Covered, Deck, Other, Patio, Porch, Rear Porch, Screened, Side Porch
Roof
Membrane, Metal, Tile
Security Features
Closed Circuit Camera(s), Fire Sprinkler System, Security Fencing/Lighting/Alarms, Security Gate, Security Lights, Security System, Security System Owned, Smoke Detector(s)
Spa Features
Above Ground, Heated, Other
View
Garden, Pool, Trees/Woods
Window Features
Blinds, ENERGY STAR Qualified Windows, Storm Window(s), Thermal Windows

Financial

HOA Fee
$325
HOA Fee Frequency
Annually
Tax Year
2025
Taxes
$34,625

Map

Community

Subdivisions in SARASOTA

Market Summary

Current real estate data for Single Family in SARASOTA as of May 06, 2026
2,230
Single Family Listed
112
Avg DOM
489
Avg $ / SqFt
$1,502,666
Avg List Price

Property Summary

    Located in the CHEROKEE PARK subdivision, 1655 SOUTH DRIVE SARASOTA FL is a Single Family for sale in SARASOTA, FL, 34239. It is listed for $5,900,000 and features 5 beds, 7 baths, and has approximately 6,355 square feet of living space, and was originally constructed in 2011. The current price per square foot is $928. The average price per square foot for Single Family listings in SARASOTA is $489. The average listing price for Single Family in SARASOTA is $1,502,666. To schedule a showing of MLS#a4684423 at 1655 SOUTH DRIVE in SARASOTA, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

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