1655 SOUTH DRIVE Sarasota, FL $ 5,900,000
1655 SOUTH DRIVE
$ 5,900,000
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1655 SOUTH DRIVE

Sarasota, FL, 34239
$ 5,900,000
Bedrooms5 Baths5.4 Sq 6,355

Monthly Estimate*

$ 36,327

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Single Family Home for sale in Sarasota, FL

for $5,900,000 with 5 bedrooms and 5 full baths, 4 half baths. This 6,355 square foot home was built in 2011 on a lot size of 0.34.

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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Single Family Active

Price

$ 5,900,000

Bedrooms

5

Full Bath

5

Half Bath

4

Property Type

Single Family

Taxes

$ 34,624

Style

Custom Other

Lot Size

0.34

Year Built

2011

Town/City

Sarasota

County/Region

Sarasota

MLS | Web ID

A4684423

Features
General
Sewer Public Sewer
Heating Central Electric Natural Gas Zoned
Cooling Central Air Zoned
Utilities Cable Connected Electricity Connected Natural Gas Connected Public Sewer Connected Sprinkler Well Water Connected
Roof Membrane Metal Tile
Appliances Bar Fridge Built-In Oven Cooktop Dishwasher Disposal Dryer Gas Water Heater Microwave Range Range Hood Refrigerator Tankless Water Heater Washer
Zoning RSF1
HOA Fee 325
Garage Spaces 3
Patio/Porch Features Covered Deck Other Patio Porch Rear Porch Screened Side Porch
Architectural Style Custom Other
Pool Features Deck Gunite Heated In Ground Lighting Other Outside Bath Access
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)
Construction Materials Block Stone Stucco
Pets Allowed Yes
Year Built 2011
View Garden Pool Trees/Woods
Levels Three Or More
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Assoc Fee Paid Per Annually
County Sarasota
New Construction false
Property Type Residential
Attached Garage true
Energy Efficient Appliances HVAC Roof Thermostat Windows
Subdivision Name CHEROKEE PARK
Facing Direction South
Garage Y/N true
Green Indoor Air Quality HVAC Cartridge/Media Filter HVAC Filter MERV 8+ HVAC UV/Elec. Filtration Ventilation
Green Water Conservation Low-Flow Fixtures Whole House Water Purification
Total Rooms 13
Full Baths 5
Status Active
Directions South on Osprey Ave turn right on South Drive home is on the left 1655 South Drive.
High School Sarasota High
City SARASOTA
Senior Community Y/N false
MLS Area 34239 - Sarasota/Pinecraft
Lot Size Units Square Feet
Lot Size Square Feet 15000
Carport Y/N false
Listing Terms Cash Conventional
Spa Features Above Ground Heated Other
Elementary School Southside Elementary
Land Lease Y/N false
Tax Annual Amount 34624.73
Home Warranty Y/N false
Middle/Junior High School Brookside Middle
Property Condition Completed
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://tours.coastalhomephotography.net/2371569?idx=1
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 6
Legal Description LOT 6 BLK C CHEROKEE PARK
Minimum Lease No Minimum
Water Access Y/N false
Monthly HOA Amount 27.08
Additional Rooms Bonus Room Breakfast Room Separate Den/Library/Office Family Room Formal Dining Room Separate Formal Living Room Separate Great Room Inside Utility Interior In-Law Suite w/Private Entry Loft Storage Rooms
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities 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
Flooring Concrete Engineered Hardwood Porcelain Tile Travertine Hardwood
Furnished Y/N Unfurnished
Fireplace Features Gas Living Room Outside
Total Stories 3
Air Conditioning Y/N true
Heating Y/N true
Window Features Blinds ENERGY STAR Qualified Windows Storm Window(s) Thermal Windows
Fireplace Y/N true
Half Baths 4
Laundry Features Inside Laundry Room Other Upper Level
Total Bedrooms 5
Total Baths 9
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Exterior
Exterior Amenities Balcony French Doors Irrigation System Lighting Misting System Other Outdoor Grill Outdoor Kitchen Outdoor Shower Rain Gutters Sidewalk Sliding Doors
Vegetation Mature Landscaping Oak Trees Trees/Landscaped
Fencing Electric Fenced Masonry Stone
Parking Features Garage Door Opener Garage Faces Rear Garage Faces Side Ground Level
Lot Features FloodZone City Lot Near Public Transit Sidewalk Street Dead-End
Water Source Public Well
Lot Size Area 15000
Foundation Details Slab Stem Wall
Spa true
Building Area Total 8306
Lot Size Acres 0.34
Road Surface Type Paved
Private Pool true
Waterfront Y/N false
Covered Spaces 3
Road Frontage Type Street Dead-End Street Paved
Road Responsibility Public Maintained Road
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* Excluded Features
List By
Premier Sotheby's International Realty

Broker

Katy.McBrayer@premiersir.com

Email

Affordability Calculator

$39,213
Per Month
93%
7%
0%
Monthly Principal & Interest
$36,327
Monthly Property Taxes
$2,885
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Sarasota High High School High School
Pricing History
DatePricePrice ChangeDescription
5/5/2026$5,900,000 Listed Price

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1655 SOUTH DRIVE, Sarasota, FL, 34239 is a Single Family Home for sale at $5,900,000 with 6,355 sqft and a lot size of 0.34. 1655 SOUTH DRIVE has 5 bedrooms, 5.4 baths, and was built in 2011. The property's zip code is 34239 which is in Sarasota, FL