To schedule a showing of 1655 South Drive, Sarasota, Florida, Call David Shippey at 863-521-4517 TODAY!
$5,900,000 | 5 beds | 5 full baths | 4 half baths | 6,355 sqft
Sarasota, FL 34239
- 5Beds
- 9.00Total Baths
- 5 Full, 4 HalfBaths
- 6,355SqFt
- 2011Year Built
- 0.34Acres
- MLS# A4684423
- Residential
- SingleFamilyResidence
- Active
- Approx Time on Market3 months, 7 days
- Area34239 - Sarasota/pinecraft
- CountySarasota
- Subdivision Cherokee Park
Overview
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 homes 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.
Agriculture / Farm
Association Fees / Info
Community Features: Sidewalks
Pets Allowed: Yes
Hoa Frequency Rate: 325
Association: Yes
Hoa Fees Frequency: Annually
Bathroom Info
Total Baths: 9.00
Fullbaths: 5
Building Info
Window Features: Blinds, EnergyStarQualifiedWindows, StormWindows, ThermalWindows, WindowTreatments
Roof: Membrane, Metal, Tile
Building Area Source: PublicRecords
Buyer Compensation
Exterior Features
Style: Custom, Other
Pool Features: Gunite, Heated, InGround, OutsideBathAccess, Other
Patio: RearPorch, Covered, Deck, Other, Patio, Porch, Screened, SidePorch, Balcony
Pool Private: Yes
Exterior Features: Balcony, FrenchPatioDoors, SprinklerIrrigation, Lighting, MistingSystem, OutdoorGrill, OutdoorKitchen, OutdoorShower, Other, RainGutters
Fees / Restrictions
Financial
Original Price: $5,900,000
Disclosures: FloodPlainDisclosure
Fencing: Electric, Fenced, Masonry, Stone
Garage / Parking
Parking Features: Garage, GarageDoorOpener, GarageFacesRear, GarageFacesSide
Attached Garage: Yes
Garage: Yes
Green / Env Info
Green Features: Appliances, Hvac, Roof, Thermostat, Windows
Green Water Conservation: LowFlowFixtures
Green Indoor Air Quality: ContaminantControl,Filtration,Ventilation
Interior Features
Fireplace Desc: Gas, LivingRoom, Outside
Fireplace: Yes
Floors: Concrete, EngineeredHardwood, PorcelainTile, Travertine, Wood
Levels: ThreeOrMore
Spa: Yes
Laundry Features: Inside, LaundryRoom, Other, UpperLevel
Interior Features: WetBar, BuiltInFeatures, TrayCeilings, CeilingFans, CrownMolding, CathedralCeilings, DryBar, Elevator, HighCeilings, MainLevelPrimary, OpenFloorplan, StoneCounters, SplitBedrooms, SolidSurfaceCounters, VaultedCeilings, WalkInClosets, WoodCabinets, WindowTreatments, SeparateFormalDiningRoom, SeparateFormalLivingRoom, Loft
Appliances: BarFridge, BuiltInOven, Cooktop, Dryer, Dishwasher, Disposal, GasWaterHeater, Microwave, Range, Refrigerator, RangeHood, TanklessWaterHeater, Washer, WaterPurifier
Spa Features: AboveGround, Heated
Lot Info
Direction Remarks: South on Osprey Ave, turn right on South Drive, home is on the left 1655 South Drive.
Lot Size Units: Acres
Lot Size Acres: 0.34
Lot Sqft: 15,000
Vegetation: Oak, PartiallyWooded
Lot Desc: CityLot, DeadEnd, FloodZone, NearPublicTransit, Landscaped
Misc
Other
Special Conditions: None
Security Features: SecuritySystemOwned, SecuritySystem, ClosedCircuitCameras, FireSprinklerSystem, SecurityGate, SecuredGarageParking, SmokeDetectors, SecurityLights
Other Rooms Info
Property Info
Section: 31
Class Type: SingleFamilyResidence
Property Sub Type: SingleFamilyResidence
Property Condition: NewConstruction
Construction Materials: Block, Stone, Stucco
Total Stories: 3
Foundation: Slab, StemWall
Room Info
Total Rooms: 13
Sqft Info
Sqft: 6,355
Bulding Area Sqft: 8,306
Living Area Units: SquareFeet
Living Area Source: PublicRecords
Tax Info
Tax Year: 2,025
Tax Lot: 6
Tax Legal Description: LOT 6 BLK C CHEROKEE PARK
Tax Block: C
Tax Annual Amount: 34624.73
Tax Book Number: 0002/0156
Unit Info
Utilities / Hvac
Heating: Central, Electric, NaturalGas, Zoned
Water Source: Public, Well
Sewer: PublicSewer
Cool System: CentralAir, Zoned, CeilingFans
Cooling: Yes
Heating: Yes
Utilities: CableConnected, ElectricityConnected, NaturalGasConnected, MunicipalUtilities, SewerConnected, WaterConnected
Waterfront / Water
View: Yes
View: Garden, Pool, TreesWoods
Directions
South on Osprey Ave, turn right on South Drive, home is on the left 1655 South Drive.This listing courtesy of Premier Sotheby's International Realty
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MLS IDX data last updated on 06-09-2026 2:00 AM EST.
If you have any questions on 1655 South Drive, Sarasota, Florida, please call David Shippey at 863-521-4517.
MLS# A4684423 located at 1655 South Drive, Sarasota, Florida is brought to you by David Shippey REALTOR®
1655 South Drive, Sarasota, Florida has 5 Beds, 5 Full Bath, and 4 Half Bath.
The MLS Number for 1655 South Drive, Sarasota, Florida is A4684423.
The price for 1655 South Drive, Sarasota, Florida is $5,900,000.
The status of 1655 South Drive, Sarasota, Florida is Active.
The subdivision of 1655 South Drive, Sarasota, Florida is Cherokee Park.
The home located at 1655 South Drive, Sarasota, Florida was built in 2026.