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SARASOTA, FL 34239 1585 SOUTH DRIVE

$2,275,000

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Presented By: COLDWELL BANKER REALTY with 941-388-3966. - 941-388-3966
  • MLS# A4666035
  • 09/24/2025
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Disclaimer: The information contained in this listing has not been verified by Homepride Group at EXP Realty and should be verified by the buyer.
  • Beds • 3
  • Full/Half Baths • 3 / 1
  • SQFT • 2,764
  • Garage • 2

Home Details

Welcome to 1585 South Drive, a timeless cottage-style residence in the beloved West of Trail community of Cherokee Park. Thoughtfully updated and rich with character, this home seamlessly blends historic charm with modern comfort. Refinished white oak floors, abundant natural light, stylish finishes, and a gracious, contemporary layout make it truly move-in ready. Elevated more than 10 feet above sea level yet just three houses from the bay, the home enjoys both beauty and peace of mind on a corner lot at the quiet end of the street. From the inviting brick front porch, step into a foyer with custom board-and-batten detailing. To the right, a generous living room encourages gathering; to the left, a versatile office, den, or sitting room is tucked behind sliding doors for a quieter retreat. Expansive windows frame leafy views and bathe the interiors in light. At the heart of the home, the oversized kitchen impresses with a large central island, abundant counter space, walk-in pantry, wet bar, and KitchenAid appliances. The adjoining dining room opens to the backyard and screened porch, creating seamless indoor-outdoor living. The primary suite is privately situated on the main level, offering a spacious walk-in closet, serene ensuite bath, and direct screened porch access. Nearby, a second bedroom with its own hall bath serves perfectly as a guest suite, children’s room, or home office. Upstairs, a private retreat includes a large bedroom with dormer windows, built-in window seats, an ensuite bath, and extensive storage. Additional highlights include a recently remodeled marble powder room, a well-equipped laundry room, an irrigation well, and an attached two-car garage. The generously sized lot offers ample room for a pool, guest house, or future expansion. Sarasota's West of Trail neighborhoods are coveted for their proximity to Sarasota Memorial Hospital, downtown, and the sugar white sands of Siesta Key. Cherokee Park is perhaps the most prized of these, celebrated for its stately homes, wide tree-lined streets with sidewalks, walkability to Southside Village and Southside Elementary, and cherished traditions — from bustling Halloweens to twinkling luminaries and carriage rides at the holidays. While the surrounding streets boast their share of impressive new construction, this well-proportioned and well-preserved original stands apart for its enduring charm, turnkey livability, and exceptional value. Designer furnishings by Pecky Interiors are optionally available.
Presented By: COLDWELL BANKER REALTY with 941-388-3966. - 941-388-3966

Interior Features for 1585 SOUTH DRIVE

Bedrooms

Total Bedrooms3

Bathrooms

Half Baths1
Total Baths4

Other Interior Features

LivingAreaSourcepublic records
Air Conditioning Y/NYes
Fireplace Y/NNo
Flooringtile, hardwood
Furnished Y/Nnegotiable
Heating Y/NYes
Interior Amenitiesbuilt-in features, ceiling fan(s), crown molding, eating space in kitchen, open floorplan, primary bedroom main floor, stone counters, walk-in closet(s), wet bar, window treatments
Laundry Featuresinside, laundry room
Total Stories2

General for 1585 SOUTH DRIVE

Additional Parcels Y/NNo
Appliancesbar fridge, dishwasher, disposal, dryer, microwave, range, refrigerator, tankless water heater, touchless faucet, washer
Architectural Stylecape cod, coastal, cottage, traditional
Assoc Fee Paid Perannually
Attached Garage Yes
Building Area Unitssquare feet
Carport Y/NNo
Citysarasota
Construction Materialswood siding
Coolingcentral air
Countysarasota
Directionshead south on osprey ave. turn right on south drive. home is near the end of the street on the right.
DockY/NNo
Elementary Schoolsouthside elementary
Facing Directionsouth
Flood Zone Codex500
Flood Zone Code X500Y
Full Baths3
Garage Spaces2
Garage Y/NYes
HOAYes
HOA Fee$325
Heatingelectric
High Schoolsarasota high
Land Lease Y/NNo
Lease Considered Y/NYes
Legal Descriptionbeg ne cor lot 1 blk c th s 150 ft th w 100 ft th n 150 ft th w 42 ft th n 42 ft th s 56-19 50.47 ft th w 68-45 e 38.62 ft th s 89-58 e 63.99 ft to pob being part of replat of cherokee park
Levelstwo
Living Area Unitssquare feet
Lot Size Square Feet16433
Lot Size Unitssquare feet
MLS Area34239 - sarasota/pinecraft
Middle/Junior High Schoolbrookside middle
Minimum Lease1 week
ModificationTimestamp2025-09-28t19:05:04.527z
Monthly HOA Amount27.08
New ConstructionNo
Occupancy Typeowner
Ownershipfee simple
Patio/Porch Featurescovered, deck, front porch, rear porch, screened
Pets Allowedcats ok, dogs ok, yes
Property Conditioncompleted
Property Subtypesingle family residence
Property Typeresidential
Roofshingle
STELLAR_InLawSuiteYNNo
Senior Community Y/NNo
Sewerpublic sewer
Standard Statusactive
Statusactive
Subdivision Namecherokee park 2
Tax Annual Amount25810.85
Tax Lot1
Tax Year2024
Total Rooms7
Utilitiescable connected, electricity connected, natural gas connected, sewer connected, water connected
Viewtrees/woods
Virtual TourClick here
Water Access Y/NNo
Water View Y/NNo
Year Built1964
Zoningrsf1

Exterior for 1585 SOUTH DRIVE

Building Area Total3678
Covered Spaces2
Exterior Amenitiesfrench doors, irrigation system
Foundation Detailsblock, crawlspace, stem wall
Lot Featurescorner lot, city lot, landscaped, level, sidewalk
Lot Size Acres0.38
Lot Size Area16433
Private PoolNo
Road Frontage Typestreet paved
Road Responsibilitypublic maintained road
Road Surface Typepaved, asphalt
Vegetationmature landscaping, oak trees, trees/landscaped
Water Sourcepublic
Waterfront Y/NNo

Additional Details

Price History

Schools

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

Steven Pugh

Broker Associate | Team Leader
Price $2,275,000
MLS#A4666035
List Date 09/24/2025
Property Type Single Family
Phone (407) 873-0057
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