1585 South Drive, Sarasota, FL 34239
For Sale $2,275,000
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Listing Agent: Nick Gard
Agent Phone:
941-500-4273
Agent Email:
nick@gardheskett.com
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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. Sarasotas 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.
Built-in Features
Ceiling Fans(s)
Crown Molding
Eat-in Kitchen
Open Floorplan
Primary Bedroom Main Floor
Stone Counters
Walk-In Closet(s)
Wet Bar
Window Treatments
Taxes: $25.00
Tax Year: 2024
HOA Fee 1: $325.00
HOA Frequency 1: Annually
Condo Fee Frequency: Annually
French Doors
Bar Fridge
Dishwasher
Disposal
Dryer
Microwave
Range
Refrigerator
Tankless Water Heater
Touchless Faucet
Washer
Trees/Woods
Elementary School: Southside Elementary
Middle School: Brookside Middle
Junior High: Brookside Middle
High School: Sarasota High
MLS Area: 34239 - Sarasota/Pinecraft
Price per Square Feet: $823.08
Total Floors: 2
Water: Public
Lot Desc.: Corner Lot, City Limits, Landscaped, Level, Sidewalk, Paved
Construction: Wood Siding
Date Listed: 2025-09-24 12:57:15
Pool: No
Furnished: Negotiable
Garage Spaces: 2
Flooring: Tile, Wood
Roof: Shingle
Heating: Electric
Cooling: Central Air
Pets: Cats Ok, Dogs Ok, Yes
Sewer: Public Sewer
Listing Courtesy Of: Coldwell Banker Realty
nick@gardheskett.com
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. Sarasotas 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.
Property Details
Price: $2,275,000
Sq Ft: 2,764
($823 per sqft)
Bedrooms: 3
Bathrooms: 3
Partial Baths: 1
City: Sarasota
County: Sarasota
Type: Single Family Reside
Development: Cherokee Park 2
Acres: 0.38
Virtual Tour/Floorplan: View
Year Built: 1964
Listing Number: A4666035
Status Code: A-Active
Taxes: $25.00
Tax Year: 2024
Garage:
2
Furnishings: Negotiable
Pets Allowed: Cats OK, Dogs OK, Yes
Interior Features:
Built-in Features
Ceiling Fans(s)
Crown Molding
Eat-in Kitchen
Open Floorplan
Primary Bedroom Main Floor
Stone Counters
Walk-In Closet(s)
Wet Bar
Window Treatments
Financial Information:
Taxes: $25.00
Tax Year: 2024
HOA Fee 1: $325.00
HOA Frequency 1: Annually
Condo Fee Frequency: Annually
Exterior Features:
French Doors
Equipment:
Bar Fridge
Dishwasher
Disposal
Dryer
Microwave
Range
Refrigerator
Tankless Water Heater
Touchless Faucet
Washer
View:
Trees/Woods
School Information:
Elementary School: Southside Elementary
Middle School: Brookside Middle
Junior High: Brookside Middle
High School: Sarasota High
Additional Information:
MLS Area: 34239 - Sarasota/Pinecraft
Price per Square Feet: $823.08
Total Floors: 2
Water: Public
Lot Desc.: Corner Lot, City Limits, Landscaped, Level, Sidewalk, Paved
Construction: Wood Siding
Date Listed: 2025-09-24 12:57:15
Pool: No
Furnished: Negotiable
Garage Spaces: 2
Flooring: Tile, Wood
Roof: Shingle
Heating: Electric
Cooling: Central Air
Pets: Cats Ok, Dogs Ok, Yes
Sewer: Public Sewer
Map of 1585 South Drive, Sarasota, FL 34239
Listing Courtesy Of: Coldwell Banker Realty
nick@gardheskett.com