Sarasota MLS Listings

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$2,275,000
19 Days On Site

1585 SOUTH DRIVE
SARASOTA, FL 34239

For Sale|Single Family Residence|Active
3
Beds
4
Total Baths
3
Full Baths
1
Partial Bath
2,764
SqFt
$823
/SqFt
1964
Built
Subdivision:
CHEROKEE PARK 2
County:
Sarasota
Call Now: 941-265-2455
Is this the listing for you? We can help make it yours.
941-265-2455
1585 SOUTH DRIVE1585 SOUTH DRIVE1585 SOUTH DRIVE1585 SOUTH DRIVE
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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. 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.

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Listing Snapshot
Price 
$2,275,000
Days On Site 
19 Days
Bedrooms 
3
Inside Area (SqFt) 
2,764 sqft
Total Baths 
4
Full Baths 
3
Partial Baths 
1
Lot Size 
0.38 Acres
Year Built 
1964
MLS® Number 
A4666035
Status 
Active
Property Tax 
$25,810.85
HOA/Condo/Coop Fees 
$27.08 monthly
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
2 weeks agoListing updated with changes from the MLS®
3 weeks agoListing first seen on site
General Features
Acres 
0.38
Attached Garage 
Yes
Direction Faces 
South
Foundation 
Block
Garage 
Yes
Garage Spaces 
2
Levels 
Two
Number Of Stories 
2
Parking 
Attached
Pets 
Cats OKDogs OKYes
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
SqFt Total 
3678
Style 
Cape CodCoastalCottageTraditional
Utilities 
Cable AvailableNatural Gas AvailableCable ConnectedElectricity ConnectedNatural Gas ConnectedSewer ConnectedWater Connected
Water Source 
Public
Zoning 
RSF1
Interior Features
Appliances 
Bar FridgeDishwasherDisposalDryerMicrowaveRangeRefrigeratorTankless Water HeaterWasher
Basement 
Crawl Space
Cooling 
Central Air
Flooring 
TileWood
Furnished 
Negotiable
Heating 
Electric
Interior 
Built-in FeaturesCrown MoldingEat-in KitchenOpen FloorplanStone CountersWalk-In Closet(s)Wet Bar
Laundry Features 
InsideLaundry Room
Bedroom 2 
Level - First
Bedroom 3 
Level - Second
Dining Room 
Level - First
Family Room 
Level - First
Kitchen 
Level - First
Living Room 
Level - First
Master Bedroom 
Level - First
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Exterior Features
Construction Details 
Wood Siding
Lot Features 
Corner LotLandscapedLevelPaved
Patio And Porch 
CoveredDeckFront PorchRear PorchScreened
Roof 
Shingle
View 
Trees/Woods
Waterview 
Trees/Woods
Community Features
Association Dues 
325
HOA Fee Frequency 
Annually
MLS Area 
34239 - Sarasota/Pinecraft
Roads 
Asphalt
Township 
36S
Schools
School District
Unknown
Elementary School
Southside Elementary
Middle School
Brookside Middle
High School
Sarasota High
Listing courtesy of COLDWELL BANKER REALTY 9415004273



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2025, Stellar MLS.
Last checked: 2025-10-14 12:00 AM EDT

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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