Skip to main content
Back to Search Results
|

1585 South Drive, Sarasota, FL 34239

Show All 44 Photos
For Sale

$2,275,000

3 beds • 3 baths • 1 half baths • 2,764 sqft

Estimated Payment

$      /mo. †

APR for 30 years

Change Loan Terms

  • Single Family Detached
    Property type

  • Newly Listed
    Time on Century 21

  • $823.08
    Price per square foot

  • Over 50 Years Old
    Age

Explore this Property

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.
MLS# A4666035

Courtesy Of Coldwell Banker

(941) 388-3966

Open Houses

September

28

Sunday

In Person

Sunday, September 28, 2025

12:00PM - 3:00PM

Property Features

  • Age
    Over 50 Years Old
  • Amenities
    Wet Bar, Ceiling Fan
  • Appliances
    Dishwasher, Dryer, Garbage Disposer, Microwave, Range, Refrigerator, Washer
  • Architecture Style
    Cape Cod
  • Exterior Type
    Wood Siding
  • Floor Covering
    Tile, Wood
  • Lot Size
    0.38 Acres
  • Rooms
    Dining Room, Family Room, Kitchen, Living Room

Map and Directions

Directions to 1585 South Drive, Sarasota, FL 34239

Home seller CENTURY 21 Integra

Get to know the neighborhood. A local affiliated CENTURY 21 office will help you set up tours, give advice, and negotiate with sellers.

CENTURY 21 Integra

(727) 826-1522
Learn More About Us

Mortgage Calculator

$
$ %
Loan Term
%
Invalid number

$ /year
$ /year
$ /month

Monthly Payment Breakdown

  • Principle and Interest
    $0
  • Property Taxes
    $0
  • Hazard Insurance
    $0
  • Private Mortgage Insurance
    $0
  • HOA Dues
    $0
  • Total Monthly Payment:
    $0

Calculators provided for estimating purposes only. Consult with your lender to determine precise payment requirements.

An Equal Opportunity Company

Copyright © 2025 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified. Information being provided is for consumers' 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 being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data powered by Attom Data Solutions. Copyright© 2025. Information deemed reliable but not guaranteed.

This information is provided for general informational purposes only and should not be relied on in making any home-buying decisions. School information does not guarantee enrollment. Contact a local real estate professional or the school district(s) for current information on schools. This information is not intended for use in determining a person's eligibility to attend a school or to use or benefit from other city, town or local services.

† Based on a 30-year fixed rate of 3.38% 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. Interest rates are also subject to credit and property approval based on secondary market guidelines. The rates shown are based on average rates for our best qualified customers. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.