• Home
  • What Makes a “Waterfront Specialist”?
  • Buyers
    • Buying or Selling a Luxury Home
    • What You Should Know About Short Sales
    • What You Should Know As a Buyer When Attending an Auction
    • Who To Consider When Buying a Home?
  • Sellers
    • Buying or Selling a Luxury Home
    • What to Look for in a Realtor When Selling Your Home?
    • What You Should Know About Bank Owned Properties
    • What You Should Know About Short Sales
  • About Us
    • Contact Us
    • Privacy Policy
  • Testimonials

The Gary Cardillo Group

Your Punta Gorda Waterfront Specialists

  • Office Listings
  • Homes for Sale
    • Port Charlotte Homes
    • Punta Gorda Homes
    • Punta Gorda Isles Homes
    • Burnt Store Isles Homes
    • Englewood Homes
    • North Port Homes
    • Sarasota Homes
    • Venice Homes
    • Waterfront Homes
      • Sailboat Homes
      • Canal Homes
    • Newly Listed Homes
  • Condos for Sale
    • Port Charlotte Condos
    • Punta Gorda Condos
    • Punta Gorda Isles Condos
    • Burnt Store Isles Condos
    • Englewood Condos
    • North Port Condos
    • Sarasota Condos
    • Venice Condos
    • Waterfront Condos
      • Sailboat Condos
      • Canal Condos
    • Newly Listed Condos
  • Land for Sale
    • Port Charlotte Lots
    • Punta Gorda Lots
    • Punta Gorda Isles Lots
    • Burnt Store Isles Lots
    • Englewood Lots
    • North Port Lots
    • Venice Lots
    • Waterfront Lots
      • Sailboat Lots
      • Canal Lots
    • Newly Listed Lots
  • Search the MLS
  • Blog
  • Contact Us

Listing Details for MLS #A4684423 - 1655 South Drive, Sarasota, Fl 34239

Inquire

Residential Property - Single Family Residence in Sarasota

Listing Price: $5,900,000Days on Market: 3

Description of Property

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 home’s 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.The average asking price for a 5 bedroom/5 bath single family residence in this Zip code is $4,726,333. This single family residence is listed at about 125% of the average asking price. There are 3 5 bedroom/5 bath homes between $5,200,000 and $6,600,000 currently listed for sale in this Zip code. See other listings like this one »

MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
MLS #A4684423 - SARASOTA
 

Property Details At A Glance

  • Virtual Tour

Property Type: Residential
Property Use or Sub Type: Single Family Residence
City: Sarasota
County: Sarasota
Subdivision: Cherokee Park
Bedrooms: 5
Bathrooms: 5
Half Baths: 4
Sq. Ft. Gross: 8,306
Sq. Ft. Living Area: 6,355
Cost per (heated) sqare foot: $928
Year built: 2011
Annual Tax: $34,625

HOA Fee: $325 Annually
Taxes and fees can change periodically, and other fees may apply. Please check with your Realtor for more details.

Interior Features: Window Treatments
Appliances: Washer

Fireplace: Yes
Fireplace Features: Outside
Window Features: Thermal Windows

Additional Rooms: Storage Rooms

Flooring: Hardwood

Laundry Features: Upper Level

Green Features

Indoor Air Quality: Ventilation

Green Energy Features: Windows

Green Landscaping: Fl. Friendly/Native Landscape

GreenWater Conservation: Whole House Water Purification

Schools

Elementary School: Southside Elementary
Middle/Junior High School: Brookside Middle
High School: Sarasota High

Pool & Waterfront Info

Private Pool: Yes
Pool Features: Outside Bath Access
Spa Features: Other

Exterior & Construction

Architectural Style: Other
Construction: Stucco
Foundation: Stem Wall
Roof: Tile
Exterior Features: Sliding Doors
Garage: Yes
Garage Spaces: 3
Parking Features: Ground Level
Floors Total: 3
Floors in Unit: Three Or More
Cooling: Zoned
Heating & Fuel: Zoned
Patio & Porch Features: Side Porch
Security Features: Smoke Detector(s)
View: Trees/Woods
Fencing: Stone

Utilities: Water Connected
Sewer: Public Sewer
Water Source: Well

Lot Information

Lot Features: Street Dead-End
Lot Size (acres): 0.34
Lot Size (sq. ft.): 15,000 square feet
Road Frontage: Street Paved
Front Exposure: South

Legal Description & Other Information

Financing Available: Conventional
Parcel Number: 2039020017
Zoning: RSF1
Pets Allowed/Pet Policies: Yes
Tax Legal Desc.: LOT 6 BLK C CHEROKEE PARK
Section: 31
Range: 18

 

Map

 

Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY. The information relating to real estate for sale on this website comes in part from the My Florida Regional MLS DBA Stellar MLS. This information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS.

Contact The Cardillo Group today about this listing:

    Contact Us Today!

    Your Name (required)

    Your Email (required)

    MLS Number (required)

    Your Message (required)

    How Can We Help You?






      Shop for Real Estate

      • Single-Family Homes for Sale
        • Port Charlotte Homes
        • Punta Gorda Homes
        • Punta Gorda Isles Homes
        • Burnt Store Isles Homes
        • Englewood Homes
        • North Port Homes
        • Sarasota Homes
        • Venice Homes
        • Waterfront Homes
          • Sailboat Homes
          • Canal Homes
        • Newly Listed Homes
      • Condos for Sale
        • Port Charlotte Condos
        • Punta Gorda Condos
        • Punta Gorda Isles Condos
        • Englewood Condos
        • Burnt Store Isles Condos
        • North Port Condos
        • Sarasota Condos
        • Venice Condos
        • Waterfront Condos
          • Sailboat Condos
          • Canal Condos
        • Newly Listed Condos
      • Lots & Land for Sale
        • Port Charlotte Lots
        • Punta Gorda Lots
        • Punta Gorda Isles Lots
        • Burnt Store Isles Lots
        • Englewood Lots
        • North Port Lots
        • Venice Lots
        • Waterfront Lots
          • Sailboat Lots
          • Canal Lots
        • Newly Listed Lots
      • RE/MAX Harbor Realty Office Listings

      Search The MLS

      To search for real estate listed for sale in the MLS, please use our MLS Search Form »

      Search By MLS Listing Number

      MLS #:
      For multiple MLS numbers, separate numbers by a comma: e.g., C7005869, C7015140

      Recent Posts

      • The Angels Who Walk Among Us
      • 2026 January/February Newsletter
      • A Different Kind of Gift
      • A Season That Reminds Us What Truly Matters
      • From Summer Dreams to Fall Blessings

      Search The Blog

      Share

      Twitter
      facebook

      Contact The Gary Cardillo Group

      By email: Info@FLwaterfrontliving.com
      Mobile: 941-916-0939
      Address: RE/MAX Harbor Realty
      2815 Tamiami Trail
      Punta Gorda, FL 33950

      About The Gary Cardillo Group

      Gary Cardillo, Realtor While most people would like to talk about themselves, Gary and Gail have always put their clients first, and their diverse backgrounds have provided their clients an unparalleled level of service and knowledge throughout the past years.
        » Read More...

      Explore Real Estate for Sale

      • Search the MLS
      • Condos for Sale
      • Lots & Land for Sale
      • Single-Family Homes for Sale

      Read Our Blog

      • Buying Real Estate
      • Community Information
      • Events & Activities
      • Selling Real Estate
      The Gary Cardillo Group • RE/MAX Harbor Realty
      2815 Tamiami Trail • Punta Gorda, FL 33950
      941-916-0939
      garycardillo@wesellpg.com

      Copyright © 2011-2026 · The Gary Cardillo Group
      Site designed and managed by Tropical Web Works 104.156.48.242

      Back to Top
      Contact Us