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1729 Cherokee Drive, Sarasota, FL 34239

$4,150,000
  • 1729 Cherokee Drive, Sarasota, FL 34239 Main Photo

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Pending
BEDS4 BATHS4 full 1 partial SQUARE FEET4,353 MLS#A4682051
STATUSPending PROPERTY TYPEResidential - Single Family SUBDIVISIONCHEROKEE PARK 2

Property Description

Priced to sell. Recipient of eleven awards, including Residential Design and Build Design Excellence and Home of the Year by SRQ Magazine, this exceptional residence is the result of a thoughtful collaboration between Jonathan Parks Architect and Michael A. Gilkey Inc landscape designer. Located in one of Sarasota's oldest and most established neighborhoods, the home seamlessly blends a traditional 1920s architectural vocabulary with a modern appreciation for simplicity and precision. The result is a sophisticated four-bedroom residence with a British Colonial sensibility-elegant, timeless, and thoughtfully designed for today's lifestyle. Set on an unusually large 20,000-square-foot lot and located outside of any flood zone, the property offers a rare sense of space and privacy. An artistic pool and a series of designated outdoor living areas, framed by curated garden vignettes, complete this tranquil retreat. The striking foyer welcomes you with understated elegance, gleaming wood floors, and an immediate sense of refinement. Walls of glass define the main living spaces, filling the interior with natural light and highlighting the fireplace as a focal point. While the classic elements of a traditional home remain-stucco exterior, white roof, and ironwork details-the overall aesthetic is contemporary and quietly confident. Large windows and an open floor plan are designed to maximize light and create a seamless connection to the outdoors. A spacious screened patio offers an inviting setting for both relaxation and al fresco dining. Mature Mahoe trees, native to South Africa, line the exterior and rise gracefully to the level of the home's high windows, enhancing privacy and serenity. The primary suite occupies its own private wing on the first floor, complete with a secluded courtyard, while an ensuite guest bedroom and office balance the opposite wing. Upstairs, two additional ensuite bedrooms each enjoy private balconies overlooking the lush grounds. Throughout the home, a Zen-like sense of peace and tranquility prevails-a true sanctuary of thoughtful design and quiet luxury.

1729 Cherokee Drive | MLS# A4682051

This single family home located at 1729 Cherokee Drive, Sarasota, FL 34239 is currently listed for sale with an asking price of $4,150,000. This property was built in 2008 and has 4 bedrooms and 4 full and 1 partial baths with 4353 sq. ft. Cherokee Drive is located in the CHEROKEE PARK 2 subdivision. Search CHEROKEE PARK 2 real estate on dparsons.realty100.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air, Mini-Split Unit(s)
Fenced: Yes
Garage: 3 car attached
Heating: Central, Electric, Zoned
Home Style: Custom
Lot Size: 0.46 Acres
Roof Type: Concrete, Tile
Stories: 2.0
Taxes: $24,980
Year Built: 2008

Amenities

Built-in Features
Ceiling Fans(s)
High Ceilings
Kitchen/Family Room Combo
Primary Bedroom Main Floor
Solid Surface Counters
Solid Wood Cabinets
Split Bedroom
Stone Counters
Thermostat
Vaulted Ceiling(s)
Walk-In Closet(s)
Window Treatments
Balcony
Courtyard
French Doors
Lighting
Outdoor Grill
Outdoor Kitchen
Private Entrance
Private Yard
Rain Gutters

Feature Descriptions

Additional Rooms: Den/Library/Office, Great Room, Inside Utility
Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer, Water Purifier, Water Softener
Community Features: Street Lights
Days on Site: 69
Directions: From S Osprey Ave, turn onto Cherokee Dr and house will be on the right side.
Exterior: Block, Stucco
Fencing: Fenced
Fireplace: Gas, Living Room, Outside, Wood Burning
Fireplace Y/N: Yes
Flood Zone Code: X
Flooring: Ceramic Tile, Hardwood, Other
Foundation: Slab
Home Warranty Y/N: No
Listing Terms: Cash, Conventional
Lot: City Limits, Landscaped, Near Public Transit, Oversized Lot, Private, Sidewalk, Paved
Lot Dimensions: 0.46
Number of Pets: 10+
Other Equipment: Irrigation Equipment, Private Entrance, Private Yard, Generator
Ownership: Fee Simple
Parking: Driveway, Garage Door Opener, Oversized
Parking Notes: Driveway, Garage Door Opener, Oversized
Patio/Porch: Covered, Patio, Porch, Screened
Pets Allowed: Yes
Pets Size: Extra Large (101+ Lbs.)
Pool: Heated, In Ground, Lighting, Tile
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Security: Security System, Smoke Detector(s)
Sewer: Public Sewer
Showing Instructions: Key/Agent, Listing Agent Must Accompany, See Remarks, ShowingTime
Spa: Heated, In Ground
Special Sale Provisions: None
Swimming Pool: Yes
Utilities: Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Sprinkler Well, Water Connected
Vegetation: Mature Landscaping, Trees/Landscaped
Water: Public
Water Access Y/N: No
Windows: Window Treatments
Zoning: RSF1

Local Schools

High School: Sarasota High
Middle School: Booker Middle
Elementary School: Southside Elementary

Listed By / Shown By

Listed By

Agency Name: MICHAEL SAUNDERS & COMPANY
Agency Contact: 941-951-6660

Shown By

Agent Name: Debra Parsons
Agent Phone: Cell: (754) 234-2951
Agency Title: Realty 100

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Estimated Payment

$ 12,528.18 per month $9,236.10 Principal & Interest $2,081.67 Property Tax $1,210.42 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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 on this site was last updated 04/23/2026. The listing information on this page last changed on 04/23/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 04/23/2026 12:00:33 AM EST) or Miami MLS (last updated Wed 04/22/2026 11:48:44 PM EST) or Stellar MLS (last updated Wed 04/22/2026 11:44:12 PM EST) or Beaches MLS (last updated Wed 04/22/2026 11:58:05 PM EST). Real estate listings held by brokerage firms other than Realty 100 may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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