1729 Cherokee Drive, Sarasota, FL 34239
For Sale $4,450,000
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Contact the Listing Agent directly:
Listing Agent: Kim Ogilvie
Agent Phone:
941-951-6660
Agent Email:
kimogilvie@michaelsaunders.com
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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.
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
Taxes: $24.00
Tax Year: 2025
Balcony
Courtyard
French Doors
Lighting
Outdoor Grill
Outdoor Kitchen
Private Entrance
Private Yard
Rain Gutters
Built-In Oven
Cooktop
Dishwasher
Disposal
Dryer
Gas Water Heater
Microwave
Range
Range Hood
Refrigerator
Washer
Water Purifier
Water Softener
Trees/Woods
Elementary School: Southside Elementary
Middle School: Booker Middle
Junior High: Booker Middle
High School: Sarasota High
MLS Area: 34239 - Sarasota/Pinecraft
Price per Square Feet: $1,022.28
Total Floors: 2
Water: Public
Lot Desc.: City Limits, Landscaped, Near Public Transit, Oversized Lot, Private, Sidewalk, Paved
Construction: Block, Stucco
Date Listed: 2026-02-12 21:45:26
Pool: Yes
Pool Type: Heated, In Ground, Lighting, Tile
Private Spa: Yes
Furnished: Unfurnished
Windows: Window Treatments
Parking: Driveway, Garage Door Opener, Oversized
Garage Spaces: 3
Flooring: Ceramic Tile, Hardwood, Other
Roof: Concrete, Tile
Heating: Central, Electric, Zoned
Cooling: Central Air, Mini-Split Unit(S)
Pets: Yes
Sewer: Public Sewer
Listing Courtesy Of: Michael Saunders & Company
kimogilvie@michaelsaunders.com
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.
Property Details
Price: $4,450,000
Sq Ft: 4,353
($1,022 per
sqft)
Bedrooms: 4
Bathrooms: 4
Partial Baths: 1
City: Sarasota
County: Sarasota
Type: Single Family Reside
Development: Cherokee Park 2
Acres: 0.46
Year Built: 2008
Listing Number: A4682051
Status Code: A-Active
Taxes: $24.00
Tax Year: 2025
Garage:
3
Furnishings: Unfurnished
Pets Allowed: Yes
Interior Features:
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
Financial Information:
Taxes: $24.00
Tax Year: 2025
Exterior Features:
Balcony
Courtyard
French Doors
Lighting
Outdoor Grill
Outdoor Kitchen
Private Entrance
Private Yard
Rain Gutters
Equipment:
Built-In Oven
Cooktop
Dishwasher
Disposal
Dryer
Gas Water Heater
Microwave
Range
Range Hood
Refrigerator
Washer
Water Purifier
Water Softener
View:
Trees/Woods
School Information:
Elementary School: Southside Elementary
Middle School: Booker Middle
Junior High: Booker Middle
High School: Sarasota High
Additional Information:
MLS Area: 34239 - Sarasota/Pinecraft
Price per Square Feet: $1,022.28
Total Floors: 2
Water: Public
Lot Desc.: City Limits, Landscaped, Near Public Transit, Oversized Lot, Private, Sidewalk, Paved
Construction: Block, Stucco
Date Listed: 2026-02-12 21:45:26
Pool: Yes
Pool Type: Heated, In Ground, Lighting, Tile
Private Spa: Yes
Furnished: Unfurnished
Windows: Window Treatments
Parking: Driveway, Garage Door Opener, Oversized
Garage Spaces: 3
Flooring: Ceramic Tile, Hardwood, Other
Roof: Concrete, Tile
Heating: Central, Electric, Zoned
Cooling: Central Air, Mini-Split Unit(S)
Pets: Yes
Sewer: Public Sewer
Map of 1729 Cherokee Drive, Sarasota, FL 34239
Listing Courtesy Of: Michael Saunders & Company
kimogilvie@michaelsaunders.com