1739 CHEROKEE DRIVE Sarasota, FL $ 4,499,000
1739 CHEROKEE DRIVE
$ 4,499,000
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1739 CHEROKEE DRIVE

Sarasota, FL, 34239
$ 4,499,000
Bedrooms4 Baths4.1 Sq 4,538

Monthly Estimate*

$ 27,701

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Single Family Home for sale in Sarasota, FL

for $4,499,000 with 4 bedrooms and 4 full baths, 1 half bath. This 4,538 square foot home was built in 2009 on a lot size of 0.46.

Nestled along Cherokee Drive in the prestigious Cherokee Park neighborhood, this residence enjoys a premier setting on one of Sarasota’s most sought-after streets, renowned for its graceful oak canopy and classic west-of-the-trail charm. This residence embodies the perfect balance of modern architecture, natural materials, and tranquil privacy. Designed by award-winning architect Guy Peterson and constructed by master builder Pat Ball, the home delivers a rare combination of architectural pedigree and enduring craftsmanship. Positioned on a gracious, estate-sized parcel surrounded by lush greenery, the home’s U-shaped floor plan wraps around its showpiece, a 45-foot crystal-clear pool with integrated spa, creating a seamless indoor–outdoor living experience that defines the Sarasota lifestyle. Outside, the stone pathway leading to the custom mahogany front door sets a striking geometric tone. Inside, board-on-board architectural molded concrete accent walls, Santos Mahogany wood floors, and cypress-accent ceilings strike a natural harmony with the home’s sleek, modern lines. Floor-to-ceiling impact-rated Marvin windows flood the interior with light, framing tranquil views of the pool and landscape from nearly every room. The wide-open living and dining area, anchored by a wood-burning fireplace, sets the tone for elegant yet effortless entertaining. The chef’s kitchen features Wolf and Sub-Zero appliances, extensive custom maple cabinetry, and a seamless connection to both indoor and outdoor dining spaces. In the west wing, the expansive primary suite serves as a private retreat with walls of glass overlooking the grounds, complemented by an adjacent executive office for work-from-home convenience. The east wing hosts two en-suite guest bedrooms, each with sliding glass doors opening directly to the pool. A detached guest cabana offers a complete living area, kitchenette, and en-suite bedroom that is ideal for visitors, extended stays, or use as a private art studio or executive home office. Located within Cherokee Park, one of Sarasota’s most established and beloved neighborhoods, this home offers walking distance to Southside Elementary, minutes to Southside Village and downtown Sarasota, and easy access to Siesta Key Beach, just five streets away. The community is known for its family-friendly gatherings, tree-lined streets, and timeless Sarasota character.

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Single Family Active

Price

$ 4,499,000

Bedrooms

4

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 48,813

Style

Custom

Lot Size

0.46

Year Built

2009

Town/City

Sarasota

County/Region

Sarasota

MLS | Web ID

A4670822

Features
General
Sewer Public Sewer
Heating Electric
Cooling Central Air
Utilities BB/HS Internet Available Cable Connected Electricity Connected Natural Gas Connected Public Sewer Connected Water Connected
Roof Metal
Appliances Built-In Oven Cooktop Dishwasher Disposal Dryer Electric Water Heater Microwave Refrigerator Washer Water Filtration System
Zoning RSF1
Garage Spaces 2
Patio/Porch Features Covered Deck Patio
Architectural Style Custom
Pool Features Heated In Ground Lighting
Security Features Security System Smoke Detector(s)
Construction Materials Block Concrete Stucco
Pets Allowed Yes
Year Built 2009
View Pool
Levels One
Property Subtype Single Family Residence
Tax Year 2024
Ownership Fee Simple
Assoc Fee Paid Per Annually
County Sarasota
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name CHEROKEE PARK
Facing Direction South
Garage Y/N true
Other Structures Guest House
Total Rooms 5
Full Baths 4
Status Active
Directions From Downtown Sarasota head south on Osprey Avenue. Turn right onto Cherokee Drive 1739 Cherokee Drive is located midway down the street on the right-hand side.
High School Sarasota High
City SARASOTA
Senior Community Y/N false
MLS Area 34239 - Sarasota/Pinecraft
Lot Size Units Square Feet
Lot Size Square Feet 20000
Carport Y/N false
Listing Terms Cash Conventional
Spa Features Heated
Elementary School Southside Elementary
Land Lease Y/N false
Tax Annual Amount 48813
Middle/Junior High School Brookside Middle
Property Condition Completed
Additional Parcels Y/N false
Lease Considered Y/N true
Building Area Units Square Feet
Living Area Units Square Feet
Builder Name Pat Ball
Standard Status Active
Occupancy Type Owner
Tax Lot 4
Legal Description E 1/2 OF LOT 4 BLK F CHEROKEE PARK
Minimum Lease No Minimum
Water Access Y/N false
Additional Rooms Den/Library/Office Family Room Formal Dining Room Separate Formal Living Room Separate
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities Built-in Features Ceiling Fan(s) Primary Bedroom Main Floor Solid Wood Cabinets Split Bedroom Thermostat Tray Ceiling(s) Walk-In Closet(s) Window Treatments
Flooring Tile Hardwood
Furnished Y/N Unfurnished
Fireplace Features Wood Burning
Total Stories 1
Air Conditioning Y/N true
Heating Y/N true
Window Features Storm Window(s) Shutters Wood Frames
Fireplace Y/N true
Half Baths 1
Laundry Features Laundry Room
Total Bedrooms 4
Total Baths 5
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Exterior
Exterior Amenities Irrigation System Lighting Private Mailbox Sliding Doors Storage
Vegetation Mature Landscaping Trees/Landscaped
Parking Features Driveway Garage Door Opener
Lot Features Oversized Lot Sidewalk
Water Source Public
Lot Size Area 20000
Foundation Details Slab
Spa true
Building Area Total 5817
Lot Size Acres 0.46
Road Surface Type Paved
Private Pool true
Waterfront Y/N false
Covered Spaces 2
Road Frontage Type Street Paved
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* Excluded Features
List By
Coldwell Banker Realty

Broker

cole.collins@cbrealty.com

Email

Affordability Calculator

$31,769
Per Month
87%
13%
0%
Monthly Principal & Interest
$27,701
Monthly Property Taxes
$4,068
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% 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. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Sarasota High High School High School
Pricing History
DatePricePrice ChangeDescription
12/19/2025$4,499,000 Listed Price

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1739 CHEROKEE DRIVE, Sarasota, FL, 34239 is a Single Family Home for sale at $4,499,000 with 4,538 sqft and a lot size of 0.46. 1739 CHEROKEE DRIVE has 4 bedrooms, 4.1 baths, and was built in 2009. The property's zip code is 34239 which is in Sarasota, FL