Recently Viewed Properties
See This Home
Save This Listing
Close

$3,950,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,538 Sq. Ft.
See This Home
Save This Home
See This Home
Save This Home
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.

Full Property Details for 1739 Cherokee Dr

General

  • Sold For: $3,950,000
  • Taxes: $48,813 (2024)
  • Status: Closed
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4670822
  • Added to Site: 190 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 5
  • Interior Features: 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
  • Fireplace: Yes
  • Fireplace(s): Wood Burning
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer, Water Filtration System
  • Furnishings: Unfurnished
  • Flooring: Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Heated, In Ground, Lighting
  • Spa: Yes
  • Spa Description: Heated
  • Security/Safety: Security System, Smoke Detector(s)

Exterior

  • Exterior Features: Irrigation System, Lighting, Private Mailbox, Sliding Doors, Storage
  • Deck/Patio: Covered, Deck, Patio
  • Porch/Patio/Deck: Covered, Deck, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway, Garage Door Opener

Location

  • Area: 34239 - Sarasota/Pinecraft
  • County: Sarasota
  • Development Name: 34239 - Sarasota/Pinecraft
  • Subdivision: CHEROKEE PARK
  • Driving 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.
  • Direction Faces: South

School Information

  • Elementary School: Southside Elementary
  • Middle School: Brookside Middle
  • High School: Sarasota High

Community

  • Community Name: 34239 - Sarasota/Pinecraft
  • Association: Yes

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Water Connected

Structural Information

  • Architectural Info: Custom
  • Architectural Style: Custom
  • Builder: Pat Ball
  • Exterior Const.: Block, Concrete, Stucco
  • Roof: Metal
  • Windows: Storm Window(s), Shutters, Wood Frames
  • Stories/Levels: One
  • Square Feet: 4,538
  • Sq. Ft. Source: Public Records
  • Living Area: 4,538 Sq. Ft.
  • Year Built: 2009

Additional Structures

  • Other Structures: Guest House

Lot Features

  • Property View: Pool
  • Lot Size (Acres): 0.46
  • Lot Size (Sq. Ft.): 20,000
  • Lot Size: 20000
  • Frontage: Street Paved
  • Street/Road Desc.: Paved

Financial Considerations

  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Optional
  • Tax Amount: $48,813
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: E 1/2 OF LOT 4, BLK F, CHEROKEE PARK
  • Flood Zone Info: X
  • APN: 2039020031
  • Property ID: 2039020031
  • Block/Lot/Section: F

Meet the listing agent

Meet the listing agent
— 1739 Cherokee Dr —

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1739 Cherokee Dr

School District:Sarasota County School District
NameGradesDistance
Southside Elementary School, Sarasota, FL
1901 Webber Street, Sarasota, FL 34239
PK-50.2 mi
Brookside Middle School
3636 South Shade Avenue, Sarasota, FL 34239
6-80.8 mi
Sarasota High School
2155 Bahia Vista Street, Sarasota, FL 34239
9-121.2 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1739 Cherokee Dr

Date
Details
Price
Change
Source
4/20/2026
Sold
$3,950,000
-12.2%
MLS
11/05/2025
Listed
$4,499,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Similar Properties near 1739 Cherokee Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

847 Freeling Dr, Sarasota, FL 34242 - Photo 1
$3,950,000

847 Freeling Dr  Sarasota, FL 34242

  • Single Family
  • Active
  • 4
    Beds
  • 5
    Total Baths
  • 4,034
    Sq. Ft.
Listed by Compass Florida Llc
1642 Bahia Vista St, Sarasota, FL 34239 - Photo 1
$3,995,000

1642 Bahia Vista St  Sarasota, FL 34239

  • Single Family
  • Active
  • Updated 9 days ago
  • 4
    Beds
  • 5
    Total Baths
  • 3,809
    Sq. Ft.
Listed by Michael Saunders & Company
1905 Alta Vista St, Sarasota, FL 34236 - Photo 1
$3,975,000

1905 Alta Vista St  Sarasota, FL 34236

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 3,813
    Sq. Ft.
Listed by Michael Saunders & Company
6928 26th St W, Bradenton, FL 34207 - Photo 1
$3,900,000

6928 26th St W  Bradenton, FL 34207

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 3,601
    Sq. Ft.
Listed by Wagner Realty

Just Listed near 1739 Cherokee Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

5320 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Just Listed
$999,000

5320 Gulf of Mexico Dr  #101  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 21 minutes ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,323
    Sq. Ft.
Listed by Pettingell Professionals (941) 383-6411
3620 Fair Oaks Pl, Longboat Key, FL 34228 - Photo 1 Just Listed
$3,150,000

3620 Fair Oaks Pl  Longboat Key, FL 34228

  • Single Family
  • Active
  • Updated 13 hours ago
  • 3
    Beds
  • 6
    Total Baths
  • 3,666
    Sq. Ft.
Listed by Cindy Schatzle (941) 587-7556
711 Spanish Dr S, Longboat Key, FL 34228 - Photo 1 Just Listed
$435,000

711 Spanish Dr S  Longboat Key, FL 34228

  • Single Family
  • Active
  • Updated 21 minutes ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,327
    Sq. Ft.
Listed by Premier Sotheby's International Realty
1095 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Just Listed
$725,000

1095 Gulf of Mexico Dr  #102  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 1 day ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,392
    Sq. Ft.
Listed by Compass Florida Llc

Price Reduced near 1739 Cherokee Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

3530 Mistletoe Ln, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$200,000 (-7.42%)
$2,495,000

3530 Mistletoe Ln  Longboat Key, FL 34228

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,102
    Sq. Ft.
Listed by Pettingell Professionals (941) 383-6411
1125 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$50,000 (-5.89%)
$799,000

1125 Gulf of Mexico Dr  #101  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 2 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,172
    Sq. Ft.
Listed by Pettingell Professionals (941) 383-6411
2109 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$26,000 (-2.42%)
$1,049,000

2109 Gulf of Mexico Dr  #1303  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 2 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,463
    Sq. Ft.
Listed by The Leventhal Team (941) 383-6411
3060 Grand Bay Blvd, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$50,000 (-4.18%)
$1,145,000

3060 Grand Bay Blvd  #155  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 4
    Total Baths
  • 2,250
    Sq. Ft.
Listed by Bruce Myer Group (941) 383-6411

Recent Sales near 1739 Cherokee Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1729 Cherokee Dr, Sarasota, FL 34239 - Photo 1 Sold
$3,881,000

1729 Cherokee Dr  Sarasota, FL 34239

  • Single Family
  • Closed
  • 4
    Beds
  • 5
    Total Baths
  • 4,353
    Sq. Ft.
Listed by Michael Saunders & Company
Sold by Compass Florida Llc
1686 North Dr, Sarasota, FL 34239 - Photo 1 Sold
$4,090,000

1686 North Dr  Sarasota, FL 34239

  • Single Family
  • Closed
  • 5
    Beds
  • 7
    Total Baths
  • 6,128
    Sq. Ft.
Listed by Re/Max Alliance Group and Alliance Group Limited
Sold by Re/Max Alliance Group
1873 Rose St, Sarasota, FL 34239 - Photo 1 Sold
$3,775,000

1873 Rose St  Sarasota, FL 34239

  • Single Family
  • Closed
  • 5
    Beds
  • 5
    Total Baths
  • 4,550
    Sq. Ft.
Listed by Engel + Voelkers Sarasota
Sold by Greco Real Estate
2323 Okobee Dr, Sarasota, FL 34239 - Photo 1 Sold
$3,495,000

2323 Okobee Dr  Sarasota, FL 34239

  • Single Family
  • Closed
  • Updated 12 days ago
  • 4
    Beds
  • 5
    Total Baths
  • 3,497
    Sq. Ft.
Listed by Re/Max Alliance Group
Sold by Michael Saunders & Company

1739 Cherokee Drive, Sarasota, FL 34239 (MLS# A4670822) is a Single Family property that was sold at $3,950,000 on April 20, 2026. This property was listed by Cole Collins from our Siesta Key Office.Want to learn more about 1739 Cherokee Drive? Do you have questions about finding other Single Family real estate for sale in Sarasota? You can browse all Sarasota real estate or contact a Coldwell Banker agent to request more information.