1774 Cherokee Dr

3,821 Sq. Ft.
$993 / Sq. Ft.
3,821
Sq. Ft.
$993
per Sq. Ft.

Description

Welcome to this rarely available Cape Cod–style residence, comprised of a masterfully renovated main house and separate luxe guest house poised on an expansive 20,000 sq. ft. lot in Sarasota’s prestigious Cherokee Park. Elevated 23 feet above sea level and nestled on a wide, tree-lined street in the coveted West of Trail district—within the top-rated Southside school zone—this 4-bedroom, 3 full/2 half bath +office private compound blends timeless architecture with designer-curated sophistication....Welcome to this rarely available Cape Cod–style residence, comprised of a masterfully renovated main house and separate luxe guest house poised on an expansive 20,000 sq. ft. lot in Sarasota’s prestigious Cherokee Park. Elevated 23 feet above sea level and nestled on a wide, tree-lined street in the coveted West of Trail district—within the top-rated Southside school zone—this 4-bedroom, 3 full/2 half bath +office private compound blends timeless architecture with designer-curated sophistication. A stately front porch framed by lush landscaping and classic brick walkway introduces the home with understated grandeur. Handcrafted, glass-inlaid iron double doors open to a refined foyer where natural light, elegant millwork, and soaring 10-foot ceilings set the tone for the bespoke interiors beyond. Inside, original hardwood floors, designer lighting by Arteriors, Eichholtz, and Kelly Wearstler, and high-end finishes selected by Chelsea Dunbar of Blu Interiors create a sense of warmth and refinement throughout. The quartz-clad chef’s kitchen is as functional as it is beautiful, featuring a Wolf natural gas range, KitchenAid French-door refrigerator, ample pantry space, and custom cabinetry—perfectly suited for both intimate dining and entertaining. Anchored by a wood-burning fireplace, the main living and dining spaces flow seamlessly outdoors to an inviting Pennsylvania bluestone patio, low-maintenance Astroturf lawn, and wrap-around Brazilian teak deck—an idyllic setting for year-round enjoyment. The serene first floor primary suite is a private retreat showcasing three custom-designed walk-in closets and a spa-inspired bath with marble finishes, dual vanities, heated towel bar, and a zero-entry shower with body sprays. Ascend the custom staircase to find 2 tailored guest retreats with spa-like bath, each offering serene views and thoughtfully appointed details for ultimate comfort and privacy. Throughout the home, custom wallcoverings by Phillip Jeffries, Scalamandré, and Élitis add layers of texture and artistry, while upgraded systems—including a surround sound system, six climate zones, and multiple laundry areas—enhance everyday comfort. Resort-style living continues outdoors with a 9-foot-deep pool framed by classic Bevolo gas lanterns and an extraordinary luxury guest house built in 2016. This refined space includes an entertaining area with custom built-ins, full bar, refrigerator drawers, Scotsman icemaker, private guest suite, 1.5 baths, gym, and an outdoor teak shower. The fully equipped outdoor kitchen features a natural gas Lynx grill, XL Green Egg, quartzite prep counters, and a covered gazebo ideal for al fresco dining. All impact doors and windows, cedar shake roof, and Hardie Board siding add to the beauty and durability of the home. Completing this exceptional estate is an oversized 2.5-car detached garage and secure, fully fenced grounds with electric fence. Enjoy tree-lined streets with sidewalks and a true sense of community, all just a short stroll or golf cart ride to Southside Village where residents enjoy boutique shops, Morton’s Gourmet Market, cafés, and top-rated restaurants, and minutes from downtown Sarasota and Siesta Key Beach. This is refined Gulf Coast living—where timeless architecture meets effortless luxury in one of Sarasota’s most treasured neighborhoods.
  1. Listed by Lenore Treiman • Brokerage DRE #2029530 • MICHAEL SAUNDERS & COMPANY
    P: (941)-356-9642 C: (941)-356-9642 lenoretreiman@michaelsaunders.com

Property Details for 1774 Cherokee Drive

Architectural Style
Cape Cod
Subdivision Name
CHEROKEE PARK 2
Township
36
Garage Spaces
2
Waterfront
No
LISTING UPDATED: 01/29/2026 01:16 PM

Property Details for 1774 Cherokee Drive

StatusActive
MLS #A4669184
Days on Market110
Taxes$17,603 / year
HOA Fees$375 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1982
Lot Size0.46 AC / 20,000 SF
CountySarasota County

Location

Listing Courtesy of MICHAEL SAUNDERS & COMPANY, Lenore Treiman
Add your commute

Building Information for 1774 Cherokee Drive

Stories-Year Built1982Building Size-Lot Size0.46 AC / 20,000 SF

Payment Calculator

$19,994 per month

30 year fixed, 6.15% Interest

Principal and Interest

$18,496

Property Taxes

$1,467

HOA Dues

$31

The Payment Calculator is for illustrative purposes only.

Property Information for 1774 Cherokee Drive

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 5131.0
  • Building Area Units: Square Feet
  • Direction Faces: North
  • Directions: Located on the corner of Cherokee Drive and Osprey Avenue.
  • Elementary School: Southside Elementary
  • Middle Or Junior School: Brookside Middle
  • High School: Sarasota High
  • Mls Major Change Type: Price Decrease
  • Listing Service: Full Service
  • Senior Community: No
  • SW Subdiv Community Name: Cherokee Park
  • Unit Number: No
  • Street Number: 1774
  • Street Name: CHEROKEE
  • Street Suffix: DRIVE
  • State: FL
  • City: SARASOTA
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage Dimensions: 36x36
  • Garage: Yes
  • Parking Features: Electric Vehicle Charging Station(s), Garage Door Opener, Guest, Oversized
Taxes and HOA Information
  • Association Approval Required: No
  • Association Fee Requirement: Optional
  • Association: Yes
  • CDD: No
  • Tax Block: E
  • Tax Book Number: 2-156
  • Tax Legal Description: E 1/2 OF LOT 12 BLK E CHEROKEE PARK
  • Tax Lot: 12
  • Tax Year: 2024
Property
Lot Information
  • Additional Parcels: No
  • Lot Features: Corner Lot, Historic District, City Lot, Oversized Lot
  • Parcel Number: 2039010112
  • Total Acreage: 1/4 to less than 1/2
  • Water Access: No
  • Water Extras: No
  • Zoning: RSF1
  • Living Area: 3821
Property and Assessments
  • Year Built Numeric: 1982
  • Flood Zone Code: X
  • Flood Zone Date: 03-27-2024
  • Flood Zone Panel: 12115C0141G
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 18
  • Public Survey Section: 31
Utilities
  • Sewer: Public Sewer
  • Utilities: Cable Connected, Natural Gas Connected, Public, Sewer Connected, Sprinkler Well, Street Lights
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Cement Siding, HardiPlank Type
  • Exterior Features: French Doors, Irrigation System, Lighting, Outdoor Kitchen, Outdoor Shower, Rain Gutters
  • Fencing: Fenced, Wood
  • Foundation Details: Crawlspace
  • Levels: Two
  • Other Structures: Gazebo, Guest House, Outdoor Kitchen
  • Patio And Porch Features: Covered, Deck, Front Porch, Rear Porch, Wrap Around
  • Pool Features: Deck, Heated, Lighting, Outside Bath Access, Tile
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Shake
  • Spa: No
  • Vegetation: Mature Landscaping
  • Waterfront Feet Total: 0
Interior Features
  • Bedrooms Total: 4
  • Bathrooms Full: 3
  • Additional Rooms: Den/Library/Office, Inside Utility
  • Appliances: Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Ice Maker, Range Hood, Refrigerator, Tankless Water Heater, Washer
  • Cooling: Central Air, Mini-Split Unit(s), Zoned
  • Fireplace Features: Living Room, Wood Burning
  • Fireplace: Yes
  • Flooring: Ceramic Tile, Engineered Hardwood, Porcelain Tile, Slate, Hardwood
  • Heating: Electric
  • Interior Features: Built-in Features, Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
  • Laundry Features: Inside
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 11.0
  • Water View: No
  • Window Features: Storm Window(s), Window Treatments
  • Bathrooms Half: 2
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 1774 Cherokee Drive

DateEvent & SourcePriceAppreciation
Jan 29, 2026

Price Change

MFRMLS #A4669184

$3,795,000—
Oct 21, 2025

Listed (Active)

MFRMLS #A4669184

$3,975,000—
Aug 6, 2025

Withdrawn

MFRMLS #A4654813

$4,695,000—
Jun 6, 2025

Listed (Active)

MFRMLS #A4654813

$4,695,000—
Jun 3, 2025

Withdrawn

MFRMLS #TB8358611

$4,849,000—
Jun 2, 2025

Listed (Active)

MFRMLS #TB8358611

—
Jun 2, 2025

Withdrawn

MFRMLS #TB8358611

$4,849,000—
Mar 7, 2025

Listed (Active)

MFRMLS #TB8358611

$4,950,000—
Sep 12, 2013

Sold (Public Record)

Public Record #367468154

$875,000

+4.2% / yr

Sep 12, 2013

Sold

MFRMLS #A3979768

$875,000—
Jul 19, 2013

Pending

MFRMLS #A3979768

—
Jun 13, 2013

Listed (Active)

MFRMLS #A3979768

$987,000—
Jun 9, 2013

Expired

MFRMLS #A3975260

$1,019,000—
Mar 13, 2013

Listed (Active)

MFRMLS #A3975260

$1,199,000—
Sep 10, 2001

Sold (Public Record)

Public Record #78750326

$532,000—
DateEvent & SourcePrice
01/29/2026

Price Change

MFRMLS #A4669184

$3,795,000
10/21/2025

Listed (Active)

MFRMLS #A4669184

$3,975,000
08/06/2025

Withdrawn

MFRMLS #A4654813

$4,695,000
06/06/2025

Listed (Active)

MFRMLS #A4654813

$4,695,000
06/03/2025

Withdrawn

MFRMLS #TB8358611

$4,849,000
06/02/2025

Listed (Active)

MFRMLS #TB8358611

—
06/02/2025

Withdrawn

MFRMLS #TB8358611

$4,849,000
03/07/2025

Listed (Active)

MFRMLS #TB8358611

$4,950,000
09/12/2013

Sold (Public Record)

Public Record #367468154

$875,000

+4.2% / yr

09/12/2013

Sold

MFRMLS #A3979768

$875,000
07/19/2013

Pending

MFRMLS #A3979768

—
06/13/2013

Listed (Active)

MFRMLS #A3979768

$987,000
06/09/2013

Expired

MFRMLS #A3975260

$1,019,000
03/13/2013

Listed (Active)

MFRMLS #A3975260

$1,199,000
09/10/2001

Sold (Public Record)

Public Record #78750326

$532,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 1774 Cherokee Drive

Taxable ValueLand-Additions-Total-
Tax Record2025$17,437 ($1,453 / month)
Home Facts
Baths3.5Total Finished SqFt1,761 SqFtAbove Grade Finished SqFt1,761 SqFtStories2Lot Size20,000 SqFtStyleMulti-Family Dwelling (2-4)Year Built1982Year Renovated2017ZoningRSF1CountySARASOTAAPN2039-01-0112Fireplace TypeHas Fireplace

Schools near 1774 Cherokee Drive

This home is within Sarasota.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 6 to 8
Public - 9 to 12
Charter - K to 5
Rating
School
Distance
Southside Elementary School
PublicPK to 5

Brookside Middle School
Public6 to 8

Sarasota High School
Public9 to 12

Suncoast School For Innovative Studies
CharterK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

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1774 Cherokee Drive is a single family home for sale in Sarasota, FL 34239. This property was listed for sale on October 21, 2025 by MICHAEL SAUNDERS & COMPANY, it's currently listed at $3,795,000. It has been on the market for a total of 110 days and was last sold on September 12, 2013. This listing's school district is Sarasota. Nearby schools include Southside Elementary School, Brookside Middle School and Sarasota High School. 1774 Cherokee Drive is a 4-bed, 5-bath, 3,821 sqft single family home built in 1982.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of MICHAEL SAUNDERS & COMPANY, Lenore Treiman

The information is being provided in part by Southwest Florida Multiple Listing Service, Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2, and MarcoMls. Information deemed reliable but not guaranteed. Information is provided for consumers' personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2026 Southwest Florida Multiple Listing Service and MarcoMls. All Rights Reserved. The data relating to real estate for sale displayed on this website comes in part from the Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2 and MarcoMls. Properties listed with brokerage firms other than Compass are marked with the "BR House" logo. Detailed information about such properties includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties listed with brokerage firms participating in the Naples MLS BR Program, or contained in the database compilation of Naples MLS.