Active
$2,300,000
Est. $15,308/mo

1585 South Dr, Sarasota, FL, 34239

$832/sqft·Cherokee Park

3 bd4 ba2,764 sqft2 car garageSingle Family
Listed by MICHAEL SAUNDERS & COMPANY· Last updated · MLS# A4704763

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Est. monthly payment
$15,308/mo
Down payment (20%)
$460,000
Property taxes
$2,163/mo
Rate assumed
6.8% · 30 yr
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At a glance

Single family
Built 1964
2 car garage
Driveway
0.38 acres
Lot size
2,764 sqft
Living area

About this home

Ceiling Fans(s)Living Room/Dining Room ComboPrimary Bedroom Main FloorStone CountersWalk-in Closet(s)Window TreatmentsBar FridgeBuilt-in Oven

1585 South Dr is a 1964-built home in Cherokee Park, Sarasota. Inside you'll find 3 bedrooms, 4 bathrooms, and 2,764 square feet of living space. Listed at $2,300,000 (about $832/sqft), 1 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable.

From the listing

Set on a beautiful corner lot in the highly sought-after Cherokee Park neighborhood, this charming two-story residence offers three bedrooms, three-and-a-half baths, and a rare opportunity to create a home tailored to your vision. Surrounded by a lush, expansive yard with ample room for a pool, the property offers exceptional flexibility for its next owner. Enjoy the home's timeless character as it is, or take advantage of the opportunity to create your dream home in one of Sarasota's most established neighborhoods. Inside, a light-filled, open floor plan is complemented by beautiful wood floors and an inviting sense of warmth throughout. The main level features a comfortable guest bedroom with an adjacent full bath, as well as a spacious en-suite primary bedroom, offering the ease and convenience of first-floor living. Upstairs, a private en-suite retreat is filled with character, featuring charming dormer windows, built-in window seats, and extensive storage. Adding to the property's remarkable potential is a recently approved variance along the side of the lot, providing an additional 10 feet of buildable envelope and expanding the possibilities for a future renovation, addition, or new residence. Ideally situated West of the Trail, this exceptional property places you close to top-rated schools, Sarasota Memorial Hospital, the shops and dining of Southside Village, the world-renowned beaches of Siesta Key, and vibrant downtown Sarasota. With its coveted location, generous homesite, and unique development potential, this Cherokee Park property presents an extraordinary opportunity to create something truly special.

The essentials

Built
1964
Price / sqft
$832
On market
7 days
Annual tax
$25,958
Flood zone
X · Low risk
Lot
16,433 sqft
Type
Single Family Residence

Location

1585 South Dr
Sarasota, FL, 34239·34239 - Sarasota/Pinecraft
Type
Single Family Residence
Year Built
1964
Lot
16,433 sqft
Cooling
Central Air
Heating
Central
Parking
Driveway, Garage Door Opener
Days on Market
7
Ceiling Fans(s)
Living Room/Dining Room Combo
Primary Bedroom Main Floor
Stone Counters
Walk-in Closet(s)
Window Treatments
Bar Fridge
Built-in Oven
Dishwasher
Disposal
Dryer
Microwave
Tankless Water Heater
Washer

Elementary

Southside Elementary

Middle

Sarasota Middle

High

Sarasota High

Districts can re-zone, so verify directly with the district before relying on these.

Flood Zone X

Annual Tax (2025)

$25,958

Parcel #

2039030009

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision

Cherokee Park

County

Sarasota

MLS Area

34239 - Sarasota/Pinecraft

Lot Size

16,433 sqft

Corner LotCity LimitsSidewalkPaved
Date
Event
Price
9/4/2026
Listed for sale
Source: Stellar MLS #A4704763
$2,300,000
$832/sqft
Est. monthly payment$15,309/mo
Principal & interest$11,995
Property taxes$2,163
Insurance$1,150
Down payment20% · $460,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Offer Insights

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List price: $2,300,000
$2.21M – $2.30M
96.1% – 100% of listTops out right at the list price
80% of listList price
59 of the last 117 home closings in 34239 landed at this number or higher (50%). The median one sat 63 days before it went under contract, and this one is on day 7.

Sample: 117 closed home sales in 34239 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

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