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1655 South Dr, Sarasota, FL, 34239

5beds
9baths
6,355sqft
$5,900,000
$928price/sqft
$45,599/moest. monthly cost
$1,823,960/yrincome needed

About This Home

One or more photo(s) has been virtually staged. In Sarasota's desired West of Trail enclave of Cherokee Park, 1655 South Drive, masterfully designed three-story estate where thoughtful architecture meets effortless luxury. Positioned on a homesite that is not in a Special Flood Hazard Area and enhanced with full home hurricane-impact glass and a whole-home generator, this residence offers the rare combination of refinement and peace of mind. Spanning 6,355+ square feet, the home features five bedrooms, five full baths and four half baths, with a layout tailored for grand entertaining and everyday ease. A rear three-car garage, accessed discreetly from South Lodge Drive, preserves the home's striking street presence. Inside, the main level unfolds into a wide-open living experience with a great room with wet bar, formal dining, and a showpiece chef's kitchen outfitted with Wolf dual-oven six-burner range, dual side by side 36” Sub-Zero Over-and-Under Refrigerator/Freezers, a Wolf microwave drawer, a Wolf warming drawer, and built-in Miele espresso machine. The first-floor primary suite is a private retreat, complete with an in-home gym, a spa-inspired bath and dual custom-fitted closets. A beautifully appointed guest suite (fifth bedroom) with en-suite bath also anchors the main level. Access to the upper floors is seamless via a dramatic staircase with custom wrought-iron railings or the private elevator. Upstairs, three additional en-suite bedrooms include custom walk-in closets, one thoughtfully designed with built-in bunk beds, plus a bonus club room with built-in desks and additional laundry for added convenience. Outdoors, the property transforms into a walled and gated resort-style oasis featuring a gas-heated saltwater pool with sun shelf and spa, and an artificial turf lounge/play area. A screened entertainment lounge with a convenient half pool bath connects to a full outdoor kitchen with sink, TV and gas grill, all complemented by a pergola and a mosquito misting system, ideal for Sarasota's seasons. Above the garage, a spectacular casita-style retreat, accessible by the home’s second private interior elevator or exterior spiral staircase, elevates entertaining to an entirely new level with a 2,000-bottle refrigerated wine room, a fully equipped wet bar, mini- fridge, clear ice maker, and dishwasher. Go onto the covered terrace with a gas fireplace, then unwind on the third floor in the private, pool-like infinity-edge spa, an experience that feels equal parts boutique resort and private club. Ideally in walking distance to A-rated Southside Elementary School, Southside Village, Sarasota Memorial Hospital, downtown Sarasota and short drive to the world-famous sands of Siesta Key Beach, this is a rare opportunity to own a bespoke residence in one of Sarasota's treasured neighborhoods.

Getting Around

36
WalkingCar-Dependent
29
TransitSome Transit
54
BikeBikeable

Schools

10/10
6/10
Brookside Middle SchoolGrades 6-80.9 mi
5/10
Sarasota High SchoolGrades 9-121.4 mi

Construction

Condition

  • Property condition: Completed
  • Year built: 2011

Materials

  • Foundation: Slab,Stem Wall
  • Roof: Membrane,Metal,Tile
  • Construction materials: Block,Stone,Stucco

Type & Style

  • Home type: SingleFamily
  • Architectural style: Custom,Other
  • Property subType: Single Family Residence

Interior

Appliances

  • Appliances included: Bar Fridge,Oven,Cooktop,Dishwasher,Disposal,Dryer,Gas Water Heater,Microwave,Range,Range Hood,Refrigerator,Tankless Water Heater,Washer
  • Laundry features: Inside,Laundry Room,Other,Upper Level

Bathroom5

  • Features: Stone Counters
  • Level: Second
  • Area: 352
  • Dimensions: 22x16

Bedroom2

  • Features: Built-In Shower Bench,En Suite Bathroom,Exhaust Fan,Shower No Tub,Single Vanity,Stone Counters,Walk-In Closet(s)
  • Level: First
  • Area: 182
  • Dimensions: 14x13

Bedroom3

  • Features: En Suite Bathroom,Exhaust Fan,Single Vanity,Tub With Shower,Walk-In Closet(s)
  • Level: Second
  • Area: 195
  • Dimensions: 15x13

Bedroom4

  • Features: En Suite Bathroom,Exhaust Fan,Shower No Tub,Stone Counters,Walk-In Closet(s)
  • Level: Second
  • Area: 182
  • Dimensions: 14x13

Bedrooms & Bathrooms

  • Bedrooms: 5
  • Bathrooms: 9
  • Full bathrooms: 5
  • 1/2 bathrooms: 4

Bonus Room

  • Features: Bar,Built-In Shelving,Built-in Features,Other,Water Closet/Priv Toilet,No Closet
  • Level: Second
  • Area: 462
  • Dimensions: 22x21

Den

  • Features: Bar,Built-In Shelving,Built-in Features,En Suite Bathroom,Granite Counters,Sink - Pedestal,Wet Bar
  • Level: Second
  • Area: 682
  • Dimensions: 22x31

Dinette

  • Level: First
  • Area: 140
  • Dimensions: 14x10

Dining Room

  • Features: Bar,Built-In Shelving,Other
  • Level: First
  • Area: 228
  • Dimensions: 19x12

Family Room

  • Features: Breakfast Bar,Wet Bar
  • Level: First
  • Area: 286
  • Dimensions: 22x13

Features

  • Built-in Features,Cathedral Ceiling(s),Ceiling Fan(s),Crown Molding,Dry Bar,Elevator,High Ceilings,Open Floorplan,Primary Bedroom Main Floor,Solid Surface Counters,Solid Wood Cabinets,Split Bedroom,Stone Counters,Thermostat,Tray Ceiling(s),Vaulted Ceiling(s),Walk-In Closet(s),Wet Bar,In-Law Floorplan
  • Door features: French Doors,Outdoor Grill,Outdoor Kitchen,Outdoor Shower,Sliding Doors
  • Window features: Blinds,Window Treatments,Hurricane Shutters/Windows
  • Flooring: Concrete,Engineered Hardwood,Porcelain Tile,Travertine,Hardwood
  • Fireplace features: Gas,Living Room,Outside
  • Fireplace: Yes

Gym

  • Level: First
  • Area: 100
  • Dimensions: 10x10

Heating & Cooling

  • Heating features: Central,Electric,Natural Gas,Zoned
  • Cooling features: Central Air,Zoned

Interior Area

  • Total structure area: 8,306
  • Total interior livable area: 6,355 sqft

Kitchen

  • Features: Bar,Breakfast Bar,Built-In Shelving,Pantry,Dual Sinks,Kitchen Island,Other,Stone Counters,Wet Bar
  • Level: First
  • Area: 288
  • Dimensions: 18x16

Living Room

  • Level: First
  • Area: 360
  • Dimensions: 20x18

Primary Bedroom

  • Features: Stone Counters,Tub with Separate Shower Stall,Water Closet/Priv Toilet,Walk-In Closet(s)
  • Level: First
  • Area: 294
  • Dimensions: 21x14

Property

Details

  • Parcel number: 2039020017
  • Zoning: RSF1
  • Special condition: None

Features

  • Levels: Three Or More
  • Stories: 3
  • Private pool: Yes
  • Pool features: Deck,Gunite,Heated,In Ground,Lighting,Other,Outside Bath Access
  • Patio & porch: Covered,Deck,Other,Patio,Porch,Rear Porch,Screened,Side Porch
  • Exterior features: Balcony,Irrigation System,Lighting,Misting System,Other,Outdoor Grill,Outdoor Kitchen,Outdoor Shower,Rain Gutters,Sidewalk
  • Has spa: Yes
  • Spa features: Above Ground,Heated,Other
  • Fencing: Electric,Fenced,Masonry,Stone
  • Has view: Yes
  • View description: Garden,Pool,Trees/Woods
  • Residential vegetation: Mature Landscaping,Oak Trees,Trees/Landscaped

Lot

  • Lot size: 0.34 Acres
  • Features: FloodZone,City Lot,Near Public Transit,Sidewalk,Street Dead-End,Above Flood Plain

Parking

  • Total spaces: 3
  • Parking features: Garage Door Opener,Garage Faces Rear,Garage Faces Side,Ground Level
  • Has garage: Yes
  • Attached garage spaces: 3
  • Covered spaces: 3

Climate Risk is Financial Risk

Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.

Biggest Threats for This Home

  • Hurricane
    HurricaneRelatively High
  • Lightning
    LightningModerate
  • Tsunami
    TsunamiInsufficient Data

How This Home’s Risks Compare

Hurricane
Lightning
Tsunami

FEMA Declared Disasters in Sarasota County and Florida

Coastal Storm
Flood
Hurricane
Severe Storm
Straight Line Winds
Tornado
Tropical Depression
Tropical Storm

Understanding the Costs

Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.

Estimated Costs Today

MonthlyAnnual
Mortgage $29,833$357,996
Home Insurance *$7,762$93,144
Property Taxes $7,365$88,380
Electricity $639$7,674
Total$45,599$547,188
*Does not include cost of any FAIR Plan premiums

Income You'd Need if You Spent...

35% on housing$1,563,394/yr
40% on housing$1,367,970/yr
45% on housing$1,215,973/yr

Florida FAIR Plan Programs

Citizens Property Insurance Corporation [Florida]

Covered
WildfireWildfire
HailHail
WindWind
Visit Website →
Current Policies
Residential: 1,321,953Commercial: 13,564
Total Premiums$4.60B
Total Exposure$385.82B

How Costs Could Change Over Time

Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.

Insurance Growth Rate5-year average: 15.0%
15.0%
0%30.0%
Electricity Growth Rate10-year average: 2.2%
2.2%
0%15.0%
Property Taxes Growth Rate2-year average: 6.6%
6.6%
0%15.0%
Income Spent on Housing
30%
30%45%

Comparing Against the Market

Price Per Sq Ft

$928This listing

vs Other Active Listings

Avg $/sqft

ZIP 34239$633
Sarasota County$345

vs Homes Sold Last Month

Median $/sqft

ZIP 34239$363
Sarasota County$245

Current Market Trends

Median Price Per Square Foot

The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.

Historicals for This Listing

Zestimate History ($/sqft)

Price History

DateEventPrice
2026-05-05Listed for sale$5,900,000
2024-07-11Listing removed$5,695,000
2024-03-18Price change$5,695,000
2024-02-29Price change$5,985,000
2024-02-26Price change$5,695,000
2023-11-16Listed for sale$5,985,000
2023-10-14Listing removed--
2023-10-06Listed for sale$6,249,000
2013-11-27Sold$2,100,000
2013-08-06Listing removed$2,250,000
2013-04-17Listed for sale$2,250,000
2009-03-30Sold$545,000
2004-01-30Sold$600,000

For Sale by Agent

AgentKaty McBrayer
BrokeragePREMIER SOTHEBY'S INTERNATIONAL REALTY

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