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$4,900,000

  • For Sale
  • Active
  • Single Family
  • 9 Beds
  • 11 Total Baths
  • 4,437 Sq. Ft.
  • Updated 12 days ago
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Nightly rentals, a unicorn. This 7-unit investment property is unique in that it operates more similar to hotel than a single family vacation rental. It has years of returning guests and it's one of very few elevated properties allowing the former mentioned, nightly rentals. 2-studios, 2-1 bedrooms, 2-2 bedrooms, and a penthouse suite with wrap around balcony. Your guests will enjoy a great pool area, sizable covered space with a grill, on site laundry, and a roof top deck. It's 1 block to both the Village and beach, guests walk everywhere. Park your car in one of the 7 newly pavered spaces and don't start it again until the vacation is over. Now for you the owner, a private office/guest check in, 2 storage areas for linens housewares etc, and a commercial laundry for turnovers. These types never trade, don't let another 20 years pass before this sells again.

Full Property Details for 5322 Calle De La Siesta

General

  • Price: $4,900,000
  • Taxes: $22,056 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4682172
  • Updated: 2/12/2026
  • Added to Site: 12 day(s) ago

Rental Information

  • Min. Lease: 1-7 Days

Interior

  • Interior Features: Built-in Features, Ceiling Fan(s), Thermostat

Rooms

Bathrooms

  • Total Bathrooms: 11

Bedrooms

  • Total Bedrooms: 9

Other Rooms

  • Laundry: Common Area, Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground
  • Spa: Yes

Exterior

  • Exterior Features: Balcony, Fenced, Private Entrance, Storage

Location

  • Area: 34242 - Sarasota/Crescent Beach/Siesta Key
  • County: Sarasota
  • Development Name: 34242 - Sarasota/Crescent Beach/Siesta Key
  • Subdivision: SARASOTA BEACH
  • Driving Directions: Turn off Beach Rd to Calle De la Siesta

Community

  • Community Name: 34242 - Sarasota/Crescent Beach/Siesta Key

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV Available, Cable Connected, Electricity Connected, Public

Structural Information

  • # Buildings: 1
  • Exterior Const.: Block
  • Roof: Metal
  • Stories/Levels: Two
  • Square Feet: 4,437
  • Sq. Ft. Source: Public Records
  • Year Built: 1999

Lot Features

  • Lot Size (Acres): 0.13
  • Lot Size (Sq. Ft.): 5,514
  • Lot Size: 5514
  • Street/Road Desc.: Asphalt

Water Features

  • Water Access: Yes
  • Water Access Desc: Gulf/Ocean

Financial Considerations

  • Tax Amount: $22,056
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: BEG AT NELY COR OF LOT 16 BLK 17 TH S-4-35-W ALG E LINE OF SAID LOT 16 64.98 FT TO SE COR OF LOT 16 TH S-9-09-W ALG E LINE OF LO
  • Flood Zone Info: AE
  • APN: 82120051
  • Property ID: 82120051
  • Block/Lot/Section: 17

Listed by Compass Florida Llc

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Listing agent

— 5322 Calle De La Siesta —

  • Compass Florida Llc

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 5322 Calle De La Siesta

School District:Sarasota County School District
NameGradesDistance
Phillippi Shores Elementary School
4747 South Tamiami Trail, Sarasota, FL 34231
PK-52.3 mi
Brookside Middle School
3636 South Shade Avenue, Sarasota, FL 34239
6-83 mi
Sarasota High School
2155 Bahia Vista Street, Sarasota, FL 34239
9-124.2 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5322 Calle De La Siesta Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/12/2026
Listed
$4,900,000
512.5%
MLS
7/13/2010
Sold
$800,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5322 Calle De La Siesta

Year
Property Taxes
Change
Tax Assessment
Change
2025
$20,243
-13%
$1,964,600
-7%
2024
$23,369
12%
$2,113,900
14%
2023
$20,877
38%
$1,852,600
77%
2021
$15,094
-18%
$1,047,300
-33%
2022
$18,447
22%
$1,561,400
54%
2021
$15,094
8%
$1,016,700
6%
2019
$13,964
-9%
$961,800
-7%
2018
$15,408
11%
$1,032,980
—
2017
$13,820
11%
$1,037,200
12%
2016
$12,454
5%
$926,100
19%
2015
$11,879
11%
$776,094
10%
2014
$10,663
11%
$705,540
10%
2013
$9,578
—
$641,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 5322 Calle De La Siesta

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Compass Florida Llc

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5322 Calle De La Siesta, Sarasota, FL 34242 (MLS# A4682172) is a Single Family property with 9 bedrooms and 0 full bathrooms. 5322 Calle De La Siesta is currently listed for $4,900,000 and was received on February 12, 2026. Want to learn more about 5322 Calle De La Siesta? 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.

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