Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$1,649,000

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 2,901 Sq. Ft.
See This Home
Save This Home
See This Home
Save This Home
Situated in the sought-after Bay Isle community on Siesta Key, this exceptional three-level pool home combines the best of upscale coastal living with impressive rental performance. Designed to host gatherings of all sizes, it is perfectly suited as a primary residence, vacation escape, or income-producing property. In 2024, it brought in $132,419 in gross rental income, with 2025 projections at $120,681, showcasing its strong investment appeal. Just a short stroll to Shell Beach and minutes from Siesta Key Village and the world-renowned Siesta Key Beach, the home offers unmatched access to award-winning white sand, vibrant dining, and boutique shopping. A complete renovation in 2019 transformed the property with a new metal roof, hurricane-impact windows, patio and garage doors, upgraded AC systems, and an oversized resurfaced lap pool with all-new equipment, including a heat pump. Over 50 Areca palms frame the lush tropical landscaping, providing beauty and privacy while remaining easy to maintain. The outdoor living space rivals a private resort, featuring a sparkling pool, spacious patio, and tranquil surroundings ideal for lounging or entertaining. Inside, natural light fills the open floor plan, creating seamless flow to the outdoor areas and making it a true entertainer's haven. Impeccably maintained and move-in ready, this Bay Isle residence offers a rare opportunity to enjoy the island lifestyle while benefiting from consistent rental income.

Full Property Details for 156 Siesta Dr

General

  • Price: $1,649,000
  • Taxes: $19,016 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4661717
  • Updated: 11/18/2025
  • Added to Site: 156 day(s) ago

Rental Information

  • Min. Lease: 1 Week

Interior

  • Number of Rooms: 7
  • Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), Eating Space In Kitchen, Open Floorplan, Primary Bedroom Main Floor
  • Appliances: Dishwasher, Disposal, Microwave, Range, Refrigerator, Washer
  • Flooring: Luxury Vinyl, Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Inside

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Heated, In Ground

Exterior

  • Exterior Features: Lighting, Sliding Doors, Sprinkler Metered

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 34242 - Sarasota/Crescent Beach/Siesta Key
  • County: Sarasota
  • Development Name: 34242 - Sarasota/Crescent Beach/Siesta Key
  • Subdivision: SIESTA REV RESUB
  • Driving Directions: US 41 West on Siesta Dr to 156 Siesta Dr.
  • Direction Faces: North

Community

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

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

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

Structural Information

  • Exterior Const.: Wood Siding
  • Roof: Metal
  • Stories/Levels: Three Or More
  • Square Feet: 2,901
  • Sq. Ft. Source: Public Records
  • Year Built: 1977

Lot Features

  • Lot Size (Acres): 0.25
  • Lot Size (Sq. Ft.): 10,966
  • Lot Size: 10966
  • Street/Road Desc.: Asphalt

Financial Considerations

  • Tax Amount: $19,016
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 8 & PART OF LOT 7, RESUB OF BLK 29 OF REVISED PLAT OF SARASOTA BEING DESC AS COM AT NE CORNER OF LOT 1 RESUB OF BLK 29 OF REVISED PLAT OF SARASOTA TH N-64-16-07-W ALONG SLY R/W OF SIESTA
  • Flood Zone Info: AE
  • APN: 2019110035
  • Property ID: 2019110035
  • Block/Lot/Section: 29

Listed by Kw Coastal Living Iii

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 156 Siesta Dr —

  • Kw Coastal Living Iii

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 156 Siesta Dr

School District:Sarasota County School District
NameGradesDistance
Phillippi Shores Elementary School
4747 South Tamiami Trail, Sarasota, FL 34231
PK-52.2 mi
Brookside Middle School
3636 South Shade Avenue, Sarasota, FL 34239
6-82 mi
Sarasota High School
2155 Bahia Vista Street, Sarasota, FL 34239
9-122.4 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 156 Siesta Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/18/2025
Price Reduced
$1,649,000
-4.68%
MLS
8/13/2025
Listed
$1,730,000
8.46%
MLS
11/04/2021
Sold
$1,595,000
—
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 156 Siesta Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$19,016
-3%
$1,260,000
-7%
2023
$19,544
13%
$1,349,300
19%
2022
$17,350
62%
$1,136,400
62%
2021
$10,702
—
$699,500
19%
2021
$10,702
33%
$585,600
20%
2019
$8,071
-4%
$487,000
-3%
2018
$8,373
-3%
$504,500
-10%
2017
$8,643
5%
$562,600
5%
2016
$8,200
6%
$537,000
36%
2015
$7,757
13%
$395,791
10%
2014
$6,874
16%
$359,810
10%
2013
$5,909
—
$327,100
—
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 156 Siesta Dr

$
Down Payment
%
$
%

$
$

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

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Kw Coastal Living Iii

Similar Properties near 156 Siesta Dr

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

1647 Siesta Dr, Sarasota, FL 34239 - Photo 1
$1,740,000
Open House

1647 Siesta Dr  Sarasota, FL 34239

  • Single Family
  • Active
  • Updated 7 days ago
  • 5
    Beds
  • 3
    Total Baths
  • 3,023
    Sq. Ft.
Listed by Pham Realty Group Llc
5822 Title Row Dr, Bradenton, FL 34210 - Photo 1
$1,585,000

5822 Title Row Dr  Bradenton, FL 34210

  • Single Family
  • Active
  • 5
    Beds
  • 4
    Total Baths
  • 3,851
    Sq. Ft.
Listed by Compass Florida Llc
1775 Stapleton St, Sarasota, FL 34239 - Photo 1 Price Reduced
-$20,000 (-1.25%)
$1,575,000
Open House

1775 Stapleton St  Sarasota, FL 34239

  • Single Family
  • Active
  • Updated 3 days ago
  • 5
    Beds
  • 4
    Total Baths
  • 2,853
    Sq. Ft.
Listed by Premier Sotheby's International Realty
5718 Title Row Dr, Bradenton, FL 34210 - Photo 1
$1,550,000

5718 Title Row Dr  Bradenton, FL 34210

  • Single Family
  • Active
  • 5
    Beds
  • 4
    Total Baths
  • 3,654
    Sq. Ft.
Listed by Compass Florida Llc

Just Listed near 156 Siesta Dr

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

4960 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Just Listed
$650,000
Open House

4960 Gulf of Mexico Dr  #204  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 19 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,096
    Sq. Ft.
Listed by Marcela Terrell (941) 929-3010
3060 Grand Bay Blvd, Longboat Key, FL 34228 - Photo 1 Just Listed
$1,795,000

3060 Grand Bay Blvd  #195  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 4
    Total Baths
  • 2,250
    Sq. Ft.
Listed by Pettingell Professionals (941) 383-6411
795 Marbury Ln, Longboat Key, FL 34228 - Photo 1 Just Listed
$3,999,990

795 Marbury Ln  Longboat Key, FL 34228

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 3,355
    Sq. Ft.
Listed by Monica Verinder (941) 704-4040
350 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Just Listed
$1,149,000

350 Gulf of Mexico Dr  #234  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 19 minutes ago
  • 3
    Beds
  • 4
    Total Baths
  • 2,513
    Sq. Ft.
Listed by The Ackerman Group (941) 780-6045

Price Reduced near 156 Siesta Dr

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

1211 Gulf of Mexico Dr, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$110,000 (-11.01%)
$889,000

1211 Gulf of Mexico Dr  #704  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 6 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,585
    Sq. Ft.
Listed by Kepecz-Hays (941) 366-8070 and Leah George (941) 780-0597
4390 Exeter Dr, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$20,000 (-5.41%)
$350,000

4390 Exeter Dr  #305  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 6 days ago
  • 1
    Bed
  • 1
    Total Bath
  • 837
    Sq. Ft.
Listed by The VanDuren Group (941) 383-6411
3543 Mistletoe Ln, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$200,000 (-13.38%)
$1,295,000
Open House

3543 Mistletoe Ln  Longboat Key, FL 34228

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 4
    Total Baths
  • 3,239
    Sq. Ft.
Listed by Bruce Myer Group (941) 383-6411
1904 Harbourside Dr, Longboat Key, FL 34228 - Photo 1 Price Reduced
-$40,000 (-8.18%)
$449,000

1904 Harbourside Dr  #202  Longboat Key, FL 34228

  • Condo
  • Active
  • Updated 22 hours ago
  • 2
    Beds
  • 3
    Total Baths
  • 1,590
    Sq. Ft.
Listed by Bruce Myer Group (941) 383-6411

Recent Sales near 156 Siesta Dr

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

185 Faubel St, Sarasota, FL 34242 - Photo 1 Sold
$1,550,000

185 Faubel St  Sarasota, FL 34242

  • Single Family
  • Closed
  • 5
    Beds
  • 4
    Total Baths
  • 3,783
    Sq. Ft.
Listed by Compass Florida Llc
Sold by Preferred Shore Llc
110 Faubel St, Sarasota, FL 34242 - Photo 1 Sold
$1,650,000

110 Faubel St  Sarasota, FL 34242

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,340
    Sq. Ft.
Listed by Mairead Smialek and Samantha Kotlik
Sold by Bright Realty
4108 Roberts Point Rd, Sarasota, FL 34242 - Photo 1 Sold
$1,450,000

4108 Roberts Point Rd  Sarasota, FL 34242

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,511
    Sq. Ft.
Listed and Sold by Michael Saunders & Company
1800 Benjamin Franklin Dr, Sarasota, FL 34236 - Photo 1 Sold
$1,850,000

1800 Benjamin Franklin Dr  #A304  Sarasota, FL 34236

  • Condo
  • Closed
  • 2
    Beds
  • 3
    Total Baths
  • 2,230
    Sq. Ft.
Listed by Premier Sothebys Intl Realty
Sold by Premier Sotheby's International Realty

156 Siesta Drive, Sarasota, FL 34242 (MLS# A4661717) is a Single Family property with 5 bedrooms and 3 full bathrooms. 156 Siesta Drive is currently listed for $1,649,000 and was received on August 13, 2025. Want to learn more about 156 Siesta 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.

Tour this property