Single Family Residence at 156 SIESTA DR, SARASOTA
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67 photos

$1,649,000

156 SIESTA DR
SARASOTA, FL 34242
Listed by Curt Ware · KW COASTAL LIVING III
Bedrooms
5
Bathrooms
3
Living area
2,901 sqft
Year built
1977

About 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.

Highlights

Private pool

Property details

MLS
Stellar MLS
MLS #
MFRA4661717
Property type
Single Family Residence
Subdivision
SIESTA REV RESUB
Status
Active
Days on market
291
On market date
August 13, 2025
Stories
N/A
Total bathrooms
3
Garage spaces
2
Parking spaces
N/A
Lot size
0.25 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
SOUTHSIDE ELEMENTARY SCHOOL
1.65 mi away · Grades 0-5
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
681
Student:teacher ratio
14.8:1
District
SARASOTA
Middle
BROOKSIDE MIDDLE SCHOOL
1.98 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
760
Student:teacher ratio
15.8:1
District
SARASOTA
High
SARASOTA HIGH SCHOOL
2.48 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
2,508
Student:teacher ratio
20.1:1
District
SARASOTA

Walkability

Blended score for SARASOTA's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

50
Somewhat walkable
out of 100
EPA National Walkability Index
13.5 / 20 -- Above average walkable
Google Places amenity density
23 / 100
Restaurants & cafes0
Grocery stores0
Parks9
Schools1
Transit stops1
Pharmacies0

Market position

How this listing compares to current activity in SARASOTA, from live MLS data.

On the market 291 days -- 123 more days than SARASOTA's current average of 168 days.
For reference, the median list price across 4,720 active listings in SARASOTA right now is $365,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$10,080/mo
$329,800 down
$1,319,200 loan
Principal & interest$8,556
Property tax (est.)$1,374
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated May 31, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.