3 Homes 1 large Lot - 3476 WINTON AVE, SARASOTA
Your New Sarasota, FL Compound - 3476 WINTON AVE, SARASOTA
Cottage 1 of 3 - 3476 WINTON AVE, SARASOTA
Cottage 2 of 3 - 3476 WINTON AVE, SARASOTA
Cottage 3 of 3 - 3476 WINTON AVE, SARASOTA
3 Homes 1 large Lot - 3476 WINTON AVE, SARASOTA
Cottage 2 - 3476 WINTON AVE, SARASOTA
3 Homes 1 large Lot - 3476 WINTON AVE, SARASOTA
Shared Pool Area - 3476 WINTON AVE, SARASOTA
Shared Pool Area - 3476 WINTON AVE, SARASOTA
Cottage 1 - 3476 WINTON AVE, SARASOTA
Cottage 1 Living Room - 3476 WINTON AVE, SARASOTA
Cottage 1 Living Room - 3476 WINTON AVE, SARASOTA
Cottage 1 Living Room - 3476 WINTON AVE, SARASOTA
Cottage 1 Living Room - 3476 WINTON AVE, SARASOTA
Cottage 1 Dining room - 3476 WINTON AVE, SARASOTA
Cottage 1 Dining room - 3476 WINTON AVE, SARASOTA
Cottage 1 Dining room/ living room - 3476 WINTON AVE, SARASOTA
Cottage 1 Living Room - 3476 WINTON AVE, SARASOTA
Cottage 1 Dining Room - 3476 WINTON AVE, SARASOTA
Cottage 1 Living Room - 3476 WINTON AVE, SARASOTA
Cottage 1 kitchen - 3476 WINTON AVE, SARASOTA
Cottage 1 kitchen - 3476 WINTON AVE, SARASOTA
Cottage 1 kitchen - 3476 WINTON AVE, SARASOTA
Cottage 1 kitchen - 3476 WINTON AVE, SARASOTA
Cottage 1 Owner Bed - 3476 WINTON AVE, SARASOTA
Cottage 1 Owner Bed - 3476 WINTON AVE, SARASOTA
Cottage 1 Owner Bed - 3476 WINTON AVE, SARASOTA
Cottage 1 Owner Bed - 3476 WINTON AVE, SARASOTA
Cottage 1 Owner bath - 3476 WINTON AVE, SARASOTA
Cottage 3 Guest Bed 2 - 3476 WINTON AVE, SARASOTA
Cottage 1 Guest Bed 2 - 3476 WINTON AVE, SARASOTA
Cottage 1 Guest bath 2 - 3476 WINTON AVE, SARASOTA
Cottage 1 Guest Bed 3 - 3476 WINTON AVE, SARASOTA
Cottage 1 Guest Bed 3 - 3476 WINTON AVE, SARASOTA
Cottage 1 Guest Bed 3 - 3476 WINTON AVE, SARASOTA
Cottage 1 Guest Bed 3 - 3476 WINTON AVE, SARASOTA
Extra lot to build 4th home - 3476 WINTON AVE, SARASOTA
Extra lot to build 4th home - 3476 WINTON AVE, SARASOTA
Extra lot to build 4th home - 3476 WINTON AVE, SARASOTA
Extra lot to build 4th home - 3476 WINTON AVE, SARASOTA
Extra lot to build 4th home - 3476 WINTON AVE, SARASOTA
Close to Sarasota Bay - 3476 WINTON AVE, SARASOTA
Close to Ringling museum - 3476 WINTON AVE, SARASOTA
Close to Airport - 3476 WINTON AVE, SARASOTA
Extra lot to build 4th home - 3476 WINTON AVE, SARASOTA
Cottage 1 - 3476 WINTON AVE, SARASOTA
Cottage 2 + 3 - 3476 WINTON AVE, SARASOTA
Cottage 2 - 3476 WINTON AVE, SARASOTA
Cottage 3 - 3476 WINTON AVE, SARASOTA
3 homes 1 lot + Pool - 3476 WINTON AVE, SARASOTA
51 photos

$1,400,000

3476 WINTON AVE
SARASOTA, FL 34234
Listed by FLORIDA LIFE TEAM LLC
Bedrooms
9
Bathrooms
N/A
Living area
3,228 sqft
Year built
1989

About this home

A rare, one of a kind Sarasota investment opportunity offering incredible flexibility, privacy, and income potential! Come invest in one of the most highly desirable areas in Florida. 1 parcel features 3 detached single family homes, plus additional space with potential to build a fourth home. Each residence offers 3 bedrooms and 2 bathrooms with updated interiors, charming individual designs, and lush tropical landscaping throughout. At the heart of the property is an inviting shared pool area with cabana spaces, creating a private tropical setting to relax, entertain, and enjoy the Florida lifestyle. The property is extremely private, with lush surroundings and plenty of room to expand and create an even more impressive compound. Currently income producing, the property includes active vacation rentals, while one cottage is utilized as student housing with bedrooms rented individually. Its proximity to Ringling College of Art and Design and New College of Florida adds another layer of rental potential. Continue the existing strategy or reimagine the property as a multi generational retreat, artist compound, private residential compound, or a unique setup for friends who want to live close while maintaining their own private residences. Tucked away on a private dead end street with no HOA and outside of a designated flood zone, the location is exceptional. Minutes from Downtown Sarasota, The Ringling Museum, Sarasota Bradenton International Airport, Ringling College, New College, dining, shopping, and Sarasota Bay, which is even within walking distance. With 3 existing homes, a pool and cabana area, multiple income possibilities, exceptional privacy, and room for future expansion, opportunities like this are incredibly hard to find in Sarasota. Keep everything operating as is and generate income, or bring your vision and unlock even more potential. Book your private showing today before your next investment opportunity in Sarasota,Florida is gone!

Highlights

Private pool

Property details

MLS #
MFRA4705532
Property type
Triplex
Subdivision
INDIAN BEACH
Status
Active
Days on market
1
On market date
September 10, 2026
Stories
N/A
Total bathrooms
N/A
Garage spaces
N/A
Parking spaces
N/A
Lot size
0.63 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 (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
BAY HAVEN SCHOOL OF BASICS PLUS
0.38 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
587
Student:teacher ratio
14.7:1
District
SARASOTA
Middle
BOOKER MIDDLE SCHOOL
1.49 mi away · Grades 6-8
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
911
Student:teacher ratio
14.2:1
District
SARASOTA
High
BOOKER HIGH SCHOOL
0.45 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
1,296
Student:teacher ratio
18.3:1
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).

84
Highly walkable
out of 100
EPA National Walkability Index
14.7 / 20 -- Above average walkable
Google Places amenity density
100 / 100
Restaurants & cafes20
Grocery stores5
Parks12
Schools9
Transit stops20
Pharmacies3

Market position

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

On the market 1 days -- 176 fewer days than SARASOTA's current average of 177 days.
For reference, the median list price across 4,319 active listings in SARASOTA right now is $349,000.

Mortgage calculator

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

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Est. monthly payment
$8,581/mo
$280,000 down
$1,120,000 loan
Principal & interest$7,264
Property tax (est.)$1,167
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 19 days ago.

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.