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$2,099,000
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Property Description
New Price ~ Siesta Key ~ Siesta Isles Neighborhood ~ 123' Water-Frontage ~ Close To Siesta Key Beach ~ Home Updated Throughout (Inside - Outside) ~ Oversized Lot: 12,000+ Square Feet ~ Pool ~ Two Boat Docks With Lifts ~ New Seawall ~ Pool / Yard / Docks All South Facing ~ Prime Location With Privacy (Dead End Street)! "SOLD" Turn Key Furnished (seller will consider leaving two boats on two lifts & one car) ~ Room To Expand Bedrooms / Other ~ Full Updated Home Inspection With Insurance Required Wind Mitigation / Four Point On Request ~ Owner Will Contribute To New Roof If Required ~ Begin Your Siesta Key Living Adventure! By The Way "OWNER FINANCING AVAILABLE". What A Great Overall "Beach Style Living Opportunity" On Beautiful Siesta Key! The Property Photos / Drone Photo's Say It All ~ Ready To Show!
Full Property Details
Full Property Details for 5569 Contento Dr
General
- Price: $2,099,000
- HOA FEE: $17/month
- HOA FEE FREQ.: Annually
- Taxes: $6,882 (2024)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: A4670108
- Updated: 12/3/2025
- Added to Site: 79 day(s) ago
Rental Information
- Min. Lease: 1 Month
Interior
- Number of Rooms: 3
- Interior Features: Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Thermostat, Wet Bar, Window Treatments
- Appliances: Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Other, Range Hood, Refrigerator, Washer, Wine Refrigerator
- Furnishings: Turnkey
- Flooring: Brick/Stone, Carpet, Ceramic Tile, Engineered Hardwood, Other, Porcelain Tile, Tile
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 2
Other Rooms
- Laundry: Electric Dryer Hookup, In Garage, Laundry Room, Other, Washer Hookup
Additional Information
- Shared Amenities: Security
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, Heated, In Ground, Lighting, Other
- Spa: Yes
- Spa Description: Above Ground, Heated, Other
- Security/Safety: Security System, Security System Owned, Smoke Detector(s)
Exterior
- Exterior Features: Garden, Hurricane Shutters, Irrigation System, Lighting, Other, Outdoor Kitchen, Outdoor Shower, Private Mailbox, Rain Gutters, Sliding Doors, Storage
- Deck/Patio: Covered, Deck, Enclosed, Other, Patio, Porch, Screened
- Porch/Patio/Deck: Covered, Deck, Enclosed, Other, Patio, Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Boat, Deeded, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Golf Cart Parking, Ground Level, Guest, On Street, Other, Oversized, RV Parking, Workshop in Garage
Location
- Area: 34242 - Sarasota/Crescent Beach/Siesta Key
- County: Sarasota
- Development Name: 34242 - Sarasota/Crescent Beach/Siesta Key
- Subdivision: SIESTA ISLES
- Driving Directions: Sarasota, FL ~ Siesta Key ~ Contento Drive ~ #5569
- Direction Faces: East
School Information
- Elementary School: Phillippi Shores Elementary
- Middle School: Brookside Middle
- High School: Sarasota High
Community
- Community Name: 34242 - Sarasota/Crescent Beach/Siesta Key
- Community Features: Canal Front, Deed Restrictions, Golf Carts OK
- Optional Amenities: Security
- Association: Yes
- Assoc. Name: FPMS
- Assoc. Fees Include: Other
- Number of Pets: 2
- Pet Restrictions: Refer to "Sarasota County Zoning" Requirements.
- Management Type: Full Time
- Mgmt. Company: Full Time
Heating & Cooling
- Cooling Type: Central Air, Other, Zoned
- Heating Type: Central, Electric, Heat Pump, Other, Zoned
Utilities
- Sewer: Public Sewer
- Water District: SIESTA ISLES CANAL SYSTEM
- Water: Public
- Utility Description: Cable Connected, Electricity Connected, Fiber Optics, Fire Hydrant, Other, Private, Public, Sewer Connected, Sprinkler Meter, Street Lights, Water Connected
Structural Information
- Architectural Info: Florida, Other, Patio, Ranch, Traditional
- Architectural Style: Florida, Other, Patio, Ranch, Traditional
- Exterior Const.: Block, Concrete, Other, Stucco
- Roof: Membrane, Other, Tile
- Common Walls: End Unit
- Windows: Aluminum Frames, Blinds, Double Pane Windows, ENERGY STAR Qualified Windows, Insulated Windows, Storm Window(s), Thermal Windows, Tinted Windows, Window Treatments
- Stories/Levels: One
- Square Feet: 1,772
- Sq. Ft. Source: Public Records
- Year Built: 1969
Additional Structures
- Other Structures: Gazebo, Other, Outdoor Kitchen, Shed(s), Storage, Workshop
Lot Features
- Property View: Pool, Water
- Lot Size (Acres): 0.28
- Lot Size (Sq. Ft.): 12,100
- Lot Size: 12100
- Lot Dimensions: 120.78 x 122.43
- Frontage: Street Dead-End, Street Paved
- Street/Road Desc.: Paved, Asphalt, Concrete, Other
- Fencing (Description): Other
Water Features
- Water Front: Yes
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Canal - Saltwater, Gulf/Ocean, Gulf/Ocean to Bay, Intracoastal Waterway
- Water Extras: Yes
- Water Front Name: SIESTA ISLES CANAL SYSTEM
- Water Front Desc.: Canal Front, Saltwater Canal
Financial Considerations
- Association Fee: $200
- Assoc Fee Freq.: Annually
- Assoc Fee Desc.: Optional
- Tax Amount: $6,882.56
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: LOT 264 SIESTA ISLES UNIT 8
- Flood Zone Info: AE
- APN: 82160016
- Property ID: 82160016
Listed by Re/Max Alliance Group
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Schools
Schools serving 5569 Contento Dr
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Phillippi Shores Elementary School 4747 South Tamiami Trail, Sarasota, FL 34231 | PK-5 | 1.8 mi |
Brookside Middle School 3636 South Shade Avenue, Sarasota, FL 34239 | 6-8 | 2.6 mi |
Sarasota High School 2155 Bahia Vista Street, Sarasota, FL 34239 | 9-12 | 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 5569 Contento Dr
Date
Details
Price
Change
Source
12/03/2025
Price Reduced
$2,099,000
-4.55%
MLS
11/09/2025
Price Reduced
$2,199,000
-10.57%
MLS
10/29/2025
Listed
$2,459,000
391.8%
MLS
11/06/2009
Sold
$500,000
—
Public Record
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
Tax History for 5569 Contento Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$6,883
3%
$575,383
3%
2023
$6,660
3%
$558,624
6%
2021
$6,481
—
$526,556
-3%
2022
$6,486
—
$542,353
4%
2021
$6,481
3%
$519,286
2%
2019
$6,310
2%
$507,611
2%
2018
$6,180
—
$498,146
2%
2017
$6,154
—
$487,900
2%
2016
$6,148
2%
$477,865
4%
2015
$6,029
—
$457,930
1%
2014
$6,007
—
$454,296
2%
2013
$6,006
—
$447,582
—
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
Estimate the Cost for 5569 Contento Dr
5569 Contento Drive, Sarasota, FL 34242 (MLS# A4670108) is a Single Family property with 2 bedrooms and 2 full bathrooms. 5569 Contento Drive is currently listed for $2,099,000 and was received on October 29, 2025. Want to learn more about 5569 Contento 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.

