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$515,000

  • For Sale
  • Active
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1,647 Sq. Ft.

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Open House: 1:00 PM - 5:00 PM

Sunday 2/22 1:00 PM - 5:00 PM

5099 Flag Street,Sarasota, FL 34232

5099 Flag StreetSarasotaFL34232

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A beautiful, rare corner-unit, single-story residence in the gated Enclave at Forest Lakes, ideally located in the heart of Sarasota. This meticulously maintained home offers privacy, natural light, and an open layout designed for effortless living, all just minutes from Siesta Key Beach, downtown Sarasota, major highways, shopping, dining, and everyday conveniences. Featuring 2 bedrooms, a dedicated office/den with double French doors, and 2 bathrooms, the home showcases over $60,000 in builder upgrades. Interior highlights include 9-foot ceilings, 8-foot paneled doors, rich hardwood flooring throughout, and stylish tile in both bathrooms. The chef's kitchen is a standout with light cabinetry, pull-out storage features, quartz countertops, a large island with a breakfast bar, stainless steel appliances, and a marble backsplash. The primary suite serves as a private retreat with a tray ceiling and a spa-like bath offering a walk-in shower, dual sinks, quartz counters, and ample storage. The great room opens to a full-width covered and screened lanai with remote-controlled fans and ceiling speakers, creating an ideal indoor-outdoor living space. Residents enjoy maintenance-free living with access to a heated resort-style pool, pavilion, dog park, and nearby Legacy Trail access. This corner-unit home combines luxury, privacy, and a central Sarasota location that puts beaches, culture, recreation, and shopping all within easy reach.

Full Property Details for 5099 Flag St

General

  • Price: $515,000
  • HOA FEE: $345/month
  • Taxes: $5,291 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4680473
  • Updated: 2/2/2026
  • Added to Site: 19 day(s) ago

Rental Information

  • Min. Lease: 6 Months

Interior

  • Number of Rooms: 7
  • Interior Features: Built-in Features, Ceiling Fan(s), High Ceilings, Kitchen and Family Room Combination, Open Floorplan, Pest Guard System, Split Bedroom, Stone Counters, Tray Ceiling(s), Walk-In Closet(s)
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Security/Safety: Gated Community

Exterior

  • Exterior Features: Irrigation System, Sidewalk, Sliding Doors

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway, Garage Door Opener

Location

  • Area: 34232 - Sarasota/Fruitville
  • County: Sarasota
  • Development Name: 34232 - Sarasota/Fruitville
  • Subdivision: ENCLAVE AT FOREST LAKES
  • Driving Directions: Rt 75 to Beeridge Rd exit head West towards Beneva road, head North(right) on Beneva Rd, take right on Tin Cup, right on Flag St, 5099 Flag is on the right.
  • Direction Faces: East

School Information

  • Elementary School: Wilkinson Elementary
  • Middle School: Brookside Middle
  • High School: Sarasota High

Community

  • Community Name: 34232 - Sarasota/Fruitville
  • Community Features: Community Mailbox, Deed Restrictions, Dog Park, Gated Community - No Guard, Pool, Sidewalks
  • Association: Yes
  • Assoc. Name: Craig Smith / Pinnacle CAM
  • Number of Pets: 2

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

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

Structural Information

  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Common Walls: End Unit
  • Stories/Levels: One
  • Square Feet: 1,647
  • Sq. Ft. Source: Public Records
  • Year Built: 2017

Lot Features

  • Property View: Garden
  • Lot Size (Acres): 0.09
  • Lot Size (Sq. Ft.): 4,125
  • Lot Size: 4125
  • Street/Road Desc.: Asphalt, Paved

Financial Considerations

  • Association Fee: $345
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $5,291
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 99, ENCLAVE AT FOREST LAKES, PB 49 PG 39
  • Flood Zone Info: x
  • APN: 60040129
  • Property ID: 60040129
  • Block/Lot/Section: 1

Listed by Berkshire Hathaway Homeservice

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Listing agent

— 5099 Flag St —

  • Berkshire Hathaway Homeservice

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 5099 Flag St

School District:Sarasota County School District
NameGradesDistance
Wilkinson Elementary School
3400 Wilkinson Road, Sarasota, FL 34231
PK-51.4 mi
Brookside Middle School
3636 South Shade Avenue, Sarasota, FL 34239
6-81.9 mi
Sarasota High School
2155 Bahia Vista Street, Sarasota, FL 34239
9-122.2 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 5099 Flag St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/02/2026
Listed
$515,000
42.49%
MLS
11/30/2017
Sold
$361,440
—
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 5099 Flag St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,627
-9%
$403,300
-1%
2024
$5,097
2%
$408,200
-4%
2023
$4,989
30%
$425,900
53%
2021
$3,837
-19%
$278,900
-31%
2022
$4,711
23%
$406,400
54%
2021
$3,837
5%
$264,000
1%
2019
$3,637
—
$261,800
-1%
2018
$3,648
344%
$264,300
263%
2017
$822
34%
$72,800
60%
2016
$612
—
$45,500
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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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 Berkshire Hathaway Homeservice

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5099 Flag Street, Sarasota, FL 34232 (MLS# A4680473) is a Single Family property with 2 bedrooms and 2 full bathrooms. 5099 Flag Street is currently listed for $515,000 and was received on February 02, 2026. Want to learn more about 5099 Flag Street? 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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