5099 Flag St

Sarasota, FL 34232

$515,000
Price
2
Beds
1,647 Sq. Ft.
$313 / Sq. Ft.
1,647
Sq. Ft.
$313
per Sq. Ft.
Open: 2/22 01:00PM - 05:00PM
Open: 2/22 01:00PM - 05:00PM

Description

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...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.
  1. Listed by Ellen Wilson • Brokerage DRE #2028017 • BERKSHIRE HATHAWAY HOMESERVICE
    P: (704)-651-6322 C: (704)-651-6322 TeamWilsonflhomes@gmail.com

Property Details for 5099 Flag Street

Subdivision Name
ENCLAVE AT FOREST LAKES
Township
36S
Garage Spaces
2
View
Garden
Waterfront
No
Furnished
Unfurnished

Open Houses

Sunday, Feb 22nd

1:00 PM - 5:00 PM

Public

LISTING UPDATED: 02/18/2026 02:24 PM

Property Details for 5099 Flag Street

StatusActive
MLS #A4680473
Days on Market20
Taxes$5,291 / year
HOA Fees$4,140 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Villa
Year Built2017
Lot Size0.09 AC / 4,125 SF
CountySarasota County

Location

Listing Courtesy of BERKSHIRE HATHAWAY HOMESERVICE, Ellen Wilson
Add your commute

Building Information for 5099 Flag Street

Stories1Year Built2017Building Size-Lot Size0.09 AC / 4,125 SF

Payment Calculator

$3,296 per month

30 year fixed, 6.15% Interest

Principal and Interest

$2,510

Property Taxes

$441

HOA Dues

$345

The Payment Calculator is for illustrative purposes only.

Property Information for 5099 Flag Street

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 2294.0
  • Building Area Units: Square Feet
  • Community Features: Community Mailbox, Deed Restrictions, Dog Park, Gated Community - No Guard, Pool, Sidewalks
  • Direction Faces: East
  • 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.
  • Elementary School: Wilkinson Elementary
  • Middle Or Junior School: Brookside Middle
  • High School: Sarasota High
  • Mls Major Change Type: New Listing
  • Major Change Type: New Listing
  • Listing Service: Full Service
  • Senior Community: No
  • SW Subdiv Community Name: Enclave at Forest Lakes
  • Unit Number: No
  • Street Number: 5099
  • Street Name: FLAG
  • Street Suffix: STREET
  • State: FL
  • City: SARASOTA
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Driveway, Garage Door Opener
Taxes and HOA Information
  • Association Approval Required: No
  • Association Fee Requirement: Required
  • Association Name: Craig Smith / Pinnacle CAM
  • Association Phone: 941-444-7090
  • Association: Yes
  • CDD: No
  • Number Of Pets: 2
  • Tax Block: 1
  • Tax Book Number: 49-39
  • Tax Legal Description: LOT 99, ENCLAVE AT FOREST LAKES, PB 49 PG 39
  • Tax Lot: 99
  • Tax Year: 2025
Property
Lot Information
  • Additional Parcels: No
  • Parcel Number: 0060040129
  • Total Acreage: 0 to less than 1/4
  • Water Access: No
  • Water Extras: No
  • Zoning: RSF3
  • Living Area: 1647
  • Property Info: End Unit
Property and Assessments
  • Year Built Numeric: 2017
  • Flood Zone Code: x
  • Home Warranty: No
  • Homestead: No
  • New Construction: No
  • Public Survey Range: 18E
  • Public Survey Section: 34
Utilities
  • Sewer: Public Sewer
  • Utilities: Cable Available, Electricity Connected, Public, Sewer Connected, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Block, Stucco
  • Exterior Features: Irrigation System, Sidewalk, Sliding Doors
  • Foundation Details: Slab
  • Levels: One
  • Pool Private: No
  • Pool: Community
  • Pool Private: Yes
  • Roof: Shingle
  • Security Features: Gated Community
  • Waterfront Feet Total: 0
  • Number Of Stories: 1
Interior Features
  • Bedrooms Total: 2
  • Bathrooms Full: 2
  • Additional Rooms: Den/Library/Office
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Refrigerator, Washer
  • Cooling: Central Air
  • Fireplace: No
  • Flooring: Tile, Hardwood
  • Heating: Central
  • Interior Features: Built-in Features, Ceiling Fan(s), High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Pest Guard System, Split Bedroom, Stone Counters, Tray Ceiling(s), Walk-In Closet(s)
  • Laundry Features: Laundry Room
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 7.0
  • Water View: No
  • Bathrooms Half: 0
Rental
Rental Information
  • Minimum Lease Period: 1
  • Pets Allowed: Yes

Property History for 5099 Flag Street

DateEvent & SourcePriceAppreciation
Feb 2, 2026

Listed (Active)

MFRMLS #A4680473

$515,000—
Jul 1, 2025

Withdrawn

MFRMLS #A4638206

$529,900—
Feb 1, 2025

Listed (Active)

MFRMLS #A4638206

$535,000—
Nov 30, 2017

Sold (Public Record)

Public Record #611236652

$361,440—
DateEvent & SourcePrice
02/02/2026

Listed (Active)

MFRMLS #A4680473

$515,000
07/01/2025

Withdrawn

MFRMLS #A4638206

$529,900
02/01/2025

Listed (Active)

MFRMLS #A4638206

$535,000
11/30/2017

Sold (Public Record)

Public Record #611236652

$361,440

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 5099 Flag Street

Taxable ValueLand$115,400Additions$287,900Total$403,300
Tax Record2025$4,627 ($386 / month)
Home Facts
Baths2Total Finished SqFt1,647 SqFtAbove Grade Finished SqFt1,647 SqFtStories1Lot Size4,125 SqFtStyleDuplexYear Built2017ZoningRSF3; PUDCountySARASOTAAPN0060-04-0129

Schools near 5099 Flag Street

This home is within Sarasota.
Rating
School
Type
Grades
Distance
Wilkinson Elementary School
Public - PK to 5
Brookside Middle School
Public - 6 to 8
Sarasota High School
Public - 9 to 12
Triad Alternative School
Public - 6 to 12
Rating
School
Distance
Wilkinson Elementary School
PublicPK to 5

Brookside Middle School
Public6 to 8

Sarasota High School
Public9 to 12

Triad Alternative School
Public6 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 5099 Flag Street, Sarasota, FL 34232

5099 Flag Street is a single family home for sale in Sarasota, FL 34232. This property was listed for sale on February 2, 2026 by BERKSHIRE HATHAWAY HOMESERVICE, it's currently listed at $515,000. It has been on the market for a total of 20 days and was last sold on November 30, 2017. This listing's school district is Sarasota. Nearby schools include Wilkinson Elementary School, Brookside Middle School and Sarasota High School. 5099 Flag Street is a 2-bed, 2-bath, 1,647 sqft single family home built in 2017.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of BERKSHIRE HATHAWAY HOMESERVICE, Ellen Wilson

The information is being provided in part by Southwest Florida Multiple Listing Service, Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2, and MarcoMls. Information deemed reliable but not guaranteed. Information is provided for consumers' personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2026 Southwest Florida Multiple Listing Service and MarcoMls. All Rights Reserved. The data relating to real estate for sale displayed on this website comes in part from the Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2 and MarcoMls. Properties listed with brokerage firms other than Compass are marked with the "BR House" logo. Detailed information about such properties includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties listed with brokerage firms participating in the Naples MLS BR Program, or contained in the database compilation of Naples MLS.