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14257 N Bayshore Drive, Madeira Beach, FLVideo Tour of 14257 N Bayshore Drive, Madeira Beach, FL.
Opportunities galore await at this premier waterfront gem, perfectly positioned on the tranquil waters of Boca Ciega Bay and just one block from the pristine sands of Madeira Beach. Boasting a "grandfathered-in" commercial designation that allows for a high-density renovation of five to nine units, this property also offers the flexibility to tear down and start anew. Whether you envision an extra-large single-family estate with an Accessory Dwelling Unit (ADU), a luxury duplex, or the construction of up to three sophisticated townhomes, the R2 zoning and generous lot size provide a rare canvas for your vision. This site comes complete with a dock included, serving as the perfect launchpad to experience unobstructed sunrises across an expanse of water toward a distant national park. From the mid-morning sparkle of sunlight on the bay to the late afternoon light painting the facades of neighboring residences, life here is defined by natural beauty and the gorgeous waterfront location. Whether you are an investor seeking a multi-unit project or a homeowner building a legacy sanctuary, this property is a coastal masterpiece in the making.

Full Property Details for 14257 N Bayshore Dr

General

  • Price: $1,400,000
  • Taxes: $13,622 (2025)
  • Status: Active
  • Type: Commercial
  • Source: MidFloridaRegionalMLS
  • MLS ID: TB8489683
  • Updated: 3/27/2026
  • Added to Site: 2 day(s) ago

Location

  • Area: 33708 - St Pete/Madeira Bch/N Redington Bch/Shores
  • County: Pinellas
  • Development Name: 33708 - St Pete/Madeira Bch/N Redington Bch/Shores
  • Subdivision: GULF SHORES 1ST ADD
  • Driving Directions: From I-75 North (coming from Tampa/Bradenton) Take I-75 S to exit 228 for I-275 N toward St. Petersburg. Cross the Sunshine Skyway Bridge (toll). Take exit 25 for 38th Ave N. Follow 38th Ave N west, then merge onto Tyrone Blvd / Bay Pines Blvd (FL-666). Continue west across the Tom Stuart Causeway into Madeira Beach. Turn right (north) onto Gulf Blvd. Turn right onto 140th Ave, then a quick left onto Bayshore Dr.

Community

  • Community Name: 33708 - St Pete/Madeira Bch/N Redington Bch/Shores

Heating & Cooling

  • Cooling Type: None

Utilities

  • Sewer: Public Sewer
  • Water District: BOCA CIEGA BAY
  • Water: Public
  • Utility Description: Public

Structural Information

  • # Buildings: 1
  • Exterior Const.: Block
  • Square Feet: 3,072
  • Sq. Ft. Source: Public Records
  • Year Built: 1952

Lot Features

  • Lot Size (Acres): 0.21
  • Lot Size (Sq. Ft.): 9,357
  • Lot Size: 9357
  • Lot Dimensions: 81 x 117
  • Frontage: City Street
  • Street/Road Desc.: Asphalt

Water Features

  • Water Front: Yes
  • Water Access: Yes
  • Water Access Desc: Bay/Harbor, Canal - Saltwater, Gulf/Ocean, Intracoastal Waterway
  • Water Extras: Yes
  • Water Front Name: BOCA CIEGA BAY
  • Water Front Desc.: Saltwater Canal

Financial Considerations

  • Tax Amount: $13,622.44
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: GULF SHORES 1ST ADD BLK E, LOTS 1 & 2 TOGETHER WITH TIIF SLL #520346313 O.R. 17436/2029 EXP 4/22/2016
  • Flood Zone Info: AE
  • APN: 103115343260050010
  • Property ID: 103115343260050010
  • Block/Lot/Section: E

Listed by Redfin Corporation

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— 14257 N Bayshore Dr —

  • Redfin Corporation

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NMLS#: 1598647

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with our affiliated lender
NMLS#: 1598647

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Schools serving 14257 N Bayshore Dr

School District:Pinellas County School District
NameGradesDistance
Orange Grove Elementary School
10300 65th Avenue North, Seminole, FL 33772
K-52.4 mi
Seminole Middle School, Seminole, FL
8701 131st Street North, Seminole, FL 33776
6-84 mi
Seminole High School, Seminole, FL
8401 131st Street North, Seminole, FL 33776
9-123.8 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 14257 N Bayshore Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/27/2026
Listed
$1,400,000
8.95%
MLS
11/08/2016
Sold
$1,285,000
—
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 14257 N Bayshore Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$13,622
-11%
$840,000
-31%
2024
$15,355
8%
$1,225,000
10%
2023
$14,225
27%
$1,110,000
54%
2021
$11,233
-12%
$721,000
-25%
2022
$12,756
14%
$965,000
72%
2021
$11,233
20%
$562,135
6%
2019
$9,338
3%
$532,000
—
2018
$9,095
3%
$530,000
5%
2017
$8,817
41%
$505,000
35%
2016
$6,250
12%
$375,000
23%
2015
$5,556
-4%
$305,000
-5%
2014
$5,798
-3%
$320,400
-3%
2013
$5,983
—
$330,000
—
View All
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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Listed by Redfin Corporation

Just Listed near 14257 N Bayshore Dr

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15612 Gulf Blvd, Redington Beach, FL 33708 - Photo 1 Just Listed
$6,995,000

15612 Gulf Blvd  Redington Beach, FL 33708

  • Single Family
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  • Updated 5 days ago
  • 4
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  • 5
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  • 4,006
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Listed by Smith & Associates Real Estate
203 163rd Ave, Redington Beach, FL 33708 - Photo 1 Just Listed
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203 163rd Ave  Redington Beach, FL 33708

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Listed by Coastal Properties Group International
16007 Gulf Blvd, Redington Beach, FL 33708 - Photo 1 Just Listed
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16007 Gulf Blvd  Redington Beach, FL 33708

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  • Updated 2 days ago
  • 4
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Listed by Your Neighborhood Realty Assoc
15825 Redington Dr, Redington Beach, FL 33708 - Photo 1 Just Listed
$1,645,000

15825 Redington Dr  Redington Beach, FL 33708

  • Lots/Land
  • Active
  • Updated 4 days ago
  • 0.7
    Acres
Listed by Re/Max Action First Of Florida

Price Reduced near 14257 N Bayshore Dr

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16129 4th St E, Redington Beach, FL 33708 - Photo 1 Price Reduced
-$26,000 (-2.42%)
$1,049,000

16129 4th St E  Redington Beach, FL 33708

  • Single Family
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 2
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  • 1,428
    Sq. Ft.
Listed by Engel & Volkers Madeira Beach
204 160th Ave, Redington Beach, FL 33708 - Photo 1 Price Reduced
-$14,900 (-2.01%)
$725,000

204 160th Ave  Redington Beach, FL 33708

  • Single Family
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,408
    Sq. Ft.
Listed by Redfin Corporation
16308 Gulf Blvd, Redington Beach, FL 33708 - Photo 1 Price Reduced
-$10,000 (-1.59%)
$619,000

16308 Gulf Blvd  #209  Redington Beach, FL 33708

  • Condo
  • Active
  • Updated 3 days ago
  • 2
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  • 2
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  • 1,065
    Sq. Ft.
Listed by Engel & Volkers Tampa Downtown
16333 Gulf Blvd, Redington Beach, FL 33708 - Photo 1 Price Reduced
-$51,000 (-11.33%)
$399,000

16333 Gulf Blvd  #201  Redington Beach, FL 33708

  • Single Family
  • Active
  • Updated 5 days ago
  • 1
    Bed
  • 1
    Total Bath
  • 550
    Sq. Ft.
Listed by Florida Driven Real Estate

Recent Sales near 14257 N Bayshore Dr

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460 137th Ave Cir, Madeira Beach, FL 33708 - Photo 1 Sold
$1,610,000

460 137th Ave Cir  Madeira Beach, FL 33708

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 2,574
    Sq. Ft.
Listed by Abi Road Realty Llc
Sold by The Pithers Group
565 Crystal Dr, Madeira Beach, FL 33708 - Photo 1 Sold
$1,200,000

565 Crystal Dr  Madeira Beach, FL 33708

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,253
    Sq. Ft.
Listed by Charles Rutenberg Realty Inc
Sold by Redfin Corporation
249 Boca Ciega Dr, Madeira Beach, FL 33708 - Photo 1 Sold
$1,200,000

249 Boca Ciega Dr  Madeira Beach, FL 33708

  • Lots/Land
  • Closed
  • Updated 5 days ago
  • 0.29
    Acres
Listed and Sold by Charles Rutenberg Realty Inc
437 Boca Ciega Dr, Madeira Beach, FL 33708 - Photo 1 Sold
$1,350,000

437 Boca Ciega Dr  Madeira Beach, FL 33708

  • Lots/Land
  • Closed
  • 0.15
    Acres
Listed by Century 21 Beggins
Sold by Century 21 Be3

14257 N Bayshore Drive, Madeira Beach, FL 33708 (MLS# TB8489683) is a Commercial property. 14257 N Bayshore Drive is currently listed for $1,400,000 and was received on March 27, 2026. Want to learn more about 14257 N Bayshore Drive? Do you have questions about finding other Commercial real estate for sale in Madeira Beach? You can browse all Madeira Beach real estate or contact a Coldwell Banker agent to request more information.

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