Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$1,300,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 2,340 Sq. Ft.
  • Updated 10 days ago
See This Home
Save This Home
See This Home
Save This Home
Short-Term Rental investment opportunity in the heart of Gulfport's Historic Art District! This fully furnished, Key West-inspired coastal retreat offers short-term vacation rental potential, breathtaking Boca Ciega Bay views, and an unbeatable walkable location just steps from downtown Gulfport's restaurants, galleries, waterfront parks, nightlife, and popular Tuesday Farmers Market. Whether you're seeking a high-performing Airbnb/VRBO property, second home, or full-time waterfront residence, this exceptional home delivers the perfect combination of lifestyle and income-producing potential. Guests and owners alike will love the private outdoor living spaces with panoramic water views overlooking Veteran's Park-ideal for morning coffee, sunset cocktails, and entertaining in true Florida style. Inside, coastal elegance meets modern luxury with an open-concept layout designed for comfort and hosting. The gourmet kitchen features stone countertops, extensive cabinetry, abundant storage, and premium finishes perfect for entertaining vacation guests or everyday living. The luxurious primary suite serves as a private sanctuary with a professionally designed walk-in closet system and a spa-inspired ensuite bath complete with a whirlpool tub, dual vanities, and oversized enclosed shower. The third floor features private outdoor decks off the primary, second, and third bedrooms, offering incredible sunset views and refreshing coastal breezes that make Gulfport one of Tampa Bay's most beloved waterfront communities. Built for durability, efficiency, and low-maintenance ownership, the home includes an elevator, impact-rated windows, Hardie plank siding, Trex decking, turf landscaping, and a whole-home solar system for significantly reduced electric costs. The oversized two-car garage provides ample room for vehicles, kayaks, jet skis, beach gear, or additional owner storage. Located just minutes from Downtown St. Petersburg, award-winning Gulf beaches, marinas, and Tampa Bay attractions, this rare turnkey short-term rental property is ready to generate income immediately while offering an incredible waterfront lifestyle. Opportunities like this in Gulfport's Historic Waterfront District are exceptionally rare.

Full Property Details for 5429 Essex Ave S

General

  • Price: $1,300,000
  • Taxes: $14,749 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: TB8457726
  • Updated: 6/12/2026
  • Added to Site: 98 day(s) ago

Rental Information

  • Min. Lease: 1-7 Days

Interior

  • Number of Rooms: 6
  • Interior Features: Elevator, Open Floorplan, PrimaryBedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s)
  • Appliances: Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Room

Exterior

  • Exterior Features: Balcony, French Doors, Sidewalk, Storage

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Alley Access

Location

  • Area: 33707 - St Pete/South Pasadena/Gulfport/St Pete Bch
  • County: Pinellas
  • Development Name: 33707 - St Pete/South Pasadena/Gulfport/St Pete Bch
  • Subdivision: BOCA CEIGA PARK
  • Driving Directions: From I-275, take Exit 19 for 22nd Ave S and head west. Continue on 22nd Ave S, then turn left onto 49th St S. Head south and turn right onto Gulfport Blvd S (FL-682). Continue west, then turn left onto 55th St S. Turn right onto Essex Ave S and continue to 5429 Essex Ave S, which will be on your right. Please note parking is limited on Essex so you may need to park in the back.
  • Direction Faces: South

School Information

  • Elementary School: Gulfport Elementary-PN
  • Middle School: Azalea Middle-PN
  • High School: Boca Ciega High-PN

Community

  • Community Name: 33707 - St Pete/South Pasadena/Gulfport/St Pete Bch

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Electricity Connected, Sewer Connected, Water Connected

Structural Information

  • Architectural Info: Key West
  • Architectural Style: Key West
  • Exterior Const.: Block, Cement Siding
  • Roof: Metal, Shingle
  • Windows: Blinds
  • Stories/Levels: Three Or More
  • Square Feet: 2,340
  • Sq. Ft. Source: Public Records
  • Year Built: 2012

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.09
  • Lot Size (Sq. Ft.): 3,833
  • Lot Size: 3833
  • Lot Dimensions: 40 x 95
  • Street/Road Desc.: Paved
  • Fencing (Description): Vinyl

Water Features

  • Water View: Yes

Green Features

  • Energy Generation: Solar

Financial Considerations

  • Tax Amount: $14,749.4
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: BOCA CEIGA PARK BLK D, LOT 13
  • Flood Zone Info: AE
  • APN: 333116096120040130
  • Property ID: 333116096120040130
  • Block/Lot/Section: D

Listed by Keller Williams St Pete Realty

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 5429 Essex Ave S —

  • Keller Williams St Pete Realty

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 5429 Essex Ave S

School District:Pinellas County School District
NameGradesDistance
Gulfport Montessori Elementary School
2014 52nd Street South, Gulfport, FL 33707
K-50.9 mi
Azalea Middle School
7855 22nd Ave N, St. Petersburg, FL 33710
6-84.5 mi
Boca Ciega High School
924 58th Street South, Gulfport, FL 33707
9-121.6 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 5429 Essex Ave S Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/17/2026
Listed
$1,300,000
14.04%
MLS
12/29/2023
Sold
$1,140,000
—
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 5429 Essex Ave S

Year
Property Taxes
Change
Tax Assessment
Change
2025
$14,210
-4%
$812,298
-6%
2024
$14,749
168%
$863,098
141%
2023
$5,511
1%
$357,870
6%
2021
$5,447
1%
$337,327
-3%
2022
$5,368
-1%
$347,447
4%
2021
$5,447
2%
$332,670
2%
2019
$5,349
1%
$325,191
2%
2018
$5,281
1%
$319,128
2%
2017
$5,242
1%
$312,564
2%
2016
$5,205
-2%
$306,135
1%
2015
$5,289
—
$304,007
1%
2014
$5,264
-19%
$301,594
-5%
2013
$6,494
—
$318,653
—
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.

Estimate the Cost for 5429 Essex Ave S

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Keller Williams St Pete Realty

Similar Properties near 5429 Essex Ave S

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

3516 21st Ave S, Saint Petersburg, FL 33711 - Photo 1 Just Listed
$1,250,000

3516 21st Ave S  Saint Petersburg, FL 33711

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 3,345
    Sq. Ft.
Listed by Exp Realty Llc
7886 9th Ave S, Saint Petersburg, FL 33707 - Photo 1 Price Reduced
-$25,000 (-1.96%)
$1,250,000

7886 9th Ave S  Saint Petersburg, FL 33707

  • Single Family
  • Active
  • Updated 5 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,355
    Sq. Ft.
Listed by Keller Williams St Pete Realty
3404 E Maritana Dr, Saint Pete Beach, FL 33706 - Photo 1
$1,225,000
Open House

3404 E Maritana Dr  Saint Pete Beach, FL 33706

  • Single Family
  • Active
  • Updated 10 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,324
    Sq. Ft.
Listed by Keller Williams St Pete Realty
1421 14th St N, Saint Petersburg, FL 33704 - Photo 1
$1,225,000

1421 14th St N  Saint Petersburg, FL 33704

  • Single Family
  • Active
  • 4
    Beds
  • 3
    Total Baths
  • 2,273
    Sq. Ft.
Listed by Reozom

Just Listed near 5429 Essex Ave S

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

7400 Sun Island Dr S, South Pasadena, FL 33707 - Photo 1 Just Listed
$279,900

7400 Sun Island Dr S  #111  South Pasadena, FL 33707

  • Condo
  • Active
  • Updated 3 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,300
    Sq. Ft.
Listed by Exp Realty Llc
7039 Hibiscus Ave S, South Pasadena, FL 33707 - Photo 1 Just Listed
$800,000
Open House

7039 Hibiscus Ave S  South Pasadena, FL 33707

  • Single Family
  • Active
  • Updated 20 hours ago
  • 3
    Beds
  • 4
    Total Baths
  • 2,227
    Sq. Ft.
Listed by The Agency Fl
3929 Belle Vista Dr, Saint Pete Beach, FL 33706 - Photo 1 Just Listed
$375,000

3929 Belle Vista Dr  Saint Pete Beach, FL 33706

  • Lots/Land
  • Active
  • Updated 3 days ago
  • 0.15
    Acres
Listed by Smith & Associates Real Estate
9415 Blind Pass Rd, Saint Pete Beach, FL 33706 - Photo 1 Just Listed
$529,500
Open House

9415 Blind Pass Rd  #706  Saint Pete Beach, FL 33706

  • Condo
  • Active
  • Updated 5 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,310
    Sq. Ft.
Listed by Compass Florida Llc

Price Reduced near 5429 Essex Ave S

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1868 Shore Dr S, South Pasadena, FL 33707 - Photo 1 Price Reduced
-$5,000 (-2.29%)
$212,999

1868 Shore Dr S  #503  South Pasadena, FL 33707

  • Condo
  • Active
  • Updated 3 days ago
  • 2
    Beds
  • 1
    Total Bath
  • 1,140
    Sq. Ft.
Listed by Bhhs Florida Properties Group
7300 Sun Island Dr S, South Pasadena, FL 33707 - Photo 1 Price Reduced
-$3,300 (-1.03%)
$317,700

7300 Sun Island Dr S  #602  South Pasadena, FL 33707

  • Condo
  • Active
  • Updated 6 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,120
    Sq. Ft.
Listed by Re/Max Action First Of Florida
1404 Corey Way S, South Pasadena, FL 33707 - Photo 1 Price Reduced
-$6,000 (-1.7%)
$347,000

1404 Corey Way S  South Pasadena, FL 33707

  • Single Family
  • Active
  • Updated 5 days ago
  • 2
    Beds
  • 1
    Total Bath
  • 920
    Sq. Ft.
Listed by Luxury & Beach Realty Inc
6700 Sunset Way, Saint Pete Beach, FL 33706 - Photo 1 Price Reduced
-$14,000 (-2.86%)
$475,000

6700 Sunset Way  #206  Saint Pete Beach, FL 33706

  • Condo
  • Active
  • Updated 3 days ago
  • 2
    Beds
  • 1
    Total Bath
  • 770
    Sq. Ft.
Listed by John Ross (727) 871-3611

Recent Sales near 5429 Essex Ave S

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

5421 Essex Ave S, Gulfport, FL 33707 - Photo 1 Sold
$1,475,000

5421 Essex Ave S  Gulfport, FL 33707

  • Single Family
  • Closed
  • 3
    Beds
  • 4
    Total Baths
  • 3,828
    Sq. Ft.
Listed by Beycome Of Florida Llc
Sold by Real Broker, Llc
2824 52nd St S, Gulfport, FL 33707 - Photo 1 Sold
$1,150,000

2824 52nd St S  Gulfport, FL 33707

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 2,432
    Sq. Ft.
Listed and Sold by Winway Realty
5947 Bayview Cir S, Gulfport, FL 33707 - Photo 1 Sold
$1,400,000

5947 Bayview Cir S  Gulfport, FL 33707

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 3,000
    Sq. Ft.
Listed by Candy Swick & Company
Sold by Keller Williams St Pete Realty
4322 26th Ave S, Gulfport, FL 33711 - Photo 1 Sold
$1,300,000

4322 26th Ave S  Gulfport, FL 33711

  • Single Family
  • Closed
  • 4
    Beds
  • 5
    Total Baths
  • 3,433
    Sq. Ft.
Listed and Sold by Reynolds Realty Gulf Coast Inc

5429 Essex Avenue S, Gulfport, FL 33707 (MLS# TB8457726) is a Single Family property with 4 bedrooms and 3 full bathrooms. 5429 Essex Avenue S is currently listed for $1,300,000 and was received on March 17, 2026. Want to learn more about 5429 Essex Avenue S? Do you have questions about finding other Single Family real estate for sale in Gulfport? You can browse all Gulfport real estate or contact a Coldwell Banker agent to request more information.

Tour this property