Features & Amenities

Interior

  • Other Interior Features

    Elevator, Cathedral Ceiling(s), Eat-in Kitchen, High Ceilings, Stone Counters, Walk-In Closet(s)

  • Total Bedrooms

    3

  • Bathrooms

    3

  • Cooling YN

    YES

  • Cooling

    Central Air, Zoned

  • Fireplace YN

    NO

  • Heating YN

    YES

  • Heating

    Central, Electric, Zoned

  • Pet friendly

    Cats OK, Dogs OK, Yes

Exterior

  • Garage

    Yes

  • Garage spaces

    2

  • Construction Materials

    Block, Stucco

  • Other Exterior Features

    Balcony, Lighting, Storage

  • Parking

    Driveway, Attached

  • Patio and Porch Features

    Covered, Patio, Wrap Around

  • Pool

    No

  • Waterfront YN

    NO

  • View

    Water, Park/Greenbelt

Area & Lot

  • Lot Features

    Corner Lot

  • Lot Size(acres)

    0.1

  • Lot Size(square feet)

    4,330

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Coastal

Price

  • Sales Price

    $1,300,000

  • Tax Amount

    $16,841

  • Financing Options

    Cash, Conventional, FHA, VA Loan

  • Sq. Footage

    3,051

  • Price/SqFt

    $426

HOA

  • Association

    No

School District

  • Elementary School

    Gulfport Elementary-PN

  • Middle School

    Thurgood Marshall Fund-PN

  • High School

    Boca Ciega High-PN

Property Features

  • New Construction

    NO

  • Foundation Details

    Slab

  • Ownership

    Fee Simple

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Tax Lot

    16

  • Water Source

    Public

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Location

County

Pinellas

Elementary School

Gulfport Elementary-PN

Middle School

Thurgood Marshall Fund-PN

High School

Boca Ciega High-PN

Listing Courtesy of John Blevins, GENSTONE REALTY

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Welcome to a turnkey, income-producing coastal retreat in the heart of Gulfport's Historic Waterfront Arts District. This Key West-inspired residence offers 3 bedrooms, 3 bathrooms, and 3,051 square feet of light-filled living space with sweeping views of Boca Ciega Bay and Veterans Park just steps from the front door.

Currently operating as a successful short-term rental, the home is being sold fully furnished and rental-ready — a rare opportunity to step into an established, cash-flowing vacation rental from day one. Existing bookings, guest reviews, and operating history are available to qualified buyers upon request, making this an ideal acquisition for investors, 1031 exchange buyers, or second-home owners seeking offset income.

Inside, soaring cathedral ceilings, a spacious great room, warm wood flooring, and a whole-house reverse osmosis system deliver the elevated finishes today's guests and homeowners expect. Multiple porches and balconies showcase the water views and capture Gulf breezes, while the layout comfortably sleeps a full group without sacrificing privacy.

Location is everything: a one-minute walk to Veterans Park and the Gulfport waterfront, minutes to the shops, restaurants, art galleries, and live music of Beach Boulevard, and a quick drive to St. Pete Beach, downtown St. Petersburg, and Tampa International Airport — the exact walkability and lifestyle that keep this property booked.

Whether you're expanding a short-term rental portfolio or looking for a coastal residence that pays for itself between visits, 5417 Essex Ave S is a rare turnkey offering in one of Florida's most sought-after small-town waterfront communities. STR certificate and licenses in place and transferable subject to city approval.

5417 ESSEX AVENUE S

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Related Properties

Welcome to a turnkey, income-producing coastal retreat in the heart of Gulfport's Historic Waterfront Arts District. This Key West-inspired residence offers 4 bedrooms, 2.5 bathrooms, and 3,804 square feet of light-filled living space with sweeping views of Boca Ciega Bay and Veterans Park just steps from the front door.

Currently operating as a successful short-term rental, the home is being sold fully furnished and rental-ready — a rare opportunity to step into an established, cash-flowing vacation rental from day one. Existing bookings, guest reviews, and operating history are available to qualified buyers upon request, making this an ideal acquisition for investors, 1031 exchange buyers, or second-home owners seeking offset income.

Inside, soaring cathedral ceilings, a spacious great room, warm wood flooring deliver the elevated finishes today's guests and homeowners expect. Multiple porches and balconies showcase the water views and capture Gulf breezes, while the layout comfortably sleeps a full group without sacrificing privacy.

Location is everything: a one-minute walk to Veterans Park and the Gulfport waterfront, minutes to the shops, restaurants, art galleries, and live music of Beach Boulevard, and a quick drive to St. Pete Beach, downtown St. Petersburg, and Tampa International Airport — the exact walkability and lifestyle that keep this property booked.

Whether you're expanding a short-term rental portfolio or looking for a coastal residence that pays for itself between visits, 5433 Essex Ave S is a rare turnkey offering in one of Florida's most sought-after small-town waterfront communities. STR certificate and licenses in place and transferable subject to city approval.
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NEW ROOF, NEW A/C SYSTEM, AND NEW SPRINKLER SYSTEM! Welcome to 2706 Skimmer Point Drive S, an exceptional 4-bedroom, 3-bath residence offering approximately 2,674 square feet of living space in the prestigious gated community of Pasadena Yacht & Country Club.

This beautifully appointed home offers a spacious and inviting floor plan with soaring ceilings, abundant natural light, and generous living areas designed for both everyday comfort and entertaining. The kitchen features custom cabinetry, ample counter space, stainless steel appliances, a breakfast bar, and natural gas cooking, opening to a spacious family room highlighted by a cozy gas fireplace and views of the pool area.

The private primary suite provides a relaxing retreat with dual walk-in closets, French doors leading to the screened lanai, and a spacious en-suite bathroom featuring separate vanities, a soaking tub, and separate shower. Three additional bedrooms offer plenty of flexibility for family, guests, or a home office.

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Located within the highly desirable Pasadena Yacht & Country Club community, this property offers the privacy and security of gated living while remaining conveniently close to Gulfport’s vibrant waterfront district, restaurants, shopping, beautiful Gulf beaches, downtown St. Petersburg, and Tampa International Airport.

A rare opportunity to enjoy space, privacy, and the Florida lifestyle in one of Gulfport’s most sought-after communities. Schedule your private showing today!
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Virtually Staged. Welcome to a beautifully reimagined piece of Gulfport history in Pasadena Estates—a 1920s Spanish-Mediterranean gem on a sprawling 1/3-acre lot. Meticulously restored, this residence honors its architectural heritage w/ original arches, beamed vaulted ceilings & exquisite woodwork throughout, complemented by deco-stucco interior walls. Featuring beautiful hardwood floors alongside elegant wood-look tile, every room radiates warmth and style. W/ 3-4 beds & 2 full/2 half baths, it artfully blends thoughtful, high-end renovations for modern comfort while retaining its historic charm. Venture through the grand foyer into a sun-drenched formal parlor anchored by a classic wood-burning fireplace and handcrafted details, incl. authentic corbels & exposed beams. Entertain in elegance in the formal dining rm, which features a stunning crystal chandelier & opens through French doors to a picturesque Spanish courtyard w/ a tranquil old-world fountain. The chef's kitchen is a showstopper w/ wood cabinetry, granite counters, premium appliances incl. a new 2026 dishwasher, designer lighting & a luxurious quartz island. A spacious Butler's Pantry connects directly to a powder rm, complete w/ a well-appointed wet bar & fridge—perfect for entertaining guests or hosting special occasions. Adjacent spaces incl. a mudroom w/ updated electrical panel (2020), a 4th bed/flex rm, cleverly concealed laundry closet & half bath. The family rm features shiplap built-ins & seamless indoor-outdoor living. The sparkling saltwater pool was resurfaced less than a yr. ago, w/ a new pump & saltwater system replaced in 2023. Enjoy the lovely, landscaped grounds & a firepit set on easy-maintenance artificial turf. Upstairs, the renovated primary suite is a sanctuary, boasting a spa-inspired bath w/ Italian Carrara marble, custom glass & a designer double vanity, plus an expertly crafted dressing closet. Add'l rms retain vintage charm w/ original fixtures & a restored cast-iron tub. Recent upgrades—incl. a new 2025 roof, hurricane-rated doors, new 2nd-fl. A/C (July 2025), serviced & inspected downstairs A/C, Renewal by Andersen® windows, spray foam insulation, updated plumbing & more—ensure lasting peace of mind for buyers seeking a move-in ready, storm-ready historic home in Gulfport, FL. The property also offers natural gas—a valuable feature for buyers seeking energy flexibility & efficiency. Uninterrupted Terminix pest control service since purchase provides an additional layer of protection and confidence for the next owner. The current owners beautifully redesigned the front w/ landscaping & brick pavers, creating a welcoming circular drive & convenient guest parking. The detached 2-car garage offers the owners exclusive rear-entry access—perfect for added privacy and ease—and is equipped w/ 2 add'l electrical panels. All of this is just mins. from Gulfport Beach, St. Pete Beach, Pasadena Yacht & Country Club & downtown St. Petersburg. Nestled in the heart of Gulfport, FL—known for its small-town charm & vibrant local culture—enjoy tree-lined streets, art galleries, shops & eateries. Gulfport Beach and the Recreation Center are nearby for swimming & kayaking, and parks offer scenic views & outdoor activities. Year-round events like art fairs & farmers' markets, Maynard Duryea Bayview Park & Treasure Island Beach are just a short drive away.
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