Photography
Life Above Beach Drive
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The only full-floor penthouse on Beach Drive with four-car parking and five-balcony panoramic views
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For buyers visiting from out of state or internationally, a listing without video is one that does not get a showing. These four video assets are commissioned as part of the relaunch — contact us for current availability.
Occupying the entire 14th floor of The Cloisters — one of downtown St. Petersburg's most celebrated boutique buildings — Penthouse 2A is a study in what it means to live above it all. Designed by acclaimed architect Randy Wedding, the same visionary behind the historic Vinoy restoration, this full-floor residence commands 5,100 square feet of sunrise-to-sunset splendor.
Five private balconies frame every perspective: Tampa Bay shimmering at dawn, the Vinoy Basin at noon, the St. Pete Pier and Sunshine Skyway Bridge at dusk, and the city's skyline glittering at night. Four assigned, covered, ground-level parking spaces — an extraordinary rarity in downtown St. Pete — complete a lifestyle package no newly constructed tower can replicate.
This is the penthouse for the buyer who wants the privacy of a private home, the security of a staffed building, and the irreplaceable walkability of the finest street in St. Petersburg.
Every window is a painting. Five balconies frame a different story depending on the hour.
In any dense urban core, parking is scarce. In downtown St. Petersburg, four assigned, covered, ground-level spaces for a single residence is virtually unheard of. Saltaire — the newest luxury tower in the market — offers one space standard. 400 Central offers one to two. This penthouse offers four.
If purchased separately in today's market, four prime downtown parking spaces would cost an estimated $200,000–$400,000. They are included.
At this level, full transparency is not optional — it is a mark of confidence. Here is every carrying cost, fully itemized, alongside the important context that changes the math.
Buyers often compare this penthouse to a luxury house at a similar price. Here is why the comparison is more nuanced than the HOA headline suggests.
In today's Florida condo market, sophisticated buyers require full documentation before committing. A complete Buyer Confidence Package is available upon request for all qualified buyers.
Florida's SB 154 compliance documentation available. Milestone inspection records and Structural Integrity Reserve Study (SIRS) status provided to qualified buyers as required by Florida law.
HOA reserve study and funded ratio available for review. The Cloisters is a 32-unit boutique community with a strong history of responsible building management since 1999.
Building-level master insurance policy summary available. Coverage includes the structure, exterior, common areas, and provides significant relief from individual flood and wind insurance obligations.
Current and pending special assessment status disclosed upfront. No surprises. Full HOA budget with line-item detail available to serious buyers at the first showing.
Complete history of building capital investments — roof, elevators, mechanical systems, lobby, and common areas — available for review. A 25-year building history is a track record, not a liability.
All Florida DBPR-required disclosure documents prepared and ready. Our commitment: every serious buyer receives complete documentation within 24 hours of a confirmed showing.
The Cloisters was the first of the new-generation luxury condominiums on Beach Drive — setting the standard that every building since has aspired to meet.
Beach Drive is not a location — it is a lifestyle. Directly on Straub Park, steps from the Museum of Fine Arts, the St. Pete Pier, and the Vinoy Renaissance Resort, 288 Beach Drive places world-class dining, culture, and waterfront access literally outside your door.
288 Beach Dr NE sits directly on the waterfront promenade of Beach Drive — the most prestigious address in downtown St. Petersburg. The building occupies the intersection of Beach Drive and 2nd Ave NE, providing immediate access to the city's cultural corridor, the waterfront, and the Vinoy Basin marina.
At $931/SF, Penthouse 2A is priced below every comparable nearby luxury condo — in some cases by 50% or more per square foot. Here is the full competitive picture.
| Property | Price | Sq Ft | $/SF | Year Built | HOA / Mo | Key Note |
|---|---|---|---|---|---|---|
| 288 Beach Dr NE PH-2A This Property | $4,750,000 | 5,100 | $931 | 1999 | $6,891 | Full floor · 5 balconies · 4 parking · Beach Drive address |
| 180 Beach Dr NE #1401 | $5,100,000 | 3,660 | $1,393 | 2010 | $3,867 | Same address corridor; lower HOA but only 3,660 SF |
| Saltaire 275 1st Ave S #4101 New | $4,599,000 | 3,157 | $1,457 | 2025 | $1,397 | Brand new; lower HOA but 38% less space than subject |
| Saltaire 275 1st Ave S #4204 New | $5,524,000 | 3,157 | $1,750 | 2025 | TBD | Premium new construction; $819 more per SF |
| 400 Central Ave PH 4102 New | $4,795,000 | TBD | $1,500+ | 2025 | TBD | Near-identical ask; new construction premium pricing |
| 150 2nd Ave S #3903 | $4,200,000 | 2,583 | $1,626 | Recent | TBD | Almost half the square footage for similar price |
| 100 Beach Dr NE #1900 | $5,800,000 | 4,960 | $1,169 | TBD | TBD | Comparable size; priced $1.05M higher |
Houses at this price point offer more bedrooms and no HOA — but when you factor in flood insurance, wind coverage, and maintenance costs, the gap narrows significantly.
| House Property | Price | Sq Ft | $/SF | Beds | Baths | HOA | Est. Flood + Wind Ins./yr |
|---|---|---|---|---|---|---|---|
| 288 Beach Dr PH-2A This Property | $4,750,000 | 5,100 | $931 | 3 | 2.5 | $82,692/yr* | Covered by master policy |
| 838 Monterey Blvd NE | $4,750,000 | 4,334 | $1,096 | 5 | 5 | None | Est. $25,000–$55,000+ |
| 1401 Brightwaters Blvd NE | $4,950,000 | 5,255 | $942 | 4 | 5.5 | None | Est. $25,000–$55,000+ |
| 1097 Eden Isle Dr NE | $4,295,000 | 6,015 | $714 | 5 | 5 | None | Est. $25,000–$55,000+ |
| 750 Cordova Blvd NE | $3,895,000 | 4,948 | $787 | 5 | 5.5 | None | Est. $25,000–$55,000+ |
*HOA covers building master insurance including flood and wind components. Individual insurance requirements for this unit are minimal. House insurance estimates are indicative for Pinellas County waterfront properties; actual costs vary by coverage, carrier, and structure. All property data from public listings as of April 2026.
This residence is shown by private appointment only. Qualified buyers are invited to experience the full-floor scale, the panoramic views, and the arrival experience that no photograph can fully convey.
This website is provided for informational purposes. All information is deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change, or withdrawal. Listing courtesy of Smith & Associates Real Estate / Stellar MLS. Information current as of April 2026.