16 May Street, Saint Augustine, FL 32084

Local realty services provided by:Better Homes and Gardens Real Estate Lifestyles Realty
16 May Street,St. Augustine, FL 32084
$1,595,000
Virtual Tour
  • 4 Beds
  • 5 Baths
  • 4,495 sq. ft.
  • Single family
  • Active
Listed by: bryce ocepek
Office: coldwell banker anabasis realty
MLS#:2087301
Source:JV

Price summary

  • Price:$1,595,000
  • Price per sq. ft.:$322.81

About this home

Welcome to Pillars Castle, a breathtaking architectural masterpiece located at 16 May Street in the heart of St. Augustine, Florida. This iconic estate, originally built in the early 20th century, has been meticulously restored to preserve its historic charm while incorporating modern luxury throughout. Known for its ornate engineering and timeless design, Pillars Castle stands as a symbol of the city's rich heritage and offers a rare opportunity to own a fully licensed short-term rental in one of the most visited destinations in the country. Boasting over 4,400 square feet of living space, the property features four spacious bedrooms, four and a half bathrooms, a grand hall, formal dining room, chef's kitchen, custom bar, a private patio perfect for entertaining or relaxing in the ocean breeze. The original stained glass windows, coffered ceilings, and stone fireplaces speak to the historic character of the home, while updated guest suites with en-suite baths, spa showers, and

Contact an agent

contact an agent

Yes, I would like more information. Please use and/or share my information with a BHGRE®  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 a BHGRE®  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 (CENTURY 21® , Coldwell Banker® , Corcoran® , ERA® , Sotheby's International Realty® ). I acknowledge that I have read and agree to theTerms of useandPrivacy notice

Home facts

  • Year built:1925
  • Listing ID #:2087301
  • Added:247 day(s) ago
  • Updated:January 23, 2026 at 01:45 PM

Rooms and interior

  • Bedrooms:4
  • Total bathrooms:5
  • Full bathrooms:4
  • Half bathrooms:1
  • Living area:4,495 sq. ft.

Heating and cooling

  • Cooling:Central Air, Electric
  • Heating:Central, Electric, Heat Pump

Structure and exterior

  • Year built:1925
  • Building area:4,495 sq. ft.
  • Lot area:0.27 Acres

Utilities

  • Water:Public, Water Connected
  • Sewer:Sewer Connected

Finances and disclosures

  • Price:$1,595,000
  • Price per sq. ft.:$322.81
  • Tax amount:$15,932 (2024)
IDX information is provided exclusively for consumers‚ personal, non-commercial use that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate by NEFMLS. NEFMLS may, at its discretion, require use of other disclaimers as necessary to protect Participants and/or NEFMLS from liability.

New listings near 16 May Street