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16 May Street

St. Augustine, FL 32084
  • $1,695,000
  • STATUS: Active
  • ON SITE: 40 Days
  • MLS #: 2087301
Open House
UPDATED: 71 min ago
$1,695,000
  • 4
    BEDS
  • 0.27
    ACRES
  • 4
    BATHS
  • 1
    1/2 BATHS
  • 4,495
    SQFT
  • $377
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1925
County:

School Ratings & Info

Description

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 premium finishes provide comfort and sophistication. The beautifully landscaped courtyard with a fountain and gated rear-entry adds to the estate's privacy and elegance, and ample off-street parking is a rare amenity in the downtown area. The property has a detached two-car garage, a covered carport, and an elongated driveway with plenty of parking that also allows you to exit through the rear of the property via the service road. Just minutes from the beaches, Castillo de San Marcos, the Fountain of Youth, Flagler College, and the shops and restaurants of St. George Street; the location is ideal for vacationers and history lovers alike. Actively operating as a luxury vacation rental, Pillars Castle commands premium nightly rates, making it both a stunning private residence and an exceptional investment opportunity. One of the bedrooms and bathrooms has a separate entrance with kitchenette and can be closed off to operate as a separate standalone rental unit or mother-in-law suite. Not to mention, furniture and everything within the property stays at the asking price!Don't miss this chance to own a piece of St. Augustine's living history--Pillars Castle offers the prestige, flexibility, and income rarely found in one extraordinary property.

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© 2025 Northeast Florida Multiple Listing Service, Inc. All rights reserved. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of the Northeast Florida Multiple Listing Service, Inc. Real estate listings held by brokerage firms other than St. Augustine Realty are marked with the listing broker’s name and detailed information about such listings includes the name of the listing brokers. Data provided is deemed reliable but is not guaranteed. Data last updated 2025-06-23T16:25:35.707.

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16 May Street St. Augustine, FL 32084

  • Price: $1,695,000
  • Status: Active
  • On Site: 40 Days
  • Updated: 71 min ago
  • MLS #: 2087301
4
Beds
4
Baths
1
½ Baths
0.27
Acres
4,495
SQFT
$377
$/SQFT
1925
Built
Neighborhood:
Nelmar Terrace
County:
St. Johns
Area:
321-NORTH CITY-ST AUGUSTINE
Property Description
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 premium finishes provide comfort and sophistication. The beautifully landscaped courtyard with a fountain and gated rear-entry adds to the estate's privacy and elegance, and ample off-street parking is a rare amenity in the downtown area. The property has a detached two-car garage, a covered carport, and an elongated driveway with plenty of parking that also allows you to exit through the rear of the property via the service road. Just minutes from the beaches, Castillo de San Marcos, the Fountain of Youth, Flagler College, and the shops and restaurants of St. George Street; the location is ideal for vacationers and history lovers alike. Actively operating as a luxury vacation rental, Pillars Castle commands premium nightly rates, making it both a stunning private residence and an exceptional investment opportunity. One of the bedrooms and bathrooms has a separate entrance with kitchenette and can be closed off to operate as a separate standalone rental unit or mother-in-law suite. Not to mention, furniture and everything within the property stays at the asking price!Don't miss this chance to own a piece of St. Augustine's living history--Pillars Castle offers the prestige, flexibility, and income rarely found in one extraordinary property.
Exterior Features

Architectural Style Historic Body Type [] Carport Spaces 1 Construction Materials [] Entry Level 1 Exterior Features [] Fencing [] Lot Features [] Other Structures [] Parking Features Additional ParkingAttached CarportCarportCoveredDetachedGarageOff Street Patio And Porch Features [] Pool Features [] Road Surface Type [] Roof [] Spa Features [] View [] Waterfront Features [] Waterfront YN No

Interior Features

Appliances Convection OvenDishwasherDisposalDryerElectric CooktopElectric OvenElectric RangeElectric Water HeaterFreezerIce MakerMicrowaveRefrigeratorWasher Cooling Central AirElectricMulti Units Cooling YN Yes Fireplace Features [] Fireplace YN Yes Fireplaces Total 1 Flooring CarpetLaminateTile Furnished Furnished Heating CentralElectricHeat Pump Heating YN Yes Interior Features Ceiling Fan(s)Eat-in KitchenGuest SuiteHis and Hers ClosetsIn-Law FloorplanKitchen IslandPrimary Bathroom - Tub with ShowerVaulted Ceiling(s)Wet Bar Laundry Features [] Rooms Total 0

Property Features

Accessibility Features [] Association Amenities [] Association Fee Includes [] Association YN No Attached Garage YN No Cdd Fee YN No Current Use InvestmentResidentialSingle Family Dpr Eligible YN No Electric [] Green Energy Efficient [] Green Water Conservation [] Listing Terms CashConventional New Construction YN No Possession Close Of Escrow Property Attached YN No Property Condition Updated/Remodeled Property Sub Type Single Family Residence Security Features [] Senior Community YN No Sewer [] Utilities Cable ConnectedElectricity ConnectedSewer ConnectedWater Connected Water Source Public Zoning Residential

Listing courtesy of COLDWELL BANKER ANABASIS REALTY: 904-351-0765.


© 2025 Northeast Florida Multiple Listing Service, Inc. All rights reserved. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of the Northeast Florida Multiple Listing Service, Inc. Real estate listings held by brokerage firms other than St. Augustine Realty are marked with the listing broker’s name and detailed information about such listings includes the name of the listing brokers. Data provided is deemed reliable but is not guaranteed. Data last updated 2025-06-23T16:25:35.707.

Digital Millennium Copyright Act
 
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