$1,595,000
Price
4
Beds
4,495 Sq. Ft.
$355 / Sq. Ft.
4,495
Sq. Ft.
$355
per Sq. Ft.

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...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
  1. Listed by BRYCE OCEPEK • COLDWELL BANKER ANABASIS REALTY
    P: (904)-206-9965 bryceocepek@gmail.com

Property Details for 16 May Street

Architectural Style
Historic
Senior Community YN
No
Subdivision Name
Nelmar Terrace
LISTING UPDATED: 11/13/2025 07:02 AM

Property Details for 16 May Street

StatusActive
MLS #2087301
Days on Market236
Taxes-
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1925
Lot Size0.27 AC / 11,761 SF
CountySt. Johns County

Location

Listing Courtesy of COLDWELL BANKER ANABASIS REALTY
Add your commute

Building Information for 16 May Street

Stories3Year Built1925Building Size-Lot Size0.27 AC / 11,761 SF

Payment Calculator

$9,209 per month

30 year fixed, 6.28% Interest

Principal and Interest

$7,881

Property Taxes

$1,328

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 16 May Street

Summary
Location and General Information
  • Country: US
  • Directions: From the Francis and Mary Usina Bridge follow the road until it turns into May Street then turn right at 16 May Street.
  • Zoning Description: Residential
  • MLS Area Major: 321-North City-St Augustine
  • City: St. Augustine
  • State: FL
  • Postal Code: 32084
  • County: St. Johns
  • Latitude: 29.910081
  • Longitude: -81.31799
  • MLS Area Minor: 321-North City-St Augustine
  • General Property Information: Waterfront YN: No
  • General Property Information: Senior Community YN: No
  • General Property Information: Accessibility Features YN: No
Taxes and HOA Information
  • Parcel Number: 1540600000
  • Association Fee: $.00
  • Association YN: No
  • General Property Information: CDD Fee YN: No
  • General Property Information: Association YN: No
Parking
  • Carport Spaces: 1
  • Carport YN: true
  • Garage Spaces: 2
  • Garage YN: Yes
  • Parking Features: Additional Parking, Attached Carport, Carport, Covered, Detached, Garage, Off Street
  • Attached Garage: No
  • General Property Information: Garage YN: Yes
  • General Property Information: Garage Spaces: 2.0
  • General Property Information: Carport YN: Yes
  • General Property Information: Carport Spaces: 1.0
  • Parking Features: Additional Parking: Yes
  • Parking Features: Attached Carport: Yes
  • Parking Features: Carport: Yes
  • Parking Features: Covered: Yes
  • Parking Features: Detached: Yes
  • Parking Features: Garage: Yes
  • Parking Features: Off Street: Yes
Property
Lot Information
  • Building Area Total: 4941.0
  • Living Area Source: Assessor
  • Lot Size Acres: 0.27
  • Living Area: 4495.0
  • Lot Size Area: 0.27
  • Lot Size Units: Acres
  • Lot Size Square Feet: 11761.2
Property and Assessments
  • Current Use: Investment, Residential, Single Family
  • New Construction YN: No
  • Property Attached YN: No
  • Year Built: 1925
  • MLS Approval Status: Yes
  • Room Total: 0.0
  • General Property Information: Lot Size Acres: 0.27
  • General Property Information: Bathrooms Half: 1.0
  • General Property Information: Living Area: 4495.0
  • General Property Information: Living Area Source: Assessor
  • General Property Information: Building Area Total: 4941.0
  • General Property Information: Accessory Dwelling Unit Y/N: Yes
  • General Property Information: New Construction YN: No
  • General Property Information: List Price/SqFt: 354.84
Utilities
  • Water Source: Public
  • Utilities: Cable Connected: Yes
  • Utilities: Electricity Connected: Yes
  • Utilities: Sewer Connected: Yes
  • Utilities: Water Connected: Yes
  • Water Source: Public: Yes
Interior and Exterior Features
Exterior Features
  • Electric: True
  • Architectural Style: Historic: Yes
  • Accessory Dwelling Information: Dwelling Type: Other
  • Accessory Dwelling Information: ADU Attached Y/N: Yes
  • Accessory Dwelling Information: Bathrooms: 1.0
  • Accessory Dwelling Information: Bedrooms: 1.0
Interior Features
  • Entry Level: 1.0
  • Stories: 3
  • Cooling: Central Air, Electric, Multi Units
  • Fireplaces Total: 1
  • Furnished: Furnished
  • Interior Features: Ceiling Fan(s), Eat-in Kitchen, Guest Suite, His and Hers Closets, In-Law Floorplan, Kitchen Island, Primary Bathroom - Tub with Shower, Vaulted Ceiling(s), Wet Bar
  • Levels: Three Or More
  • Heating: Central, Electric, Heat Pump
  • Flooring: Carpet, Laminate, Tile
  • Bathrooms Total (Integer): 5
  • Bathrooms Total (Decimal): 4.5
  • Bathrooms Total (Notational): 4.1
  • Cooling: Yes
  • Heating: Yes
  • Fireplace Y N: Yes
  • General Property Information: Furnished: Furnished
  • General Property Information: Stories: 3.0
  • Appliances: Convection Oven: Yes
  • Appliances: Dishwasher: Yes
  • Appliances: Disposal: Yes
  • Appliances: Dryer: Yes
  • Appliances: Electric Cooktop: Yes
  • Appliances: Electric Oven: Yes
  • Appliances: Electric Range: Yes
  • Appliances: Electric Water Heater: Yes
  • Appliances: Freezer: Yes
  • Appliances: Ice Maker: Yes
  • Appliances: Microwave: Yes
  • Appliances: Refrigerator: Yes
  • Appliances: Washer: Yes
  • Cooling: Central Air: Yes
  • Cooling: Electric: Yes
  • Fireplace Features: Fireplaces Total: 1.0
  • Flooring: Carpet: Yes
  • Flooring: Laminate: Yes
  • Flooring: Tile: Yes
  • Heating: Central: Yes
  • Heating: Electric: Yes
  • Heating: Heat Pump: Yes
  • Levels: Three Or More: Yes
  • Interior Features: Ceiling Fan(s): Yes
  • Interior Features: Eat-in Kitchen: Yes
  • Interior Features: Guest Suite: Yes
  • Interior Features: His and Hers Closets: Yes
  • Interior Features: In-Law Floorplan: Yes
  • Interior Features: Kitchen Island: Yes
  • Interior Features: Primary Bathroom - Tub with Shower: Yes
  • Interior Features: Vaulted Ceiling(s): Yes
  • Interior Features: Wet Bar: Yes
Agent
Sale and Listings
  • General Property Information: Entry Level: 1.0
Showing and Remarks
  • Public Remarks: 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
  • General Property Information: Directions: From the Francis and Mary Usina Bridge follow the road until it turns into May Street then turn right at 16 May Street.
  • General Property Information: Public Remarks: 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
Rental
Rental Information
  • Utilities: Cable Connected, Electricity Connected, Sewer Connected, Water Connected
  • Rental Restrictions: 1 Week: Yes

Property History for 16 May Street

DateEvent & SourcePriceAppreciation
Nov 12, 2025

Listed (Active)

NEFMLS #2087301

$1,695,000
Nov 11, 2025

Expired

NEFMLS #2087301

$1,595,000
Jul 14, 2025

Price Change

NEFMLS #2087301

$1,645,000
May 12, 2025

Listed (Active)

NEFMLS #2087301

$1,695,000
Dec 18, 2023

Sold

SASJMLS #237231

$900,000
Dec 17, 2023

Sold

NEFMLS #1257836

$900,000
Dec 14, 2023

Sold (Public Record)

Public Record #1524621480

$900,000
Dec 14, 2023

Sold (Public Record)

Public Record #1524621480

$900,000

+2.4% / yr

Nov 16, 2023

Listed (Active)

SASJMLS #237231

$1,399,000
Nov 15, 2023

Listed (Active)

NEFMLS #1257836

$1,399,000
Jul 1, 2021

Sold (Public Record)

Public Record #1466393859

$850,000

+0.8% / yr

Jun 30, 2021

Sold

NEFMLS #1101613

$850,000
May 19, 2021

Pending

NEFMLS #1101613

Mar 25, 2021

Listed (Active)

NEFMLS #1101613

$880,000
Jan 10, 2020

Expired

SASJMLS #185732

Jan 10, 2020

Sold

SASJMLS #185732

$729,900
Jan 10, 2020

Expired

SASJMLS #185732

Jan 8, 2020

Expired

NEFMLS #979944

$729,900
Jul 3, 2019

Price Change

SASJMLS #185732

$750,000
Feb 21, 2019

Listed (Active)

NEFMLS #979944

$765,000
Feb 16, 2019

Listed (Active)

SASJMLS #185732

$765,000
Jan 4, 2019

Withdrawn

SASJMLS #159769

Jan 4, 2019

Sold

SASJMLS #159769

$765,000
Jan 4, 2019

Withdrawn

SASJMLS #159769

Dec 31, 2018

Expired

NEFMLS #802433

Nov 20, 2015

Listed (Active)

NEFMLS #802433

$869,000
Nov 12, 2015

Listed (Active)

SASJMLS #159769

$869,000
Mar 5, 2014

Sold

NEFMLS #668338

$800,000
Mar 5, 2014

Sold (Public Record)

Public Record #411787209

$800,000
Mar 5, 2014

Sold

SASJMLS #144958

$800,000
Feb 16, 2014

Pending

NEFMLS #668338

Feb 14, 2014

Pending

SASJMLS #144958

Jan 22, 2014

Listed (Active)

NEFMLS #668338

$825,000
Jun 2, 2013

Listed (Active)

SASJMLS #144958

$825,000
May 30, 2013

Expired

NEFMLS #644824

$998,000
May 19, 2013

Withdrawn

SASJMLS #139951

May 19, 2013

Sold

SASJMLS #139951

$998,000
May 19, 2013

Withdrawn

SASJMLS #139951

Nov 28, 2012

Listed (Active)

NEFMLS #644824

$998,000
Nov 27, 2012

Listed (Active)

SASJMLS #139951

$998,000
Oct 13, 2012

Expired

SASJMLS #136711

Oct 12, 2012

Sold

SASJMLS #136711

$1,054,000
May 12, 2012

Listed (Active)

SASJMLS #136711

$1,054,000
DateEvent & SourcePrice
11/12/2025

Listed (Active)

NEFMLS #2087301

$1,695,000
11/11/2025

Expired

NEFMLS #2087301

$1,595,000
07/14/2025

Price Change

NEFMLS #2087301

$1,645,000
05/12/2025

Listed (Active)

NEFMLS #2087301

$1,695,000
12/18/2023

Sold

SASJMLS #237231

$900,000
12/17/2023

Sold

NEFMLS #1257836

$900,000
12/14/2023

Sold (Public Record)

Public Record #1524621480

$900,000
12/14/2023

Sold (Public Record)

Public Record #1524621480

$900,000

+2.4% / yr

11/16/2023

Listed (Active)

SASJMLS #237231

$1,399,000
11/15/2023

Listed (Active)

NEFMLS #1257836

$1,399,000
07/01/2021

Sold (Public Record)

Public Record #1466393859

$850,000

+0.8% / yr

06/30/2021

Sold

NEFMLS #1101613

$850,000
05/19/2021

Pending

NEFMLS #1101613

03/25/2021

Listed (Active)

NEFMLS #1101613

$880,000
01/10/2020

Expired

SASJMLS #185732

01/10/2020

Sold

SASJMLS #185732

$729,900
01/10/2020

Expired

SASJMLS #185732

01/08/2020

Expired

NEFMLS #979944

$729,900
07/03/2019

Price Change

SASJMLS #185732

$750,000
02/21/2019

Listed (Active)

NEFMLS #979944

$765,000
02/16/2019

Listed (Active)

SASJMLS #185732

$765,000
01/04/2019

Withdrawn

SASJMLS #159769

01/04/2019

Sold

SASJMLS #159769

$765,000
01/04/2019

Withdrawn

SASJMLS #159769

12/31/2018

Expired

NEFMLS #802433

11/20/2015

Listed (Active)

NEFMLS #802433

$869,000
11/12/2015

Listed (Active)

SASJMLS #159769

$869,000
03/05/2014

Sold

NEFMLS #668338

$800,000
03/05/2014

Sold (Public Record)

Public Record #411787209

$800,000
03/05/2014

Sold

SASJMLS #144958

$800,000
02/16/2014

Pending

NEFMLS #668338

02/14/2014

Pending

SASJMLS #144958

01/22/2014

Listed (Active)

NEFMLS #668338

$825,000
06/02/2013

Listed (Active)

SASJMLS #144958

$825,000
05/30/2013

Expired

NEFMLS #644824

$998,000
05/19/2013

Withdrawn

SASJMLS #139951

05/19/2013

Sold

SASJMLS #139951

$998,000
05/19/2013

Withdrawn

SASJMLS #139951

11/28/2012

Listed (Active)

NEFMLS #644824

$998,000
11/27/2012

Listed (Active)

SASJMLS #139951

$998,000
10/13/2012

Expired

SASJMLS #136711

10/12/2012

Sold

SASJMLS #136711

$1,054,000
05/12/2012

Listed (Active)

SASJMLS #136711

$1,054,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 16 May Street

Taxable ValueLand-Additions-Total-
Tax Record2024$15,932 ($1,328 / month)
Home Facts
Beds4Total Finished SqFt4,495 SqFtAbove Grade Finished SqFt4,495 SqFtStories3Lot Size12,197 SqFtStyleSingle Family ResidenceYear Built1925Year Renovated1995CountyST. JOHNSAPN154060 0000Fireplace TypeHas Fireplace

Schools near 16 May Street

This home is within St. Johns.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 6 to 8
Public - 9 to 12
Charter - K to 6
Rating
School
Distance
Ketterlinus Elementary School
PublicPK to 5

Sebastian Middle School
Public6 to 8

St. Augustine High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

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16 May Street is a single family home for sale in St. Augustine, FL 32084. This property was listed for sale on May 13, 2025 by COLDWELL BANKER ANABASIS REALTY, it's currently listed at $1,595,000. It has been on the market for a total of 236 days and was last sold on December 18, 2023. This listing's school district is St. Johns. Nearby schools include Ketterlinus Elementary School, Sebastian Middle School and St. Augustine High School. 16 May Street is a 4-bed, 5-bath, 4,495 sqft single family home built in 1925.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of COLDWELL BANKER ANABASIS REALTY

Based on information from one of the following Multiple Listing Services: Pensacola Association of REALTORS®, Amelia Island Nassau County Association of REALTORS and NEFMLS. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Pensacola Association of REALTORS®, Amelia Island Nassau County Association of REALTORS and NEFMLS is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.