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16 May Street

St. Augustine, FL 32084

4 beds
5 baths
4,941 sqft
11,761 sqft lot
$343 per sqft
1925 build
– on site

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.

Listing courtesy of NEFMLS / COLDWELL BANKER ANABASIS REALTY

Last checked: Checking… • Last updated May 13, 2025 •

MLS# 2087301 —

The Building

Year Built:

1925
New Construction:

false
Development Status:

None
Architectural Style:

Historic
Entry Level:

1
Stories:

3
Levels:

Three Or More
Basement:

None
Foundation Details:

None
Building Features:

None
Building Name:

None
Building Area Total:

4941.0

Interior

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
Flooring:

Carpet, Laminate, Tile
Fireplaces Total:

1
Fireplace:

true

Room Dimensions

Living Area:

4495.0
Living Area Units:

None
Living Area Source:

Assessor

Financial & Terms

Possession:

Close Of Escrow

Location

Directions:

From the Francis and Mary Usina Bridge follow the road until it turns into May Street then turn right at 16 May Street.
Cross Street:

None
Latitude:

29.910081
Longitude:

-81.31799

The Property

Parcel Number:

1540600000
Property Type:

Residential
Property Condition:

Updated/Remodeled
Property Subtype:

Single Family Residence
Property Attached:

false
Zoning:

None
Zoning Description:

Residential
Lot Size Acres:

0.27
Lot Size SqFt:

11761.2
Lot Size Area:

0.27
Lot Size Units:

Acres
Current Use:

Investment, Residential, Single Family
Possible Use:

None
Topography:

None
Additional Parcels:

No
Additional Parcels Description:

None
Land Lease:

No

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Legal Description:

2-1 NELMAR TERRACE LOT 28 OR5877/1761
Tax Annual Amount:

15932.45

Beds

Bedrooms Total:

4

Baths

Total Baths:

4.5
Total Baths:

5
Full Baths:

4
Three Quarter Baths:

None
Half Baths:

1
Partial Baths:

None
Quarter Baths:

None

The Listing

Virtual Tour URL Branded:

None
Virtual Tour URL Unbranded:

https://www.zillow.com/view-imx/468ff4f3-269d-48ab-b405-702608d8fa20?initialViewType=pano&utm_source=dashboard

Heating & Cooling

Heating:

Central, Electric, Heat Pump
Heating:

true
Cooling:

true
Cooling:

Central Air, Electric, Multi Units

Utilities

Utilities:

Cable Connected, Electricity Connected, Sewer Connected, Water Connected
Water Source:

Public

Appliances

Appliances:

Convection Oven, Dishwasher, Disposal, Dryer, Electric Cooktop, Electric Oven, Electric Range, Electric Water Heater, Freezer, Ice Maker, Microwave, Refrigerator, Washer

Schools

Elementary School District:

None
Middle Or Junior School District:

None

The Community

Subdivision Name:

Nelmar Terrace
Senior Community:

false
Pool Private:

No
Waterfront:

false
Water Body Name:

None
Pets Allowed:

None
Association:

false

Parking

Garage:

true
Garage Spaces:

2.0
Attached Garage:

false
Carport:

true
Carport Spaces:

1.0
Parking Total:

None
Parking Features:

Additional Parking, Attached Carport, Carport, Covered, Detached, Garage, Off Street

Monthly cost estimate

Asking price

$1,695,000

Expense	Monthly cost
Mortgage	$9,076
Taxes	$1,327
Insurance	$466
Utilities	$262 See report
Total	$11,131/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Soundscore™

Provided by HowLoud

Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price	% Change
5/13/25 May 13, 2025	Listed / Active	NEFMLS	$1,695,000	111.9% (10.0% / YR)
12/18/23 Dec 18, 2023	Sold	NEFMLS
12/10/23 Dec 10, 2023	Sold Subject To Contingencies	NEFMLS

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This house located in Magnolia, St. Augustine, FL 32084 is currently for sale for $1,695,000. 16 May Street is a 4,941 square foot house with 4 beds and 5 baths that has been on Estately for 0 days. 16 May Street is in the Magnolia neighborhood of St. Augustine and has a WalkScore® of 64, making it somewhat walkable.

Listing Courtesy of: NEFMLS and COLDWELL BANKER ANABASIS REALTY.

Based on information from the NORTHEAST FLORIDA MLS 2025. All information provided is deemed reliable but is not guaranteed and should be independently verified. NEFMLS, Estately and their affiliates provide the MLS and all content therein “AS IS” and without any warranty, express or implied. The information included in this listing is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information on each listing is furnished by the owner and deemed reliable to the best of his/her knowledge, but should be verified by the purchaser. NEFMLS and Estately assume no responsibility for typographical errors, misprints or misinformation. This property is offered without respect to any protected classes in accordance with the law.