16 MAY Street, St. Augustine, FL 32084

New Listing

$1,695,000

Virtual Tour

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

Property Type: Residential Bedrooms: 4 Baths: 5 Square Footage: 4,941 Lot Size (sq. ft.): 11,761 Status: Active

Current Price: $1,695,000 List Date: 5/13/2025 Last Modified: 5/14/2025

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

Supplements: 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.

Open Houses

Friday, May 30, 3:30 pm - 6:30 pm

Saturday, May 31, 11:00 am - 2:00 pm

Sunday, June 01, 1:00 pm - 4:00 pm

More Information MLS# 2087301

Contract Information

Current Price: $1,695,000 Property Sub Type: Single Family Residence Property Attached YN: No Status: Active List Price: $1,695,000 Listing Contract Date: 2025-05-12

Location Tax and Legal

Street Number: 16 Street Name: MAY Street Suffix: Street County: St. Johns State: FL Postal Code: 32084 MLS Area Major: 321-North City-St Augustine Subdivision Name: Nelmar Terrace

General Property Information

Bedrooms Total: 4 Bathrooms Full: 4 Bathrooms Half: 1 Bathrooms Total: 5 Living Area: 4495 Living Area Source: Assessor Building Area Total: 4941 Year Built: 1925 Accessory Dwelling Unit Y/N: Yes Homestead YN: No Lot Size Acres: 0.27 Association YN: No CDD Fee YN: No Accessibility Features YN: No New Construction YN: No Garage YN: Yes Garage Spaces: 2 Carport YN: Yes Carport Spaces: 1 Pool Private YN: No Water Body Access YN: No Waterfront YN: No Furnished: Furnished Stories: 3 Entry Level: 1 Senior Community YN: No Directions: From the Francis and Mary Usina Bridge follow the road until it turns into May Street then turn right at 16 May Street. 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 List Price/SqFt: 377.09

Status Change Information

Major Change Timestamp: 2025-05-13T17:51:40Z Major Change Type: New Listing

Accessory Dwelling Information

Dwelling Type: Other ADU Attached Y/N: Yes Bathrooms: 1 Bedrooms: 1

Fireplace Features

Fireplaces Total: 1

DPR Eligible

DPR Eligible: No

Property Features

Architectural Style: Historic Levels: Three Or More Property Condition: Updated/Remodeled Rental Restrictions: 1 Week Appliances: Convection Oven; Dishwasher; Disposal; Dryer; Electric Cooktop; Electric Oven; Electric Range; Electric Water Heater; Freezer; Ice Maker; Microwave; Refrigerator; Washer 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 Utilities: Cable Connected; Electricity Connected; Sewer Connected; Water Connected Cooling: Central Air; Electric; Multi Units Heating: Central; Electric; Heat Pump Water Source: Public Parking Features: Additional Parking; Attached Carport; Carport; Covered; Detached; Garage; Off Street Current Use: Investment; Residential; Single Family Possession: Close Of Escrow Listing Terms: Cash; Conventional

Documents

Furniture/Asset List ›

Sellers Property Disclosure ›

LBP Disclosure ›

Listing Office: COLDWELL BANKER ANABASIS REALTY

Last Updated: May - 14 - 2025

Information deemed reliable but not guaranteed.