Estimated payment $9,685/month
Total Views
17,622
4
Beds
4.5
Baths
4,495
Sq Ft
$355
Price per Sq Ft
Highlights
- Hot Property
- Vaulted Ceiling
- Furnished
- Ketterlinus Elementary School Rated A
- 1 Fireplace
- 3-minute walk to Davenport Park
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 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 can stay! 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.
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $15,932
Year Built
- Built in 1925 | Remodeled
Lot Details
- 0.27 Acre Lot
- Historic Home
Parking
- 2 Car Detached Garage
- 1 Attached Carport Space
- Additional Parking
- Off-Street Parking
Home Design
- Entry on the 1st floor
Interior Spaces
- 4,495 Sq Ft Home
- 3-Story Property
- Wet Bar
- Furnished
- Vaulted Ceiling
- Ceiling Fan
- 1 Fireplace
Kitchen
- Eat-In Kitchen
- Convection Oven
- Electric Oven
- Electric Cooktop
- Microwave
- Freezer
- Ice Maker
- Dishwasher
- Kitchen Island
- Disposal
Flooring
- Carpet
- Laminate
- Tile
Bedrooms and Bathrooms
- 4 Bedrooms
- Dual Closets
- In-Law or Guest Suite
- Bathtub and Shower Combination in Primary Bathroom
Laundry
- Dryer
- Washer
Additional Homes
- Accessory Dwelling Unit (ADU)
Utilities
- Multiple cooling system units
- Central Heating and Cooling System
- Heat Pump System
- Electric Water Heater
Community Details
- No Home Owners Association
- Nelmar Terrace Subdivision
Listing and Financial Details
- Assessor Parcel Number 1540600000
Map
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Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $17,475 | $848,266 | $250,800 | $597,466 |
| 2024 | $17,475 | $832,460 | $250,800 | $581,660 |
| 2023 | $17,475 | $907,489 | $334,400 | $573,089 |
| 2022 | $16,942 | $876,484 | $262,170 | $614,314 |
| 2021 | $13,714 | $693,203 | $0 | $0 |
| 2020 | $14,576 | $731,872 | $0 | $0 |
| 2019 | $13,311 | $690,790 | $0 | $0 |
| 2018 | $13,848 | $671,889 | $0 | $0 |
| 2017 | $13,949 | $669,853 | $91,960 | $577,893 |
| 2016 | $14,313 | $669,853 | $0 | $0 |
| 2015 | $13,923 | $677,278 | $0 | $0 |
| 2014 | $6,259 | $381,702 | $0 | $0 |
Source: Public Records
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 10/07/2025 10/07/25 | Price Changed | $1,595,000 | 0.0% | $355 / Sq Ft | |
| 10/07/2025 10/07/25 | For Sale | $1,595,000 | -3.0% | $355 / Sq Ft | |
| 09/11/2025 09/11/25 | Off Market | $1,645,000 | -- | -- | |
| 07/14/2025 07/14/25 | Price Changed | $1,645,000 | -2.9% | $366 / Sq Ft | |
| 05/13/2025 05/13/25 | For Sale | $1,695,000 | +88.3% | $377 / Sq Ft | |
| 12/18/2023 12/18/23 | Sold | $900,000 | +12.5% | $171 / Sq Ft | View Prior Sale |
| 12/17/2023 12/17/23 | Off Market | $800,000 | -- | -- | |
| 12/17/2023 12/17/23 | Off Market | $850,000 | -- | -- | |
| 12/16/2023 12/16/23 | Off Market | $1,399,000 | -- | -- | |
| 11/17/2023 11/17/23 | For Sale | $1,399,000 | +64.6% | $265 / Sq Ft | |
| 07/01/2021 07/01/21 | Sold | $850,000 | -3.4% | $172 / Sq Ft | View Prior Sale |
| 05/19/2021 05/19/21 | Pending | -- | -- | -- | |
| 03/26/2021 03/26/21 | For Sale | $880,000 | +10.0% | $178 / Sq Ft | |
| 03/06/2014 03/06/14 | Sold | $800,000 | -3.0% | $142 / Sq Ft | View Prior Sale |
| 02/14/2014 02/14/14 | Pending | -- | -- | -- | |
| 01/23/2014 01/23/14 | For Sale | $825,000 | -- | $147 / Sq Ft |
Source: realMLS (Northeast Florida Multiple Listing Service)
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $900,000 | Landmark Title | |
| Warranty Deed | $900,000 | Landmark Title | |
| Warranty Deed | $850,000 | Landmark Title | |
| Interfamily Deed Transfer | -- | Attorney | |
| Warranty Deed | $800,000 | Attorney |
Source: Public Records
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $680,000 | New Conventional | |
| Previous Owner | $600,000 | Seller Take Back |
Source: Public Records
About the Listing Agent
Bryce Ocepek is the Broker and Co-Owner of Coldwell Banker Anabasis Realty. Bryce was awarded his real estate license at just 19 years old and worked for Berkshire Hathaway, Pineywoods Realty, and eventually EquityPro where he sold a combined $15 million dollars of investment real estate including over 100+ units worth of multifamily and 120+ units of self storage real estate all before the age of 23. Born in West Palm Beach and raised in Amelia Island, Bryce is a proud Florida native. Working
Bryce's Other Listings
Source: realMLS (Northeast Florida Multiple Listing Service)
MLS Number: 2087301
APN: 154060-0000
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by NEFMLS.
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