Nestled on 2 acres in the heart of San Mateo, Florida, Historic Victorian ''Painted Lady'' at 150 Central Avenue-formerly known as Fern Court Bed and Breakfast- offers a rare opportunity to own a piece of local history. Built in the early 20th century by Henry B. Bailey (a railroad magnate and citrus broker), this stately home helped shape the very foundation of San Mateo. Bailey's influence persuaded Henry Flagler to extend the Florida East Coast Railway through the area, marking Fern Court as both a residence and a legacy. The home was once a vibrant social hub and entertained many traveling into the area on the San Mateo Express. In 1905, it even welcomed Mrs. Theodore Roosevelt for a stay. Though time has weathered parts of the home, much of its historic character remains beautifully intact. With 4624 square feet including 7 Bedrooms, and 9 baths and a hidden room- it hosts a unique opportunity to breathe new life into the halls and to own a piece of Florida's Gilded Age.
Closed
$399,000
150 CENTRAL Avenue, San Mateo, FL 32187
7beds
4,624sqft
Single Family Residence
Built in 1889
2 Acres Lot
$405,100 Zestimate®
$86/sqft
$3,819 Estimated rent
Home value
$405,100
$320,000 - $514,000
$3,819/mo
Zestimate® history
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What's special
Zillow last checked: 8 hours ago
Listing updated: August 15, 2025 at 01:16pm
Listed by:
AMIRA HIGGINBOTHAM 904-315-3175,
IHEART REALTY INC 386-546-8571,
CHRIS FIELDS 386-916-5002
Bought with:
AMIRA HIGGINBOTHAM, 3602378
IHEART REALTY INC
CHRIS FIELDS, BK 3087305
Source: realMLS,MLS#: 2091604
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 7
- Bathrooms: 9
- Full bathrooms: 6
- 1/2 bathrooms: 3
Heating
- Central
Cooling
- Central Air, Wall/Window Unit(s)
Appliances
- Included: Dishwasher, Gas Oven, Gas Range, Gas Water Heater
- Laundry: Electric Dryer Hookup, Washer Hookup
Features
- Built-in Features, Entrance Foyer, Kitchen Island, Other
- Flooring: Carpet, Laminate, Tile, Wood
- Number of fireplaces: 4
- Fireplace features: Wood Burning
Interior area
- Total interior livable area: 4,624 sqft
Property
Parking
- Total spaces: 2
- Parking features: Detached, Garage, RV Access/Parking
- Garage spaces: 2
Accessibility
- Accessibility features: Accessible Approach with Ramp
Features
- Levels: Three Or More
- Stories: 3
- Patio & porch: Covered, Front Porch, Rear Porch, Screened, Side Porch, Wrap Around
- Fencing: Wood
- Has view: Yes
- View description: Trees/Woods
Lot
- Size: 2 Acres
- Features: Agricultural, Cleared, Corner Lot, Few Trees
Details
- Additional structures: Shed(s)
- Parcel number: 281027000003110000
- Zoning description: Agricultural
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Victorian
- Property subtype: Single Family Residence
Materials
- Frame, Wood Siding
- Roof: Metal
Condition
- New construction: No
- Year built: 1889
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Cable Available, Electricity Connected, Natural Gas Connected, Water Connected
Community & neighborhood
Security
- Security features: Smoke Detector(s)
Location
- Region: San Mateo
- Subdivision: Metes & Bounds
Other
Other facts
- Listing terms: Cash,Conventional
- Road surface type: Asphalt
Price history
| Date | Event | Price |
|---|---|---|
| 8/15/2025 | Sold | $399,000$86/sqft |
Source:  realMLS #2091604 | ||
| 6/5/2025 | Listed for sale | $399,000+82.2%$86/sqft |
Source: realMLS #2091604 | ||
| 9/6/2016 | Sold | $219,000-4.7%$47/sqft |
Source: realMLS #840217 | ||
| 8/18/2016 | Pending sale | $229,900$50/sqft |
Source: Watson Realty Corp. #840217 | ||
| 7/29/2016 | Listed for sale | $229,900-17.9%$50/sqft |
Source: WATSON REALTY CORP #840217 | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $7,506 +8.1% | $498,390 +7.8% |
| 2023 | $6,944 +15.8% | $462,370 +19.7% |
| 2022 | $5,997 +11.5% | $386,270 +24.2% |
Find assessor info on the county website
Neighborhood: 32187
Nearby schools
GreatSchools rating
- 4/10Browning-Pearce Elementary SchoolGrades: K-6Distance: 0.5 mi
- 3/10Palatka High SchoolGrades: 7-12Distance: 5.9 mi
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