Seller's Agent in 2025
Sandy Ferrera
All County Suncoast Property
(727) 541-2578
12 Total Sales
Estimated Value: $468,000 - $516,000
Step into the timeless elegance of the Simpkins-Bailey House, a distinguished circa 1854 residence nestled in the heart of Monticello's Historic District. This 3-bedroom, 3.5-bathroom home offers 3,635 square feet of meticulously updated living space, seamlessly blending historic charm with modern comforts. Zoned for business-residential use, the property provides incredible flexibility for a private residence, office, or mixed-use opportunity. The home features a brand-new 2024 metal roof and an encapsulated crawlspace with a dehumidifier for enhanced preservation. Inside, beautifully wide-plank hardwood floors stretch throughout, with a fireplace in every room adding to the historic character. The renovated kitchen and bathrooms seamlessly integrate modern style while honoring the home’s rich history, including a stunning clawfoot tub in the master bath. French doors lead from the living space to a screened-in back porch, offering a perfect place to relax. The fully fenced backyard features a picturesque boxwood garden, a charming pergola, and a magnificent live oak, creating a private oasis just steps from the vibrant downtown circle. With its stately presence, prime location, and thoughtful updates, this is a rare opportunity to own a beautifully preserved piece of Monticello’s history.
Last Agent to Sell the Property
All County Suncoast Property License #539781 Listed on: 02/07/2025
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Buyer | Sale Price | Title Company |
|---|---|---|---|
| $449,000 | North Florida Abstract & Title | ||
| $100 | Mcpherson Scott W | ||
| $299,000 | North Florida Abstract & Ttl | ||
| $100 | North Florida Abstract & Title | ||
| $350,000 | North Fl Abstract & Title Co | ||
| $165,000 | North Fl Abstract & Title Co |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Borrower | Loan Amount |
|---|---|---|---|
| Closed | $426,550 | ||
| Closed | $274,000 | ||
| Closed | $69,000 | ||
| Closed | $60,000 | ||
| Closed | $30,000 |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 04/30/2025 04/30/25 | Sold | $449,000 | 0.0% | $124 / Sq Ft | |
| 02/07/2025 02/07/25 | For Sale | $449,000 | +50.2% | $124 / Sq Ft | |
| 01/06/2020 01/06/20 | Sold | $299,000 | -9.1% | $82 / Sq Ft | View Prior Sale |
| 12/17/2019 12/17/19 | Pending | -- | -- | -- | |
| 08/13/2019 08/13/19 | Price Changed | $329,000 | -5.7% | $91 / Sq Ft | |
| 05/01/2019 05/01/19 | For Sale | $349,000 | +16.7% | $96 / Sq Ft | |
| 05/01/2019 05/01/19 | Off Market | $299,000 | -- | -- | |
| 02/01/2019 02/01/19 | Price Changed | $349,000 | -4.6% | $96 / Sq Ft | |
| 10/19/2018 10/19/18 | Price Changed | $365,900 | -1.1% | $101 / Sq Ft | |
| 10/13/2018 10/13/18 | Price Changed | $369,900 | -1.4% | $102 / Sq Ft | |
| 03/19/2018 03/19/18 | For Sale | $375,000 | +7.1% | $103 / Sq Ft | |
| 03/10/2016 03/10/16 | Sold | $350,000 | 0.0% | $96 / Sq Ft | View Prior Sale |
| 03/01/2016 03/01/16 | Pending | -- | -- | -- | |
| 11/04/2015 11/04/15 | For Sale | $350,000 | -- | $96 / Sq Ft |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| 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 | $7,701 | $368,409 | $30,919 | $337,490 |
| 2024 | $7,778 | $366,044 | $27,975 | $338,069 |
| 2023 | $7,232 | $338,532 | $0 | $0 |
| 2022 | $6,819 | $355,894 | $23,558 | $332,336 |
| 2021 | $6,395 | $327,619 | $23,558 | $304,061 |
| 2020 | $5,673 | $254,386 | $23,558 | $230,828 |
| 2019 | $5,478 | $247,377 | $23,558 | $223,819 |
| 2018 | $5,455 | $243,901 | $22,380 | $221,521 |
| 2017 | $5,475 | $237,425 | $22,379 | $215,046 |
| 2016 | $3,492 | $149,541 | $0 | $0 |
| 2015 | -- | $151,313 | $0 | $0 |
| 2014 | -- | $153,084 | $0 | $0 |
Seller's Agent in 2025
Sandy Ferrera
All County Suncoast Property
(727) 541-2578
12 Total Sales
Buyer's Agent in 2025
Joseph Parsons
The Naumann Group Real Estate
(850) 597-1122
11 Total Sales
L
Buyer's Agent in 2020
LEO D. COUTTS
Marion H Riley Realty
L
Buyer's Agent in 2016
Larry Stokely
Frog Realty
Source: Capital Area Technology & REALTOR® Services (Tallahassee Board of REALTORS®)
MLS Number: 381694
APN: 00-00-00-0390-0000-0010
Ask me questions while you tour the home.