Seller's Agent in 2025
Sandy Ferrera
All County Suncoast Property
(727) 541-2578
1 in this area
11 Total Sales
Estimated Value: $466,000 - $527,000
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.
| Date | Buyer | Sale Price | Title Company |
|---|---|---|---|
| Parsons Lucas | $449,000 | North Florida Abstract & Title | |
| Parsons Lucas | $449,000 | North Florida Abstract & Title | |
| Mcpherson Scott W | $100 | Mcpherson Scott W | |
| Simpkins House Llc | $100 | North Florida Abstract & Title | |
| Simpkins House Llc | $100 | North Florida Abstract & Title | |
| Mcpherson Scott | $299,000 | North Florida Abstract & Ttl | |
| Wofford Nathaniel L | $350,000 | North Fl Abstract & Title Co | |
| Kirkpatrick William H | $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 |
|---|---|---|---|
| Open | Parsons Lucas | $426,550 | |
| Closed | Parsons Lucas | $426,550 | |
| Previous Owner | Mcpherson Scott | $274,000 |
| 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 |
| 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
1 in this area
11 Total Sales
Buyer's Agent in 2025
Joseph Parsons
The Naumann Group Real Estate
(850) 597-1122
1 in this area
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
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