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.
Sold for $449,000
Zillow last checked:
Listing updated:
Bought with:
Joseph Parsons, 3623260
The Naumann Group Real Estate
Source: TBR,MLS#: 381694
Price history
| Date | Event | Price |
|---|---|---|
| 4/30/2025 | Sold | $449,000$124/sqft |
Source:  TBR #381694 Report a problem | ||
| 3/31/2025 | Contingent | $449,000$124/sqft |
Source: TBR #381694 Report a problem | ||
| 2/7/2025 | Listed for sale | $449,000-5.5%$124/sqft |
Source: TBR #381694 Report a problem | ||
| 2/21/2024 | Listing removed | -- |
Source: TBR #367716 Report a problem | ||
| 2/5/2024 | Contingent | $474,900$131/sqft |
Source: TBR #367716 Report a problem | ||
| 1/23/2024 | Listed for sale | $474,900-13.6%$131/sqft |
Source: TBR #367716 Report a problem | ||
| 7/17/2023 | Listing removed | -- |
Source: TBR #359631 Report a problem | ||
| 7/11/2023 | Listed for sale | $549,900$151/sqft |
Source: TBR #359631 Report a problem | ||
| 6/27/2023 | Contingent | $549,900$151/sqft |
Source: TBR #359631 Report a problem | ||
| 4/29/2023 | Listed for sale | $549,900+83.9%$151/sqft |
Source: TBR #358163 Report a problem | ||
| 1/6/2020 | Sold | $299,000-9.1%$82/sqft |
Source: TBR #291254 Report a problem | ||
| 12/6/2019 | Pending sale | $329,000$91/sqft |
Source: Kelly & Kelly Properties, Inc #291254 Report a problem | ||
| 8/13/2019 | Price change | $329,000-5.7%$91/sqft |
Source: Kelly & Kelly Properties, Inc #291254 Report a problem | ||
| 2/1/2019 | Price change | $349,000-4.6%$96/sqft |
Source: Kelly & Kelly Properties, Inc #291254 Report a problem | ||
| 12/22/2018 | Listed for sale | $365,900$101/sqft |
Source: Kelly & Kelly Properties, Inc #291254 Report a problem | ||
| 11/17/2018 | Pending sale | $365,900$101/sqft |
Source: Kelly & Kelly Properties, Inc #291254 Report a problem | ||
| 10/19/2018 | Price change | $365,900-1.1%$101/sqft |
Source: Kelly & Kelly Properties, Inc #291254 Report a problem | ||
| 10/13/2018 | Price change | $369,900-1.4%$102/sqft |
Source: Kelly & Kelly Properties, Inc #291254 Report a problem | ||
| 3/19/2018 | Listed for sale | $375,000+7.1%$103/sqft |
Source: Kelly & Kelly Properties, Inc #291254 Report a problem | ||
| 3/10/2016 | Sold | $350,000$96/sqft |
Source: TBR #263150 Report a problem | ||
| 12/29/2015 | Pending sale | $350,000$96/sqft |
Source: United Country Report a problem | ||
| 11/5/2015 | Listed for sale | $350,000+112.1%$96/sqft |
Source: United Country Southern AgLand #263150 Report a problem | ||
| 12/6/2007 | Sold | $165,000$45/sqft |
Source: Public Record Report a problem | ||
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