221 Kiley Drive, Monticello, FL 32344
Local realty services provided by:Better Homes and Gardens Real Estate Florida 1st
221 Kiley Drive,Monticello, FL 32344
$1,325,000
- 5 Beds
- 5 Baths
- 5,476 sq. ft.
- Single family
- Active
Listed by: wilda sigler, chip williams
Office: keller williams town & country
MLS#:395876
Source:FL_TBR
Price summary
- Price:$1,325,000
- Price per sq. ft.:$241.96
About this home
Welcome to 221 Kiley Road in Monticello, Florida — a rare estate where vineyard charm, equestrian living, and exceptional space come together to create an unforgettable lifestyle. This 5-bedroom, 3.5-bathroom estate is a true masterpiece, gracefully set on 5 private acres and complemented by a beautiful pool house with an additional bathroom. An additional adjoining 5-acre parcel is also available, offering the rare opportunity to expand your privacy, create a multi-generational compound, or enhance the estate even further. Set on picturesque rolling land, this one-of-a-kind property features your own private vineyard, offering a breathtaking and romantic backdrop for everyday living and entertaining. Imagine sunset dinners overlooking the vines, peaceful morning walks through the rows, or simply enjoying the beauty and serenity that only a setting like this can provide. Equestrian enthusiasts will appreciate the well-appointed horse stable, open pasture, and room to ride, creating the perfect environment for both horses and riders to thrive. Thoughtfully designed for function and beauty, the grounds invite you to embrace true North Florida country living. At the heart of the property sits an impressive residence offering approximately 5,500 square feet of living space, ideal for large households, multi-generational living, or those who love to entertain. The thoughtfully designed layout features expansive living areas filled with natural light, a spacious kitchen with abundant cabinetry and workspace, and oversized bedrooms that serve as peaceful private retreats. Multiple flex spaces provide endless possibilities for home offices, media rooms, fitness areas, hobby spaces, or additional guest accommodations — tailored to fit your lifestyle. Step outside to your private pool oasis, perfect for relaxing afternoons or hosting unforgettable gatherings. A separate guest house offers comfortable accommodations for visitors, extended family, or a private retreat, adding flexibility and value to this exceptional estate. From vineyard evenings and horseback mornings to poolside afternoons, 221 Kiley Road is more than a home — it’s a lifestyle. Offering space, versatility, natural beauty, and privacy while still convenient to downtown Monticello, schools, shopping, and dining, this is a truly rare opportunity to own a remarkable property where memories are made for generations.
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Home facts
- Year built:2009
- Listing ID #:395876
- Added:5 day(s) ago
- Updated:February 10, 2026 at 04:34 PM
Rooms and interior
- Bedrooms:5
- Total bathrooms:5
- Full bathrooms:4
- Half bathrooms:1
- Living area:5,476 sq. ft.
Heating and cooling
- Cooling:Ceiling Fans, Central Air, Electric
- Heating:Central, Fireplaces
Structure and exterior
- Year built:2009
- Building area:5,476 sq. ft.
- Lot area:5 Acres
Schools
- High school:Jefferson County K-12 School
- Middle school:Jefferson County K-12 School
- Elementary school:Jefferson County K-12 School
Utilities
- Sewer:Septic Tank
Finances and disclosures
- Price:$1,325,000
- Price per sq. ft.:$241.96
- Tax amount:$8,073
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