221 Kiley Dr Monticello, FL 32344
Property details
About 221 Kiley Dr
Welcome to a rare and exquisite, turn-key, 15-acre modern luxury estate, where timeless elegance meets Southern charm. Custom built by Riley Palmer, this exclusive, gated property with soaring ceilings and interior doors, is nestled just minutes from Tallahassee, Florida's Capital City, and historic Thomasville, Georgia in Monticello-home to a storied opera house and chic dining options-and offers the perfect blend of privacy, prestige and proximity. Work, school and play from home with dedicated office space and connectivity powered by Conexon Connect, the leading optic fiber broadband solution! The heart of the estate is a grand Great House, designed for multi-generational, refined living and effortless entertaining. Elegant finishes, a formal dining, separate breakfast room, and a gourmet, eat-in chef's kitchen, create an inviting atmosphere for everything from intimate dinners to lavish gatherings and holiday hosting. Retreat to the luxurious, spa inspired primary owner's suite on the main level, where relaxation awaits in a serene soaking tub framed by a tranquil view of your micro-vineyards. Indulge in the spacious double-head shower, complete with an oversized bench designed for ultimate comfort and rejuvenation. A versatile Coach House with sink and electricity, offers ample space for horses, a workshop, or lawn equipment, plus a grassy paddock for pasturing, ideal for equestrian enthusiasts or hobbyists. Nearby, the Pool House doubles as a fully equipped guest house with full bath, kitchen and laundry, perfect for hosting weekend visitors, a rather permanent caretaker or guest, or providing a private owner art studio, jam canning, winery production or retreat. Plant in your green house, or enjoy multiple vineyards boasting white Scuppernong and red Muscadine grapes for annual Fall harvesting, or make fresh peach, orange, and fig jams, or pecan pie, from your robust fruit tree offerings. A bonus warehouse and second well are a short walk on the adjoining 5-acre parcel with a spectacular hill-top view! Roof (2022) offering luxury Belmont by CertainTeed with lifetime transferrable warranty. Extensive Notable Estate Features list available including Vivint touch screen security system with options for 24/7 monitoring & motion detection, Generac Generator, Elan sound system, laundry shoot from second floor to mudroom, guest wet bar, side-by-side stainless KitchenAid in gourmet kitchen, plus two half refrigerators, a full-size stainless dishwasher, plus a convenient additional half dishwasher, Viking Professional six-burner gas cooktop, substantial walk-in pantry & Brew Express built-in coffee maker! Schools: Jefferson County K-12 Charter, Turning Point Alternative School or Aucilla Christian Academy, or plenty of options for classroom style home schooling. Square feet includes 576 sqft. pool guest house. List price includes 15-acres (3-5 acre cleared parcels. Lots 15, 16 & 17 in Timber Trace. Buyer can sell adjoining parcels if preferred, no subdividing less than 5 acres). Total bathroom count is 4 full and one half bath (4.5). Room measurements approximate. Buyer to verify. Welcome home!
Highlights
Virtual tour
Summary
- Partial Bathrooms: 1
- Full Bathrooms: 4
- Appliances: Dryer, Dishwasher, Ice Maker, Microwave, Oven, Range, Refrigerator, Washer
- Flooring Type: Wood, Bamboo, Tile
- Interior: Wet Bar, Tray Ceiling(s), High Ceilings, Vaulted Ceiling(s), Central Vacuum, Pantry, Walk-In Closet(s)
- Fireplace: Gas
- Total Bedroom Count: 5
- Garage Space: 3 spaces
- Private Pool: Yes
- View: Park
- Architectural Style: SplitLevel, Traditional
- Heating: Central, Electric, Fireplace(s)
- Cooling: Central Air, Ceiling Fan(s), Electric
- List Price: $1,549,000
- Price/SqFt: $282
- HOA Amount: $150
- Annual Tax Amount: $8,049
- Tax Year: 2023
- Directions: Hwy 90 E. to Ashville Hwy, Right on Bassett Dairy Rd, Right on Kiley Dr., Home on left.
- Year Built: 2009
- Living Area: 5,476 SqFt
- Lot Size: 15 Acres
- MLS Number: 385332
- MLS Name: Tallahassee
- Office Name: Engel & Völkers Tallahassee
- Office Phone: (386) 623-2806
- Office Email: carrie.cason@evrealestate.com
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Last updated on: 7/24/2025, 3:45:34 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Price information
Property sales
Date | Event | Price |
---|---|---|
Oct 10, 2017 | Home Sold | $725,000 |
Jun 08, 2006 | Home Sold | $85,000 |
Mar 01, 2005 | Home Sold | $50,000 |
Tax history
Year | Assessment | Property Tax |
---|---|---|
2023 | $609,364 | $8,049 |
2022 | $628,058 | $8,145 |
2021 | $602,731 | $8,145 |
2019 | $580,817 | $7,986 |
2018 | $570,611 | $5,781 |
2017 | $413,866 | $5,781 |
History based on county public records data.
Nearby schools
3
Jefferson County Elementary a Somerset Charter School
Public Charter PK-5
6.3 mi
•50 David Rd
1
Greenville Elementary School
Public District PK-5
10.6 mi
•729 SW Overstreet Ave
4
Chaires Elementary School
Public District PK-5
21.0 mi
•4774 Chaires Cross Rd
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $39,175. The most common annual income of people living in Monticello, FL is less than $<35k. Typical family type is single, no kids. Typical level of education for residents in this area is post secondary degree.
Frequently asked questions
About 221 Kiley Dr
The listing price of 221 Kiley Dr property is $1,549,000.
The property 221 Kiley Dr is a house located in Monticello, Florida, 32344.
Active Listing: 221 Kiley Dr is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 221 Kiley Dr are: Jefferson County Elementary a Somerset Charter School (GreatSchools Rating 3/10), Greenville Elementary School (GreatSchools Rating 1/10), Chaires Elementary School (GreatSchools Rating 4/10), Madison Creative Arts Academy Inc (GreatSchools Rating 5/10), Madison County Central School (GreatSchools Rating 2/10), Montford Middle School (GreatSchools Rating 8/10), Jefferson County High a Somerset Charter School (GreatSchools Rating 4/10), Madison County High School (GreatSchools Rating 2/10), Delta Innovative School (GreatSchools Rating 2/10).
According to the records, the last property tax for 2023 is $8,049 (source: MLS/based on county public records data).
The last sale was on October 10, 2017 for $725,000 (source: MLS/tax record).
The property at 221 Kiley Dr has 5 bedrooms and 4 full and 1 half bathrooms.
The property 221 Kiley Dr is 5,476 SqFt (source: MLS/tax record).
The year of construction for 221 Kiley Dr is 2009.
This home is located at 221 Kiley Dr in Monticello, FL and zip code 32344. This 5,476 square foot home, which was built in 2009, sits on a 15.00 acre lot. Features: 5 bedrooms, 5 bathrooms. It has been listed on Rocket Homes since May 1, 2025 and is currently priced at $1,549,000.