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221 Kiley Drive, 
Monticello, FL 32344

$1,599,000


5

Beds


5

Baths


5,476

Sq Ft


Single Family

Active

Listed by

Barbra Boutin

Engel & Volkers Tallahassee

386-623-2806

Last updated:

June 21, 2025, 01:17 PM

MLS#

385332

Source:

FL TBR

About This Home

221 Kiley Drive

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!

Home Facts

Single Family

5 Baths

5 Bedrooms

Built in 2009

Price Summary

1,599,000

$292 per Sq. Ft.

MLS #:

385332

Last Updated:

June 21, 2025, 01:17 PM

Added:

1 month(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

5

Full Bathrooms:

4

Interior

Living Area:

5,476 Sq. Ft.


Structure

Structure

Architectural Style:

Split-Level, Traditional

Building Area:

5,476 Sq. Ft.

Year Built:

2009


Lot

Lot Size (Sq. Ft):

653,400


Finances & Disclosures

Finances

Price:

$1,599,000

Price per Sq. Ft:

$292 per Sq. Ft.

Source:FL TBR
The information being provided by Tallahassee Board of Realtors is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2025 Tallahassee Board of Realtors All rights reserved.

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