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$1,549,000

221 Kiley Dr Monticello, FL 32344

5 beds
4 full, 1 partial
5,476 sqft
15.0 acres
$283 / sqft
House

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

Home typeSingle Family Residence
HeatingCentral, Electric, Fireplace(s)
StatusActive
CoolingCentral Air, Ceiling Fan(s), Electric
Size5,476 sqft
Lot size15 Acres
Year built2009
MLS #385332
Garage3 spaces
FireplaceGas
ViewPark
Private poolYes

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

© 2025 Tallahassee Board of REALTORS®, Inc. All rights reserved.

The data relating to real estate on this web site comes in part from the IDX Program of the Tallahassee Board of REALTORS®, Inc. Information herein is believed to be accurate and timely, but no warranty as such is expressed or implied. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. The broker providing this data believes it to be correct, but advises interested parties to confirm information before relying on it for a purchase decision.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
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

DateEventPrice
Oct 10, 2017
Home Sold
$725,000
Jun 08, 2006
Home Sold
$85,000
Mar 01, 2005
Home Sold
$50,000

Tax history

YearAssessmentProperty 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.

All data from GreatSchools

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.

How much money do the neighbors make?

43%
<35k
41%
35k-100k
10%
100k-200k
6%
200k+

What level of education do the neighbors have?

High School Diploma
Post Secondary Degree
Masters Degree
Doctorate

What types of families live nearby?

48%
Single, No Kids
14%
Single, with Kids
27%
Married, No Kids
11%
Married, with Kids

Are the neighbors home owners or renters?

Home Owners
Renters

How old are people in this area?

17%
<11 yrs old
7%
12-17 yrs old
20%
18-34 yrs old
40%
35-64 yrs old
16%
65+ yrs old

What do the neighbors do for fun?

  • NASCARNASCAR
  • Pro WrestlingPro Wrestling
  • Monster TrucksMonster Trucks

Where do the neighbors shop?

  • Dollar GeneralDollar General
  • Wal-MartWal-Mart
  • Bass Pro ShopsBass Pro Shops

Where do the neighbors go to eat?

  • Hardee'sHardee's
  • Jimmy JohnsJimmy Johns
  • ApplebeesApplebees

What do the neighbors drive?

  • GMCGMC
  • DodgeDodge
  • ChevroletChevrolet

What do the neighbors listen to?

  • Classic CountryClassic Country
  • CountryCountry
  • New CountryNew Country
All data provided by Home Junction and Claritas

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.

From Rocket Homes Real Estate and based on county public records data.

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