221 Kiley Drive
Monticello, FL 32344
- 5 beds
- 5 baths
- 5,476 sqft
- ~15 acre lot
- $292 per sqft
- 2009 build
- – on site
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 is nestled just minutes from Tallahassee, Florida's Capital City, and Thomasville, GA in Monticello-home to a storied opera house and chic dining options-and offers the perfect blend of privacy, prestige and proximity. The heart of the estate is a grand Great House, designed for both refined living and effortless entertaining. Soaring ceilings, elegant finishes, and a gourmet 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. 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 micro-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. Work and play from home with ample connectivity powered by Conexon Connect, the leading optic fiber broadband solution! 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. 15 acres includes 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). Pop's Sanitation Waste Pick up option. Room measurements approximate. Buyer to verify. Welcome home!
Last checked:
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Checking…
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Last updated May 13, 2025
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MLS# 385332 —
The Building
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Year Built:2009
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Architectural Style:SplitLevel,Traditional
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Foundation Details:Slab
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Levels:MultiSplit
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Exterior Features:FullyFenced,SprinklerIrrigation
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Security Features:SecuritySystemOwned
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Patio And Porch Features:Patio,Porch,Screened
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Construction Materials:Brick
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Building Area Total:5476.0
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Building Area Source:Assessor
Interior
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Interior Features:WetBar,TrayCeilings,GardenTubRomanTub,HighCeilings,StallShower,VaultedCeilings,CentralVacuum,Pantry,SplitBedrooms,WalkInClosets
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Flooring:Bamboo,Tile
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Fireplace:true
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Fireplace Features:Gas
Room Dimensions
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Living Area:5476.0
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Living Area Source:Assessor
Financial & Terms
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Lease Considered:false
Location
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Directions:Hwy 90 E. to Ashville Hwy, Right on Bassett Dairy Rd, Right on Kiley Dr., Home on left.
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Latitude:30.539694
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Longitude:-83.792009
The Property
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Property Type:Residential
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Property Subtype:Detached
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Lot Size Acres:15.0
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Lot Size Dimensions:325x650x325x650
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Road Responsibility:PrivateMaintainedRoad
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Parcel Number:12065-26-2N-5E-0835-0000-0160
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View:ParkGreenbelt
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View:true
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Fencing:Fenced
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Horse Amenities:HorsesAllowed
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Other Equipment:Generator
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Waterfront:false
Listing Agent
- Contact info:
- Agent phone:
- (850) 597-0080
- Office phone:
- (386) 623-2806
Taxes
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Tax Lot:16
Beds
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Total Bedrooms:5
Baths
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Total Baths:5
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Half Baths:1
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Full Baths:4
The Listing
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Home Warranty:false
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Virtual Tour URL Unbranded:https://youtu.be/nXiNRyIYNs4
Heating & Cooling
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Heating:Central,Electric,Fireplaces
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Heating:true
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Cooling:CentralAir,CeilingFans,Electric
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Cooling:true
Utilities
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Sewer:SepticTank
Appliances
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Appliances:Dryer,Dishwasher,IceMaker,Microwave,Oven,Range,Refrigerator,Washer
Schools
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Elementary School:Jefferson County Schools
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Middle Or Junior School:Jefferson County Middle School
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High School:Jefferson County High School
The Community
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Subdivision Name:Timber Trace
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Association Fee:150.0
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Association Fee Includes:Other,RoadMaintenance
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Pool Features:Concrete,InGround
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Pool Private:true
Parking
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Garage:true
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Garage Spaces:3.0
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Parking Features:ThreeCarGarage,ThreeOrMoreSpaces
Monthly cost estimate

Asking price
$1,599,000
Expense | Monthly cost |
---|---|
Mortgage
This calculator is intended for planning and education purposes only. It relies on assumptions and information provided by you regarding your goals, expectations and financial situation, and should not be used as your sole source of information. The output of the tool is not a loan offer or solicitation, nor is it financial or legal advice. |
$8,562
|
Taxes | N/A |
Insurance | $439 |
Utilities | $258 See report |
Total | $9,259/mo.* |
*This is an estimate |
Walk Score®
Provided by WalkScore® Inc.
Walk Score is the most well-known measure of walkability for any address. It is based on the distance to a variety of nearby services and pedestrian friendliness. Walk Scores range from 0 (Car-Dependent) to 100 (Walker’s Paradise).
Bike Score®
Provided by WalkScore® Inc.
Bike Score evaluates a location's bikeability. It is calculated by measuring bike infrastructure, hills, destinations and road connectivity, and the number of bike commuters. Bike Scores range from 0 (Somewhat Bikeable) to 100 (Biker’s Paradise).
Air Pollution Index
Provided by ClearlyEnergy
The air pollution index is calculated by county or urban area using the past three years data. The index ranks the county or urban area on a scale of 0 (best) - 100 (worst) across the United Sates.
Sale history
Date | Event | Source | Price | % Change |
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5/1/25
May 1, 2025
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Listed / Active | CATRS | $1,599,000 |