221 Kiley Drive
Monticello, FL 32344
5
Bed
5
Bath
5,476Sqft
5Acres(Lot)
Welcome to a rare North Florida estate just minutes from Tallahassee—where luxury, land, and lifestyle come together. 221 Kiley Road is situated on expansive acreage in Monticello, and this private retreat offers the perfect blend of seclusion and convenience, located just a short drive from the heart of Tallahassee. For buyers seeking space, privacy, and versatility without sacrificing proximity to town, this property delivers. 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 pictures
Property Details
Map
Map
What's Nearby
Nearby Areas
Features
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Bedroom Information
Total beds: 5Bathroom Information
Total Baths: 5 Full Baths: 4 Half Baths: 1Flooring Information
Bamboo, Tile -
Interior Features
WetBar, TrayCeilings, GardenTubRomanTub, HighCeilings, Other, StallShower, VaultedCeilings, CentralVacuum, EntranceFoyer, PrimaryDownstairs, Pantry, SplitBedrooms, SunRoom, WalkInClosetsAppliances: Dryer, Dishwasher, IceMaker, Microwave, Oven, Range, Refrigerator, Washer -
Heating & Cooling
Has Heating: Yes Heating: Central, Fireplaces, Other Has Cooling: Yes Cooling: CentralAir, CeilingFans, Electric
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Building Information
Year Built: 2009Building Area Total: 5476Construction Materials: BrickPatio And Porch Features: Covered, Patio, Porch, ScreenedPool Features: Concrete, InGround, PoolEquipmentPrivate Pool: YesView: ParkGreenbelt -
Exterior Features
Exterior Features: SprinklerIrrigation
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Lot Information
Lot Dimensions: 325x650x325x650 Lot Size Acres: 5Property Information
Subdivision: Timber Trace Source Property Type: Residential Property SubType: Detached Levels: MultiSplit Property Age: 17
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Listing Price Information
Listing Price: $1325000Cash, Conventional
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Tax Information
Parcel Number: 12065-26-2N-5E-0835-0000-0160 Tax Lot: 16 Tax Block: - Annual Tax: $8073
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Virtual Tour
Parking Information
ThreeCarGarage, ThreeOrMoreSpaces, GatedGarage Information
Has Garage: Yes Garage Space: 3Homeowners Association Information
Included Fees: Other, RoadMaintenance, StreetLightsHOA: $150.00
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School Information
Elementary School: Jefferson County K-12 School Junior High School: Jefferson County K-12 School Senior High School: Jefferson County K-12 School -
Location Information
Direction: Hwy 90 E. to Ashville Hwy, Right on Bassett Dairy Rd, Right on Kiley Dr., Home on left. Security Features: SecuritySystemOwned
How much is this property worth?
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Nearby Home Value
| Address | Estimate | Bed | Bath | Sq. Ft | Lot Size |
|---|---|---|---|---|---|
| TBD E Meadow Road, Monticello, FL, 32344 | $50,000 | -- | -- | -- | |
| 195 E Meadow Road, Monticello, FL, 32344 | $75,000 | 3 | 2 | 1,836 | 1,836 SqFt |
| 339 Silver Lake Rd., Monticello, FL, 32344 | $375,000 | 3 | 3 | 2,706 | 2,706 SqFt |
| 4589 Ashville Highway, Monticello, FL, 32344 | $695,000 | 3 | 3 | 3,832 | 3,832 SqFt |
| 221 Kiley Drive, Monticello, FL, 32344 | $1,549,000 | 5 | 5 | 5,476 | 5,476 SqFt |
| 4014 Ashville Highway, Monticello, FL, 32344 | $315,000 | 2 | 2 | 1,416 | 1,416 SqFt |
| 952 Turney Anderson Road, Monticello, FL, 32344 | $449,900 | 3 | 2 | 1,841 | 1,841 SqFt |
| 660 Whispering Hills Road, Monticello, FL, 32344 | $795,000 | 3 | 3 | 2,160 | 2,160 SqFt |
| 728 Turney Anderson Road, Monticello, FL, 32344 | $799,999 | 3 | 3 | 3,677 | 3,677 SqFt |
| 1205 E Pearl Street, Monticello, FL, 32344 | $397,000 | 3 | 3 | 2,373 | 2,373 SqFt |
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ByOwner last updated this listing 06/07/2026 @ 00:21
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