Active

221 Kiley Drive

Monticello, FL 32344
Mark as Favorite
Bed 5

Bed

Bath 5

Bath

SqFt5,476

Sqft

SqFt653,400

Sqft(Lot)

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 gou rmet, 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!

Read More Expand

Detail Ic Property Details

Property Type : Residential

Price : $1,549,000

AD Id : 52208674

MLS Id : 385332

Beds : 5

Lot Size : 653,400 Sqft

Living Area Size : 5,476

Year Built : 2009

Garage : 3

County : Jefferson

Subdivision: Skyline Valley Ph 2

  • Map Map

Map

Map What's Nearby

Map Nearby Areas

Feature Features

  • Bedroom Information

    Total beds: 5

    Bathroom Information

    Total Baths: 5 Full Baths: 4 Half Baths: 1

    Flooring Information

    Bamboo, Tile
  • Interior Features

    WetBar, TrayCeilings, GardenTubRomanTub, HighCeilings, StallShower, VaultedCeilings, CentralVacuum, Pantry, SplitBedrooms, WalkInClosets
    Appliances: Dryer, Dishwasher, IceMaker, Microwave, Oven, Range, Refrigerator, Washer
  • Heating & Cooling

    Has Heating: Yes Heating: Central, Electric, Fireplaces Has Cooling: Yes Cooling: CentralAir, CeilingFans, Electric

  • Building Information

    Year Built: 2009
    Building Area Total: 5476
    Construction Materials: Brick
    Patio And Porch Features: Patio, Porch, Screened
    Pool Features: Concrete, InGround
    Private Pool: Yes
    View: ParkGreenbelt
  • Exterior Features

    Exterior Features: FullyFenced, SprinklerIrrigation

  • Lot Information

    Lot Dimensions: 325x650x325x650 Lot Size Acres: 15

    Property Information

    Subdivision: Timber Trace Source Property Type: Residential Property SubType: Detached Levels: MultiSplit Property Age: 17

  • Listing Price Information

    Listing Price: $1549000
    Original Price: $1599000
    Conventional

  • Tax Information

    Parcel Number: 12065-26-2N-5E-0835-0000-0160 Tax Lot: 16 Tax Block: -

  • Parking Information

    ThreeCarGarage, ThreeOrMoreSpaces

    Garage Information

    Has Garage: Yes Garage Space: 3

    Homeowners Association Information

    Included Fees: Other, RoadMaintenance
    HOA: $150.00

  • School Information

    Elementary School: Jefferson County Schools Junior High School: Jefferson County Middle School Senior High School: Jefferson County High 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
Sell a home like this and save $92,441 Find out How

How much is this property worth?

Curious about this home's true market value? Use our free Home Evaluation Tool to instantly get a personalized Comparative Market Analysis (CMA) report. Make smarter, data-driven decisions before you buy.

Images
Loading, please wait...

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 $1,325,000 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

The information being provided by Miami Association of REALTORS® is for the consumer's personal, non-commercial use. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Miami Association of REALTORS®. The accuracy of all information is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by Miami Association of REALTORS® and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited. Copyright 2026 Miami Association of REALTORS®. All rights reserved.

ByOwner last updated this listing 06/09/2026 @ 03:51

MLS: 385332 LISTED BY: Barbra Boutin, Engel & Völkers Tallahassee 386-623-2806 SOURCE: TBRMLS

Selling? Save $92,441 when you sell a home like this

Tour with a ByOwner Agent