
221 Kiley Dr Monticello, FL 32344
Estimated payment $8,579/month
Highlights
- Horses Allowed On Property
- 15 Acre Lot
- Traditional Architecture
- Concrete Pool
- Vaulted Ceiling
- Bamboo Flooring
About This Home
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 Details
Home Type
- Single Family
Est. Annual Taxes
- $128
Year Built
- Built in 2009
Lot Details
- 15 Acre Lot
- Lot Dimensions are 325x650x325x650
- Property is Fully Fenced
- Sprinkler System
HOA Fees
- $13 Monthly HOA Fees
Parking
- 3 Car Garage
Home Design
- Traditional Architecture
- Split Level Home
- Brick Exterior Construction
- Slab Foundation
Interior Spaces
- 5,476 Sq Ft Home
- Multi-Level Property
- Wet Bar
- Central Vacuum
- Tray Ceiling
- Vaulted Ceiling
- Gas Fireplace
- Bonus Room
- Screened Porch
- Utility Room
- Washer
- Security System Owned
- Property Views
Kitchen
- Oven
- Range
- Microwave
- Ice Maker
- Dishwasher
Flooring
- Bamboo
- Tile
Bedrooms and Bathrooms
- 5 Bedrooms
- Split Bedroom Floorplan
- Walk-In Closet
- Garden Bath
Pool
- Concrete Pool
- In Ground Pool
Schools
- Jefferson County Schools Elementary School
- Jefferson County Middle School
- Jefferson County High School
Utilities
- Central Heating and Cooling System
- Power Generator
Additional Features
- Screened Patio
- Horses Allowed On Property
Listing and Financial Details
- Tax Lot 16
- Assessor Parcel Number 12065-26-2N-5E-0835-0000-0160
Community Details
Overview
- Association fees include road maintenance
- Timber Trace Subdivision
Amenities
- Office
Map
Home Values in the Area
Average Home Value in this Area
Tax History
Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
---|---|---|---|---|
2024 | $128 | -- | -- | -- |
2022 | $194 | $0 | $0 | $0 |
2021 | $385 | $0 | $0 | $0 |
Property History
Date | Event | Price | Change | Sq Ft Price |
---|---|---|---|---|
07/07/2025 07/07/25 | Price Changed | $1,549,000 | -3.1% | $283 / Sq Ft |
05/01/2025 05/01/25 | For Sale | $1,599,000 | -- | $292 / Sq Ft |
Similar Homes in Monticello, FL
Source: Capital Area Technology & REALTOR® Services (Tallahassee Board of REALTORS®)
MLS Number: 385332

- 339 Silver Lake Rd
- xxx Big Joe Rd
- 874 Flatwoods
- 0 Flatwoods
- 000 Kinsey Rd
- 740 Kinsey Rd
- 1069 N Salt Rd
- 94 W Meadow Ln
- 195 E Meadow Rd
- 0 Aucilla Rd Unit 22696476
- 0 S Salt Rd Unit MFRGC527327
- Lot 29, Block A E Meadow Rd
- Lot 30, Block A E Meadow Rd
- 130 Simpson Ave
- 1205 E Pearl St
- 952 Turney Anderson Rd
- 1125 E Dogwood St
- Vacant E Washington Hwy
- 205 N Rhodes St
- 685 E Washington St
- 625 E Washington St
- 24 Parkway Pines
- 946 Cap Tram Rd
- 100 Phillips Dr
- 2118 Wimbledon Dr
- 11369 Us Highway 84 E
- 1720 S Pinetree Blvd
- 124 Ginny Ln
- 8812 N Pembroke Ct
- 105 Old Boston Rd
- 1 Grand Park Ln
- 2555 Chateau Ln Unit 2
- 3999 Cottage Farm Rd
- 5339 Us 319 S
- 110 Lyon Ln
- 2005 E Pinetree Blvd
- 2015 E Pinetree Blvd
- 190 Harbor Ln
- 321 Madison Grove Blvd
- 134 Covington Place