Fastexpert Short LogoFastexpert Icon
Fastexpert Short Logo
  • Buy

      I'm Buying

      Connect with verified agents who specialize in helping buyers

      Find Top Agents
      RESOURCES
      Home Buying TipsProperties for SaleCity Data SearchAffordability CalculatorU.S. Market TrendsRent vs Buy CalculatorReal Estate Blog
  • Sell

      I'm Selling

      Get top dollar with agents who know your market

      Find Top Agents
      RESOURCES
      Home Value EstimatorNewHome Selling TipsClosing Cost CalculatorHomes Sold Near MeReal Estate BlogU.S. Market TrendsFind a Loan Officer
  • Mortgage

      Need a Mortgage

      Compare competitive rates from verified local loan officers

      Find Loan Officers
      RESOURCES
      Find a Loan OfficerMortgage CalculatorFinance & LegalRefinance CalculatorGet Pre-Approved
  • Advice
  • For Pros
    • Real Estate Agents

      Verified referrals from buyers and sellers.

      JoinReal Estate Agents
    • Loan Officers

      Connect with motivated buyers and agents.

      JoinLoan Officers
    • Service Professionals

      Movers, inspectors, contractors, and more.

      JoinService Professionals
  • Company

      Browse the Pro Directory

      Find movers, inspectors, contractors and other vetted professionals near you

      View Directory
      RESOURCES
      About UsAuthorsLeadershipFastExpert CaresFact SheetContact UsClient Reviews
Join Our Network
Find a Top Real Estate Agent Today

Sellers & Buyers

  • Learn More
  • Home Selling Tips
  • Homes Sold Near Me
  • Properties For sale
  • City Data Search
  • Community Questions
  • Ask a Licensed Agent
  • Real Estate Blog
  • Home Buying Tips
  • U.S. Market Trends

Tools

  • Mortgage Calculator
  • Affordability Calculator
  • Rent vs Buy Calculator
  • Closing Cost Calculator
  • Refinance Calculator

Agents

  • Login
  • Sign Up
  • Learn More
  • FastExpert App

Company

  • About Us
  • Leadership
  • Fact Sheet
  • Client Reviews
  • How We Verify Reviews
  • Contact Us
  • Authors

Support

Phone
1-800-319-0511

Mon-Fri 8AM-4PM PST

Email
[email protected]

24/7 Response

Follow Us

  • Facebook
  • Twitter
  • LinkedIn
  • Instagram
  • YouTube
  • RSS
  • BBB

FastExpert, Inc is a California Licensed Broker. CA License #01950016

Terms | Privacy | Cookie Policy | Do Not Call Policy | California Privacy Notice | Accessibility Notice | Site Map | FastExpert, inc. © 2026. All Rights Reserved.

    1. Home
    2. Property for sale
    3. Florida
    4. Monticello, FL
    5. 221 Kiley Dr
    221 Kiley Dr Monticello, FL 32344  | Single Family
    1 / 42

    $1,599,000

    221 Kiley Dr Monticello, FL 32344
    5
    Bedrooms
    5
    Bathrooms
    15
    Acres
    2009
    Year Built
    Single Family
    Property Type
    offer icon

    Special Offer:

    (If you do not have an agent and work directly with the listing agent)

    No

    About This Home

    Welcome to a rare and exquisite 15-acre modern, luxury estate, where timeless elegance meets Southern charm. Custom built by Riley Palmer, this exclusive 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. 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). Notable Estate Features list available. Room measurements approximate. Buyer to verify. Welcome home!

    Location

    221 Kiley Dr Monticello, FL 32344

    Loading map...

    Similar Homes for Sale

    View all
    68 SE 12th Ave Cross City, FL 32628
    12 months ago
    $129,900
    68 SE 12th Ave Cross City, FL 32628
    3 Beds
    1 Baths
    1606 3rd Ave SE Steinhatchee, FL 32359
    12 months ago
    $2,100,000
    1606 3rd Ave SE Steinhatchee, FL 32359
    4 Beds
    3 Baths
    1 Sqft
    7910 SW 25th Pl Bell, FL 32619
    2 years ago
    $349,900
    7910 SW 25th Pl Bell, FL 32619
    2 Beds
    1 Baths

    Listing Agent

    Barbra Boutin

    Barbra Boutin

    Engel & Volkers Tallahassee

    (23 reviews)
    Avg Price Sold$480.6K
    Years Experience7
    Total Transactions85