Jefferson County, FL Homes

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  /5

  $56,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  599 E Buckhorn Trail, Greenville, FL 32331

  Come and get a slice of nature in the great state of Florida. This home give you a middle of nowhere experience while still being a short distance from civilization and local shops. Yes, you read that right, over 5 acres of land to call home. Schedule a showing today!

  Bronson Cheeks Vylla Home

  599 E Buckhorn Trail, Greenville, FL 32331
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  /2

  $27,000 Sold Sep 30, 2025

  00 Gamble Rd, Monticello, FL 32344

  • Land
  • 1.25 Acres
  • $21,600 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 6 Days On Market

  Last Listing Agent Thomas Lado WHITETAIL PROPERTIES REAL ESTATE

  00 Gamble Rd, Monticello, FL 32344
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  /42

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  1465 Florida Ave, Monticello, FL 32344

  1465 Florida Ave, Monticello, FL 32344
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  /45

  $269,000

  • 4 Beds
  • 2 Baths
  • 1,812 Sq Ft

  685 E Washington St, Monticello, FL 32344

  Perfect brick family home right downtown! Walk to the veggie stand across the street and all the Monticello shops! Renovated 4-bed, 2-bath home. New roof!! New Custom Kitchen cabinets, granite counters, and SS Appliance package perfect for you home chefs. The open-plan kitchen opens directly into the dining and living room. New Flooring, Paint, Light fixtures, Custom closets and bookcases

  Lee Hall Capital City Real Estate Group

  685 E Washington St, Monticello, FL 32344
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  /2

  $40,000 Sold Dec 16, 2025

  23 & 45 Armstrong Rd, Monticello, FL 32344

  • Land
  • 8.47 Acres
  • $4,723 per Acre

  Last Sold Summary

  • 60% Below List Price
  • 139 Days On Market

  Last Listing Agent Bruce Carpenter Avenue Realty FL

  23 & 45 Armstrong Rd, Monticello, FL 32344
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  /23

  Est $633,977 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,205 Sq Ft

  60 White Oak Dr, Monticello, FL 32344

  60 White Oak Dr, Monticello, FL 32344
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  /4

  $75,000

  • Land
  • 0.29 Acre
  • $258,621 per Acre

  205 E Cherokee Ave, Monticello, FL 32344

  Prime vacant cleared commercial lot in downtown Monticello. Zoned Commercial B-2 Business Highway. Located Steps from US 19 South Across street from Burger King and Dollar Tree. Next door to Oreilly's Auto parts. High Traffic area and Good visibility. Address is for GPS only. Acreage is subject to survey.

  Starbuck Rissman Steve C. Walker Realty, LLC

  205 E Cherokee Ave, Monticello, FL 32344
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  /38

  $550,000 Sold Sep 02, 2025

  151 N Ojibwa Rd, Monticello, FL 32344

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 2000

  Last Sold Summary

  • 4% Below List Price
  • $229/SF
  • 47 Days On Market

  Current Estimated Value $550,319

  Last Listing Agent Clint Bailey Superior Realty Group LLC

  151 N Ojibwa Rd, Monticello, FL 32344
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  /42

  Est $839,280 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,006 Sq Ft

  715 Brock Rd, Monticello, FL 32344

  715 Brock Rd, Monticello, FL 32344
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  /2

  $40,000 Under Contract

  • Land
  • 2.3 Acres
  • $17,391 per Acre

  0 Mallard Ln Unit 394437, Monticello, FL 32344

  Escape to peace & privacy, and with this beautiful 2.30-acre homesite located in the Lloyd Acres / Mallard Lane area of Jefferson County. Whether you’re planning your next home, a weekend retreat, or a smart land investment, this property offers the perfect blend of rural living with convenient access to Monticello and Tallahassee. Enjoy the natural surroundings, abundant trees, and quiet country

  Hunter Bowden Keller Williams Town & Country

  0 Mallard Ln Unit 394437, Monticello, FL 32344
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  /10

  $157,900 Sold Mar 10, 2025

  396 Mallard Ln, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 2025

  Last Sold Summary

  • 5% Above List Price
  • $137/SF
  • 4 Days On Market

  Last Listing Agent E. Bradley Vollertsen Advanced Real Estate Sales

  396 Mallard Ln, Monticello, FL 32344
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  /15

  Not Listed For Sale

  Lots 13-17 Cardinal Ln, Monticello, FL 32344

  Lots 13-17 Cardinal Ln, Monticello, FL 32344
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  /24

  $85,000 Under Contract

  • Land
  • 6.42 Acres
  • $13,240 per Acre

  Vacant E Washington Hwy, Monticello, FL 32344

  ?? 6.42 Acres For Sale – Fronting US 90! ??? ?? Located less than 10 miles from Downtown Monticello ?? Peaceful, quiet setting just minutes from amenities ?? Well, power, and septic already installed – ready to build! ?? Multiple homesites to choose from ?? No HOA – total freedom to create your dream retreat ?? Excellent hunting potential – deer, turkey & ducks ?? Pond onsite – perfect for

  Ben Jones Southern Land & Homes

  Vacant E Washington Hwy, Monticello, FL 32344
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  /52

  $569,000 Sold Nov 21, 2025

  57 Sunset Dr, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,976 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Above List Price
  • $288/SF
  • 73 Days On Market

  Last Listing Agent Chance Shutes Keller Williams Town & Country

  57 Sunset Dr, Monticello, FL 32344
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  /39

  Est $412,187 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft

  1660 Willow Rd, Monticello, FL 32344

  1660 Willow Rd, Monticello, FL 32344
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  /32

  $425,000 Sold Jan 12, 2026

  1610 Yaupon Ct, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,858 Sq Ft
  • Built 2023

  Last Sold Summary

  • $229/SF
  • 23 Days On Market

  Last Listing Agent Chance Shutes Keller Williams Town & Country

  1610 Yaupon Ct, Monticello, FL 32344
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  /42

  Est $421,077 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft

  1640 Willow Rd, Monticello, FL 32344

  1640 Willow Rd, Monticello, FL 32344
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  /47

  $449,000 Sold Sep 09, 2025

  1293 Vista Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 2,334 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Below List Price
  • $192/SF
  • 47 Days On Market

  Current Estimated Value $447,828

  Last Listing Agent Leanne Groom The Naumann Group Real Estate

  1293 Vista Rd, Monticello, FL 32344
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  /41

  Est $604,628 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,806 Sq Ft

  808 Paul Thompson Rd, Monticello, FL 32344

  808 Paul Thompson Rd, Monticello, FL 32344
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  /17

  $110,000 Sold Jul 31, 2025

  55 W Cavallo Trail, Monticello, FL 32344

  • Land
  • 11.17 Acres
  • $9,848 per Acre

  Last Sold Summary

  • 37% Below List Price
  • 310 Days On Market

  Current Estimated Value $114,654

  Last Listing Agent Tully Sparkman Bluewater Realty Group

  55 W Cavallo Trail, Monticello, FL 32344
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  /5

  Not Listed For Sale

  957 NW White Wing Dove Dr, Greenville, FL 32331

  957 NW White Wing Dove Dr, Greenville, FL 32331
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  /42

  $900,000 Sold May 08, 2025

  542 Tradition Way, Monticello, FL 32344

  • 4 Beds
  • 2.5 Baths
  • 2,750 Sq Ft
  • Built 2018

  Last Sold Summary

  • 3% Below List Price
  • $327/SF
  • 38 Days On Market

  Current Estimated Value $897,085

  Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

  542 Tradition Way, Monticello, FL 32344
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  /28

  Est $283,836 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  1102 Smokehouse Farms Dr, Greenville, FL 32331

  1102 Smokehouse Farms Dr, Greenville, FL 32331
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  /20

  $360,000 Sold Jul 11, 2025

  Lot 4 Watermill Rd, Monticello, FL 32344

  • Land
  • 31.22 Acres
  • $11,531 per Acre

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Sarah McKinzie Hum Real Estate

  Lot 4 Watermill Rd, Monticello, FL 32344
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  /42

  Est $783,293 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,539 Sq Ft

  158 Tradition Way, Monticello, FL 32344

  158 Tradition Way, Monticello, FL 32344
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  /13

  $97,000 Sold Aug 29, 2025

  Lot 4 Hiawatha Farms S, Monticello, FL 32344

  • Land
  • 4.25 Acres
  • $22,824 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 26 Days On Market

  Last Listing Agent Stacie Boone Engel & Völkers Tallahassee

  Lot 4 Hiawatha Farms S, Monticello, FL 32344
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  /26

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft

  665 N Cherry St, Monticello, FL 32344

  665 N Cherry St, Monticello, FL 32344
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  /42

  $525,000 Sold Jun 25, 2025

  178 Nautilus Dr, Monticello, FL 32344

  • 2 Beds
  • 2 Baths
  • 1,907 Sq Ft
  • Built 1996

  Last Sold Summary

  • 12% Below List Price
  • $275/SF
  • 16 Days On Market

  Last Listing Agent Ondrea Maldonado Hamilton Realty Advisors LLC

  178 Nautilus Dr, Monticello, FL 32344
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  /40

  Est $462,333 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 765 Sq Ft

  1911 Ashville Highlands Dr, Greenville, FL 32331

  1911 Ashville Highlands Dr, Greenville, FL 32331
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  /70

  $925,000 Sold Dec 15, 2025

  2024 Old Lloyd Rd, Monticello, FL 32344

  • 4 Beds
  • 3 Baths
  • 4,600 Sq Ft
  • Built 1945

  Last Sold Summary

  • 6% Below List Price
  • $201/SF
  • 113 Days On Market

  Last Listing Agent Katherine Hansli Searcy The Naumann Group Real Estate

  2024 Old Lloyd Rd, Monticello, FL 32344
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  /42

  Est $569,556 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,879 Sq Ft

  919 Heritage Blvd, Monticello, FL 32344

  919 Heritage Blvd, Monticello, FL 32344
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  /30

  $349,000 Sold Jun 16, 2025

  460 W Osprey Ln, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1991

  Last Sold Summary

  • $208/SF
  • 72 Days On Market

  Current Estimated Value $356,687

  Last Listing Agent Hines Boyd FL-GA Realty & Auction

  460 W Osprey Ln, Monticello, FL 32344
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  /33

  Est $351,164 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,960 Sq Ft

  565 Monticello Ave, Monticello, FL 32344

  565 Monticello Ave, Monticello, FL 32344
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  /34

  $300,000 Sold Jun 20, 2025

  4014 Ashville Hwy, Monticello, FL 32344

  • 2 Beds
  • 2 Baths
  • 1,416 Sq Ft
  • Built 1993

  Last Sold Summary

  • 5% Below List Price
  • $212/SF
  • 55 Days On Market

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc

  4014 Ashville Hwy, Monticello, FL 32344
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  /9

  Not Listed For Sale

  208 Wood Duck, Monticello, FL 32344

  208 Wood Duck, Monticello, FL 32344
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  /43

  $237,000 Sold Dec 15, 2025

  2029 Boston Hwy, Monticello, FL 32344

  • 2 Beds
  • 2 Baths
  • 1,922 Sq Ft
  • Built 2015

  Last Sold Summary

  • 9% Below List Price
  • $123/SF
  • 55 Days On Market

  Last Listing Agent Alex Nunez Twelve Points Real Estate, LLC

  2029 Boston Hwy, Monticello, FL 32344
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  /38

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,709 Sq Ft

  145 Coopers Pond Rd, Monticello, FL 32344

  145 Coopers Pond Rd, Monticello, FL 32344
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  /20

  $396,494 Sold Jun 30, 2025

  Lot 3 Watermill Rd, Monticello, FL 32344

  • Land
  • 31.22 Acres
  • $12,700 per Acre

  Last Sold Summary

  • 10% Above List Price
  • 44 Days On Market

  Last Listing Agent Sarah McKinzie Hum Real Estate

  Lot 3 Watermill Rd, Monticello, FL 32344
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  /16

  Est $550,156 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,904 Sq Ft

  7390 Waukeenah Hwy, Monticello, FL 32344

  7390 Waukeenah Hwy, Monticello, FL 32344
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  /39

  $425,000 Sold Jun 04, 2025

  120 Lacapra Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 2,822 Sq Ft
  • Built 2005

  Last Sold Summary

  • $151/SF
  • 28 Days On Market

  Current Estimated Value $443,617

  Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

  120 Lacapra Rd, Monticello, FL 32344

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