Jefferson County, FL Homes

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  $94,500 Sold Sep 05, 2025

  0 W Osprey Ln Unit 381026, Monticello, FL 32344

  • Land
  • 20 Acres
  • $4,725 per Acre

  Last Sold Summary

  • 32% Below List Price
  • 222 Days On Market

  Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

  0 W Osprey Ln Unit 381026, Monticello, FL 32344
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  Not Listed For Sale

  A Salt Rd, Monticello, FL 32344

  A Salt Rd, Monticello, FL 32344

  Last Sold Summary

  • 86 Days On Market

  Last Sold Price $390,000

  Last Listing Agent Sherry Shaheen ENGEL & VOLKERS GAINESVILLE
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  /54

  $149,000

  • 2 Beds
  • 2 Baths
  • 1,792 Sq Ft

  12447 Gamble Rd, Monticello, FL 32344

  Seller Ready to Not be the Owner Anymore! Corner Lot! This 2 bedroom (could be a 3rd Bdrm however the 3rd bedroom does not have a closet but most 1930's homes did not have closets), 2 bathroom home offers 1,792 sq ft of living on 1 acre in Wacissa, Florida, just 1 minute from the Wacissa River headwaters (first magnitude Spring) and boat launch in Monticello, Jefferson County, Florida. It’s an

  Catherine Hope All Realty Services

  12447 Gamble Rd, Monticello, FL 32344
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  /41

  $336,000 Sold Jun 23, 2025

  1600 Sweetbay Ct, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,555 Sq Ft
  • Built 2021

  Last Sold Summary

  • $216/SF
  • 33 Days On Market

  Last Listing Agent Amber Renaud The Nova Group Realty

  1600 Sweetbay Ct, Monticello, FL 32344
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  /5

  Not Listed For Sale

  354 W 12th Dr, Greenville, FL 32331

  354 W 12th Dr, Greenville, FL 32331

  Last Sold Summary

  • 253 Days On Market

  Last Sold Price $35,000

  Last Listing Agent Kyle Geoghagan Keller Williams Town & Country
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  /48

  $1,000,000 Under Contract

  • 8 Beds
  • 6.5 Baths
  • 5,560 Sq Ft

  237 Valley View Ct, Monticello, FL 32344

  Opportunities like this are rare! You've been seeking close in country life. Enjoy the perfect balance of privacy and convenience on 15 acres with a true Estate. A main home, guest home, efficiency apartment, barn, climate controlled storage, life sized doll house with electric, screened pool, and whole home generator offer the perfect multi-generational set up and breathtaking sunset views just

  Kelly Vinson Keller Williams Town & Country

  237 Valley View Ct, Monticello, FL 32344
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  /33

  $140,000 Sold Jan 09, 2026

  720A Indian Hills Rd, Monticello, FL 32344

  • Land
  • 10.62 Acres
  • $13,183 per Acre

  Last Sold Summary

  • 26% Below List Price
  • 131 Days On Market

  Last Listing Agent Alicia Radtke All Realty Services

  720A Indian Hills Rd, Monticello, FL 32344
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  /36

  Not Listed For Sale

  87 Old Tung Grove Rd, Monticello, FL 32344

  • 4 Beds
  • 3 Baths
  • 2,344 Sq Ft
  • Built 2024

  87 Old Tung Grove Rd, Monticello, FL 32344

  Last Sold Summary

  • $288/SF
  • 362 Days On Market

  Last Sold Price $675,000

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc
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  /24

  $174,900

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  963 Quail Ln, Monticello, FL 32344

  Great location for this property in Lloyd Acres. The property has 2.26 acres of partially wooded area. The property consists of the single family home, detached garage/carport/workshop and a singlewide mobile home. The vinyl sided home will need some repair and updating but has tremendous potential. The detached garage is large with 2 stalls. The mobile home is in need of a total renovation (or

  Van Drake Drake Realty, Inc.

  963 Quail Ln, Monticello, FL 32344
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  /63

  $500,000 Sold Oct 24, 2025

  282 Long Leaf Dr, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 2,170 Sq Ft
  • Built 1998

  Last Sold Summary

  • 4% Below List Price
  • $230/SF
  • 95 Days On Market

  Current Estimated Value $507,202

  Last Listing Agent Catherine Hope All Realty Services

  282 Long Leaf Dr, Monticello, FL 32344
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  /37

  Not Listed For Sale

  185 White Oak Dr, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,976 Sq Ft
  • Built 2024

  185 White Oak Dr, Monticello, FL 32344

  Last Sold Summary

  • $281/SF
  • 69 Days On Market

  Last Sold Price $555,000

  Last Listing Agent Marshall Gibbs Capital City Real Estate Group
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  /42

  $325,000

  • 4 Beds
  • 3 Baths
  • 2,223 Sq Ft

  155 E Seminole Ave, Monticello, FL 32344

  Set along one of Monticello’s main routes, this 1950s home offers a rare chance to create something truly your own—whether that’s a residence, a business, or a thoughtful mix of both, with flexible Business/Residential zoning already in place. Sitting on 0.60 acres with over 2,200 square feet, the layout is surprisingly adaptable, with 4 bedrooms and 3 full bathrooms, including multiple ensuite

  Catherine Hope All Realty Services

  155 E Seminole Ave, Monticello, FL 32344
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  /37

  $125,000 Sold Nov 12, 2025

  1150 Old Lloyd Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,376 Sq Ft
  • Built 1982

  Last Sold Summary

  • 7% Below List Price
  • $91/SF
  • 14 Days On Market

  Last Listing Agent Alicia Radtke All Realty Services

  1150 Old Lloyd Rd, Monticello, FL 32344
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  /22

  Not Listed For Sale

  390 Elliot Dr, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,351 Sq Ft
  • Built 2024

  390 Elliot Dr, Monticello, FL 32344

  Last Sold Summary

  • $218/SF
  • 28 Days On Market

  Last Sold Price $295,000

  Last Listing Agent Buddy Witmer Steve C. Walker Realty, LLC
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  /11

  $45,000

  • Land
  • 5.01 Acres
  • $8,982 per Acre

  TBD Aucilla Plantation Ct, Greenville, FL 32331

  5.01 wooded acres, well known for the large amount of Indian Artifacts due to the nearby Aucilla River, beautiful native trees, close to Smokehouse boat landing, Aucilla Shores Subdivision contains a private airstrip, animal Friendly & only a couple miles off Ashville Highway on well maintained roads.

  Justin Peel Maclay Realty & Management LLC

  TBD Aucilla Plantation Ct, Greenville, FL 32331
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  $541,000 Sold May 23, 2025

  Vacant Hartsfield Rd, Monticello, FL 32344

  • Land
  • 59.17 Acres
  • $9,143 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 55 Days On Market

  Last Listing Agent Ben Jones Southern Land & Homes

  Vacant Hartsfield Rd, Monticello, FL 32344
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  Est $737,314 Not Listed For Sale

  12840 Gamble Rd, Monticello, FL 32344

  • 6 Beds
  • 4 Baths
  • 3,998 Sq Ft
  • Built 1991

  12840 Gamble Rd, Monticello, FL 32344

  Last Sold Summary

  • 8% Above List Price
  • $170/SF
  • 54 Days On Market

  Last Sold Price $680,000

  Last Listing Agent Chris Cicatello Coldwell Banker Hartung
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  /12

  $399,000

  • Land
  • 60 Acres
  • $6,650 per Acre

  0 Fallow Rd Unit 373902, Lamont, FL 32336

  Private recreational tract located in western Jefferson County surrounded by very large managed private tracts. The quality of game rivals the best low fence hunting Florida has to offer. White tailed deer, wild turkey, ducks and bears. Owners have seen no sign of wild hogs. The 60 acres has good access off Fallow Road with building sites on both sides of the road. The majority of the acreage is

  Monroe Rogers Landcorp, Inc.

  0 Fallow Rd Unit 373902, Lamont, FL 32336
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  /40

  $546,000 Sold Oct 14, 2025

  44 S Ojibwa Rd, Monticello, FL 32344

  • 4 Beds
  • 3.5 Baths
  • 2,771 Sq Ft
  • Built 2005

  Last Sold Summary

  • 19% Below List Price
  • $197/SF
  • 98 Days On Market

  Current Estimated Value $544,064

  Last Listing Agent Brett Miller Legacy Pro Real Estate Group

  44 S Ojibwa Rd, Monticello, FL 32344
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  /38

  Est $246,485 Not Listed For Sale

  5118 E Washington Hwy, Monticello, FL 32344

  • 2 Beds
  • 1.5 Baths
  • 1,276 Sq Ft
  • Built 1935

  5118 E Washington Hwy, Monticello, FL 32344

  Last Sold Summary

  • 14% Above List Price
  • $170/SF
  • 21 Days On Market

  Last Sold Price $217,000

  Last Listing Agent Amber Renaud The Nova Group Realty
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  $200,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,741 Sq Ft

  265 W Seminole Ave, Monticello, FL 32344

  You must see this -Charming all-brick corner-lot home ideally located directly across from the Legion Hall and the entrance to Monticello Ecological Park—plus just a short walk to midtown shops and restaurants. The screened In front porch welcomes you inside. Inside, you’ll find wood floors (including beneath the carpet in the bonus room) and a layout that offers flexibility for today’s living.

  Karen Gillispie Keller Williams Town & Country

  265 W Seminole Ave, Monticello, FL 32344
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  /6

  $170,000 Sold Dec 03, 2025

  000 Barnes Rd, Monticello, FL 32344

  • Land
  • 14.62 Acres
  • $11,628 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 37 Days On Market

  Last Listing Agent H. Trey Hough Armor Realty, Inc

  000 Barnes Rd, Monticello, FL 32344
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  /5

  Not Listed For Sale

  271 Tecumseh Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 2,128 Sq Ft
  • Built 1989

  271 Tecumseh Rd, Monticello, FL 32344

  Last Sold Summary

  • $96/SF
  • 20 Days On Market

  Last Sold Price $205,000

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc
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  /61

  $545,000

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

  2184 Tram Rd, Monticello, FL 32344

  BEAUTIFULLY UPDATED ACREAGE HOME ON 22 ACRES WITH POND AND BLUEBERRIE FIELDS! UNIQUE PROPERTY WITH ACRES OF BLUEBERRIES, plus 60x 23, 4 bay garage with heated and cooled office, gym or storage space, 22x23 pole barn and 64x32 large red barn with kitchen and 2 bathrooms, 2 gazebo's, storage shed and more! There is plenty of room to roam on this beautiful property with over $195,000 of updates! The

  Penny Herman Penny Herman Realty

  2184 Tram Rd, Monticello, FL 32344
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  /27

  $349,900 Sold Jul 18, 2025

  149 Coopers Pond Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,601 Sq Ft
  • Built 2025

  Last Sold Summary

  • $219/SF
  • 106 Days On Market

  Last Listing Agent Tiffany Kasdorf Kozloski Realty, LLC

  149 Coopers Pond Rd, Monticello, FL 32344
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  /5

  Not Listed For Sale

  0 W Osprey Ln, Monticello, FL 32344

  0 W Osprey Ln, Monticello, FL 32344

  Last Sold Summary

  • 108 Days On Market

  Last Sold Price $104,000

  Last Listing Agent Ondrea Maldonado Hamilton Realty Advisors LLC
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  /31

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft

  104 Pine Cone Dr, Monticello, FL 32344

  This gorgeous, 3-bedroom, 2-bath modular home, recently renovated by Paul Davis, combines modern comfort and style. Inside, you’ll find an open floor plan, a brand-new kitchen with granite countertops, new appliances, and updated finishes that make everyday living and entertaining a joy. The primary bedroom offers a luxurious ensuite with double vanities, a walk-in shower, and garden tub, as well

  Trevor Ann Clark Keller Williams Town & Country

  104 Pine Cone Dr, Monticello, FL 32344
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  /41

  $220,000 Sold Apr 21, 2025

  370 Brown Rd, Lamont, FL 32336

  • 3 Beds
  • 2 Baths
  • 1,247 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Above List Price
  • $176/SF
  • 73 Days On Market

  Current Estimated Value $172,922

  Last Listing Agent Catherine Hope All Realty Services

  370 Brown Rd, Lamont, FL 32336
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  Not Listed For Sale

  157 White Oak Dr, Monticello, FL 32344

  • 4 Beds
  • 2 Baths
  • 1,801 Sq Ft
  • Built 2024

  157 White Oak Dr, Monticello, FL 32344

  Last Sold Summary

  • $261/SF

  Last Sold Price $470,060

  Last Listing Agent Marylou Johnston Keller Williams Town & Country
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  $1,325,000

  • 5 Beds
  • 4.5 Baths
  • 5,476 Sq Ft

  221 Kiley Dr, Monticello, FL 32344

  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

  Wilda Sigler Keller Williams Town & Country

  221 Kiley Dr, Monticello, FL 32344
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  $480,000 Sold Sep 26, 2025

  885 S Waukeenah St, Monticello, FL 32344

  • 5 Beds
  • 3.5 Baths
  • 4,600 Sq Ft
  • Built 1882

  Last Sold Summary

  • 9% Below List Price
  • $104/SF
  • 63 Days On Market

  Current Estimated Value $502,104

  Last Listing Agent Jason Boone Keller Williams Town & Country

  885 S Waukeenah St, Monticello, FL 32344
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  Est $580,158 Not Listed For Sale

  210 Deer Run, Monticello, FL 32344

  • 3 Beds
  • 2.5 Baths
  • 2,700 Sq Ft
  • Built 1988

  210 Deer Run, Monticello, FL 32344

  Last Sold Summary

  • 17% Above List Price
  • $183/SF
  • 10 Days On Market

  Last Sold Price $494,911

  Last Listing Agent Jason Reese Solid Ground Real Estate Group
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  /13

  $65,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,216 Sq Ft

  1309 Cook Rd, Lamont, FL 32336

  Investor Special on 3 Acres in Monticello, FL! Opportunity awaits with this 3-acre property just 20 minutes from Tallahassee! Featuring a mobile home that will require significant renovation—taken down to the shell and rebuilt—or removal entirely, this has been priced accordingly for investors or buyers looking to start fresh. The existing home has experienced water damage to the flooring and

  Alicia Radtke All Realty Services

  1309 Cook Rd, Lamont, FL 32336
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  /42

  $529,900 Sold Apr 30, 2025

  273 Legacy Way, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,868 Sq Ft
  • Built 2017

  Last Sold Summary

  • $284/SF
  • 16 Days On Market

  Current Estimated Value $578,968

  Last Listing Agent Amber Renaud The Nova Group Realty

  273 Legacy Way, Monticello, FL 32344
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  Not Listed For Sale

  927 Quail Ln, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 2013

  927 Quail Ln, Monticello, FL 32344

  Last Sold Summary

  • $170/SF
  • 58 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Heather Cash Waypoint Properties
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  /3

  $415,500

  • Land
  • 22.13 Acres
  • $18,775 per Acre

  00 Boston Hwy, Monticello, FL 32344

  2 MILES FROM Monticello Courthouse! Bordering Jefferson County Country Club. 2 Parcels for total of 22.13 Acres adjacent to Jefferson County Golf Club and bordering Boston Hwy- 1028 ft. frontage - and Mamie Scott Drive. 2 Acres on Mamie Scott with 360' FRONTAGE AND has City Water/Electric Access and is actually within City Limits with zoning of RESIDENTIAL-MULTIFAMILY. Remaining property zoning

  Jennifer Ward Century 21 First Story

  00 Boston Hwy, Monticello, FL 32344
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  /36

  $110,000 Sold Jun 16, 2025

  955 E Pearl St, Monticello, FL 32344

  • 4 Beds
  • 2 Baths
  • 2,152 Sq Ft
  • Built 1920

  Last Sold Summary

  • 16% Above List Price
  • $51/SF
  • 57 Days On Market

  Current Estimated Value $216,855

  Last Listing Agent Lynette Sirmon All Realty Services

  955 E Pearl St, Monticello, FL 32344
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  Est $330,853 Not Listed For Sale

  275 Rudolph Ln, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,421 Sq Ft
  • Built 2015

  275 Rudolph Ln, Monticello, FL 32344

  Last Sold Summary

  • 16% Above List Price
  • $201/SF
  • 4 Days On Market

  Last Sold Price $285,000

  Last Listing Agent Corey Gray Keller Williams Town & Country
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  /13

  $65,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  40 Westview Ln, Monticello, FL 32344

  Don't judge this home by its exterior!! The outside siding shows significant deterioration, which is fully reflected in the price. However, once inside, you'll find a livable interior that's far more functional than first impressions suggest. This double-wide is currently occupied and offers ;an opportunity for a buyer willing to look past the exterior and focus on the potential within. Not

  Alicia Radtke All Realty Services

  40 Westview Ln, Monticello, FL 32344
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  /14

  $230,000 Sold Apr 24, 2025

  523 Silver Lake Rd, Monticello, FL 32344

  • 2 Beds
  • 1 Bath
  • 1,316 Sq Ft
  • Built 1970

  Last Sold Summary

  • 8% Below List Price
  • $175/SF
  • 26 Days On Market

  Current Estimated Value $261,850

  Last Listing Agent Brian Bachman Kelly & Kelly Properties, Inc

  523 Silver Lake Rd, Monticello, FL 32344

Showing Results 201 - 240, Page 6 of 18