Jefferson County, FL Homes

• 

  

  

  /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 $565,961

  Last Listing Agent Brett Miller Legacy Pro Real Estate Group

  44 S Ojibwa Rd, Monticello, FL 32344
• 

  

  

  /16

  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
• 

  

  

  /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
• 

  

  

  /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 CONSULTANTS TO HOMEBUI

  000 Barnes Rd, Monticello, FL 32344
• 

  

  

  /39

  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

  • 10 Days On Market
• 

  

  /4

  $299,000

  • Land
  • 85.69 Acres
  • $3,489 per Acre

  0 Big Joe Rd Unit 399642, Monticello, FL 32344

  85.69 acres of land located on Big Joe Road in Monticello. Zoned Agri-05, this versatile property offers a unique blend of privacy, natural beauty, and development potential. Featuring a mix of wetlands and usable upland areas, the property may be ideal for a variety of uses including recreational development, camping, hunting retreat, RV park, event venue, outdoor hospitality concepts, or future

  Lynnaye Boyd Resilience Realty

  0 Big Joe Rd Unit 399642, Monticello, FL 32344
• 

  

  /57

  $180,000

  Sold Apr 29, 2026

  265 W Seminole Ave, Monticello, FL 32344

  • 2 Beds
  • 1 Bath
  • 1,741 Sq Ft
  • Built 1959

  Last Sold Summary

  • 22% Below List Price
  • $103/SF
  • 38 Days On Market

  Current Estimated Value $196,824

  Last Listing Agent Karen Gillispie Keller Williams Town & Country

  265 W Seminole Ave, Monticello, FL 32344
• 

  

  /41

  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

  • 58 Days On Market
• 

  

  /34

  $274,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 2,070 Sq Ft

  450 W Madison St, Monticello, FL 32344

  Nestled beneath a canopy of mature trees just minutes from downtown Monticello, 450 W. Madison Street is a charming home filled with character, warmth, and inviting indoor-outdoor living. Located in a golf cart-friendly community, this property offers the perfect blend of small-town charm, everyday convenience, and the relaxed pace that makes historic Monticello so special. From the brick walkway

  Michael Manuel CONSULTANTS TO HOMEBUI

  450 W Madison St, Monticello, FL 32344
• 

  

  /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
• 

  

  /36

  Est $309,167

  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

  • 4 Days On Market
• 

  

  /8

  $25,000

  $4K PRICE DROP Under Contract

  • Land
  • 14,374 Sq Ft
  • $75,758 per Acre

  923 King St, Monticello, FL 32344

  Exceptional cleared corner lot with a concrete slab already in place—ready for your vision! City water and sewer connections are available, with electric at the road. Conveniently located just minutes from downtown Monticello. Motivated Sellers!

  Alicia Radtke All Realty Services

  923 King St, Monticello, FL 32344
• 

  

  /48

  $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
• 

  

  /11

  Est $109,196

  Not Listed For Sale

  161 Meadow Dr, Monticello, FL 32344

  • 2 Beds
  • Built 1980

  161 Meadow Dr, Monticello, FL 32344

  Last Sold Summary

  • 67 Days On Market
• 

  

  /12

  $185,000

  • 3 Beds
  • 1 Bath
  • 1,312 Sq Ft

  670 Poplar St, Monticello, FL 32344

  Solid 3/1 SFR brick less than a mile from downtown Monticello! This quaint 1,312 sq ft home sits under a metal roof and only requires your vision and a little TLC to become a superb starter home or investment opportunity. It also includes an additional lot.

  Spencer Conner Keller Williams Town & Country

  670 Poplar St, Monticello, FL 32344
• 

  

  /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 $217,690

  Last Listing Agent Lynette Sirmon All Realty Services

  955 E Pearl St, Monticello, FL 32344
• 

  

  /3

  Est $111,928

  Not Listed For Sale

  393 E Glenn Rd, Monticello, FL 32344

  • 30000 Beds
  • Built 1972

  393 E Glenn Rd, Monticello, FL 32344

  Last Sold Summary

  • 40 Days On Market
• 

  

  /31

  $275,000

  $10K PRICE DROP Under Contract

  • 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
• 

  /2

  $35,000

  Sold Dec 03, 2025

  lot 15 & 16 Partridge Ln, Monticello, FL 32344

  • Land
  • 1 Acre
  • $35,000 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Ashley Knowles The Naumann Group Real Estate

  lot 15 & 16 Partridge Ln, Monticello, FL 32344
• 

  

  /34

  Est $226,253

  Not Listed For Sale

  1060 S Mulberry St, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2006

  1060 S Mulberry St, Monticello, FL 32344

  Last Sold Summary

  • 153 Days On Market
• 

  

  /70

  $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
• 

  

  /61

  $545,000

  Sold May 13, 2026

  2184 Tram Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1998

  Last Sold Summary

  • $324/SF
  • 17 Days On Market

  Current Estimated Value $510,844

  Last Listing Agent Penny Herman Penny Herman Realty

  2184 Tram Rd, Monticello, FL 32344
• 

  

  /42

  Not Listed For Sale

  995 Taylor Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 2,432 Sq Ft
  • Built 2020

  995 Taylor Rd, Monticello, FL 32344

  Last Sold Summary

  • 67 Days On Market
• 

  

  /4

  $550,000

  • 6,024 Sq Ft

  535 Hagan St, Monticello, FL 32344

  Rare Investor Opportunity: 7-Unit Residential Complex for Sale Don't miss this fantastic investment opportunity! This well-maintained 7-unit complex features: Six 3-bedroom, 1-bathroom units One 2-bedroom, 1-bathroom unit Walking distance to downtown – perfect for tenants seeking convenience Corner lot location with excellent visibility Designated parking spots for each unit 2023 Roof Whether

  Caleb Stephens Silo Hill Properties

  535 Hagan St, Monticello, FL 32344
• 

  

  /5

  $260,000

  Sold Aug 29, 2025

  0 Taylor Rd Unit 378633, Monticello, FL 32344

  • Land
  • 12.46 Acres
  • $20,867 per Acre

  Last Sold Summary

  • 5% Below List Price
  • 296 Days On Market

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc

  0 Taylor Rd Unit 378633, Monticello, FL 32344
• 

  

  /27

  Est $273,499

  Not Listed For Sale

  84 Hillside Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,648 Sq Ft
  • Built 1999

  84 Hillside Rd, Monticello, FL 32344

  Last Sold Summary

  • 49 Days On Market
• 

  

  /9

  $198,000

  • 3 Beds
  • 1 Bath
  • 1,366 Sq Ft

  870 Shady Ln, Monticello, FL 32344

  Welcome to 870 Shady Lane in Monticello, Florida—a charming property that offers the perfect blend of privacy, space, and small-town appeal. Nestled on a quiet, tree-lined street, this home provides a peaceful retreat while still being conveniently close to the historic downtown district, local shops, and dining. Surrounded by mature trees and natural beauty, the property offers a serene setting

  Angela Graham Hamilton Realty Advisors LLC

  870 Shady Ln, Monticello, FL 32344
• 

  

  /55

  $1,035,000

  Sold Oct 15, 2025

  1165 Dills Rd, Monticello, FL 32344

  • 5 Beds
  • 5.5 Baths
  • 4,700 Sq Ft
  • Built 2002

  Last Sold Summary

  • 6% Below List Price
  • $220/SF
  • 54 Days On Market

  Current Estimated Value $1,044,892

  Last Listing Agent Callie Rhoads The Naumann Group Real Estate

  1165 Dills Rd, Monticello, FL 32344
• 

  

  /13

  Est $144,256

  Not Listed For Sale

  56 Ward Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 2,320 Sq Ft
  • Built 1979

  56 Ward Rd, Monticello, FL 32344

  Last Sold Summary

  • 56 Days On Market
• 

  

  /12

  $128,900

  Under Contract

  • Land
  • 6.86 Acres
  • $18,790 per Acre

  1407 S Jefferson St, Monticello, FL 32344

  This property presents a strong commercial opportunity along the highly visible Hwy 19 corridor. The property consists of approximately 6.8± acres of B-2 Highway Commercial land with over 400± feet of frontage on Highway 19, offering excellent exposure and accessibility in a growing retail and service trade area.The site includes an approved development plan; however, the only designated

  Sam Ameen Xcellence

  1407 S Jefferson St, Monticello, FL 32344
• 

  

  /29

  $273,695

  Sold Nov 26, 2025

  9497 Gamble Rd, Monticello, FL 32344

  • 2 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1995

  Last Sold Summary

  • 7% Below List Price
  • $195/SF
  • 128 Days On Market

  Last Listing Agent Trevor Ann Clark Keller Williams Town & Country

  9497 Gamble Rd, Monticello, FL 32344
• 

  

  /5

  Not Listed For Sale

  xx Landfill Rd, Monticello, FL 32344

  xx Landfill Rd, Monticello, FL 32344

  Last Sold Summary

  • 16 Days On Market
• 

  

  /13

  $65,000

  $5K PRICE DROP

  • 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
• 

  /2

  $110,000

  Sold Dec 19, 2025

  000 Taylor Rd, Monticello, FL 32344

  • Land
  • 5.17 Acres
  • $21,277 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent D. Scott Kilgore Superior Realty Group LLC

  000 Taylor Rd, Monticello, FL 32344
• 

  

  /4

  Est $106,664

  Not Listed For Sale

  395 W High St, Monticello, FL 32344

  • 3 Beds
  • 1 Bath
  • 825 Sq Ft
  • Built 1958

  395 W High St, Monticello, FL 32344

  Last Sold Summary

  • 12 Days On Market
• 

  

  /19

  $395,000

  $104K PRICE DROP

  • Land
  • 3.2 Acres
  • $123,438 per Acre

  XX Shiver Rd, Monticello, FL 32345

  Beautiful High lot at corner of Hwy 19, Shiver and Lake Rd. This listing is compilation of 3 contiguous parcels : (19-2N-5E-0140-0000-0300 and 19-2N-5E-0000-0210-0000 and 19-2N-5E-0140-0000-0170). for a total of 3.25 acres . PRIME location for multi-family, office, mixed use commercial business that needs visibility and ease of access. Utilities available- Water access to main line is Under Hwy

  Jennifer Ward Century 21 First Story

  XX Shiver Rd, Monticello, FL 32345
• 

  

  /33

  $250,000

  Sold Oct 15, 2025

  186 Deerhaven Ln, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,006 Sq Ft
  • Built 1976

  Last Sold Summary

  • $249/SF
  • 27 Days On Market

  Current Estimated Value $251,940

  Last Listing Agent Richard Snow Ketcham Realty Group, Inc.

  186 Deerhaven Ln, Monticello, FL 32344
• 

  

  /42

  Est $677,181

  Not Listed For Sale

  649 Waukeenah Plantation Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • Built 2005

  649 Waukeenah Plantation Rd, Monticello, FL 32344

  Last Sold Summary

  • 39 Days On Market
• 

  

  /39

  $165,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,050 Sq Ft

  534 N Barber Hill, Lamont, FL 32336

  This all brick three bedroom two bath home on an acre of land features high ceilings, luxury vinyl plank, carpet and tile, nice sized kitchen, den with fireplace, and additional living space that could be used as an office with its own side entrance. Plenty of storage at this home with and carport space. Make this your home today with some TLC.

  Othell Broger Broger Real Estate Services

  534 N Barber Hill, Lamont, FL 32336
• 

  

  /64

  $425,000

  Sold Dec 15, 2025

  595 Crooked Creek Ln, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,919 Sq Ft
  • Built 2022

  Last Sold Summary

  • $221/SF
  • 61 Days On Market

  Current Estimated Value $425,783

  Last Listing Agent Chance Shutes Keller Williams Town & Country

  595 Crooked Creek Ln, Monticello, FL 32344

Showing Results 241 - 280, Page 7 of 18