Jefferson County, FL Homes

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  /35

  $325,000

  Sold Nov 25, 2025

  1530 Sweetbay Ct, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,370 Sq Ft
  • Built 2021

  Last Sold Summary

  • $237/SF
  • 58 Days On Market

  Current Estimated Value $323,294

  Last Listing Agent Chance Shutes Keller Williams Town & Country

  1530 Sweetbay Ct, Monticello, FL 32344
• 

  

  

  /31

  Not Listed For Sale

  112 Rudolph Ln, Monticello, FL 32344

  • 4 Beds
  • 2 Baths
  • 2,112 Sq Ft
  • Built 2022

  112 Rudolph Ln, Monticello, FL 32344

  Last Sold Summary

  • 68 Days On Market

  Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc
• 

  

  

  /11

  $45,000

  $5K PRICE DROP

  • 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
• 

  

  

  /17

  $337,500

  Sold Jun 26, 2026

  406 Robin Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,502 Sq Ft
  • Built 1976

  Last Sold Summary

  • 3% Below List Price
  • $225/SF
  • 5 Days On Market

  Current Estimated Value $318,644

  Last Listing Agent Caleb Stephens Silo Hill Properties

  406 Robin Rd, Monticello, FL 32344
• 

  

  

  /4

  Not Listed For Sale

  TBD Blackberry Tr, Monticello, FL 32344

  TBD Blackberry Tr, Monticello, FL 32344

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc
• 

  

  /5

  $775,000

  New Construction Under Contract

  • 4 Beds
  • 3 Baths
  • 2,377 Sq Ft

  693 Tally Hills Dr, Monticello, FL 32344

  New Construction. Images are renderings. 4-bedroom, 3-bath home coming soon in Tally Hills Estates. Construction has started on this beautifully designed, new construction home set on over 5 acres.

  Shelley Poppell Clover Key Realty

  693 Tally Hills Dr, Monticello, FL 32344
• 

  

  /3

  $244,900

  Sold Mar 21, 2026

  655 N Cherry St, Monticello, FL 32344

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 2026

  Last Sold Summary

  • $224/SF
  • 35 Days On Market

  Last Listing Agent Steve Walker Steve C. Walker Realty, LLC

  655 N Cherry St, Monticello, FL 32344
• 

  

  /4

  Not Listed For Sale

  XXXX St Augustine Rd Parcel #2, Monticello, FL 32344

  XXXX St Augustine Rd Parcel #2, Monticello, FL 32344

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Hines Boyd FL-GA Realty & Auction
• 

  

  /38

  $90,000

  $10K PRICE DROP Under Contract

  • 3 Beds
  • 1 Bath
  • 1,864 Sq Ft

  340 S Waukeenah St, Monticello, FL 32344

  They don’t build them like they used to! This historic 1900 home located in downtown Monticello sits on nearly a half-acre lot and is full of timeless character waiting to be restored. Featuring original hardwood floors throughout most of the home, beadboard walls, 9+ foot ceilings, and original glass windows, this property offers the charm and craftsmanship so many buyers desire. Spacious

  Alicia Radtke All Realty Services

  340 S Waukeenah St, Monticello, FL 32344
• 

  

  /27

  $210,000

  Sold Oct 20, 2025

  140 E Buckhorn Trail, Greenville, FL 32331

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 2004

  Last Sold Summary

  • 16% Below List Price
  • $135/SF
  • 101 Days On Market

  Current Estimated Value $218,467

  Last Listing Agent Christopher Worth Keller Williams Town & Country

  140 E Buckhorn Trail, Greenville, FL 32331
• 

  

  /20

  Not Listed For Sale

  VACANT W 3rd Way, Greenville, FL 32331

  VACANT W 3rd Way, Greenville, FL 32331

  Last Sold Summary

  • 103 Days On Market

  Last Listing Agent Catherine Hope All Realty Services
• 

  

  /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
• 

  

  /14

  $168,100

  Sold Nov 17, 2025

  375 Maple St, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft
  • Built 1920

  Last Sold Summary

  • 11% Below List Price
  • $98/SF
  • 70 Days On Market

  Current Estimated Value $171,310

  Last Listing Agent Caleb Stephens Silo Hill Properties

  375 Maple St, Monticello, FL 32344
• 

  

  /11

  Not Listed For Sale

  XXX Parcel #3 St Augustine Rd, Monticello, FL 32344

  XXX Parcel #3 St Augustine Rd, Monticello, FL 32344

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Hines Boyd FL-GA Realty & Auction
• 

  

  /43

  $375,000

  Under Contract

  • 3 Beds
  • 3 Baths
  • 2,706 Sq Ft

  339 Silver Lake Rd, Monticello, FL 32344

  Large home on 5 acres mostly pasture~very peaceful setting~BRAND NEW LVP~Open concept with vaulted ceilings~large oaks~perfect pasture for horses or cattle~No HOA~

  Steve Walker Steve C. Walker Realty, LLC

  339 Silver Lake Rd, Monticello, FL 32344
• 

  

  /10

  $220,000

  Sold Aug 26, 2025

  1400 Gamble Rd, Monticello, FL 32344

  • Land
  • 7 Acres
  • $31,429 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 119 Days On Market

  Current Estimated Value $210,458

  Last Listing Agent Kenneth Ayers Primesouth Fezler, Russell and

  1400 Gamble Rd, Monticello, FL 32344
• 

  

  /11

  Not Listed For Sale

  xxx St Augustine Parcel #4 Rd, Monticello, FL 32344

  xxx St Augustine Parcel #4 Rd, Monticello, FL 32344

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Hines Boyd FL-GA Realty & Auction
• 

  

  /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
• 

  

  /13

  $62,500

  Sold Mar 31, 2026

  TBD Smokehouse Farms Dr, Greenville, FL 32331

  • Land
  • 5.01 Acres
  • $12,475 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 71 Days On Market

  Last Listing Agent Lynette Sirmon All Realty Services

  TBD Smokehouse Farms Dr, Greenville, FL 32331
• 

  

  /40

  Est $550,674

  Not Listed For Sale

  9255 Gamble Rd, Monticello, FL 32344

  • 2 Beds
  • 3 Baths
  • 1,833 Sq Ft
  • Built 1970

  9255 Gamble Rd, Monticello, FL 32344

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Alicia Radtke All Realty Services
• 

  /2

  $319,900

  New Construction $2K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,550 Sq Ft

  300 Bowman St, Monticello, FL 32344

  Recently built home featuring spacious open floor plan. Kitchen has raised cabinets, granite counters, stainless steel appliances, large island with plenty of seating & a pantry....overlooks spacious family area with plenty of room for large gatherings, plus separate dining space. First floor also offers 1/2 bath and large storage area under stairs. Upstairs you are greeted with open reading area

  Steve Walker Steve C. Walker Realty, LLC

  300 Bowman St, Monticello, FL 32344
• 

  

  /22

  $185,000

  Sold Jun 05, 2026

  165 N Water St, Monticello, FL 32344

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • Built 1930

  Last Sold Summary

  • $227/SF
  • 4 Days On Market

  Current Estimated Value $182,695

  Last Listing Agent Sandy Ferrera All County Suncoast Property

  165 N Water St, Monticello, FL 32344
• 

  

  /4

  Not Listed For Sale

  XXX Shiver, Monticello, FL 32344

  XXX Shiver, Monticello, FL 32344

  Last Sold Summary

  • 204 Days On Market

  Last Listing Agent Hines Boyd FL-GA Realty & Auction
• 

  

  /69

  $800,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,653 Sq Ft

  728 Turney Anderson Rd, Monticello, FL 32344

  Some homes are built. Others are curated. This extraordinary custom residence was thoughtfully constructed in 2006 to capture the timeless elegance and craftsmanship of a grand estate from the early 1900s, blending historic charm with modern convenience on five picturesque acres shaded by mature pecan trees. From the moment you arrive via the long paved driveway, you'll be captivated by the

  Tanner Pafford Keller Williams Town & Country

  728 Turney Anderson Rd, Monticello, FL 32344
• 

  

  /5

  $49,000

  Sold Feb 16, 2026

  4618 E Capps Hwy, Lamont, FL 32336

  • 4 Beds
  • 1 Bath
  • 1,232 Sq Ft
  • Built 1940

  Last Sold Summary

  • 25% Below List Price
  • $40/SF
  • 247 Days On Market

  Current Estimated Value $78,114

  Last Listing Agent Nelda Parker-Pace Sawgrass Realty, LLC

  4618 E Capps Hwy, Lamont, FL 32336
• 

  

  /24

  Not Listed For Sale

  00 Valley View Rd, Monticello, FL 32344

  00 Valley View Rd, Monticello, FL 32344

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Brenna Kelly-Ward Kelly & Kelly Properties, Inc
• 

  

  /46

  $337,000

  $11K PRICE DROP Under Contract

  • 4 Beds
  • 2 Baths
  • 2,162 Sq Ft

  4081 Gamble Rd, Monticello, FL 32344

  Escape to your own private 5-acre retreat! A long, secluded driveway leads to this charming cottage-style 4-bedroom, 2-bath home surrounded by the natural beauty of North Florida. Enjoy the peace and privacy you've been dreaming of with no HOA and no flood insurance required. The thoughtfully designed floor plan features a spacious primary suite and two additional bedrooms on the main level,

  Alisa McMahon Bluewater Realty Group

  4081 Gamble Rd, Monticello, FL 32344
• 

  

  /42

  $165,000

  Sold Feb 27, 2026

  2436 N Jefferson Hwy, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 2,390 Sq Ft
  • Built 1951

  Last Sold Summary

  • 38% Below List Price
  • $69/SF
  • 285 Days On Market

  Current Estimated Value $236,437

  Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

  2436 N Jefferson Hwy, Monticello, FL 32344
• 

  

  /17

  Not Listed For Sale

  188 Fallow Rd, Lamont, FL 32336

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft
  • Built 2005

  188 Fallow Rd, Lamont, FL 32336

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Brian Bachman Kelly & Kelly Properties, Inc
• 

  

  /3

  $39,900

  • Land
  • 1.91 Acres
  • $20,890 per Acre

  76 Barnes Rd, Monticello, FL 32344

  Discover the perfect spot to build your dream home or weekend getaway on this 1.91-acre property in Monticello! Featuring paved road frontage, a partially cleared homesite, and plenty of room to enjoy the surrounding natural beauty, this property offers the ideal balance of privacy and convenience. Located with easy access to both Monticello, FL and Thomasville, GA, you’ll enjoy peaceful country

  Crystal Bochnia Madison Realty Group, LLC

  76 Barnes Rd, Monticello, FL 32344
• 

  

  /14

  $26,000

  Sold Jan 29, 2026

  3C Hanger Ln, Greenville, FL 32331

  • Land
  • 3,920 Sq Ft
  • $288,889 per Acre

  Last Sold Summary

  • 33% Below List Price
  • 172 Days On Market

  Last Listing Agent Esther Warrendorf Canopy Road Realty

  3C Hanger Ln, Greenville, FL 32331
• 

  

  /8

  Not Listed For Sale

  0 Bassett Dairy Rd Unit 373105, Monticello, FL 32344

  0 Bassett Dairy Rd Unit 373105, Monticello, FL 32344

  Last Sold Summary

  • 284 Days On Market

  Last Listing Agent Brian Proctor NAI TALCOR Commercial
• 

  /2

  $95,000

  • Land
  • 2.22 Acres
  • $42,793 per Acre

  450 Oconee Ln, Monticello, FL 32344

  Vacant building lot; inside the city limits, city water and sewer are available, all high and dry; very nice neighborhood, no HOA.

  Steve Walker Steve C. Walker Realty, LLC

  450 Oconee Ln, Monticello, FL 32344
• 

  

  /3

  $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
• 

  

  /14

  Est $402,943

  Not Listed For Sale

  4131 Ashville Hwy, Monticello, FL 32344

  • 2 Beds
  • Built 1940

  4131 Ashville Hwy, Monticello, FL 32344

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Sarah Scott Coldwell Banker Hartung
• 

  

  /5

  $58,000

  • Land
  • 38,768 Sq Ft
  • $65,169 per Acre

  0 Spring Hollow Dr, Monticello, FL 32344

  Don't miss this exceptional 0.89-acre homesite in the Desirable Cooper's Pond community. This lot offers the perfect opportunity to create your dream home in a well-established neighborhood known for its attractive surroundings and welcoming atmosphere. Enjoy the convenience of being just minutes from town, with easy access to shopping, dining, schools, and everday amenities while still

  Ellen Fokes Armor Realty, Inc

  0 Spring Hollow Dr, Monticello, FL 32344
• 

  

  /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
• 

  /2

  Not Listed For Sale

  B Salt Rd, Monticello, FL 32344

  B Salt Rd, Monticello, FL 32344

  Last Sold Summary

  • 86 Days On Market

  Last Listing Agent Sherry Shaheen ENGEL & VOLKERS GAINESVILLE
• 

  

  /12

  $179,900

  $5K PRICE DROP

  • 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
• 

  

  /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 $499,665

  Last Listing Agent Catherine Hope All Realty Services

  282 Long Leaf Dr, Monticello, FL 32344

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