Jefferson County, FL Homes

• 

  

  

  /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

  Last Listing Agent Caleb Stephens Silo Hill Properties

  375 Maple St, Monticello, FL 32344
• 

  

  

  /5

  Not Listed For Sale

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

  271 Tecumseh Rd, Monticello, FL 32344

  271 Tecumseh Rd, Monticello, FL 32344
• 

  

  

  /26

  $380,000

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft

  298 W 12th Dr, Greenville, FL 32331

  From the moment you pass through the gated entrance and drive under the canopy of hardwoods and pines, you’ll feel the privacy and peacefulness that makes this 10.93-acre homestead so special. Beautifully maintained and set on two parcels, this property includes a solid 3BR/2BA block home, a detached garage/shop with a full bath, and a wired pole barn. The block-construction home is built to

  Jay Finlayson Finlayson Realty Inc.

  298 W 12th Dr, Greenville, FL 32331
• 

  

  

  /7

  $95,000 Sold Aug 01, 2025

  0 Taylor Rd Unit 384618, Monticello, FL 32344

  • Land
  • 5.17 Acres
  • $18,375 per Acre

  Last Sold Summary

  • 21% Below List Price
  • 102 Days On Market

  Last Listing Agent Kevin Davis The Naumann Group Real Estate

  0 Taylor Rd Unit 384618, Monticello, FL 32344
• 

  

  

  /5

  Not Listed For Sale

  0 W Osprey Ln, Monticello, FL 32344

  0 W Osprey Ln, Monticello, FL 32344
• 

  

  /31

  $439,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  285 Mallard Ln, Monticello, FL 32344

  One or more pictures have been virtually enhanced *Jefferson County peaceful country living with a waterfront backdrop! Built in 2008, this well maintained 3 bedroom, 2 bath home sits on 4.89 beautifully (mostly cleared) acres offering privacy and natural beauty backing directly up to Lloyd Lake- perfect for relaxing evenings with scenic views. Pretty rocking chair front porch as well as a

  Shelley Duke Red Bird Realty

  285 Mallard Ln, 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 $219,787

  Last Listing Agent Kenneth Ayers Primesouth Fezler, Russell and

  1400 Gamble Rd, Monticello, FL 32344
• 

  

  /16

  Not Listed For Sale

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

  157 White Oak Dr, Monticello, FL 32344

  157 White Oak Dr, Monticello, FL 32344
• 

  

  /11

  $22,500

  • Land
  • 2 Acres
  • $11,250 per Acre

  0 Flatwoods, Monticello, FL 32344

  Land for Sale – Flatwoods, FL 32344. Size: 2.0 Acres. Location: Flatwoods Road, Monticello, Florida 32344. Property Highlights: Buildable lot with plenty of space; Power available on the road; 411.75 feet of road frontage; Peaceful rural setting surrounded by large parcels; No HOA – flexible use for site-built or modular homes. About 40 minutes to Tallahassee. Ideal for a private

  Andrey Rossin CASH FLOW IN MIAMI REALTY

  0 Flatwoods, Monticello, FL 32344
• 

  

  /22

  $295,000 Sold Jan 17, 2025

  390 Elliot Dr, Monticello, FL 32344

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

  Last Sold Summary

  • 9% Below List Price
  • $218/SF
  • 28 Days On Market

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

  390 Elliot Dr, Monticello, FL 32344
• 

  

  /39

  Est $577,644 Not Listed For Sale

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

  210 Deer Run, Monticello, FL 32344

  210 Deer Run, Monticello, FL 32344
• 

  

  /70

  $750,000

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  1627 Lloyd Creek Rd, Monticello, FL 32344

  Enjoy the gorgeous water views from the porch of this like-new, 2022 built home! A gated driveway leads to your 5 acre parcel on a beautiful 10 acre spring-fed lake. 6 ft windows and 8x8 sliding doors allow the open living, dining, and kitchen areas to view the sunny outdoors. Kitchen features a large island with seating area, stainless appliances, gas stove, and fridge with dual ice maker.

  Nan Greynolds The Naumann Group Real Estate

  1627 Lloyd Creek Rd, 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
• 

  

  /41

  Not Listed For Sale

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

  927 Quail Ln, Monticello, FL 32344

  927 Quail Ln, Monticello, FL 32344
• 

  

  /16

  $65,000

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft

  980 Mays St, Monticello, FL 32344

  Probate proceedings underway. Cannot close until court approval. Concrete Block 2/1 Home less than a mile from downtown Monticello! This quaint 888sqft home sits under a metal roof and only requires your vision and a little effort to become a superb starter home or investment opportunity. Property is fully fenced and on city utilities. Room measurements are approximate

  Ben Marinelli All Realty Services

  980 Mays St, Monticello, FL 32344
• 

  

  /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
• 

  

  /36

  Est $339,986 Not Listed For Sale

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

  275 Rudolph Ln, Monticello, FL 32344

  275 Rudolph Ln, Monticello, FL 32344
• 

  

  /11

  $119,900

  • 1 Bed
  • 1 Bath
  • 1,064 Sq Ft

  4685 Waukeenah Hwy, Monticello, FL 32344

  Check out this one-of-a-kind property that offers versatility, privacy and potential income rental. As you pull in, you're welcomed by a rock gravel driveway leading to an enclosed barn that houses a thoughtfully designed studio apartment and garage space. Inside the barn, the studio offers a space for fully time living, weekend stays or short-term rental use. Outside, the property truly shines

  E. Bradley Vollertsen Advanced Real Estate Sales

  4685 Waukeenah Hwy, 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

  Last Listing Agent Catherine Hope All Realty Services

  282 Long Leaf Dr, Monticello, FL 32344
• 

  

  /11

  Est $100,529 Not Listed For Sale

  • 2 Beds

  161 Meadow Dr, Monticello, FL 32344

  161 Meadow Dr, Monticello, FL 32344
• 

  

  /54

  $169,000

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

  12447 Gamble Rd, Monticello, FL 32344

  This 2 bedroom, 2 bathroom home offers 1,440 sqft of living space on a full acre in Wacissa, just 2 minutes from the Wacissa River headwaters and boat launch. It’s an ideal spot for a full-time residence or could serve as a hunting or fishing lodge with easy access to the outdoors. Spend your weekends swimming at the sandy beach, kayaking the clear spring-fed waters, or paddleboarding through

  Catherine Hope All Realty Services

  12447 Gamble Rd, Monticello, FL 32344
• 

  

  /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
• 

  

  /3

  Est $118,388 Not Listed For Sale

  • 30000 Beds

  393 E Glenn Rd, Monticello, FL 32344

  393 E Glenn Rd, Monticello, FL 32344
• 

  

  /7

  $150,000

  • Land
  • 10 Acres
  • $15,000 per Acre

  576 Cox Rd, Monticello, FL 32344

  Discover a fantastic future homesite on a secluded 10-acre parcel in northern Jefferson County, Florida! Accessed via a 15-foot-wide easement off a private road, the property opens up to a beautiful, private clearing ideal for building your dream home. The land features a mix of large pines, hardwoods, and magnolias, creating a serene, natural setting. Key utilities are already in place or

  Gabriela Sacco All Realty Services

  576 Cox Rd, Monticello, FL 32344
• 

  

  /29

  $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
• 

  

  /34

  Est $271,964 Not Listed For Sale

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

  1060 S Mulberry St, Monticello, FL 32344

  1060 S Mulberry St, Monticello, FL 32344
• 

  

  /59

  $537,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,371 Sq Ft

  1923 Whitehouse Rd, Monticello, FL 32344

  Convenient Country Living With Room (6 acres) to Roam and a Fabulous Home! Welcome to this light, bright, and well-maintained 4BR/3BA 2008 custom-built home (metal stud construction and extra insulation make this home extremely energy efficient) just minutes from I-10 near the edge of Eastern Leon County. The inviting home features an open floorplan and a large kitchen with an sizeable island

  Bonnie Fowler Armor Realty, Inc

  1923 Whitehouse Rd, Monticello, FL 32344
• 

  

  /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

  Last Listing Agent Brett Miller Legacy Pro Real Estate Group

  44 S Ojibwa Rd, Monticello, FL 32344
• 

  

  /27

  Est $231,938 Not Listed For Sale

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

  84 Hillside Rd, Monticello, FL 32344

  84 Hillside Rd, Monticello, FL 32344
• 

  

  /24

  $99,000 Under Contract

  • Land
  • 5.03 Acres
  • $19,682 per Acre

  0 Johnny Unit 392570, Lamont, FL 32336

  Discover the perfect blend of privacy and convenience with this beautiful acreage backing up to the renowned Pines of Avalon Plantation. Just minutes from Monticello and I-10, offering easy access to Tallahassee, the high and dry lot provides a stunning natural backdrop with abundant wildlife. Mature timber covers the majority of the land (mostly long-leaf pines) creating a serene setting and a

  Michael Reavis The Naumann Group Real Estate

  0 Johnny Unit 392570, 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 Armor Realty, Inc

  000 Barnes Rd, Monticello, FL 32344
• 

  

  /13

  Est $174,809 Not Listed For Sale

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

  56 Ward Rd, Monticello, FL 32344

  56 Ward Rd, Monticello, FL 32344
• 

  

  /43

  $249,900 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,044 Sq Ft

  300 Cedar St, Monticello, FL 32344

  Under Contract with multiple offers ~ Huge Price Improvement, now $249,900 ~ Welcome to 300 Cedar Street ~ Located a stone's throw from Monticello's charming downtown, yet quiet & private ~ Relax in a rocking chair & enjoy sitting on your HUGE 64x8 screened in porch that runs the entire length of the back of the home & overlooks the serene 1.5 acre lot ~ Built in 1958, this single story home is a

  Jonathan Rigsby Spotlight Real Estate

  300 Cedar 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 The Nova Group Realty

  149 Coopers Pond Rd, Monticello, FL 32344
• 

  

  /5

  Not Listed For Sale

  xx Landfill Rd, Monticello, FL 32344

  xx Landfill Rd, Monticello, FL 32344
• 

  

  /70

  $1,175,000

  • 5 Beds
  • 3.5 Baths
  • 5,590 Sq Ft

  237 Valley View Ct, Monticello, FL 32344

  This is an actual sunset over a 15 minute period in mid-October. Experience gorgeous sunsets and serene living at this exceptional single-story, multi-home estate on 15 high-and-dry acres in beautiful Valley View Estates, straddling the Leon and Jefferson County line. **With a NEW Roof prior to closing, the custom-built main residence (~4,000 sq. ft.) offers 12-foot ceilings throughout, an

  Kelly Vinson Keller Williams Town & Country

  237 Valley View Ct, Monticello, FL 32344
• 

  

  /27

  $625,000 Sold Jan 31, 2025

  136 Sutton, Monticello, FL 32344

  • 4 Beds
  • 3 Baths
  • 2,620 Sq Ft
  • Built 2023

  Last Sold Summary

  • 24% Below List Price
  • $239/SF
  • 162 Days On Market

  Current Estimated Value $666,517

  Last Listing Agent Pamela Jordan-Williams Superior Realty Group LLC

  136 Sutton, Monticello, FL 32344
• 

  

  /4

  Est $100,628 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 825 Sq Ft

  395 W High St, Monticello, FL 32344

  395 W High St, Monticello, FL 32344
• 

  

  /49

  $629,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 3,214 Sq Ft

  150 N Ojibwa Rd, Monticello, FL 32344

  One or more photo(s) has been virtually staged. Tranquil 5.1 acre retreat nestled deep in a pecan grove just outside Monticello, Florida has it all. This recently remodeled 3BR/2BA home offers space, privacy and flexibility in a rural setting only 40 minutes from the heart of Tallahassee. Take advantage of everything Tallahassee offers while paying lower Jefferson County taxes. The pecan trees

  Hettie Spooner Hill Spooner & Elliott Inc

  150 N Ojibwa Rd, Monticello, FL 32344
• 

  

  /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 $214,894

  Last Listing Agent Catherine Hope All Realty Services

  370 Brown Rd, Lamont, FL 32336

Showing Results 161 - 200, Page 5 of 18