Jefferson County, FL Homes

• 

  

  

  /26

  $69,900

  $14K PRICE DROP Under Contract

  • Land
  • 6.4 Acres
  • $10,922 per Acre

  XXX Hopson Rd, Monticello, FL 32344

  Owner Financing available with 20% down. Motivated Seller! Unique shaped parcel located in a serene rural area—perfect for building, recreation, or investment

  Shanna D'Attile Keller Williams Town & Country

  XXX Hopson Rd, 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
• 

  

  

  /36

  Est $319,543

  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

  Last Listing Agent Corey Gray Keller Williams Town & Country
• 

  

  

  /70

  $395,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,891 Sq Ft

  1637 N Jefferson Hwy, Monticello, FL 32344

  Awesome all brick 3 bedroom 2 bathroom home on 4 beautiful acres along North Jefferson Highway in Jefferson County, FL. Hardwood floors run throughout with tile in the kitchen and bathrooms. The kitchen offers solid wood cabinetry with soft-close drawers, updated appliances, and ample storage. Mature longleaf pines dot the property, which features a circular driveway and a 24x24 concrete pad with

  Catherine Hope All Realty Services

  1637 N Jefferson Hwy, 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 $1,036,986

  Last Listing Agent Callie Rhoads The Naumann Group Real Estate

  1165 Dills Rd, Monticello, FL 32344
• 

  

  /11

  Est $117,291

  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

  Last Listing Agent Thomas Jacobs Coldwell Banker Hartung
• 

  

  /37

  $62,800

  Under Contract

  • Land
  • 7.85 Acres
  • $8,000 per Acre

  XXX Neely Rd, Monticello, FL 32344

  The following parcels are included in the sale: 32-2N-6E-0000-0023-0000 & 32-2N-6E-0000-0024-0000 This beautiful, wooded property offers a diverse landscape that's ideal for recreation, hunting, or building your private retreat. Mature hardwoods and towering pines create a peaceful forest setting, while natural clearings provide excellent locations for a homesite, food plots, or camping. The

  Chris Cammarata Armor Realty, Inc

  XXX Neely Rd, Monticello, FL 32344
• 

  

  /57

  $545,000

  Sold Jul 15, 2026

  513 Creekside Ct, Monticello, FL 32344

  • 4 Beds
  • 3 Baths
  • 2,660 Sq Ft
  • Built 2016

  Last Sold Summary

  • 8% Below List Price
  • $205/SF
  • 23 Days On Market

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

  513 Creekside Ct, Monticello, FL 32344
• 

  

  /3

  Est $135,293

  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

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

  /2

  $85,000

  • Land
  • 19,602 Sq Ft
  • $188,889 per Acre

  Lot 11 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes BOTH Lot 11 & 24 directly behind it totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 11 E Washington 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
• 

  

  /34

  Est $245,373

  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

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

  /2

  $85,000

  • Land
  • 2.05 Acres
  • $41,463 per Acre

  Lot 25 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes 10 Lots- 25-35 (Survey) totaling 2.05 Acres.

  Liz Kuntz Keller Williams Town & Country

  Lot 25 E Washington St, 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
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  /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

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

  

  /46

  $450,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 2,239 Sq Ft

  254 Woodland Dr, Monticello, FL 32344

  Custom home on 4.29 private acres~split bedroom plan~separate dining room~rocking chair front porch~screened porch overlooking wooded backyard~fireplace~upstairs room could be office or playroom~huge 40x40 workshop~FIRST TIME ON THE MARKET

  Renee Smawley Steve C. Walker Realty, LLC

  254 Woodland Dr, Monticello, FL 32344
• 

  

  /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 $254,238

  Last Listing Agent Richard Snow Ketcham Realty Group, Inc.

  186 Deerhaven Ln, Monticello, FL 32344
• 

  

  /27

  Est $289,071

  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

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

  

  /13

  $584,350

  $19K PRICE INCREASE

  • Land
  • 30.97 Acres
  • $18,868 per Acre

  Vacant Attatulga Rd, Lamont, FL 32336

  Discover the perfect blend of privacy and convenience with this beautiful 30-acre wooded parcel in Jefferson County. With a mix of towering pines and hardwoods, a picturesque creek runs through the center of this property, adding to the natural beauty and charm of the land. Nestled between Attatulga Rd and WPA Rd, you are afforded dual road access from the North and South. Zoned Ag-5, there are

  Catherine Hope All Realty Services

  Vacant Attatulga Rd, 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 $437,388

  Last Listing Agent Chance Shutes Keller Williams Town & Country

  595 Crooked Creek Ln, Monticello, FL 32344
• 

  

  /13

  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

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

  

  /19

  $424,900

  New Construction $20K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,798 Sq Ft

  855 S Waukeenah St, Monticello, FL 32344

  Stunning New Construction recently built by Southern Construction. Centrally located in downtown Monticello, with mature landscaping, and plenty of room for the family. This 4 bed and 3 bath home features vinyl plank flooring, granite countertops, walk in tile shower and tub in master, upgraded trim package, and stainless appliances. Nice large back porch with deck, over looking the large

  Jared Parramore Coastwise Realty

  855 S Waukeenah St, Monticello, FL 32344
• 

  

  /36

  $127,000

  Sold Aug 29, 2025

  2265 Deerwood Blvd, Greenville, FL 32331

  • 4 Beds
  • 2 Baths
  • 2,280 Sq Ft
  • Built 2004

  Last Sold Summary

  • 18% Below List Price
  • $56/SF
  • 74 Days On Market

  Last Listing Agent Jessica Webb A Main Street Realty Co, LLC

  2265 Deerwood Blvd, Greenville, FL 32331
• 

  

  /5

  Not Listed For Sale

  xx Landfill Rd, Monticello, FL 32344

  xx Landfill Rd, Monticello, FL 32344

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Katie Hosford The Naumann Group Real Estate
• 

  

  /3

  $1,190,000

  • 4 Beds
  • 4 Baths
  • 3,043 Sq Ft

  4264 Safari Run, Tallahassee, FL 32309

  New construction, East side of town this 4 Bedroom 4 Bath home with office and private sitting in master this home is a luxury on 2/12 acres. completion in early Aug 2026

  Robert Paynter Keller Williams Town & Country

  4264 Safari Run, Tallahassee, FL 32309
• 

  

  /55

  $150,000

  Sold Mar 11, 2026

  1515 Tennessee Ave, Monticello, FL 32344

  • 2 Beds
  • 2 Baths
  • 1,096 Sq Ft
  • Built 1958

  Last Sold Summary

  • 19% Below List Price
  • $137/SF
  • 134 Days On Market

  Current Estimated Value $154,779

  Last Listing Agent Catherine Hope All Realty Services

  1515 Tennessee Ave, Monticello, FL 32344
• 

  

  /4

  Est $119,289

  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

  Last Listing Agent Ben Marinelli All Realty Services
• 

  /2

  $350,500

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft

  1565 Sweetbay Ct, Monticello, FL 32344

  This home is currently coming out of the permitting phase. New construction will start in the next week. Completion date should be approx 4 months or less. We will update the comments as the construction progresses. Picture is virtual. More to come as construction continues.

  Steve Walker Steve C. Walker Realty, LLC

  1565 Sweetbay Ct, Monticello, FL 32344
• 

  /2

  $95,000

  Sold Aug 03, 2026

  0 Shannon Rd Unit 402178, Monticello, FL 32344

  • Land
  • 11.47 Acres
  • $8,282 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 2 Days On Market

  Last Listing Agent Steven Koleno Beycome of Florida LLC

  0 Shannon Rd Unit 402178, Monticello, FL 32344
• 

  

  /42

  Est $694,603

  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

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

  

  /3

  $299,900

  New Construction Under Contract

  • 3 Beds
  • 2 Baths
  • 1,575 Sq Ft

  12180 Gamble Rd, Monticello, FL 32344

  New Construction currently being built by Southern Construction. Home should be completed in August 2026. Home is located in a great location in S. Jefferson County, close to the Wacissa River. Home features 3 beds and 2 baths, hardi siding, granite countertops with large kitchen island, open floor plan, and vinyl plank flooring in bedrooms and common area. Master bath features large walk-in tile

  Jared Parramore Coastwise Realty

  12180 Gamble Rd, Monticello, FL 32344
• 

  

  /19

  $389,500

  Sold Jan 12, 2026

  173 Deerfield Ln, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,865 Sq Ft
  • Built 2025

  Last Sold Summary

  • 9% Below List Price
  • $209/SF
  • 110 Days On Market

  Last Listing Agent Caleb Stephens Silo Hill Properties

  173 Deerfield Ln, Monticello, FL 32344
• 

  

  /18

  Not Listed For Sale

  0 Sweetfield Rd Unit MFRT3505054, Monticello, FL 32344

  0 Sweetfield Rd Unit MFRT3505054, Monticello, FL 32344

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Ursula Bell AMERICAN DREAM TEAM REAL ESTATE BROKERS INC
• 

  

  /22

  $164,900

  $110K PRICE DROP Under Contract

  • 4 Beds
  • 3 Baths
  • 2,553 Sq Ft

  34 W Hummingbird Ln, Monticello, FL 32344

  *Some photos may be virtually staged* New beautiful LVP flooring on mother in law suite side of the property and wdo repair underneath the new flooring!! So many options with this property!! It boasts 2 separate living spaces joined by a common family room. One side of the home has 1 bed and 1 bath, it's own kitchen and living space. The other side of the home has 3 bedrooms, 2 bathrooms and the

  Susan Gillespie Lord & Stanley Realty, Inc.

  34 W Hummingbird Ln, Monticello, FL 32344
• 

  

  /12

  $94,000

  Sold Jun 03, 2026

  1407 S Jefferson St, Monticello, FL 32344

  • Land
  • 6.86 Acres
  • $13,703 per Acre

  Last Sold Summary

  • 27% Below List Price
  • 11 Days On Market

  Last Listing Agent Sam Ameen Xcellence

  1407 S Jefferson St, Monticello, FL 32344
• 

  

  /42

  Not Listed For Sale

  21 Mire Ct, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,807 Sq Ft
  • Built 2023

  21 Mire Ct, Monticello, FL 32344

  Last Sold Summary

  • 76 Days On Market

  Last Listing Agent Amber McKinney Hamilton Realty Advisors LLC
• 

  

  /26

  $75,000

  $9K PRICE DROP

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

  vacant E 2nd Way, Greenville, FL 32331

  Located just off Ashville Highway, this 5-acre homesite offers the kind of North Florida setting buyers search for but rarely find. Tucked along a quiet road with minimal traffic, the property provides peace, privacy, and room to create the lifestyle you’ve been wanting. Scattered with beautiful mature oak trees, the land has character, shade, and a timeless natural feel that is hard to

  Bridget Davis OaksFeather Realty

  vacant E 2nd Way, Greenville, FL 32331
• 

  

  /42

  $710,000

  Sold Apr 20, 2026

  81 Old Tung Grove Rd, Monticello, FL 32344

  • 4 Beds
  • 3.5 Baths
  • 2,365 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $300/SF
  • 204 Days On Market

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc

  81 Old Tung Grove Rd, Monticello, FL 32344
• 

  

  /42

  Not Listed For Sale

  24 Mire Ct, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,807 Sq Ft
  • Built 2024

  24 Mire Ct, Monticello, FL 32344

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Amber McKinney Hamilton Realty Advisors LLC
• 

  

  /44

  $364,900

  $15K PRICE INCREASE

  • 2,750 Sq Ft

  480 S Jefferson St, Monticello, FL 32344

  Located in the heart of Monticello, this 5-unit investment property offers a prime opportunity for investors looking to add value and generate income. Positioned just minutes from local businesses, shopping, dining, and convenient interstate access, the location provides strong appeal for tenants seeking both convenience and accessibility. Currently, 3 of the units are occupied, providing

  Chip Williams Keller Williams Town & Country

  480 S Jefferson St, Monticello, FL 32344

Showing Results 281 - 320, Page 8 of 18