Jefferson County, FL Homes

• 

  

  

  /24

  Est $313,508

  Not Listed For Sale

  825 E Dogwood St, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft
  • Built 1910

  825 E Dogwood St, Monticello, FL 32344

  Last Sold Summary

  • 57 Days On Market
• 

  

  

  /57

  $699,000

  • 6 Beds
  • 3.5 Baths
  • 3,114 Sq Ft

  365 S Mulberry St, Monticello, FL 32344

  Historic soul. Modern substance. A rare circa-late 1800s home, beautifully restored and thoughtfully made NEW. Some houses simply endure... and some are given the rare chance to begin again. Better than New Construction! Just two blocks from the courthouse square in Monticello, Fl, this circa-late 1800s home—a classic Southern I-house shaped by Greek Revival influence—once stood quietly

  Lee Hall Capital City Real Estate Group

  365 S Mulberry St, Monticello, FL 32344
• 

  

  

  /11

  $170,000

  Sold May 15, 2026

  275 W High St, Monticello, FL 32344

  • 2 Beds
  • 1 Bath
  • 962 Sq Ft
  • Built 1962

  Last Sold Summary

  • $177/SF
  • 6 Days On Market

  Last Listing Agent Heather Boyd FL-GA Realty & Auction

  275 W High St, Monticello, FL 32344
• 

  

  

  /3

  Est $481,686

  Not Listed For Sale

  1612 Rabon Rd, Monticello, FL 32344

  • 4 Beds
  • 2.5 Baths
  • 3,250 Sq Ft
  • Built 1988

  1612 Rabon Rd, Monticello, FL 32344

  Last Sold Summary
• 

  

  

  /19

  $299,000

  $51K PRICE DROP

  • Land
  • 70.45 Acres
  • $4,244 per Acre

  265 Neely Rd, Monticello, FL 32344

  Secluded, but not remote, this 70.45 acre tract in eastern Jefferson County, Florida would make an ideal hunting getaway property or a rural homesite. Virtually no ambient noise or light that will disturb the quiet woods. About half the tract is in 7-year-old planted loblolly pines and the rest is in natural woods and cypress ponds. You will be smack in the middle of some of the best deer and

  Dave Lewis Southern Forestry Realty

  265 Neely Rd, Monticello, FL 32344
• 

  

  /42

  $335,000

  Sold Jun 10, 2025

  1535 Willow Rd, Monticello, FL 32344

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

  Last Sold Summary

  • $245/SF
  • 6 Days On Market

  Current Estimated Value $374,139

  Last Listing Agent Chance Shutes Keller Williams Town & Country

  1535 Willow Rd, Monticello, FL 32344
• 

  

  /24

  Not Listed For Sale

  6279 Aucilla Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,216 Sq Ft
  • Built 1999

  6279 Aucilla Rd, Monticello, FL 32344

  Last Sold Summary

  • 79 Days On Market
• 

  

  /16

  $487,878

  $220K PRICE DROP

  • Land
  • 122 Acres
  • $3,999 per Acre

  0 James Noble Rd, Greenville, FL 32331

  Millwood Timberland East is a balanced property located in a great recreational market. The Ashville area is home to numerous trophy grade recreational properties and is known for exceptional whitetail, turkey and waterfowl hunting. This property features an efficient footprint with good access and internal road infrastructure. The uplands are planted with slash pine that are approximately 8

  Bryant Peace Saunders Real Estate

  0 James Noble Rd, Greenville, FL 32331
• 

  

  /12

  $78,000

  Sold Apr 10, 2026

  489 Ashville Highlands Dr, Greenville, FL 32331

  • Land
  • 5 Acres
  • $15,600 per Acre

  Last Sold Summary

  • 22% Below List Price
  • 230 Days On Market

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc

  489 Ashville Highlands Dr, Greenville, FL 32331
• 

  

  /40

  Not Listed For Sale

  535 E Duck Pond Dr, Greenville, FL 32331

  • 2 Beds
  • 1 Bath
  • 1,053 Sq Ft
  • Built 1985

  535 E Duck Pond Dr, Greenville, FL 32331

  Last Sold Summary

  • 88 Days On Market
• 

  

  /45

  $279,900

  • 3 Beds
  • 2 Baths
  • 1,856 Sq Ft

  1120 Deerwood Blvd, Greenville, FL 32331

  This beautiful 3 bedroom, 2 bathroom home offers 1,865+/- square feet of comfortable living space and sits on 5+/- acres, giving you the perfect mix of country living, privacy, and convenience. With large road frontage and a privacy fence stretching across the entire front of the property along the dirt road, this place offers the peaceful setting folks are looking for while still feeling warm

  Jaye Cowart Mossy Oak Properties Southern Land and Homes, LLC

  1120 Deerwood Blvd, Greenville, FL 32331
• 

  

  /36

  $285,000

  Sold Aug 08, 2025

  705 N Mulberry St, Monticello, FL 32344

  • 3 Beds
  • 2.5 Baths
  • 1,527 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $187/SF
  • 40 Days On Market

  Current Estimated Value $282,135

  Last Listing Agent Bill Lord CONSULTANTS TO HOMEBUI

  705 N Mulberry St, Monticello, FL 32344
• 

  

  /18

  Est $277,755

  Not Listed For Sale

  622 Limestone Rd, Monticello, FL 32344

  • 5 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • Built 1965

  622 Limestone Rd, Monticello, FL 32344

  Last Sold Summary

  • 52 Days On Market
• 

  

  /8

  $450,000

  • Land
  • 85.26 Acres
  • $5,278 per Acre

  1899 Big Joe Rd, Monticello, FL 32344

  Known for its white tail deer, hog and turkey populations, this 85.26 acres in Jefferson County, FL would make a perfect hunting camp. Pristine pine tree property just minutes from Interstate 10 / Exit 225. Ideal Country Estate or weekend get-away. Seller financing available to qualified buyer.

  Tom Woodyard Woodyard & Associates, LLC

  1899 Big Joe Rd, Monticello, FL 32344
• 

  

  /40

  $198,000

  Sold Mar 19, 2026

  418 Quail Ln, Monticello, FL 32344

  • 2 Beds
  • 2 Baths
  • 1,050 Sq Ft
  • Built 2000

  Last Sold Summary

  • 2% Above List Price
  • $189/SF
  • 2 Days On Market

  Last Listing Agent Heather Boyd FL-GA Realty & Auction

  418 Quail Ln, Monticello, FL 32344
• 

  

  /33

  Not Listed For Sale

  1692 Freeman Rd, Lamont, FL 32336

  • 3 Beds
  • 2 Baths
  • 1,472 Sq Ft
  • Built 2006

  1692 Freeman Rd, Lamont, FL 32336

  Last Sold Summary

  • 103 Days On Market
• 

  

  /20

  $570,000

  • Land
  • 71 Acres
  • $8,028 per Acre

  0 Aucilla Rd Unit 22696476, Monticello, FL 32344

  Located on Aucilla Rd in Monticello, FL, this versatile AG-5 property offers endless potential for residential, agricultural, and recreational use. The upland portion has been cleared, making it ideal for a homesite or multiple residences, with zoning allowing one unit per five acres and options for family transfers under county guidelines.For those looking to enjoy North Floridas natural

  Jeremiah Thompson Saunders Land

  0 Aucilla Rd Unit 22696476, Monticello, FL 32344
• 

  

  /43

  $519,000

  Sold Oct 31, 2025

  79 Lakeside Rd, Monticello, FL 32344

  • 4 Beds
  • 2.5 Baths
  • 3,054 Sq Ft
  • Built 1940

  Last Sold Summary

  • 4% Below List Price
  • $170/SF
  • 98 Days On Market

  Current Estimated Value $507,914

  Last Listing Agent Michael Schilling Hill Spooner & Elliott Inc

  79 Lakeside Rd, Monticello, FL 32344
• 

  

  /31

  Est $145,285

  Not Listed For Sale

  821 Old Lloyd Rd Unit 2, Monticello, FL 32344

  • 3 Beds
  • Built 1988

  821 Old Lloyd Rd Unit 2, Monticello, FL 32344

  Last Sold Summary

  • 223 Days On Market
• 

  

  /57

  $599,000

  • 7 Beds
  • 7 Baths
  • 5,139 Sq Ft

  625 E Washington St, Monticello, FL 32344

  Introducing a stunning 1.2 acre estate in the heart of Historic Downtown Monticello. The Simon-Ridgeway home was built in 1888 and boasts a generous 4,500 sq ft of living space and features 7 spacious bedrooms, 5 of which come with its own en-suite bathroom for ultimate privacy and convenience. City granted BNB status - making this perfect for an owner/occupier wanting to work from home and enjoy

  Lee Hall Capital City Real Estate Group

  625 E Washington St, Monticello, FL 32344
• 

  

  /11

  $65,000

  Sold Apr 30, 2026

  1309 Cook Rd, Lamont, FL 32336

  • Land
  • 3 Acres
  • $21,667 per Acre

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Alicia Radtke All Realty Services

  1309 Cook Rd, Lamont, FL 32336
• 

  

  /5

  Est $152,212

  Not Listed For Sale

  220 Horseshoe Rd, Monticello, FL 32344

  • 3 Beds
  • 1 Bath
  • 1,314 Sq Ft
  • Built 1977

  220 Horseshoe Rd, Monticello, FL 32344

  Last Sold Summary

  • 36 Days On Market
• 

  

  /66

  $399,000

  • 3 Beds
  • 2 Baths
  • 2,280 Sq Ft

  1012 S Main Ave, Monticello, FL 32344

  Tucked away on 5 private acres down a quiet, wooded road, this brick home offers 2,280 square feet with a split floor plan featuring 3 bedrooms and 2 baths, providing both space and functionality. New Roof November 2025, Well 2022, and septic drain field replaced 2016. Inside, you’ll find a cozy fireplace and a bright sunroom that brings the outdoors in, while the solid layout offers plenty of

  Catherine Hope All Realty Services

  1012 S Main Ave, Monticello, FL 32344
• 

  

  /41

  $374,000

  Sold Jan 21, 2026

  226 Sutton, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 2024

  Last Sold Summary

  • 1% Below List Price
  • $257/SF
  • 3 Days On Market

  Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

  226 Sutton, Monticello, FL 32344
• 

  

  /34

  Not Listed For Sale

  336 Lake Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 1999

  336 Lake Rd, Monticello, FL 32344

  Last Sold Summary

  • 99 Days On Market
• 

  

  /38

  $449,900

  • 3 Beds
  • 2 Baths
  • 1,774 Sq Ft

  107 S Tarn Way, Monticello, FL 32344

  Welcome to this beautifully custom-built 3 bedroom, 2 bath home completed in 2024 and located in the desirable Hemings Pond Subdivision. Offering the perfect blend of modern construction and thoughtful upgrades, this move-in ready showcases luxury vinyl plank flooring, upgraded light fixtures, premium countertops, and elegant bath fixtures. Owner selected custom enhancements elevate the space

  Joana Villeneuve Hill Spooner & Elliott Inc

  107 S Tarn Way, Monticello, FL 32344
• 

  

  /26

  $130,000

  Sold Jul 25, 2025

  00 Cardinal Ln, Monticello, FL 32344

  • Land
  • 14.1 Acres
  • $9,220 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 175 Days On Market

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

  00 Cardinal Ln, Monticello, FL 32344
• 

  

  /28

  Est $459,651

  Not Listed For Sale

  129 Indian Hills Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 3,328 Sq Ft
  • Built 1996

  129 Indian Hills Rd, Monticello, FL 32344

  Last Sold Summary

  • 180 Days On Market
• 

  

  /31

  $434,000

  $5K PRICE DROP

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

  285 Mallard Ln, Monticello, FL 32344

  *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 screened in back porch with a propane hookup for

  Shelley Duke Red Bird Realty

  285 Mallard Ln, Monticello, FL 32344
• 

  

  /46

  $645,000

  Sold Apr 10, 2026

  178 White Oak Dr, Monticello, FL 32344

  • 3 Beds
  • 2.5 Baths
  • 2,172 Sq Ft
  • Built 2024

  Last Sold Summary

  • $297/SF
  • 16 Days On Market

  Last Listing Agent Chance Shutes Keller Williams Town & Country

  178 White Oak Dr, Monticello, FL 32344
• 

  

  /38

  Est $188,229

  Not Listed For Sale

  310 N Olive St, Monticello, FL 32344

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1948

  310 N Olive St, Monticello, FL 32344

  Last Sold Summary

  • 36 Days On Market
• 

  

  /70

  $795,000

  • 3 Beds
  • 2.5 Baths
  • 2,160 Sq Ft

  660 Whispering Hill, Monticello, FL 32344

  Set on 18+ acres of beautifully maintained pasture, this private country property is built for both everyday living, true equestrian use or small livestock farm. The land is the star- fully fenced with new wood fencing that cleanly defines multiple pastures, a peaceful pond, and wide open space to ride, graze and enjoy. The 6-stall horse barn is ready to work with paddocks attached to each stall,

  Catherine Hope All Realty Services

  660 Whispering Hill, Monticello, FL 32344
• 

  

  /24

  $83,000

  Sold Jan 12, 2026

  0 Johnny Unit 392570, Lamont, FL 32336

  • Land
  • 5.03 Acres
  • $16,501 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 46 Days On Market

  Last Listing Agent Michael Reavis The Naumann Group Real Estate

  0 Johnny Unit 392570, Lamont, FL 32336
• 

  

  /36

  Est $710,420

  Not Listed For Sale

  250 Hiawatha Farms Rd, Monticello, FL 32344

  • 4 Beds
  • 3 Baths
  • 5,556 Sq Ft
  • Built 1998

  250 Hiawatha Farms Rd, Monticello, FL 32344

  Last Sold Summary

  • 332 Days On Market
• 

  

  /31

  $625,000

  • 4 Beds
  • 3 Baths
  • 2,716 Sq Ft

  140 Shumard Ct, Monticello, FL 32344

  Discover this stunning 2,600+ sqft home built in 2021, offering the perfect blend of quiet country living and modern convenience. Adjoinging additional lot can also be purchased! Features include: 4 spacious bedrooms and 3 full bathrooms 2 master bedrooms located downstairs Dedicated office/bonus room – ideal for work or hobbies Modern kitchen and open living spaces Attached 2-car garage Just

  Caleb Stephens Silo Hill Properties

  140 Shumard Ct, Monticello, FL 32344
• 

  

  /40

  $255,000

  Sold Jun 30, 2025

  185 Main St, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 2,206 Sq Ft
  • Built 1914

  Last Sold Summary

  • 15% Below List Price
  • $116/SF
  • 93 Days On Market

  Current Estimated Value $291,002

  Last Listing Agent Lee Hall Capital City Real Estate Group

  185 Main St, Monticello, FL 32344
• 

  

  /42

  Est $260,558

  Not Listed For Sale

  52 Serenity Ln, Monticello, FL 32344

  • Built 2019

  52 Serenity Ln, Monticello, FL 32344

  Last Sold Summary

  • 25 Days On Market
• 

  /2

  $439,900

  New Construction Under Contract

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft

  110 Crooked Creek Ln, Monticello, FL 32344

  Welcome to this exquisite soon to be finished new construction home in the quiet and quaint Crooked Creek Subdivision, conveniently located just off of 90E and only minutes away from the historic charm of Downtown Monticello. With easy access for commuting to Tallahassee or Thomasville, this location offers the perfect balance of peaceful living and convenient amenities. Immerse yourself in the

  Ross Kozloski Kozloski Realty, LLC

  110 Crooked Creek Ln, Monticello, FL 32344
• 

  

  /18

  $2,378,000

  Sold Nov 06, 2025

  1268 NW White Wing Dove Dr, Greenville, FL 32331

  • Land
  • 765 Acres
  • $3,108 per Acre

  Last Sold Summary

  • 9% Below List Price
  • 15 Days On Market

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

  1268 NW White Wing Dove Dr, Greenville, FL 32331
• 

  

  /7

  Not Listed For Sale

  0 Taylor Rd Unit 375808, Monticello, FL 32344

  0 Taylor Rd Unit 375808, Monticello, FL 32344

  Last Sold Summary

  • 20 Days On Market

Showing Results 121 - 160, Page 4 of 18