Jefferson County, FL Homes

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  /42

  $260,000

  Sold Aug 29, 2025

  2422 N Jefferson St, Monticello, FL 32344

  • 3 Beds
  • 3 Baths
  • 2,280 Sq Ft
  • Built 2000

  Last Sold Summary

  • 3% Below List Price
  • $114/SF
  • 135 Days On Market

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

  2422 N Jefferson St, Monticello, FL 32344
• 

  

  

  /27

  Not Listed For Sale

  81 Coopers Pond Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,601 Sq Ft
  • Built 2024

  81 Coopers Pond Rd, Monticello, FL 32344

  Last Sold Summary

  • 129 Days On Market
• 

  

  

  /4

  $125,000

  • Land
  • 5.05 Acres
  • $24,752 per Acre

  455 E Duck Pond Dr, Greenville, FL 32331

  This natual beauty of 5 acres with house and shed is priced for land value. The delapidated structures holds little to no value. With ownership afar, the property has been untouched for years. Hinting at what once was and what could be again, this property invites a lifestyle of peace and seclusion giving you a unique opportunity to create your own sanctuary complete with a pond that mirrors the

  

  Ursula Hannah

  1st Realty Appraisal Inc

  (448) 202-7237

  455 E Duck Pond Dr, Greenville, FL 32331
• 

  

  

  /14

  $30,000

  Sold Nov 21, 2025

  000 Ashville Highlands Dr, Greenville, FL 32331

  • Land
  • 5 Acres
  • $6,000 per Acre

  Last Sold Summary

  • 54% Below List Price
  • 58 Days On Market

  Last Listing Agent Alicia Radtke All Realty Services

  000 Ashville Highlands Dr, Greenville, FL 32331
• 

  

  

  /6

  Not Listed For Sale

  xxx S Main Ave, Monticello, FL 32344

  xxx S Main Ave, Monticello, FL 32344

  Last Sold Summary

  • 24 Days On Market
• 

  

  /61

  $989,000

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

  9901 Gamble Rd, Monticello, FL 32344

  A LAND REMEMBERED-Discover a rare opportunity to own over 40 acres of land where conservation and nature meet comfort and privacy. Scenic walking trails wind throughout the property, creating a peaceful retreat for nature lovers. The home features major upgrades, including a new roof, Pella double-paned energy-efficient windows, and a new water heater. Inside, enjoy 9 foot ceilings throughout the

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 256-3073

  9901 Gamble Rd, Monticello, FL 32344
• 

  

  /66

  $850,000

  Sold Feb 09, 2026

  740 Kinsey Rd, Monticello, FL 32344

  • 3 Beds
  • 1 Bath
  • 1,146 Sq Ft
  • Built 1941

  Last Sold Summary

  • 29% Below List Price
  • $742/SF
  • 298 Days On Market

  Current Estimated Value $957,528

  Last Listing Agent Ben Jones Southern Land & Homes

  740 Kinsey Rd, Monticello, FL 32344
• 

  

  /4

  Not Listed For Sale

  0 Taylor Rd Unit 377923, Monticello, FL 32344

  0 Taylor Rd Unit 377923, Monticello, FL 32344

  Last Sold Summary

  • 91 Days On Market
• 

  

  /37

  $345,000

  $75K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,766 Sq Ft

  205 N Rhodes St, Monticello, FL 32344

  Classic historical home built in the 1920's. Walking distance to charming downtown Monticello. Large covered front porch for kicking back and relaxing. Wood floors throughout, high ceiling and large open kitchen. This beauty boast over 2700 sf of heated and cooled living space. Beautiful entry into foyer with stairway leading to upstairs landing and two bedrooms. Formal living, formal dining and

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 994-2623

  205 N Rhodes St, Monticello, FL 32344
• 

  

  /11

  $90,000

  Sold Jan 13, 2026

  4685 Waukeenah Hwy, Monticello, FL 32344

  • 1 Bed
  • 1 Bath
  • 1,064 Sq Ft
  • Built 2005

  Last Sold Summary

  • 25% Below List Price
  • $85/SF
  • 4 Days On Market

  Current Estimated Value $103,261

  Last Listing Agent E. Bradley Vollertsen Advanced Real Estate Sales

  4685 Waukeenah Hwy, Monticello, FL 32344
• 

  

  /21

  Not Listed For Sale

  750 N Cherry St, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 2000

  750 N Cherry St, Monticello, FL 32344

  Last Sold Summary

  • 102 Days On Market
• 

  

  /4

  $425,000

  • Land
  • 33.26 Acres
  • $12,778 per Acre

  TBD Cavallo Trail, Lloyd, FL 32344

  33+ acres in very nice rural subdivision. All wooded and will need some clearing for a homesite. Easy access to Tallahassee. Community water is available with tap in charge approx. $2500.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 231-5754

  TBD Cavallo Trail, Lloyd, FL 32344
• 

  

  /6

  $217,500

  Sold Feb 19, 2026

  TBD Orchard Ln, Monticello, FL 32344

  • Land
  • 10 Acres
  • $21,750 per Acre

  Last Sold Summary

  • 5% Below List Price
  • 4 Days On Market

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc

  TBD Orchard Ln, Monticello, FL 32344
• 

  

  /5

  Est $110,655

  Not Listed For Sale

  394 E Osprey Ln, Monticello, FL 32344

  • 3 Beds
  • Built 1988

  394 E Osprey Ln, Monticello, FL 32344

  Last Sold Summary

  • 41 Days On Market
• 

  

  /70

  $2,000,000

  • 7 Beds
  • 7 Baths
  • 5,756 Sq Ft

  305 Old Lloyd Rd, Monticello, FL 32344

  Welcome to a rare opportunity to own a true estate property where space, craftsmanship, and privacy come together on 18 beautiful acres. This impressive 7-bedroom, 5 full bath, 2 half bath two-story home offers a thoughtfully designed layout ideal for both everyday living and entertaining on a grand scale. Upstairs features 4 bedrooms and 2 full baths, while the downstairs includes 2 bedrooms,

  

  Chance Shutes

  Keller Williams Town & Country

  (448) 850-0716

  305 Old Lloyd Rd, Monticello, FL 32344
• 

  

  /26

  $231,000

  Sold Aug 20, 2025

  495 N Cherry Ct, Monticello, FL 32344

  • 2 Beds
  • 2 Baths
  • 1,338 Sq Ft
  • Built 2005

  Last Sold Summary

  • 14% Below List Price
  • $173/SF
  • 161 Days On Market

  Current Estimated Value $235,843

  Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

  495 N Cherry Ct, Monticello, FL 32344
• 

  

  /37

  Not Listed For Sale

  107 Tarn Way, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,806 Sq Ft
  • Built 2024

  107 Tarn Way, Monticello, FL 32344

  Last Sold Summary

  • 46 Days On Market
• 

  

  /8

  $69,000

  • Land
  • 10.2 Acres
  • $6,765 per Acre

  tbd E 2nd Way, Greenville, FL 32331

  10.2 acre wooded wonderland, corner acreage fronting on 3 roads. Will sell as 2 - 5 acre parcels for $39,500 for each parcel.

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 202-4278

  tbd E 2nd Way, Greenville, FL 32331
• 

  

  /8

  $35,000

  Sold Jul 30, 2025

  1024 Vista Rd, Monticello, FL 32344

  • Land
  • 5 Acres
  • $7,000 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 341 Days On Market

  Current Estimated Value $37,903

  Last Listing Agent Heather Boyd FL-GA Realty & Auction

  1024 Vista Rd, Monticello, FL 32344
• 

  

  /7

  Not Listed For Sale

  0 Taylor Rd Unit 376815, Monticello, FL 32344

  0 Taylor Rd Unit 376815, Monticello, FL 32344

  Last Sold Summary

  • 74 Days On Market
• 

  /2

  $65,000

  $10K PRICE DROP

  • Land
  • 1.7 Acres
  • $38,235 per Acre

  TBD Scott Dr, Monticello, FL 32344

  1.7 acres, two lots hidden in Monticello. Will not divide. Private setting with Plantation to the west. There is a 15 ft recorded easement to the property but currently working on additional road access. No sign on property. .

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 327-3237

  TBD Scott Dr, Monticello, FL 32344
• 

  

  /20

  $82,500

  Sold Jul 02, 2025

  91 W 7th Way, Greenville, FL 32331

  • Land
  • 5 Acres
  • $16,500 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 30 Days On Market

  Current Estimated Value $81,798

  Last Listing Agent Heather Rybak Rybak Realty, LLC

  91 W 7th Way, Greenville, FL 32331
• 

  

  /9

  Not Listed For Sale

  1446 Ashville Highlands Dr, Greenville, FL 32331

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1995

  1446 Ashville Highlands Dr, Greenville, FL 32331

  Last Sold Summary

  • 137 Days On Market
• 

  

  /60

  $550,000

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft

  925 Hiawatha Farms Rd, Monticello, FL 32344

  (One or more photos has been virtually staged) Custom hurricane-resistant/efficiency home on 3.6 private acres in a gated equestrian community, just 17 miles east of Tallahassee and 1 mile to I-10 (Exit 217). Built in 2013, this 2,112 sq ft home features 4 bedrooms, 3 full baths, and 9’ ceilings throughout. Constructed with Nudura ICF 12” insulated concrete exterior walls for superior strength,

  

  Joann Jacobs

  ROGERS BARRY, REALTOR

  (448) 231-5955

  925 Hiawatha Farms Rd, Monticello, FL 32344
• 

  

  /48

  $1,012,500

  Sold Apr 29, 2026

  237 Valley View Ct, Monticello, FL 32344

  • 8 Beds
  • 6.5 Baths
  • 5,560 Sq Ft
  • Built 1998

  Last Sold Summary

  • 1% Above List Price
  • $182/SF
  • 22 Days On Market

  Current Estimated Value $906,266

  Last Listing Agent Kelly Vinson Keller Williams Town & Country

  237 Valley View Ct, Monticello, FL 32344
• 

  

  /22

  Not Listed For Sale

  0 Deerwood Blvd Unit 376476, Greenville, FL 32331

  0 Deerwood Blvd Unit 376476, Greenville, FL 32331

  Last Sold Summary

  • 99 Days On Market
• 

  

  /51

  $409,500

  $16K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,127 Sq Ft

  1628 N Jefferson Hwy, Monticello, FL 32344

  Picturesque, 3/2, brick beauty with a whimsical style that evokes the charm of a traditional storybook estate, with 3,217 sq. ft., bordering a large acreage holding on 2 sides. Beautiful attributes from the 1955 era such as cedar lined closet, crystal door knobs, original oak floors, wide baseboards, double bay windows, 24x10 screened porch and entertainment deck. Lifetime metal Roof! Boasting

  

  Lynette Sirmon

  All Realty Services

  (448) 288-6919

  1628 N Jefferson Hwy, Monticello, FL 32344
• 

  

  /61

  $330,000

  Sold Jan 29, 2026

  864 Ashville Hwy, Monticello, FL 32344

  • 2 Beds
  • 2 Baths
  • 1,472 Sq Ft
  • Built 1930

  Last Sold Summary

  • 1% Below List Price
  • $224/SF
  • 1 Day On Market

  Current Estimated Value $323,374

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

  864 Ashville Hwy, Monticello, FL 32344
• 

  

  /42

  Est $964,072

  Not Listed For Sale

  542 Tradition Way, Monticello, FL 32344

  • 4 Beds
  • 2.5 Baths
  • 2,750 Sq Ft
  • Built 2018

  542 Tradition Way, Monticello, FL 32344

  Last Sold Summary

  • 38 Days On Market
• 

  

  /27

  $349,000

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

  8156 Waukeenah Hwy, Monticello, FL 32344

  Rare Find! Country Living on 1 Acre-No HOA! Enjoy peaceful country living on a full 1-acre property with no HOA restrictions. This spacious 1774 square foot home features 3 bedrooms and 2 bathrooms with a bright open concept layout. The home features LVP flooring throughout, fresh interior paint in main living area, and a new roof in 2023 for added piece of mind. The primary suite includes a

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 218-0336

  8156 Waukeenah Hwy, Monticello, FL 32344
• 

  

  /25

  $74,090

  Sold Dec 12, 2025

  687 Smokehouse Farms Dr Unit na, Greenville, FL 32331

  • Land
  • 5.01 Acres
  • $14,788 per Acre

  Last Sold Summary

  • 13% Below List Price
  • 54 Days On Market

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

  687 Smokehouse Farms Dr Unit na, Greenville, FL 32331
• 

  

  /23

  Not Listed For Sale

  5585 Turkey Scratch Rd, Monticello, FL 32344

  • 4 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 2003

  5585 Turkey Scratch Rd, Monticello, FL 32344

  Last Sold Summary

  • 33 Days On Market
• 

  

  /38

  $274,900

  • 2 Beds
  • 2 Baths
  • 1,411 Sq Ft

  490 N Cherry Ct, Monticello, FL 32344

  Step into city living just steps from Downtown Monticello, Fl. This one-story condo with private backyard blends modern convenience in this coveted over 55 neighborhood of only 8 units. 2 bedrooms & 2 baths, laundry room with stack unit, W/D included, but the favorite room in the house is the sunroom. Inside, enjoy the bright open-concept living with high ceilings, crown molding, LVP & engineered

  

  Pam Hoveland

  Landcorp, Inc.

  (448) 288-3932

  490 N Cherry Ct, Monticello, FL 32344
• 

  

  /46

  $900,000

  Sold Mar 23, 2026

  525 Taylor Rd, Monticello, FL 32344

  • 4 Beds
  • 4.5 Baths
  • 3,610 Sq Ft
  • Built 2005

  Last Sold Summary

  • 14% Below List Price
  • $249/SF
  • 7 Days On Market

  Current Estimated Value $951,103

  Last Listing Agent Michele Arceneaux Kelly & Kelly Properties, Inc

  525 Taylor Rd, Monticello, FL 32344
• 

  

  /12

  Not Listed For Sale

  509 Waukeenah Hwy, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1999

  509 Waukeenah Hwy, Monticello, FL 32344

  Last Sold Summary

  • 97 Days On Market
• 

  

  /21

  $172,500

  • Land
  • 10 Acres
  • $17,250 per Acre

  TBD Rainey Run, Monticello, FL 32344

  Gated rural community, lakefront 10 acres with large hardwoods. Tranquility awaits, gently sloping land with some clearing.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 678-2958

  TBD Rainey Run, Monticello, FL 32344
• 

  

  /54

  $500,000

  Sold May 01, 2026

  70 Generation Ct, Monticello, FL 32344

  • 4 Beds
  • 3 Baths
  • 2,784 Sq Ft
  • Built 2017

  Last Sold Summary

  • 5% Below List Price
  • $180/SF
  • 36 Days On Market

  Current Estimated Value $530,252

  Last Listing Agent Lee Duggar Re/Max Professionals Realty

  70 Generation Ct, Monticello, FL 32344
• 

  

  /42

  Not Listed For Sale

  1851 Whitehouse Rd, Monticello, FL 32344

  • 4 Beds
  • 2.5 Baths
  • 2,057 Sq Ft
  • Built 2005

  1851 Whitehouse Rd, Monticello, FL 32344

  Last Sold Summary

  • 2 Days On Market
• 

  

  /69

  $555,000

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,945 Sq Ft

  64 Sanctuary Dr, Monticello, FL 32344

  Just WOW this beautiful new construction home, with top-of-the-line custom finishes. This home gives you all the luxury you are looking for - a primary suite with stunning tongue and groove wood tray ceilings, master bath with stand-alone soaking tub, walk-in shower, double vanity with quartz countertops, an oversized walk-in custom master closet with built-ins. As you approach the living area,

  

  Chance Shutes

  Keller Williams Town & Country

  (448) 205-2800

  64 Sanctuary Dr, Monticello, FL 32344
• 

  

  /59

  $530,000

  Sold Jan 05, 2026

  1923 Whitehouse Rd, Monticello, FL 32344

  • 4 Beds
  • 3 Baths
  • 2,371 Sq Ft
  • Built 2008

  Last Sold Summary

  • 1% Below List Price
  • $224/SF
  • 29 Days On Market

  Current Estimated Value $523,875

  Last Listing Agent Bonnie Fowler CONSULTANTS TO HOMEBUI

  1923 Whitehouse Rd, Monticello, FL 32344

Showing Results 81 - 120, Page 3 of 18