Jefferson County, FL Homes

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  /2

  Not Listed For Sale

  A Salt Rd, Monticello, FL 32344

  A Salt Rd, Monticello, FL 32344

  Last Sold Summary

  • 86 Days On Market

  Last Listing Agent Sherry Shaheen ENGEL & VOLKERS GAINESVILLE
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  /28

  $3,999

  $17K PRICE DROP

  • 2 Beds
  • 2 Baths

  10 S Front Ct, Monticello, FL 32344

  If you purchase this home, receive 2 months FREE site rent plus pay NO application fees. Hurry! Offer expires August 31, 2026. Act fast! Restrictions apply. Looking for an affordable home with plenty of potential? This handyman special is the perfect opportunity to add your personal touch and build instant sweat equity. With a functional layout, generous living space, and solid bones, this home

  Patty Davis Jefferson Pines

  10 S Front Ct, Monticello, FL 32344
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  /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
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  /5

  Not Listed For Sale

  354 W 12th Dr, Greenville, FL 32331

  354 W 12th Dr, Greenville, FL 32331

  Last Sold Summary

  • 253 Days On Market

  Last Listing Agent Kyle Geoghagan Keller Williams Town & Country
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  /56

  $305,000

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft

  395 Sunset Dr, Monticello, FL 32344

  Welcome home to this charming 3-bedroom, 2-bath property set on a spacious lot with a fully fenced backyard. Thoughtfully updated throughout, major improvements include a 2023 metal roof, new HVAC system, new windows, and a new electric on-demand water heater. The renovated kitchen features all new appliances and a clean, modern look. The second full bath is conveniently located just off the rear

  Catherine Hope All Realty Services

  395 Sunset Dr, Monticello, FL 32344
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  /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

  Current Estimated Value $580,281

  Last Listing Agent Brett Miller Legacy Pro Real Estate Group

  44 S Ojibwa Rd, Monticello, FL 32344
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  /36

  Not Listed For Sale

  87 Old Tung Grove Rd, Monticello, FL 32344

  • 4 Beds
  • 3 Baths
  • 2,344 Sq Ft
  • Built 2024

  87 Old Tung Grove Rd, Monticello, FL 32344

  Last Sold Summary

  • 362 Days On Market

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc
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  /70

  $1,325,000

  Under Contract

  • 5 Beds
  • 4.5 Baths
  • 5,476 Sq Ft

  221 Kiley Dr, Monticello, FL 32344

  Welcome to a rare North Florida estate just minutes from Tallahassee—where luxury, land, and lifestyle come together. 221 Kiley Road is situated on expansive acreage in Monticello, and this private retreat offers the perfect blend of seclusion and convenience, located just a short drive from the heart of Tallahassee. For buyers seeking space, privacy, and versatility without sacrificing proximity

  Wilda Sigler Keller Williams Town & Country

  221 Kiley Dr, Monticello, FL 32344
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  /6

  $408,882

  Sold Jun 30, 2026

  1310 Piney Woods Rd, Monticello, FL 32344

  • Land
  • 58.46 Acres
  • $6,994 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 33 Days On Market

  Current Estimated Value $449,000

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc

  1310 Piney Woods Rd, Monticello, FL 32344
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  /35

  Not Listed For Sale

  129 White Oak Dr, Monticello, FL 32344

  • 4 Beds
  • 2 Baths
  • 1,945 Sq Ft
  • Built 2024

  129 White Oak Dr, Monticello, FL 32344

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Marshall Gibbs Capital City Real Estate Group
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  /2

  $69,000

  • Land
  • 19,602 Sq Ft
  • $153,333 per Acre

  Lot 14 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 14 & 21 directly behind it totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 14 E Washington St, Monticello, FL 32344
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  /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
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  /37

  Not Listed For Sale

  185 White Oak Dr, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,976 Sq Ft
  • Built 2024

  185 White Oak Dr, Monticello, FL 32344

  Last Sold Summary

  • 69 Days On Market

  Last Listing Agent Marshall Gibbs Capital City Real Estate Group
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  /44

  $235,000

  • 3 Beds
  • 1 Bath
  • 1,700 Sq Ft

  810 E Dogwood St, Monticello, FL 32344

  Step back in time and discover the charm of this classic Monticello home, offering timeless character and endless possibilities. Built in 1915, this Craftsman-style residence features 1,700 square feet of living space with hardwood floors, separate living and dining areas that reflect the home's historic appeal, 3 full bedrooms, with a large mud room and separate sitting room, a wood-burning

  Michael Balanoff Re/Max Professionals Realty

  810 E Dogwood St, Monticello, FL 32344
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  /57

  $180,000

  Sold Apr 29, 2026

  265 W Seminole Ave, Monticello, FL 32344

  • 2 Beds
  • 1 Bath
  • 1,741 Sq Ft
  • Built 1959

  Last Sold Summary

  • 22% Below List Price
  • $103/SF
  • 38 Days On Market

  Current Estimated Value $187,068

  Last Listing Agent Karen Gillispie Keller Williams Town & Country

  265 W Seminole Ave, Monticello, FL 32344
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  /22

  Not Listed For Sale

  390 Elliot Dr, Monticello, FL 32344

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

  390 Elliot Dr, Monticello, FL 32344

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Buddy Witmer Steve C. Walker Realty, LLC
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  /7

  $150,000

  $48K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,366 Sq Ft

  870 Shady Ln, Monticello, FL 32344

  Welcome to 870 Shady Lane in Monticello, Florida—a charming property that offers the perfect blend of privacy, space, and small-town appeal. Nestled on a quiet, tree-lined street, this home provides a peaceful retreat while still being conveniently close to the historic downtown district, local shops, and dining. Surrounded by mature trees and natural beauty, the property offers a serene setting

  Angela Graham Hamilton Realty Advisors LLC

  870 Shady Ln, Monticello, FL 32344
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  /45

  $755,000

  Sold Jul 10, 2026

  900 Ridge Rd, Monticello, FL 32344

  • 4 Beds
  • 2.5 Baths
  • 2,376 Sq Ft
  • Built 2003

  Last Sold Summary

  • 4% Below List Price
  • $318/SF
  • 79 Days On Market

  Current Estimated Value $764,800

  Last Listing Agent Brian Bachman Kelly & Kelly Properties, Inc

  900 Ridge Rd, Monticello, FL 32344
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  /42

  Est $747,596

  Not Listed For Sale

  12840 Gamble Rd, Monticello, FL 32344

  • 6 Beds
  • 4 Baths
  • 3,998 Sq Ft
  • Built 1991

  12840 Gamble Rd, Monticello, FL 32344

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Chris Cicatello Coldwell Banker Hartung
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  /63

  $254,999

  $5K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft

  196 Private Rd, Monticello, FL 32344

  Back on the market at NO FAULT TO THE SELLERS! Looking for a peaceful escape from the hustle and bustle? Welcome to your own private piece of North Florida! Tucked away on 5 beautiful acres between Tallahassee and historic Monticello, this spacious mobile home offers 1,792 square feet of comfortable living space with room to spread out and make it your own.Enjoy quiet mornings on the inviting

  Hunter Key OaksFeather Realty

  196 Private Rd, Monticello, FL 32344
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  /34

  $277,000

  Sold Jun 15, 2026

  450 W Madison St, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 2,070 Sq Ft
  • Built 1948

  Last Sold Summary

  • 1% Above List Price
  • $134/SF
  • 7 Days On Market

  Current Estimated Value $279,073

  Last Listing Agent Michael Manuel Armor Realty, Inc

  450 W Madison St, Monticello, FL 32344
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  /38

  Est $239,365

  Not Listed For Sale

  5118 E Washington Hwy, Monticello, FL 32344

  • 2 Beds
  • 1.5 Baths
  • 1,276 Sq Ft
  • Built 1935

  5118 E Washington Hwy, Monticello, FL 32344

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Amber Renaud The Nova Group Realty
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  /42

  $469,997

  New Construction Under Contract

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  51 Tarn Way, Monticello, FL 32344

  MOVE IN READY!! Amazing new construction 3 bedroom 2 bathroom plus office. Luxurious master suite, Kitchen made of dreams, this is a must see!

  Amber McKinney Hamilton Realty Advisors LLC

  51 Tarn Way, Monticello, FL 32344
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  /8

  $22,000

  Sold Jun 10, 2026

  923 King St, Monticello, FL 32344

  • Land
  • 14,374 Sq Ft
  • $66,667 per Acre

  Last Sold Summary

  • 24% Below List Price
  • 36 Days On Market

  Current Estimated Value $28,700

  Last Listing Agent Alicia Radtke All Realty Services

  923 King St, Monticello, FL 32344
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  /5

  Not Listed For Sale

  271 Tecumseh Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 2,128 Sq Ft
  • Built 1989

  271 Tecumseh Rd, Monticello, FL 32344

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc
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  /3

  $19,500

  • Land
  • 37,461 Sq Ft
  • $22,674 per Acre

  0 Cox Rd Unit 400763, Monticello, FL 32344

  0.84-Acre Monticello Lot on Cox Rd – SURVEY & ELEVATION LETTER ALREADY COMPLETED! Excellent opportunity to own a peaceful 0.84-acre parcel (Lots 89 & 90 of Springdale Pecan Plantation) located on Cox Road in beautiful Jefferson County. Surrounded by natural North Florida beauty, this lot offers rural tranquility while keeping you just minutes from historic downtown Monticello and 25-30 minutes to

  Stephen Hachey Flat Fee MLS Realty

  0 Cox Rd Unit 400763, Monticello, FL 32344
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  /48

  $480,000

  Sold Sep 26, 2025

  885 S Waukeenah St, Monticello, FL 32344

  • 5 Beds
  • 3.5 Baths
  • 4,600 Sq Ft
  • Built 1882

  Last Sold Summary

  • 9% Below List Price
  • $104/SF
  • 63 Days On Market

  Current Estimated Value $501,973

  Last Listing Agent Jason Boone Keller Williams Town & Country

  885 S Waukeenah St, Monticello, FL 32344
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  /42

  Not Listed For Sale

  178 Nautilus Dr, Monticello, FL 32344

  • 2 Beds
  • 2 Baths
  • 1,907 Sq Ft
  • Built 1996

  178 Nautilus Dr, Monticello, FL 32344

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Ondrea Maldonado Hamilton Realty Advisors LLC
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  /2

  $254,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,235 Sq Ft

  360 Bowman St, Monticello, FL 32344

  New construction; very convenient to downtown; house is close to completion - should be ready in about 45 days.

  Steve Walker Steve C. Walker Realty, LLC

  360 Bowman St, Monticello, FL 32344
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  /2

  $35,000

  Sold Dec 03, 2025

  lot 15 & 16 Partridge Ln, Monticello, FL 32344

  • Land
  • 1 Acre
  • $35,000 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Ashley Knowles The Naumann Group Real Estate

  lot 15 & 16 Partridge Ln, Monticello, FL 32344
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  /5

  Not Listed For Sale

  0 W Osprey Ln, Monticello, FL 32344

  0 W Osprey Ln, Monticello, FL 32344

  Last Sold Summary

  • 108 Days On Market

  Last Listing Agent Ondrea Maldonado Hamilton Realty Advisors LLC
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  /52

  $395,000

  $54K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,188 Sq Ft

  930 E Pearl St, Monticello, FL 32344

  Built between 1890–1910, this Classic Revival home sits on 1.77 acres along one of Monticello’s most admired streets and offers timeless architecture with an opportunity to restore and make it your own. The two-story layout includes 4 bedrooms and 3 bathrooms, with a circular driveway framed by boxwoods leading to a wide front porch perfect for rocking chairs. Inside, two front parlors flank the

  Rachel Sparling All Realty Services

  930 E Pearl St, Monticello, FL 32344
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  /35

  $128,903

  Sold Jul 27, 2026

  534 N Barber Hill, Lamont, FL 32336

  • 3 Beds
  • 2 Baths
  • 2,050 Sq Ft
  • Built 1980

  Last Sold Summary

  • 14% Below List Price
  • $63/SF
  • 22 Days On Market

  Current Estimated Value $215,019

  Last Listing Agent Bronson Cheeks Vylla Home

  534 N Barber Hill, Lamont, FL 32336
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  /16

  Not Listed For Sale

  157 White Oak Dr, Monticello, FL 32344

  • 4 Beds
  • 2 Baths
  • 1,801 Sq Ft
  • Built 2024

  157 White Oak Dr, Monticello, FL 32344

  Last Sold Summary

  Last Listing Agent Marylou Johnston Keller Williams Town & Country
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  /19

  $325,000

  $174K PRICE DROP

  • Land
  • 3.2 Acres
  • $101,562 per Acre

  XX Shiver Rd, Monticello, FL 32345

  Beautiful High lot at corner of Hwy 19, Shiver and Lake Rd. This listing is compilation of 3 contiguous parcels : (19-2N-5E-0140-0000-0300 and 19-2N-5E-0000-0210-0000 and 19-2N-5E-0140-0000-0170). for a total of 3.25 acres . PRIME location for multi-family, office, mixed use commercial business that needs visibility and ease of access. Utilities available- Water access to main line is Under Hwy

  Jennifer Ward Century 21 First Story

  XX Shiver Rd, Monticello, FL 32345
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  /61

  $545,000

  Sold May 13, 2026

  2184 Tram Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1998

  Last Sold Summary

  • $324/SF
  • 17 Days On Market

  Current Estimated Value $550,984

  Last Listing Agent Penny Herman Penny Herman Realty

  2184 Tram Rd, Monticello, FL 32344
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  /39

  Est $601,192

  Not Listed For Sale

  210 Deer Run, Monticello, FL 32344

  • 3 Beds
  • 2.5 Baths
  • 2,700 Sq Ft
  • Built 1988

  210 Deer Run, Monticello, FL 32344

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Jason Reese Solid Ground Real Estate Group
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  /69

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 4,762 Sq Ft

  974 Rainey Run, Monticello, FL 32344

  **Some Photos are Virtually Enhanced** Experience luxury living in the prestigious gated community of Rainey Run. This is where privacy, nature, and convenience come together on 10 breathtaking acres. Surrounded by towering hardwoods and abundant wildlife, this remarkable property offers a convenient peaceful retreat. Built in 2020, this custom home showcases quality craftsmanship with a highly

  Renee Dawkins Dawkins Realty LLC

  974 Rainey Run, Monticello, FL 32344
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  /31

  $275,000

  Sold Jun 01, 2026

  104 Pine Cone Dr, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Below List Price
  • $158/SF
  • 242 Days On Market

  Current Estimated Value $291,198

  Last Listing Agent Trevor Ann Clark Keller Williams Town & Country

  104 Pine Cone Dr, Monticello, FL 32344
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  /41

  Not Listed For Sale

  927 Quail Ln, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 2013

  927 Quail Ln, Monticello, FL 32344

  Last Sold Summary

  • 58 Days On Market

  Last Listing Agent Heather Cash Waypoint Properties

Showing Results 241 - 280, Page 7 of 18