Jefferson County, FL Homes

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  /70

  $2,735,850

  $50K PRICE DROP

  • 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 70 beautiful acres. Only 15 minutes to Whole foods & trader Joe's 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

  

  Chance Shutes

  Keller Williams Town & Country

  305 Old Lloyd Rd, Monticello, FL 32344
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  /3

  $258,900

  Sold Jul 09, 2026

  660 N Cherry St, Monticello, FL 32344

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 2026

  Last Sold Summary

  • $237/SF
  • 18 Days On Market

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

  660 N Cherry St, Monticello, FL 32344
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  /20

  Not Listed For Sale

  Lot 4 Watermill Rd, Monticello, FL 32344

  Lot 4 Watermill Rd, Monticello, FL 32344

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Sarah McKinzie Hum Real Estate
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  /32

  $259,000

  $10K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,338 Sq Ft

  1511 Spring Hollow Dr, Monticello, FL 32344

  Charming home on large .87 acre lot in established subdivision. Sunporch overlooks wooded back yard, a nature lovers paradise. Open floor plan, kitchen/dining/living room combination. 2 car garage with breezeway to the home.

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  1511 Spring Hollow Dr, Monticello, FL 32344
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  /28

  $375,000

  Sold Jul 30, 2026

  1205 E Pearl St, Monticello, FL 32344

  • 3 Beds
  • 2.5 Baths
  • 2,373 Sq Ft
  • Built 1956

  Last Sold Summary

  • 11% Below List Price
  • $158/SF
  • 143 Days On Market

  Current Estimated Value $333,910

  Last Listing Agent Brian Bachman Kelly & Kelly Properties, Inc

  1205 E Pearl St, Monticello, FL 32344
• 

  

  /20

  Not Listed For Sale

  Lot 3 Watermill Rd, Monticello, FL 32344

  Lot 3 Watermill Rd, Monticello, FL 32344

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Sarah McKinzie Hum Real Estate
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  /55

  $765,000

  • 3 Beds
  • 2.5 Baths
  • 2,436 Sq Ft

  9901 Gamble Rd, Monticello, FL 32344

  PRIVATE 20-ACRE ESTATE MINUTES FROM TALLAHASSEE - TRAILS, WILDLIFE, PASTURE & CUSTOM HOME (ADJOINING 21 ACRES AVAILABLE-MLS#400837) Nestled among majestic oaks and rolling countryside, this exceptional estate offers a rare combination of privacy, natural beauty and comfortable country living. Beyond the gated entrance lies a beautiful setting of open land, mature trees, and abundant wildlife,

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  9901 Gamble Rd, Monticello, FL 32344
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  /19

  $135,000

  Sold Feb 16, 2026

  XX Foggy Ln, Monticello, FL 32344

  • Land
  • 5.25 Acres
  • $25,714 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Cole Davis The Naumann Group Real Estate

  XX Foggy Ln, Monticello, FL 32344
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  /7

  Not Listed For Sale

  0 Taylor Rd Unit 384618, Monticello, FL 32344

  0 Taylor Rd Unit 384618, Monticello, FL 32344

  Last Sold Summary

  • 102 Days On Market

  Last Listing Agent Kevin Davis The Naumann Group Real Estate
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  /19

  $239,000

  • 3 Beds
  • 1 Bath
  • 1,164 Sq Ft

  220 Eaton St, Monticello, FL 32344

  Very convenient location in the heart of Monticello. Excellent condition. Very good condition, new roof, new windows, newer flooring throughout. 10X12 storage shed.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  220 Eaton St, Monticello, FL 32344
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  /43

  $285,000

  Sold Feb 18, 2026

  425 N Mulberry St, Monticello, FL 32344

  • 5 Beds
  • 2 Baths
  • 3,320 Sq Ft
  • Built 1920

  Last Sold Summary

  • 10% Below List Price
  • $86/SF
  • 125 Days On Market

  Current Estimated Value $320,443

  Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

  425 N Mulberry St, Monticello, FL 32344
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  /40

  Not Listed For Sale

  79 Mire Ct, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,806 Sq Ft
  • Built 2025

  79 Mire Ct, Monticello, FL 32344

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Amber McKinney Hamilton Realty Advisors LLC
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  /4

  $130,000

  • Land
  • 9.96 Acres
  • $13,052 per Acre

  00 Mallard Blue Jay Ln Unit 2/3, Monticello, FL 32344

  The listing contains (2) adjacent raw land parcels in the Lloyd Acres Subdivision = 9.96 acres total. See parcel IDs: 18-1N-4E-0113-000C-0010 (6.41 acres; Mallard Lane) + 18-1N-4E-0112-000C-0050 (3.55 acres; Bluejay Rd). Look for real estate signs (2) to help identify the acreage for sale. The property is zoned Residential-01 (1 home/1 acre), making it a great opportunity for someone wanting to

  

  Brenna Kelly-Ward

  Kelly & Kelly Properties, Inc

  00 Mallard Blue Jay Ln Unit 2/3, Monticello, FL 32344
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  /50

  $860,000

  Sold Dec 30, 2025

  240 Valley View Ct, Monticello, FL 32344

  • 5 Beds
  • 3 Baths
  • 3,656 Sq Ft
  • Built 2004

  Last Sold Summary

  • 18% Below List Price
  • $235/SF
  • 62 Days On Market

  Current Estimated Value $901,345

  Last Listing Agent Hettie Spooner Hill Spooner & Elliott Inc

  240 Valley View Ct, Monticello, FL 32344
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  /30

  Est $400,581

  Not Listed For Sale

  460 W Osprey Ln, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1991

  460 W Osprey Ln, Monticello, FL 32344

  Last Sold Summary

  • 72 Days On Market

  Last Listing Agent Hines Boyd FL-GA Realty & Auction
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  /45

  $1,805,000

  • Land
  • 192 Acres
  • $9,401 per Acre

  Vacant N Salt Rd, Monticello, FL 32344

  192 Acre Organic Cattle Farm in Jefferson County, Florida192 acre cattle farm located in beautiful Jefferson County, FloridaCertified organic operation for 20+ years with a long-standing history of sustainable land stewardshipFully fenced and cross-fenced for efficient cattle rotation and livestock managementImproved pastureland ideal for cattle,

  

  Ben Jones

  Mossy Oak Properties Southern Land and Homes, LLC

  Vacant N Salt Rd, Monticello, FL 32344
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  /2

  $90,000

  Sold Mar 30, 2026

  890 Shady Ln, Monticello, FL 32344

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • Built 1978

  Last Sold Summary

  • $69/SF
  • 0 Days On Market

  Current Estimated Value $97,510

  Last Listing Agent Shanna D'Attile Keller Williams Town & Country

  890 Shady Ln, Monticello, FL 32344
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  /42

  Est $519,645

  Not Listed For Sale

  761 Tyson Rd, Lamont, FL 32336

  • 3 Beds
  • 2 Baths
  • 1,952 Sq Ft
  • Built 2022

  761 Tyson Rd, Lamont, FL 32336

  Last Sold Summary

  • 145 Days On Market

  Last Listing Agent Paul Fenstermaker Fenstermaker & Associates Real
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  /30

  $149,900

  $25K PRICE DROP Under Contract

  • 3 Beds
  • 1 Bath
  • 1,662 Sq Ft

  167 Phelps Rd, Lamont, FL 32336

  Charming 3BR/1BA home with incredible potential, nestled on a gorgeous and private one acre lot with no neighbors in sight. The property is filled with beautiful Camelia trees, creating a serene and picturesque setting. A newer workshop sits out back - perfect for hobbies, storage, or projects. Major update includes a 2025 metal roof. Crawlspace inspection has identified needed repairs to

  

  Carmen Moloney

  McClellan Realty, LLC

  167 Phelps Rd, Lamont, FL 32336
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  /20

  $62,500

  Sold Oct 07, 2025

  195 E Meadow Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,836 Sq Ft
  • Built 1999

  Last Sold Summary

  • 55% Below List Price
  • $34/SF
  • 99 Days On Market

  Current Estimated Value $238,047

  Last Listing Agent Chelsey Hough Keller Williams Town & Country

  195 E Meadow Rd, Monticello, FL 32344
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  /25

  Not Listed For Sale

  10 Spruce Cir, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,601 Sq Ft
  • Built 2025

  10 Spruce Cir, Monticello, FL 32344

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Tiffany Kasdorf Kozloski Realty, LLC
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  /50

  $510,000

  $40K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,134 Sq Ft

  121 Shumard Ct, Monticello, FL 32344

  Exceptionally maintained , this turn key 2022 farmhouse-style home is located in the sought after Crooked Creek area.Seller is motivated! This home is ready for immediate occupancy and includes whole house generator still under warranty. This spacious 2134 sq ft home features 4 bedrooms and 2.5 baths on a generous .85 acre lot, ideally situated on a quiet cul-de-sac on the west side of

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  121 Shumard Ct, Monticello, FL 32344
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  /14

  $294,900

  Sold Apr 27, 2026

  1090 Partridge Ln, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,351 Sq Ft
  • Built 2026

  Last Sold Summary

  • $218/SF
  • 50 Days On Market

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

  1090 Partridge Ln, Monticello, FL 32344
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  /29

  Not Listed For Sale

  Vacant Hartsfield Rd, Monticello, FL 32344

  Vacant Hartsfield Rd, Monticello, FL 32344

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Ben Jones Southern Land & Homes
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  /2

  $139,000

  • Land
  • 5 Acres
  • $27,800 per Acre

  TBD Orchard Ln, Monticello, FL 32344

  Great Location in Western Jefferson County offering country living with the convenience of Tallahassee only minutes away. Wooded 5 acres on private lane. Restricted for site built homes with minimum of 1200 sq ft heated and cooled. Adjoining 5 available for sale.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD Orchard Ln, Monticello, FL 32344
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  /31

  $85,000

  Sold Jan 16, 2026

  572 Deerwood Blvd, Greenville, FL 32331

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2000

  Last Sold Summary

  • 19% Below List Price
  • $63/SF
  • 126 Days On Market

  Last Listing Agent Crystal Bochnia Madison Realty Group, LLC

  572 Deerwood Blvd, Greenville, FL 32331
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  /42

  Not Listed For Sale

  0 Fen Ct, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,807 Sq Ft
  • Built 2025

  0 Fen Ct, Monticello, FL 32344

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Amber McKinney Hamilton Realty Advisors LLC
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  /41

  $499,000

  $51K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,268 Sq Ft

  398 Tecumseh Rd, Monticello, FL 32344

  Charming Cape Cod-style home tucked away on 5 acres just minutes to downtown Monticello. This one owner home has been lovingly maintained and reflects years of care and pride of ownership. With over 2200 square feet of living space, the home offers a comfortable layout. The main floor features three bedrooms, one bath, a welcoming living room with a gas fireplace, dining area, kitchen and a

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  398 Tecumseh Rd, Monticello, FL 32344
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  /26

  $370,000

  Sold Mar 12, 2026

  298 W 12th Dr, Greenville, FL 32331

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $193/SF
  • 39 Days On Market

  Current Estimated Value $373,800

  Last Listing Agent Jay Finlayson Finlayson Realty Inc.

  298 W 12th Dr, Greenville, FL 32331
• 

  

  /3

  Not Listed For Sale

  000 Steen Rd, Monticello, FL 32344

  000 Steen Rd, Monticello, FL 32344

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Sarah Scott Coldwell Banker Hartung
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  /5

  $199,000

  • Land
  • 5.03 Acres
  • $39,563 per Acre

  TBD W Washington, Monticello, FL 32344

  Fronting on Hwy-90 this high elevation lot is lightly wooded. Some restrictions apply.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD W Washington, Monticello, FL 32344
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  /29

  $260,000

  Sold Jul 31, 2026

  425 Carolina St, Monticello, FL 32344

  • 4 Beds
  • 2 Baths
  • 1,448 Sq Ft
  • Built 1968

  Last Sold Summary

  • 7% Below List Price
  • $180/SF
  • 22 Days On Market

  Current Estimated Value $258,989

  Last Listing Agent Shanna D'Attile Keller Williams Town & Country

  425 Carolina St, Monticello, FL 32344
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  /42

  Est $211,078

  Not Listed For Sale

  285 E 10th Way, Greenville, FL 32331

  • 4 Beds
  • 2 Baths
  • 2,088 Sq Ft
  • Built 2015

  285 E 10th Way, Greenville, FL 32331

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Michael Phillips Engel & Völkers Tallahassee
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  /36

  $584,000

  • 3 Beds
  • 3.5 Baths
  • 2,148 Sq Ft

  8250 Waukeenah Hwy, Monticello, FL 32344

  Enjoy two private year around spring fed ponds! Escape to your own private sanctuary on 30 breathtaking acres where nature, privacy, and craftsmanship come together. This custom-built retreat features soaring vaulted ceilings, expansive windows, & French doors- blurring the line between indoors and out, flooding every room with natural light and serene views. 2 Bed, 2.5 Bath, thoughtfully

  

  Bhishma Benedict

  FLORIDA HOMES REALTY & MORTGAGE GVILLE

  8250 Waukeenah Hwy, Monticello, FL 32344
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  /14

  $35,000

  Sold Aug 05, 2026

  0 Quail Ln Unit 400884, Monticello, FL 32344

  • Land
  • 1.01 Acres
  • $34,653 per Acre

  Last Sold Summary

  • 5% Below List Price
  • 7 Days On Market

  Last Listing Agent Callie Rhoads The Naumann Group Real Estate

  0 Quail Ln Unit 400884, Monticello, FL 32344
• 

  

  /10

  Not Listed For Sale

  0 Tram Rd Unit 381553, Monticello, FL 32344

  0 Tram Rd Unit 381553, Monticello, FL 32344

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Hettie Spooner Hill Spooner & Elliott Inc
• 

  

  /46

  $325,000

  • 4 Beds
  • 2 Baths
  • 2,304 Sq Ft

  947 Piney Woods Rd, Monticello, FL 32344

  Charming 2022 Mobile Home on 5 Peaceful Acres A rare blend of modern comfort and wide-open space, this 2022 mobile home sits on 5+ acres—perfect for anyone craving privacy, freedom, and room to grow. Whether you dream of a hobby farm, a quiet country retreat, or simply a place with no close neighbors, this property delivers. Embrace freedom of country living with the convenience of a modern home.

  

  Brian Bachman

  Kelly & Kelly Properties, Inc

  947 Piney Woods Rd, Monticello, FL 32344
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  /34

  $190,000

  Sold Jun 29, 2026

  28 Kameron Dr, Monticello, FL 32344

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Built 2022

  Last Sold Summary

  • 3% Above List Price
  • $238/SF
  • 44 Days On Market

  Current Estimated Value $186,419

  Last Listing Agent Chip Williams Keller Williams Town & Country

  28 Kameron Dr, Monticello, FL 32344
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  /37

  Not Listed For Sale

  183 Chittling Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 2001

  183 Chittling Rd, Monticello, FL 32344

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Catherine Hope All Realty Services
• 

  

  /6

  $50,000

  • Land
  • 26,571 Sq Ft
  • $81,967 per Acre

  790 Rd, Lamont, FL 32336

  Beautiful building lot, ideal for home or mobile home. Existing doublewide on the property in poor condition. Do not enter mobile home due to condition. The home may be repairable for the right buyer, roof has been leaking so it will be a major repair.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  790 Rd, Lamont, FL 32336

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