Jefferson County, FL Homes

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  /5

  Not Listed For Sale

  394 E Osprey Ln, Monticello, FL 32344

  394 E Osprey Ln, Monticello, FL 32344

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Shannon Pararo Big Fish Real Estate Services
• 

  

  

  /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
• 

  

  

  /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 $523,649

  Last Listing Agent Lee Duggar Re/Max Professionals Realty

  70 Generation 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

  Last Listing Agent Amber McKinney Hamilton Realty Advisors LLC
• 

  

  

  /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
• 

  

  /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 $532,180

  Last Listing Agent Bonnie Fowler Armor Realty, Inc

  1923 Whitehouse Rd, Monticello, FL 32344
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  /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

  Last Listing Agent Kevin Davis The Naumann Group Real Estate
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  /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 Bespoke Realty of Tallahassee

  625 E Washington 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
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  /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

  Last Listing Agent Othell Broger Broger Real Estate Services
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  /11

  $45,000

  • Land
  • 2.5 Acres
  • $18,000 per Acre

  1 W Meadow Rd, Monticello, FL 32344

  All Offers considered..2.5 Acres of land, partially cleared for home-site. Private quiet road. All high and dry ready to build your homestead. mobile homes okay. Close to aucilla river. Convenient to Monticello, FL and Thomasville Ga. Valdosta and Tallahassee 45 minutes away. Horse Friendly area. Owner financing options available.

  Starbuck Rissman Steve C. Walker Realty, LLC

  1 W Meadow Rd, Monticello, FL 32344
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  /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
• 

  

  /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

  Last Listing Agent Steven Koleno Beycome of Florida LLC
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  /66

  $379,000

  $20K PRICE DROP Under Contract

  • 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 HVAC June 2026 with 10 year parts warranty, plus 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

  Catherine Hope All Realty Services

  1012 S Main Ave, Monticello, FL 32344
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  /29

  $600,000

  Sold Aug 03, 2026

  180 Cooper Rd, Monticello, FL 32344

  • 2 Beds
  • 2 Baths
  • 1,592 Sq Ft
  • Built 1984

  Last Sold Summary

  • 4% Below List Price
  • $377/SF
  • 25 Days On Market

  Current Estimated Value $615,586

  Last Listing Agent Hines Boyd FL-GA Realty & Auction

  180 Cooper Rd, Monticello, FL 32344
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  /42

  Est $873,301

  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

  Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc
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  /2

  $125,000

  • Land
  • 5.96 Acres
  • $20,973 per Acre

  0 Eastwood Unit 402606, Monticello, FL 32344

  Back on the market - Discover the perfect place to build your dream home on this beautiful nearly 6-acre parcel! Enjoy the peace and privacy of country living with the convenience of being just minutes from the interstate and a short drive to Tallahassee. With plenty of room for your custom home, workshop, gardens, or recreational space, the possibilities are endless! Whether you’re looking to

  D. Scott Kilgore Superior Realty Group LLC

  0 Eastwood Unit 402606, Monticello, FL 32344
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  /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
• 

  

  /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

  Last Listing Agent Keith Gordon Get More Offers
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  /38

  $429,900

  $20K PRICE DROP

  • 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
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  /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 $426,716

  Last Listing Agent Michael Schilling Hill Spooner & Elliott Inc

  79 Lakeside Rd, Monticello, FL 32344
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  /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

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

  

  /24

  $298,900

  New Construction

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

  1070 Partridge Ln, Monticello, FL 32344

  Currently under construction. Interior pictures are from a previous model home. Approximately 60 days until completion. Home qualifies for USDA financing.

  Steve Walker Steve C. Walker Realty, LLC

  1070 Partridge Ln, Monticello, FL 32344
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  /60

  $550,000

  Sold Aug 04, 2026

  925 Hiawatha Farms Rd, Monticello, FL 32344

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft
  • Built 2012

  Last Sold Summary

  • $260/SF
  • 66 Days On Market

  Current Estimated Value $555,534

  Last Listing Agent JoAnn Jacobs Coldwell Banker Hartung

  925 Hiawatha Farms Rd, Monticello, FL 32344
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  /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

  Last Listing Agent Susan Byler Keller Williams Town & Country
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  /61

  $1,100,000

  Under Contract

  • 3 Beds
  • 3 Baths
  • 2,815 Sq Ft

  458 Watermill Rd, Monticello, FL 32344

  Country Living at Its Finest! This stunning 2,800-square-foot 3-bedroom, 3-bath home is nestled on nearly 30 breathtaking acres. Offering the perfect blend of comfort, beauty, and functionality, this exceptional property is ideal for those seeking peaceful country living without sacrificing modern amenities. Inside, you’ll find spacious living areas with high ceilings, an eat-in kitchen, family

  D. Scott Kilgore Superior Realty Group LLC

  458 Watermill Rd, 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
• 

  

  /24

  Est $301,081

  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

  Last Listing Agent Jay Lattay KeySouth Real Estate Group
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  /37

  $269,900

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  60 Bob White Trail, Monticello, FL 32344

  Tucked behind a gated entrance and nestled on 5.54 acres, this property offers the privacy, space, and freedom that is hard to find at this price point. With no HOA, you'll have the flexibility to enjoy true country living with plenty of room for horses, livestock, RVs, trailers, ATVs, UTVs, and more. Upon arrival, you're greeted by a large, open parking area with ample space for vehicles,

  Kyle Footman Coldwell Banker Hartung

  60 Bob White Trail, 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
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  /3

  Est $501,243

  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

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

  

  /29

  $164,900

  • 4 Beds
  • 2 Baths
  • 1,656 Sq Ft

  75 E Turkey Roost Rd, Greenville, FL 32331

  Nestled on 5.42 peaceful acres with a scenic pond, this 4-bedroom, 2-bath manufactured home offers the perfect opportunity to enjoy country living while adding your own personal touch. Whether you’re looking for a family home, or a quiet retreat, this property has plenty to offer. Inside, you’ll find a spacious floor plan featuring a huge primary suite complete with its own dedicated mini-split

  E. Bradley Vollertsen Advanced Real Estate Sales

  75 E Turkey Roost Rd, Greenville, FL 32331
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  /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
• 

  

  /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

  Last Listing Agent Stephen Hachey Flat Fee MLS Realty
• 

  

  /61

  $539,000

  $11K PRICE DROP Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,873 Sq Ft

  761 Hawkins Rd, Monticello, FL 32344

  This one truly has it all! Nestled on 5+ private acres in beautiful Monticello, Florida, this 4-bedroom, 2.5-bath home offers the perfect blend of comfort, privacy, and charm. Step inside to a spacious split floor plan featuring 10-foot tray ceilings, real hardwood floors, a cozy wood-burning fireplace, and abundant natural light throughout. The beautifully updated kitchen features granite

  Kayla Meadows Keller Williams Town & Country

  761 Hawkins Rd, 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
• 

  

  /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

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

  /2

  $150,000

  Under Contract

  • Land
  • 9.96 Acres
  • $15,060 per Acre

  0 Watermill Rd Unit 403463, Monticello, FL 32344

  Beautiful country property on nearly 10 acres to build your dream home on.

  D. Scott Kilgore Superior Realty Group LLC

  0 Watermill Rd Unit 403463, 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
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  /42

  Est $351,541

  Not Listed For Sale

  580 Holly Rd, Monticello, FL 32344

  • 4 Beds
  • 2 Baths
  • 1,551 Sq Ft
  • Built 2012

  580 Holly Rd, Monticello, FL 32344

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Anthony Gifford Pointer Realty

Showing Results 121 - 160, Page 4 of 18