Monticello, FL Homes

• 

  

  

  /54

  $105,000

  Sold Jun 17, 2026

  12447 Gamble Rd, Monticello, FL 32344

  • 2 Beds
  • 2 Baths
  • 1,792 Sq Ft
  • Built 1930

  Last Sold Summary

  • 38% Below List Price
  • $59/SF
  • 236 Days On Market

  Current Estimated Value $118,293

  Last Listing Agent Catherine Hope All Realty Services

  12447 Gamble Rd, Monticello, FL 32344
• 

  

  

  /6

  Not Listed For Sale

  0 Barnes Rd Unit 380665, Monticello, FL 32344

  0 Barnes Rd Unit 380665, Monticello, FL 32344

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent H. Trey Hough Armor Realty, Inc
• 

  

  

  /56

  $1,175,000

  • 3 Beds
  • 2 Baths
  • 2,612 Sq Ft

  1590 Tyson Rd, Monticello, FL 32344

  Experience the beauty and tranquility of North Florida living on this stunning estate located just south of Monticello with an easy commute to Tallahassee. This remarkable property features a mature pecan grove, two scenic ponds, along with a creek and open pasture perfect for horses or livestock. The centerpiece of the property is a beautifully crafted home filled with warmth, charm, and custom

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  1590 Tyson 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 $240,866

  Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

  495 N Cherry Ct, Monticello, FL 32344
• 

  

  

  /3

  Not Listed For Sale

  4019 Ashville Hwy Unit o, Monticello, FL 32344

  4019 Ashville Hwy Unit o, Monticello, FL 32344

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Sarah Scott Coldwell Banker Hartung
• 

  

  /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 Bespoke Realty of Tallahassee

  365 S Mulberry St, 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 $909,245

  Last Listing Agent Kelly Vinson Keller Williams Town & Country

  237 Valley View Ct, Monticello, FL 32344
• 

  

  /23

  Not Listed For Sale

  36 Mossy Oak Ln, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,957 Sq Ft
  • Built 2024

  36 Mossy Oak Ln, Monticello, FL 32344

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Chance Shutes Keller Williams Town & Country
• 

  

  /19

  $281,800

  $68K PRICE DROP

  • Land
  • 70.45 Acres
  • $4,000 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
• 

  

  /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 $333,466

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

  864 Ashville Hwy, Monticello, FL 32344
• 

  

  /40

  Est $296,915

  Not Listed For Sale

  185 Main St, Monticello, FL 32344

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

  185 Main St, Monticello, FL 32344

  Last Sold Summary

  • 93 Days On Market

  Last Listing Agent Lee Hall Bespoke Realty of Tallahassee
• 

  

  /7

  $109,000

  • Land
  • 5 Acres
  • $21,800 per Acre

  130 Sweetfield Rd, Monticello, FL 32344

  Mobile-home-friendly property with a cleared homesite and an existing well, septic system, and electrical service already on the property. Seller financing is available. Conveniently located near I-10 and approximately 30 minutes from Tallahassee. Bring your home plans and enjoy a quiet country setting with room for animals, gardening, outdoor projects, and additional storage. Fence the property

  Moe Mossa Savvy Avenue, LLC

  130 Sweetfield Rd, Monticello, FL 32344
• 

  

  /24

  $167,000

  Sold Jul 16, 2026

  963 Quail Ln, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1999

  Last Sold Summary

  • 12% Below List Price
  • $116/SF
  • 116 Days On Market

  Last Listing Agent Van Drake Tallahassee Land Company

  963 Quail Ln, 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

  Last Listing Agent Tiffany Kasdorf Kozloski Realty, LLC
• 

  

  /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
• 

  

  /70

  $465,000

  Sold Jun 26, 2026

  3140 W Washington Hwy, Monticello, FL 32344

  • 4 Beds
  • 3.5 Baths
  • 4,200 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Above List Price
  • $111/SF
  • 3 Days On Market

  Current Estimated Value $600,634

  Last Listing Agent Nancy Stedman Coldwell Banker Hartung

  3140 W Washington Hwy, Monticello, FL 32344
• 

  

  /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

  Last Listing Agent Jackie Austin Shamrock Professionals Realty
• 

  

  /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
• 

  

  /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 $954,565

  Last Listing Agent Michele Arceneaux Kelly & Kelly Properties, Inc

  525 Taylor 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

  Last Listing Agent Kevin Davis The Naumann Group Real Estate
• 

  

  /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
• 

  

  /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
• 

  

  /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

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

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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

Showing Results 81 - 120, Page 3 of 18