Monticello, FL Homes

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  /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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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
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  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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 Capital City Real Estate Group

  365 S Mulberry 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 $530,252

  Last Listing Agent Lee Duggar Re/Max Professionals Realty

  70 Generation Ct, 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
• 

  

  /19

  $299,000

  $51K PRICE DROP

  • Land
  • 70.45 Acres
  • $4,244 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
• 

  

  /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
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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
• 

  

  /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
• 

  

  /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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  /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
• 

  

  /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
• 

  

  /42

  $335,000

  Sold Jun 10, 2025

  1535 Willow Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,370 Sq Ft
  • Built 2021

  Last Sold Summary

  • $245/SF
  • 6 Days On Market

  Current Estimated Value $374,139

  Last Listing Agent Chance Shutes Keller Williams Town & Country

  1535 Willow Rd, Monticello, FL 32344
• 

  

  /24

  Est $313,508

  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
• 

  

  /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 Capital City Real Estate Group

  625 E Washington St, Monticello, FL 32344
• 

  

  /36

  $285,000

  Sold Aug 08, 2025

  705 N Mulberry St, Monticello, FL 32344

  • 3 Beds
  • 2.5 Baths
  • 1,527 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $187/SF
  • 40 Days On Market

  Current Estimated Value $282,135

  Last Listing Agent Bill Lord CONSULTANTS TO HOMEBUI

  705 N Mulberry St, Monticello, FL 32344
• 

  

  /3

  Est $481,686

  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
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  /66

  $399,000

  • 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 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 outdoors in, while the solid layout offers plenty of

  Catherine Hope All Realty Services

  1012 S Main Ave, 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
• 

  

  /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
• 

  

  /38

  $449,900

  • 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
• 

  

  /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 $507,914

  Last Listing Agent Michael Schilling Hill Spooner & Elliott Inc

  79 Lakeside Rd, Monticello, FL 32344
• 

  

  /18

  Est $277,755

  Not Listed For Sale

  622 Limestone Rd, Monticello, FL 32344

  • 5 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • Built 1965

  622 Limestone Rd, Monticello, FL 32344

  Last Sold Summary

  • 52 Days On Market
• 

  

  /31

  $434,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  285 Mallard Ln, Monticello, FL 32344

  *Jefferson County peaceful country living with a waterfront backdrop! Built in 2008, this well maintained 3 bedroom, 2 bath home sits on 4.89 beautifully (mostly cleared) acres offering privacy and natural beauty backing directly up to Lloyd Lake- perfect for relaxing evenings with scenic views. Pretty rocking chair front porch as well as a screened in back porch with a propane hookup for

  Shelley Duke Red Bird Realty

  285 Mallard Ln, 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
• 

  

  /31

  Est $145,285

  Not Listed For Sale

  821 Old Lloyd Rd Unit 2, Monticello, FL 32344

  • 3 Beds
  • Built 1988

  821 Old Lloyd Rd Unit 2, Monticello, FL 32344

  Last Sold Summary

  • 223 Days On Market
• 

  

  /70

  $795,000

  • 3 Beds
  • 2.5 Baths
  • 2,160 Sq Ft

  660 Whispering Hill, Monticello, FL 32344

  Set on 18+ acres of beautifully maintained pasture, this private country property is built for both everyday living, true equestrian use or small livestock farm. The land is the star- fully fenced with new wood fencing that cleanly defines multiple pastures, a peaceful pond, and wide open space to ride, graze and enjoy. The 6-stall horse barn is ready to work with paddocks attached to each stall,

  Catherine Hope All Realty Services

  660 Whispering Hill, Monticello, FL 32344
• 

  

  /26

  $130,000

  Sold Jul 25, 2025

  00 Cardinal Ln, Monticello, FL 32344

  • Land
  • 14.1 Acres
  • $9,220 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 175 Days On Market

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

  00 Cardinal Ln, Monticello, FL 32344
• 

  

  /5

  Est $152,212

  Not Listed For Sale

  220 Horseshoe Rd, Monticello, FL 32344

  • 3 Beds
  • 1 Bath
  • 1,314 Sq Ft
  • Built 1977

  220 Horseshoe Rd, Monticello, FL 32344

  Last Sold Summary

  • 36 Days On Market
• 

  

  /31

  $625,000

  • 4 Beds
  • 3 Baths
  • 2,716 Sq Ft

  140 Shumard Ct, Monticello, FL 32344

  Discover this stunning 2,600+ sqft home built in 2021, offering the perfect blend of quiet country living and modern convenience. Adjoinging additional lot can also be purchased! Features include: 4 spacious bedrooms and 3 full bathrooms 2 master bedrooms located downstairs Dedicated office/bonus room – ideal for work or hobbies Modern kitchen and open living spaces Attached 2-car garage Just

  Caleb Stephens Silo Hill Properties

  140 Shumard Ct, Monticello, FL 32344
• 

  

  /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

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