Monticello, FL Homes

• 

  

  

  /16

  $40,000

  $25K PRICE DROP Under Contract

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft

  980 Mays St, Monticello, FL 32344

  "Buy Now and Wait" a little while the attorney finishes up the Probate proceedings underway. Cannot close until court approval however you can go ahead and grab it now. Concrete Block 2/1 Home less than a mile from downtown Monticello! This quaint 888 sq ft home sits under a metal roof and only requires your vision and a little effort to become a superb starter home or investment opportunity.

  Ben Marinelli All Realty Services

  980 Mays St, Monticello, FL 32344
• 

  

  

  /7

  $95,000

  Sold Aug 01, 2025

  0 Taylor Rd Unit 384618, Monticello, FL 32344

  • Land
  • 5.17 Acres
  • $18,375 per Acre

  Last Sold Summary

  • 21% Below List Price
  • 102 Days On Market

  Last Listing Agent Kevin Davis The Naumann Group Real Estate

  0 Taylor Rd Unit 384618, Monticello, FL 32344
• 

  

  

  /4

  Not Listed For Sale

  XXX Shiver, Monticello, FL 32344

  XXX Shiver, Monticello, FL 32344

  Last Sold Summary

  • 204 Days On Market
• 

  

  

  /54

  $135,000

  $34K PRICE DROP Under Contract

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

  12447 Gamble Rd, Monticello, FL 32344

  Seller Ready to Not be the Owner Anymore! Corner Lot! This 2 bedroom (could be a 3rd Bdrm however the 3rd bedroom does not have a closet but most 1930's homes did not have closets), 2 bathroom home offers 1,792 sq ft of living on 1 acre in Wacissa, Florida, just 1 minute from the Wacissa River headwaters (first magnitude Spring) and boat launch in Monticello, Jefferson County, Florida. It’s an

  Catherine Hope All Realty Services

  12447 Gamble Rd, Monticello, FL 32344
• 

  

  

  /10

  $220,000

  Sold Aug 26, 2025

  1400 Gamble Rd, Monticello, FL 32344

  • Land
  • 7 Acres
  • $31,429 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 119 Days On Market

  Current Estimated Value $227,405

  Last Listing Agent Kenneth Ayers Primesouth Fezler, Russell and

  1400 Gamble Rd, Monticello, FL 32344
• 

  

  /24

  Not Listed For Sale

  00 Valley View Rd, Monticello, FL 32344

  00 Valley View Rd, Monticello, FL 32344

  Last Sold Summary

  • 42 Days On Market
• 

  

  /24

  $174,900

  $15K PRICE DROP Under Contract

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

  963 Quail Ln, Monticello, FL 32344

  Great location for this property in Lloyd Acres. The property has 2.26 acres of partially wooded area. The property consists of the single family home, detached garage/carport/workshop and a singlewide mobile home. The vinyl sided home will need some repair and updating but has tremendous potential. The detached garage is large with 2 stalls. The mobile home is in need of a total renovation (or

  Van Drake Tallahassee Land Company

  963 Quail Ln, Monticello, FL 32344
• 

  

  /42

  $165,000

  Sold Feb 27, 2026

  2436 N Jefferson Hwy, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 2,390 Sq Ft
  • Built 1951

  Last Sold Summary

  • 38% Below List Price
  • $69/SF
  • 285 Days On Market

  Current Estimated Value $249,048

  Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

  2436 N Jefferson Hwy, Monticello, FL 32344
• 

  

  /5

  Not Listed For Sale

  0 E Bear Hollow Trail Unit 373231, Monticello, FL 32331

  0 E Bear Hollow Trail Unit 373231, Monticello, FL 32331

  Last Sold Summary

  • 57 Days On Market
• 

  

  /27

  $227,900

  • 3 Beds
  • 2 Baths
  • 1,323 Sq Ft

  120 Larry's Ln, Monticello, FL 32344

  Recently renovated home on large lot out in the country. Quiet living at it's best only a couple miles from I-10. Metal roof, new carpet and LVP flooring, fresh paint and fixtures. Home is in great shape and move in ready.

  Randy Kamenicky Mainstreet Realty Of Tallahass

  120 Larry's Ln, Monticello, FL 32344
• 

  

  /3

  $94,500

  Sold Sep 05, 2025

  0 W Osprey Ln Unit 381026, Monticello, FL 32344

  • Land
  • 20 Acres
  • $4,725 per Acre

  Last Sold Summary

  • 32% Below List Price
  • 222 Days On Market

  Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

  0 W Osprey Ln Unit 381026, Monticello, FL 32344
• 

  

  /8

  Not Listed For Sale

  0 Bassett Dairy Rd Unit 373105, Monticello, FL 32344

  0 Bassett Dairy Rd Unit 373105, Monticello, FL 32344

  Last Sold Summary

  • 284 Days On Market
• 

  

  /42

  $225,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,496 Sq Ft

  263 Dove Ln, Monticello, FL 32344

  3-bedroom, 2-bath modular home situated on over 5 private acres, offering the perfect blend of comfort and peaceful country living. This well-maintained home features a desirable split floor plan with a spacious eat-in kitchen, ample cabinetry, and a separate family room centered around a beautiful wood-burning fireplace. The generously sized primary suite includes a large walk-in closet and an

  Leanne Groom The Naumann Group Real Estate

  263 Dove Ln, Monticello, FL 32344
• 

  

  /41

  $336,000

  Sold Jun 23, 2025

  1600 Sweetbay Ct, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,555 Sq Ft
  • Built 2021

  Last Sold Summary

  • $216/SF
  • 33 Days On Market

  Last Listing Agent Amber Renaud The Nova Group Realty

  1600 Sweetbay Ct, Monticello, FL 32344
• 

  

  /14

  Est $379,043

  Not Listed For Sale

  4131 Ashville Hwy, Monticello, FL 32344

  • 2 Beds
  • Built 1940

  4131 Ashville Hwy, Monticello, FL 32344

  Last Sold Summary

  • 16 Days On Market
• 

  

  /31

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  1164 Oaklands Plantation Rd, Monticello, FL 32344

  Nestled on 5.5 peaceful, private acres, this charming 3-bedroom, 2-bath home offers the perfect blend of space, comfort, and tranquility. Step inside to an open floor plan designed for both everyday living and effortless entertaining, with a seamless flow between the living, dining, and kitchen areas. The spacious primary suite is a true retreat, featuring a large en-suite bathroom complete with

  Norris Bishop Norris Bishop Realty, LLC

  1164 Oaklands Plantation Rd, Monticello, FL 32344
• 

  

  /33

  $140,000

  Sold Jan 09, 2026

  720A Indian Hills Rd, Monticello, FL 32344

  • Land
  • 10.62 Acres
  • $13,183 per Acre

  Last Sold Summary

  • 26% Below List Price
  • 131 Days On Market

  Last Listing Agent Alicia Radtke All Realty Services

  720A Indian Hills Rd, Monticello, FL 32344
• 

  /2

  Not Listed For Sale

  B Salt Rd, Monticello, FL 32344

  B Salt Rd, Monticello, FL 32344

  Last Sold Summary

  • 86 Days On Market
• 

  

  /51

  $325,000

  Under Contract

  • 4 Beds
  • 3 Baths
  • 2,223 Sq Ft

  155 E Seminole Ave, Monticello, FL 32344

  Set along one of Monticello’s main routes, this 1950s home offers a rare chance to create something truly your own—whether that’s a residence, a business, or a thoughtful mix of both, with flexible Business/Residential zoning already in place. Sitting on 0.60 acres with over 2,200 square feet, the layout is surprisingly adaptable, with 4 bedrooms and 3 full bathrooms, including multiple ensuite

  Catherine Hope All Realty Services

  155 E Seminole Ave, Monticello, FL 32344
• 

  

  /63

  $500,000

  Sold Oct 24, 2025

  282 Long Leaf Dr, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 2,170 Sq Ft
  • Built 1998

  Last Sold Summary

  • 4% Below List Price
  • $230/SF
  • 95 Days On Market

  Current Estimated Value $495,722

  Last Listing Agent Catherine Hope All Realty Services

  282 Long Leaf Dr, Monticello, FL 32344
• 

  /2

  Not Listed For Sale

  A Salt Rd, Monticello, FL 32344

  A Salt Rd, Monticello, FL 32344

  Last Sold Summary

  • 86 Days On Market
• 

  

  /17

  $349,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,502 Sq Ft

  406 Robin Rd, Monticello, FL 32344

  This charming 3-bedroom, 2-bath residence offers spacious living with vaulted ceilings, all nestled on five acres of private land. The property features a new roof for peace of mind, and the large deck is perfect for outdoor entertaining.This home also has a large unfinished basement to fit many of needs. The acreage is divided into 4 lots, providing plenty of space and potential. Located on a

  Caleb Stephens Silo Hill Properties

  406 Robin Rd, Monticello, FL 32344
• 

  

  /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
• 

  

  /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
• 

  

  /22

  $185,000

  Under Contract

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  165 N Water St, Monticello, FL 32344

  ACCEPTING BACK UPS! Step into timeless charm with modern comfort at 165 N Water St in Monticello—a beautifully renovated 2-bedroom, 1-bathroom home nestled in the heart of the historic district. Just a short distance to downtown, you’ll enjoy easy access to local shops, dining, and the unique character that makes Monticello so special. This bright and airy home features updated windows that fill

  Sandy Ferrera All County Suncoast Property

  165 N Water St, Monticello, FL 32344
• 

  

  /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 $565,961

  Last Listing Agent Brett Miller Legacy Pro Real Estate Group

  44 S Ojibwa Rd, Monticello, FL 32344
• 

  

  /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
• 

  

  /20

  $100,000

  • 3 Beds
  • 1 Bath
  • 1,864 Sq Ft

  340 S Waukeenah St, Monticello, FL 32344

  They don’t build them like they used to! This historic 1900 home located in downtown Monticello sits on nearly a half-acre lot and is full of timeless character waiting to be restored. Featuring original hardwood floors throughout most of the home, beadboard walls, 9+ foot ceilings, and original glass windows, this property offers the charm and craftsmanship so many buyers desire. Spacious

  Alicia Radtke All Realty Services

  340 S Waukeenah St, Monticello, FL 32344
• 

  

  /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 CONSULTANTS TO HOMEBUI

  000 Barnes Rd, Monticello, FL 32344
• 

  

  /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
• 

  

  /37

  $285,000

  Under Contract

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

  60 Bob White Trail, Monticello, FL 32344

  Tucked behind a gated entrance and surrounded by 5.54 acres of open space, this property offers the kind of privacy and freedom that is hard to find at this price point. With no HOA, you have the flexibility to truly enjoy country living with room for livestock, horses, RVs, trailers, ATVs, UTVs, and more. As you arrive, you are welcomed by a wide open parking area with plenty of space for all

  Kyle Footman ROGERS BARRY, REALTOR

  60 Bob White Trail, Monticello, FL 32344
• 

  

  /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 $196,824

  Last Listing Agent Karen Gillispie Keller Williams Town & Country

  265 W Seminole Ave, Monticello, FL 32344
• 

  

  /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
• 

  

  /43

  $375,000

  • 3 Beds
  • 3 Baths
  • 2,706 Sq Ft

  339 Silver Lake Rd, Monticello, FL 32344

  Large home on 5 acres mostly pasture~very peaceful setting~BRAND NEW LVP~Open concept with vaulted ceilings~large oaks~perfect pasture for horses or cattle~No HOA~

  Steve Walker Steve C. Walker Realty, LLC

  339 Silver Lake Rd, Monticello, FL 32344
• 

  

  /27

  $349,900

  Sold Jul 18, 2025

  149 Coopers Pond Rd, Monticello, FL 32344

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

  Last Sold Summary

  • $219/SF
  • 106 Days On Market

  Last Listing Agent Tiffany Kasdorf Kozloski Realty, LLC

  149 Coopers Pond Rd, Monticello, FL 32344
• 

  

  /42

  Est $719,378

  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
• 

  

  /4

  $299,000

  • Land
  • 85.69 Acres
  • $3,489 per Acre

  0 Big Joe Rd Unit 399642, Monticello, FL 32344

  85.69 acres of land located on Big Joe Road in Monticello. Zoned Agri-05, this versatile property offers a unique blend of privacy, natural beauty, and development potential. Featuring a mix of wetlands and usable upland areas, the property may be ideal for a variety of uses including recreational development, camping, hunting retreat, RV park, event venue, outdoor hospitality concepts, or future

  Lynnaye Boyd Resilience Realty

  0 Big Joe Rd Unit 399642, Monticello, FL 32344
• 

  

  /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 $502,104

  Last Listing Agent Jason Boone Keller Williams Town & Country

  885 S Waukeenah St, Monticello, FL 32344
• 

  

  /38

  Est $239,155

  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
• 

  

  /34

  $274,000

  Under Contract

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

  450 W Madison St, Monticello, FL 32344

  Nestled beneath a canopy of mature trees just minutes from downtown Monticello, 450 W. Madison Street is a charming home filled with character, warmth, and inviting indoor-outdoor living. Located in a golf cart-friendly community, this property offers the perfect blend of small-town charm, everyday convenience, and the relaxed pace that makes historic Monticello so special. From the brick walkway

  Michael Manuel CONSULTANTS TO HOMEBUI

  450 W Madison St, Monticello, FL 32344

Showing Results 161 - 200, Page 5 of 18