Monticello, FL Homes

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  /54

  $149,000 Under Contract

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

  12447 Gamble Rd, Monticello, FL 32344

  Corner Lot! This 2 bedroom (could be a 3rd Bdrm 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 ideal spot for a hunting or fishing lodge or "Air B & B type of rental" specializing in

  

  Lynette Sirmon

  All Realty Services

  (448) 233-2927

  12447 Gamble Rd, Monticello, FL 32344
• Explore Monticello

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  /26

  $2,675 per month

  • 4 Beds
  • 2.5 Baths
  • 1,887 Sq Ft
  • House for Rent

  362 Creekside Ct, Monticello, FL 32344

  Newer 4 Bedroom, 2 1/2 Bath split plan with open floorplan in Monticello, Florida. Herringbone brick paver front porch and covered back porch is ready for you. Custom woodwork throughout, granite countertops, hand scraped wood floors, bar area with wine fridge, tray ceilings and more. Master bedroom has walk-in tiled shower, freestanding soaker tub and double vanities. Washer/Dryer included.

  

  Bonnie Scott-Walls

  Coldwell Banker Hartung

  (448) 900-4708

  362 Creekside Ct, Monticello, FL 32344
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  /17

  $40,000 Sold Feb 28, 2025

  487 Cox Rd, Monticello, FL 32344

  • Land
  • 2.5 Acres
  • $16,000 per Acre

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Liz Kuntz Keller Williams Town & Country

  487 Cox Rd, Monticello, FL 32344
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  /23

  Not Listed For Sale

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

  36 Mossy Oak Ln, Monticello, FL 32344

  36 Mossy Oak Ln, Monticello, FL 32344
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  /44

  $595,000

  • 3 Beds
  • 2.5 Baths
  • 3,054 Sq Ft

  79 Lakeside Rd, Monticello, FL 32344

  Go Back in time in this traditional farmhouse nestled on 4.44 acres totally fence and cross fenced. Over 1110 sq ft of screened porch for entertaing, relaxing, or looking at the 20x30 Koi pond. Sparkling wood foors throughout create warmth to the spacious rooms. 9x32 central hallway, large living room, family room, and all bedrooms are oversized. 600 sq ft garage with loft and attached 1 car

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 230-7686

  79 Lakeside Rd, Monticello, FL 32344
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  /11

  $2,000 per month

  • 3 Beds
  • 1 Bath
  • 1,263 Sq Ft
  • House for Rent

  1405 S Jefferson St, Monticello, FL 32344

  Totally remodeled throughout, home or business. No pets, non smokers. Spacious full kitchen with updated finishes. 3 comfortable bedrooms. 1263 sq ft with flexible living or work space. Screen porch with utlility room for washed/dryer. Immediate occupancy.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 230-7739

  1405 S Jefferson St, Monticello, FL 32344
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  /50

  $300,000 Sold Aug 13, 2025

  1069 N Salt Rd, Monticello, FL 32344

  • Land
  • 44.35 Acres
  • $6,764 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 28 Days On Market

  Current Estimated Value $305,349

  Last Listing Agent Ben Jones Southern Land & Homes

  1069 N Salt Rd, Monticello, FL 32344
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  /21

  Not Listed For Sale

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

  750 N Cherry St, Monticello, FL 32344

  750 N Cherry St, Monticello, FL 32344
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  /45

  $599,900

  • 3 Beds
  • 2.5 Baths
  • 2,546 Sq Ft

  181 Heritage Blvd, Monticello, FL 32344

  Certified Florida Green Home on 3 acres in the highly sough after Heritage Hills s/d. Enjoy the perfect blend of privacy and convenience with this Craftsman-style home, offering an easy commute to both Tallahassee and Monticello. The like-new residence boasts high-end finishes throughout, including crown molding, coffered ceilings, wainscoting, and a cozy gas fireplace. Relax or entertain

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 678-3070

  181 Heritage Blvd, Monticello, FL 32344
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  /17

  $1,299 - $1,306 per month

  Jefferson Pines

  3 Beds

  24 Parkway Pines, Monticello, FL 32344

  Welcome to Jefferson Pines! An all-age, pet-friendly manufactured home community located in Monticello, FL. Here, you'll find the ideal mix of small-town charm and everyday convenience, with a community feel that's perfect for individuals and families alike.Nestled in a quiet area just minutes from local shopping and dining, Jefferson Pines offers the comfort of community living with easy

  24 Parkway Pines, Monticello, FL 32344
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  /10

  $80,000 Sold May 05, 2025

  895 Independent St, Monticello, FL 32344

  • 2 Beds
  • 1 Bath
  • 782 Sq Ft
  • Built 1955

  Last Sold Summary

  • 18% Below List Price
  • $102/SF
  • 27 Days On Market

  Current Estimated Value $81,298

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc

  895 Independent St, Monticello, FL 32344
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  /42

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,057 Sq Ft

  1851 Whitehouse Rd, Monticello, FL 32344

  1851 Whitehouse Rd, Monticello, FL 32344
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  /43

  $295,000 Under Contract

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

  425 N Mulberry St, Monticello, FL 32344

  Charming 1920's Two-Story Home in the Heart of Downtown Monticello, Fl. Step back in time with this beautiful home nestled on a spacious 1/2 acre lot in the heart of Monticello. Bursting with character and potential, this property is perfect for those looking to restore a classic Southern gem. Inside, you will find original, wood ceiling, floors , and walls that are just waiting to be brought

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 222-3718

  425 N Mulberry St, Monticello, FL 32344
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  /6

  $800 per month

  • 4 Beds
  • 2 Baths
  • 1,412 Sq Ft
  • House for Rent

  660 Poplar St, Monticello, FL 32344

  Rent with confidence from a licensed Real Estate Brokerage. We have a quick and simple application process. Contact us through this website or call to set up a tour and apply today! WE PROUDLY WELCOME ALL PETS. Welcome to this charming 4-bed, 2-bath home! Our spacious layout is perfect for comfortable living. Enjoy the yard to unwind after a long day, enjoy the fresh air, and gather for

  Erich Spivey ALABAMA LLC

  660 Poplar St, Monticello, FL 32344
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  /41

  $310,000 Sold Sep 04, 2025

  4131 N Jefferson Hwy, Monticello, FL 32344

  • 5 Beds
  • 4 Baths
  • 3,330 Sq Ft
  • Built 1979

  Last Sold Summary

  • 27% Below List Price
  • $93/SF
  • 164 Days On Market

  Current Estimated Value $322,368

  Last Listing Agent Catherine Hope All Realty Services

  4131 N Jefferson Hwy, Monticello, FL 32344
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  /31

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,112 Sq Ft

  112 Rudolph Ln, Monticello, FL 32344

  112 Rudolph Ln, Monticello, FL 32344
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  /37

  $365,000

  • 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) 236-0470

  205 N Rhodes St, Monticello, FL 32344
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  /2

  $975 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • House for Rent

  685 S Waukeenah St Unit B, Monticello, FL 32344

  NEW UNIT FOR RENT IN MONTICELLO. Cozy, energy efficient, 1 BR/1Bath with extra storage, washer/dryer, covered parking, large backyard. Total renovation in 2025; everything new. Easy walk to shopping and downtown. Good neighbors and neighborhood. $975/month plus money-saving utility package that includes electricity, wifi, local TV, water, sewer, and trash (no utility deposit needed).

  Hines Boyd FL-GA Realty & Auction

  685 S Waukeenah St Unit B, Monticello, FL 32344
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  /25

  $307,000 Sold Jun 06, 2025

  203 Pine Cone Dr, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 2021

  Last Sold Summary

  • 3% Below List Price
  • $194/SF
  • 51 Days On Market

  Current Estimated Value $319,603

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc

  203 Pine Cone Dr, Monticello, FL 32344
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  /36

  Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,344 Sq Ft

  87 Old Tung Grove Rd, Monticello, FL 32344

  87 Old Tung Grove Rd, Monticello, FL 32344
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  /6

  $230,000 Under Contract

  • Land
  • 10 Acres
  • $23,000 per Acre

  TBD Orchard Ln, Monticello, FL 32344

  The great escape- A very special 10 acres, all high and dry, convenient to Tallahassee, easy 12 to 15 minute drive. Site built homes only. It was pasture land that has volunteer pines and hardwoods growing Easy to turn back into pasture for horses of left like ot is for privacy.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 217-5194

  TBD Orchard Ln, Monticello, FL 32344
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  /39

  $343,000 Sold Aug 26, 2025

  4715 N Jefferson St, Monticello, FL 32344

  • 3 Beds
  • 3 Baths
  • 2,063 Sq Ft
  • Built 1979

  Last Sold Summary

  • 10% Below List Price
  • $166/SF
  • 18 Days On Market

  Current Estimated Value $345,388

  Last Listing Agent Allison Smith OaksFeather Realty

  4715 N Jefferson St, Monticello, FL 32344
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  /42

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,432 Sq Ft

  995 Taylor Rd, Monticello, FL 32344

  995 Taylor Rd, Monticello, FL 32344
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  /28

  $120,000

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  159 W Notre Dame St, Monticello, FL 32344

  A perfect redevelopment opportunity or your next home or investment property awaits! Lot could be subdivided into two lots. Enjoy peaceful country living just minutes from I-10 with this well-maintained 2-bedroom, 1-bath mobile home on a half acre in beautiful Lloyd, Florida. The home features about 600 square feet of cozy, efficient living space that’s been lovingly cared for and is move-in

  

  Raymond Seaman

  Dalton Wade, Inc

  (448) 200-2241

  159 W Notre Dame St, Monticello, FL 32344
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  /2

  $550,000 Sold Jun 28, 2025

  28 Sanctuary Dr, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft
  • Built 2024

  Last Sold Summary

  • $297/SF
  • 17 Days On Market

  Last Listing Agent Chance Shutes Keller Williams Town & Country

  28 Sanctuary Dr, Monticello, FL 32344
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  /27

  Not Listed For Sale

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

  136 Sutton, Monticello, FL 32344

  136 Sutton, Monticello, FL 32344
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  /38

  $274,900

  • 2 Beds
  • 2 Baths
  • 1,411 Sq Ft

  490 N Cherry Ct, Monticello, FL 32344

  Step into city living just steps from Downtown Monticello, Fl. This one-story condo with private backyard blends modern convenience in this coveted over 55 neighborhood of only 8 units. 2 bedrooms & 2 baths, laundry room with stack unit, W/D included, but the favorite room in the house is the sunroom. Inside, enjoy the bright open-concept living with high ceilings, crown molding, LVP & engineered

  

  Pam Hoveland

  Landcorp, Inc.

  (448) 231-4689

  490 N Cherry Ct, Monticello, FL 32344
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  /42

  $510,000 Sold Jun 30, 2025

  1094 Paul Thompson Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,898 Sq Ft
  • Built 2008

  Last Sold Summary

  • 2% Below List Price
  • $269/SF
  • 18 Days On Market

  Current Estimated Value $528,389

  Last Listing Agent Amber Renaud The Nova Group Realty

  1094 Paul Thompson Rd, Monticello, FL 32344
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  /27

  Not Listed For Sale

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

  330 Pine Cone Dr, Monticello, FL 32344

  330 Pine Cone Dr, Monticello, FL 32344
• 

  

  /21

  $172,500

  • Land
  • 10 Acres
  • $17,250 per Acre

  TBD Rainey Run, Monticello, FL 32344

  Gated rural community, lakefront 10 acres with large hardwoods. Tranquility awaits, gently sloping land with some clearing.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 233-5231

  TBD Rainey Run, Monticello, FL 32344
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  /3

  $72,000 Sold Mar 31, 2025

  4019 Ashville Hwy Unit o, Monticello, FL 32344

  • Land
  • 38.07 Acres
  • $1,891 per Acre

  Last Sold Summary

  • 78% Below List Price
  • 62 Days On Market

  Last Listing Agent Sarah Scott Coldwell Banker Hartung

  4019 Ashville Hwy Unit o, Monticello, FL 32344
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  /41

  Est $756,719 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,085 Sq Ft

  424 S Hiawatha Farms Rd, Monticello, FL 32344

  424 S Hiawatha Farms Rd, Monticello, FL 32344
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  /57

  $579,000

  • 3 Beds
  • 3 Baths
  • 2,187 Sq Ft

  515 E Palmer Mill Rd, Monticello, FL 32344

  Remarkable, peaceful in-town oasis on 3.54 acres! An incredible find in the heart of downtown Monticello, FL. Not only is this home located on a private 3.54 acre spread, surrounded by a perimeter of natural foliage, but the home itself has been beautifully updated, blending the charm of old and the convenience of new. The 3 bedroom/3 bathroom, 2,000+ sq ft home has a kitchen flooded with natural

  

  Brenna Kelly-Ward

  Kelly & Kelly Properties, Inc

  (448) 334-5445

  515 E Palmer Mill Rd, Monticello, FL 32344
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  /5

  $146,000 Sold Aug 01, 2025

  TBD Taylor Rd, Monticello, FL 32344

  • Land
  • 6.07 Acres
  • $24,053 per Acre

  Last Sold Summary

  • 268 Days On Market

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc

  TBD Taylor Rd, Monticello, FL 32344
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  /42

  Est $940,377 Not Listed For Sale

  • 6 Beds
  • 5.5 Baths
  • 7,011 Sq Ft

  106 Big Rye Rd, Monticello, FL 32344

  106 Big Rye Rd, Monticello, FL 32344
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  /54

  $700,000

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

  925 Hiawatha Farms Rd, Monticello, FL 32344

  Custom hurricane-resistant/efficiency home on 3.6 private acres in a gated equestrian community, just 17 miles east of Tallahassee and 1 mile to I-10 (Exit 217). Built in 2013, this 2,112 sq ft home features 4 bedrooms, 3 full baths, and 9’ ceilings throughout. Constructed with Nudura ICF 12” insulated concrete exterior walls for superior strength, energy efficiency, and sound insulation.

  

  Joann Jacobs

  Coldwell Banker Hartung

  (448) 230-7519

  925 Hiawatha Farms Rd, Monticello, FL 32344
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  /13

  $34,000 Sold Mar 31, 2025

  265 Bowman St, Monticello, FL 32344

  • 1 Bed
  • 1 Bath
  • 660 Sq Ft
  • Built 1911

  Last Sold Summary

  • 15% Below List Price
  • $52/SF
  • 27 Days On Market

  Current Estimated Value $43,281

  Last Listing Agent Amber Renaud The Nova Group Realty

  265 Bowman St, Monticello, FL 32344
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  /39

  Est $1,268,798 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,040 Sq Ft

  25 Tallamont Rd, Monticello, FL 32344

  25 Tallamont Rd, Monticello, FL 32344
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  /42

  $198,000 Under Contract

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

  2436 N Jefferson Hwy, Monticello, FL 32344

  THIS PROPERTY WILL NEED A TOTAL RENOVATION ON BOTH HOMES. Discover the perfect blend of rustic charm and opportunity with this unique country property. Nestled on 3+ acres, this older farm house offers character and room to grow. The main home features spacious living areas with wood floors throughout and plenty of potential for updates to make it your own. Front screen porch and large utility

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (850) 604-1107

  2436 N Jefferson Hwy, Monticello, FL 32344
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  /37

  $160,000 Sold Mar 19, 2025

  183 Chittling Rd, Monticello, FL 32344

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

  Last Sold Summary

  • 9% Below List Price
  • $106/SF
  • 41 Days On Market

  Last Listing Agent Catherine Hope All Realty Services

  183 Chittling Rd, Monticello, FL 32344

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