Monticello, FL Homes

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  /2

  $139,000

  • Land
  • 5 Acres
  • $27,800 per Acre

  TBD Orchard Ln, Monticello, FL 32344

  Great Location in Western Jefferson County offering country living with the convenience of Tallahassee only minutes away. Wooded 5 acres on private lane. Restricted for site built homes with minimum of 1200 sq ft heated and cooled. Adjoining 5 available for sale.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD Orchard Ln, Monticello, FL 32344
• Explore Monticello

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  /7

  $975 Per Month

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

  685 S Waukeenah St Unit B, Monticello, FL 32344

  RENTAL NEAR DOWNTOWN MONTICELLO. Cozy, energy-efficient, 1BR/1BA with extra storage, washer/dryer, covered parking, and a large side yard. Total renovation in 2025.Good neighbors and neighborhood. $975/month plus money-saving utility package that includes electricity, wifi, local TV, water, sewer, and garbage (no utility deposit needed). Month-to-month lease after the second month.

  Hines Boyd FL-GA Realty & Auction

  685 S Waukeenah St Unit B, Monticello, FL 32344
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  /5

  $67,500

  Sold Mar 13, 2026

  200 Samanthas Ln, Monticello, FL 32344

  • Land
  • 5 Acres
  • $13,500 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 23 Days On Market

  Current Estimated Value $143,000

  Last Listing Agent Allison Smith OaksFeather Realty

  200 Samanthas Ln, Monticello, FL 32344
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  Not Listed For Sale

  4014 Ashville Hwy, Monticello, FL 32344

  • 2 Beds
  • 2 Baths
  • 1,416 Sq Ft
  • Built 1993

  4014 Ashville Hwy, Monticello, FL 32344

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc
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  /41

  $499,000

  $51K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,268 Sq Ft

  398 Tecumseh Rd, Monticello, FL 32344

  Charming Cape Cod-style home tucked away on 5 acres just minutes to downtown Monticello. This one owner home has been lovingly maintained and reflects years of care and pride of ownership. With over 2200 square feet of living space, the home offers a comfortable layout. The main floor features three bedrooms, one bath, a welcoming living room with a gas fireplace, dining area, kitchen and a

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  398 Tecumseh Rd, Monticello, FL 32344
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  /2

  $1,855 Per Month

  • 3 Beds
  • 2 Baths
  • House for Rent

  345 Elliot Dr, Monticello, FL 32344

  Stunning new construction 3 bedroom, 2 bathroom, 2 car garage home in the quiet Pecan Hills subdivision in Monticello! This home features laminate floors throughout the entire home!! Granite counter tops in both the kitchen and bathrooms. The kitchen also features stainless steel appliances, as well as a pantry. The primary bedroom has a large walk in closet, as well as a good sized en suite with

  345 Elliot Dr, Monticello, FL 32344
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  /47

  $277,500

  Sold Apr 24, 2026

  575 W Madison St, Monticello, FL 32344

  • 3 Beds
  • 1.5 Baths
  • 1,834 Sq Ft
  • Built 1950

  Last Sold Summary

  • 6% Below List Price
  • $151/SF
  • 4 Days On Market

  Current Estimated Value $280,241

  Last Listing Agent Brooke Feld Keller Williams Town & Country

  575 W Madison St, Monticello, FL 32344
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  /39

  Est $1,374,685

  Not Listed For Sale

  25 Tallamont Rd, Monticello, FL 32344

  • 4 Beds
  • 3.5 Baths
  • 4,040 Sq Ft
  • Built 2003

  25 Tallamont Rd, Monticello, FL 32344

  Last Sold Summary

  • 111 Days On Market

  Last Listing Agent Caleb Stephens Silo Hill Properties
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  /5

  $199,000

  • Land
  • 5.03 Acres
  • $39,563 per Acre

  TBD W Washington, Monticello, FL 32344

  Fronting on Hwy-90 this high elevation lot is lightly wooded. Some restrictions apply.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD W Washington, Monticello, FL 32344
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  /12

  $1,195 Per Month

  • 2 Beds
  • 1.5 Baths
  • Condo for Rent

  530 Mississippi St Unit D, Monticello, FL 32344

  New Construction Upstairs unit is a 2 bed 1.5 bath apartment available in Monticello. Open floor plan, granite countertops, vinyl plank flooring, stainless steel appliances, washer and dryer in unit. Minutes to historic downtown, walking distance to the rec park, $60 flat fee for water monthly. There is a $75 application fee, all potential residents 18+ years of age must apply separately. Move

  530 Mississippi St Unit D, Monticello, FL 32344
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  /19

  $155,000

  Sold Jul 31, 2026

  XX Ridge Rd, Monticello, FL 32344

  • Land
  • 10.54 Acres
  • $14,706 per Acre

  Last Sold Summary

  • 1% Below List Price
  • 74 Days On Market

  Last Listing Agent Nicholas Harrington Keller Williams Town & Country

  XX Ridge Rd, Monticello, FL 32344
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  /42

  Est $95,000

  Not Listed For Sale

  3908 N Salt Rd, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1997

  3908 N Salt Rd, Monticello, FL 32344

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Catherine Hope All Realty Services
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  /36

  $584,000

  • 3 Beds
  • 3.5 Baths
  • 2,148 Sq Ft

  8250 Waukeenah Hwy, Monticello, FL 32344

  Enjoy two private year around spring fed ponds! Escape to your own private sanctuary on 30 breathtaking acres where nature, privacy, and craftsmanship come together. This custom-built retreat features soaring vaulted ceilings, expansive windows, & French doors- blurring the line between indoors and out, flooding every room with natural light and serene views. 2 Bed, 2.5 Bath, thoughtfully

  

  Bhishma Benedict

  FLORIDA HOMES REALTY & MORTGAGE GVILLE

  8250 Waukeenah Hwy, Monticello, FL 32344
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  /12

  $1,545 Per Month

  • 3 Beds
  • 2 Baths
  • House for Rent

  265 Bowman St, Monticello, FL 32344

  Move-In Special: Get 1/2 Off Your First Month’s Rent! Step into the charm of historic Monticello with this beautifully situated, tree-lined 3-bedroom, 2-bathroom home that’s been newly and completely remodeled in a modern style. Inside, enjoy bright, welcoming spaces with hardwood floors and a sleek kitchen featuring stainless steel appliances. Located on one of the town’s most established and

  265 Bowman 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 $329,849

  Last Listing Agent Ben Jones Southern Land & Homes

  1069 N Salt Rd, Monticello, FL 32344
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  Not Listed For Sale

  tbd Gamble Rd, Monticello, FL 32344

  tbd Gamble Rd, Monticello, FL 32344

  Last Sold Summary

  • 215 Days On Market

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc
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  /46

  $325,000

  • 4 Beds
  • 2 Baths
  • 2,304 Sq Ft

  947 Piney Woods Rd, Monticello, FL 32344

  Charming 2022 Mobile Home on 5 Peaceful Acres A rare blend of modern comfort and wide-open space, this 2022 mobile home sits on 5+ acres—perfect for anyone craving privacy, freedom, and room to grow. Whether you dream of a hobby farm, a quiet country retreat, or simply a place with no close neighbors, this property delivers. Embrace freedom of country living with the convenience of a modern home.

  

  Brian Bachman

  Kelly & Kelly Properties, Inc

  947 Piney Woods Rd, Monticello, FL 32344
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  /4

  $135,000

  Sold Mar 03, 2026

  276 E Blue Bird Rd, Monticello, FL 32344

  • Land
  • 5 Acres
  • $27,000 per Acre

  Last Sold Summary

  • 29 Days On Market

  Current Estimated Value $613,633

  Last Listing Agent S.W. Ellis Blue Bird Homes & Lands

  276 E Blue Bird Rd, Monticello, FL 32344
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  /32

  Est $421,882

  Not Listed For Sale

  39 Indian Hills Rd, Monticello, FL 32344

  • 4 Beds
  • 2 Baths
  • 1,803 Sq Ft
  • Built 1987

  39 Indian Hills Rd, Monticello, FL 32344

  Last Sold Summary

  • 90 Days On Market

  Last Listing Agent Steve Walker Steve C. Walker Realty, LLC
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  /16

  $495,000

  $54K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  640 Nautilus Dr, Monticello, FL 32344

  Secluded 56.37 Acres with Metal Building & Living Quarters -Western Jefferson County. This property offers privacy, versatility and room to build or expand. The land features a 2880 sq ft heavy-gauged metal building designed for both residential and workshop use. Second floor includes 1200 sf of living space currently unfinished featuring two bedrooms, kitchen and living area and one bath. A

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  640 Nautilus Dr, Monticello, FL 32344
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  /45

  $465,000

  Sold Apr 30, 2026

  47 Mire Ct, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,806 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Above List Price
  • $257/SF
  • 82 Days On Market

  Last Listing Agent Amber McKinney Hamilton Realty Advisors LLC

  47 Mire Ct, Monticello, FL 32344
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  /42

  Est $551,464

  Not Listed For Sale

  273 Legacy Way, Monticello, FL 32344

  • 3 Beds
  • 2 Baths
  • 1,868 Sq Ft
  • Built 2017

  273 Legacy Way, Monticello, FL 32344

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Amber Renaud The Nova Group Realty
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  /2

  $50,000

  • Land
  • 2.5 Acres
  • $20,000 per Acre

  TBD E Meadow Rd, Monticello, FL 32344

  Wooded lot, pines and hardwoods. Mobile homes are allowed. High elevation.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD E Meadow Rd, 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 $318,303

  Last Listing Agent Catherine Hope All Realty Services

  4131 N Jefferson Hwy, Monticello, FL 32344
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  /3

  Not Listed For Sale

  00 Fountain Dr, Monticello, FL 32344

  00 Fountain Dr, Monticello, FL 32344

  Last Sold Summary

  • 2,316 Days On Market

  Last Listing Agent Hines Boyd FL-GA Realty & Auction
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  /18

  $25,000

  • Land
  • 4 Acres
  • $6,250 per Acre

  TBD S Salt Rd, Monticello, FL 32344

  This beautiful old Florida habitat is great for wildlife observation, birding, native forest growth, riding four-wheelers, building nesting boxes for ducks and bats or a hammock and a place to get away for primitive camping. Costco in Tallahassee, Florida is 30.4 miles and Walmart Supercenter in Perry, Florida is 32.1 miles. Monticello, Florida is 9.3 miles for Ice Cream and boutiques, shops,

  

  Lynette Sirmon

  All Realty Services

  TBD S Salt Rd, Monticello, FL 32344
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  /43

  $460,000

  Sold May 22, 2026

  4235 N Jefferson St, Monticello, FL 32344

  • 4 Beds
  • 2 Baths
  • 1,864 Sq Ft
  • Built 2001

  Last Sold Summary

  • 6% Below List Price
  • $247/SF
  • 56 Days On Market

  Current Estimated Value $472,022

  Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

  4235 N Jefferson St, Monticello, FL 32344
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  Not Listed For Sale

  TBD Clark Rd Unit n/a, Monticello, FL 32344

  TBD Clark Rd Unit n/a, Monticello, FL 32344

  Last Sold Summary

  • 1,524 Days On Market

  Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc
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  $1,805,000

  • Land
  • 192 Acres
  • $9,401 per Acre

  Vacant N Salt Rd, Monticello, FL 32344

  192± acre organic cattle farm located in beautiful Jefferson County, Florida Certified organic operation for 20+ years with a long-standing history of sustainable land stewardship Fully fenced and cross-fenced for efficient cattle rotation and livestock management Improved pastureland ideal for cattle, horses, or continued agricultural use Several picturesque homesites overlooking the scenic

  

  Ben Jones

  MOSSY OAK PROPERTIES

  Vacant N Salt Rd, 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 $371,070

  Last Listing Agent Allison Smith OaksFeather Realty

  4715 N Jefferson St, Monticello, FL 32344
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  /70

  Not Listed For Sale

  1291 Hayfield Spur, Monticello, FL 32344

  • 2 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • Built 2009

  1291 Hayfield Spur, Monticello, FL 32344

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Jason Naumann The Naumann Group Real Estate
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  /7

  $135,000

  • Land
  • 10 Acres
  • $13,500 per Acre

  576 Cox Rd, Monticello, FL 32344

  Looking for privacy, this 10 acres provides an ideal homesite with some clearing for your homesite completed. The balance of the land is woorded with a mix of hardwoords and pines. Some of the land is in welands/flood which provides a nice buffer for privacy and a wildlife habitat. There is a well/pump (no tank), an older septic, and power pole. 15 ft easement leads to the property. Located just

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  576 Cox Rd, Monticello, FL 32344
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  /3

  $258,900

  Sold Jul 09, 2026

  660 N Cherry St, Monticello, FL 32344

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 2026

  Last Sold Summary

  • $237/SF
  • 18 Days On Market

  Last Listing Agent Steve Walker Steve C. Walker Realty, LLC

  660 N Cherry St, Monticello, FL 32344
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  /38

  Est $291,259

  Not Listed For Sale

  Unlisted Address

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 2002

  Unlisted Address

  Last Sold Summary

  • 58 Days On Market

  Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc
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  /55

  $919,000

  • 3 Beds
  • 2.5 Baths
  • 2,436 Sq Ft

  9901 Gamble Rd, Monticello, FL 32344

  PRIVATE 41-ACRE ESTATE MINUTES FROM TALLAHASSEE - TRAILS, WILDLIFE, PASTURE & CUSTOM HOME Nestled among majestic oaks and rolling countryside, this exceptional estate offers a rare combination of privacy, natural beauty and comfortable country living. Beyond the gated entrance lies a beautiful setting of open land, mature trees, and abundant wildlife, offering endless possibilities for equestrian

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  9901 Gamble Rd, Monticello, FL 32344
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  /28

  $375,000

  Sold Jul 30, 2026

  1205 E Pearl St, Monticello, FL 32344

  • 3 Beds
  • 2.5 Baths
  • 2,373 Sq Ft
  • Built 1956

  Last Sold Summary

  • 11% Below List Price
  • $158/SF
  • 143 Days On Market

  Current Estimated Value $333,910

  Last Listing Agent Brian Bachman Kelly & Kelly Properties, Inc

  1205 E Pearl St, Monticello, FL 32344
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  /20

  Not Listed For Sale

  Lot 4 Watermill Rd, Monticello, FL 32344

  Lot 4 Watermill Rd, Monticello, FL 32344

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Sarah McKinzie Hum Real Estate
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  $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
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  /19

  $135,000

  Sold Feb 16, 2026

  XX Foggy Ln, Monticello, FL 32344

  • Land
  • 5.25 Acres
  • $25,714 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Cole Davis The Naumann Group Real Estate

  XX Foggy Ln, Monticello, FL 32344
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  /20

  Not Listed For Sale

  Lot 3 Watermill Rd, Monticello, FL 32344

  Lot 3 Watermill Rd, Monticello, FL 32344

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Sarah McKinzie Hum Real Estate

Showing Results 1 - 40, Page 1 of 18