Monticello, FL Homes for Sale

• 

  

  

  /46

  $450,000

  • 3 Beds
  • 2 Baths
  • 2,239 Sq Ft

  254 Woodland Dr, Monticello, FL 32344

  Custom home on 4.29 private acres~split bedroom plan~separate dining room~rocking chair front porch~screened porch overlooking wooded backyard~fireplace~upstairs room could be office or playroom~huge 40x40 workshop~FIRST TIME ON THE MARKET

  Renee Smawley Steve C. Walker Realty, LLC

  254 Woodland Dr, Monticello, FL 32344
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  /38

  $609,900

  New Construction $10K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 2,134 Sq Ft

  261 Hiawatha Farms S, Monticello, FL 32344

  Back on the Market! Out of town buyers financing fell through. Welcome to this stunning new construction masterpiece, meticulously designed and built by the esteemed Kasdorf Design & Build, LLC. This craftsman beauty is awaiting its first owners and will be ready for occupancy by the beginning of May. Spanning an impressive 2134 square feet, this home offers a spacious and open concept floor

  Ross Kozloski Kozloski Realty, LLC

  261 Hiawatha Farms S, Monticello, FL 32344
• 

  

  

  /19

  $157,000

  • Land
  • 10.54 Acres
  • $14,896 per Acre

  XX Ridge Rd, Monticello, FL 32344

  Leave Urbana and breathe... 10.54 acres in Exclusive Casa Bianca Ridge. Beautiful, rare lot on which to build your dream home. There is room to create a multi-generational paradise or your own personal playground. Nicely wooded parcel with a gentle stream deeper into the property. Very private. Survey in associated docs. Move quickly. Gate at Driveway. Do not enter the property without approval.

  Nicholas Harrington Keller Williams Town & Country

  XX Ridge Rd, Monticello, FL 32344
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  /11

  $45,000

  • Land
  • 2.5 Acres
  • $18,000 per Acre

  1 W Meadow Rd, Monticello, FL 32344

  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
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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
• 

  

  /23

  $325,000

  • 5 Beds
  • 2 Baths
  • 2,659 Sq Ft

  2664 W Washington Hwy, Monticello, FL 32344

  FULLY RENOVATED SPACIOUS HOUSE, 1.3 acres, on picturesque US 90 near Monticello. This move-in-ready home in good condition is a 1950’s era brick ranch-style home with new plumbing, new electric, fresh paint, new roof, and a whole home generator. The main living area is 2,659 sf with a unique two levels. 5 bedrooms and 2 baths with plenty of character, including the "Captain's Room" with built-in

  Heather Boyd FL-GA Realty & Auction

  2664 W Washington Hwy, Monticello, FL 32344
• 

  

  /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
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  /30

  $185,000

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft

  28 Kameron Dr, Monticello, FL 32344

  Brand New Inside! 1-Acre Modern Retreat Just Minutes from the City. Enjoy the ultimate "new home" experience without the wait! This 2-bedroom, 1-bathroom gem at 28 Kameron Dr has been completely transformed with a brand new interior, offering high-end laminate flooring, fresh paint, and modern finishes throughout. Situated on a sprawling, level 1-acre lot, you’ll enjoy total privacy and room to

  Chip Williams Keller Williams Town & Country

  28 Kameron Dr, Monticello, FL 32344
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  /54

  $135,000

  $34K PRICE DROP

  • 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
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  /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
• 

  

  /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
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  /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
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  /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
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  /8

  $25,000

  $4K PRICE DROP

  • Land
  • 14,374 Sq Ft
  • $75,758 per Acre

  923 King St, Monticello, FL 32344

  Exceptional cleared corner lot with a concrete slab already in place—ready for your vision! City water and sewer connections are available, with electric at the road. Conveniently located just minutes from downtown Monticello. Motivated Sellers!

  Alicia Radtke All Realty Services

  923 King St, Monticello, FL 32344
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  /12

  $185,000

  • 3 Beds
  • 1 Bath
  • 1,312 Sq Ft

  670 Poplar St, Monticello, FL 32344

  Solid 3/1 SFR brick less than a mile from downtown Monticello! This quaint 1,312 sq ft home sits under a metal roof and only requires your vision and a little TLC to become a superb starter home or investment opportunity. It also includes an additional lot.

  Spencer Conner Keller Williams Town & Country

  670 Poplar St, Monticello, FL 32344
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  /6

  $20,999

  • 2 Beds
  • 2 Baths

  10 S Front Ct, Monticello, FL 32344

  TAKE ADVANTAGE OF OUR MEMORIAL DAY MEGA MOVE-IN EVENT! If you purchase this home, receive 2 months FREE site rent and NO application fees. Offer expires May 31, 2026. Act fast! Restrictions apply. A beautifully refurbished home is coming soon-and it's definitely one to keep an eye on. Renovations are currently underway with an estimated completion date of 5/31 (subject to change), bringing fresh

  Patty Davis Jefferson Pines

  10 S Front Ct, Monticello, FL 32344
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  /70

  $1,325,000

  • 5 Beds
  • 4.5 Baths
  • 5,476 Sq Ft

  221 Kiley Dr, Monticello, FL 32344

  Welcome to a rare North Florida estate just minutes from Tallahassee—where luxury, land, and lifestyle come together. 221 Kiley Road is situated on expansive acreage in Monticello, and this private retreat offers the perfect blend of seclusion and convenience, located just a short drive from the heart of Tallahassee. For buyers seeking space, privacy, and versatility without sacrificing proximity

  Wilda Sigler Keller Williams Town & Country

  221 Kiley Dr, Monticello, FL 32344
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  /4

  $550,000

  • 6,024 Sq Ft

  535 Hagan St, Monticello, FL 32344

  Rare Investor Opportunity: 7-Unit Residential Complex for Sale Don't miss this fantastic investment opportunity! This well-maintained 7-unit complex features: Six 3-bedroom, 1-bathroom units One 2-bedroom, 1-bathroom unit Walking distance to downtown – perfect for tenants seeking convenience Corner lot location with excellent visibility Designated parking spots for each unit 2023 Roof Whether

  Caleb Stephens Silo Hill Properties

  535 Hagan St, Monticello, FL 32344
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  /9

  $198,000

  • 3 Beds
  • 1 Bath
  • 1,366 Sq Ft

  870 Shady Ln, Monticello, FL 32344

  Welcome to 870 Shady Lane in Monticello, Florida—a charming property that offers the perfect blend of privacy, space, and small-town appeal. Nestled on a quiet, tree-lined street, this home provides a peaceful retreat while still being conveniently close to the historic downtown district, local shops, and dining. Surrounded by mature trees and natural beauty, the property offers a serene setting

  Angela Graham Hamilton Realty Advisors LLC

  870 Shady Ln, Monticello, FL 32344
• 

  

  /13

  $65,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  40 Westview Ln, Monticello, FL 32344

  Don't judge this home by its exterior!! The outside siding shows significant deterioration, which is fully reflected in the price. However, once inside, you'll find a livable interior that's far more functional than first impressions suggest. This double-wide is currently occupied and offers ;an opportunity for a buyer willing to look past the exterior and focus on the potential within. Not

  Alicia Radtke All Realty Services

  40 Westview Ln, Monticello, FL 32344
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  /52

  $425,000

  $24K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,188 Sq Ft

  930 E Pearl St, Monticello, FL 32344

  Built between 1890-1910, this Classic Revival home sits on 1.77 acres along one of Monticello’s most admired streets and offers timeless architecture with room to make it your own. The two-story layout includes 4 bedrooms and 3 bathrooms, with a circular driveway framed by boxwoods leading to a wide front porch perfect for rocking chairs. Inside, two front parlors flank the entry—one used as a

  Rachel Sparling All Realty Services

  930 E Pearl St, Monticello, FL 32344
• 

  

  /19

  $395,000

  $104K PRICE DROP

  • Land
  • 3.2 Acres
  • $123,438 per Acre

  XX Shiver Rd, Monticello, FL 32345

  Beautiful High lot at corner of Hwy 19, Shiver and Lake Rd. This listing is compilation of 3 contiguous parcels : (19-2N-5E-0140-0000-0300 and 19-2N-5E-0000-0210-0000 and 19-2N-5E-0140-0000-0170). for a total of 3.25 acres . PRIME location for multi-family, office, mixed use commercial business that needs visibility and ease of access. Utilities available- Water access to main line is Under Hwy

  Jennifer Ward Century 21 First Story

  XX Shiver Rd, Monticello, FL 32345
• 

  

  /26

  $79,900

  $4K PRICE DROP

  • Land
  • 6.4 Acres
  • $12,484 per Acre

  XXX Hopson Rd, Monticello, FL 32344

  Unique shaped parcel located in a serene rural area—perfect for building, recreation, or investment

  Shanna D'Attile Keller Williams Town & Country

  XXX Hopson Rd, Monticello, FL 32344
• 

  

  /70

  $410,000

  • 3 Beds
  • 2 Baths
  • 1,891 Sq Ft

  1637 N Jefferson Hwy, Monticello, FL 32344

  Awesome all brick 3 bedroom 2 bathroom home on 4 beautiful acres along North Jefferson Highway in Jefferson County, FL. Hardwood floors run throughout with tile in the kitchen and bathrooms. The kitchen offers solid wood cabinetry with soft-close drawers, updated appliances, and ample storage. Mature longleaf pines dot the property, which features a circular driveway and a 24x24 concrete pad with

  Catherine Hope All Realty Services

  1637 N Jefferson Hwy, Monticello, FL 32344
• 

  

  /18

  $174,900

  $100K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,553 Sq Ft

  34 W Hummingbird Ln, Monticello, FL 32344

  New beautiful LVP flooring on mother in law suite side of the property and wdo repair underneath the new flooring!! So many options with this property!! It boasts 2 separate living spaces joined by a common family room. One side of the home has 1 bed and 1 bath, it's own kitchen and living space. The other side of the home has 3 bedrooms, 2 bathrooms and the kitchen and living area. The family

  Susan Gillespie Lord & Stanley Realty, Inc.

  34 W Hummingbird Ln, Monticello, FL 32344
• 

  

  /11

  $105,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  40 Westview Ln, Monticello, FL 32344

  Being offered "AS IS" two separate 1 acre parcels combined 18-1N-4E-0108-000G-0030 & 18-1N-4E-0108-000G-0040 for a total of 2.01 acres. Don't judge this home by its exterior!! The outside siding shows significant deterioration, which is fully reflected in the price. However, once inside, you'll find a livable interior that's far more functional than first impressions suggest. This double-wide is

  Alicia Radtke All Realty Services

  40 Westview Ln, Monticello, FL 32344
• 

  

  /4

  $75,000

  $16K PRICE INCREASE

  • Land
  • 12,632 Sq Ft
  • $258,621 per Acre

  205 E Cherokee Ave, Monticello, FL 32344

  Prime vacant cleared commercial lot in downtown Monticello. Zoned Commercial B-2 Business Highway. Located Steps from US 19 South Across street from Burger King and Dollar Tree. Next door to Oreilly's Auto parts. High Traffic area and Good visibility. Address is for GPS only. Acreage is subject to survey.

  Starbuck Rissman Steve C. Walker Realty, LLC

  205 E Cherokee Ave, Monticello, FL 32344
• 

  /2

  $40,000

  • Land
  • 2.3 Acres
  • $17,391 per Acre

  0 Mallard Ln Unit 394437, Monticello, FL 32344

  Escape to peace & privacy, and with this beautiful 2.30-acre homesite located in the Lloyd Acres / Mallard Lane area of Jefferson County. Whether you’re planning your next home, a weekend retreat, or a smart land investment, this property offers the perfect blend of rural living with convenient access to Monticello and Tallahassee. Enjoy the natural surroundings, abundant trees, and quiet country

  Hunter Bowden Keller Williams Town & Country

  0 Mallard Ln Unit 394437, Monticello, FL 32344
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  /33

  $799,999

  • 3 Beds
  • 2.5 Baths
  • 3,677 Sq Ft

  728 Turney Anderson Rd, Monticello, FL 32344

  A Timeless Treasure, built by Riley Palmer Construction in 2006, this exceptional home captures the warmth and character of an early-1900s Craftsman farmhouse. It is located on 5 beautiful acres with mature pecan trees in the front and pines in the back yard. A spacious wrap around front porch welcomes you and features reclaimed New Orleans style doors and classic architectural details. Inside,

  Jared Parramore Coastwise Realty

  728 Turney Anderson Rd, Monticello, FL 32344

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