Homes for Sale in 32344

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  /52

  $449,000

  • 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
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  /7

  $135,000

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

  576 Cox Rd, Monticello, FL 32344

  Discover a fantastic future homesite on a secluded 10-acre parcel in northern Jefferson County, Florida! Accessed via a 15-foot-wide easement off a private road, the property opens up to a beautiful, private clearing ideal for building your dream home. The land features a mix of large pines, hardwoods, and magnolias, creating a serene, natural setting. Key utilities are already in place or

  Gabriela Sacco All Realty Services

  576 Cox Rd, Monticello, FL 32344
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  /4

  $60,000

  • Land
  • 0.43 Acre
  • $139,535 per Acre

  tbd Jackson St, Monticello, FL 32344

  2 building lots in the heart of Monticello, quiet side street. Each lot is 50 ft wide by approx. 190 deep. The lots back up to Waukeenah Street.

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 334-6781

  tbd Jackson St, Monticello, FL 32344
• 

  

  

  /17

  $252,000

  • 3 Beds
  • 1 Bath
  • 1,334 Sq Ft

  1160 E Washington St, Monticello, FL 32344

  Remodeled brick home, 3 br 1 bath, open kitchen living room with fireplace. Large utility room with bonus room. Convenient Monticello location. Carport and privacy fenced back yard.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 231-4719

  1160 E Washington St, Monticello, FL 32344
• 

  

  

  /55

  $165,000

  • 2 Beds
  • 2 Baths
  • 1,096 Sq Ft

  1515 Tennessee Ave, Monticello, FL 32344

  Brimming with rustic charm, this 2 bedroom, 2 bathroom home sits on .29 acres just outside Monticello, FL giving you the peace of county living with lower taxes and the convenience of a quick drive into town. Inside, the 1,096sqft layout features inviting wood paneling throughout, with updates to the guest bathroom, a full electrical rewire and new water line and cozy spaces filled with

  Catherine Hope All Realty Services

  1515 Tennessee Ave, Monticello, FL 32344
• 

  

  /11

  $90,000

  • Land
  • 3 Acres
  • $30,000 per Acre

  1309 Cook Rd, Lamont, FL 32336

  Looking for a peaceful retreat or a smart investment opportunity? This 3 acre lot in Monticello, Florida, might be just what you need! The property comes with a mobile home (which can be renovated or replaced according to your vision), well, septic, electric already in place! Beautiful mature oak trees, pines, and more! There is already an established deer food plot with an abundance of fresh

  Alicia Radtke All Realty Services

  1309 Cook Rd, Lamont, FL 32336
• 

  

  /31

  $277,000

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft

  104 Pine Cone Dr, Monticello, FL 32344

  This gorgeous, 3-bedroom, 2-bath modular home, recently renovated by Paul Davis, combines modern comfort and style. Inside, you’ll find an open floor plan, a brand-new kitchen with granite countertops, new appliances, and updated finishes that make everyday living and entertaining a joy. The primary bedroom offers a luxurious ensuite with double vanities, a walk-in shower, and garden tub, as well

  Trevor Ann Clark Keller Williams Town & Country

  104 Pine Cone Dr, Monticello, FL 32344
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  /61

  $34,500

  • Land
  • 3 Acres
  • $11,500 per Acre

  Vacant N Forest Ct, Monticello, FL 32344

  OWNER FINANCING MAY BE A POSSIBILITY. Check out this amazing 3+/- acre lot in the Aucilla Forest & Meadows Subdivision in beautiful Jefferson County, FL! This spacious lot would be the perfect place to build your dream home, or place your new manufactured/mobile home! Site built, or manufactured homes must be a minimum of 720 heated square feet. The land is currently wooded with some beautiful

  Jerrod Trainer Jerrod A Trainer & Associates

  Vacant N Forest Ct, Monticello, FL 32344
• 

  

  /42

  $725,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,365 Sq Ft

  81 Old Tung Grove Rd, Monticello, FL 32344

  New Construction move in ready. Sacious over 2300 sq fr. with upstairs bonus room with bath and closet, could be 4th bedroom. 5.38 acre lot. Top of the lines finishes. Convenient to Tallahassee 15 minute drive.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 334-6582

  81 Old Tung Grove Rd, Monticello, FL 32344
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  /9

  $120,000

  • Land
  • 2.01 Acres
  • $59,701 per Acre

  40 Westview Ln, Monticello, FL 32344

  Load up and take a ride to Lloyd Fl. located between Tallahassee and Monticello Fl. Being offered "AS IS" two 1 acre parcels 18-1N-4E-0108-000G-0030 & 18-1N-4E-0108-000G-0040 for a total of 2.01 acres! Power, septic and well on site, as well as access to city water. There is a 1989 mobile home on site that may be salvageable to the right buyer, or haul it off and prepare for a new build! Bring

  Alicia Radtke All Realty Services

  40 Westview Ln, Monticello, FL 32344
• 

  

  /8

  $450,000

  • Land
  • 85.26 Acres
  • $5,278 per Acre

  0 Big Joe Rd Unit 2025007616, 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.

  Florie Gage Cornerstone Coastal Properties

  0 Big Joe Rd Unit 2025007616, Monticello, FL 32344
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  /12

  $165,000

  • Land
  • 10.47 Acres
  • $15,759 per Acre

  5936 Vista Rd, Monticello, FL 32344

  Perfect opportunity to own 10+ acres to build your dream home on this blank slate. Lot is mostly flat and backs up to a power line so no building behind the property. Abundant wildlife present (deer and turkey) and bring all your yard animals. Ride up Vista Road to see your neighbors on larger lots to Waukeenah Hwy to visit the beautiful Monticello Vineyards and Winery. Lot dimensions are

  

  Jaquelynn Harrison-Cofty

  Property Finders Nguyen Realty

  (448) 334-6928

  5936 Vista Rd, Monticello, FL 32344
• 

  

  /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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  /67

  $995,000

  • 4 Beds
  • 4.5 Baths
  • 3,696 Sq Ft

  825 Rainey Run, Monticello, FL 32344

  Set on 10 private acres, this exceptional estate offers a lifestyle defined by space, serenity, and effortless luxury. Surrounded by nature and bordered by a tranquil private creek, the property feels like a personal retreat—yet remains perfectly designed for modern living and entertaining. Inside, 3,696 square feet of light-filled living space unfolds with soaring ceilings, expansive windows,

  Renee Dawkins Dawkins Realty LLC

  825 Rainey Run, Monticello, FL 32344
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  /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) 305-5882

  64 Sanctuary Dr, Monticello, FL 32344
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  /38

  $375,000

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

  339 Silver Lake Rd, Monticello, FL 32344

  Gorgeous home on 5 acres mostly pasture. Open concept with vaulted ceilings; great entertainment/family home. Private setting; must see to believe.Copyright © 2026 Tallahassee Board of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

  Steve Walker Steve C. Walker Realty, LLC

  339 Silver Lake Rd, Monticello, FL 32344
• 

  

  /19

  $299,000

  • 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
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  /11

  $22,500

  • Land
  • 2 Acres
  • $11,250 per Acre

  0 Flatwoods, Monticello, FL 32344

  Land for Sale – Flatwoods, FL 32344. Size: 2.0 Acres. Location: Flatwoods Road, Monticello, Florida 32344. Property Highlights: Buildable lot with plenty of space; Power available on the road; 411.75 feet of road frontage; Peaceful rural setting surrounded by large parcels; No HOA – flexible use for site-built or modular homes. About 40 minutes to Tallahassee. Ideal for a private

  Andrey Rossin CASH FLOW IN MIAMI REALTY

  0 Flatwoods, Monticello, FL 32344
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  /61

  $589,900

  • 4 Beds
  • 3 Baths
  • 2,660 Sq Ft

  513 Creekside Ct, Monticello, FL 32344

  Custom home built by Kessler Construction on 2 full acres in desirable Crook Creek subdivision~4 bedrooms/3 full baths~gourmet kitchen~split bedroom plan~luxury master bath~incredibly high ceilings~42x14 screened porch~oversized 2-car garage~located on a cul-de-sac, this home offers peaceful privacy

  Renee Smawley Steve C. Walker Realty, LLC

  513 Creekside Ct, Monticello, FL 32344
• 

  

  /42

  $198,000

  • 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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  /16

  $487,878

  • Land
  • 122 Acres
  • $3,999 per Acre

  0 James Noble Rd, Greenville, FL 32331

  Millwood Timberland East is a balanced property located in a great recreational market. The Ashville area is home to numerous trophy grade recreational properties and is known for exceptional whitetail, turkey and waterfowl hunting. This property features an efficient footprint with good access and internal road infrastructure. The uplands are planted with slash pine that are approximately 8

  Bryant Peace Saunders Real Estate

  0 James Noble Rd, Greenville, FL 32331
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  /18

  $1,100,000

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

  0 Gum Swamp, Greenville, FL 32331

  Millwood Timberland West is a balanced recreational asset located in the Ashville, FL region. The internal road system meanders through the ecologically diverse landscape of pine plantations, live oaks and forested wetlands. The uplands are planted in slash pine that are approximately 15 years old with pockets of oak hammock and natural ponds. The ecosystem provides exceptional habitat for

  Bryant Peace Saunders Real Estate

  0 Gum Swamp, Greenville, FL 32331
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  /3

  $437,500

  • Land
  • 22.13 Acres
  • $19,770 per Acre

  00 Boston Hwy, Monticello, FL 32344

  2 MILES FROM Monticello Courthouse! Bordering Jefferson County Country Club. 2 Parcels for total of 22.13 Acres adjacent to Jefferson County Golf Club and bordering Boston Hwy- 1028 ft. frontage - and Mamie Scott Drive. 2 Acres on Mamie Scott with 360' FRONTAGE AND has City Water/Electric Access and is actually within City Limits with zoning of RESIDENTIAL-MULTIFAMILY. Remaining property zoning

  Jennifer Ward Century 21 First Story

  00 Boston Hwy, Monticello, FL 32344
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  /3

  $117,036

  • Land
  • 11.23 Acres
  • $10,422 per Acre

  Lot 29, Block A E Meadow Rd, Monticello, FL 32344

  11.23 +/- acres at very end of East Meadow Road adjacent to 300+ acres owned by the Suwannee River Water Management District and nearby Aucilla River. Currently being used recreationally as a small hunting retreat by current owner. Additional connecting 9.4 +/- acres also available for purchase from same owner. Why not purchase both parcels and have 20 +/- acres all to yourself. These

  Justin Peel Maclay Realty & Management LLC

  Lot 29, Block A E Meadow Rd, Monticello, FL 32344
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  /3

  $97,964

  • Land
  • 9.4 Acres
  • $10,422 per Acre

  Lot 30, Block A E Meadow Rd, Monticello, FL 32344

  9.4 +/- acres at very end of East Meadow Road and nearby Aucilla River. Currently being used recreationally as a small hunting retreat by current owner. Additional connecting 11.23 +/- acres also available for purchase from same owner. Why not purchase both parcels and have 20 +/- acres all to yourself. These opportunities don’t come along very often so don’t miss out.

  Justin Peel Maclay Realty & Management LLC

  Lot 30, Block A E Meadow Rd, 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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  /4

  $130,000

  • Land
  • 9.96 Acres
  • $13,052 per Acre

  00 Mallard Blue Jay Ln Unit 2/3, Monticello, FL 32344

  The listing contains (2) adjacent raw land parcels in the Lloyd Acres Subdivision = 9.96 acres total. See parcel IDs: 18-1N-4E-0113-000C-0010 (6.41 acres; Mallard Lane) + 18-1N-4E-0112-000C-0050 (3.55 acres; Bluejay Rd). Look for real estate signs (2) to help identify the acreage for sale. The property is zoned Residential-01 (1 home/1 acre), making it a great opportunity for someone wanting to

  

  Brenna Kelly-Ward

  Kelly & Kelly Properties, Inc

  (448) 230-8821

  00 Mallard Blue Jay Ln Unit 2/3, Monticello, FL 32344
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  /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
• 

  

  /6

  $475,000

  • Land
  • 85.69 Acres
  • $5,543 per Acre

  xxx Big Joe Rd, Monticello, FL 32344

  This 86 acre beautiful and serene parcel is Zoned Agri-05 and has tons of potential and a plethora of land uses ranging from residential, to outdoor recreational, and even institutional. Perfect for a wedding venue, camping grounds, or possibly a gun range. Seller is willing to pay for survey with an acceptable offer!

  Lynnaye Boyd Resilience Realty

  xxx Big Joe Rd, Monticello, FL 32344
• 

  

  /18

  $179,900

  • 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
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  /32

  $525,000

  • 3 Beds
  • 3 Baths
  • 3,026 Sq Ft

  3827 N Jefferson St, Monticello, FL 32344

  Spacious Contemporary Home on 5 Acres with Pond, Minutes from Thomasville, Ga! Enjoy peaceful country living with modern comforts in this stunning 3 bedroom, 3 bathroom brick home on 5 beautiful acres with a private pond. With over 3,000 square feet of living space, this property offers room to spread out and features thoughtful touches throughout. Inside, you'll find a large den with cozy

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (850) 367-9518

  3827 N Jefferson St, Monticello, FL 32344
• 

  

  /19

  $395,000

  • 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

Showing Results 41 - 72, Page 2 of 2