Jefferson County FL Homes for Sale

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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
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  /3

  $258,900

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

  660 N Cherry St, Monticello, FL 32344

  New construction in the heart of Monticello's Historic District! This beautifully built 1,092 sq ft off-grade home offers modern finishes while fitting seamlessly into the character of the neighborhood. The open floor plan features luxury vinyl plank flooring throughout, a stylish kitchen and stainless steel appliances, and quality craftsmanship from top to bottom. Bathrooms are finished with

  Steve Walker Steve C. Walker Realty, LLC

  660 N Cherry St, Monticello, FL 32344
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  /57

  $599,000

  • 7 Beds
  • 7 Baths
  • 5,139 Sq Ft

  625 E Washington St, Monticello, FL 32344

  Introducing a stunning 1.2 acre estate in the heart of Historic Downtown Monticello. The Simon-Ridgeway home was built in 1888 and boasts a generous 4,500 sq ft of living space and features 7 spacious bedrooms, 5 of which come with its own en-suite bathroom for ultimate privacy and convenience. City granted BNB status - making this perfect for an owner/occupier wanting to work from home and enjoy

  Lee Hall Capital City Real Estate Group

  625 E Washington St, Monticello, FL 32344
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  /2

  $470,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  51 Tarn Way, Monticello, FL 32344

  **Photos Coming Soon! Home will be move in ready May 20th. Amazing new construction 3 bedroom 2 bathroom plus office. Luxurious master suite, Kitchen made of dreams, this is a must see!

  Amber McKinney Hamilton Realty Advisors LLC

  51 Tarn Way, 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
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  /38

  $449,900

  • 3 Beds
  • 2 Baths
  • 1,774 Sq Ft

  107 S Tarn Way, Monticello, FL 32344

  Welcome to this beautifully custom-built 3 bedroom, 2 bath home completed in 2024 and located in the desirable Hemings Pond Subdivision. Offering the perfect blend of modern construction and thoughtful upgrades, this move-in ready showcases luxury vinyl plank flooring, upgraded light fixtures, premium countertops, and elegant bath fixtures. Owner selected custom enhancements elevate the space

  Joana Villeneuve Hill Spooner & Elliott Inc

  107 S Tarn Way, Monticello, FL 32344
• 

  

  /31

  $434,000

  • 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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  /70

  $795,000

  • 3 Beds
  • 2.5 Baths
  • 2,160 Sq Ft

  660 Whispering Hill, Monticello, FL 32344

  Set on 18+ acres of beautifully maintained pasture, this private country property is built for both everyday living, true equestrian use or small livestock farm. The land is the star- fully fenced with new wood fencing that cleanly defines multiple pastures, a peaceful pond, and wide open space to ride, graze and enjoy. The 6-stall horse barn is ready to work with paddocks attached to each stall,

  Catherine Hope All Realty Services

  660 Whispering Hill, Monticello, FL 32344
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  /31

  $625,000

  • 4 Beds
  • 3 Baths
  • 2,716 Sq Ft

  140 Shumard Ct, Monticello, FL 32344

  Discover this stunning 2,600+ sqft home built in 2021, offering the perfect blend of quiet country living and modern convenience. Features include: 4 spacious bedrooms and 3 full bathrooms 2 master bedrooms located downstairs Dedicated office/bonus room – ideal for work or hobbies Modern kitchen and open living spaces Attached 2-car garage Just minutes from downtown, providing a quick and easy

  Caleb Stephens Silo Hill Properties

  140 Shumard Ct, Monticello, FL 32344
• 

  

  /19

  $470,000 New Construction

  • 4 Beds
  • 3 Baths
  • 1,798 Sq Ft

  855 S Waukeenah St, Monticello, FL 32344

  Stunning New Construction recently built by Southern Construction. Centrally located in downtown Monticello, with mature landscaping, and plenty of room for the family. This 4 bed and 3 bath home features vinyl plank flooring, granite countertops, walk in tile shower and tub in master, upgraded trim package, and stainless appliances. Nice large back porch with deck, over looking the large

  Jared Parramore Coastwise Realty

  855 S Waukeenah St, Monticello, FL 32344
• 

  

  /3

  $775,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,377 Sq Ft

  693 Tally Hills Dr, Monticello, FL 32344

  New Construction. Images are renderings. 4-bedroom, 3-bath home coming soon in Tally Hills Estates. Construction has started on this beautifully designed, new construction home set on over 5 acres.

  Shelley Poppell Clover Key Realty

  693 Tally Hills Dr, Monticello, FL 32344
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  /52

  $425,000

  • 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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  /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
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  /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

  $549,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,233 Sq Ft

  35 Tarn Way, Monticello, FL 32344

  2026 Nailed It Tallahassee Parade of Homes Entry! **Photos are of previous build home will have different finishes. Home will be move in ready May 20th. Amazing new construction 4 bedroom 3 bathroom. Luxurious master suite, Kitchen made of dreams, this is a must see!

  Amber McKinney Hamilton Realty Advisors LLC

  35 Tarn Way, Monticello, FL 32344
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  /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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  /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
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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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  /16

  $40,000

  • 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
• 

  

  /22

  $95,000

  • 3 Beds
  • 2 Baths
  • 1,125 Sq Ft

  295 W J Hatchett Rd, Lamont, FL 32336

  Investor special with great potential! Situated on approximately .75 acres in Jefferson County, this 2022 mobile home offers a fantastic opportunity for the right buyer to complete the final steps and make it their own. Conveniently located just minutes from I-10 for easy access to Tallahassee and only about 10 minutes to downtown Monticello, the property combines rural space with excellent

  Catherine Hope All Realty Services

  295 W J Hatchett Rd, Lamont, FL 32336
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  /54

  $135,000

  • 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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  /24

  $174,900

  • 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 Drake Realty, Inc.

  963 Quail Ln, Monticello, FL 32344
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  /11

  $170,000

  • 2 Beds
  • 1 Bath
  • 962 Sq Ft

  275 W High St, Monticello, FL 32344

  This cozy home is situated in the heart of charming Monticello within walking distance to all the local shops and restaurants. It's perfect for a starter home or someone wanting to downsize for simplicity. The home features an open concept with plenty of natural light from the many windows. Use two barstools at the kitchen island, or set a nice table for a more formal dining experience. The

  Heather Boyd FL-GA Realty & Auction

  275 W High St, 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
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  /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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  /2

  $349,000

  • 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
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  /11

  $45,000

  • Land
  • 5.01 Acres
  • $8,982 per Acre

  TBD Aucilla Plantation Ct, Greenville, FL 32331

  5.01 wooded acres, well known for the large amount of Indian Artifacts due to the nearby Aucilla River, beautiful native trees, close to Smokehouse boat landing, Aucilla Shores Subdivision contains a private airstrip, animal Friendly & only a couple miles off Ashville Highway on well maintained roads.

  Justin Peel Maclay Realty & Management LLC

  TBD Aucilla Plantation Ct, Greenville, FL 32331
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  /12

  $399,000

  • Land
  • 60 Acres
  • $6,650 per Acre

  0 Fallow Rd Unit 373902, Lamont, FL 32336

  Private recreational tract located in western Jefferson County surrounded by very large managed private tracts. The quality of game rivals the best low fence hunting Florida has to offer. White tailed deer, wild turkey, ducks and bears. Owners have seen no sign of wild hogs. The 60 acres has good access off Fallow Road with building sites on both sides of the road. The majority of the acreage is

  Monroe Rogers Landcorp, Inc.

  0 Fallow Rd Unit 373902, Lamont, FL 32336
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  /8

  $29,000

  • Land
  • 14,374 Sq Ft
  • $87,879 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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  /31

  $275,000

  • 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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  /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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  /12

  $128,900

  • Land
  • 6.86 Acres
  • $18,790 per Acre

  1407 S Jefferson St, Monticello, FL 32344

  This property presents a strong commercial opportunity along the highly visible Hwy 19 corridor. The property consists of approximately 6.8± acres of B-2 Highway Commercial land with over 400± feet of frontage on Highway 19, offering excellent exposure and accessibility in a growing retail and service trade area.The site includes an approved development plan; however, the only designated

  Sam Ameen Xcellence

  1407 S Jefferson St, Monticello, FL 32344
• 

  

  /13

  $65,000

  • 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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  /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
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  /33

  $999,900

  • 3 Beds
  • 2.5 Baths
  • 4,383 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
• 

  

  /29

  $84,000

  • Land
  • 6.4 Acres
  • $13,125 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
• 

  

  /25

  $400,000

  • 4 Beds
  • 3 Baths
  • 2,870 Sq Ft

  49 Foggy Ln, Monticello, FL 32344

  Welcome to 49 Foggy Lane in Monticello, FL—an exceptional opportunity to own a spacious property with endless potential! This 2,870 sq ft home features 4 generously sized bedrooms and 3 full bathrooms, along with a dedicated office space—perfect for remote work or added flexibility. Enjoy cozy evenings by the wood-burning fireplace, creating a warm and inviting atmosphere throughout the home. The

  Chellise Harrell Superior Realty Group LLC

  49 Foggy Ln, Monticello, FL 32344

Showing Results 41 - 80, Page 2 of 3