Jefferson County FL Homes for Sale

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  /45

  $449,995 New Construction

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

  47 Mire Ct, Monticello, FL 32344

  Amazing new construction Available Now 3 bedroom 2 bathroom by Nailed It Tallahassee LLC Luxurious master suite, Kitchen made of dreams, this is a must see! Preferred Lender offering 1% in closing costs! Photos of current home!

  Amber McKinney Hamilton Realty Advisors LLC

  47 Mire Ct, 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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  /48

  $1,000,000

  • 8 Beds
  • 6.5 Baths
  • 5,560 Sq Ft

  237 Valley View Ct, Monticello, FL 32344

  Opportunities like this are rare! You've been seeking close in country life. Enjoy the perfect balance of privacy and convenience on 15 acres with a true Estate. A main home, guest home, efficiency apartment, barn, climate controlled storage, life sized doll house with electric, screened pool, and whole home generator offer the perfect multi-generational set up and breathtaking sunset views just

  Kelly Vinson Keller Williams Town & Country

  237 Valley View Ct, Monticello, FL 32344
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  /54

  $525,000

  • 4 Beds
  • 3 Baths
  • 2,784 Sq Ft

  70 Generation Ct, Monticello, FL 32344

  Wow! Special opportunity to add your personal touches! Design your dream kitchen! Craftsman style home features a roomy floorplan with lots of storage nooks and crannies, huge primary suite waiting for your perfect finishes, open kitchen and all nestled on private 4.45 acres. Many of the are there to finish trim, there’s extra stone and extra tile. LVP and ceramic tile flooring throughout home,

  Lee Duggar Re/Max Professionals Realty

  70 Generation Ct, Monticello, FL 32344
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  /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

  $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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  /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
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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
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  /35

  $650,000

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

  498 Heritage Blvd, Monticello, FL 32344

  Welcome to this beautifully crafted 3-bedroom, 2.5-bath Craftsman-style home nestled in the highly sought-after Heritage Hills community. Perfectly positioned on a spacious 2.99-acre lot, this property offers the ideal blend of privacy, room to roam, and timeless curb appeal—all with an easy commute to both Tallahassee and Monticello. Step inside to an inviting open-concept living area designed

  Brian Moser Bulldog Properties, LLC

  498 Heritage Blvd, Monticello, FL 32344
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  /29

  $489,000

  • 4 Beds
  • 2 Baths
  • 2,624 Sq Ft

  1142 Ashville Highlands, Greenville, FL 32331

  Nestled in the peaceful Ashville Highlands fly-in community, this custom 2600+ sq. ft. all-brick home offers space, privacy and quality construction 15 min east of Monticello. Built with insulated concrete form walls and a metal roof, the home is designed for durability and comfort. The five acre property includes a 24x24 metal outbuilding/garage, generator, 50 amp RV plug-in and parking, and

  Jennifer Lee Armor Realty, Inc

  1142 Ashville Highlands, Greenville, FL 32331
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  /60

  $525,000

  • 4 Beds
  • 2 Baths
  • 1,838 Sq Ft

  965 Robert Thompson Rd, Monticello, FL 32344

  Quiet country living near everything Tallahassee FL offers. Beautiful 4BR/2BA home on 5 acres. Split bedroom plan. Living room opens to large kitchen and breakfast nook. Sunroom not included in SqFt. Primary bedroom with tray ceilings, private bath with a jetted tub and separate shower. Plantation shutters throughout home. Generator installed 2017. 2 car attached garage and a large detached

  Suzanne McGhee Mattox Realty, Inc

  965 Robert Thompson Rd, Monticello, FL 32344
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  /19

  $480,000 Open Sat 12PM - 2PM

  • 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
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  /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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  /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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  /16

  $65,000

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft

  980 Mays St, Monticello, FL 32344

  Probate proceedings underway. Cannot close until court approval. Concrete Block 2/1 Home less than a mile from downtown Monticello! This quaint 888sqft home sits under a metal roof and only requires your vision and a little effort to become a superb starter home or investment opportunity. Property is fully fenced and on city utilities. Room measurements are approximate

  Ben Marinelli All Realty Services

  980 Mays St, Monticello, FL 32344
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  /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

  $149,000

  • 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

  $179,900

  • 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

  $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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  /57

  $230,000

  • 2 Beds
  • 1 Bath
  • 1,741 Sq Ft

  265 W Seminole Ave, Monticello, FL 32344

  You must see this -Charming all-brick corner-lot home ideally located directly across from the Legion Hall and the entrance to Monticello Ecological Park—plus just a short walk to midtown shops and restaurants. The screened In front porch welcomes you inside. Inside, you’ll find wood floors (including beneath the carpet in the bonus room) and a layout that offers flexibility for today’s living.

  Karen Gillispie Keller Williams Town & Country

  265 W Seminole Ave, 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 221 Kiley Road in Monticello, Florida — a rare estate where vineyard charm, equestrian living, and exceptional space come together to create an unforgettable lifestyle. This 5-bedroom, 3.5-bathroom estate is a true masterpiece, gracefully set on 5 private acres and complemented by a beautiful pool house with an additional bathroom. An additional adjoining 5-acre parcel is also

  Wilda Sigler Keller Williams Town & Country

  221 Kiley Dr, Monticello, FL 32344
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  /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
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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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  /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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  /42

  $325,000

  • 4 Beds
  • 3 Baths
  • 2,223 Sq Ft

  155 E Seminole Ave, Monticello, FL 32344

  Full of character, this spacious 1950s home offers 4 bedrooms and 3 full bathrooms on a generous 0.60-acre lot in the heart of Monticello. Are you looking for a home that you can run a business out of? This is the perfect place for that with Business/Residential zoning and great road frontage on the main thoroughfare into Monticello. With over 2,200 square feet—including two bedrooms with ensuite

  Catherine Hope All Realty Services

  155 E Seminole Ave, 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
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  /29

  $95,000

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  290 Parkway Pines Ct, Monticello, FL 32344

  Explore this three bedroom, two bathroom mobile home located on a little over half an acre in the Parkway Pines subdivision in Monticello Florida! Featuring newer carpet/vynil flooring throughout the home, a spacious front porch, and plenty of yard space for outdoor activities! Home is being offered "AS IS". Metal roof is about 3-5 years old. Original HVAC, duct work replaced summer 2025. All

  Alicia Radtke All Realty Services

  290 Parkway Pines Ct, Monticello, FL 32344
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  /28

  $174,999

  • 3 Beds
  • 2 Baths
  • 1,292 Sq Ft

  463 Murmuring Creek Rd, Monticello, FL 32344

  Move in ready home on over 5 acres in beautiful Monticello Florida. Newer Roof 2024, Freshly painted, , windows, hot water heater 2024, flooring. reduced price, No HOA

  Jennifer Atwell Ketcham Realty Group, Inc.

  463 Murmuring Creek Rd, Monticello, FL 32344
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  /36

  $674,900

  • 5,139 Sq Ft

  625 E Washington St, Monticello, FL 32344

  Amazing Investment Opportunity as a Large family home, multi-generational property or Cash flowing investment! Own your piece of history and enjoy some great cash flow in this beautiful Downton Monticello Home. Built in 1888 and almost 4500 SF in the main house with 9 bedrooms, 7 bathrooms and common areas for the tenants. Currently set up with tenants as a BNB type property with longer term

  Lee Hall Capital City Real Estate Group

  625 E Washington St, Monticello, FL 32344
• 

  

  /13

  $584,350

  • Land
  • 30.97 Acres
  • $18,868 per Acre

  Vacant Attatulga Rd, Lamont, FL 32336

  Discover the perfect blend of privacy and convenience with this beautiful 30-acre wooded parcel in Jefferson County. With a mix of towering pines and hardwoods, a picturesque creek runs through the center of this property, adding to the natural beauty and charm of the land. Nestled between Attatulga Rd and WPA Rd, you are afforded dual road access from the North and South. Zoned Ag-5, there are

  Catherine Hope All Realty Services

  Vacant Attatulga Rd, Lamont, FL 32336
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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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  /38

  $599,900 New Construction

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

  261 Hiawatha Farms S, Monticello, FL 32344

  Welcome to this stunning new construction masterpiece, meticulously designed and built by the esteemed Kasdorf Homes, 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 plan, perfect for modern living. The split floor plan provides privacy and

  Ross Kozloski Kozloski Realty, LLC

  261 Hiawatha Farms S, Monticello, FL 32344
• 

  

  /18

  $169,900

  • 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
• 

  

  /24

  $185,000

  • 3 Beds
  • 2.5 Baths
  • 2,467 Sq Ft

  490 E Palmer Mill Rd, Monticello, FL 32344

  This striking Victorian home built in 1892 and located near downtown Monticello. The home features original hardwood pine floors, soaring 12-foot ceilings, a large bay window with bench seating (and storage) and several fireplaces. The master bathroom has been completely redone and complements the spacious master bedroom. The exterior of the home has a wraparound front deck, a rear screened

  Van Drake Drake Realty, Inc.

  490 E Palmer Mill Rd, 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
• 

  

  /70

  $700,000

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  1627 Lloyd Creek Rd, Monticello, FL 32344

  Enjoy the gorgeous water views from the porch of this like-new, 2022 built home! A Gated driveway leads to your 5 acre parcel on a beautiful 10 acre spring-fed lake with great fishing. 6 ft windows and 8x8 sliding doors allow the open living, dining, and kitchen areas to view the sunny outdoors. Kitchen features a large island with seating area, stainless appliances, gas stove, and fridge with

  Nan Greynolds The Naumann Group Real Estate

  1627 Lloyd Creek Rd, Monticello, FL 32344

Showing Results 41 - 80, Page 2 of 3