Homes for Sale in 32344

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  /32

  $52,500

  • Land
  • 8 Acres
  • $6,827 per Acre

  983 Mays Rd, Lamont, FL 32344

  Affordable recreational parcel! Buy now, build later. Ultimate weekend escape or future homestead offering fun, freedom and fresh air- 7.69 serene acres split on both sides of scenic Mays Road. Enjoy the best of two offerings: West side 5.3 acres +/- with the pond, partially cleared with lush pasture, mature shade trees and wide-open space, perfect for horses, livestock, camping, four wheeling,

  

  Lynette Sirmon

  All Realty Services

  (448) 678-1146

  983 Mays Rd, Lamont, FL 32344
• 

  

  

  /21

  $349,000

  • Land
  • 15 Acres
  • $23,267 per Acre

  0000 Waukeenah Hwy, Monticello, FL 32344

  This stunning 15 acre property offers a mix of open land and wooded areas, providing a serene and private setting. Approximately 2 acres are equipped with an irrigation system, ideal for gardening, landscaping or small farming. This property includes a well-maintained barn with four spacious horse stables, perfect for equestrian enthusiasts. Power, well, and septic are already in place, making

  

  Shanna D'Attile

  Keller Williams Town & Country

  (850) 809-9683

  0000 Waukeenah Hwy, Monticello, FL 32344
• 

  

  

  /12

  $175,000

  • Land
  • 10 Acres
  • $16,714 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
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  /8

  $22,000

  • Land
  • 1.18 Acres
  • $18,644 per Acre

  874 Flatwoods, Monticello, FL 32344

  A square 1.18 acres with paved road frontage. It has a powerline easement that runs through the center of the property. It has several, abandoned, old mobile homes on the property (no titles will be given, only bill of sale) and other structures. It has about 50% wet lands and a portion of the property lies within the flood zone. It is wooded, with some, young, easy to mulch, growth and some

  

  Lynette Sirmon

  All Realty Services

  (448) 218-0926

  874 Flatwoods, Monticello, FL 32344
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  /42

  $469,000

  • 5 Beds
  • 2 Baths
  • 2,184 Sq Ft

  10283 Ashville Hwy, Greenville, FL 32331

  Amazing opportunity to own this private solar-powered farm with a large house! Beautiful and serene 16 acres with fruit trees, fields, lots of horse potential and 40 solar panels less than 5 years old. Nearly free electric! 5 Bedroom, 2 Bath with Large Eat-in Kitchen, Stainless Steel Appliances, Huge Great Room, Beautiful Hardwood Floors throughout main floor of the house, TWO Large Screened-in

  Lee Hall Capital City Real Estate Group

  10283 Ashville Hwy, Greenville, FL 32331
• 

  

  /38

  $419,000

  • 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.

  Steve Walker Steve C. Walker Realty, LLC

  339 Silver Lake Rd, Monticello, FL 32344
• 

  

  /19

  $350,000

  • Land
  • 70 Acres
  • $4,968 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

  265 Neely Rd, Monticello, FL 32344
• 

  

  /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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  /42

  $1,125,000

  • 3 Beds
  • 1 Bath
  • 1,146 Sq Ft

  740 Kinsey Rd, Monticello, FL 32344

  Location: Jefferson County, FL Size: 155 acres Features: Rolling pastures Planted pines Natural hardwoods Pond Home: 1941 built 1,146 square feet Updated Outbuildings: With power Opportunities for workshops, storage, and more Additional Homesites: Breathtaking views Peaceful living Proximity: 10 miles from downtown Monticello, FL 5 miles to I-10 Wildlife: Deer Turkey Waterfowl

  Ben Jones Southern Land & Homes

  740 Kinsey Rd, Monticello, FL 32344
• 

  

  /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
• 

  /2

  $25,000

  • Land
  • 0.39 Acre
  • $64,103 per Acre

  0 Tram Rd Unit 21473387, Monticello, FL 32344

  Wooded lot located in the Wacissa area of Jefferson County; 15 to Tallahassee. Community water available to hook up to.Copyright © 2025 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

  0 Tram Rd Unit 21473387, Monticello, FL 32344
• 

  

  /6

  $471,000

  • Land
  • 58 Acres
  • $8,057 per Acre

  1310 Piney Woods Rd, Monticello, FL 32344

  This property contains three tax ID number. The other 2 numbers are: 03-1N-4E-0000-001F-0000 and 03-1N-4E-0000-001E-0000. A total of 58.46 acres; currently there is no for sale sign on the property. Very nice wooded tract with great location; easy access to Tallahassee. It has timber potential and would be a good home tract also. Community water is available for the property along with high speed

  Steve Walker Steve C. Walker Realty, LLC

  1310 Piney Woods Rd, Monticello, FL 32344
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  /38

  $7,800,000

  • Land
  • 3,089 Acres
  • $2,525 per Acre

  0 Turkey Scratch Rd Unit 18561092, Monticello, FL 32344

  Turkey Scratch Road Timberland is 3,089 Acres in Jefferson County just outside Monticello. The property features 616 Upland Acres (20%) / 2473 Wetland Acres (80%) and has 4 miles of combined road frontage on I-10, 4,450 feet of road frontage on Turkey Scratch Road, and 1,725 feet on Aucilla Road. It also has several miles of well-maintained internal roads for easy navigation and timber

  Richard Dempsey Saunders Land

  0 Turkey Scratch Rd Unit 18561092, Monticello, FL 32344
• 

  /2

  $748,000

  290 Oetinger Rd, Monticello, FL 32344

  Land Description for 290 Oetinger Rd, Campbell Farm Welcome to the enchanting Campbell Farm, a sprawling 68-acre property nestled in the serene landscapes of Northern Jefferson County, Florida. This unique piece of real estate offers a harmonious blend of natural beauty and practical amenities, making it an ideal sanctuary for nature lovers and those seeking a peaceful retreat. Property

  Charles Ward Hayden Outdoors Real Estate

  290 Oetinger Rd, Monticello, FL 32344
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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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  /42

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,921 Sq Ft

  2497 Boston Hwy, Monticello, FL 32344

  Charming Hillside Country Retreat with Barn and Acreage. Welcome to your dream countryside escape! This beautifully maintained brick home sits peacefully on a hillside, surrounded by sprawling fields dotted with mature pecan trees. Inside, the home features a spacious open floor plan, perfect for entertaining or relaxing with family. The large kitchen offers ample workspace and storage, while the

  Pam Kelly Kelly & Kelly Properties, Inc

  2497 Boston Hwy, Monticello, FL 32344
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  /39

  $635,000

  • 3 Beds
  • 2.5 Baths
  • 2,546 Sq Ft

  181 Heritage Blvd, Monticello, FL 32344

  Highly Desirable Heritage Hills Location! Enjoy the perfect blend of privacy and convenience with this Craftsman-style home located on 3 serene acres, 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 year-round on the

  Pam Kelly Kelly & Kelly Properties, Inc

  181 Heritage Blvd, Monticello, FL 32344
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  /34

  $499,000

  • 8 Beds
  • 4 Baths
  • 4,806 Sq Ft

  2664 W Washington Hwy, Monticello, FL 32344

  FULLY RENOVATED TWO HOUSES, 1.9 acres, on picturesque US 90 near Monticello. UNDER $99/SF! These move-in-ready homes in good condition have a total of 8 bedrooms, 4 baths, and 4,806 s.f. living area. The MAIN HOUSE is a 1950’s era brick ranch-style home with new plumbing, new electric, fresh paint, new roof, whole home generator. Great opportunity for multiple generations to live side by side, or

  Heather Boyd FL-GA Realty & Auction

  2664 W Washington Hwy, Monticello, FL 32344
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  /39

  $539,000

  • 3 Beds
  • 2.5 Baths
  • 2,792 Sq Ft

  160 Lineage Ct, Monticello, FL 32344

  Beautiful 3-bedroom, 2.5-bath farmhouse offers privacy, charm, and modern conveniences. Built in 2016 and tucked away at the end of a cul-de-sac on 2.78 acres in desirable Heritage Hills. Home features an iron gate and long driveway—plenty of extra room for your boat or RV—along with a metal roof, a classic rocking chair front porch, large covered patio for entertaining and a 2-car garage.

  Leanne Groom The Naumann Group Real Estate

  160 Lineage Ct, Monticello, FL 32344
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  /63

  $519,000

  • 3 Beds
  • 2 Baths
  • 2,170 Sq Ft

  282 Long Leaf Dr, Monticello, FL 32344

  Enjoy space, privacy, and outdoor living on this well-maintained 5-acre property in Monticello. Tucked away on a private dirt road, this 3-bedroom, 2-bathroom home offers a functional 2,170 square foot layout with plenty of natural light. Outside is where this property really shines—featuring a screened-in patio, a sparkling pool with a Baja shelf, and multiple outdoor entertaining areas

  Catherine Hope All Realty Services

  282 Long Leaf Dr, Monticello, FL 32344
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  /28

  $399,000

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

  1205 E Pearl St, Monticello, FL 32344

  Charming 1956 Mid-Century Home. Fully Renovated with Modern Touches. Welcome to this beautifully reimagined 1956 classic, where character meets contemporary luxury. Every inch of this home has been thoughtfully renovated, blending original charm with stylish, modern upgrades. Step inside to discover a bright, open-concept living space featuring new floors, recessed lighting, and large windows

  Brian Bachman Kelly & Kelly Properties, Inc

  1205 E Pearl St, 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
• 

  

  /40

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,985 Sq Ft

  480 W Washington St, Monticello, FL 32344

  OWNERS MOTIVATED-ALL REASONABLE OFFERS WILL BE CONSIDERED.Step Back In Time! Rare chance to own your own piece of "Old Florida". Craftsman Style beauty with soaring 10 ' bead-board ceilings and 10 " baseboards, original pine floors and 4 gas fireplaces. Perfect blend of old Florida charm and modern conveniences. Statuary Marble countertops and copper sink in kitchen, extra large dining room for

  Pam Kelly Kelly & Kelly Properties, Inc

  480 W Washington St, Monticello, FL 32344
• 

  

  /19

  $430,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,865 Sq Ft

  173 Deerfield Ln, Monticello, FL 32344

  NEW CONSTRUCTION COMPLETE! Walk into this stunningly crafted three-bedroom, two-bathroom home that is perfectly rooted on a corner lot just a few miles from town. Situated on a full acre of land, this charming property is a rare find, free from HOA restrictions—giving you the freedom to personalize your space as you wish. Inside, you'll discover an open and welcoming floor plan that includes

  Caleb Stephens Silo Hill Properties

  173 Deerfield Ln, Monticello, FL 32344
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  /41

  $460,995 New Construction

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

  47 Mire Ct, Monticello, FL 32344

  Amazing new construction 3 bedroom 2 bathroom by Nailed It Tallahassee LLC Come pick out all your finishes, home scheduled for completion August 2025. Luxurious master suite, Kitchen made of dreams, this is a must see! Preferred Lender offering 1% in closing costs! Photos of previous home come make this one your own!

  Amber McKinney Hamilton Realty Advisors LLC

  47 Mire Ct, Monticello, FL 32344
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  /41

  $329,500

  • 4 Beds
  • 2 Baths
  • 2,162 Sq Ft

  4081 Gamble Rd, Monticello, FL 32344

  Nestled on a serene 5-acre retreat, this charming storybook cottage feels like a hidden gem, yet it’s just 15 minutes from downtown Monticello’s quaint shops and restaurants. Tucked back from the road for ultimate privacy, this well-maintained home is surrounded by natural beauty, including native plants, wild azaleas, and lush greenery. Step onto the inviting front porch and into a warm,

  Malissa Henning EXP Realty, LLC

  4081 Gamble Rd, Monticello, FL 32344
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  /4

  $209,900

  • 3 Beds
  • 2 Baths
  • 1,678 Sq Ft

  85 Pine Cone Dr, Monticello, FL 32344

  This beautifully renovated 3-bedroom, 2-bathroom modular home offers modern comfort and style. Inside, you'll find granite countertops, all new appliances, and updated finishes with a thoughtful layout perfect for both daily living and entertaining. A brand-new roof was installed in July 2025, and the HVAC system was replaced in October 2021, ensuring long-term peace of mind. Enjoy the outdoors

  Gabriela Sacco All Realty Services

  85 Pine Cone Dr, Monticello, FL 32344
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  /8

  $4,500,020

  • Land
  • 85 Acres
  • $52,780 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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  /28

  $239,000

  • 3 Beds
  • 2 Baths
  • 1,234 Sq Ft

  44 Pine Needle Trace, Monticello, FL 32344

  Charming Home with Open Floor Plan in Beautiful Monticello, FL! Welcome to this cozy well maintained home featuring an inviting open floor plan, warm wood-burning fireplace and vaulted ceilings that add space and character. French doors off the main living area open to a spacious deck overlooking the backyard. Freshly pained throughout the interior. Seller offering a flooring allowance with

  Pam Kelly Kelly & Kelly Properties, Inc

  44 Pine Needle Trace, Monticello, FL 32344
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  /46

  $178,000

  • 3 Beds
  • 3 Baths
  • 2,635 Sq Ft

  18 Perkins Williams Rd, Monticello, FL 32344

  Opportunity to finish a traditional-style home on 2.02 acres in the Monticello countryside. Built in 2001 by a local contractor, the home is approximately 80% complete and has never been lived in. The structure needs a new roof, HVAC system, water heater, bedroom flooring, and completion of the master bath. There is visible foundation settlement—cause and extent unknown. Located in a flood

  Ashley Hartsfield Keller Williams Town & Country

  18 Perkins Williams Rd, Monticello, FL 32344
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  /70

  $1,050,000

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

  825 Rainey Run, Monticello, FL 32344

  Welcome to this rare Monticello, FL luxury home for sale on 10 pristine acres with private creek frontage. This 4-bedroom, 4.5-bathroom estate spans nearly 3,700 square feet of elegant living space, offering the perfect blend of privacy, acreage, and modern luxury just minutes from Tallahassee. Property Highlights: 10 acres with a private creek 4 bedrooms, 3 with ensuite bathrooms 3,696 sq. ft.

  Renee Dawkins Ketcham Realty Group, Inc.

  825 Rainey Run, Monticello, FL 32344
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  /70

  $989,000

  • 4 Beds
  • 3 Baths
  • 4,600 Sq Ft

  2024 Old Lloyd Rd, Monticello, FL 32344

  Square footage includes both the main house is 3200 square feet with 4 bedrooms and 3 baths. New barn apartment is 1400 square feet with 2 bedrooms and 1 bath. This would be an amazing income producing property for short and/or long term rental property of barn apt, horse boarding stables ... or even a wedding venue. This breathtaking property checks ALL of the boxes! Please see associated

  Katherine Hansli Searcy The Naumann Group Real Estate

  2024 Old Lloyd Rd, Monticello, FL 32344
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  /43

  $295,000

  • 3 Beds
  • 2 Baths
  • 2,044 Sq Ft

  300 Cedar St, Monticello, FL 32344

  Welcome to 300 Cedar Street ~ Located a stone's throw from Monticello's charming downtown, yet quiet & private ~ Relax in a rocking chair & enjoy sitting on your HUGE 64x8 screened in porch that runs the entire length of the back of the home & overlooks the serene 1.5 acre lot ~ Built in 1958, this single story home is a sturdy brick ranch style with 3 Bedrooms, 2 Baths, extra large attached 2

  Jonathan Rigsby Spotlight Real Estate

  300 Cedar St, Monticello, FL 32344
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  /38

  $799,000

  • 5,139 Sq Ft

  625 E Washington St, Monticello, FL 32344

  Amazing Investment Opportunity! 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 as a rooming house with tenants. New roof 2024, new HVAC 2022 and mini splits, New kitchen and bathrooms 2022, Tankless Hot water

  Lee Hall Capital City Real Estate Group

  625 E Washington St, Monticello, FL 32344
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  /45

  $275,000

  • 4 Beds
  • 2 Baths
  • 1,812 Sq Ft

  685 E Washington St, Monticello, FL 32344

  Perfect brick family home right downtown! Walk to the veggie stand across the street and all the Monticello shops! Renovated 4-bed, 2-bath home. New roof!! New Custom Kitchen cabinets, granite counters, and SS Appliance package perfect for all those home chefs. The open-plan kitchen opens directly into the dining and living room. New Flooring, Paint, Light fixtures, Custom closets and bookcases

  Lee Hall Capital City Real Estate Group

  685 E Washington St, Monticello, FL 32344
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  /33

  $189,000

  • Land
  • 11 Acres
  • $17,797 per Acre

  720A Indian Hills Rd, Monticello, FL 32344

  Escape to the countryside and live your dream on this stunning 10.62-acre property! With three mobile homes currently on site, this property offers a unique opportunity for multi-generational living, rental income, or a sprawling family compound. While the mobile homes are not considered valuable, they provide a canvas for renovation or replacement. See potential in these structures or consider

  Alicia Radtke All Realty Services

  720A Indian Hills Rd, Monticello, FL 32344
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  /33

  $215,900

  • 2 Beds
  • 2 Baths
  • 1,356 Sq Ft

  1065 S Mulberry St, Monticello, FL 32344

  This cozy home located in the heart of Monticello is the perfect 2/2 for a starter family looking to settle down or someone looking for a small, southern home in a quiet town! There is so much potential with good bones from the old hardwood floors to the floor-to-ceiling windows. This home is in walking distance to the roundabout near restaurants and antique shops or to the grocery store. With a

  Katherine Gonzalez Pearson Realty Inc.

  1065 S Mulberry St, Monticello, FL 32344
• 

  

  /52

  $215,000

  • Land
  • 40 Acres
  • $5,375 per Acre

  3978 Quitman Hwy S, Greenville, FL 32331

  Welcome to 3978 S Quitman Hwy – 40 beautiful acres in the heart of Jefferson County, Florida. This versatile property is ideal for those seeking a private hunting retreat, weekend getaway, or future homesite. Over a quarter of the land is planted in pines, providing both aesthetic value and future timber potential. An older mobile home sits on-site, holding little value, but all essential

  Benjamin Sadler OaksFeather Realty

  3978 Quitman Hwy S, Greenville, FL 32331
• 

  

  /34

  $269,000

  • 3 Beds
  • 2 Baths
  • 1,654 Sq Ft

  130 Simpson Ave, Monticello, FL 32344

  Beautiful home located in historic Monticello within walking distance to downtown shopping, restaurants, and farmers market. Featuring 3 spacious bedrooms with 2 large bathrooms and a walk-in closet. This charming cottage has an extra office/study area, original fireplace, glass french doors to dining room and updates throughout while staying true to its original character. Step outside to a

  Suzanna Malone Lauer Real Estate Group LLC

  130 Simpson Ave, Monticello, FL 32344
• 

  

  /14

  $179,000

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  375 Maple St, Monticello, FL 32344

  Affordable home nestled in the heart of Monticello! This spacious home sports a freshly painted open floor plan. Wood finished line this home sharing a feeling of craftsmanship. Updated appliances make this home walk in ready for its next family. Nestled on a corner lot, this home has great curb appeal.

  Caleb Stephens Silo Hill Properties

  375 Maple St, Monticello, FL 32344

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