Jefferson County FL Homes for Sale

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  /41

  $472,500

  • 2 Beds
  • 2 Baths
  • 2,499 Sq Ft

  75 E 5th Ct, Greenville, FL 32331

  Airpark Community! Two Homes - One for YOU and one for THEM! Together the total sq. footage is 2499, one is 1152 sq. ft and the other one is 1347 sq. ft. All on 5 acres bordering the taxi way to the grass airstrip for 74FL Jefferson Landing Airport with a 6395 foot long grass strip including a huge barn/airplane hangar 60x48, a 4-Bay Pole Barn 20x40, detached office 16x30 , walk in 8x12

  

  Lynette Sirmon

  All Realty Services

  (850) 790-9281

  75 E 5th Ct, Greenville, FL 32331
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  /3

  $145,350

  • Land
  • 51 Acres
  • $2,850 per Acre

  000 Kinsey Rd, Monticello, FL 32344

  60.6 Acres of prime hunting/recreational land. Paved road access with owned easement. Wolf creek runs thrugh part of the property. $2850/Acre

  

  Buddy Witmer

  Steve C. Walker Realty, LLC

  (850) 726-3832

  000 Kinsey Rd, Monticello, FL 32344
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  /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
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  /36

  $95,000

  • 4 Beds
  • 2 Baths
  • 2,152 Sq Ft

  955 E Pearl St, Monticello, FL 32344

  Circa 1920, 3 Bdrm, 2 Bath, has 2 extra lots available for a total purchase price of $165,000.00, Home is fully livable as it is and can be purchased for $95,000.00 with lot size 109x135. However, to qualify for insurance, updates to the wiring & roof replacement will be necessary. Sold "AS IS" with right to inspect. Price reflects need for renovations and will not pass 4 Point Inspection! Two

  

  Lynette Sirmon

  All Realty Services

  (850) 757-1853

  955 E Pearl St, Monticello, FL 32344
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  /17

  $24,997

  • Land
  • 0.86 Acre
  • $29,066 per Acre

  98 Cox Rd, Monticello, FL 32344

  Small, tract of land "bring the chickens, build a chicken coop" located between Monticello, FL and Thomasville, GA. This UNIQUE, .86 acres of land with its deeply, rich, flora and native fauna is thick and abundant with many different types of indigenous species. Use the 10x20 storage building as a primitive bunkhouse cabin, specimen container, wildlife observatory or weekend landing pad/fun

  

  Lynette Sirmon

  All Realty Services

  (850) 990-4427

  98 Cox Rd, Monticello, FL 32344
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  /5

  $275,000

  • Land
  • 3.30 Acres
  • $83,333 per Acre

  xxx W Washington St, Monticello, FL 32344

  **Prime Investment Opportunity: 3.3 Acre Lot in Monticello Growth Area** For Sale: A 3.3 acre lot situated in the highest traffic area of Monticello, offering unparalleled visibility and access. Located in the largest growth zone of Monticello, this property is ideally positioned to benefit from the eastward expansion of Tallahassee. It is conveniently near several of the most desirable

  

  Tina Coombs

  Big Fish Real Estate Services

  (850) 318-4086

  xxx W Washington St, Monticello, FL 32344
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  /16

  $609,878

  • Land
  • 122 Acres
  • $4,999 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

  $1,300,000

  • Land
  • 200 Acres
  • $6,500 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 and ready to be thinned. The next owner will be able to thin the pines to their specification in

  Bryant Peace Saunders Real Estate

  0 Gum Swamp, Greenville, FL 32331
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  /42

  $1,200,000

  • 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
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  /6

  $816,000

  • Land
  • 68 Acres
  • $12,000 per Acre

  290 Oetinger Rd, Monticello, FL 32344

  68 acres in Northern Jefferson County Fl. Beautiful Pasture surrounded by Old Growth Pine Timber. Pond sits in the middle of the property and this property has a Plantation on Two sides. Well, Septic Tank and Barn are included with property. Deer and Turkey are abundant with an excellent spot for a Dove Field. Minutes from Monticello Fl. and Thomasville Ga. this is an ideal spot for someone

  Charles Ward Hayden Outdoors Real Estate

  290 Oetinger Rd, Monticello, FL 32344
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  /3

  $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

  Steve Walker Steve C. Walker Realty, LLC

  1310 Piney Woods Rd, Monticello, FL 32344
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  /42

  $495,900 New Construction

  • 3 Beds
  • 2 Baths
  • 2,061 Sq Ft

  350 Oconee, Monticello, FL 32344

  Welcome to Covey Run, a private estate community in the heart of Monticello. Your new 3 bedroom 2 bath 2 car garage sits on 2.24 acres. Home features open floor plan with primary on-suite and large walk-in closet. Kitchen is ready for the chef in mind with gas range and plenty of room for prep. Living room features 10 foot ceilings, fireplace and opens to a sunroom. House has Generac Home

  Steve Walker Steve C. Walker Realty, LLC

  350 Oconee, 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
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  /37

  $419,900

  • 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

  205 N Rhodes St, Monticello, FL 32344
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  /26

  $750,000

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

  5080 Ashville Hwy, Monticello, FL 32344

  Welcome to your dream getaway nestled on the pristine bank of Silver Lake! This beautiful cabin style home has 3-bedroom, 2-bathroom and seamlessly combines rustic charm with modern conveniences, making it the perfect escape for families or those seeking tranquility on the edge of town. The cabin showcases stunning hardwood floors that add warmth and elegance to the living space. Enjoy your

  Caleb Stephens Waypoint Properties East

  5080 Ashville Hwy, Monticello, FL 32344
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  /40

  $419,000

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

  480 W Washington St, Monticello, FL 32344

  Step Back In Time! Rare chance to own your own piece of"Old Florida". Craftsman Style beauty with soaring 10 ' beadboard 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 family gatherings and entertaining. Covered front porch( 40

  Pam Kelly Kelly & Kelly Properties, Inc

  480 W Washington St, Monticello, FL 32344
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  /41

  $425,000

  • 5 Beds
  • 4 Baths
  • 3,330 Sq Ft

  4131 N Jefferson Hwy, Monticello, FL 32344

  3330 square foot home on a beautiful 6 acre property that backs up to Pine Haven Plantation! This is a solid brick home with a 2016 metal roof and a 2018 HVAC unit and well pump. The home was purchased back in 2023 and gutted along with some extensive repairs done to bones of the home. It is now waiting for the perfect person to come in and finish her out with their personal touches. The main

  Catherine Hope All Realty Services

  4131 N Jefferson Hwy, Monticello, FL 32344
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  /42

  $632,000

  • 4 Beds
  • 3.5 Baths
  • 3,862 Sq Ft

  3873 N Jefferson St, Monticello, FL 32344

  Stunning 4 Bedroom, 3.5 Bath Home on 9.73 Acres with Large Detached Garage plus Oversized Attached 2 Car Garage Located just north of this spacious 3,862 square foot home sits on 9.73 acres with a tranquil creek running through the rear of the property. The home is built on high and dry ground, and not located in a flood zone or HOA. Built in 2007, the home features 10-foot ceilings,

  Stephanie Dobson Southern Land & Homes

  3873 N Jefferson St, Monticello, FL 32344
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  /42

  $649,000

  • 3 Beds
  • 2.5 Baths
  • 2,560 Sq Ft

  181 Heritage Blvd, Monticello, FL 32344

  Craftsman style house in Heritage Hills subdivision~ The house features 3 bedrooms/2 bathrooms and is energy efficient (Green Certified) ~ Luxurious hardwood flooring and a deluxe primary bathroom with separate jetted tub & large shower ~ Custom built-in cabinets in the living room and office ~ Regal craftsman style interior trim throughout and stainless-steel appliances ~ Full Solar with

  Mariela Bartens Coldwell Banker Hartung

  181 Heritage Blvd, Monticello, FL 32344
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  /42

  $509,000

  • 4 Beds
  • 3 Baths
  • 2,555 Sq Ft

  4287 Bassett Dairy Rd, Monticello, FL 32344

  Rare COUNTRY Farmhouse OASIS AWAITS! – Discover the perfect blend of rustic charm in this stunning 5-bedroom, 3-bathroom home, nestled on five fully fenced acres of picturesque pastureland. Located just 15 minutes from downtown Monticello, this peaceful retreat offers breathtaking views, abundant wildlife, and plenty of space for your pets to roam. Step inside to a beautifully updated,

  Destiny Jones Keller Williams Town & Country

  4287 Bassett Dairy Rd, Monticello, FL 32344
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  /25

  $434,900

  • 4 Beds
  • 2 Baths
  • 1,809 Sq Ft

  115 Crooked Creek Ln, Monticello, FL 32344

  New Construction in Crooked Creek by Hannon Construction on .72 acre lot! This open plan features 4 bedrooms, 2 bathrooms and a 2 car garage (floor plan and survey are attached in associated docs). Wood LVP flooring throughout (tile in baths), GE stainless appliances, electric fireplace and pre-wired for security and surround sound. *Estimated completion date is May 1, 2025. There is still time

  Amber Renaud The Nova Group Realty

  115 Crooked Creek Ln, Monticello, FL 32344
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  /42

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,917 Sq Ft

  1288 Indian Hills Rd, Monticello, FL 32344

  Please show and bring back up offers. Peace is what you will find when you visit this lovely home on 5.66 acres. Mostly wooded with a flowing creek. Brick home has a brand new roof 2025. One owner home that has been meticulously taken care of. Open kitchen /living room with vaulted ceilings and a wood burning stove for cozy evenings. Family room has an office nook an a wall of windows for great

  Pam Kelly Kelly & Kelly Properties, Inc

  1288 Indian Hills Rd, Monticello, FL 32344
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  /42

  $735,000

  • 4 Beds
  • 2.5 Baths
  • 3,911 Sq Ft

  4589 Ashville Hwy, Monticello, FL 32344

  PRICED $35,000 BELOW RECENT APPRAISAL!! Welcome to your forever home on the most stunningly manicured 5.5+ acres nestled in a serene country setting. This is truly a showstopper starting right at the beginning with its grand gated entrance leading to a picturesque rocking chair front porch and a modern farmhouse aesthetic. Walking in the front door you’ll be greeted by a cathedral vault ceiling,

  Devin Lohman Lohman Realty LLC

  4589 Ashville Hwy, Monticello, FL 32344
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  /34

  $465,000

  • 4 Beds
  • 3 Baths
  • 2,076 Sq Ft

  376 Tecumseh Rd, Monticello, FL 32344

  Gorgeous multigenerational, ranch style, 4 Bedroom/3 Bath home with 5th room that can be used as an office or additional bedroom. Perfect for a growing or downsizing family! Home rests on 4.60 acres of outdoor, partially wooded paradise. Enjoy tranquility from the all-season rear porch-removable panels allow you to turn room into a screened porch in minutes. Many recent updates include freshly

  Casey Skelton Pearson Realty Inc.

  376 Tecumseh Rd, Monticello, FL 32344
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  /40

  $565,000

  • 3 Beds
  • 3 Baths
  • 2,661 Sq Ft

  141 Shumard Ct, Monticello, FL 32344

  This stunning 3-bedroom, 3-bath home is perfectly situated on a quiet cul-de-sac, offering the ideal blend of modern comfort and thoughtful upgrades, all on a fully fenced 0.90-acre lot. The spacious open floor plan is designed for both entertaining and everyday living, complemented by a gourmet kitchen with stainless steel appliances. The garage includes an added sink for extra convenience, and

  Kara Richetti Real Broker LLC

  141 Shumard Ct, Monticello, FL 32344
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  /27

  $439,000

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

  339 Silver Lake Rd, Monticello, FL 32344

  Beautiful private country setting with large oaks and open pasture! Extra roomy home with open concept kitchen/dining/living and wood burning fireplace. Bring the kids and the horses and chickens. Silver Lake Road is a dead end road which makes this property extra quiet and private. Lots of room to build a barn and/or workshop.

  Pam Kelly Kelly & Kelly Properties, Inc

  339 Silver Lake Rd, Monticello, FL 32344
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  /3

  $469,995 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,940 Sq Ft

  52 Mire Ct, Monticello, FL 32344

  Amazing new construction 3 bedroom 3 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

  52 Mire Ct, 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
• 

  

  /19

  $305,000

  • 4 Beds
  • 2 Baths
  • 1,858 Sq Ft

  575 E Palmer Mill Rd, Monticello, FL 32344

  Spacious home located within walking distance of Historic Downtown Monticello. This four bedroom home sits quietly on a manageable half acre lot. Sporting both original hardwood flooring and newly installed LVP flooring, this home blends perfectly for any new home owners. Updated bathrooms and appliances have all been done within the last 5 years. Sizes are approximate.

  Caleb Stephens Waypoint Properties East

  575 E Palmer Mill Rd, Monticello, FL 32344
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  /7

  $119,900

  • Land
  • 5 Acres
  • $23,191 per Acre

  0 Taylor Rd Unit 384618, Monticello, FL 32344

  5.17 acres Taylor Rd. Wonderful Jefferson County location. Minutes from I-10/ Gamble Rd. + downtown Monticello. New 5 lot mini subdivision paved frontage, minimal restrictions to protect values. See survey and site plans in associated docs. Underground County water available. Owner financing available. LAST LOT FOR SALE- SELLER WILL GIVE CLEARING AND SEPTIC ALLOWANCE.

  Kevin Davis The Naumann Group Real Estate

  0 Taylor Rd Unit 384618, Monticello, FL 32344
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  /4

  $89,000

  • Land
  • 4.42 Acres
  • $20,136 per Acre

  TBD Devane, Monticello, FL 32344

  Wooded 4.42 acres, peaceful location just on the outside of Monticello. Across from the Jefferson County Countyr Club.

  Barry Kelly Kelly & Kelly Properties, Inc

  TBD Devane, Monticello, FL 32344
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  /25

  $314,900

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft

  203 Pine Cone Dr, Monticello, FL 32344

  Shows like a brandd new home, Built in 2021 on half acre lot. Split floor plan with large dedrooms. Open foor plan with kitchen overlooking living space with 10 ft trey ceiling, granite countertops and custom cabinetry. Large master bedroom suite, walkin shower and walkin closet. 2 car garage, fenced backyard for the pets and privacy.

  Barry Kelly Kelly & Kelly Properties, Inc

  203 Pine Cone Dr, Monticello, FL 32344
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  /18

  $74,900

  • Land
  • 5 Acres
  • $13,870 per Acre

  Lot 16 Bear Hollow Rd, Greenville, FL 32331

  This off the beaten path, wooded 5.4 acres gives you the privacy, peacefulness and serenity you deserve in life! Deer, birds and wildlife sightings guaranteed and plentiful. It is perfect for year-round living or for that special get-a-way place. The large, mature oaks and scattered pines throughout, provide a natural canopy of shade and seclusion with several perfect home locations to choose

  Andrea White Sawgrass Realty, LLC

  Lot 16 Bear Hollow Rd, Greenville, FL 32331
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  /3

  $437,500

  • Land
  • 22 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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  /11

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,960 Sq Ft

  749 E Buckhorn Trail, Greenville, FL 32331

  Check out this spacious 4 bedroom, 2-bathroom home nestled on a generous 5.15-acre lot, offering a peaceful, country living experience. This property provides ample space for those seeking privacy, yet it's still close enough to the town's amenities. The home is designed with a open living space that maximize natural light and offers a welcoming atmosphere, The perfect balance of comfort and

  Bridget Davis Waypoint Properties East

  749 E Buckhorn Trail, Greenville, FL 32331
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  /3

  $117,036

  • Land
  • 11 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 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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  /4

  $8,000

  • Land
  • 0.25 Acre
  • $32,000 per Acre

  TBD Hangar Ln, Greenville, FL 32331

  Hangar lots, each lot approx 50 x 75, The plan was for plane storage but they can be used for other storage possibilities. The lots are cleared. The measurements are approx. Over 6000 ft grass runway.

  Barry Kelly Kelly & Kelly Properties, Inc

  TBD Hangar Ln, Greenville, FL 32331
• 

  

  /41

  $365,000

  • 2 Beds
  • 1.5 Baths
  • 1,140 Sq Ft

  265 Still Rd, Monticello, FL 32344

  This inviting 2-bedroom, 1.5-bath home sits on 5 peaceful acres between Monticello, FL, and Thomasville, GA, offering a great mix of indoor comfort and outdoor space. It’s just as cute as you want it, with endless potential for outdoor living! Inside, the open great-room layout feels both spacious and cozy, with a large utility room leading to the screened porch and a covered carport that’s

  Catherine Hope All Realty Services

  265 Still Rd, Monticello, FL 32344
• 

  

  /10

  $235,000

  • Land
  • 7 Acres
  • $33,571 per Acre

  1400 Gamble Rd, Monticello, FL 32344

  7 beautiful acres just right for your dream home! Power is on the property along with a 105' deep well. Mostly cleared with some pines and hardwoods.

  Kenneth Ayers Primesouth Fezler, Russell and

  1400 Gamble Rd, Monticello, FL 32344

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