Jefferson County FL Homes for Sale

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  /31

  $65,000

  • Land
  • 8 Acres
  • $8,453 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

  (850) 752-4623

  983 Mays Rd, Lamont, FL 32344
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  /42

  $349,000

  • 4 Beds
  • 4 Baths
  • 3,456 Sq Ft

  852 E Buckhorn Trail, Greenville, FL 32331

  Welcome to Your Hidden Hilltop Retreat! Perched atop a gentle rise (180 ft. above sea level) in Northeast Jefferson County, this three-story, 4-bedroom, 4-bathroom sanctuary offers a life lived deeply in tune with nature. Nestled on 5.11 acres of whimsical, lovingly tended land—where white-tailed deer browse the edges of a fenced garden and wild turkeys meander past the first floor, screened

  

  Lynette Sirmon

  All Realty Services

  (850) 930-1972

  852 E Buckhorn Trail, Greenville, FL 32331
• 

  

  

  /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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  /3

  $127,500

  • Land
  • 51 Acres
  • $2,500 per Acre

  000 Kinsey Rd, Monticello, FL 32344

  51 Acres of prime hunting/recreational land. Paved road access with owned easement. Wolf creek runs thrugh part of the property. $2500/Acre

  

  Buddy Witmer

  Steve C. Walker Realty, LLC

  (850) 726-3832

  000 Kinsey Rd, 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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  /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

  $1,125,000

  • 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
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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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  /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

  $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. More pictures coming next week.

  Steve Walker Steve C. Walker Realty, LLC

  339 Silver Lake Rd, Monticello, FL 32344
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  /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
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  /42

  $489,900 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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  /70

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,452 Sq Ft

  1291 Hayfield Spur, Monticello, FL 32344

  Escape to your own private retreat in Monticello, FL! This spacious 5-acre property features two private ponds and two large outbuildings—both equipped with utilities. One outbuilding functions as a workshop with additional storage and a bathroom, offering endless potential. The 2-bedroom, 2-bathroom home is full of charm, featuring vaulted ceilings, a wood-burning fireplace, and an abundance of

  Jason Naumann The Naumann Group Real Estate

  1291 Hayfield Spur, 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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  /42

  $614,900

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

  181 Heritage Blvd, Monticello, FL 32344

  Craftsman style house in Heritage Hills subdivision~ Seller contemplating backup contracts~ 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

  Mariela Bartens Coldwell Banker Hartung

  181 Heritage Blvd, Monticello, FL 32344
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  /40

  $465,000

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

  376 Tecumseh Rd, Monticello, FL 32344

  NEW ROOF being installed! 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

  Casey Skelton Pearson Realty Inc.

  376 Tecumseh Rd, Monticello, FL 32344
• 

  

  /18

  $759,000

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft

  5301 Gentle Breeze Dr, Tallahassee, FL 32309

  Rare find. 10+/- acres located in Leon County, Florida on Lake Miccosukee. Rustic homestead with 455 feet of breathkaking views of the lake. Very secluded with lots of privacy. 1,650 SF lodge/home included in sale. Fantastic ducking, deer and turkey hunting, as well as world class fishing in your backyard! Entire home Generac generator included. Gentle Breeze Drive is located approximately

  Gerald McArthur Gerald McArthur Gulf Coast Real Estate Advisors, LLC

  5301 Gentle Breeze Dr, Tallahassee, FL 32309
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  /27

  $450,000

  • 3 Beds
  • 2 Baths
  • 2,131 Sq Ft

  133 Devane Rd, Monticello, FL 32344

  Peaceful 10-Acre Country Retreat with Pool - Just Outside Chattahoochee, FL Discover the charm of country living with this spacious 3-bedroom, 2-bath single-family home located just minutes from the quaint town of Chattahoochee, Florida. Enter through the winding tree lined road that sets the stage for the home that welcomes you at the end. Set on a beautifully wooded 10-acre parcel, this 2,131

  Bubba McCants EXP Realty LLC

  133 Devane Rd, Monticello, FL 32344
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  /40

  $600,000 Open Sat 12PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 2,771 Sq Ft

  44 S Ojibwa Rd, Monticello, FL 32344

  Escape the hustle and enjoy peaceful country living with the convenience of modern amenities! This spacious 4 bedroom, 3.5 bathroom home offers 2,771 square feet of well-designed space sitting on 5 beautiful acres with producing pecan trees. Whether you're ready to start your homesteading journey or simply want more space and privacy, this property is ready for you. With plenty of room to grow,

  Brett Miller Hollifield Real Estate Group

  44 S Ojibwa Rd, Monticello, FL 32344
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  /42

  $685,000

  • 3 Beds
  • 2.5 Baths
  • 3,214 Sq Ft

  150 N Ojibwa Rd, Monticello, FL 32344

  Peaceful 5.10+ acre retreat in Objiwa Acres! This beautifully maintained 3BR/2BA home offers space, privacy, and flexibility—surrounded by a manicured lawn, rows of pecan trees, a dedicated herb garden, and a saltwater plunge pool with fountain. Enjoy multiple outdoor living spaces including a screened front porch, screened back porch, and a bright true Florida room with vaulted ceilings. A

  Hettie Spooner Hill Spooner & Elliott Inc

  150 N Ojibwa Rd, Monticello, FL 32344
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  /42

  $449,000

  • 4 Beds
  • 3 Baths
  • 2,832 Sq Ft

  4710 Waukeenah Hwy, Monticello, FL 32344

  Monticello living is good, peaceful living. This home is ready for a multi-generational family, or a family with loads of relatives and friends to entertain. This three bedroom, two bath home has an adjacent mother in law suite complete with bedroom, kitchen, bath and living room. Located on two acres with a 2025 a/c unit, 2019 roof, large screened and unscreened porch, 3 pad carport, 3

  Fay Armstrong Keller Williams Town & Country

  4710 Waukeenah Hwy, 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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  /24

  $430,000 New Construction

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

  173 Deerfield Ln, Monticello, FL 32344

  Welcome to this beautifully maintained 3-bedroom, 2-bath home offering the perfect blend of peaceful country living and modern upgrades. Nestled on a full acre of land, this charming property is a rare gem with no HOA restrictions—giving you the freedom to truly make it your own. Step inside and be captivated by the open and inviting floor plan, featuring both a formal living room and a cozy

  Pamela Jordan-williams Superior Realty Group LLC

  173 Deerfield Ln, 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
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  /27

  $325,000

  • 3 Beds
  • 1.5 Baths
  • 1,772 Sq Ft

  395 W Palmer Mill Rd, Monticello, FL 32344

  Check out this craftsman style home in the heart of Monticello. This 1920s charmer has 3 bedrooms, 1 & 1/2 baths, wrap around porches, fenced in yards (front and back) with sidewalks to the center of town just a few blocks away. This home was previously a daycare and could be again if you choose.

  Mark Vollertsen Advanced Real Estate Sales

  395 W Palmer Mill Rd, Monticello, FL 32344
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  /47

  $329,900

  • 3 Beds
  • 2 Baths
  • 1,370 Sq Ft

  1530 Sweetbay Ct, Monticello, FL 32344

  Beautiful 2021 built 3/2 home on quiet cul-de-sac across from a gorgeous green space with mature trees! Stunning light and bright features with an updated kitchen and baths, including laminate light oak wood flooring, granite counters, stainless appliances, covered back porch and two car garage. This home is a must-see!

  Amber Renaud The Nova Group Realty

  1530 Sweetbay Ct, Monticello, FL 32344
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  /18

  $139,000

  • 3 Beds
  • 2 Baths
  • 1,836 Sq Ft

  195 E Meadow Rd, Monticello, FL 32344

  NEW Metal ROOF 2022! Welcome to the Aucilla Forest & Meadows Subdivision! Spacious 1836 square foot double wide mobile home built in 1999. 3 bedroom, 2 full bathroom on huge 2.50 acre lot! ~10 minutes to Aucilla River! Only $75/sq ft! Home needs cosmetic work that can be done over time! Primary bedroom has shower stall, garden tub + large walk-in closet. Split floor plan, huge kitchen with tons

  Chelsey Hough Keller Williams Town & Country

  195 E Meadow Rd, Monticello, FL 32344
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  /4

  $289,900

  • 5 Beds
  • 3 Baths
  • 4,026 Sq Ft

  620 Hill St, Monticello, FL 32344

  Welcome to this charming home located at 620 Hill St in Monticello, FL. This delightful property features a spacious layout with multiple bedrooms and bathrooms, providing ample space for comfort and functionality. Enjoy the serene surroundings and beautiful exterior, complemented by a well-maintained yard. Inside, you'll find a bright and inviting living area, a modern kitchen, and elegant

  Steven Koleno Beycome of Florida LLC

  620 Hill St, Monticello, FL 32344
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  /27

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  140 E Buckhorn Trail, Greenville, FL 32331

  Welcome to this peaceful countryside retreat, located on a spacious, private lot in Greenville, FL. This charming 3-bedroom, 2-bath home combines warmth, functionality, and ample space both inside and out. As you enter, you'll find a bright and inviting living area with a wall of windows that allows natural light to pour in and provides serene views of the surrounding woods. The sunroom is a

  Christopher Worth Keller Williams Town & Country

  140 E Buckhorn Trail, Greenville, FL 32331
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  /42

  $375,000

  • 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. With over 2,200 square feet—including two bedrooms with en suite baths—it also features flexible zoning for residential, business, or mixed use. The layout includes a cozy living room with a fireplace and an airy sunroom, perfect for an office or casual

  Catherine Hope All Realty Services

  155 E Seminole Ave, Monticello, FL 32344
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  /16

  $99,900

  • Land
  • 5 Acres
  • $18,500 per Acre

  70 E 2nd Way, Greenville, FL 32331

  Off Grid Living? Fly a plane and Bring a horse. Paved Road frontage on this 5.40 acre parcel with perimeter fencing and cross fencing. Property was a total off-grid living arrangement at one point. Deep well with gravity made pressure tank. Solar shed and station. Tiny home with air conditioning. Feed Stall for the horse. Property was being maintained as a park like setting up until a few years

  Starbuck Rissman Steve C. Walker Realty, LLC

  70 E 2nd Way, Greenville, FL 32331
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  /36

  $154,700

  • 4 Beds
  • 2 Baths
  • 2,280 Sq Ft

  2265 Deerwood Blvd, Greenville, FL 32331

  Peace and tranquility can be yours in this great location when you bring your toolbox and give this home new life. With 4 bedrooms, a living room and family room, plus a bonus sitting room off the master, there is ample space for everyone to spread out and enjoy. The large kitchen features a center island, perfect for the family to gather. A large ensuite bath features a garden tub, a separate

  Jessica Webb A Main Street Realty Co, LLC

  2265 Deerwood Blvd, Greenville, FL 32331
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  /3

  $50,000

  • Land
  • 5 Acres
  • $9,823 per Acre

  TBD Deerwood, Greenville, FL 32331

  5.09 wooded acres corner lot, 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 Deerwood, Greenville, FL 32331
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  /9

  $144,000

  • Land
  • 9 Acres
  • $15,352 per Acre

  402 Mistletoe Ln, Monticello, FL 32344

  Escape to tranquility with this expansive piece of raw, rural land for sale. Offering acres of untouched beauty, this property provides the perfect opportunity to build your dream home or start your next project. With no neighbors behind, you'll enjoy complete privacy and seclusion, surrounded only by nature’s peaceful serenity. Whether you're looking for a quiet retreat, hunting grounds, or

  Melissa Montalvo Engel & Volkers Tallahassee

  402 Mistletoe Ln, Monticello, FL 32344
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  /42

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,841 Sq Ft

  952 Turney Anderson Rd, Monticello, FL 32344

  Discover your own private retreat with this charming home set on a fully fenced 10-acre lot. Nestled among mature pecan and fruit trees, this property offers the perfect blend of tranquility, space, and functionality. Enjoy relaxing mornings and evenings on the spacious front and back porches, ideal for soaking in the serene surroundings. The home features a practical layout with a cozy living

  Katherine Hansli Searcy The Naumann Group Real Estate

  952 Turney Anderson Rd, Monticello, FL 32344
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  /11

  $27,500

  • Land
  • 0.52 Acre
  • $52,885 per Acre

  0 E Capps Hwy, Lamont, FL 32336

  For Sale: Buildable Vacant Lot – 0.52 Acres on E Capps Hwy, Lamont, FL 32336.Discover the potential of this 0.52-acre buildable lot with 624.57 feet of road frontage on E Capps Hwy in peaceful Lamont, Florida. With power available at the road, this parcel is ready for your vision—whether you're planning a new home, a weekend retreat, or a smart investment. Zoning: Buildable residential

  Andrey Rossin CASH FLOW IN MIAMI REALTY

  0 E Capps Hwy, Lamont, FL 32336
• 

  

  /36

  $399,000

  • 3 Beds
  • 2 Baths
  • 2,020 Sq Ft

  259 Barnes Rd, Monticello, FL 32344

  Spacious Brick on 4.25 acres. Easy Thomasville commute. Discover peace and privacy with this well maintained brick ranch nestled in the woods. Step into the spacious living room with cozy wood burning fireplace, ideal for relaxing evenings or entertaining. Office, large utility room, 2 car garage, and workshop are some of the extras. Enjoy this quiet private setting.

  Pam Kelly Kelly & Kelly Properties, Inc

  259 Barnes Rd, Monticello, FL 32344

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