Jefferson County FL Homes for Sale

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  $345,000

  • 4 Beds
  • 2 Baths
  • 1,551 Sq Ft

  580 Holly Rd, Monticello, FL 32344

  Looking for that small town life but still wanting to be close to Tallahassee? This is it! The quiet neighborhood of Crooked Creek subdivision could be the place for you! Located just outside of Monticello, FL. this roomy 4 bedroom, 2 bathroom 2012 built house has it all. Beautifully land scaped yard with two gazebos and a greenhouse. Vaulted ceilings in the main living area and large over sized

  

  Anthony Gifford

  Ketcham Realty Group, Inc.

  (850) 616-7294

  580 Holly Rd, Monticello, FL 32344
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  /42

  $359,000

  • 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
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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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  /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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  /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
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  /20

  $570,000

  • Land
  • 71 Acres
  • $8,028 per Acre

  0 Aucilla Rd Unit 22696476, Monticello, FL 32344

  Located on Aucilla Rd in Monticello, FL, this versatile AG-5 property offers endless potential for residential, agricultural, and recreational use. The upland portion has been cleared, making it ideal for a homesite or multiple residences, with zoning allowing one unit per five acres and options for family transfers under county guidelines.For those looking to enjoy North Floridas natural

  Jeremiah Thompson Saunders Land

  0 Aucilla Rd Unit 22696476, Monticello, FL 32344
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  /3

  $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
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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

  $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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  /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 Counts Real Estate Group Inc

  133 Devane Rd, Monticello, FL 32344
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  /38

  $675,000 Open Sat 11AM - 2PM

  • 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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  /36

  $435,000

  • 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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  /38

  $424,900

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

  115 Crooked Creek Ln, Monticello, FL 32344

  New Construction in Crooked Creek on a spacious .72 acre lot! This open plan features 4 bedrooms, 2 bathrooms, 2 car garage, and beautiful shiplap accent walls. The kitchen has a light and bright design with white cabinets, quartz counters, subway tile backsplash, and GE stainless appliances. LVP flooring throughout (tile in baths), fireplace, covered back patio, and pre-wired for security and

  Amber Renaud The Nova Group Realty

  115 Crooked Creek Ln, 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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  /34

  $650,000

  • 5 Beds
  • 5 Baths
  • 3,770 Sq Ft

  974 Hiawatha Farms Rd, Monticello, FL 32344

  OPEN HOUSE 2-4pm Saturday, May 17th & 2-4pm Sunday May 18th! Perfect blend of comfort and flexibility on this beautiful, horse-friendly property spanning over 6 acres. The main home offers 3 bedrooms and 3 full bathrooms, featuring a spacious layout designed for everyday living and effortless entertaining. Just steps away, a detached 2-bedroom, 2-bath in-law suite provides the ideal setup for

  Kayana Gaines Hill Spooner & Elliott Inc

  974 Hiawatha Farms 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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  /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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  /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

  $599,900

  • 4 Beds
  • 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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  /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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  /24

  $430,000 New Construction

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

  173 Deerfield Ln, Monticello, FL 32344

  PHOTOS COMING SOON! 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

  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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  /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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  /6

  $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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  /38

  $312,500

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  Unlisted Address

  Private Hunting Retreat on 20 Secluded Acres Just 25 minutes from Florida's Gulf Coast! Escape to your own slice of paradise with this private ,fully-equipped 20 acre property- ideal for hunters, or anyone seeking peace and privacy! Tucked away and surrounded by nature, this property offers the ultimate getaway with hunt-on-your-own-land freedom and thoughtful amenities designed for outdoor

  Pam Kelly Kelly & Kelly Properties, Inc

  Unlisted Address
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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 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 area,

  Katherine Hansli Searcy The Naumann Group Real Estate

  952 Turney Anderson Rd, Monticello, FL 32344
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  /11

  $34,000

  • Land
  • 0.52 Acre
  • $65,385 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 lot.

  Andrey Rossin CASH FLOW IN MIAMI REALTY

  0 E Capps Hwy, Lamont, FL 32336
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  /20

  $400,000

  • Land
  • 31 Acres
  • $12,812 per Acre

  Lot 5 Watermill Rd, Monticello, FL 32344

  Absolutely beautiful, 30 acre lot in Jefferson County! This gorgeous piece of heaven is mostly plantation cut with established hardwoods and just waiting for your dream home! The property is high and dry, with a sweet little sandy bottom creek in the back of the property, and conveniently located, with easy access to I-10 and 27, making it a quick trip to Tallahassee or Monticello. Road access

  Sarah McKinzie Hum Real Estate

  Lot 5 Watermill Rd, Monticello, FL 32344
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  /5

  $65,000

  • 4 Beds
  • 1 Bath
  • 1,232 Sq Ft

  4618 E Capps Hwy, Lamont, FL 32336

  Fixer upper on 1 acre of land. Needs lots of work. Well and septic tank on property. Would need to check to make sure they are good working order.

  Nelda Parker-Pace Sawgrass Realty, LLC

  4618 E Capps Hwy, Lamont, FL 32336
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  /42

  $1,599,000

  • 5 Beds
  • 4.5 Baths
  • 5,476 Sq Ft

  221 Kiley Dr, Monticello, FL 32344

  Welcome to a rare and exquisite, turn-key, 15-acre modern luxury estate, where timeless elegance meets Southern charm. Custom built by Riley Palmer, this exclusive, gated property is nestled just minutes from Tallahassee, Florida's Capital City, and Thomasville, GA in Monticello-home to a storied opera house and chic dining options-and offers the perfect blend of privacy, prestige and proximity.

  Barbra Engel & Volkers Tallahassee

  221 Kiley Dr, Monticello, FL 32344
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  /42

  $1,200,000

  • 5 Beds
  • 5.5 Baths
  • 4,700 Sq Ft

  1165 Dills Rd, Monticello, FL 32344

  Nature Lover’s Dream – Custom Estate on 21+ Acres. Escape to peace and privacy in this stunning custom-built home surrounded by over 21 acres of natural beauty. Thoughtfully designed with both comfort and function in mind, this spacious estate features a gourmet kitchen with gas stove and butler’s pantry, formal and casual living spaces, a cozy library, and a luxurious primary suite with porch

  Callie Rhoads The Naumann Group Real Estate

  1165 Dills Rd, Monticello, FL 32344
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  /42

  $265,000

  • 3 Beds
  • 2 Baths
  • 2,390 Sq Ft

  2436 N Jefferson Hwy, Monticello, FL 32344

  Discover the perfect blend of rustic charm and opportunity with this unique country property. Nestled on 3+ acres, this older farm house offers character and room to grow. The main home features spacious living areas with wood floors throughout and plenty of potential for updates to make it your own. Front screen porch and large utility room. Also included is a second block home. Additional

  Pam Kelly Kelly & Kelly Properties, Inc

  2436 N Jefferson Hwy, Monticello, FL 32344
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  /3

  $150,000

  • Land
  • 11 Acres
  • $14,045 per Acre

  Vacant N Jefferson St, Monticello, FL 32344

  Tucked away just off North Jefferson Highway, this beautiful 10.68-acre parcel offers a quiet setting with plenty of potential. Located just 2.5 miles from the Georgia border, it's an easy 20-minute drive to downtown Thomasville and only 8 minutes to Monticello. The land is fully wooded with a mix of mature oaks and pines. Approximately 75% is high and dry—perfect for building, clearing a

  Catherine Hope All Realty Services

  Vacant N Jefferson St, Monticello, FL 32344
• 

  

  /19

  $299,000

  • 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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