Jefferson County FL Homes for Sale

• 

  

  

  /42

  $339,000

  • 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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /31

  $55,000

  • Land
  • 8 Acres
  • $7,152 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
• 

  

  /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
• 

  

  /51

  $349,900

  • Land
  • 44 Acres
  • $7,890 per Acre

  1069 N Salt Rd, Monticello, FL 32344

  44+ Acres - 1069 N Salt Road, Jefferson County, FL Located within 10 miles from downtown Monticello Quick and easy access to I-10 Secluded setting with peace and privacy Cleared homesite featuring a 40x60 pole barn Interior trail system for easy navigation and recreation Excellent deer, turkey, and duck hunting opportunities Multiple game habitats for

  Ben Jones

  1069 N Salt Rd, Monticello, FL 32344
• 

  

  /42

  $489,900

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /28

  $749,000

  • 3 Beds
  • 2 Baths
  • 2,083 Sq Ft

  5301 Gentle Breeze Dr, Tallahassee, FL 32309

  RARE OPPORTUNITY to own lakefront property on the picturesque Lake Miccosukee! Charming cabin is discreetly nestled by the water’s edge, embracing a naturally beautiful 10-acre estate. Property features an inviting home with an expansive family room, complete with a stunning window wall, providing breathtaking views surrounded by nature with abundant local wildlife for hunting or watching. For

  Nancy Treadway Treadway Appraisal & Realty

  5301 Gentle Breeze Dr, Tallahassee, FL 32309
• 

  

  /48

  $525,000

  • 5 Beds
  • 3.5 Baths
  • 4,600 Sq Ft

  885 S Waukeenah St, Monticello, FL 32344

  Tucked into the charming heart of Monticello, yet only a short scenic drive to Tallahassee, this estate bridges the gap between past and present, country and capital, southern soul and worldly sophistication. Step beyond through the historic front door into a moment suspended in time where Southern grandeur, storied legacy, and modern luxury converge in a peaceful retreat just 30 minutes from the

  Jason Boone Keller Williams Town & Country

  885 S Waukeenah St, Monticello, FL 32344
• 

  

  /58

  $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
• 

  

  /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
• 

  

  /43

  $539,000

  • 4 Beds
  • 2.5 Baths
  • 3,054 Sq Ft

  79 Lakeside Rd, Monticello, FL 32344

  Welcome to your country escape — a timeless farmhouse nestled on 3+ scenic acres, offering the perfect blend of space, charm, and opportunity. This classic home features soaring high ceilings, oversized rooms, and a sprawling, screened- in wraparound porch of over 1,000 square feet that invites you to sit back and soak in the peaceful surroundings. Inside, you’ll find large, light-filled living

  Michael Schilling Hill Spooner & Elliott Inc

  79 Lakeside Rd, Monticello, FL 32344
• 

  

  /50

  $499,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,774 Sq Ft

  107 Tarn Way, Monticello, FL 32344

  2024 Custom Built Home with Premium Upgrades in Hemings Pond Subdivision! Better than new - This 3 bedroom/2 Bathroom 2024-build by Nailed It Construction offers luxury vinyl plank floors throughout, upgraded light fixtures, premium countertops, and elegant bath finishes. Both bathrooms feature tastefully muted designer tile-work. Thoughtful owner upgrades include: custom wood plantation shutters

  Brenna Kelly-Ward Kelly & Kelly Properties, Inc

  107 Tarn Way, Monticello, FL 32344
• 

  

  /3

  $499,900 New Construction

  • 4 Beds
  • 3 Baths
  • 1,798 Sq Ft

  855 S Waukeenah St, Monticello, FL 32344

  Stunning New Construction home currently being built by Southern Construction. Centrally located in downtown Monticello, with mature landscaping, and plenty of room for the family. This 4 bed and 3 bath home will feature vinyl plank flooring, granite countertops, walk in tile shower and tub in master, upgraded trim package, and stainless appliances. Some finishes have been selected by builder,

  Jared Parramore Coastwise Realty

  855 S Waukeenah St, Monticello, FL 32344
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /12

  $85,000

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft

  208 Robin Rd, Monticello, FL 32344

  HANDYMAN SPECIAL ON ONE ACRE OFF GOVERNMENT MAINTAINED ROAD WITH TONS OF PEACE AND QUIET! LARGE OAK TREES, COMQUAT, SATSUMA, FIGS AND WHITE GARDENIAS! Fully fenced with gates so you can park all your toys or work equipment! Separate fenced off area in back for your pets. Large shed in back for more storage.

  Kimberly Nabors Advanced Realty Group LLC

  208 Robin Rd, Monticello, FL 32344
• 

  

  /69

  $900,000

  • 5 Beds
  • 4 Baths
  • 4,150 Sq Ft

  860 Tally Hills Dr, Monticello, FL 32344

  Don't miss your chance to own one of the most striking homes in Tally Hills with lake access, acreage, and luxury features that rarely come to market! This gated community features desirable homes on acreage. SO much to offer, ask to see the separate feature list! A remote control gate brings you into the circular driveway. A bubbling water feature leads you to the front entryway. Designed with

  M. Andy Elliott Xcellence Realty

  860 Tally Hills Dr, Monticello, FL 32344
• 

  

  /12

  $99,500

  • Land
  • 5.00 Acres
  • $19,900 per Acre

  489 Ashville Highlands Dr, Greenville, FL 32331

  Come and camp while you are waiting to build. Many improvements on this 5 acre parcel. Partly cleared (approx 2.5 ac), large septic with comnection for RV with macerator pump, 200 amp power service with meter and pole and 30 amp RV connection. High speed internet running through the property. No HOA, freedom to build what you want. Enjoy an abundance of wildlife. Some area is in flood zone see

  Barry Kelly Kelly & Kelly Properties, Inc

  489 Ashville Highlands Dr, Greenville, FL 32331
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /14

  $39,000

  • Land
  • 0.09 Acre
  • $433,333 per Acre

  3C Hanger Ln, Greenville, FL 32331

  Fly in to scenic, rural north Florida, and enjoy all the area has to offer! T-Hangar is located near Monticello, FL at the longest turf runway in Florida (FL74 – 6395ft.). Pour a concrete floor and add an electric line for instant equity. Leave a car or RV in the hangar while you're back home, and take it adventuring once you arrive! 1 hour to the Gulf coast or Tallahassee, 2 hours to

  Esther Warrendorf Canopy Road Realty

  3C Hanger Ln, Greenville, FL 32331
• 

  

  /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
• 

  

  /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

  $230,000

  • Land
  • 40 Acres
  • $5,750 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
• 

  

  /24

  $85,000

  • Land
  • 6 Acres
  • $13,240 per Acre

  Vacant E Washington Hwy, Monticello, FL 32344

  ?? 6.42 Acres For Sale – Fronting US 90! ??? ?? Located less than 10 miles from Downtown Monticello ?? Peaceful, quiet setting just minutes from amenities ?? Well, power, and septic already installed – ready to build! ?? Multiple homesites to choose from ?? No HOA – total freedom to create your dream retreat ?? Excellent hunting potential – deer, turkey & ducks ?? Pond onsite – perfect for

  Ben Jones Southern Land & Homes

  Vacant E Washington Hwy, Monticello, FL 32344
• 

  

  /3

  $45,000

  • Land
  • 2.00 Acres
  • $22,500 per Acre

  33 Kameron Dr, Waukeenah, FL 32344

  I am pleased to announce this beautiful piece of property available for purchase, consisting of 2 acres of raw land situated in the serene rural outskirts of Monticello, Florida. The asking price for this exceptional land is only $45,000. This property is nestled in the picturesque Keystone County of Florida. Jefferson County is renowned for its gently rolling hills, majestic oak trees, and the

  Meka Spencer Keller Williams Town & Country

  33 Kameron Dr, Waukeenah, FL 32344

Showing Results 1 - 40, Page 1 of 3