Jefferson County FL Homes for Sale

• 

  

  

  /28

  $397,000

  • 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

  (448) 327-5761

  1205 E Pearl St, Monticello, FL 32344
• 

  

  

  /51

  $425,000

  • 3 Beds
  • 2.5 Baths
  • 3,127 Sq Ft

  1628 N Jefferson Hwy, Monticello, FL 32344

  Picturesque, 4/2, brick beauty with a whimsical style that evokes the charm of a traditional storybook estate, with 3,217 sq. ft., bordering a large acreage holding on 2 sides. Beautiful attributes from the 1955 era such as cedar lined closet, crystal door knobs, original oak floors, wide baseboards, double bay windows, 24x10 screened porch and entertainment deck. Lifetime metal Roof! Boasting

  

  Lynette Sirmon

  All Realty Services

  (448) 288-6919

  1628 N Jefferson Hwy, Monticello, FL 32344
• 

  

  

  /28

  $545,000

  • 3 Beds
  • 2 Baths
  • 1,810 Sq Ft

  512 Creekside Ct, Monticello, FL 32344

  Like New!Barely lived in 2020 Home in sought-after Crooked Creek Subdivision! Whole home Generac generator, fenced in backyard, screened in back porch along with all the interior upgrades! Easy commute to Thomasville and Tallahassee with the small-town charm of Monticello! This beautiful 3/2 is on a spacious cul-de-sac lot that backs up to the HOA-owned conservation property with a pond. This

  

  Chance Shutes

  Keller Williams Town & Country

  (448) 218-5546

  512 Creekside Ct, Monticello, FL 32344
• 

  

  

  /57

  $699,000

  • 6 Beds
  • 3.5 Baths
  • 3,114 Sq Ft

  365 S Mulberry St, Monticello, FL 32344

  Historic soul. Modern substance. A rare circa-late 1800s home, beautifully restored and thoughtfully made NEW. Some houses simply endure... and some are given the rare chance to begin again. Better than New Construction! Just two blocks from the courthouse square in Monticello, Fl, this circa-late 1800s home—a classic Southern I-house shaped by Greek Revival influence—once stood quietly

  Lee Hall Capital City Real Estate Group

  365 S Mulberry St, Monticello, FL 32344
• 

  

  

  /19

  $299,000

  • Land
  • 70.45 Acres
  • $4,244 per Acre

  265 Neely Rd, Monticello, FL 32344

  Secluded, but not remote, this 70.45 acre tract in eastern Jefferson County, Florida would make an ideal hunting getaway property or a rural homesite. Virtually no ambient noise or light that will disturb the quiet woods. About half the tract is in 7-year-old planted loblolly pines and the rest is in natural woods and cypress ponds. You will be smack in the middle of some of the best deer and

  Dave Lewis Southern Forestry Realty

  265 Neely Rd, Monticello, FL 32344
• 

  

  /16

  $487,878

  • Land
  • 122 Acres
  • $3,999 per Acre

  0 James Noble Rd, Greenville, FL 32331

  Millwood Timberland East is a balanced property located in a great recreational market. The Ashville area is home to numerous trophy grade recreational properties and is known for exceptional whitetail, turkey and waterfowl hunting. This property features an efficient footprint with good access and internal road infrastructure. The uplands are planted with slash pine that are approximately 8

  Bryant Peace Saunders Real Estate

  0 James Noble Rd, Greenville, FL 32331
• 

  

  /8

  $450,000

  • Land
  • 85.26 Acres
  • $5,278 per Acre

  1899 Big Joe Rd, Monticello, FL 32344

  Known for its white tail deer, hog and turkey populations, this 85.26 acres in Jefferson County, FL would make a perfect hunting camp. Pristine pine tree property just minutes from Interstate 10 / Exit 225. Ideal Country Estate or weekend get-away. Seller financing available to qualified buyer.

  Tom Woodyard Woodyard & Associates, LLC

  1899 Big Joe Rd, Monticello, FL 32344
• 

  

  /49

  $615,000

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

  3873 N Jefferson Hwy, Monticello, FL 32344

  Stunning 4 Bedroom, 5 Bath Home on 9.73 Acres with Large Detached Garage plus Oversized Attached 2 Car GarageLocated just north of Monticello, 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 is not located in a flood zone or HOA. Built in 2007, the home features

  Stephanie Fox Mossy Oak Properties Southern Land and Homes, LLC

  3873 N Jefferson Hwy, 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
• 

  

  /42

  $447,500

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

  75 E 5th Ct, Greenville, FL 32331

  "Fly-in" living at its finest! Located on 5 acres featuring a main residence, a guest house, an impressive 60x48 aircraft hangar + 40x48 apron with direct access to a 6,000 foot grass airstrip. Land then taxi directly to your 2 homes, hangar and fly out with ease. The two homes total sq. ft. equals 2,499 sq. ft. (one is 1152 sq. ft. and the other one is 1347 sq. ft). Located on a total of FIVE

  Brenda Aaron WIP Realty

  75 E 5th Ct, Greenville, FL 32331
• 

  

  /57

  $599,000

  • 7 Beds
  • 7 Baths
  • 5,139 Sq Ft

  625 E Washington St, Monticello, FL 32344

  Introducing a stunning 1.2 acre estate in the heart of Historic Downtown Monticello. The Simon-Ridgeway home was built in 1888 and boasts a generous 4,500 sq ft of living space and features 7 spacious bedrooms, 5 of which come with its own en-suite bathroom for ultimate privacy and convenience. City granted BNB status - making this perfect for an owner/occupier wanting to work from home and enjoy

  625 E Washington St, Monticello, FL 32344
• 

  /2

  $470,000 Open Sun 12PM - 5PM

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  51 Tarn Way, Monticello, FL 32344

  **Photos Coming Soon! Home will be move in ready May 20th. Amazing new construction 3 bedroom 2 bathroom plus office. Luxurious master suite, Kitchen made of dreams, this is a must see!

  Amber McKinney Hamilton Realty Advisors LLC

  51 Tarn Way, Monticello, FL 32344
• 

  

  /66

  $399,000

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

  1012 S Main Ave, Monticello, FL 32344

  Tucked away on 5 private acres down a quiet, wooded road, this brick home offers 2,280 square feet with a split floor plan featuring 3 bedrooms and 2 baths, providing both space and functionality. New Roof November 2025, Well 2022, and septic drain field replaced 2016. Inside, you’ll find a cozy fireplace and a bright sunroom that brings the outdoors in, while the solid layout offers plenty of

  Robert Donovan Tallahassee Board of REALTORS®

  1012 S Main Ave, Monticello, FL 32344
• 

  

  /43

  $489,000

  • 4 Beds
  • 2 Baths
  • 1,864 Sq Ft

  4235 N Jefferson St, Monticello, FL 32344

  Shows like new and impeccably maintained, this beautiful brick home sits on 5.14 acres tucked away in a serene pine forest, offering both tranquility and convenience with an ease commute to Thomasville, GA and Monticello, Fl. This spacious 4-bedroom home features a thoughtfully designed layout, including a large screened back porch perfect for relaxing or entertaining while enjoying the peaceful

  4235 N Jefferson St, Monticello, FL 32344
• 

  

  /38

  $449,900

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

  107 S Tarn Way, Monticello, FL 32344

  Welcome to this beautifully custom-built 3 bedroom, 2 bath home completed in 2024 and located in the desirable Hemings Pond Subdivision. Offering the perfect blend of modern construction and thoughtful upgrades, this move-in ready showcases luxury vinyl plank flooring, upgraded light fixtures, premium countertops, and elegant bath fixtures. Owner selected custom enhancements elevate the space

  107 S Tarn Way, Monticello, FL 32344
• 

  

  /31

  $434,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  285 Mallard Ln, Monticello, FL 32344

  *Jefferson County peaceful country living with a waterfront backdrop! Built in 2008, this well maintained 3 bedroom, 2 bath home sits on 4.89 beautifully (mostly cleared) acres offering privacy and natural beauty backing directly up to Lloyd Lake- perfect for relaxing evenings with scenic views. Pretty rocking chair front porch as well as a screened in back porch with a propane hookup for

  285 Mallard Ln, Monticello, FL 32344
• 

  

  /70

  $795,000

  • 3 Beds
  • 2.5 Baths
  • 2,160 Sq Ft

  660 Whispering Hill, Monticello, FL 32344

  Set on 18+ acres of beautifully maintained pasture, this private country property is built for both everyday living, true equestrian use or small livestock farm. The land is the star- fully fenced with new wood fencing that cleanly defines multiple pastures, a peaceful pond, and wide open space to ride, graze and enjoy. The 6-stall horse barn is ready to work with paddocks attached to each stall,

  Catherine Hope All Realty Services

  660 Whispering Hill, Monticello, FL 32344
• 

  

  /31

  $625,000

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

  140 Shumard Ct, Monticello, FL 32344

  Discover this stunning 2,600+ sqft home built in 2021, offering the perfect blend of quiet country living and modern convenience. Features include: 4 spacious bedrooms and 3 full bathrooms 2 master bedrooms located downstairs Dedicated office/bonus room – ideal for work or hobbies Modern kitchen and open living spaces Attached 2-car garage Just minutes from downtown, providing a quick and easy

  140 Shumard Ct, Monticello, FL 32344
• 

  

  /60

  $550,000

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft

  925 Hiawatha Farms Rd, Monticello, FL 32344

  (One or more photos has been virtually staged) Custom hurricane-resistant/efficiency home on 3.6 private acres in a gated equestrian community, just 17 miles east of Tallahassee and 1 mile to I-10 (Exit 217). Built in 2013, this 2,112 sq ft home features 4 bedrooms, 3 full baths, and 9’ ceilings throughout. Constructed with Nudura ICF 12” insulated concrete exterior walls for superior strength,

  DONALD DANIELS Spirit Realty Inc. Of Tallahas

  925 Hiawatha Farms Rd, Monticello, FL 32344
• 

  

  /19

  $470,000 New Construction

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

  855 S Waukeenah St, Monticello, FL 32344

  Stunning New Construction recently 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 features vinyl plank flooring, granite countertops, walk in tile shower and tub in master, upgraded trim package, and stainless appliances. Nice large back porch with deck, over looking the large

  855 S Waukeenah St, Monticello, FL 32344
• 

  

  /3

  $775,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,377 Sq Ft

  693 Tally Hills Dr, Monticello, FL 32344

  New Construction. Images are renderings. 4-bedroom, 3-bath home coming soon in Tally Hills Estates. Construction has started on this beautifully designed, new construction home set on over 5 acres.

  Marlinda Bullock KILLEARN SALES CENTER,

  693 Tally Hills Dr, Monticello, FL 32344
• 

  

  /67

  $399,900

  • 4 Beds
  • 2 Baths
  • 2,314 Sq Ft

  701 Barber Hill, Lamont, FL 32336

  (One or more photos has been virtually staged) Just reduced! Welcome to a classic country farmhouse set on 19.21 picturesque acres, offering the space, infrastructure, and versatility today’s buyers are seeking. From the aerial view, the property unfolds as a true working farm with fenced and cross-fenced pastures, mature trees, and a thoughtfully laid-out compound of multiple outbuildings,

  DONALD DANIELS Spirit Realty Inc. Of Tallahas

  701 Barber Hill, Lamont, FL 32336
• 

  

  /52

  $425,000

  • 4 Beds
  • 3 Baths
  • 3,188 Sq Ft

  930 E Pearl St, Monticello, FL 32344

  Built between 1890-1910, this Classic Revival home sits on 1.77 acres along one of Monticello’s most admired streets and offers timeless architecture with room to make it your own. The two-story layout includes 4 bedrooms and 3 bathrooms, with a circular driveway framed by boxwoods leading to a wide front porch perfect for rocking chairs. Inside, two front parlors flank the entry—one used as a

  Robert Donovan Tallahassee Board of REALTORS®

  930 E Pearl St, Monticello, FL 32344
• 

  

  /70

  $410,000

  • 3 Beds
  • 2 Baths
  • 1,891 Sq Ft

  1637 N Jefferson Hwy, Monticello, FL 32344

  Awesome all brick 3 bedroom 2 bathroom home on 4 beautiful acres along North Jefferson Highway in Jefferson County, FL. Hardwood floors run throughout with tile in the kitchen and bathrooms. The kitchen offers solid wood cabinetry with soft-close drawers, updated appliances, and ample storage. Mature longleaf pines dot the property, which features a circular driveway and a 24x24 concrete pad with

  Robert Donovan Tallahassee Board of REALTORS®

  1637 N Jefferson Hwy, Monticello, FL 32344
• 

  

  /46

  $450,000

  • 3 Beds
  • 2 Baths
  • 2,239 Sq Ft

  254 Woodland Dr, Monticello, FL 32344

  Custom home on 4.29 private acres~split bedroom plan~separate dining room~rocking chair front porch~screened porch overlooking wooded backyard~fireplace~upstairs room could be office or playroom~huge 40x40 workshop~FIRST TIME ON THE MARKET

  254 Woodland Dr, Monticello, FL 32344
• 

  

  /32

  $415,000

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

  3827 N Jefferson St, Monticello, FL 32344

  PRICED TO SELL AND READY FOR A QUICK CLOSING! Situated on 5 acres with private pond, this 3 bedroom 3 bath offers over 3000 sf of potential in a highly convenient location just minutes from Thomasville Ga and Monticello Fl. The home features a spacious primary suite, dedicated office, formal living and dining rooms, and a den with fireplace, plus a sun porch overlooking the peaceful acreage. With

  3827 N Jefferson St, Monticello, FL 32344
• 

  

  /19

  $157,000

  • Land
  • 10.54 Acres
  • $14,896 per Acre

  XX Ridge Rd, Monticello, FL 32344

  Leave Urbana and breathe... 10.54 acres in Exclusive Casa Bianca Ridge. Beautiful, rare lot on which to build your dream home. There is room to create a multi-generational paradise or your own personal playground. Nicely wooded parcel with a gentle stream deeper into the property. Very private. Survey in associated docs. Move quickly. Gate at Driveway. Do not enter the property without approval.

  Johanna Money The Williams Group

  XX Ridge Rd, Monticello, FL 32344
• 

  

  /11

  $45,000

  • Land
  • 2.5 Acres
  • $18,000 per Acre

  1 W Meadow Rd, Monticello, FL 32344

  2.5 Acres of land, partially cleared for home-site. Private quiet road. All high and dry ready to build your homestead. mobile homes okay. Close to aucilla river. Convenient to Monticello, FL and Thomasville Ga. Valdosta and Tallahassee 45 minutes away. Horse Friendly area. Owner financing options available.

  1 W Meadow Rd, Monticello, FL 32344
• 

  

  /23

  $325,000

  • 5 Beds
  • 2 Baths
  • 2,659 Sq Ft

  2664 W Washington Hwy, Monticello, FL 32344

  FULLY RENOVATED SPACIOUS HOUSE, 1.3 acres, on picturesque US 90 near Monticello. This move-in-ready home in good condition is a 1950’s era brick ranch-style home with new plumbing, new electric, fresh paint, new roof, and a whole home generator. The main living area is 2,659 sf with a unique two levels. 5 bedrooms and 2 baths with plenty of character, including the "Captain's Room" with built-in

  2664 W Washington Hwy, Monticello, FL 32344
• 

  

  /7

  $135,000

  • Land
  • 10 Acres
  • $13,500 per Acre

  576 Cox Rd, Monticello, FL 32344

  Looking for privacy, this 10 acres provides an ideal homesite with some clearing for your homesite completed. The balance of the land is woorded with a mix of hardwoords and pines. Some of the land is in welands/flood which provides a nice buffer for privacy and a wildlife habitat. There is a well/pump (no tank), an older septic, and power pole. 15 ft easement leads to the property. Located just

  576 Cox Rd, Monticello, FL 32344
• 

  

  /25

  $179,000

  • Land
  • 14.9 Acres
  • $12,013 per Acre

  Lot 8 Sneads Dr, Greenville, FL 32331

  Discover 14.9 acres of pristine residential/recreational land along the Upper Aucilla River, near Sneads Lake in Jefferson County, Florida. This unique property offers a rare combination of upland and waterfront ownership with a portion of the property submerged by the flowing river. "Own out into & beyond the river channel (all the way to other bank) on the "Aucilla River". Outdoor enthusiasts

  Brenda Aaron WIP Realty

  Lot 8 Sneads Dr, Greenville, FL 32331
• 

  

  /4

  $125,000

  • Land
  • 5.05 Acres
  • $24,752 per Acre

  455 E Duck Pond Dr, Greenville, FL 32331

  This natual beauty of 5 acres with house and shed is priced for land value. The delapidated structures holds little to no value. With ownership afar, the property has been untouched for years. Hinting at what once was and what could be again, this property invites a lifestyle of peace and seclusion giving you a unique opportunity to create your own sanctuary complete with a pond that mirrors the

  455 E Duck Pond Dr, Greenville, FL 32331
• 

  

  /61

  $989,000

  • 3 Beds
  • 2.5 Baths
  • 2,280 Sq Ft

  9901 Gamble Rd, Monticello, FL 32344

  A LAND REMEMBERED-Discover a rare opportunity to own over 40 acres of land where conservation and nature meet comfort and privacy. Scenic walking trails wind throughout the property, creating a peaceful retreat for nature lovers. The home features major upgrades, including a new roof, Pella double-paned energy-efficient windows, and a new water heater. Inside, enjoy 9 foot ceilings throughout the

  9901 Gamble Rd, Monticello, FL 32344
• 

  

  /30

  $185,000

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft

  28 Kameron Dr, Monticello, FL 32344

  Brand New Inside! 1-Acre Modern Retreat Just Minutes from the City. Enjoy the ultimate "new home" experience without the wait! This 2-bedroom, 1-bathroom gem at 28 Kameron Dr has been completely transformed with a brand new interior, offering high-end laminate flooring, fresh paint, and modern finishes throughout. Situated on a sprawling, level 1-acre lot, you’ll enjoy total privacy and room to

  28 Kameron Dr, Monticello, FL 32344
• 

  

  /37

  $345,000

  • 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

  205 N Rhodes St, Monticello, FL 32344
• 

  

  /22

  $95,000

  • 3 Beds
  • 2 Baths
  • 1,125 Sq Ft

  295 W J Hatchett Rd, Lamont, FL 32336

  Investor special with great potential! Situated on approximately .75 acres in Jefferson County, this 2022 mobile home offers a fantastic opportunity for the right buyer to complete the final steps and make it their own. Conveniently located just minutes from I-10 for easy access to Tallahassee and only about 10 minutes to downtown Monticello, the property combines rural space with excellent

  Robert Donovan Tallahassee Board of REALTORS®

  295 W J Hatchett Rd, Lamont, FL 32336
• 

  

  /54

  $135,000

  • 2 Beds
  • 2 Baths
  • 1,792 Sq Ft

  12447 Gamble Rd, Monticello, FL 32344

  Seller Ready to Not be the Owner Anymore! Corner Lot! This 2 bedroom (could be a 3rd Bdrm however the 3rd bedroom does not have a closet but most 1930's homes did not have closets), 2 bathroom home offers 1,792 sq ft of living on 1 acre in Wacissa, Florida, just 1 minute from the Wacissa River headwaters (first magnitude Spring) and boat launch in Monticello, Jefferson County, Florida. It’s an

  Robert Donovan Tallahassee Board of REALTORS®

  12447 Gamble Rd, Monticello, FL 32344
• 

  

  /70

  $2,000,000

  • 7 Beds
  • 7 Baths
  • 5,756 Sq Ft

  305 Old Lloyd Rd, Monticello, FL 32344

  Welcome to a rare opportunity to own a true estate property where space, craftsmanship, and privacy come together on 18 beautiful acres. This impressive 7-bedroom, 5 full bath, 2 half bath two-story home offers a thoughtfully designed layout ideal for both everyday living and entertaining on a grand scale. Upstairs features 4 bedrooms and 2 full baths, while the downstairs includes 2 bedrooms,

  305 Old Lloyd Rd, Monticello, FL 32344
• 

  

  /24

  $174,900

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  963 Quail Ln, Monticello, FL 32344

  Great location for this property in Lloyd Acres. The property has 2.26 acres of partially wooded area. The property consists of the single family home, detached garage/carport/workshop and a singlewide mobile home. The vinyl sided home will need some repair and updating but has tremendous potential. The detached garage is large with 2 stalls. The mobile home is in need of a total renovation (or

  JAMES L. WILLIAMS MAMIE HURST, REALTOR

  963 Quail Ln, Monticello, FL 32344
• 

  

  /8

  $69,000

  • Land
  • 10.2 Acres
  • $6,765 per Acre

  tbd E 2nd Way, Greenville, FL 32331

  10.2 acre wooded wonderland, corner acreage fronting on 3 roads. Will sell as 2 - 5 acre parcels for $39,500 for each parcel.

  tbd E 2nd Way, Greenville, FL 32331

Showing Results 1 - 40, Page 1 of 3