Jefferson, FL Homes

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  /8

  $3,069,542 Sold May 12, 2025

  • Land
  • 450 Acres
  • $6,821 per Acre

  • 284 Days On Market

  0 Bassett Dairy Rd Unit 373105, Monticello, FL 32344

  450 acres that has been in the family for over 50 years. Beautiful rolling topography of crop lands, pasture and timber. Elevation of 260 ft. above sea level. Water elements to enjoy. Adjacent 420 acres can be purchased for $3,150,000, see listing Number 380760, beautiful 870 acres total

  Brian Proctor NAI TALCOR Commercial

  0 Bassett Dairy Rd Unit 373105, Monticello, FL 32344
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  /30

  Est $529,555 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,016 Sq Ft

  3214 Tram Rd, Monticello, FL 32344

  3214 Tram Rd, Monticello, FL 32344
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  /27

  $399,000

  • 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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  /42

  $900,000 Sold May 08, 2025

  • 2,750 Sq Ft
  • $327/SF
  • 38 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2018

  542 Tradition Way, Monticello, FL 32344

  Stunning 3 BR 2.5 Bath custom pool home offering elegance and comfort. Situated on 7 landscaped and manicured acres, fenced and cross fenced. Meticulously maintained both inside and out. 10 ft ceilings, 8 ft doors, large windows, with upscale finishes throughout. Gourmet kitchen equipped with premium appliances, ample custom cabinets, spacious island with plenty of counters for entertaining.

  Pam Kelly Kelly & Kelly Properties, Inc

  542 Tradition Way, Monticello, FL 32344
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  /28

  Est $381,745 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,328 Sq Ft

  129 Indian Hills Rd, Monticello, FL 32344

  129 Indian Hills Rd, Monticello, FL 32344
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  /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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  /10

  $80,000 Sold May 05, 2025

  • 782 Sq Ft
  • $102/SF
  • 27 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1955

  895 Independent St, Monticello, FL 32344

  Charming cottage, affordable living under $100,000. Small lot for easy maintenance. New split ac unit. New roof, windows, flooring, new insulation in attic, and new appliances. Potential Owner financing $10,000 down, 6% interest, 3 year balloon.

  Barry Kelly Kelly & Kelly Properties, Inc

  895 Independent St, Monticello, FL 32344
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  /38

  Est $154,528 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft

  310 N Olive St, Monticello, FL 32344

  310 N Olive St, Monticello, FL 32344
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  /37

  $398,000

  • 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

  Pam Kelly Kelly & Kelly Properties, Inc

  205 N Rhodes St, Monticello, FL 32344
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  /9

  $43,000 Sold May 02, 2025

  • Land
  • 5 Acres
  • $8,583 per Acre

  • 98 Days On Market

  TBD Ashville Highlands Dr, Greenville, FL 32331

  LAND FOR SALE NEAR MONTICELLO FL. 5.01 Acres. Private building site, hunting, or weekend getaway, this secluded lot is only 15 minutes from charming downtown Monticello and 40 minutes from Eastern Tallahassee. About 70% of this wooded tract consists of high, well drained Troup and Fuquay soils that are excellent for building. Wooded pond in Southeast corner of the lot. The balance is heavily

  Grayson Boyd FL-GA Realty & Auction

  TBD Ashville Highlands Dr, Greenville, FL 32331
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  /36

  Est $654,777 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 5,556 Sq Ft

  250 Hiawatha Farms Rd, Monticello, FL 32344

  250 Hiawatha Farms Rd, Monticello, FL 32344
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  /40

  $389,000

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

  480 W Washington St, Monticello, FL 32344

  OWNERS MOTIVATED-ALL REASONABLE OFFERS WILL BE CONSIDERED.Step Back In Time! Rare chance to own your own piece of "Old Florida". Craftsman Style beauty with soaring 10 ' bead-board ceilings and 10 " baseboards, original pine floors and 4 gas fireplaces. Perfect blend of old Florida charm and modern conveniences. Statuary Marble countertops and copper sink in kitchen, extra large dining room for

  Pam Kelly Kelly & Kelly Properties, Inc

  480 W Washington St, Monticello, FL 32344
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  /42

  $529,900 Sold Apr 30, 2025

  • 1,868 Sq Ft
  • $284/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2017

  273 Legacy Way, Monticello, FL 32344

  Stunning 2017 built home on 3.03 acres with mature trees on all sides for incredible privacy! This home features 3 bedrooms, 2 bathrooms, and a 2-car garage. Gorgeous design finishes include granite counters, stainless appliances, custom cabinets, built-in entertainment center with shiplap accent, craftsman style trim and crown molding, covered back porch with brick paver floor, and stone accents

  Amber Renaud The Nova Group Realty

  273 Legacy Way, Monticello, FL 32344
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  /28

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,323 Sq Ft

  1993 Hartsfield Rd, Monticello, FL 32344

  1993 Hartsfield Rd, 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

  $449,000 Sold Apr 30, 2025

  • 3,635 Sq Ft
  • $124/SF
  • 80 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1842

  340 E Washington St, Monticello, FL 32344

  Step into the timeless elegance of the Simpkins-Bailey House, a distinguished circa 1854 residence nestled in the heart of Monticello's Historic District. This 3-bedroom, 3.5-bathroom home offers 3,635 square feet of meticulously updated living space, seamlessly blending historic charm with modern comforts. Zoned for business-residential use, the property provides incredible flexibility for a

  Sandy Ferrera All County Suncoast Property

  340 E Washington St, Monticello, FL 32344
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  /31

  Est $393,479 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft

  1613 Yaupon Ct, Monticello, FL 32344

  1613 Yaupon Ct, 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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  /41

  $225,000 Sold Apr 30, 2025

  • 1,344 Sq Ft
  • $167/SF
  • 101 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  111 W 8th Ct, Greenville, FL 32331

  Fantastic turnkey 3 bedroom 2 bathroom home on 5 very private acres! 1344sqft of living space with a bright and airy living room and dining room combo that greets you through the front door. Huge beautiful live oaks dot the wooded property. Approximately 1 mile down an easy to drive dirt road to the home. The home has been impeccably maintained and cared for, the roof was replaced about 10 years

  Catherine Hope All Realty Services

  111 W 8th Ct, Greenville, FL 32331
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  /3

  Est $62,000 Not Listed For Sale

  420 N Forest Ct, Monticello, FL 32344

  420 N Forest Ct, 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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  /29

  $60,000 Sold Apr 29, 2025

  • 2,612 Sq Ft
  • $23/SF
  • 52 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1914

  1150 Sage St, Monticello, FL 32344

  Built in 1914, this historic home in the heart of Monticello, Florida, offers a rare opportunity to own a piece of the past. With 5 spacious bedrooms and 2 full bathrooms, this charming property sits on a generous 0.63-acre lot, providing ample outdoor space. While the home requires significant renovation, it boasts original historical elements throughout, including beautiful hardwood floors,

  Gabriela Sacco All Realty Services

  1150 Sage St, Monticello, FL 32344
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  /11

  Not Listed For Sale

  xxx St Augustine Parcel #4 Rd, Monticello, FL 32344

  xxx St Augustine Parcel #4 Rd, 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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  /14

  $230,000 Sold Apr 24, 2025

  • 1,316 Sq Ft
  • $175/SF
  • 26 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1970

  523 Silver Lake Rd, Monticello, FL 32344

  Prime location in NE Jefferson County! Just 5 minutes to historic Monticello with easy travel to Tallahassee, Thomasville and Quitman. Lots of properties boast horse potential, but this 12 acre parcel truly has room for all your equine needs. High and dry with paved roads. Unlock the potential of this home that’s ready for a transformation! While extensive repairs are needed, this property

  Brian Bachman Kelly & Kelly Properties, Inc

  523 Silver Lake Rd, Monticello, FL 32344
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  /17

  Est $262,743 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  188 Fallow Rd, Lamont, FL 32336

  188 Fallow Rd, Lamont, FL 32336
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  /70

  $425,000 Under Contract

  • 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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  /39

  $321,000 Sold Apr 24, 2025

  • 1,680 Sq Ft
  • $191/SF
  • 43 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2022

  1260 E Washington St, Monticello, FL 32344

  Beautiful Modern Home on a Spacious corner Lot. Built in 2022, this stunning 1,680 sq. ft. home offers modern living with an open floor plan, perfect for entertaining. Featuring three bedrooms and two bathrooms, this energy-efficient home boasts a stylish kitchen, a convenient mudroom, and a two-car carport. Located near downtown Monticello, you'll enjoy easy access to the local shops, dining,

  Shanna D'Attile Keller Williams Town & Country

  1260 E Washington St, Monticello, FL 32344
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  /14

  Est $348,261 Not Listed For Sale

  • 2 Beds

  4131 Ashville Hwy, Monticello, FL 32344

  4131 Ashville Hwy, Monticello, FL 32344
• 

  

  /42

  $449,000 Under Contract

  • 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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  /27

  $384,000 Sold Apr 22, 2025

  • Land
  • 25 Acres
  • $15,534 per Acre

  • 812 Days On Market

  162 Natural Bridge Rd, Monticello, FL 32344

  LOCATED ON THE CORNER OF FANLEW ROAD AND NATURAL BRIDGE ROAD IN A LITTLE COMMUNITY CALLED FANLEW. THIS COMMUNITY SERVED SAWMILLS AND TURPENTINE STILLS THAT ONCE POPULATED THIS AREA. IT STRADDLES JEFFERSON WAKULLA AND LEON COUNTY. THE PROPERTY IS A MIXTURE OF PINES AND HARDWOODS AND SPORTS AN ORIGINAL HOMESTEAD, NOT LIVEABLE. THERE IS A MOBILE HOME ON THE PROPERTY WITH WELL, POWER AND SEPTIC. LOTS

  Amy Crain The American Dream

  162 Natural Bridge Rd, Monticello, FL 32344
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  /38

  Est $202,416 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,276 Sq Ft

  5118 E Washington Hwy, Monticello, FL 32344

  5118 E Washington Hwy, Monticello, FL 32344
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  /40

  $419,900 Under Contract

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

  115 Crooked Creek Ln, Monticello, FL 32344

  New 2025 Built Home 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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  /41

  $220,000 Sold Apr 21, 2025

  • 1,247 Sq Ft
  • $176/SF
  • 73 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2004

  370 Brown Rd, Lamont, FL 32336

  Amazing 3 bedroom 2 bathroom home, with huge bonus room, on one acre with a picturesque pecan tree lined driveway! This home is ready to move into today, with a brand new roof (Dec 2024) and other recent updates including water heater (2022), and kitchen and bathroom faucet fixtures. Kitchen has a bar that opens to the large living room which lets in tons of natural light. The front yard is

  Catherine Hope All Realty Services

  370 Brown Rd, Lamont, FL 32336
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  /5

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,128 Sq Ft

  271 Tecumseh Rd, Monticello, FL 32344

  271 Tecumseh Rd, Monticello, FL 32344
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  /42

  $459,000 Under Contract

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

  4287 Bassett Dairy Rd, Monticello, FL 32344

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

  Destiny Jones Keller Williams Town & Country

  4287 Bassett Dairy Rd, Monticello, FL 32344
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  /27

  $399,900 Sold Apr 21, 2025

  • 1,601 Sq Ft
  • $250/SF
  • 129 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  81 Coopers Pond Rd, Monticello, FL 32344

  New build, under construction! Completion date set for April 2025. Beautiful, private lot on 2.62 acres, close to downtown Monticello and no HOA!! 5 mins to I-10 and 4 mins to US90 - - > see similar new build, under construction @ 149 Coopers Pond on 1.05 acres @ $349,900. Highlights of builder specs are as followed: - 1601sqft - 3 bedrooms - 2 full baths - 10' tray ceiling in living room - LVP

  Tiffany Kasdorf The Nova Group Realty

  81 Coopers Pond Rd, Monticello, FL 32344
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  /16

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,801 Sq Ft

  157 White Oak Dr, Monticello, FL 32344

  157 White Oak Dr, Monticello, FL 32344
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  /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
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  /18

  $2,000,000 Sold Apr 21, 2025

  • Land
  • 765 Acres
  • $2,614 per Acre

  • 182 Days On Market

  1268 NW White Wing Dove Dr, Greenville, FL 32331

  AA Ranch is a turn-key, 765 acre hunters paradise. Looking to bag that monster buck or just get away from the world, this is the perfect property. Teaming with deer, turkey, hogs, ducks, gators and more. There are 8 established food plots with battery powered feeders, two dug ponds 2, and approximately 5 miles of well maintained roads. The property features a 2400sq ft, 2 BR 2 BA custom

  Buddy Witmer Steve C. Walker Realty, LLC

  1268 NW White Wing Dove Dr, Greenville, FL 32331

Showing Results 81 - 120, Page 3 of 18