Homes for Sale in 32344

• 

  

  

  /4

  $299,000

  • Land
  • 85.69 Acres
  • $3,489 per Acre

  0 Big Joe Rd Unit 399642, Monticello, FL 32344

  Exceptional opportunity to own 85.69 acres of land located on Big Joe Road in Monticello. Zoned Agri-05, this versatile property offers a unique blend of privacy, natural beauty, and development potential. Featuring a mix of wetlands and usable upland areas, the property may be ideal for a variety of uses including recreational development, camping, hunting retreat, RV park, event venue, outdoor

  Lynnaye Boyd Resilience Realty

  0 Big Joe Rd Unit 399642, 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
• 

  

  

  /6

  $20,999

  • 2 Beds
  • 2 Baths

  10 S Front Ct, Monticello, FL 32344

  TAKE ADVANTAGE OF OUR MEMORIAL DAY MEGA MOVE-IN EVENT! If you purchase this home, receive 2 months FREE site rent and NO application fees. Offer expires May 31, 2026. Act fast! Restrictions apply. A beautifully refurbished home is coming soon-and it's definitely one to keep an eye on. Renovations are currently underway with an estimated completion date of 5/31 (subject to change), bringing fresh

  Patty Davis Jefferson Pines

  10 S Front Ct, Monticello, FL 32344
• 

  

  

  /17

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,502 Sq Ft

  406 Robin Rd, Monticello, FL 32344

  This charming 3-bedroom, 2-bath residence offers spacious living with vaulted ceilings, all nestled on five acres of private land. The property features a new roof for peace of mind, and the large deck is perfect for outdoor entertaining.This home also has a large unfinished basement to fit many of needs. The acreage is divided into 4 lots, providing plenty of space and potential. Located on a

  406 Robin Rd, 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
• 

  /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
• 

  

  /12

  $185,000

  • 3 Beds
  • 1 Bath
  • 1,312 Sq Ft

  670 Poplar St, Monticello, FL 32344

  Solid 3/1 SFR brick less than a mile from downtown Monticello! This quaint 1,312 sq ft home sits under a metal roof and only requires your vision and a little TLC to become a superb starter home or investment opportunity. It also includes an additional lot.

  Spencer Conner Keller Williams Town & Country

  670 Poplar St, Monticello, FL 32344
• 

  

  /27

  $227,900

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

  120 Larry's Ln, Monticello, FL 32344

  Recently renovated home on large lot out in the country. Quiet living at it's best only a couple miles from I-10. Metal roof, new carpet and LVP flooring, fresh paint and fixtures. Home is in great shape and move in ready.

  Randy Kamenicky Mainstreet Realty Of Tallahass

  120 Larry's Ln, 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
• 

  

  /31

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  1164 Oaklands Plantation Rd, Monticello, FL 32344

  Nestled on 5.5 peaceful, private acres, this charming 3-bedroom, 2-bath home offers the perfect blend of space, comfort, and tranquility. Step inside to an open floor plan designed for both everyday living and effortless entertaining, with a seamless flow between the living, dining, and kitchen areas. The spacious primary suite is a true retreat, featuring a large en-suite bathroom complete with

  Cole Davis The Naumann Group Real Estate

  1164 Oaklands Plantation Rd, Monticello, FL 32344
• 

  

  /5

  $199,000

  • Land
  • 5.03 Acres
  • $39,563 per Acre

  TBD W Washington, Monticello, FL 32344

  Fronting on Hwy-90 this high elevation lot is lightly wooded. Some restrictions apply.

  TBD W Washington, 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
• 

  

  /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
• 

  

  /12

  $128,900

  • Land
  • 6.86 Acres
  • $18,790 per Acre

  1407 S Jefferson St, Monticello, FL 32344

  This property presents a strong commercial opportunity along the highly visible Hwy 19 corridor. The property consists of approximately 6.8± acres of B-2 Highway Commercial land with over 400± feet of frontage on Highway 19, offering excellent exposure and accessibility in a growing retail and service trade area.The site includes an approved development plan; however, the only designated

  1407 S Jefferson St, 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
• 

  

  /70

  $2,785,850

  • 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 70 beautiful acres. Only 15 minutes to Whole foods & trader Joe's 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

  305 Old Lloyd Rd, Monticello, FL 32344
• 

  

  /9

  $198,000

  • 3 Beds
  • 1 Bath
  • 1,366 Sq Ft

  870 Shady Ln, Monticello, FL 32344

  Welcome to 870 Shady Lane in Monticello, Florida—a charming property that offers the perfect blend of privacy, space, and small-town appeal. Nestled on a quiet, tree-lined street, this home provides a peaceful retreat while still being conveniently close to the historic downtown district, local shops, and dining. Surrounded by mature trees and natural beauty, the property offers a serene setting

  Angela Graham Hamilton Realty Advisors LLC

  870 Shady Ln, 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
• 

  

  /6

  $462,000

  • Land
  • 58.46 Acres
  • $7,903 per Acre

  1310 Piney Woods Rd, Monticello, FL 32344

  No sign on property, Must be accompanied. Nature and tree lover, timber value on the property, many great homesite locations. Pines and hardwoods, Power easement on the property. Community water and high speed internet through Tri County Electric. 3 separate parcel ID 3#s 03-1N-4E-0000-001F-0000, 03-1-4E-0000-001E-0000

  1310 Piney Woods Rd, Monticello, FL 32344
• 

  

  /8

  $25,000

  • Land
  • 14,374 Sq Ft
  • $75,758 per Acre

  923 King St, Monticello, FL 32344

  Exceptional cleared corner lot with a concrete slab already in place—ready for your vision! City water and sewer connections are available, with electric at the road. Conveniently located just minutes from downtown Monticello. Motivated Sellers!

  Alicia Radtke All Realty Services

  923 King St, Monticello, FL 32344
• 

  

  /29

  $79,900

  • Land
  • 6.4 Acres
  • $12,484 per Acre

  XXX Hopson Rd, Monticello, FL 32344

  Unique shaped parcel located in a serene rural area—perfect for building, recreation, or investment

  Shanna D'Attile Keller Williams Town & Country

  XXX Hopson Rd, Monticello, FL 32344
• 

  

  /4

  $550,000

  • 6,024 Sq Ft

  535 Hagan St, Monticello, FL 32344

  Rare Investor Opportunity: 7-Unit Residential Complex for Sale Don't miss this fantastic investment opportunity! This well-maintained 7-unit complex features: Six 3-bedroom, 1-bathroom units One 2-bedroom, 1-bathroom unit Walking distance to downtown – perfect for tenants seeking convenience Corner lot location with excellent visibility Designated parking spots for each unit 2023 Roof Whether

  535 Hagan St, 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /38

  $549,000 Open Sun 12PM - 5PM

  • 4 Beds
  • 2.5 Baths
  • 2,233 Sq Ft

  35 Tarn Way, Monticello, FL 32344

  2026 Nailed It Tallahassee Parade of Homes Entry! **Photos are of previous build home will have different finishes. Home will be move in ready May 20th. Amazing new construction 4 bedroom 3 bathroom. Luxurious master suite, Kitchen made of dreams, this is a must see!

  Amber McKinney Hamilton Realty Advisors LLC

  35 Tarn Way, Monticello, FL 32344
• 

  

  /11

  $170,000

  • 2 Beds
  • 1 Bath
  • 962 Sq Ft

  275 W High St, Monticello, FL 32344

  This cozy home is situated in the heart of charming Monticello within walking distance to all the local shops and restaurants. It's perfect for a starter home or someone wanting to downsize for simplicity. The home features an open concept with plenty of natural light from the many windows. Use two barstools at the kitchen island, or set a nice table for a more formal dining experience. The

  Heather Boyd FL-GA Realty & Auction

  275 W High St, 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
• 

  

  /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
• 

  

  /69

  $555,000 New Construction

  • 4 Beds
  • 2 Baths
  • 1,945 Sq Ft

  64 Sanctuary Dr, Monticello, FL 32344

  Just WOW this beautiful new construction home, with top-of-the-line custom finishes. This home gives you all the luxury you are looking for - a primary suite with stunning tongue and groove wood tray ceilings, master bath with stand-alone soaking tub, walk-in shower, double vanity with quartz countertops, an oversized walk-in custom master closet with built-ins. As you approach the living area,

  64 Sanctuary Dr, Monticello, FL 32344
• 

  

  /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
• 

  

  /25

  $400,000

  • 4 Beds
  • 3 Baths
  • 2,870 Sq Ft

  49 Foggy Ln, Monticello, FL 32344

  Welcome to 49 Foggy Lane in Monticello, FL—an exceptional opportunity to own a spacious property with endless potential! This 2,870 sq ft home features 4 generously sized bedrooms and 3 full bathrooms, along with a dedicated office space—perfect for remote work or added flexibility. Enjoy cozy evenings by the wood-burning fireplace, creating a warm and inviting atmosphere throughout the home. The

  Cyndi Ritchey Tallahassee Board of REALTORS®

  49 Foggy Ln, 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
• 

  

  /30

  $175,000

  • 3 Beds
  • 1 Bath
  • 1,662 Sq Ft

  167 Phelps Rd, Lamont, FL 32336

  Charming 3BR/1BA home with incredible potential, nestled on a gorgeous and private one acre lot with no neighbors in sight. The property is filled with beautiful Camelia trees, creating a serene and picturesque setting. A newer workshop sits out back - perfect for hobbies, storage, or projects. Major update includes a 2025 metal roof. Crawlspace inspection has identified needed repairs to

  167 Phelps Rd, Lamont, FL 32336
• 

  

  /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
• 

  

  /41

  $525,000

  • 4 Beds
  • 2.5 Baths
  • 2,134 Sq Ft

  121 Shumard Ct, Monticello, FL 32344

  Beautiful, like-new 2022 farmhouse-style home located in the sought after Crooked Creek area. This spacious 2134 sq ft home features 4 bedrooms and 2.5 baths on a generous .85 acre lot, ideally situated on a quiet cul-de-sac on the west side of Monticello. The open-concept layout offers elegant coffered ceilings crown molding and a cozy gas fireplace with built-in shelving in the living room-

  121 Shumard Ct, Monticello, FL 32344
• 

  

  /27

  $349,000

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

  8156 Waukeenah Hwy, Monticello, FL 32344

  Rare Find! Country Living on 1 Acre-No HOA! Enjoy peaceful country living on a full 1-acre property with no HOA restrictions. This spacious 1774 square foot home features 3 bedrooms and 2 bathrooms with a bright open concept layout. The home features LVP flooring throughout, fresh interior paint in main living area, and a new roof in 2023 for added piece of mind. The primary suite includes a

  8156 Waukeenah Hwy, Monticello, FL 32344
• 

  

  /41

  $550,000

  • 5 Beds
  • 2 Baths
  • 2,268 Sq Ft

  398 Tecumseh Rd, Monticello, FL 32344

  Charming Cape Cod-style home tucked away on 5 acres just minutes to downtown Monticello. This one owner home has been lovingly maintained and reflects years of care and pride of ownership. With over 2200 square feet of living space, the home offers a comfortable layout. The main floor features three bedrooms, one bath, a welcoming living room with a gas fireplace, dining area, kitchen and a

  398 Tecumseh Rd, Monticello, FL 32344
• 

  

  /45

  $789,000

  • 4 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  900 Ridge Rd, Monticello, FL 32344

  Tucked just outside of historic Monticello, this exceptional 11+ acre property offers a refined rural lifestyle without sacrificing everyday convenience. This Jefferson County gem features a much sought after combination of home, acreage, pool, barn and location. The residence itself is over 2300 square feet and is filled with natural light throughout. The open floor plan is perfect for

  900 Ridge Rd, Monticello, FL 32344

Showing Results 1 - 40, Page 1 of 2