Homes for Sale in 32344

• 

  

  

  /24

  $175,000

  • 3 Beds
  • 2 Baths
  • 1,825 Sq Ft

  520 E High St, Monticello, FL 32344

  AFFORDABLE OLD MONTICELLO (FL) HOME. Spacious, good condition, move-in-ready. Convenient, easy walk to charming downtown. Recent basic repairs and renovations (roofing, electrical, etc). Old but very livable and flexible floor plan. Four possible bedrooms, two baths. Recent central heat and air. Large deck equipped with a hot tub (unknown condition) and fenced. Handicap ramp. Huge two-story

  Hines Boyd FL-GA Realty & Auction

  520 E High St, Monticello, FL 32344
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• 

  

  

  /70

  $769,000

  Open Sat 11AM - 2PM $26K PRICE DROP

  • 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
• 

  

  

  /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

  Heather Boyd FL-GA Realty & Auction

  2664 W Washington Hwy, 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. Adjoinging additional lot can also be purchased! 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

  Caleb Stephens Silo Hill Properties

  140 Shumard Ct, Monticello, FL 32344
• 

  

  

  /29

  $625,000

  • 2 Beds
  • 2 Baths
  • 1,592 Sq Ft

  180 Cooper Rd, Monticello, FL 32344

  TWIN SILOS RANCH. NORTH FLORIDA. Idyllic 15+ acres with a charming home, a barn with 4 horse stalls, a shop/garage with an office, 10+ acres of rolling fenced pastures, and a small pond, conveniently located between Monticello (4.5 miles) and Tallahassee (16 miles). This beautiful setting is the ancestral homestead of an old dairy, studded with heritage live oaks, hickory, and the occasional

  Hines Boyd FL-GA Realty & Auction

  180 Cooper Rd, 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
• 

  

  /15

  $60,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  40 Westview Ln, Monticello, FL 32344

  Opportunity awaits in Christmas Acres! Situated on a spacious 1-acre corner lot, this property is being sold AS IS and is ideal for investors, renovators, or those looking for a fresh start. The existing mobile home requires significant repairs, including a new roof, siding, electrical updates, flooring throughout, and HVAC ductwork. Mold is present in the primary bedroom due to a previous water

  Alicia Radtke All Realty Services

  40 Westview Ln, Monticello, FL 32344
• 

  

  /54

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,760 Sq Ft

  73 W Bryant Ct, Monticello, FL 32344

  Completely Renovated Country Retreat on 3⁄4 Acre Near Downtown Monticello Experience the perfect blend of modern comfort and small-town charm in this beautifully renovated 4-bedroom, 2-bath home situated on a cul-de-sac on 3⁄4 of an acre just over a mile from downtown Monticello. Thoughtfully rebuilt from the studs out, this home offers peace of mind with extensive upgrades throughout, including

  Eileen Waller Keller Williams Town & Country

  73 W Bryant Ct, 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

  Norris Bishop Norris Bishop Realty, LLC

  1164 Oaklands Plantation Rd, Monticello, FL 32344
• 

  

  /34

  $425,000

  • 5,818 Sq Ft

  2664 W Washington Hwy Unit Two Homes, Monticello, FL 32344

  Two houses perfect for generational living or rental income. These move-in-ready homes are in good condition, convenient to Monticello while maintaining privacy. The larger home is a 1550's era brick ranch-style home that is well maintained with newer roof (2022), new electric (2025), new plumbing (2025), tankless water heater and whole house generator. The main living area is 2,659 sf with 5

  Heather Boyd FL-GA Realty & Auction

  2664 W Washington Hwy Unit Two Homes, Monticello, FL 32344
• 

  

  /33

  $799,999

  • 3 Beds
  • 2.5 Baths
  • 3,677 Sq Ft

  728 Turney Anderson Rd, Monticello, FL 32344

  A Timeless Treasure, built by Riley Palmer Construction in 2006, this exceptional home captures the warmth and character of an early-1900s Craftsman farmhouse. It is located on 5 beautiful acres with mature pecan trees in the front and pines in the back yard. A spacious wrap around front porch welcomes you and features reclaimed New Orleans style doors and classic architectural details. Inside,

  Jared Parramore Coastwise Realty

  728 Turney Anderson Rd, Monticello, FL 32344
• 

  

  /5

  $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.

  Shelley Poppell Clover Key Realty

  693 Tally Hills Dr, Monticello, FL 32344
• 

  

  /38

  $100,000

  • 3 Beds
  • 1 Bath
  • 1,864 Sq Ft

  340 S Waukeenah St, Monticello, FL 32344

  They don’t build them like they used to! This historic 1900 home located in downtown Monticello sits on nearly a half-acre lot and is full of timeless character waiting to be restored. Featuring original hardwood floors throughout most of the home, beadboard walls, 9+ foot ceilings, and original glass windows, this property offers the charm and craftsmanship so many buyers desire. Spacious

  Alicia Radtke All Realty Services

  340 S Waukeenah St, Monticello, FL 32344
• 

  

  /37

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  60 Bob White Trail, Monticello, FL 32344

  Tucked behind a gated entrance and surrounded by 5.54 acres of open space, this property offers the kind of privacy and freedom that is hard to find at this price point. With no HOA, you have the flexibility to truly enjoy country living with room for livestock, horses, RVs, trailers, ATVs, UTVs, and more. As you arrive, you are welcomed by a wide open parking area with plenty of space for all

  Kyle Footman ROGERS BARRY, REALTOR

  60 Bob White Trail, Monticello, FL 32344
• 

  

  /43

  $375,000

  • 3 Beds
  • 3 Baths
  • 2,706 Sq Ft

  339 Silver Lake Rd, Monticello, FL 32344

  Large home on 5 acres mostly pasture~very peaceful setting~BRAND NEW LVP~Open concept with vaulted ceilings~large oaks~perfect pasture for horses or cattle~No HOA~

  Steve Walker Steve C. Walker Realty, LLC

  339 Silver Lake Rd, Monticello, FL 32344
• 

  

  /4

  $299,000

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

  0 Big Joe Rd Unit 399642, Monticello, FL 32344

  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 hospitality concepts, or future

  Lynnaye Boyd Resilience Realty

  0 Big Joe Rd Unit 399642, Monticello, FL 32344
• 

  /2

  $319,900

  New Construction $2K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,550 Sq Ft

  300 Bowman St, Monticello, FL 32344

  Recently built home featuring spacious open floor plan. Kitchen has raised cabinets, granite counters, stainless steel appliances, large island with plenty of seating & a pantry....overlooks spacious family area with plenty of room for large gatherings, plus separate dining space. First floor also offers 1/2 bath and large storage area under stairs. Upstairs you are greeted with open reading area

  Steve Walker Steve C. Walker Realty, LLC

  300 Bowman St, Monticello, FL 32344
• 

  

  /5

  $58,000

  • Land
  • 38,768 Sq Ft
  • $65,169 per Acre

  0 Spring Hollow Dr, Monticello, FL 32344

  Don't miss this exceptional 0.89-acre homesite in the Desirable Cooper's Pond community. This lot offers the perfect opportunity to create your dream home in a well-established neighborhood known for its attractive surroundings and welcoming atmosphere. Enjoy the convenience of being just minutes from town, with easy access to shopping, dining, schools, and everday amenities while still

  Ellen Fokes CONSULTANTS TO HOMEBUI

  0 Spring Hollow Dr, 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
• 

  

  /70

  $1,325,000

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

  221 Kiley Dr, Monticello, FL 32344

  Welcome to a rare North Florida estate just minutes from Tallahassee—where luxury, land, and lifestyle come together. 221 Kiley Road is situated on expansive acreage in Monticello, and this private retreat offers the perfect blend of seclusion and convenience, located just a short drive from the heart of Tallahassee. For buyers seeking space, privacy, and versatility without sacrificing proximity

  Wilda Sigler Keller Williams Town & Country

  221 Kiley Dr, 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

  Caleb Stephens Silo Hill Properties

  535 Hagan St, Monticello, FL 32344
• 

  

  /63

  $259,999

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

  196 Private Rd, Monticello, FL 32344

  Looking for a peaceful escape from the hustle and bustle? Welcome to your own private piece of North Florida! Tucked away on 5 beautiful acres between Tallahassee and historic Monticello, this spacious mobile home offers 1,792 square feet of comfortable living space with room to spread out and make it your own. Enjoy quiet mornings on the inviting front porch or unwind in the evenings on the

  Hunter Key OaksFeather Realty

  196 Private Rd, Monticello, FL 32344
• 

  

  /42

  $469,997

  New Construction

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

  51 Tarn Way, Monticello, FL 32344

  MOVE IN READY!! 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
• 

  

  /3

  $19,500

  • Land
  • 37,461 Sq Ft
  • $22,674 per Acre

  0 Cox Rd Unit 400763, Monticello, FL 32344

  0.84-Acre Monticello Lot on Cox Rd – SURVEY & ELEVATION LETTER ALREADY COMPLETED! Excellent opportunity to own a peaceful 0.84-acre parcel (Lots 89 & 90 of Springdale Pecan Plantation) located on Cox Road in beautiful Jefferson County. Surrounded by natural North Florida beauty, this lot offers rural tranquility while keeping you just minutes from historic downtown Monticello and 25-30 minutes to

  Stephen Hachey Flat Fee MLS Realty

  0 Cox Rd Unit 400763, Monticello, FL 32344
• 

  

  /52

  $395,000

  $54K PRICE DROP

  • 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 an opportunity to restore and 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

  Rachel Sparling All Realty Services

  930 E Pearl St, Monticello, FL 32344
• 

  

  /19

  $395,000

  $104K PRICE DROP

  • Land
  • 3.2 Acres
  • $123,438 per Acre

  XX Shiver Rd, Monticello, FL 32345

  Beautiful High lot at corner of Hwy 19, Shiver and Lake Rd. This listing is compilation of 3 contiguous parcels : (19-2N-5E-0140-0000-0300 and 19-2N-5E-0000-0210-0000 and 19-2N-5E-0140-0000-0170). for a total of 3.25 acres . PRIME location for multi-family, office, mixed use commercial business that needs visibility and ease of access. Utilities available- Water access to main line is Under Hwy

  Jennifer Ward Century 21 First Story

  XX Shiver Rd, Monticello, FL 32345
• 

  

  /26

  $69,900

  $14K PRICE DROP

  • Land
  • 6.4 Acres
  • $10,922 per Acre

  XXX Hopson Rd, Monticello, FL 32344

  Owner Financing available with 20% down. Motivated Seller! 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
• 

  

  /70

  $395,000

  $15K PRICE DROP

  • 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

  Catherine Hope All Realty Services

  1637 N Jefferson Hwy, Monticello, FL 32344
• 

  

  /19

  $449,900

  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

  Jared Parramore Coastwise Realty

  855 S Waukeenah St, Monticello, FL 32344
• 

  

  /11

  $60,000

  $20K PRICE INCREASE

  • Land
  • 2.36 Acres
  • $25,424 per Acre

  0 Central Rd Unit 381525, Midway, FL 32344

  2.36 acre wooded lot for sale located down a paved road with access to cable and internet services. Land is high and dry. No mobile homes allowed.

  Malcolm Davis Broger Real Estate Services

  0 Central Rd Unit 381525, Midway, 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

  Renee Smawley Steve C. Walker Realty, LLC

  254 Woodland Dr, Monticello, FL 32344
• 

  

  /3

  $1,190,000

  • 4 Beds
  • 4 Baths
  • 3,043 Sq Ft

  4264 Safari Run, Tallahassee, FL 32309

  New construction, East side of town this 4 Bedroom 4 Bath home with office and private sitting in master this home is a luxury on 2/12 acres. completion in early Aug 2026

  Robert Paynter Keller Williams Town & Country

  4264 Safari Run, Tallahassee, FL 32309
• 

  

  /3

  $299,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,575 Sq Ft

  12180 Gamble Rd, Monticello, FL 32344

  New Construction currently being built by Southern Construction. Home should be completed in August 2026. Home is located in a great location in S. Jefferson County, close to the Wacissa River. Home features 3 beds and 2 baths, hardi siding, granite countertops with large kitchen island, open floor plan, and vinyl plank flooring in bedrooms and common area. Master bath features large walk-in tile

  Jared Parramore Coastwise Realty

  12180 Gamble Rd, Monticello, FL 32344
• 

  

  /22

  $164,900

  $110K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,553 Sq Ft

  34 W Hummingbird Ln, Monticello, FL 32344

  *Some photos may be virtually staged* New beautiful LVP flooring on mother in law suite side of the property and wdo repair underneath the new flooring!! So many options with this property!! It boasts 2 separate living spaces joined by a common family room. One side of the home has 1 bed and 1 bath, it's own kitchen and living space. The other side of the home has 3 bedrooms, 2 bathrooms and the

  Susan Gillespie Lord & Stanley Realty, Inc.

  34 W Hummingbird Ln, Monticello, FL 32344
• 

  

  /7

  $40,000

  • Land
  • 1.01 Acres
  • $39,604 per Acre

  000 Westview Ln, Monticello, FL 32344

  Discover the perfect blend of privacy and potential with this wooded 1.01-acre lot. Whether you're looking to build your dream home or bring in a manufactured home, this property offers the flexibility to make your vision a reality. A well is already in place, helping reduce development costs, and community sewer is available for hookup. Enjoy the freedom of NO HOA and NO deed restrictions. Bring

  Alicia Radtke All Realty Services

  000 Westview Ln, Monticello, FL 32344
• 

  

  /44

  $390,000

  $40K PRICE INCREASE

  • 2,750 Sq Ft

  480 S Jefferson St, Monticello, FL 32344

  Located in the heart of Monticello, this 5-unit investment property offers a prime opportunity for investors looking to add value and generate income. Positioned just minutes from local businesses, shopping, dining, and convenient interstate access, the location provides strong appeal for tenants seeking both convenience and accessibility. Currently, 3 of the units are occupied, providing

  Chip Williams Keller Williams Town & Country

  480 S Jefferson St, Monticello, FL 32344
• 

  

  /4

  $75,000

  $16K PRICE INCREASE

  • Land
  • 12,632 Sq Ft
  • $258,621 per Acre

  205 E Cherokee Ave, Monticello, FL 32344

  Prime vacant cleared commercial lot in downtown Monticello. Zoned Commercial B-2 Business Highway. Located Steps from US 19 South Across street from Burger King and Dollar Tree. Next door to Oreilly's Auto parts. High Traffic area and Good visibility. Address is for GPS only. Acreage is subject to survey.

  Starbuck Rissman Steve C. Walker Realty, LLC

  205 E Cherokee Ave, Monticello, FL 32344
• 

  

  /29

  $434,000

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

  285 Mallard Ln, Monticello, FL 32344

  One or more pictures is virtually enhanced *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

  Shelley Duke Red Bird Realty

  285 Mallard Ln, Monticello, FL 32344
• 

  

  /24

  $736,951

  • 2 Beds
  • 1 Bath
  • 1,296 Sq Ft

  10481 Ashville Hwy, Greenville, FL 32331

  Sportsman's Paradise Nature Preserve Quiet Country Living (2 Ponds) Bordering Plantation on 2 sides. "Out in the country past the city limit signs"..a diamond in the rough giving "Little House on the Prairie" vibes could easily be manicured and restored to perfection. Plenty of potential with almost 30 acres. Two ponds seem to be spring fed full of water, fantastic recreational spot in rural

  Starbuck Rissman Steve C. Walker Realty, LLC

  10481 Ashville Hwy, Greenville, FL 32331

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