Homes for Sale in 32344

• 

  

  

  /70

  $754,000

  $41K 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
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• 

  

  

  /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

  $679,900

  $55K PRICE INCREASE

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

  140 Shumard Ct, Monticello, FL 32344

  NOW INCLUDES ADDITIONAL LOT!! 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

  Caleb Stephens Silo Hill Properties

  140 Shumard Ct, Monticello, FL 32344
• 

  

  /2

  $79,000

  • Land
  • 19,602 Sq Ft
  • $175,556 per Acre

  Lot 12 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes BOTH Lot 12 & 23 directly behind it totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 12 E Washington St, Monticello, FL 32344
• 

  

  /2

  $79,000

  • Land
  • 19,602 Sq Ft
  • $175,556 per Acre

  Lot 13 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes BOTH Lot 13 & 22 directly behind it totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 13 E Washington St, Monticello, FL 32344
• 

  

  /31

  $259,900

  $25K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /3

  $39,900

  • Land
  • 1.91 Acres
  • $20,890 per Acre

  76 Barnes Rd, Monticello, FL 32344

  Discover the perfect spot to build your dream home or weekend getaway on this 1.91-acre property in Monticello! Featuring paved road frontage, a partially cleared homesite, and plenty of room to enjoy the surrounding natural beauty, this property offers the ideal balance of privacy and convenience. Located with easy access to both Monticello, FL and Thomasville, GA, you’ll enjoy peaceful country

  Crystal Bochnia Madison Realty Group, LLC

  76 Barnes Rd, Monticello, FL 32344
• 

  /2

  $95,000

  • Land
  • 2.22 Acres
  • $42,793 per Acre

  450 Oconee Ln, Monticello, FL 32344

  Vacant building lot; inside the city limits, city water and sewer are available, all high and dry; very nice neighborhood, no HOA.

  Steve Walker Steve C. Walker Realty, LLC

  450 Oconee Ln, 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 Armor Realty, Inc

  0 Spring Hollow Dr, Monticello, FL 32344
• 

  

  /12

  $179,900

  $5K PRICE DROP

  • 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
• 

  

  /28

  $3,999

  $17K PRICE DROP

  • 2 Beds
  • 2 Baths

  10 S Front Ct, Monticello, FL 32344

  If you purchase this home, receive 2 months FREE site rent plus pay NO application fees. Hurry! Offer expires August 31, 2026. Act fast! Restrictions apply. Looking for an affordable home with plenty of potential? This handyman special is the perfect opportunity to add your personal touch and build instant sweat equity. With a functional layout, generous living space, and solid bones, this home

  Patty Davis Jefferson Pines

  10 S Front Ct, Monticello, FL 32344
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  /56

  $305,000

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft

  395 Sunset Dr, Monticello, FL 32344

  Welcome home to this charming 3-bedroom, 2-bath property set on a spacious lot with a fully fenced backyard. Thoughtfully updated throughout, major improvements include a 2023 metal roof, new HVAC system, new windows, and a new electric on-demand water heater. The renovated kitchen features all new appliances and a clean, modern look. The second full bath is conveniently located just off the rear

  Catherine Hope All Realty Services

  395 Sunset Dr, Monticello, FL 32344
• 

  /2

  $69,000

  • Land
  • 19,602 Sq Ft
  • $153,333 per Acre

  Lot 14 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes BOTH Lot 14 & 21 directly behind it totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 14 E Washington St, Monticello, FL 32344
• 

  

  /44

  $235,000

  • 3 Beds
  • 1 Bath
  • 1,700 Sq Ft

  810 E Dogwood St, Monticello, FL 32344

  Step back in time and discover the charm of this classic Monticello home, offering timeless character and endless possibilities. Built in 1915, this Craftsman-style residence features 1,700 square feet of living space with hardwood floors, separate living and dining areas that reflect the home's historic appeal, 3 full bedrooms, with a large mud room and separate sitting room, a wood-burning

  Michael Balanoff Re/Max Professionals Realty

  810 E Dogwood St, Monticello, FL 32344
• 

  

  /7

  $150,000

  $48K PRICE DROP

  • 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
• 

  

  /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
• 

  /2

  $254,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,235 Sq Ft

  360 Bowman St, Monticello, FL 32344

  New construction; very convenient to downtown; house is close to completion - should be ready in about 45 days.

  Steve Walker Steve C. Walker Realty, LLC

  360 Bowman St, 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

  $325,000

  $174K PRICE DROP

  • Land
  • 3.2 Acres
  • $101,562 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
• 

  

  /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
• 

  /2

  $85,000

  • Land
  • 19,602 Sq Ft
  • $188,889 per Acre

  Lot 11 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes BOTH Lot 11 & 24 directly behind it totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 11 E Washington St, Monticello, FL 32344
• 

  /2

  $85,000

  • Land
  • 2.05 Acres
  • $41,463 per Acre

  Lot 25 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes 10 Lots- 25-35 (Survey) totaling 2.05 Acres.

  Liz Kuntz Keller Williams Town & Country

  Lot 25 E Washington 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
• 

  

  /19

  $424,900

  New Construction $20K PRICE DROP

  • 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
• 

  

  /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
• 

  /2

  $350,500

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft

  1565 Sweetbay Ct, Monticello, FL 32344

  This home is currently coming out of the permitting phase. New construction will start in the next week. Completion date should be approx 4 months or less. We will update the comments as the construction progresses. Picture is virtual. More to come as construction continues.

  Steve Walker Steve C. Walker Realty, LLC

  1565 Sweetbay Ct, Monticello, FL 32344
• 

  

  /44

  $364,900

  $15K 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
• 

  /2

  $69,000

  • Land
  • 19,602 Sq Ft
  • $153,333 per Acre

  Lot 16 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes 4 Lots- 16 & 17 with 18 & 19 directly behind it, totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 16 E Washington St, Monticello, FL 32344
• 

  

  /9

  $175,000

  • Land
  • 37 Acres
  • $4,730 per Acre

  Vacant E Washington Hwy, Monticello, FL 32344

  37 ACRES, AUCILLA RIVER HUNTING TRACT NEAR MONTICELLO. FL. Fronts on US 90 1⁄2 mile west of the Aucilla River—perhaps the most prolific wildlife corridor in the county. The NE half of the property is an extension of the river’s drainway and borders SRWMD land on two sides. It’s a great wildlife habitat. The SW half along US 90 and Gramling Road is composed of a soil type (Plummer) suitable for

  Hines Boyd FL-GA Realty & Auction

  Vacant E Washington Hwy, 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
• 

  /2

  $69,000

  • Land
  • 19,602 Sq Ft
  • $153,333 per Acre

  Lot 15 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes BOTH Lot 15 & 20 directly behind it totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 15 E Washington St, Monticello, FL 32344
• 

  

  /46

  $949,000

  • 3 Beds
  • 2.5 Baths
  • 2,790 Sq Ft

  307 Crabapple Ln, Monticello, FL 32344

  One or more photos are enhanced. A rare opportunity to own a truly one-of-a-kind custom estate! Nestled on a private, fully fenced homesite overlooking 26 acres of golf course-like grounds, this 2021 custom-build home offers over 2,700 square feet of thoughtfully designed living space with breathtaking 270 views, including peaceful creek frontage. Built for both luxury and peace of mind, the home

  Shelley Poppell Clover Key Realty

  307 Crabapple Ln, Monticello, FL 32344
• 

  

  /29

  $429,000

  $5K PRICE DROP

  • 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
• 

  

  /6

  $149,999

  • Land
  • 8 Acres
  • $18,750 per Acre

  0 E Beth Page Rd, Monticello, FL 32344

  The property features flat, wooded land with plenty of road frontage, is not located in a flood zone, and has no apparent access issues. Power is available at the road, while water and sewer would require private well and septic system. No recent survey or perc test has been completed, and the property has a free and clear title with current taxes. Conveniently located just minutes from downtown

  Anthony Gigilo TOP BROKERAGE, LLC

  0 E Beth Page Rd, Monticello, FL 32344
• 

  

  /24

  $736,951

  • 2 Beds
  • 1 Bath
  • 1,296 Sq Ft

  10481 Ashville Hwy, Greenville, FL 32331

  Bring All Offers!!! 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

  Starbuck Rissman Steve C. Walker Realty, LLC

  10481 Ashville Hwy, Greenville, FL 32331
• 

  /2

  $39,900

  • Land
  • 1.91 Acres
  • $20,890 per Acre

  Vacant Barnes Rd, Monticello, FL 32344

  Discover the perfect spot to build your dream home or weekend getaway on this 1.91-acre property in Monticello! Featuring paved road frontage, a partially cleared homesite, and plenty of room to enjoy the surrounding natural beauty, this property offers the ideal balance of privacy and convenience. Located with easy access to both Monticello, FL and Thomasville, GA, you’ll enjoy peaceful country

  Crystal Bochnia Madison Realty Group, LLC

  Vacant Barnes Rd, Monticello, FL 32344

Showing Results 41 - 79, Page 2 of 2