Monticello, FL Homes for Sale with Acreage

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  /56

  $1,175,000

  • 3 Beds
  • 2 Baths
  • 2,612 Sq Ft

  1590 Tyson Rd, Monticello, FL 32344

  Experience the beauty and tranquility of North Florida living on this stunning estate located just south of Monticello with an easy commute to Tallahassee. This remarkable property features a mature pecan grove, two scenic ponds, along with a creek and open pasture perfect for horses or livestock. The centerpiece of the property is a beautifully crafted home filled with warmth, charm, and custom

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  1590 Tyson Rd, Monticello, FL 32344
• Explore Monticello

• 

  

  

  /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,

  

  Chance Shutes

  Keller Williams Town & Country

  305 Old Lloyd Rd, Monticello, FL 32344
• 

  

  /2

  $65,000

  $10K PRICE DROP

  • Land
  • 1.7 Acres
  • $38,235 per Acre

  TBD Scott Dr, Monticello, FL 32344

  1.7 acres, two lots hidden in Monticello. Will not divide. Private setting with Plantation to the west. There is a 15 ft recorded easement to the property but currently working on additional road access. No sign on property. .

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD Scott Dr, Monticello, FL 32344
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  /51

  $398,900

  $26K PRICE DROP

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

  1628 N Jefferson Hwy, Monticello, FL 32344

  Picturesque, 3/2, brick beauty with a whimsical style that evokes the charm of a traditional storybook estate, with 3,127 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

  1628 N Jefferson Hwy, 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

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  8156 Waukeenah Hwy, Monticello, FL 32344
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  /21

  $172,500

  • Land
  • 10 Acres
  • $17,250 per Acre

  TBD Rainey Run, Monticello, FL 32344

  Gated rural community, lakefront 10 acres with large hardwoods. Tranquility awaits, gently sloping land with some clearing.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD Rainey Run, Monticello, FL 32344
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  /57

  $529,000

  $56K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,187 Sq Ft

  515 E Palmer Mill Rd, Monticello, FL 32344

  **MOTIVATED SELLERS - CONCESSION(S) BEING OFFERED** Remarkable, peaceful in-town oasis on 3.54 acres! An incredible find in the heart of downtown Monticello, FL. Not only is this home located on a private 3.54 acre spread, surrounded by a perimeter of natural foliage, but the home itself has been beautifully updated, blending the charm of old and the convenience of new. The 3 bedroom/3 bathroom,

  

  Brenna Kelly-Ward

  Kelly & Kelly Properties, Inc

  515 E Palmer Mill Rd, Monticello, FL 32344
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  /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

  

  Chance Shutes

  Keller Williams Town & Country

  305 Old Lloyd Rd, Monticello, FL 32344
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  /12

  $165,000

  $10K PRICE DROP

  • Land
  • 10.47 Acres
  • $15,759 per Acre

  5936 Vista Rd, Monticello, FL 32344

  Perfect opportunity to own 10+ acres to build your dream home on this blank slate. Lot is mostly flat and backs up to a power line so no building behind the property. Abundant wildlife present (deer and turkey) and bring all your yard animals. Ride up Vista Road to see your neighbors on larger lots to Waukeenah Hwy to visit the beautiful Monticello Vineyards and Winery. Lot dimensions are

  

  Jacquelynn Harrison-Cofty

  Advantage Premier Realty LLC

  5936 Vista Rd, Monticello, FL 32344
• 

  

  /55

  $765,000

  • 3 Beds
  • 2.5 Baths
  • 2,436 Sq Ft

  9901 Gamble Rd, Monticello, FL 32344

  PRIVATE 20-ACRE ESTATE MINUTES FROM TALLAHASSEE - TRAILS, WILDLIFE, PASTURE & CUSTOM HOME (ADJOINING 21 ACRES AVAILABLE-MLS#400837) Nestled among majestic oaks and rolling countryside, this exceptional estate offers a rare combination of privacy, natural beauty and comfortable country living. Beyond the gated entrance lies a beautiful setting of open land, mature trees, and abundant wildlife,

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  9901 Gamble Rd, Monticello, FL 32344
• 

  

  /4

  $130,000

  • Land
  • 9.96 Acres
  • $13,052 per Acre

  00 Mallard Blue Jay Ln Unit 2/3, Monticello, FL 32344

  The listing contains (2) adjacent raw land parcels in the Lloyd Acres Subdivision = 9.96 acres total. See parcel IDs: 18-1N-4E-0113-000C-0010 (6.41 acres; Mallard Lane) + 18-1N-4E-0112-000C-0050 (3.55 acres; Bluejay Rd). Look for real estate signs (2) to help identify the acreage for sale. The property is zoned Residential-01 (1 home/1 acre), making it a great opportunity for someone wanting to

  

  Brenna Kelly-Ward

  Kelly & Kelly Properties, Inc

  00 Mallard Blue Jay Ln Unit 2/3, Monticello, FL 32344
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  /45

  $1,805,000

  • Land
  • 192 Acres
  • $9,401 per Acre

  Vacant N Salt Rd, Monticello, FL 32344

  192 Acre Organic Cattle Farm in Jefferson County, Florida192 acre organic cattle farm located in beautiful Jefferson County, FloridaCertified organic operation for 20+ years with a long-standing history of sustainable land stewardshipFully fenced and cross-fenced for efficient cattle rotation and livestock managementImproved pastureland ideal for

  

  Ben Jones

  Mossy Oak Properties Southern Land and Homes, LLC

  Vacant N Salt Rd, Monticello, FL 32344
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  /2

  $139,000

  • Land
  • 5 Acres
  • $27,800 per Acre

  TBD Orchard Ln, Monticello, FL 32344

  Great Location in Western Jefferson County offering country living with the convenience of Tallahassee only minutes away. Wooded 5 acres on private lane. Restricted for site built homes with minimum of 1200 sq ft heated and cooled. Adjoining 5 available for sale.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD Orchard Ln, Monticello, FL 32344
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  /41

  $499,000

  $51K PRICE DROP

  • 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

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  398 Tecumseh Rd, Monticello, FL 32344
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  /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.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD W Washington, Monticello, FL 32344
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  /10

  $253,080

  • Land
  • 21.09 Acres
  • $12,000 per Acre

  tbd Gamble Rd, Monticello, FL 32344

  Nature at its best, 21 acres of virgin forest with massive pines and a variety of hardwoods including a mixture of oaks, magnolias and hickory. Beautiful natural setting of rolling land with trails that meander through the property with an abundance of wildlife. Just up the road from the Wacissa River. The second parcel ID is 22-1S-3W-0000-0023-0000. ADJOINING HOME AND 20 ACRES AVAIABLE FOR

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  tbd Gamble Rd, Monticello, FL 32344
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  /49

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 3,832 Sq Ft

  4589 Ashville Hwy, Monticello, FL 32344

  Nestled on 5.56 acres of fenced pastureland, this stunning estate, is framed by majestic oak trees and welcomes you through a private gated entrance. From the rocking chair front porch to the thoughtfully designed interior, this property offers the perfect blend of luxury and country living. Living room kitchen combination with the stone fireplace creating a warm and inviting focal point. The

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  4589 Ashville Hwy, Monticello, FL 32344
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  /16

  $495,000

  $54K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  640 Nautilus Dr, Monticello, FL 32344

  Secluded 56.37 Acres with Metal Building & Living Quarters -Western Jefferson County. This property offers privacy, versatility and room to build or expand. The land features a 2880 sq ft heavy-gauged metal building designed for both residential and workshop use. Second floor includes 1200 sf of living space currently unfinished featuring two bedrooms, kitchen and living area and one bath. A

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  640 Nautilus Dr, Monticello, FL 32344
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  /18

  $25,000

  • Land
  • 4 Acres
  • $6,250 per Acre

  TBD S Salt Rd, Monticello, FL 32344

  This beautiful old Florida habitat is great for wildlife observation, birding, native forest growth, riding four-wheelers, building nesting boxes for ducks and bats or a hammock and a place to get away for primitive camping. Costco in Tallahassee, Florida is 30.4 miles and Walmart Supercenter in Perry, Florida is 32.1 miles. Monticello, Florida is 9.3 miles for Ice Cream and boutiques, shops,

  

  Lynette Sirmon

  All Realty Services

  TBD S Salt Rd, Monticello, FL 32344
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  /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

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  576 Cox Rd, Monticello, FL 32344
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  /19

  $281,800

  $68K PRICE DROP

  • Land
  • 70.45 Acres
  • $4,000 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
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  /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
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  /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
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  /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

  Lee Hall Capital City Real Estate Group

  625 E Washington St, Monticello, FL 32344
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  /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.

  Starbuck Rissman Steve C. Walker Realty, LLC

  1 W Meadow Rd, Monticello, FL 32344
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  /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 HVAC June 2026 with 10 year parts warranty, plus 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

  Catherine Hope All Realty Services

  1012 S Main Ave, Monticello, FL 32344
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  /37

  $269,900

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

  60 Bob White Trail, Monticello, FL 32344

  Tucked behind a gated entrance and nestled on 5.54 acres, this property offers the privacy, space, and freedom that is hard to find at this price point. With no HOA, you'll have the flexibility to enjoy true country living with plenty of room for horses, livestock, RVs, trailers, ATVs, UTVs, and more. Upon arrival, you're greeted by a large, open parking area with ample space for vehicles,

  Kyle Footman ROGERS BARRY, REALTOR

  60 Bob White Trail, Monticello, FL 32344
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  /61

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 2,873 Sq Ft

  761 Hawkins Rd, Monticello, FL 32344

  This one truly has it all! Nestled on 5+ private acres in beautiful Monticello, Florida, this 4-bedroom, 2.5-bath home offers the perfect blend of comfort, privacy, and charm. Step inside to a spacious split floor plan featuring 10-foot tray ceilings, real hardwood floors, a cozy wood-burning fireplace, and abundant natural light throughout. The beautifully updated kitchen features granite

  Kayla Meadows Keller Williams Town & Country

  761 Hawkins Rd, Monticello, FL 32344
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  /70

  $769,000

  $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
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  /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
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  /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
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  /31

  $269,900

  $15K 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
• 

  

  /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
• 

  

  /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
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  /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
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  /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
• 

  

  /70

  $395,000

  Open Sat 11AM - 2PM $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
• 

  

  /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

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