Monticello, FL Homes for Sale with Acreage

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  /46

  $325,000

  • 4 Beds
  • 2 Baths
  • 2,304 Sq Ft

  947 Piney Woods Rd, Monticello, FL 32344

  Charming 2022 Mobile Home on 5 Peaceful Acres A rare blend of modern comfort and wide-open space, this 2022 mobile home sits on 5+ acres—perfect for anyone craving privacy, freedom, and room to grow. Whether you dream of a hobby farm, a quiet country retreat, or simply a place with no close neighbors, this property delivers. Embrace freedom of country living with the convenience of a modern home.

  

  Brian Bachman

  Kelly & Kelly Properties, Inc

  947 Piney Woods Rd, Monticello, FL 32344
• Explore Monticello

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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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  /2

  $50,000

  • Land
  • 2.5 Acres
  • $20,000 per Acre

  TBD E Meadow Rd, Monticello, FL 32344

  Wooded lot, pines and hardwoods. Mobile homes are allowed. High elevation.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD E Meadow Rd, 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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  /32

  $1,805,000

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

  Vacant N Salt Rd, Monticello, FL 32344

  192± acre organic cattle farm located in beautiful Jefferson County, Florida Certified organic operation for 20+ years with a long-standing history of sustainable land stewardship Fully fenced and cross-fenced for efficient cattle rotation and livestock management Improved pastureland ideal for cattle, horses, or continued agricultural use Several picturesque homesites overlooking the scenic

  

  Ben Jones

  MOSSY OAK PROPERTIES

  Vacant N 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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  /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
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  /70

  $1,950,000

  $50K PRICE DROP

  • 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
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  /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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  /49

  $398,900

  $26K PRICE DROP

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

  1628 N Jefferson Hwy, Monticello, FL 32344

  For generations, this beautifully maintained, one-family owned brick home has been a place where holidays were celebrated, children were raised, and life's everyday moments became treasured memories. Today, with only one family member remaining, the home has simply become more space than one person needs. Rather than seeing it sit too quietly, she hopes to pass it on to another family who will

  

  Lynette Sirmon

  All Realty Services

  1628 N Jefferson Hwy, Monticello, FL 32344
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  /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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  /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

  $2,735,850

  $50K PRICE DROP

  • 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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  /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 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 cattle,

  

  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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  /36

  $584,000

  • 3 Beds
  • 3.5 Baths
  • 2,148 Sq Ft

  8250 Waukeenah Hwy, Monticello, FL 32344

  Enjoy two private year around spring fed ponds! Escape to your own private sanctuary on 30 breathtaking acres where nature, privacy, and craftsmanship come together. This custom-built retreat features soaring vaulted ceilings, expansive windows, & French doors- blurring the line between indoors and out, flooding every room with natural light and serene views. 2 Bed, 2.5 Bath, thoughtfully

  

  Bhishma Benedict

  FLORIDA HOMES REALTY & MORTGAGE GVILLE

  8250 Waukeenah Hwy, Monticello, FL 32344
• 

  

  /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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  /7

  $109,000

  • Land
  • 5 Acres
  • $21,800 per Acre

  130 Sweetfield Rd, Monticello, FL 32344

  Mobile-home-friendly property with a cleared homesite and an existing well, septic system, and electrical service already on the property. Seller financing is available. Conveniently located near I-10 and approximately 30 minutes from Tallahassee. Bring your home plans and enjoy a quiet country setting with room for animals, gardening, outdoor projects, and additional storage. Fence the property

  Moe Mossa Savvy Avenue, LLC

  130 Sweetfield 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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  /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 Bespoke Realty of Tallahassee

  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

  All Offers considered..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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  /2

  $125,000

  • Land
  • 5.96 Acres
  • $20,973 per Acre

  0 Eastwood Unit 402606, Monticello, FL 32344

  Back on the market - Discover the perfect place to build your dream home on this beautiful nearly 6-acre parcel! Enjoy the peace and privacy of country living with the convenience of being just minutes from the interstate and a short drive to Tallahassee. With plenty of room for your custom home, workshop, gardens, or recreational space, the possibilities are endless! Whether you’re looking to

  D. Scott Kilgore Superior Realty Group LLC

  0 Eastwood Unit 402606, Monticello, FL 32344
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  /70

  $915,000

  • 3 Beds
  • 2.5 Baths
  • 2,412 Sq Ft

  4216 W Washington Hwy, Monticello, FL 32344

  Tucked away on 10.87 private acres behind its own gated entrance in the sought-after Rainey Run community, this custom-built home offers the perfect balance of quality craftsmanship, modern comfort, and peaceful country living. Built by Hannon Construction in 2023, the 3-bedroom, 2.5-bath home spans 2,412 square feet and was thoughtfully designed with timeless finishes and functional spaces

  Savannah Stephens Hill Spooner & Elliott Inc

  4216 W Washington Hwy, Monticello, FL 32344
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  /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
• 

  

  /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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  /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
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  /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
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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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  /66

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,422 Sq Ft

  195 Coopers Pond Rd, Monticello, FL 32344

  Wonderful family home in great neighborhood~Located on a quiet street, this home sits on a full acre and is ready for new owners~huge walk-in shower~breakfast nook~jetted tub in 2nd bathroom~walk-in closet in master~screened porch overlooking private backyard~partially fenced~2-car garage~nice yard with large oaks ~~Zero turn lawnmower included with acceptable offer~~

  Renee Smawley Steve C. Walker Realty, LLC

  195 Coopers Pond Rd, Monticello, FL 32344
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  /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
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  /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
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  /68

  $695,000

  • 5 Beds
  • 3 Baths
  • 3,536 Sq Ft

  2247 Waukeenah Hwy, Monticello, FL 32344

  Just 3 miles south of Monticello, FL and only 2.5 miles from I-10, this 10.45 acre working homestead has been thoughtfully set up for country living, livestock and extended family. The 3,536 sq. ft. home features 4 bedrooms/2 baths in the main house (with the set up for an additional bath upstairs) master is conveniently located downstairs with two walk-in closets, private access, plenty of

  Alicia Radtke All Realty Services

  2247 Waukeenah Hwy, 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

  $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
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  /69

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 4,762 Sq Ft

  974 Rainey Run, Monticello, FL 32344

  **Some Photos are Virtually Enhanced** Experience luxury living in the prestigious gated community of Rainey Run. This is where privacy, nature, and convenience come together on 10 breathtaking acres. Surrounded by towering hardwoods and abundant wildlife, this remarkable property offers a convenient peaceful retreat. Built in 2020, this custom home showcases quality craftsmanship with a highly

  Renee Dawkins Dawkins Realty LLC

  974 Rainey Run, Monticello, FL 32344
• 

  

  /70

  $395,000

  Open Sat 10AM - 12PM $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
  • 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

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