Monticello, FL Homes

/42
$415,000 Under Contract
- 3 Beds
- 2 Baths
- 1,921 Sq Ft
2497 Boston Hwy, Monticello, FL 32344

Charming Hillside Country Retreat with Barn and Acreage. Welcome to your dream countryside escape! This beautifully maintained brick home sits peacefully on a hillside, surrounded by sprawling fields dotted with mature pecan trees. Inside, the home features a spacious open floor plan, perfect for entertaining or relaxing with family. The large kitchen offers ample workspace and storage, while the

Pam Kelly

Kelly & Kelly Properties, Inc

(448) 334-5566

2497 Boston Hwy, Monticello, FL 32344
/36
$285,000 Sold Aug 08, 2025

705 N Mulberry St, Monticello, FL 32344
- 3 Beds
- 2.5 Baths
- 1,527 Sq Ft
- Built 2004
Last Sold Summary
- 1% Below List Price
- $187/SF
- 40 Days On Market
Current Estimated Value $276,738

Last Listing Agent Bill Lord Armor Realty, Inc

705 N Mulberry St, Monticello, FL 32344

/19
Not Listed For Sale
- 2 Beds
- 2 Baths
- 960 Sq Ft
401 E Osprey Ln, Monticello, FL 32344

401 E Osprey Ln, Monticello, FL 32344

/40
$465,000 Under Contract
- 3 Beds
- 2 Baths
- 1,858 Sq Ft
165 Crooked Creek Ln, Monticello, FL 32344

Welcome to 165 Crooked Creek Lane in Monticello, Florida—a beautifully maintained home situated on a spacious 0.8-acre fully sodded lot with thoughtful upgrades throughout and exceptional outdoor features. Inside, the home offers comfort and efficiency with 3-inch blinds on all windows (including the garage), ceiling fans in every bedroom, the living room, and the library, and a cozy gas

Chance Shutes

Keller Williams Town & Country

(448) 333-1873

165 Crooked Creek Ln, Monticello, FL 32344
/3
$2,989,892 Sold May 12, 2025

0 Bassett Dairy Rd Unit 380760, Monticello, FL 32344
- Land
- 420 Acres
- $7,119 per Acre
Last Sold Summary
- 5% Below List Price
- 87 Days On Market
Last Listing Agent Brian Proctor NAI TALCOR Commercial

0 Bassett Dairy Rd Unit 380760, Monticello, FL 32344

/18
Est $296,158 Not Listed For Sale
- 5 Beds
- 2 Baths
- 1,728 Sq Ft
622 Limestone Rd, Monticello, FL 32344

622 Limestone Rd, Monticello, FL 32344

/28
$57,056 Under Contract
- Land
- 6.37 Acres
- $8,957 per Acre
TBD S Salt Rd, Monticello, FL 32344

You can't hear your neighbors here - unless you count the hoot owls hooting! Extraordinary 6.37 acre homesite or recreational tract. This newly surveyed property offers the perfect blend of privacy, natural beauty and convenience. Featuring a mature forest of hardwoods and tall "long leaf" pines in a picturesque triangle shaped layout. The longest side (1070 ft) fronts S. Salt Road, giving over a

Lynette Sirmon

All Realty Services

(448) 334-2517

TBD S Salt Rd, Monticello, FL 32344
/17
$189,000 Sold Apr 02, 2025

485 Morris Rd, Monticello, FL 32344
- 3 Beds
- 2.5 Baths
- 2,525 Sq Ft
- Built 1960
Last Sold Summary
- 35% Below List Price
- $75/SF
- 233 Days On Market
Current Estimated Value $237,343

Last Listing Agent Susan Gillespie Lord & Stanley Realty, Inc.

485 Morris Rd, Monticello, FL 32344

/31
Est $153,073 Not Listed For Sale
- 3 Beds
821 Old Lloyd Rd Unit 2, Monticello, FL 32344

821 Old Lloyd Rd Unit 2, Monticello, FL 32344

/43
$295,000 Under Contract
- 5 Beds
- 2 Baths
- 3,320 Sq Ft
425 N Mulberry St, Monticello, FL 32344

Charming 1920's Two-Story Home in the Heart of Downtown Monticello, Fl. Step back in time with this beautiful home nestled on a spacious 1/2 acre lot in the heart of Monticello. Bursting with character and potential, this property is perfect for those looking to restore a classic Southern gem. Inside, you will find original, wood ceiling, floors , and walls that are just waiting to be brought

Pam Kelly

Kelly & Kelly Properties, Inc

(448) 222-3718

425 N Mulberry St, Monticello, FL 32344
/42
$425,000 Sold Feb 27, 2025

0 Fen Ct, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,807 Sq Ft
- Built 2025
Last Sold Summary
- $235/SF
- 6 Days On Market
Last Listing Agent Amber McKinney Hamilton Realty Advisors LLC

0 Fen Ct, Monticello, FL 32344

/5
Est $130,568 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,314 Sq Ft
220 Horseshoe Rd, Monticello, FL 32344

220 Horseshoe Rd, Monticello, FL 32344

/37
$365,000
- 3 Beds
- 2 Baths
- 2,766 Sq Ft
205 N Rhodes St, Monticello, FL 32344

Classic historical home built in the 1920's. Walking distance to charming downtown Monticello. Large covered front porch for kicking back and relaxing. Wood floors throughout, high ceiling and large open kitchen. This beauty boast over 2700 sf of heated and cooled living space. Beautiful entry into foyer with stairway leading to upstairs landing and two bedrooms. Formal living, formal dining and

Pam Kelly

Kelly & Kelly Properties, Inc

(448) 236-0470

205 N Rhodes St, Monticello, FL 32344
/41
$374,000 Sold Jan 21, 2026

226 Sutton, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
- Built 2024
Last Sold Summary
- 1% Below List Price
- $257/SF
- 3 Days On Market
Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

226 Sutton, Monticello, FL 32344

/34
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
336 Lake Rd, Monticello, FL 32344

336 Lake Rd, Monticello, FL 32344

/69
$555,000 New Construction
- 4 Beds
- 2 Baths
- 1,945 Sq Ft
64 Sanctuary Dr, Monticello, FL 32344

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

Chance Shutes

Keller Williams Town & Country

(448) 305-5882

64 Sanctuary Dr, Monticello, FL 32344
/26
$130,000 Sold Jul 25, 2025

00 Cardinal Ln, Monticello, FL 32344
- Land
- 14.1 Acres
- $9,220 per Acre
Last Sold Summary
- 8% Below List Price
- 175 Days On Market
Last Listing Agent Brenna Kelly-Ward Kelly & Kelly Properties, Inc

00 Cardinal Ln, Monticello, FL 32344

/30
Est $552,749 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,016 Sq Ft
3214 Tram Rd, Monticello, FL 32344

3214 Tram Rd, Monticello, FL 32344

/42
$725,000 New Construction
- 4 Beds
- 3.5 Baths
- 2,365 Sq Ft
81 Old Tung Grove Rd, Monticello, FL 32344

New Construction move in ready. Sacious over 2300 sq fr. with upstairs bonus room with bath and closet, could be 4th bedroom. 5.38 acre lot. Top of the lines finishes. Convenient to Tallahassee 15 minute drive.

Barry Kelly

Kelly & Kelly Properties, Inc

(448) 334-6582

81 Old Tung Grove Rd, Monticello, FL 32344
/40
$255,000 Sold Jun 30, 2025

185 Main St, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 2,206 Sq Ft
- Built 1914
Last Sold Summary
- 15% Below List Price
- $116/SF
- 93 Days On Market
Current Estimated Value $251,467

Last Listing Agent Lee Hall Capital City Real Estate Group

185 Main St, Monticello, FL 32344

/28
Est $445,037 Not Listed For Sale
- 3 Beds
- 2 Baths
- 3,328 Sq Ft
129 Indian Hills Rd, Monticello, FL 32344

129 Indian Hills Rd, Monticello, FL 32344

/19
$299,000
- Land
- 70.45 Acres
- $4,244 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
/2
$314,900 Sold May 08, 2025

2199 Old Lloyd Rd, Monticello, FL 32344
- 2 Beds
- 2 Baths
- 1,166 Sq Ft
- Built 1986
Last Sold Summary
- $270/SF
- 40 Days On Market
Current Estimated Value $607,909

Last Listing Agent Starbuck Rissman Steve C. Walker Realty, LLC

2199 Old Lloyd Rd, Monticello, FL 32344

/38
Est $164,847 Not Listed For Sale
- 2 Beds
- 1 Bath
- 912 Sq Ft
310 N Olive St, Monticello, FL 32344

310 N Olive St, Monticello, FL 32344

/14
$294,900 New Construction
- 3 Beds
- 2 Baths
- 1,351 Sq Ft
1090 Partridge Ln, Monticello, FL 32344

Currently under construction. Interior pictures are from a previous model home. Approximately 60 days until completion. Home qualifies for USDA financing.

Steve Walker Steve C. Walker Realty, LLC

1090 Partridge Ln, Monticello, FL 32344
/43
$263,000 Sold Jan 23, 2026

300 Cedar St, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 2,044 Sq Ft
- Built 1958
Last Sold Summary
- 5% Above List Price
- $129/SF
- 6 Days On Market
Last Listing Agent Jonathan Rigsby Spotlight Real Estate

300 Cedar St, Monticello, FL 32344

/36
Est $765,812 Not Listed For Sale
- 4 Beds
- 3 Baths
- 5,556 Sq Ft
250 Hiawatha Farms Rd, Monticello, FL 32344

250 Hiawatha Farms Rd, Monticello, FL 32344

/66
$1,125,000 Under Contract
- 3 Beds
- 1 Bath
- 1,146 Sq Ft
740 Kinsey Rd, Monticello, FL 32344

155 Acres in Jefferson County, Florida – Rolling Pastures & Country Charm Discover the perfect blend of natural beauty and peaceful living on this 155-acre property in scenic Jefferson County, Florida. Just 10 miles from downtown Monticello and 5 miles from I-10, this property offers both convenience and tranquility. Home- Built in 1941, featuring 1,146 square feet Thoughtfully updated while

Ben Jones Southern Land & Homes

740 Kinsey Rd, Monticello, FL 32344
/49
$615,000 Sold Dec 30, 2025

150 N Ojibwa Rd, Monticello, FL 32344
- 3 Beds
- 2.5 Baths
- 3,214 Sq Ft
- Built 2000
Last Sold Summary
- 10% Below List Price
- $191/SF
- 216 Days On Market
Last Listing Agent Hettie Spooner Hill Spooner & Elliott Inc

150 N Ojibwa Rd, Monticello, FL 32344

/28
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,323 Sq Ft
1993 Hartsfield Rd, Monticello, FL 32344

1993 Hartsfield Rd, Monticello, FL 32344

/3
$244,900 New Construction
- 2 Beds
- 2 Baths
- 1,092 Sq Ft
655 N Cherry St, Monticello, FL 32344

New construction in the heart of Monticello's Historic District! This beautifully built 1,092 sq ft off-grade home offers modern finishes while fitting seamlessly into the character of the neighborhood. The open floor plan features luxury vinyl plank flooring throughout, a stylish kitchen and stainless steel appliances, and quality craftsmanship from top to bottom. Bathrooms are finished with

Steve Walker Steve C. Walker Realty, LLC

655 N Cherry St, Monticello, FL 32344
/35
$375,000 Sold Jun 13, 2025

925 E Pearl St, Monticello, FL 32344
- 4 Beds
- 3.5 Baths
- 2,768 Sq Ft
- Built 1901
Last Sold Summary
- $135/SF
- 24 Days On Market
Current Estimated Value $382,242

Last Listing Agent Tom Grasberger Gaff's Realty Company

925 E Pearl St, Monticello, FL 32344

/42
Not Listed For Sale
52 Serenity Ln, Monticello, FL 32344

52 Serenity Ln, Monticello, FL 32344

/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
/34
$250,000 Sold Apr 17, 2025

194 Deer Run Rd, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,731 Sq Ft
- Built 1994
Last Sold Summary
- 17% Below List Price
- $144/SF
- 83 Days On Market
Current Estimated Value $274,354

Last Listing Agent Christopher Taylor Xcellence Realty

194 Deer Run Rd, Monticello, FL 32344

/7
Not Listed For Sale
0 Taylor Rd Unit 375808, Monticello, FL 32344

0 Taylor Rd Unit 375808, Monticello, FL 32344

/2
$244,900
- 3 Beds
- 2 Baths
- 1,235 Sq Ft
350 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

350 Bowman St, Monticello, FL 32344
/37
$416,000 Sold Feb 20, 2025

107 Tarn Way, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,806 Sq Ft
- Built 2024
Last Sold Summary
- 5% Below List Price
- $230/SF
- 46 Days On Market
Last Listing Agent Amber McKinney Hamilton Realty Advisors LLC

107 Tarn Way, Monticello, FL 32344

/3
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,623 Sq Ft
132 Hilltop Dr, Monticello, FL 32344

132 Hilltop Dr, Monticello, FL 32344

/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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