Jefferson County, FL Homes

/54
$525,000 Under Contract
- 4 Beds
- 3 Baths
- 2,784 Sq Ft
70 Generation Ct, Monticello, FL 32344

Wow! Special opportunity to add your personal touches! Design your dream kitchen! Craftsman style home features a roomy floorplan with lots of storage nooks and crannies, huge primary suite waiting for your perfect finishes, open kitchen and all nestled on private 4.45 acres. Many of the are there to finish trim, there’s extra stone and extra tile. LVP and ceramic tile flooring throughout home,

Lee Duggar Re/Max Professionals Realty

70 Generation Ct, Monticello, FL 32344
/9
$42,000 Sold Feb 26, 2026

50 E Pinhook Rd, Monticello, FL 32344
- Land
- 1.58 Acres
- $26,582 per Acre
Last Sold Summary
- 11% Above List Price
- 3 Days On Market
Last Listing Agent Heather Boyd FL-GA Realty & Auction

50 E Pinhook Rd, Monticello, FL 32344

/31
Not Listed For Sale

112 Rudolph Ln, Monticello, FL 32344
- 4 Beds
- 2 Baths
- 2,112 Sq Ft
- Built 2022
112 Rudolph Ln, Monticello, FL 32344

Last Sold Summary
- $114/SF
- 68 Days On Market
Last Sold Price $240,000

Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

/58
$725,000 Under Contract
- 4 Beds
- 3 Baths
- 2,663 Sq Ft
296 Hunter Ridge, Monticello, FL 32344

Situated on 5 gorgeous acres in Monticello, Florida, this property is the epitome of privacy and modern farmhouse living. Built in 2021, this beautiful 4BR/3BA home also features a 36x30 detached workshop complete with electricity. Step inside to find a spacious office just off the foyer and a light-filled living room featuring a 10-foot lit tray ceiling and a stunning fireplace with built-ins

Hettie Spooner Hill Spooner & Elliott Inc

296 Hunter Ridge, Monticello, FL 32344
/35
$325,000 Sold Nov 25, 2025

1530 Sweetbay Ct, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,370 Sq Ft
- Built 2021
Last Sold Summary
- $237/SF
- 58 Days On Market
Current Estimated Value $334,512

Last Listing Agent Chance Shutes Keller Williams Town & Country

1530 Sweetbay Ct, Monticello, FL 32344

/4
Not Listed For Sale

TBD Blackberry Tr, Monticello, FL 32344
TBD Blackberry Tr, Monticello, FL 32344

Last Sold Summary
- 38 Days On Market
Last Sold Price $49,250

Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc

/3
$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
/42
$193,000 Sold Jul 02, 2025

285 E 10th Way, Greenville, FL 32331
- 4 Beds
- 2 Baths
- 2,088 Sq Ft
- Built 2015
Last Sold Summary
- 4% Above List Price
- $92/SF
- 30 Days On Market
Current Estimated Value $200,948

Last Listing Agent Michael Phillips Engel & Völkers Tallahassee

285 E 10th Way, Greenville, FL 32331

/4
Not Listed For Sale

XXXX St Augustine Rd Parcel #2, Monticello, FL 32344
XXXX St Augustine Rd Parcel #2, Monticello, FL 32344

Last Sold Summary
- 38 Days On Market
Last Sold Price $135,000

Last Listing Agent Hines Boyd FL-GA Realty & Auction

/52
$449,000
- 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 room to 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 entry—one used as a

Rachel Sparling All Realty Services

930 E Pearl St, Monticello, FL 32344
/3
$244,900 Sold Mar 21, 2026

655 N Cherry St, Monticello, FL 32344
- 2 Beds
- 2 Baths
- 1,092 Sq Ft
- Built 2026
Last Sold Summary
- $224/SF
- 35 Days On Market
Last Listing Agent Steve Walker Steve C. Walker Realty, LLC

655 N Cherry St, Monticello, FL 32344

/20
Not Listed For Sale

VACANT W 3rd Way, Greenville, FL 32331
VACANT W 3rd Way, Greenville, FL 32331

Last Sold Summary
- 103 Days On Market
Last Sold Price $63,750

Last Listing Agent Catherine Hope All Realty Services

/44
$420,000 Under Contract
- 5 Beds
- 2 Baths
- 2,324 Sq Ft
40 W Cavallo Trail, Monticello, FL 32344

Beautiful 5BR/2BA home on 3.13 fully fenced acres in Jefferson County, just minutes from Monticello. Built in 2006, this property blends modern comfort with horse-ready potential and includes a horse barn/stable and fencing. Fresh interior paint highlights a spacious layout featuring a cozy fireplace, dedicated laundry room, and a private primary suite with a large soaking tub and separate

Joyce Gardner Signature Realty Professionals

40 W Cavallo Trail, Monticello, FL 32344
/2
$160,000 Sold Apr 17, 2025

288 Forest Dr, Monticello, FL 32344
- 2 Beds
- 2 Baths
- 990 Sq Ft
- Built 2020
Last Sold Summary
- 6% Below List Price
- $162/SF
- 165 Days On Market
Last Listing Agent Starbuck Rissman Steve C. Walker Realty, LLC

288 Forest Dr, Monticello, FL 32344

/41
Not Listed For Sale

660 Whispering Hill, Monticello, FL 32344
- 3 Beds
- 2.5 Baths
- 2,160 Sq Ft
- Built 2000
660 Whispering Hill, Monticello, FL 32344

Last Sold Summary
- $309/SF
- 31 Days On Market
Last Sold Price $667,000

Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

/70
$425,000
- 3 Beds
- 2.5 Baths
- 3,126 Sq Ft
1628 N Jefferson St, Monticello, FL 32344

BACK ON MARKET | IMPROVED PRICE: $425,000 1628 North Jefferson Hwy | 4 BR / 2 1/2 BA | 3,126 SQ FT | 1.5 ACRES Experience the perfect harmony of peaceful living and professional potential. Now offered at an improved price of $425,000, this expansive residence sits atop 1.5 acres of gorgeous landscape, offering a rare blend of space, serenity, and strategic location. The Highlights: ? Spacious

Jennifer Ward Century 21 First Story

1628 N Jefferson St, Monticello, FL 32344
/42
$390,000 Sold Jun 26, 2025

1288 Indian Hills Rd, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,917 Sq Ft
- Built 1987
Last Sold Summary
- 8% Below List Price
- $203/SF
- 140 Days On Market
Current Estimated Value $443,379

Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

1288 Indian Hills Rd, Monticello, FL 32344

/11
Not Listed For Sale

XXX Parcel #3 St Augustine Rd, Monticello, FL 32344
XXX Parcel #3 St Augustine Rd, Monticello, FL 32344

Last Sold Summary
- 31 Days On Market
Last Sold Price $184,440

Last Listing Agent Hines Boyd FL-GA Realty & Auction

/37
$469,000
- 4 Beds
- 2 Baths
- 2,624 Sq Ft
1142 Ashville Highlands, Greenville, FL 32331

Nestled in the peaceful Ashville Highlands fly-in community, this custom 2600+ sq. ft. all-brick home offers space, privacy and quality construction 15 min east of Monticello. Built with insulated concrete form walls and a metal roof, the home is designed for durability and comfort. The five acre property includes a 24x24 metal outbuilding/garage, generator, 50 amp RV plug-in and parking, and

Jennifer Lee Armor Realty, Inc

1142 Ashville Highlands, Greenville, FL 32331
/27
$210,000 Sold Oct 20, 2025

140 E Buckhorn Trail, Greenville, FL 32331
- 3 Beds
- 2 Baths
- 1,560 Sq Ft
- Built 2004
Last Sold Summary
- 16% Below List Price
- $135/SF
- 101 Days On Market
Current Estimated Value $225,378

Last Listing Agent Christopher Worth Keller Williams Town & Country

140 E Buckhorn Trail, Greenville, FL 32331

/11
Not Listed For Sale

xxx St Augustine Parcel #4 Rd, Monticello, FL 32344
xxx St Augustine Parcel #4 Rd, Monticello, FL 32344

Last Sold Summary
- 0 Days On Market
Last Sold Price $202,500

Last Listing Agent Hines Boyd FL-GA Realty & Auction

/19
$480,000 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
/14
$168,100 Sold Nov 17, 2025

375 Maple St, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,716 Sq Ft
- Built 1920
Last Sold Summary
- 11% Below List Price
- $98/SF
- 70 Days On Market
Current Estimated Value $177,432

Last Listing Agent Caleb Stephens Silo Hill Properties

375 Maple St, Monticello, FL 32344

/40
Est $520,608 Not Listed For Sale

9255 Gamble Rd, Monticello, FL 32344
- 2 Beds
- 3 Baths
- 1,833 Sq Ft
- Built 1970
9255 Gamble Rd, Monticello, FL 32344

Last Sold Summary
- 8% Above List Price
- $262/SF
- 5 Days On Market
Last Sold Price $480,000

Last Listing Agent Alicia Radtke All Realty Services

/47
$295,000 Under Contract
- 3 Beds
- 1.5 Baths
- 1,834 Sq Ft
575 W Madison St, Monticello, FL 32344

Perfectly located just around the corner from downtown Monticello, this charming 1950s brick home is ready for its next owners! Step inside to find a desirable split floor plan, beautifully maintained new hardwood floors, a cozy wood-burning fireplace, and an updated kitchen featuring newer stainless steel appliances. The spacious half bath offers plumbing already in place to easily convert it

Brooke Feld Keller Williams Town & Country

575 W Madison St, Monticello, FL 32344
/7
$95,000 Sold Aug 01, 2025

0 Taylor Rd Unit 384618, Monticello, FL 32344
- Land
- 5.17 Acres
- $18,375 per Acre
Last Sold Summary
- 21% Below List Price
- 102 Days On Market
Last Listing Agent Kevin Davis The Naumann Group Real Estate

0 Taylor Rd Unit 384618, Monticello, FL 32344

/4
Not Listed For Sale

XXX Shiver, Monticello, FL 32344
XXX Shiver, Monticello, FL 32344

Last Sold Summary
- 204 Days On Market
Last Sold Price $29,500

Last Listing Agent Hines Boyd FL-GA Realty & Auction

/8
$450,000
- Land
- 85.26 Acres
- $5,278 per Acre
0 Big Joe Rd Unit 2025007616, 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.

Florie Gage Cornerstone Coastal Properties

0 Big Joe Rd Unit 2025007616, Monticello, FL 32344
/10
$220,000 Sold Aug 26, 2025

1400 Gamble Rd, Monticello, FL 32344
- Land
- 7 Acres
- $31,429 per Acre
Last Sold Summary
- 6% Below List Price
- 119 Days On Market
Current Estimated Value $232,412

Last Listing Agent Kenneth Ayers Primesouth Fezler, Russell and

1400 Gamble Rd, Monticello, FL 32344

/24
Not Listed For Sale

00 Valley View Rd, Monticello, FL 32344
00 Valley View Rd, Monticello, FL 32344

Last Sold Summary
- 42 Days On Market
Last Sold Price $271,000

Last Listing Agent Brenna Kelly-Ward Kelly & Kelly Properties, Inc

/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
/5
$49,000 Sold Feb 16, 2026

4618 E Capps Hwy, Lamont, FL 32336
- 4 Beds
- 1 Bath
- 1,232 Sq Ft
- Built 1940
Last Sold Summary
- 25% Below List Price
- $40/SF
- 247 Days On Market
Current Estimated Value $78,871

Last Listing Agent Nelda Parker-Pace Sawgrass Realty, LLC

4618 E Capps Hwy, Lamont, FL 32336

/17
Not Listed For Sale

188 Fallow Rd, Lamont, FL 32336
- 3 Beds
- 2 Baths
- 1,624 Sq Ft
- Built 2005
188 Fallow Rd, Lamont, FL 32336

Last Sold Summary
- $169/SF
- 34 Days On Market
Last Sold Price $275,000

Last Listing Agent Brian Bachman Kelly & Kelly Properties, Inc

/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
/42
$165,000 Sold Feb 27, 2026

2436 N Jefferson Hwy, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 2,390 Sq Ft
- Built 1951
Last Sold Summary
- 38% Below List Price
- $69/SF
- 285 Days On Market
Current Estimated Value $260,957

Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

2436 N Jefferson Hwy, Monticello, FL 32344

/14
Est $431,963 Not Listed For Sale

4131 Ashville Hwy, Monticello, FL 32344
- 2 Beds
- Built 1940
4131 Ashville Hwy, Monticello, FL 32344

Last Sold Summary
- 15% Above List Price
- $363/SF
- 16 Days On Market
Last Sold Price $375,000

Last Listing Agent Sarah Scott Coldwell Banker Hartung

/16
$65,000
- 2 Beds
- 1 Bath
- 888 Sq Ft
980 Mays St, Monticello, FL 32344

"Buy Now and Wait" a little while the attorney finishes up the Probate proceedings underway. Cannot close until court approval however you can go ahead and grab it now. Concrete Block 2/1 Home less than a mile from downtown Monticello! This quaint 888 sq ft home sits under a metal roof and only requires your vision and a little effort to become a superb starter home or investment opportunity.

Ben Marinelli All Realty Services

980 Mays St, Monticello, FL 32344
/14
$26,000 Sold Jan 29, 2026

3C Hanger Ln, Greenville, FL 32331
- Land
- 0.09 Acre
- $288,889 per Acre
Last Sold Summary
- 33% Below List Price
- 172 Days On Market
Last Listing Agent Esther Warrendorf Canopy Road Realty

3C Hanger Ln, Greenville, FL 32331

/2
Not Listed For Sale

B Salt Rd, Monticello, FL 32344
B Salt Rd, Monticello, FL 32344

Last Sold Summary
- 86 Days On Market
Last Sold Price $835,000

Last Listing Agent Sherry Shaheen ENGEL & VOLKERS GAINESVILLE

/22
$95,000
- 3 Beds
- 2 Baths
- 1,125 Sq Ft
295 W J Hatchett Rd, Lamont, FL 32336

Investor special with great potential! Situated on approximately .75 acres in Jefferson County, this 2022 mobile home offers a fantastic opportunity for the right buyer to complete the final steps and make it their own. Conveniently located just minutes from I-10 for easy access to Tallahassee and only about 10 minutes to downtown Monticello, the property combines rural space with excellent

Catherine Hope All Realty Services

295 W J Hatchett Rd, Lamont, FL 32336

Showing Results 161 - 200, Page 5 of 18

Florida Jefferson County

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Jefferson County, FL Homes

Real Estate & Homes