Jefferson County, FL Homes

/19
$460,000

New Construction $15K 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
/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
Current Estimated Value $258,321

Last Listing Agent Jonathan Rigsby Spotlight Real Estate

300 Cedar St, Monticello, FL 32344

/3
Not Listed For Sale

132 Hilltop Dr, Monticello, FL 32344
- 3 Beds
- 2.5 Baths
- 2,623 Sq Ft
- Built 2021
132 Hilltop Dr, Monticello, FL 32344

Last Sold Summary

/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
/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
Current Estimated Value $612,401

Last Listing Agent Hettie Spooner Hill Spooner & Elliott Inc

150 N Ojibwa Rd, Monticello, FL 32344

/17
Not Listed For Sale

360 Poppell Cemetery Rd, Lamont, FL 32336
360 Poppell Cemetery Rd, Lamont, FL 32336

Last Sold Summary
- 6 Days On Market

/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
/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 $398,666

Last Listing Agent Tom Grasberger Gaff's Realty Company

925 E Pearl St, Monticello, FL 32344

/17
Not Listed For Sale

000 Clark Rd, Monticello, FL 32344
000 Clark Rd, Monticello, FL 32344

Last Sold Summary
- 135 Days On Market

/57
$589,900

Under Contract
- 4 Beds
- 3 Baths
- 2,660 Sq Ft
513 Creekside Ct, Monticello, FL 32344

HOME HAS BRAND NEW LUXURY PLANK VINYL~ Custom home built by Kessler Construction on 2 full acres in desirable Crook Creek subdivision~4 bedrooms/3 full baths~gourmet kitchen~split bedroom plan~luxury master bath~incredibly high ceilings~42x14 screened porch~oversized 2-car garage~located on a cul-de-sac, this home offers peaceful privacy

Renee Smawley Steve C. Walker Realty, LLC

513 Creekside Ct, Monticello, FL 32344
/58
$710,000

Sold May 26, 2026

296 Hunter Ridge, Monticello, FL 32344
- 4 Beds
- 3 Baths
- 2,663 Sq Ft
- Built 2021
Last Sold Summary
- 2% Below List Price
- $267/SF
- 10 Days On Market
Current Estimated Value $663,464

Last Listing Agent Hettie Spooner Hill Spooner & Elliott Inc

296 Hunter Ridge, 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
- 68 Days On Market

/42
$469,997

New Construction
- 3 Beds
- 2 Baths
- 1,890 Sq Ft
51 Tarn Way, Monticello, FL 32344

MOVE IN READY!! Amazing new construction 3 bedroom 2 bathroom plus office. Luxurious master suite, Kitchen made of dreams, this is a must see!

Amber McKinney Hamilton Realty Advisors LLC

51 Tarn Way, Monticello, FL 32344
/34
$437,000

Sold Jul 07, 2025

327 Kims Ln, Lamont, FL 32336
- 3 Beds
- 2 Baths
- 2,472 Sq Ft
- Built 2014
Last Sold Summary
- $177/SF
- 19 Days On Market
Current Estimated Value $437,981

Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc

327 Kims Ln, Lamont, FL 32336

/4
Not Listed For Sale

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

Last Sold Summary
- 38 Days On Market

/52
$425,000

$24K 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
/31
$675,000

Sold Oct 28, 2025

17 Old Tung Grove Rd, Monticello, FL 32344
- 3 Beds
- 2.5 Baths
- 2,344 Sq Ft
- Built 2024
Last Sold Summary
- 3% Below List Price
- $288/SF
- 635 Days On Market
Current Estimated Value $657,568

Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc

17 Old Tung Grove Rd, Monticello, FL 32344

/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

/70
$410,000
- 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
/33
$186,000

Sold Nov 21, 2025

1065 S Mulberry St, Monticello, FL 32344
- 2 Beds
- 2 Baths
- 1,356 Sq Ft
- Built 1927
Last Sold Summary
- 2% Below List Price
- $137/SF
- 65 Days On Market
Current Estimated Value $198,032

Last Listing Agent Katherine Gonzalez Pearson Realty Inc.

1065 S Mulberry 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

/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
/28
$202,000

Sold Oct 20, 2025

85 Pine Cone Dr, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,678 Sq Ft
- Built 2002
Last Sold Summary
- 4% Below List Price
- $120/SF
- 17 Days On Market
Current Estimated Value $213,497

Last Listing Agent Gabriela Sacco All Realty Services

85 Pine Cone Dr, 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

/37
$469,000

$20K PRICE DROP
- 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 CONSULTANTS TO HOMEBUI

1142 Ashville Highlands, Greenville, FL 32331
/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

/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

/19
$157,000
- Land
- 10.54 Acres
- $14,896 per Acre
XX Ridge Rd, Monticello, FL 32344

Leave Urbana and breathe... 10.54 acres in Exclusive Casa Bianca Ridge. Beautiful, rare lot on which to build your dream home. There is room to create a multi-generational paradise or your own personal playground. Nicely wooded parcel with a gentle stream deeper into the property. Very private. Survey in associated docs. Move quickly. Gate at Driveway. Do not enter the property without approval.

Nicholas Harrington Keller Williams Town & Country

XX Ridge Rd, 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 $329,874

Last Listing Agent Chance Shutes Keller Williams Town & Country

1530 Sweetbay Ct, Monticello, FL 32344

/40
Est $532,097

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
- 5 Days On Market

/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
/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 $204,456

Last Listing Agent Michael Phillips Engel & Völkers Tallahassee

285 E 10th Way, Greenville, FL 32331

/4
Not Listed For Sale

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

Last Sold Summary
- 204 Days On Market

/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
/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

/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

/3
$258,900

New Construction Under Contract
- 2 Beds
- 2 Baths
- 1,092 Sq Ft
660 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

660 N Cherry 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 $426,966

Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

1288 Indian Hills Rd, Monticello, FL 32344

/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
- 34 Days On Market

/34
$185,000
- 2 Beds
- 1 Bath
- 800 Sq Ft
28 Kameron Dr, Monticello, FL 32344

Brand New Inside! 1-Acre Modern Retreat Just Minutes from the City. Enjoy the ultimate "new home" experience without the wait! This 2-bedroom, 1-bathroom gem at 28 Kameron Dr has been completely transformed with a brand new interior, offering high-end laminate flooring, fresh paint, and modern finishes throughout. Situated on a sprawling, level 1-acre lot, you’ll enjoy total privacy and room to

Chip Williams Keller Williams Town & Country

28 Kameron Dr, Monticello, FL 32344

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Florida Jefferson County

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Jefferson County, FL Homes

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