Jefferson County, FL Homes

/24
Not Listed For Sale
00 Valley View Rd, Monticello, FL 32344

00 Valley View Rd, Monticello, FL 32344

/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
/35
$541,500 Sold Mar 27, 2025

129 White Oak Dr, Monticello, FL 32344
- 4 Beds
- 2 Baths
- 1,945 Sq Ft
- Built 2024
Last Sold Summary
- $278/SF
- 67 Days On Market
Last Listing Agent Marshall Gibbs Capital City Real Estate Group

129 White Oak Dr, Monticello, FL 32344

/17
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,624 Sq Ft
188 Fallow Rd, Lamont, FL 32336

188 Fallow Rd, Lamont, FL 32336

/70
$599,900 Under Contract
- 4 Beds
- 2.5 Baths
- 2,776 Sq Ft
529 Valley View Trail, Monticello, FL 32344

Rare Find! Wonderful 4 Bedroom/2.5 Bathroom Home on over 5 Fenced & Gated Acres with Horse Stable/Barn, a 30x32 workshop w/Garage Door that has Mother-In Law Suite/Guest House potential, as well as an 8x16 greenhouse and a Custom Built 14x28 Jack and Jill Storage shed with loft and workbench on the property. Located just off East Mahan Drive/Highway 90, you can truly live in the country and still

Liz Kuntz Keller Williams Town & Country

529 Valley View Trail, 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 $190,488

Last Listing Agent Michael Phillips Engel & Völkers Tallahassee

285 E 10th Way, Greenville, FL 32331

/14
Est $427,122 Not Listed For Sale
- 2 Beds
4131 Ashville Hwy, Monticello, FL 32344

4131 Ashville Hwy, Monticello, FL 32344

/61
$589,900
- 4 Beds
- 3 Baths
- 2,660 Sq Ft
513 Creekside Ct, Monticello, FL 32344

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
/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

/2
Not Listed For Sale
B Salt Rd, Monticello, FL 32344

B Salt Rd, Monticello, FL 32344

/38
$599,900 New Construction
- 3 Beds
- 2.5 Baths
- 2,134 Sq Ft
261 Hiawatha Farms S, Monticello, FL 32344

Welcome to this stunning new construction masterpiece, meticulously designed and built by the esteemed Kasdorf Homes, LLC. This craftsman beauty is awaiting its first owners and will be ready for occupancy by the beginning of May. Spanning an impressive 2134 square feet, this home offers a spacious and open concept floor plan, perfect for modern living. The split floor plan provides privacy and

Ross Kozloski Kozloski Realty, LLC

261 Hiawatha Farms S, 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 $402,351

Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

1288 Indian Hills Rd, Monticello, FL 32344

/2
Not Listed For Sale
A Salt Rd, Monticello, FL 32344

A Salt Rd, Monticello, FL 32344

/5
$75,000
- Land
- 5 Acres
- $15,000 per Acre
200 Samanthas Ln, Monticello, FL 32344

Rare opportunity to own 5± acres on Aucilla Road. This beautiful property features planted pines and offers a blank canvas with endless possibilities for a future homesite, no restrictions! Conveniently located near Monticello and Aucilla Christian Academy, only 8 minutes from I-10 and 30 minutes from Tallahassee. 5 +/- acres — exact acreage to be determined by survey during contract period.

Allison Smith OaksFeather Realty

200 Samanthas Ln, Monticello, FL 32344
/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 $215,354

Last Listing Agent Christopher Worth Keller Williams Town & Country

140 E Buckhorn Trail, Greenville, FL 32331

/37
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,976 Sq Ft
185 White Oak Dr, Monticello, FL 32344

185 White Oak Dr, Monticello, FL 32344

/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
/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
Last Listing Agent Caleb Stephens Silo Hill Properties

375 Maple St, Monticello, FL 32344

/22
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,351 Sq Ft
390 Elliot Dr, Monticello, FL 32344

390 Elliot Dr, Monticello, FL 32344

/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.

Starbuck Rissman Steve C. Walker Realty, LLC

1 W Meadow Rd, 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

/42
Est $636,274 Not Listed For Sale
- 6 Beds
- 4 Baths
- 3,998 Sq Ft
12840 Gamble Rd, Monticello, FL 32344

12840 Gamble Rd, 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
/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 $219,787

Last Listing Agent Kenneth Ayers Primesouth Fezler, Russell and

1400 Gamble Rd, Monticello, FL 32344

/38
Est $222,735 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,276 Sq Ft
5118 E Washington Hwy, Monticello, FL 32344

5118 E Washington Hwy, Monticello, FL 32344

/4
$135,000 Under Contract
- Land
- 5 Acres
- $27,000 per Acre
276 E Blue Bird Rd, Monticello, FL 32344

Beautiful home sight in a quiet neighborhood. Fence and have animals

S.W. Ellis Blue Bird Homes & Lands

276 E Blue Bird Rd, 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

/5
Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,128 Sq Ft
271 Tecumseh Rd, Monticello, FL 32344

271 Tecumseh Rd, Monticello, FL 32344

/19
$135,000 Under Contract
- Land
- 5.25 Acres
- $25,714 per Acre
XX Foggy Ln, Monticello, FL 32344

Hard to find vacant land opportunity in charming Monticello - 5.25 acres. Extremely private, tucked away from the hustle and bustle of the larger city life. Surrounded by parks, trails, and lakes. Wildlife and nature right at your doorstep. Take advantage of this deal, build instant equity, and enjoy the privacy on this 5.25 acre parcel.

Cole Davis The Naumann Group Real Estate

XX Foggy Ln, Monticello, FL 32344
/3
$94,500 Sold Sep 05, 2025

0 W Osprey Ln Unit 381026, Monticello, FL 32344
- Land
- 20 Acres
- $4,725 per Acre
Last Sold Summary
- 32% Below List Price
- 222 Days On Market
Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

0 W Osprey Ln Unit 381026, Monticello, FL 32344

/5
Not Listed For Sale
0 W Osprey Ln, Monticello, FL 32344

0 W Osprey Ln, Monticello, FL 32344

/11
$22,500
- Land
- 2 Acres
- $11,250 per Acre
0 Flatwoods, Monticello, FL 32344

Land for Sale – Flatwoods, FL 32344. Size: 2.0 Acres. Location: Flatwoods Road, Monticello, Florida 32344. Property Highlights: Buildable lot with plenty of space; Power available on the road; 411.75 feet of road frontage; Peaceful rural setting surrounded by large parcels; No HOA – flexible use for site-built or modular homes. About 40 minutes to Tallahassee. Ideal for a private

Andrey Rossin CASH FLOW IN MIAMI REALTY

0 Flatwoods, Monticello, FL 32344
/41
$336,000 Sold Jun 23, 2025

1600 Sweetbay Ct, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,555 Sq Ft
- Built 2021
Last Sold Summary
- $216/SF
- 33 Days On Market
Last Listing Agent Amber Renaud The Nova Group Realty

1600 Sweetbay Ct, Monticello, FL 32344

/16
Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,801 Sq Ft
157 White Oak Dr, Monticello, FL 32344

157 White Oak Dr, Monticello, FL 32344

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

Probate proceedings underway. Cannot close until court approval. Concrete Block 2/1 Home less than a mile from downtown Monticello! This quaint 888sqft home sits under a metal roof and only requires your vision and a little effort to become a superb starter home or investment opportunity. Property is fully fenced and on city utilities. Room measurements are approximate

Ben Marinelli All Realty Services

980 Mays St, Monticello, FL 32344
/33
$140,000 Sold Jan 09, 2026

720A Indian Hills Rd, Monticello, FL 32344
- Land
- 10.62 Acres
- $13,183 per Acre
Last Sold Summary
- 26% Below List Price
- 131 Days On Market
Last Listing Agent Alicia Radtke All Realty Services

720A Indian Hills Rd, Monticello, FL 32344

/39
Est $577,644 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,700 Sq Ft
210 Deer Run, Monticello, FL 32344

210 Deer Run, Monticello, FL 32344

/24
$189,900
- 3 Beds
- 2 Baths
- 1,440 Sq Ft
963 Quail Ln, Monticello, FL 32344

Great location for this property in Lloyd Acres. The property has 2.26 acres of partially wooded area. The property consists of the single family home, detached garage/carport/workshop and a singlewide mobile home. The vinyl sided home will need some repair and updating but has tremendous potential. The detached garage is large with 2 stalls. The mobile home is in need of a total renovation (or

Van Drake Drake Realty, Inc.

963 Quail Ln, Monticello, FL 32344
/63
$500,000 Sold Oct 24, 2025

282 Long Leaf Dr, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 2,170 Sq Ft
- Built 1998
Last Sold Summary
- 4% Below List Price
- $230/SF
- 95 Days On Market
Current Estimated Value $492,741

Last Listing Agent Catherine Hope All Realty Services

282 Long Leaf Dr, Monticello, FL 32344

/41
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,560 Sq Ft
927 Quail Ln, Monticello, FL 32344

927 Quail Ln, Monticello, FL 32344

Showing Results 161 - 200, Page 5 of 18

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