Jefferson County, FL Homes

/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
/29
$209,900 Sold Feb 11, 2026

2503 Rabon Rd, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,568 Sq Ft
- Built 1986
Last Sold Summary
- 14% Below List Price
- $134/SF
- 50 Days On Market
Last Listing Agent Clint Bailey Superior Realty Group LLC

2503 Rabon Rd, Monticello, FL 32344

/7
Not Listed For Sale

245 Whipporwill Rd, Monticello, FL 32344
245 Whipporwill Rd, Monticello, FL 32344

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

Last Listing Agent Molly Jenkins Coldwell Banker Hartung

/67
$995,000 Under Contract
- 4 Beds
- 4.5 Baths
- 3,696 Sq Ft
825 Rainey Run, Monticello, FL 32344

Set on 10 private acres, this exceptional estate offers a lifestyle defined by space, serenity, and effortless luxury. Surrounded by nature and bordered by a tranquil private creek, the property feels like a personal retreat—yet remains perfectly designed for modern living and entertaining. Inside, 3,696 square feet of light-filled living space unfolds with soaring ceilings, expansive windows,

Renee Dawkins Dawkins Realty LLC

825 Rainey Run, Monticello, FL 32344
/40
$520,000 Sold Aug 15, 2025

141 Shumard Ct, Monticello, FL 32344
- 3 Beds
- 3 Baths
- 2,661 Sq Ft
- Built 2021
Last Sold Summary
- 10% Below List Price
- $195/SF
- 241 Days On Market
Current Estimated Value $555,630

Last Listing Agent Kara Richetti Real Broker LLC

141 Shumard Ct, Monticello, FL 32344

/42
Est $573,627 Not Listed For Sale

257 Linton Place, Monticello, FL 32344
- 5 Beds
- 2.5 Baths
- 2,554 Sq Ft
- Built 1988
257 Linton Place, Monticello, FL 32344

Last Sold Summary
- 12% Above List Price
- $200/SF
- 90 Days On Market
Last Sold Price $510,000

Last Listing Agent Thomas Jacobs Coldwell Banker Hartung

/35
$650,000
- 3 Beds
- 2.5 Baths
- 2,239 Sq Ft
498 Heritage Blvd, Monticello, FL 32344

Welcome to this beautifully crafted 3-bedroom, 2.5-bath Craftsman-style home nestled in the highly sought-after Heritage Hills community. Perfectly positioned on a spacious 2.99-acre lot, this property offers the ideal blend of privacy, room to roam, and timeless curb appeal—all with an easy commute to both Tallahassee and Monticello. Step inside to an inviting open-concept living area designed

Brian Moser Bulldog Properties, LLC

498 Heritage Blvd, Monticello, FL 32344
/27
$80,000 Sold Aug 25, 2025

208 Robin Rd, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,144 Sq Ft
- Built 1980
Last Sold Summary
- 6% Below List Price
- $70/SF
- 7 Days On Market
Last Listing Agent Kimberly Nabors Nabors Realty LLC

208 Robin Rd, Monticello, FL 32344

/39
Not Listed For Sale

175 Main St, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,568 Sq Ft
- Built 2000
175 Main St, Monticello, FL 32344

Last Sold Summary
- $101/SF
- 43 Days On Market
Last Sold Price $159,000

Last Listing Agent Lee Hall Capital City Real Estate Group

/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
/28
$230,000 Sold Mar 05, 2026

44 Pine Needle Trace, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,234 Sq Ft
- Built 2004
Last Sold Summary
- 4% Below List Price
- $186/SF
- 107 Days On Market
Current Estimated Value $229,473

Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

44 Pine Needle Trace, Monticello, FL 32344

/4
Not Listed For Sale

TBD Lonnie, Monticello, FL 32344
TBD Lonnie, Monticello, FL 32344

Last Sold Summary
- 81 Days On Market
Last Sold Price $40,000

Last Listing Agent Moe Mossa Savvy Avenue, LLC

/18
$169,900 Under Contract
- 4 Beds
- 3 Baths
- 2,553 Sq Ft
34 W Hummingbird Ln, Monticello, FL 32344

New beautiful LVP flooring on mother in law suite side of the property and wdo repair underneath the new flooring!! So many options with this property!! It boasts 2 separate living spaces joined by a common family room. One side of the home has 1 bed and 1 bath, it's own kitchen and living space. The other side of the home has 3 bedrooms, 2 bathrooms and the kitchen and living area. The family

Susan Gillespie Lord & Stanley Realty, Inc.

34 W Hummingbird Ln, Monticello, FL 32344
/42
$449,000 Sold Apr 30, 2025

340 E Washington St, Monticello, FL 32344
- 3 Beds
- 3.5 Baths
- 3,635 Sq Ft
- Built 1842
Last Sold Summary
- $124/SF
- 80 Days On Market
Current Estimated Value $501,011

Last Listing Agent Sandy Ferrera All County Suncoast Property

340 E Washington St, Monticello, FL 32344

/25
Not Listed For Sale

50 Spruce Cir, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,601 Sq Ft
- Built 2024
50 Spruce Cir, Monticello, FL 32344

Last Sold Summary
- $185/SF
- 214 Days On Market
Last Sold Price $296,000

Last Listing Agent Tiffany Kasdorf Kozloski Realty, LLC

/24
$185,000
- 3 Beds
- 2.5 Baths
- 2,467 Sq Ft
490 E Palmer Mill Rd, Monticello, FL 32344

This striking Victorian home built in 1892 and located near downtown Monticello. The home features original hardwood pine floors, soaring 12-foot ceilings, a large bay window with bench seating (and storage) and several fireplaces. The master bathroom has been completely redone and complements the spacious master bedroom. The exterior of the home has a wraparound front deck, a rear screened

Van Drake Drake Realty, Inc.

490 E Palmer Mill Rd, Monticello, FL 32344
/2
$280,000 Sold Nov 04, 2025

665 W Washington St, Monticello, FL 32344
- 3 Beds
- 2.5 Baths
- 3,348 Sq Ft
- Built 1915
Last Sold Summary
- 7% Below List Price
- $84/SF
- 88 Days On Market
Current Estimated Value $309,542

Last Listing Agent Catherine Hope All Realty Services

665 W Washington St, Monticello, FL 32344

/10
Not Listed For Sale

VACANT Mahan Dr, Monticello, FL 32344
VACANT Mahan Dr, Monticello, FL 32344

Last Sold Summary
- 164 Days On Market
Last Sold Price $48,000

Last Listing Agent Catherine Hope All Realty Services

/11
$105,000
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
40 Westview Ln, Monticello, FL 32344

Being offered "AS IS" two separate 1 acre parcels combined 18-1N-4E-0108-000G-0030 & 18-1N-4E-0108-000G-0040 for a total of 2.01 acres. Don't judge this home by its exterior!! The outside siding shows significant deterioration, which is fully reflected in the price. However, once inside, you'll find a livable interior that's far more functional than first impressions suggest. This double-wide is

Alicia Radtke All Realty Services

40 Westview Ln, Monticello, FL 32344
/46
$190,000 Sold Sep 30, 2025

59 Westview Ln, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,430 Sq Ft
- Built 2021
Last Sold Summary
- 3% Below List Price
- $133/SF
- 27 Days On Market
Last Listing Agent Jason Glover Bulldog Properties, LLC

59 Westview Ln, Monticello, FL 32344

/41
Est $367,554 Not Listed For Sale

955 Still Rd, Monticello, FL 32344
- 3 Beds
- 2.5 Baths
- 3,302 Sq Ft
- Built 1990
955 Still Rd, Monticello, FL 32344

Last Sold Summary
- 47% Above List Price
- $76/SF
- 172 Days On Market
Last Sold Price $250,000

Last Listing Agent Renee Smawley Steve C. Walker Realty, LLC

/70
$700,000
- 3 Beds
- 2 Baths
- 2,400 Sq Ft
1627 Lloyd Creek Rd, Monticello, FL 32344

Enjoy the gorgeous water views from the porch of this like-new, 2022 built home! A Gated driveway leads to your 5 acre parcel on a beautiful 10 acre spring-fed lake with great fishing. 6 ft windows and 8x8 sliding doors allow the open living, dining, and kitchen areas to view the sunny outdoors. Kitchen features a large island with seating area, stainless appliances, gas stove, and fridge with

Nan Greynolds The Naumann Group Real Estate

1627 Lloyd Creek Rd, Monticello, FL 32344
/9
$43,000 Sold May 02, 2025

TBD Ashville Highlands Dr, Greenville, FL 32331
- Land
- 5.01 Acres
- $8,583 per Acre
Last Sold Summary
- 7% Below List Price
- 98 Days On Market
Last Listing Agent Grayson Boyd FL-GA Realty & Auction

TBD Ashville Highlands Dr, Greenville, FL 32331

/25
Not Listed For Sale

40 Spruce Cir, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,601 Sq Ft
- Built 2023
40 Spruce Cir, Monticello, FL 32344

Last Sold Summary
- $184/SF
- 186 Days On Market
Last Sold Price $295,000

Last Listing Agent Tiffany Kasdorf Kozloski Realty, LLC

/44
$615,000
- 4 Beds
- 5 Baths
- 3,862 Sq Ft
3873 N Jefferson St, Monticello, FL 32344

Stunning 4 Bedroom, 5 Bath Home on 9.73 Acres with Large Detached Garage plus Oversized Attached 2 Car Garage. Located just north of Monticello, this spacious 3,862 square foot home sits on 9.73 acres with a tranquil creek running through the rear of the property. The home is built on high and dry ground, and is not located in a flood zone or HOA. Built in 2007, the home features 10-foot

Stephanie Dobson Southern Land & Homes

3873 N Jefferson St, Monticello, FL 32344
/70
$455,000 Sold Mar 17, 2026

54 Woodland Dr, Monticello, FL 32344
- 4 Beds
- 3 Baths
- 2,032 Sq Ft
- Built 1977
Last Sold Summary
- 6% Below List Price
- $224/SF
- 60 Days On Market
Current Estimated Value $458,152

Last Listing Agent Lisa Carey Coldwell Banker Hartung

54 Woodland Dr, Monticello, FL 32344

/32
Not Listed For Sale

1262 NW Hawks Ave, Greenville, FL 32331
1262 NW Hawks Ave, Greenville, FL 32331

Last Sold Summary
- 152 Days On Market
Last Sold Price $220,000

Last Listing Agent Eddie Taylor EXP Realty, LLC

/3
$117,036
- Land
- 11.23 Acres
- $10,422 per Acre
Lot 29, Block A E Meadow Rd, Monticello, FL 32344

11.23 +/- acres at very end of East Meadow Road adjacent to 300+ acres owned by the Suwannee River Water Management District and nearby Aucilla River. Currently being used recreationally as a small hunting retreat by current owner. Additional connecting 9.4 +/- acres also available for purchase from same owner. Why not purchase both parcels and have 20 +/- acres all to yourself. These

Justin Peel Maclay Realty & Management LLC

Lot 29, Block A E Meadow Rd, Monticello, FL 32344
/40
$950,000 Sold Feb 25, 2026

193 Nautilus Dr, Monticello, FL 32344
- 4 Beds
- 6 Baths
- 9,848 Sq Ft
- Built 1987
Last Sold Summary
- 39% Below List Price
- $96/SF
- 281 Days On Market
Current Estimated Value $967,155

Last Listing Agent Ondrea Maldonado Hamilton Realty Advisors LLC

193 Nautilus Dr, Monticello, FL 32344

/21
Est $158,007 Not Listed For Sale

1060 Vista Rd, Monticello, FL 32344
- 3 Beds
- Built 2024
1060 Vista Rd, Monticello, FL 32344

Last Sold Summary
- 44% Above List Price
- $110,000/SF
- 37 Days On Market
Last Sold Price $110,000

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

/3
$97,964
- Land
- 9.4 Acres
- $10,422 per Acre
Lot 30, Block A E Meadow Rd, Monticello, FL 32344

9.4 +/- acres at very end of East Meadow Road and nearby Aucilla River. Currently being used recreationally as a small hunting retreat by current owner. Additional connecting 11.23 +/- acres also available for purchase from same owner. Why not purchase both parcels and have 20 +/- acres all to yourself. These opportunities don’t come along very often so don’t miss out.

Justin Peel Maclay Realty & Management LLC

Lot 30, Block A E Meadow Rd, Monticello, FL 32344
/4
$6,000 Sold Jul 08, 2025

TBD Hangar Ln, Greenville, FL 32331
- Land
- 0.25 Acre
- $24,000 per Acre
Last Sold Summary
- 25% Below List Price
- 91 Days On Market
Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc

TBD Hangar Ln, Greenville, FL 32331

/42
Est $607,191 Not Listed For Sale

456 Ridge Rd, Monticello, FL 32344
- 2 Beds
- 2.5 Baths
- 3,049 Sq Ft
- Built 2004
456 Ridge Rd, Monticello, FL 32344

Last Sold Summary
- 23% Above List Price
- $162/SF
- 34 Days On Market
Last Sold Price $495,000

Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

/60
$525,000 Under Contract
- 4 Beds
- 2 Baths
- 1,838 Sq Ft
965 Robert Thompson Rd, Monticello, FL 32344

Quiet country living near everything Tallahassee FL offers. Beautiful 4BR/2BA home on 5 acres. Split bedroom plan. Living room opens to large kitchen and breakfast nook. Sunroom not included in SqFt. Primary bedroom with tray ceilings, private bath with a jetted tub and separate shower. Plantation shutters throughout home. Generator installed 2017. 2 car attached garage and a large detached

Suzanne McGhee Mattox Realty, Inc

965 Robert Thompson Rd, Monticello, FL 32344
/27
$315,000 Sold Aug 22, 2025

395 W Palmer Mill Rd, Monticello, FL 32344
- 3 Beds
- 1.5 Baths
- 1,772 Sq Ft
- Built 1924
Last Sold Summary
- 3% Below List Price
- $178/SF
- 9 Days On Market
Last Listing Agent Mark Vollertsen Advanced Real Estate Sales

395 W Palmer Mill Rd, Monticello, FL 32344

/28
Not Listed For Sale

3360 Thompson Valley Rd, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,008 Sq Ft
- Built 1999
3360 Thompson Valley Rd, Monticello, FL 32344

Last Sold Summary
- $99/SF
- 94 Days On Market
Last Sold Price $100,000

Last Listing Agent Renee Smawley Steve C. Walker Realty, LLC

/50
$590,000 Under Contract
- 3 Beds
- 3 Baths
- 3,062 Sq Ft
185 Omega Dr, Monticello, FL 32344

Ranch-style equestrian property on 11.1 acres with a three stalls barn and crossed fence with water to all areas for easy pasture management and space for riding, grazing, and paddocks. Property features enclosed barn/workshop, covered equipment parking, utility sheds, and well area — ideal for tractors, trailers, feed, and tack storage. Main home offers 3BR/3BA with new flooring (Jan 2026),

Renee Glennon Coldwell Banker Hartung

185 Omega Dr, Monticello, FL 32344
/42
$320,000 Sold Oct 20, 2025

852 E Buckhorn Trail, Greenville, FL 32331
- 4 Beds
- 4 Baths
- 3,456 Sq Ft
- Built 1986
Last Sold Summary
- 16% Below List Price
- $93/SF
- 153 Days On Market
Last Listing Agent Lynette Sirmon All Realty Services

852 E Buckhorn Trail, Greenville, FL 32331

/41
Est $552,577 Not Listed For Sale

1113 Old Lloyd Rd, Monticello, FL 32344
- 4 Beds
- 4 Baths
- 2,834 Sq Ft
- Built 1984
1113 Old Lloyd Rd, Monticello, FL 32344

Last Sold Summary
- 7% Above List Price
- $182/SF
- 244 Days On Market
Last Sold Price $516,000

Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc

/35
$375,000
- 4 Beds
- 3.5 Baths
- 2,768 Sq Ft
925 E Pearl St, Monticello, FL 32344

Charming historic home with bonus guest cottage, located on the most beautiful oak lined street in picturesque Monticello, Florida. OWNER FINANCING AVAILABLE call for convenient terms. Enjoy small-town living in this updated home featuring a 2020 Roof, 2022 HVAC, 2025 Water Heater, Updated Electrical, CPVC and Copper Plumbing, Schedule 40 sewer piping, and mostly updated windows. New mini split

Tom Grasberger Gaff's Realty Company

925 E Pearl St, Monticello, FL 32344

Showing Results 281 - 320, Page 8 of 18

Florida Jefferson County

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Jefferson County, FL Homes

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