Monticello, FL Homes

/31
$277,000
- 3 Beds
- 2 Baths
- 1,740 Sq Ft
104 Pine Cone Dr, Monticello, FL 32344

This gorgeous, 3-bedroom, 2-bath modular home, recently renovated by Paul Davis, combines modern comfort and style. Inside, you’ll find an open floor plan, a brand-new kitchen with granite countertops, new appliances, and updated finishes that make everyday living and entertaining a joy. The primary bedroom offers a luxurious ensuite with double vanities, a walk-in shower, and garden tub, as well

Trevor Ann Clark Keller Williams Town & Country

104 Pine Cone Dr, Monticello, FL 32344
/55
$1,035,000 Sold Oct 15, 2025

1165 Dills Rd, Monticello, FL 32344
- 5 Beds
- 5.5 Baths
- 4,700 Sq Ft
- Built 2002
Last Sold Summary
- 6% Below List Price
- $220/SF
- 54 Days On Market
Current Estimated Value $1,031,662

Last Listing Agent Callie Rhoads The Naumann Group Real Estate

1165 Dills Rd, Monticello, FL 32344

/13
Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,320 Sq Ft
56 Ward Rd, Monticello, FL 32344

56 Ward Rd, Monticello, FL 32344

/70
$1,325,000
- 5 Beds
- 4.5 Baths
- 5,476 Sq Ft
221 Kiley Dr, Monticello, FL 32344

Welcome to 221 Kiley Road in Monticello, Florida — a rare estate where vineyard charm, equestrian living, and exceptional space come together to create an unforgettable lifestyle. This 5-bedroom, 3.5-bathroom estate is a true masterpiece, gracefully set on 5 private acres and complemented by a beautiful pool house with an additional bathroom. An additional adjoining 5-acre parcel is also

Wilda Sigler Keller Williams Town & Country

221 Kiley Dr, Monticello, FL 32344
/29
$273,695 Sold Nov 26, 2025

9497 Gamble Rd, Monticello, FL 32344
- 2 Beds
- 2 Baths
- 1,404 Sq Ft
- Built 1995
Last Sold Summary
- 7% Below List Price
- $195/SF
- 128 Days On Market
Last Listing Agent Trevor Ann Clark Keller Williams Town & Country

9497 Gamble Rd, Monticello, FL 32344

/5
Not Listed For Sale
xx Landfill Rd, Monticello, FL 32344

xx Landfill Rd, Monticello, FL 32344

/55
$165,000 Under Contract
- 2 Beds
- 2 Baths
- 1,096 Sq Ft
1515 Tennessee Ave, Monticello, FL 32344

Brimming with rustic charm, this 2 bedroom, 2 bathroom home sits on .29 acres just outside Monticello, FL giving you the peace of county living with lower taxes and the convenience of a quick drive into town. Inside, the 1,096sqft layout features inviting wood paneling throughout, with updates to the guest bathroom, a full electrical rewire and new water line and cozy spaces filled with

Catherine Hope All Realty Services

1515 Tennessee Ave, Monticello, FL 32344
/2
$110,000 Sold Dec 19, 2025

000 Taylor Rd, Monticello, FL 32344
- Land
- 5.17 Acres
- $21,277 per Acre
Last Sold Summary
- 0 Days On Market
Last Listing Agent D. Scott Kilgore Superior Realty Group LLC

000 Taylor Rd, Monticello, FL 32344

/4
Est $100,628 Not Listed For Sale
- 3 Beds
- 1 Bath
- 825 Sq Ft
395 W High St, Monticello, FL 32344

395 W High St, Monticello, FL 32344

/29
$239,900 Under Contract
- 3 Beds
- 2 Baths
- 1,568 Sq Ft
2503 Rabon Rd, Monticello, FL 32344

Discover peaceful country living at 2503 Rabon Road, a well-maintained 3-bedroom, 2-bath home situated on 5 private acres in Monticello. With 1,568 sq ft of comfortable living space, this property delivers the quiet, open setting buyers want while staying an easy drive from both Monticello and Tallahassee. Inside, you’ll find a bright, functional layout with generous living areas, a spacious

Clint Bailey Superior Realty Group LLC

2503 Rabon Rd, Monticello, FL 32344
/40
$425,000 Sold Apr 18, 2025

310 E Dogwood St, Monticello, FL 32344
- 4 Beds
- 3.5 Baths
- 3,174 Sq Ft
- Built 1895
Last Sold Summary
- 6% Below List Price
- $134/SF
- 27 Days On Market
Current Estimated Value $432,816

Last Listing Agent Devin Lohman Lohman Realty LLC

310 E Dogwood St, Monticello, FL 32344

/42
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,952 Sq Ft
761 Tyson Rd, Monticello, FL 32344

761 Tyson Rd, Monticello, FL 32344

/3
$437,500
- Land
- 22.13 Acres
- $19,770 per Acre
00 Boston Hwy, Monticello, FL 32344

2 MILES FROM Monticello Courthouse! Bordering Jefferson County Country Club. 2 Parcels for total of 22.13 Acres adjacent to Jefferson County Golf Club and bordering Boston Hwy- 1028 ft. frontage - and Mamie Scott Drive. 2 Acres on Mamie Scott with 360' FRONTAGE AND has City Water/Electric Access and is actually within City Limits with zoning of RESIDENTIAL-MULTIFAMILY. Remaining property zoning

Jennifer Ward Century 21 First Story

00 Boston Hwy, Monticello, FL 32344
/33
$250,000 Sold Oct 15, 2025

186 Deerhaven Ln, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,006 Sq Ft
- Built 1976
Last Sold Summary
- $249/SF
- 27 Days On Market
Current Estimated Value $245,898

Last Listing Agent Richard Snow Hartsfield Realty

186 Deerhaven Ln, Monticello, FL 32344

/42
Est $690,756 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,100 Sq Ft
649 Waukeenah Plantation Rd, Monticello, FL 32344

649 Waukeenah Plantation Rd, Monticello, FL 32344

/13
$70,000
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
40 Westview Ln, Monticello, FL 32344

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 currently occupied and offers ;an opportunity for a buyer willing to look past the exterior and focus on the potential within. Not

Alicia Radtke All Realty Services

40 Westview Ln, Monticello, FL 32344
/64
$425,000 Sold Dec 15, 2025

595 Crooked Creek Ln, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,919 Sq Ft
- Built 2022
Last Sold Summary
- $221/SF
- 61 Days On Market
Last Listing Agent Chance Shutes Keller Williams Town & Country

595 Crooked Creek Ln, Monticello, FL 32344

/18
Not Listed For Sale
0 Sweetfield Rd Unit MFRT3505054, Monticello, FL 32344

0 Sweetfield Rd Unit MFRT3505054, Monticello, FL 32344

/42
$325,000
- 4 Beds
- 3 Baths
- 2,223 Sq Ft
155 E Seminole Ave, Monticello, FL 32344

Full of character, this spacious 1950s home offers 4 bedrooms and 3 full bathrooms on a generous 0.60-acre lot in the heart of Monticello. With over 2,200 square feet—including two bedrooms with ensuite baths—it also features flexible zoning for residential, business, or mixed use. The layout includes a cozy living room with a fireplace and an airy sunroom, perfect for an office or casual dining.

Catherine Hope All Realty Services

155 E Seminole Ave, Monticello, FL 32344
/19
$389,500 Sold Jan 12, 2026

173 Deerfield Ln, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,865 Sq Ft
- Built 2025
Last Sold Summary
- 9% Below List Price
- $209/SF
- 110 Days On Market
Last Listing Agent Caleb Stephens Silo Hill Properties

173 Deerfield Ln, Monticello, FL 32344

/42
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,807 Sq Ft
21 Mire Ct, Monticello, FL 32344

21 Mire Ct, Monticello, FL 32344

/19
$395,000
- Land
- 3.2 Acres
- $123,438 per Acre
XX Shiver Rd, Monticello, FL 32345

Beautiful High lot at corner of Hwy 19, Shiver and Lake Rd. This listing is compilation of 3 contiguous parcels : (19-2N-5E-0140-0000-0300 and 19-2N-5E-0000-0210-0000 and 19-2N-5E-0140-0000-0170). for a total of 3.25 acres . PRIME location for multi-family, office, mixed use commercial business that needs visibility and ease of access. Utilities available- Water access to main line is Under Hwy

Jennifer Ward Century 21 First Story

XX Shiver Rd, Monticello, FL 32345
/36
$350,000 Sold Sep 15, 2025

259 Barnes Rd, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 2,020 Sq Ft
- Built 1990
Last Sold Summary
- 20% Below List Price
- $173/SF
- 120 Days On Market
Current Estimated Value $358,587

Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

259 Barnes Rd, Monticello, FL 32344

/42
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,807 Sq Ft
24 Mire Ct, Monticello, FL 32344

24 Mire Ct, Monticello, FL 32344

/40
$1,190,000 Under Contract
- 4 Beds
- 6 Baths
- 9,848 Sq Ft
193 Nautilus Dr, Monticello, FL 32344

Introducing a breathtaking fusion of modern convenience and medieval charm nestled in the heart of the woods. This meticulously renovated 9,848 square foot architectural marvel boasts a captivating design, featuring uniquely sized windows and curving walls that exude artistic allure at every turn. Step inside and experience the epitome of luxury living. The main building offers a seamless blend

Ondrea Maldonado Hamilton Realty Advisors LLC

193 Nautilus Dr, Monticello, FL 32344
/37
$450,000 Sold Oct 15, 2025

376 Tecumseh Rd, Monticello, FL 32344
- 4 Beds
- 3 Baths
- 2,076 Sq Ft
- Built 1990
Last Sold Summary
- 3% Below List Price
- $217/SF
- 57 Days On Market
Current Estimated Value $445,597

Last Listing Agent Casey Skelton Pearson Realty Inc.

376 Tecumseh Rd, Monticello, FL 32344

/5
Est $315,746 Not Listed For Sale
2312 Hartsfield Rd, Monticello, FL 32344

2312 Hartsfield Rd, Monticello, FL 32344

/9
$120,000
- Land
- 2.01 Acres
- $59,701 per Acre
40 Westview Ln, Monticello, FL 32344

Load up and take a ride to Lloyd Fl. located between Tallahassee and Monticello Fl. Being offered "AS IS" two 1 acre parcels 18-1N-4E-0108-000G-0030 & 18-1N-4E-0108-000G-0040 for a total of 2.01 acres! Power, septic and well on site, as well as access to city water. There is a 1989 mobile home on site that may be salvageable to the right buyer, or haul it off and prepare for a new build! Bring

Alicia Radtke All Realty Services

40 Westview Ln, 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 $519,245

Last Listing Agent Kara Richetti Real Broker LLC

141 Shumard Ct, Monticello, FL 32344

/7
Not Listed For Sale
245 Whipporwill Rd, Monticello, FL 32344

245 Whipporwill Rd, Monticello, FL 32344

/33
$999,900
- 3 Beds
- 2.5 Baths
- 4,383 Sq Ft
728 Turney Anderson Rd, Monticello, FL 32344

A Timeless Treasure, built by Riley Palmer Construction in 2006, this exceptional home captures the warmth and character of an early-1900s Craftsman farmhouse. It is located on 5 beautiful acres with mature pecan trees in the front and pines in the back yard. A spacious wrap around front porch welcomes you and features reclaimed New Orleans style doors and classic architectural details. Inside,

Jared Parramore Coastwise Realty

728 Turney Anderson Rd, 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

/42
Est $579,117 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 2,554 Sq Ft
257 Linton Place, Monticello, FL 32344

257 Linton Place, Monticello, FL 32344

/34
$199,000 Under Contract
- 3 Beds
- 2 Baths
- 1,328 Sq Ft
185 Mallard Ln, Monticello, FL 32344

See updated pictures - motivated Sellers. Newer 2020 mobile home on 1.95 acres. This simple but beautiful property backs up to a lake. Property is mostly wooded at the moment but if cleared would have a lovely view of the lake and the Monticello sunsets. Located in a quiet neighborhood in Lloyd Acres. Mobile home offers open concept living, dining and kitchen area with three bedrooms and two

Jennifer Weeks J. D. Salley & Associates, Inc

185 Mallard 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 $464,831

Last Listing Agent Sandy Ferrera All County Suncoast Property

340 E Washington St, Monticello, FL 32344

/39
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,568 Sq Ft
175 Main St, Monticello, FL 32344

175 Main St, Monticello, FL 32344

/28
$200,000
- 3 Beds
- 2 Baths
- 1,292 Sq Ft
463 Murmuring Creek Rd, Monticello, FL 32344

Move in ready home on over 5 acres in beautiful Monticello Florida. Newer Roof 2024, Freshly painted, new skirting, windows, hot water heater 2024, flooring. No HOA

Jennifer Atwell Ketcham Realty Group, Inc.

463 Murmuring Creek 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 $309,306

Last Listing Agent Catherine Hope All Realty Services

665 W Washington St, Monticello, FL 32344

/4
Not Listed For Sale
TBD Lonnie, Monticello, FL 32344

TBD Lonnie, Monticello, FL 32344

/14
$37,000
- Land
- 1 Acre
- $37,000 per Acre
1264 Quail Ln, Monticello, FL 32344

Corner lot off of paved road in Lloyd Acres. Wooded, pines and hardwoods. High elevation. Mobile homes are allowed. An additional 3.30 acres available for purchase.

Callie Rhoads The Naumann Group Real Estate

1264 Quail Ln, Monticello, FL 32344

Showing Results 201 - 240, Page 6 of 18

Florida Jefferson County Monticello

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

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

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