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$239,000
3 Beds ⋅ 1 Baths ⋅ 396818 MLS
Very convenient location in the heart of Monticello. Excellent condition. Very good condition, new roof, new windows, newer flooring throughout. 10X12 storage shed.

220 Eaton Street, Monticello
$265,000
396434 MLS
OWN A PIECE OF HISTORIC DOWNTOWN MONTICELLO! Opportunity awaits in the heart of Historic Downtown Monticello! This versatile commercial space is currently operating as a retail shop and offers exceptional flexibility for a variety of business uses. Large front-facing windows provide abundant natural light and excellent visibility, overlooking the vibrant sidewalk area- perfect for attracting foot traffic and showcasing your business. Inside you will find spacious retail floor area, full kitchen, one bath with additional plumbing already in place for additional bath. Ample storage space leading to your own back entrance. Whether you envision a boutique, cafe, studio or specialty shop, this property offers the infrastructure and location to bring your concept to life.

185 E Dogwood Street, Monticello
$1,325,000
5 Beds ⋅ 5 Baths ⋅ 395876 MLS
Welcome to a rare North Florida estate just minutes from Tallahassee—where luxury, land, and lifestyle come together. 221 Kiley Road is situated on expansive acreage in Monticello, and this private retreat offers the perfect blend of seclusion and convenience, located just a short drive from the heart of Tallahassee. For buyers seeking space, privacy, and versatility without sacrificing proximity to town, this property delivers. 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 available, offering the rare opportunity to expand your privacy, create a multi-generational compound, or enhance the estate even further. Set on picturesque rolling land, this one-of-a-kind property features your own private vineyard, offering a breathtaking and romantic backdrop for everyday living and entertaining. Imagine sunset dinners overlooking the vines, peaceful morning walks through the rows, or simply enjoying the beauty and serenity that only a setting like this can provide. Equestrian enthusiasts will appreciate the well-appointed horse stable, open pasture, and room to ride, creating the perfect environment for both horses and riders to thrive. Thoughtfully designed for function and beauty, the grounds invite you to embrace true North Florida country living. At the heart of the property sits an impressive residence offering approximately 5,500 square feet of living space, ideal for large households, multi-generational living, or those who love to entertain. The thoughtfully designed layout features expansive living areas filled with natural light, a spacious kitchen with abundant cabinetry and workspace, and oversized bedrooms that serve as peaceful private retreats. Multiple flex spaces provide endless possibilities for home offices, media rooms, fitness areas, hobby spaces, or additional guest accommodations — tailored to fit your lifestyle. Step outside to your private pool oasis, perfect for relaxing afternoons or hosting unforgettable gatherings. A separate guest house offers comfortable accommodations for visitors, extended family, or a private retreat, adding flexibility and value to this exceptional estate. From vineyard evenings and horseback mornings to poolside afternoons, this Tallahassee luxury home alternative is more than a home — it’s a lifestyle. Offering space, versatility, natural beauty, and privacy while still convenient to downtown Monticello, schools, shopping, and dining, this is a truly rare opportunity to own a remarkable property where memories are made for generations.

221 KILEY Drive, Monticello
$45,000
395854 MLS
All Offers considered..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.

1 W meadow Road, Monticello
$495,000
2 Beds ⋅ 1 Baths ⋅ 395668 MLS
Secluded 56.37 Acres with Metal Building & Living Quarters -Western Jefferson County. This property offers privacy, versatility and room to build or expand. The land features a 2880 sq ft heavy-gauged metal building designed for both residential and workshop use. Second floor includes 1200 sf of living space currently unfinished featuring two bedrooms, kitchen and living area and one bath. A freight/lift system provides easy transport of materials and equipment to the second floor. Ground level consists of a spacious workshop/hobby area ideal for storage, projects or business use along with an attached carport for parking or equipment storage. This property is well suited for a private retreat, recreational use, homestead or a buyer seeking land with and existing structure ready for customization. There is approximately 15 acres of good usable land with the remaining land in flood zone/wetlands.

640 Nautilus Drive, Monticello
$50,000
393415 MLS
Wooded lot, pines and hardwoods. Mobile homes are allowed. High elevation.

TBD E Meadow Road, Monticello
$395,000
4 Beds ⋅ 3 Baths ⋅ 391898 MLS
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 entry—one used as a living room and one with a closet allowing for modern use as a bedroom—while upstairs includes two additional bedrooms and a full bath. The large dining room has been opened to expose the original rafters, giving the space a bright and airy feel, while six original (not currently operational) fireplaces provide historic character throughout. Period details including original hardwood floors, banisters, and molding showcase the craftsmanship of the era. Downstairs also includes a family room off the kitchen, a full guest bath, and a primary suite with an attached bath and nearby laundry. The home features a two-zone HVAC system downstairs, with window units currently serving the upstairs bedrooms. The roof is estimated to have approximately 5–7 years of remaining life. This property offers an opportunity for thoughtful updates and stewardship, presenting a great fit for buyers looking to invest in a historic home with strong bones and character. The back portion of the property remains wooded, providing privacy or potential to expand with a guest house, pool, or garden. Conveniently located just a short walk to downtown Monticello’s shops and restaurants, about 25 minutes to Thomasville, and roughly 30 minutes to Tallahassee. Offered As-Is, this home has over a century of stories—it’s ready for its next chapter. Seller is motivated and will consider all offers.

930 E Pearl Street, Monticello
$65,000
388787 MLS
1.7 acres, two lots hidden in Monticello. Will not divide. Private setting with Plantation to the west. There is a 15 ft recorded easement to the property but currently working on additional road access. No sign on property. .

TBD Scott Drive, Monticello
$130,000
383017 MLS
The listing contains (2) adjacent raw land parcels in the Lloyd Acres Subdivision = 9.96 acres total. See parcel IDs: 18-1N-4E-0113-000C-0010 (6.41 acres; Mallard Lane) + 18-1N-4E-0112-000C-0050 (3.55 acres; Bluejay Rd). Look for real estate signs (2) to help identify the acreage for sale. The property is zoned Residential-01 (1 home/1 acre), making it a great opportunity for someone wanting to subdivide, or those looking for a multi-generational property to accommodate several residences for family. Mobile homes are allowed. There are currently no utilities in place; electric, well & septic will be required. *Property is subject to a drainage easement over and across the easterly 15.0 ft.**Note - Dimensions shown are for the Mallard Ln parcel only.

00 Mallard/Blue Jay Lane Unit 2/3, Monticello
$75,000
357658 MLS
Prime vacant cleared commercial lot in downtown Monticello. Zoned Commercial B-2 Business Highway. Located Steps from US 19 South Across street from Burger King and Dollar Tree. Next door to Oreilly's Auto parts. High Traffic area and Good visibility. Address is for GPS only. Acreage is subject to survey.

205 E Cherokee Avenue, Monticello
$425,000
370572 MLS
5 office spaces with breezeway. 2 common bathrooms, one unit has a private bath. Street parking with additional parking in the city parking lot. 3 units currently rented with the owner using two spaces. Current monthly rents approx. $1700. Window unit ac in each unit.

180 S Cherry Street, Monticello
$325,000
367916 MLS
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 19 and across road. (verify with County) ZONING IS: Mixed Use Residential.

XX SHIVER Road, Monticello
$239,000
348528 MLS
Multi-purpose Building, structurally sound with large central area containing a big built-in fan and heavy-duty mechanical hoist inside large vehicle loading door. Seven adjacent rooms for offices or storage. New metal roof in 2008 by Kessler Construction. Large paved outdoor parking area beside covered loading dock. Located near downtown Monticello and about 15 miles from metro Tallahassee area and Amazon Fulfillment Center. A unique opportunity to own this property!

602 E Dogwood Street, Monticello