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$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
$299,900
3 Beds ⋅ 2 Baths ⋅ 404317 MLS
Great opportunity to be in the lovely town of Monticello off of Pearl Street. Acre lot & Concrete swimming pool with this single story home. Large rooms, hardwood floors throughout much of the house, updated kitchen cabinetry, large detached garage. House has been cleaned up & some fresh painting done but does need work and is priced accordingly. Being sold AS-IS w/right to inspect.

515 Sunset Drive, Monticello
$299,000
399642 MLS
85.69 acres of land located on Big Joe Road in Monticello. Zoned Agri-05, this versatile property offers a unique blend of privacy, natural beauty, and development potential. Featuring a mix of wetlands and usable upland areas, the property may be ideal for a variety of uses including recreational development, camping, hunting retreat, RV park, event venue, outdoor hospitality concepts, or future subdivision opportunities. Buildable portions of the property may potentially be subdivided into 5-acre parcels, creating flexibility for investors, developers, or those seeking a large private tract with long-term upside. An 80-foot setback from wetlands applies. Buyer to verify all zoning regulations, permitted uses, subdivision potential, wetland boundaries, and development feasibility with the appropriate authorities. Enjoy the peaceful North Florida setting while still being conveniently located near Monticello and within driving distance of Tallahassee. Whether you are looking for an investment opportunity, recreational property, or future development site, this acreage offers tremendous potential.

BIG JOE Road, Monticello
$298,900
3 Beds ⋅ 2 Baths ⋅ 400806 MLS
Currently under construction. Interior pictures are from a previous model home. Approximately 60 days until completion. Home qualifies for USDA financing.

1070 Partridge Lane, Monticello
$285,000
401828 MLS
Great potential, use one side and lease out the other. Duplex 310 and 320 N. Cherry St., each unit has a bathroom. The building is currently under renovation with new roof in 2025, new front windows, new vinyl plank flooring throughout most of the building.

320 N Cherry Street, Monticello
$259,900
3 Beds ⋅ 2 Baths ⋅ 399174 MLS
Nestled on 5.5 peaceful, private acres, this charming 3-bedroom, 2-bath home offers the perfect blend of space, comfort, and tranquility. Step inside to an open floor plan designed for both everyday living and effortless entertaining, with a seamless flow between the living, dining, and kitchen areas. The spacious primary suite is a true retreat, featuring a large en-suite bathroom complete with a beautifully tiled shower. Two additional bedrooms provide flexibility for family, guests, or a home office. Outside, enjoy the privacy and possibilities that come with 5.5 acres—ideal for relaxing, gardening, or simply taking in the quiet surroundings. Whether you’re looking for a peaceful homestead or a place to unwind, this property delivers. Don’t miss your chance to own your own slice of country living

1164 Oaklands Plantation Road, Monticello
$254,900
3 Beds ⋅ 2 Baths ⋅ 404967 MLS
New construction; very convenient to downtown; house is close to completion.

360 Bowman Street, Monticello
$250,000
3 Beds ⋅ 2 Baths ⋅ 403825 MLS
Nearly 6 Acres of Opportunity in Beautiful Monticello! If you're looking for space, privacy, and the possibility to create a home that truly reflects your vision, this property is it! This spacious 3-bedroom, 2-bathroom modular home offers a desirable open and split floor plan with generously sized living spaces. The expansive primary suite provides a private retreat and features a walk-in closet, dual vanities, and a separate shower. Just off the primary suite, a separate living room with a wood-burning fireplace creates a warm and inviting space to relax and unwind. The home also offers a spacious kitchen, separate dining room, and a large indoor laundry room. Step outside from the dining room to enjoy the natural, flat backyard and the privacy that nearly 6 acres provides. With plenty of room to spread out and enjoy the peaceful surroundings, this property offers an exciting opportunity for someone looking to add their personal touches and create something special. Whether you're dreaming of a private country retreat, room for hobbies and outdoor activities, or simply more space to enjoy, this Monticello property offers the land, layout, and potential to make it your own.

112 Long Leaf Drive, Monticello
$249,000
3 Beds ⋅ 2 Baths ⋅ 404983 MLS
Discover this charming 3-bedroom, 2-bath home, ideally located just off Mahan Road and conveniently close to Downtown Monticello. Featuring a vaulted living room and cozy gas fireplace, this residence offers a welcoming and spacious atmosphere. The large fenced-in yard is perfect for pets and outdoor gatherings. The master suite is generously sized for comfort. Additional highlights include a single-car garage and plenty of room for your personal touch. Don't miss the opportunity to make this lovely home yours!

30 PINE NEEDLE TRCE, Monticello
$249,000
2 Beds ⋅ 2 Baths ⋅ 404023 MLS
This is the kind of home you can move into and simply enjoy. Located in Cherry Street Square, a desirable community in the heart of historic Monticello, this immaculate two-bedroom, two-bath townhome with a bonus room or office has been thoughtfully updated from top to bottom. The interior feels fresh, bright and completely move-in ready, with luxury vinyl plank flooring, updated doors and windows, modern hardware and fixtures, and a full suite of kitchen appliances, all completed in 2022. Since then, the owners have continued improving the home with new gutters, toilets and faucets, an insulated garage door, storm door, smoke and carbon monoxide detectors, updated electrical switches and outlets, a new water heater, kitchen faucet and roof. The enclosed screened porch was added in 2025, creating a comfortable place to enjoy your morning coffee or unwind at the end of the day. A one-car garage, private driveway and back patio provide the space and convenience that can be difficult to find in townhome living. The HOA handles the yardwork and fence maintenance, giving you more time to enjoy your home—and far less time worrying about upkeep. From Cherry Court, you can walk or bike beneath Monticello’s canopy-lined streets to locally owned restaurants, coffee shops, boutiques, antique stores, craft shops and outdoor sporting stores. Downtown is centered around its historic courthouse and filled with preserved architecture, including the Monticello Opera House, giving the town a character that feels distinctly different from anywhere else in North Florida. It offers a slower pace without feeling disconnected, with Tallahassee approximately 25 miles away. Immaculately maintained, extensively updated and positioned in one of Monticello’s most convenient communities, this home offers an opportunity to simplify without sacrificing comfort, quality or location.

490 N Cherry Court, Monticello
$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
$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
$230,000
404813 MLS
1659 square foot converted office space with multiple rooms and separate 2700 square foot functioning and active storage warehouse with ample parking on one corner lot that fronts Hwy 19, walking distance to downtown Monticello. Used to house a real estate sales office. Video tours and appraisal available upon request. Needs some repair work on front decks.

1065 N Jefferson Street, Monticello
$225,000
403342 MLS
Commercial lot, good location, great zoning, cleared, surveyed.

36 Shiver Road, Monticello
$200,000
3 Beds ⋅ 2 Baths ⋅ 400858 MLS
Charming and affordable home on the North side of Monticello in Nobles Subdivision. 3 BR 1.5 Baths. Upgrades in 2021 include new ac, new water heater, new roof. Recent interior paint. Large fenced backyard.

1550 Tennessee Street, Monticello
$199,000
403966 MLS
Wooded 5.85 acre homesite. Convenient to Tallahassee. Access road has not been cleared yet to access this parcel.

TBD Old Tung Grove Road, Monticello
$199,000
399248 MLS
Fronting on Hwy-90 this high elevation lot is lightly wooded. Some restrictions apply.

TBD W Washington, Monticello
$175,000
2 Beds ⋅ 1 Baths ⋅ 405104 MLS
If you are looking for your opportunity, this home's for you! This 1950's bungalow is within reach for all. Whether a first time buyer, down-sizer, or investor, this home has ample opportunity for all! At a price where designer re-dos and renovations are possible, anyone can can make this dream come true! The huge addition (500+ sqft) off the rear of the home offers ample square footage that could possibly be reconfigured to a new owner's desires. The original home features a two bedroom one bath floor plan. The kitchen is sandwiched between two large living areas making opportunities for renovations and modernization ideal. With a third acre that's fully fenced, existing dog kennel, and a true garage, this property has built in bonuses in addition to the stellar location just moments away from Monticello's town center, access to I-10 and Hwy90 for easy commutes. Monticello is still known for its downtown charm and community events and connectedness. Just check out the chamber's facebook page! :D In addition to the Ecological Park and Legion right across the street, the house is minutes from town square where you can enjoy entertainment at Old Monticello Opera House, Vintage Stores, Restaurants. And if you wanted to, the Aldi and DG Market are walking distance to the home! So if you are looking for true potential not just in making a home, but making and enjoying community, see what 1060 S Water Street has to offer in charming Monticello, Florida!

1060 S Water Street, Monticello
$175,000
3 Beds ⋅ 2 Baths ⋅ 404538 MLS
AFFORDABLE OLD MONTICELLO (FL) HOME. Spacious, good condition, move-in-ready. Convenient, easy walk to charming downtown. Recent basic repairs and renovations (roofing, electrical, plumbing, etc). Old but very livable, with a flexible floor plan. Four possible bedrooms, two baths. Recent central heat and air. Large deck equipped with a hot tub (unknown condition) and fenced. Handicap ramp. Huge two-story storage shed. Spacious lot. This early 1900s home is still very livable and very affordable, with lots of potential to add upgrades and value.

520 E High Street, Monticello
$175,000
403421 MLS
37 ACRES, AUCILLA RIVER HUNTING TRACT NEAR MONTICELLO. FL. Fronts on US 90 ½ mile west of the Aucilla River—perhaps the most prolific wildlife corridor in the county. The NE half of the property is an extension of the river’s drainway and borders SRWMD land on two sides. It’s a great wildlife habitat. The SW half along US 90 and Gramling Road is composed of a soil type (Plummer) suitable for planted pines or clearing for pasture. It has a decades-old stand of mature pine timber. There is a potential 1-acre homesite on the highway near Gramling Road that is out of the mapped river floodplain and should be suitable for a residential structure. Tie up this property NOW and be ready for the opening of gun season on Nov. 7.

Vacant E Washington Highway, Monticello
$150,000
3 Beds ⋅ 1 Baths ⋅ 398842 MLS
Welcome to 870 Shady Lane in Monticello, Florida—a charming property that offers the perfect blend of privacy, space, and small-town appeal. Nestled on a quiet, tree-lined street, this home provides a peaceful retreat while still being conveniently close to the historic downtown district, local shops, and dining. Surrounded by mature trees and natural beauty, the property offers a serene setting ideal for relaxing mornings, outdoor gatherings, or simply enjoying North Florida’s laid-back lifestyle. Whether you're looking for a primary residence, a weekend escape, or an investment opportunity, this home presents incredible potential. Inside, you’ll find a comfortable layout with ample natural light and flexible living spaces ready to suit your needs. The generous lot provides plenty of room for gardening, recreation, or future enhancements. Located just a short drive from Tallahassee, Monticello is known for its rich history, friendly community, and scenic countryside. This property is a wonderful opportunity to enjoy the charm of rural living without sacrificing accessibility. Don’t miss your chance to own a slice of tranquility at 870 Shady Lane—where comfort, character, and opportunity come together.

870 Shady Lane, Monticello
$149,900
3 Beds ⋅ 1 Baths ⋅ 399392 MLS
Solid 3/1 SFR brick less than a mile from downtown Monticello! This quaint 1,312 sq ft home sits under a metal roof and only requires your vision and a little TLC to become a superb starter home or investment opportunity. It also includes an additional lot.

670 Poplar Street, Monticello
$144,900
404216 MLS
Beautiful live oaks, pines and other mature landscape on this 10.5 acres in quaint Monticello. Perfect opportunity to own 10+ acres to build your dream home on this blank slate. Lot is mostly flat and backs up to a power line so no building behind the property. Abundant wildlife present (deer and turkey) and bring all your yard animals. Ride up Vista Road to see your neighbors on larger lots to Waukeenah Hwy to visit the beautiful Monticello Vineyards and Winery. Lot dimensions are approximate.

XXX Vista Road, Monticello
$139,000
401805 MLS
Great Location in Western Jefferson County offering country living with the convenience of Tallahassee only minutes away. Wooded 5 acres on private lane. Restricted for site built homes with minimum of 1200 sq ft heated and cooled. Adjoining 5 available for sale.

TBD Orchard Lane, Monticello
$135,000
397041 MLS
Looking for privacy, this 10 acres provides an ideal homesite with some clearing for your homesite completed. The balance of the land is woorded with a mix of hardwoords and pines. Some of the land is in welands/flood which provides a nice buffer for privacy and a wildlife habitat. There is a well/pump (no tank), an older septic, and power pole. 15 ft easement leads to the property. Located just a few minutes north of Monticello.

576 Cox Road, 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
$125,000
402606 MLS
Back on the market - Discover the perfect place to build your dream home on this beautiful nearly 6-acre parcel! Enjoy the peace and privacy of country living with the convenience of being just minutes from the interstate and a short drive to Tallahassee. With plenty of room for your custom home, workshop, gardens, or recreational space, the possibilities are endless! Whether you’re looking to create your forever home or invest in land with an ideal location, this is an opportunity you won’t want to miss. Come experience the freedom and potential this exceptional property has to offer!

Eastwood Road, Monticello
$120,000
404598 MLS
Discover the perfect opportunity to build, invest, or create your own private North Florida retreat. Desirable combination of cleared in the front for homesite and wooded back half for seclusion. Conveniently located on a paved road with easy access to I-10 for shopping, dining, and more amenities in both Tallahassee and Monticello.

402 Mistletoe Lane, Monticello
$116,500
3 Beds ⋅ 2 Baths ⋅ 404606 MLS
Calling all investors, house-flippers, and handy homewoners! Fix & Flip for cash or hold for rental income. Located just 3 minutes from downtown Monticello and 30 minutes to Tallahassee. This 1968 two-story home is built on concrete blocks (1st story), & sits on a large 0.38-acre lot with mature vegetation for privacy on 2 sides. Has a metal roof (unknown age), HVAC~ 2020. Utilities are on for showings. Priced for an AS-IS sale, including any bulk junk left from tenants. Exterior stairs are being repaired.

1420 Tennessee Avenue, Monticello
$104,000
402857 MLS
Mobile-home-friendly property with a cleared homesite and an existing well, septic system, and electrical service already on the property. Seller financing is available. Conveniently located near I-10 and approximately 30 minutes from Tallahassee. Bring your home plans and enjoy a quiet country setting with room for animals, gardening, outdoor projects, and additional storage. Fence the property and create the private rural lifestyle you have been looking for while remaining close to shopping, dining, and other conveniences.

130 Sweetfield Road, Monticello