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$69,900
405134 MLS
RARE 3.3-ACRE OPPORTUNITY NEAR WACISSA & AUCILLA MANAGEMENT AREA! Discover the possibilities with this unique 3.3-acre tract on Walker Springs Road in Monticello, Florida. This offering includes two separate parcels being sold together, creating a special opportunity for those looking for additional space, privacy, and flexibility. The property is zoned to allow two dwellings, making it an excellent option for a primary residence plus a second home, family setup, or future investment opportunity. Beautifully wooded with a mix of majestic longleaf pines and mature oak trees, this property offers a peaceful, natural setting filled with abundant wildlife. Outdoor enthusiasts will appreciate the location, with the entrance to the Aucilla Wildlife Management Area (40,000+ acres) less than a quarter mile away. The pristine, cool waters of the Wacissa River are also just around the corner, providing easy access to some of the area's beautiful natural resources and recreational opportunities.Conveniently located approximately 10 minutes from I-10 and 25 minutes from Tallahassee, while still offering the privacy and tranquility of rural Jefferson County. Whether you're looking to build, create a private retreat, enjoy the outdoors, or invest in land with unique possibilities, this property is worth a closer look.

0000 Vacant Walker Springs Rd, 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
$3,300,000
405055 MLS
An exceptionally rare opportunity to acquire 8+ acres with 630 ft of riverfront property on the crystal-clear, spring-fed Wacissa River in Jefferson County, FL. Bordering it's own tributary called Little River just off of the main river channel between the head of the river and the "Big Blue" Spring, this extraordinary property offers a level of privacy, exclusivity, and natural beauty rarely available on one of North Florida's most treasured waterways. This property is two separate 4.05 acre parcels with legal deeded easements to each. The back parcel has a well, electric, septic and community water already installed. The property also has a diesel generator hooked up & ready to go, should the need arise. A dock-house that is ready for you to complete however you'd like! Imagine waking up & stepping out onto the dock with a coffee in hand, sitting in cozy rocking chairs with someone you love as the fog rises off the water around you.. Oh, so peaceful. The Wacissa River flows through thousands of acres of public conservation lands and privately protected properties, preserving the natural character of this remarkable corridor that travels all the way down to the Gulf of America. Whether you are envisioning an exclusive private compound, luxury river retreat, destination recreational property or unique income-producing investment, opportunities of this scale and character on the Wacissa River are extraordinarily uncommon, don't miss this opportunity. Seller is related to real estate listing agent.

1410 Malloy Landing Road, Monticello
$93,000
404998 MLS
Discover a rare combination of privacy, recreation, and natural beauty on Johnny Road. Adjacent to the renowned Pines of Avalon Plantation and bordered by hundreds of acres of generational family land, this property offers an exceptionally secluded setting. A year-round spring-fed creek winds through the property, complemented by a small seasonal spring-fed pond and abundant wildlife. The property features a shooting shed overlooking multiple cleared shooting lanes, plus a large storage container. Thoughtful plantings include persimmons, chestnuts, swamp oak, and other fruit-producing trees. Just minutes from Monticello and I-10, this is an ideal private retreat, hunting property, or stunning setting for a dream home.

Lot 16 JOHNNY RD, 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
$254,900
3 Beds ⋅ 2 Baths ⋅ 404967 MLS
New construction; very convenient to downtown; house is close to completion.

360 Bowman Street, Monticello
$357,000
3 Beds ⋅ 2 Baths ⋅ 404878 MLS
Wonderful Cottage Home in Quaint Crooked Creek Subdivision in Monticello Florida. Open Floor Plan with 3 Beds/2 Baths. Tiled Covered Front Porch with a Large Tiled Screened Porch and Deck for Grilling. There is a Built in Storage Shed approx. 4x7. Spacious Garage with Shelves. Additional 30Amp for RV with Parking Space Designed for RV or could be used for Additional Parking. Landscape is Beautiful and Creates Privacy from Streetside and Privacy Fence with Jasmine in the Backyard. Adorable Home, Perfect for Small Family or Retiree!

535 Holly Road, Monticello
$895,000
3 Beds ⋅ 3 Baths ⋅ 404823 MLS
Tucked away on 10.87 private acres behind its own gated entrance in the sought-after Rainey Run community, this custom-built home offers the perfect balance of quality craftsmanship, modern comfort, and peaceful country living. Built by Hannon Construction in 2023, the 3-bedroom, 2.5-bath home spans 2,412 square feet and was thoughtfully designed with timeless finishes and functional spaces throughout. At the heart of the home, the kitchen features a premium ILVE range and cooktop, Electrolux refrigerator, freezer, and dishwasher, custom cabinetry by Carroll's Cabinets & Countertops of Thomasville, quartz countertops, and a spacious walk-in pantry. Custom and antique lighting adds warmth and character, while the laundry room includes a folding station or convenient drop zone with storage. The open living area is centered around a gas fireplace, and large E-rated energy-efficient windows fill the home with natural light. Storage was thoughtfully incorporated throughout the home, including an impressive 52-foot by 8-foot walk-up attic with double flooring and a dedicated storage closet pre-wired for future security technology. Just off the laundry room, you'll find a brick patio and a half bath that was thoughtfully designed to serve as a future pool bath, making it easy to expand your outdoor living space if desired. Outside, a Morton building with electricity and water provides plenty of space for a workshop, equipment, hobbies, or storage. The home also features a whole-house generator and a Rinnai tankless water heater for added convenience and peace of mind. In addition to the community gate, the property has its own private gated entrance, offering an added sense of privacy and easy access. Enjoy the peace and privacy of country living without giving up convenience. Ideally located just minutes from downtown Monticello and a short drive to Tallahassee, this home offers the best of both worlds. If you've been looking for newer construction on acreage without sacrificing quality, convenience, or location, this home is one that truly stands out. Every detail has already been thoughtfully considered, creating a property that's as functional as it is beautiful.

4216 W Washington Highway, Monticello
$1,200,000
404814 MLS
Income-producing commercial opportunity! As an investor looking to expand or a business owner seeking property, take advantage of this unique opportunity to own a commercial building and lot in Jefferson County. Don't miss this opportunity to secure an income-producing commercial property with both immediate and future potential. Any additional questions.

7339 Old Lloyd Road, 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
$529,999
3 Beds ⋅ 2 Baths ⋅ 404670 MLS
Rare opportunity to own a fully operational 20-acre working farm in the beautiful North Florida countryside. This property is currently home to both dairy cows and goats and is set up for continued agricultural use with multiple fenced pastures, established and lush Argentine Bahia grass, a milking barn, livestock holding area, and additional farm infrastructure. The property includes a 2018 three-bedroom, two-bath mobile home offering comfortable living while you work the land. The thoughtfully laid-out acreage provides multiple pastures and plenty of room for livestock, making this an ideal setup for a dairy operation, small cattle or goat farm, hobby farm, homestead, or agricultural investment. From the established pastures to the existing livestock facilities, much of the hard work has already been done. Bring your animals, continue the existing operation, or create your own vision for a productive North Florida homestead. Located along Lloyd Creek Road in the Monticello area, this property offers the opportunity to enjoy rural living while remaining within reasonable reach of Tallahassee and surrounding communities.

2462 Lloyd Creek Road, Monticello
$660,000
404641 MLS
The opportunity to own a pristine 44+ acre tract of raw land just on the outskirts of charming Monticello is now available. This largely untouched property offers a peaceful country setting with rolling farmland and classic North Florida character, making it an ideal location for your future home or recreational retreat. Situated with road frontage on Steen Road, this buildable tract is covered in mature pine trees and teeming with abundant wildlife, creating a natural haven for outdoor enthusiasts. Whether you're dreaming of a family homestead, a working farm, or a legacy property to enjoy for generations, this land provides endless possibilities. Conveniently located just minutes from historic downtown Monticello, you'll have quick and easy access to local amenities, while also enjoying the serenity of a quiet country setting. Plus, with quick routes to Interstate 10, travel to Tallahassee, Thomasville, and beyond is effortless. Embrace the natural beauty, tranquility, and potential of this exceptional property.

XXX STEEN ROAD, Monticello
$115,000
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 unsafe. Do not use.

1420 Tennessee Avenue, 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
$429,900
3 Beds ⋅ 2 Baths ⋅ 404440 MLS
Experience a nearly new construction with this stunning 3-bedroom, 2-bathroom home crafted by Nailed It Tallahassee LLC. Featuring a luxurious master suite and a dream kitchen, this property is a must-see. It includes plantation shutters and remote-controlled blinds throughout. Enjoy the privacy of a fenced-in backyard. Move-in ready!

107 Tarn Way, 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
$360,500
3 Beds ⋅ 2 Baths ⋅ 404500 MLS
Construction has begun. Completion date should be approx 4 months or less. We will update the comments as the construction progresses. Picture is virtual. More to come as construction continues. Propane appliances and Rinnai Tankless Water Heater.

1605 Sweetbay Court, Monticello
$700,000
3 Beds ⋅ 3 Baths ⋅ 404453 MLS
Set on 18+ acres of beautifully maintained pasture, this private country property is built for both everyday living, true equestrian use or small livestock farm. The land is the star- fully fenced with new wood fencing that cleanly defines multiple pastures, a peaceful pond, and wide open space to ride, graze and enjoy. The 6-stall horse barn is ready to work with paddocks attached to each stall, rubber mats, LED lights and stall fans installed recently, a large tack room and wash racks. This an ideal setup for anyone looking for a functional, turn-key horse property. The home itself is in excellent condition and thoughtfully laid out, with a spacious living room anchored by a large fireplace, a kitchen with bar seating, breakfast nook and new appliances and a separate formal dining room. Every room has a beautiful view of the farm surrounding it. Wood floors run throughout the main living areas, adding warmth and character, while all bedrooms and office are tucked upstairs for a quiet retreat. A new 2024 roof and fully repainted interior, adds peace of mind. Enjoy sweeping views of the surrounding countryside and a true sense of privacy, all while being conveniently located to both Tallahassee and Thomasville. This is a property you don't want to miss!

660 Whispering Hills Road, Monticello
$90,000
404405 MLS
Looking for a place where you can spread out, bring a mobile home, build a workshop, raise chickens, plant a garden, and create your own little slice of country life? This 2.12-acre property in Lloyd Acres gives you the space and flexibility to make it happen. Located just off a paved road and sitting at a high elevation, this property already has some of the hard work done. Power, well, and septic are already installed, giving you a valuable head start as you make plans for the property. There are also two existing small buildings on the property. One is ideal for a workshop, storage, or hobby space, while the other would make a great chicken coop. The existing mobile home conveys with the property as-is and has no contributory value. Mobile homes are allowed. Imagine having room for a garden, chickens, outdoor projects, recreational equipment, or simply plenty of space to enjoy the outdoors. And if 2.12 acres isn't quite enough, an additional 1.19 acres is available for purchase, giving you the opportunity to create a property of more than three acres.

1264 Quail Lane, Monticello
$41,000
404404 MLS
1.19 acre lot off of paved road in Lloyd Acres. Partially cleared. High elevation. Mobile homes are allowed. An additional 2.12 acres available for purchase.

XX Quail Lane, Monticello
$60,000
404331 MLS
Experience the peace and natural beauty of North Florida on this attractive 2.2 acre lot located on Walker Springs Road. The property features mature oak trees and long leaf pines and a quiet setting overlooking the Cody Escarpment. Beautiful open pastures adjoin the rear of the property, along with a picturesque pond where deer, turkey, and other wildlife regularly come to water. With abundant wildlife practically at your doorstep, this property offers an exceptional setting for nature lovers, hunters, or anyone looking for a private country homesite. Located within a quarter-mile of the approximately 40,000-acre Aucilla Wildlife Management Area and is also close to Ted Turner’s renowned Avalon Plantation and just minutes to the Wacissa River. This part of North Florida is known for its abundant wildlife, natural beauty, and outstanding hunting opportunities. Mostly dry and offering attractive building potential, this peaceful acreage provides the feeling of being far away while remaining within convenient reach of Wacissa, Monticello, and Tallahassee. Please use: 1602 Walker Springs Rd., Monticello, FL to use your favorite mapping system to get to the subject property. You will need your own address eventually (this is the address of the neighboring property). Power lines and phone lines already run along Walker Springs Road. Jefferson County Community Water is available within feet of the property. Tap in fee applies.

000 Walker Springs Rd., Monticello
$65,000
404328 MLS
Discover a rare opportunity to own 1.75 acres on Walker Springs Road, directly adjoining approximately 40,000-acres of the Aucilla Wildlife Management Area. Very few private parcels border this protected land, and this is currently the only adjoining property being offered on the market! Deer, turkey, and other wildlife are abundant and can often be seen right outside your back door. With the main entrance to the wildlife management area less than a quarter-mile away, this property is ideally situated for hunters, outdoor enthusiasts, or anyone seeking a peaceful escape surrounded by nature. The property features magnificent grandfather oaks draped in Spanish moss, creating the timeless atmosphere of old Florida. A 12x20-foot shed is already on the property and could potentially be used as a simple hunting camp, weekend retreat, or storage building. Conveniently located just minutes from the pristine Wacissa River, approximately 25 miles from Tallahassee and 20 miles from Monticello—this exceptional property offers privacy and natural beauty without being too far from town.

1602 Walker Springs Rd., 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
$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
$135,750
404212 MLS
Discover the perfect opportunity to own a pristine 9-acre tract of raw land just on the outskirts of charming Monticello. This largely untouched property offers a peaceful country setting with rolling farmland and classic North Florida character, making it an ideal location for your future home or recreational retreat. Situated with road frontage on Ashville Highway, this buildable tract is covered in mature pine trees and teeming with abundant wildlife, creating a natural haven for outdoor enthusiasts. Whether you're dreaming of a family homestead, a working farm, or a legacy property to enjoy for generations, this land provides endless possibilities. Conveniently located just minutes from historic downtown Monticello, you'll have quick and easy access to local amenities, while also enjoying the serenity of a quiet country setting. Plus, with quick routes to Interstate 10, travel to Tallahassee, Thomasville, and beyond is effortless. Embrace the natural beauty, tranquility, and potential of this exceptional property—an ideal place for recreation, agriculture, or a peaceful family home. Don’t miss your chance to own a piece of North Florida’s timeless landscape.

XXX Ashville HWY, 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
$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
$85,000
403844 MLS
Designed and built to be a church, but can be used for a variety of commercial purposes, including office space: Lots of rooms and spaces on the ground floor, in addition to the top floor sanctuary area with side offices and bathroom. Fronts US Hwy 19 with 4-lanes and side walks on both sides. Six minute walk to the center of downtown Monticello and surrounded by other business, with some residential immediately behind. Appx 8 parking spaces accessible from side road. Concrete block siding. Air conditioning is from window units. 4,392 square feet advertised includes the ground floor and partial basement area. Appraisal available. Currently vacant with some furnishings. Needs some renovation and clean up. Sold completely as-is, including all furniture and contents.

685 S Jefferson Street, Monticello
$695,000
5 Beds ⋅ 3 Baths ⋅ 403842 MLS
Just 3 miles south of Monticello, FL and only 2.5 miles from I-10, this 10.45 acre working homestead has been thoughtfully set up for country living, livestock and extended family. The 3,536 sq. ft. home features 4 bedrooms/2 baths in the main house (with the set up for an additional bath upstairs) master is conveniently located downstairs with two walk-in closets, private access, plenty of lighting and a huge newly renovated bathroom, whirlpool tub in spare bath, high ceilings in the living area with a wood burning fireplace, bright beautiful kitchen with corrian counter tops, new dishwasher, new stovetop and french doors leading to the best views of the back of the property. This exceptional property also includes a private one bedroom, one bath mother in law suite with its own private entrance, connected to the main home by an enclosed breezeway (initially set up for a small hair salon business). The suite offers a large living area, new step in shower, new refrigerator, kitchen sink, microwave even their own back porch! Ideal for a parent, grown child, guests or simply someone who needs a little independence while staying close to family. Outside is where the property really earns the name farmstead. Six fenced paddocks (Bekaret 4ft high tensile sheep and goat fence) along with "no climb fencing in the back yard for the dogs. Pines, crape myrtles, beautiful live oaks run on the back side of the house providing ample shade for livestock. There is a three bay pole barn (25x30), equipment shed/potting house (15x50), additional equipment barn (25x60), chicken coop (10x16), peach trees and blueberry bushes, plus plenty of room to continue growing, gardening and raising animals. New pitcher pump well provides access to water even when the power is out with the option to hook up to community water. Water is ran to EVERY pasture clear up to the main road! The property is gated with Ghost Controls, fenced and has excellent frontage on Waukeenah Highway. Best of all, there is no HOA and no deed restrictions to tell you how to use your own 10.45 acres. This insn't just a house with acreage. It's an established country homestead with the infrastructure already in place and close enough to town for conveniences. Most everything on the property is negotiable...including tractor with attachments, chickens, as well as other equipment and furnishings.

2247 Waukeenah Hwy, 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