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$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 boat-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
$2,735,850
7 Beds ⋅ 7 Baths ⋅ 398839 MLS
Welcome to a rare opportunity to own a true estate property where space, craftsmanship, and privacy come together on 70 beautiful acres. Only 15 minutes to Whole foods & trader Joe's This impressive 7-bedroom, 5 full bath, 2 half bath two-story home offers a thoughtfully designed layout ideal for both everyday living and entertaining on a grand scale. Upstairs features 4 bedrooms and 2 full baths, while the downstairs includes 2 bedrooms, 2.5 baths, a formal dining room, and a cozy private study—perfect for working from home or quiet retreat. At the heart of the home, a massive kitchen opens seamlessly into the living room, creating an inviting open floor plan that flows effortlessly to the outdoor living space. Step outside to your outdoor kitchen overlooking a stunning paver pool deck, hot tub, and resort-style setting built for gatherings and relaxation. Just steps away, the pool house offers even more flexibility with a loft and full bath upstairs. Downstairs, you’ll find remarkable character and craftsmanship featuring herringbone brick floors, pecky cypress ceilings, a custom bar area with half bath, and a discreet hidden gun room that adds a unique touch to this one-of-a-kind property. Whether you’re hosting guests, enjoying peaceful country living, or looking for a multi-functional estate with room to roam, this property delivers unmatched charm, privacy, and versatility. A property like this is more than a home—it’s a lifestyle. NEW 2025 Roof/HVAC

305 old lloyd Road, Monticello
$1,950,000
6 Beds ⋅ 7 Baths ⋅ 398259 MLS
Welcome to a rare opportunity to own a true estate property where space, craftsmanship, and privacy come together on 18 beautiful acres. This impressive 7-bedroom, 5 full bath, 2 half bath two-story home offers a thoughtfully designed layout ideal for both everyday living and entertaining on a grand scale. Upstairs features 4 bedrooms and 2 full baths, while the downstairs includes 2 bedrooms, 2.5 baths, a formal dining room, and a cozy private study—perfect for working from home or quiet retreat. At the heart of the home, a massive kitchen opens seamlessly into the living room, creating an inviting open floor plan that flows effortlessly to the outdoor living space. Step outside to your outdoor kitchen overlooking a stunning paver pool deck, hot tub, and resort-style setting built for gatherings and relaxation. Just steps away, the pool house offers even more flexibility with a loft and full bath upstairs. Downstairs, you’ll find remarkable character and craftsmanship featuring herringbone brick floors, pecky cypress ceilings, a custom bar area with half bath, and a discreet hidden gun room that adds a unique touch to this one-of-a-kind property. Whether you’re hosting guests, enjoying peaceful country living, or looking for a multi-functional estate with room to roam, this property delivers unmatched charm, privacy, and versatility. A property like this is more than a home—it’s a lifestyle. NEW 2025 Roof/HVAC

305 Old Lloyd Road, Monticello
$1,495,000
403407 MLS
A Landmark Opportunity in the Heart of Historic Downtown Monticello Rich in character and brimming with possibility, this remarkable circa-1901 building offers approximately 13,650 square feet in a prominent downtown location surrounded by Monticello's shops, restaurants, businesses, and historic charm. The ground floor is currently configured with three distinct commercial units, creating opportunities for multiple income streams, owner-occupied businesses, retail, professional offices, galleries, studios, dining concepts, or other ventures. Upstairs, an expansive open floor plan provides an extraordinary canvas for transformation. Imagine a spectacular loft-style residence above your own business, an elegant collection of residential units, boutique accommodations, creative workspaces, or a thoughtfully designed mixed-use or condominium development. Original hardwood floors, exposed brick walls, antique doors, soaring open spaces, and more than a century of architectural history give this property an atmosphere that simply cannot be replicated. The vacant lot behind the building adds another valuable dimension, offering potential for parking, outdoor gathering space, gardens, future improvements, or additional development. This is more than a commercial building--it is an opportunity to reimagine one of downtown Monticello's enduring landmarks. Whether envisioned as an income-producing investment, a signature live-work property, a residential conversion, or a mixed-use destination, 215 N Jefferson St offers the space, character, and flexibility to create something truly exceptional. Bring your vision and become the next steward of this extraordinary piece of Monticello history. Residential, condominium, hospitality, and redevelopment concepts are subject to applicable zoning, permitting, historic-preservation requirements, and governmental approvals.

215 N Jefferson Street, 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
$1,175,000
3 Beds ⋅ 2 Baths ⋅ 399764 MLS
Experience the beauty and tranquility of North Florida living on this stunning estate located just south of Monticello with an easy commute to Tallahassee. This remarkable property features a mature pecan grove, two scenic ponds, along with a creek and open pasture perfect for horses or livestock. The centerpiece of the property is a beautifully crafted home filled with warmth, charm, and custom details throughout. Expansive wraparound covered slate porches invite you to relax and take in the peaceful surroundings. The oversized screened back porch and large patio overlook ponds and pecan grove, creating the perfect setting for gatherings or quiet evenings at home. Inside you will find exceptional craftsmanship including reclaimed pine floors, solid wood doors throughout, elegant crown molding, soaring vaulted ceilings, and a stunning stone gas fireplace. The spacious chef’s kitchen is designed for both everyday living and entertaining, featuring Corian countertops, wine cooler, abundant prep space, and a professional style 6 burner gas stove. Additional property features include a 3 car attached carport with storage area. There are 2 outbuildings with concrete floors, power, and water. The 48x36 barn includes a bedroom with full bath. Both buildings could be ideal for horses, kennels, hobbies or workshop space. There is also a 70x24 pole barn with water, great for equipment, RV, or hay storage. This unique property offers the perfect combination of luxury country living, functional acreage, and endless possibilities for equestrian use, recreation, farming, or multi-generational living. A rare opportunity to own a truly special estate in the heart of North Florida!

1590 Tyson Road, Monticello
$949,000
3 Beds ⋅ 3 Baths ⋅ 402573 MLS
A rare opportunity to own a truly one-of-a-kind custom estate! Nestled on a private, fully fenced homesite overlooking 26 acres of golf course-like grounds, this 2021 custom-build home offers over 2,700 square feet of thoughtfully designed living space with breathtaking 270° views, including peaceful creek frontage. Built for both luxury and peace of mind, the home features hurricane shutters, a 250 mph-rated safe room, whole-home generator, soaring 10' and 16' ceilings, and extensive porcelain tile outdoor living areas, including an outdoor kitchen. Car enthusiasts, hobbyists, and RV owners will appreciate the impressive 1,500 sq. ft. insulated and cooled 4-car garage/workshop with water, additional equipment building, and 65-amp RV hookup with dedicated septic. Private, secure, and conveniently located, this exceptional property delivers the perfect blend of comfort, functionality and unforgettable views.

307 Crabapple Drive, Monticello
$899,000
3 Beds ⋅ 3 Baths ⋅ 403355 MLS
PRIVATE 41-ACRE ESTATE MINUTES FROM TALLAHASSEE - TRAILS, WILDLIFE, PASTURE & CUSTOM HOME Nestled among majestic oaks and rolling countryside, this exceptional estate offers a rare combination of privacy, natural beauty and comfortable country living. Beyond the gated entrance lies a beautiful setting of open land, mature trees, and abundant wildlife, offering endless possibilities for equestrian pursuits, a hobby farm, outdoor recreation, or simply a peaceful retreat from the pace of city life. Enjoy morning walks under the forest canopy, spend evenings watching deer and wild turkey from your porch, and observing stars under the dark skies. Yet despite its secluded setting, the property is conveniently located within easy reach of Tallahassee’s shopping, dining, medical facilities, universities, and airport, and a short drive to the historic town of Monticello. The beautifully maintained custom home is designed for both comfort and connection to the surrounding landscape, featuring a main-floor owner’s suite with a luxurious spa bath, energy-efficient Pella double-paned windows, a new roof, and high-speed internet. Outside, a swim spa, covered RV/farm equipment storage, small pond, and acreage for future expansion, barns, guest accommodations, gardens, or additional agricultural pursuits make this property as versatile as it is inviting. Outdoor enthusiasts will appreciate the close proximity to the Wacissa River, known for kayaking, fishing, and plentiful wildlife. With no HOA restrictions, you have the freedom to create the lifestyle you’ve imagined while experiencing the beauty and tranquility that only a truly exceptional North Florida estate can provide.

9901 Gamble 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
$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
$699,000
6 Beds ⋅ 4 Baths ⋅ 399129 MLS
Historic soul. Modern substance. A rare circa-late 1800s home, beautifully restored and thoughtfully made NEW. Some houses simply endure… and some are given the rare chance to begin again. Better than New Construction! Just two blocks from the courthouse square in Monticello, Fl, this circa-late 1800s home—a classic Southern I-house shaped by Greek Revival influence—once stood quietly waiting—its wide double porches still catching the breeze, its bones still strong, its story not yet finished. From the front porch, the gentle toll of the town bell drifts through the air, a quiet reminder of the rhythm of life just beyond the square. When its current stewards first stepped inside, they uncovered more than a home in need of repair. Tucked within its walls were photographs, letters, and fragments of lives once lived—small reminders that this home had always been something worth saving. What followed was not simply a renovation, but a full revival. With great care, the home was brought back to life—retaining its historic character while thoughtfully rebuilding nearly every major system. A new roof now shelters the structure, while updated electrical, plumbing, and HVAC systems provide modern reliability. Inside, a fully beautifully renovated kitchen and bathrooms offer the comforts of today without sacrificing the home’s original soul. Original heart pine floors remain throughout the main portion of the home. The kitchen and rear addition feature reclaimed oak flooring, carefully sourced from a late-1800s building in Chattanooga—an intentional detail that honors the home’s history at every turn. Spanning approximately 3,200 square feet, the home offers six bedrooms and three and a half baths, along with gracious living spaces, a formal dining room, and a central hallway plan that draws light and air from front to back. Tall ceilings, reaching nearly eleven feet, and decorative downstairs fireplaces lend a sense of warmth, scale, and quiet grandeur that only a home of this era can provide Outside, the signature double gallery porch stretches across both levels, inviting slow mornings, evening conversations, and the simple rhythm of small-town life—where a porch swing sways and rocking chairs settle into the day. A detached carport with an adjacent utility room adds everyday practicality without detracting from the home’s historic charm. This is not a restoration that erased the past. It is a home that has been carefully renewed—its history respected, its future secured. Set within one of North Florida’s most charming small towns, this home is just steps from the courthouse square—the heart of daily life in Monticello. Here, the pace is slower, neighbors greet one another by name, and a sense of community still quietly endures. The Mulberry House now proudly stands ready for its next chapter.

365 S MULBERRY 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
$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
$650,000
400494 MLS
Warehouse with B-2 Zoning, square footage to be verified. Approx 9000 sq ft of warehouse with remaining space in kitchen, offices, storage. There is living space with large kitchen 19x20. Total of 9 offices/rooms with 3 baths. High visibility corner fronting on Hwy-90. Paint booth from previous out collision business.

765 E Washington Street, Monticello
$599,900
4 Beds ⋅ 3 Baths ⋅ 398548 MLS
Discover this stunning 2,600+ sqft home built in 2021, offering the perfect blend of quiet country living and modern convenience. Adjoinging additional lot can also be purchased! Features include: 4 spacious bedrooms and 3 full bathrooms 2 master bedrooms located downstairs Dedicated office/bonus room – ideal for work or hobbies Modern kitchen and open living spaces Attached 2-car garage Just minutes from downtown, providing a quick and easy commute Enjoy serene country surroundings with the benefits of a new, move-in-ready home. Don’t miss out on this incredible opportunity!

140 SHUMARD Court, Monticello
$564,900
3 Beds ⋅ 2 Baths ⋅ 405271 MLS
Welcome to this beautiful one-owner home in highly sought-after Crooked Creek, located just at the edge of town in Monticello, Florida. Built in 2021 and offering over 2,000 square of living space, this meticulously maintained home is truly turnkey. Set on an impressive.76-acre lot, the property offers exceptioanl privacy and outdoor living. The beautifully fenced backyard features a sparkling in-ground pool with fountain., creating the perfect setting for relaxing, entertaining, and enjoying Florida's beautiful weather. Inside, the home offers a desirable open floor plan with plenty of natural light and a warm, inviting feel. One of the home's standout features is the lovely sunroom overlooking the pool and backyard, providing a peaceful space to enjoy your morning coffee or unwind at the end of the day. PROPERTY HIGHLIGHTS: Whole House Generator, Pool, Fenced Backyard. ADJOINING .70 ACRE LOT AVAILABLE FOR PURCHASE.

205 Crooked Creek Lane, Monticello
$499,000
5 Beds ⋅ 2 Baths ⋅ 397098 MLS
Charming Cape Cod-style home tucked away on 5 acres just minutes to downtown Monticello. This one owner home has been lovingly maintained and reflects years of care and pride of ownership. With over 2200 square feet of living space, the home offers a comfortable layout. The main floor features three bedrooms, one bath, a welcoming living room with a gas fireplace, dining area, kitchen and a convenient laundry room. The second floor includes two additional bedrooms, a full bath, and a lovely reading /library room could also serve as a playroom or flexible living space. Extra attic storage provides plenty of room for seasonal items and additional storage needs. Relax on the back enclosed porch while enjoying the beautiful views of the surrounding trees and well kept grounds. Additional features include a workshop/storage/mancave for hobbies or projects, plus and extra carport/tractor shed with additional enclosed space perfect for a potting shed and garden tools This well maintained property offers warmth, character, and peaceful surroundings . Newer roof and windows and exterior paint!

398 Tecumseh Road, Monticello
$495,000
4 Beds ⋅ 3 Baths ⋅ 397236 MLS
Exceptionally maintained , this turn key 2022 farmhouse-style home is located in the sought after Crooked Creek area.Seller is motivated! This home is ready for immediate occupancy and includes whole house generator still under warranty. This spacious 2134 sq ft home features 4 bedrooms and 2.5 baths on a generous .85 acre lot, ideally situated on a quiet cul-de-sac on the west side of Monticello. The open-concept layout offers elegant coffered ceilings crown molding and a cozy gas fireplace with built-in shelving in the living room- perfect for relaxing or entertaining. Primary suite offers an extra large bath with large walk- in shower and slipper tub. The light -filled interior creates warm and inviting atmosphere throughout the home. Enjoy peaceful living just on the edge of town, with convenient access to state capital, Tallahassee. A perfect blend of modern comfort, style, and location in a quiet neighborhood setting.

121 Shumard Court, 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
$470,000
3 Beds ⋅ 2 Baths ⋅ 403824 MLS
Photos of previous homes. Come choose all your finishes and upgrades. Home is just finishings the framing stage of construction. Amazing new construction 3 bedroom 2 bathroom by Nailed It Tallahassee LLC. Luxurious master suite, Kitchen made of dreams, this is a must see!

78 Fen Court, 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
$429,000
3 Beds ⋅ 2 Baths ⋅ 401255 MLS
*Jefferson County peaceful country living with a waterfront backdrop! Built in 2008, this well maintained 3 bedroom, 2 bath home sits on 4.89 beautifully (mostly cleared) acres offering privacy and natural beauty backing directly up to Lloyd Lake- perfect for relaxing evenings with scenic views. Pretty rocking chair front porch as well as a screened in back porch with a propane hookup for grilling and generator hookup. This split plan offers a large primary suite with dual vanities, large walk in shower w/separate soaking tub and large walk in closet. Other features include LVP wood flooring, wood burning fireplace, tankless water heater, an indoor laundry room, ceiling fans, alarm and water softener. Convenient outdoor storage w/2 tool sheds- one w/ power hook up.

285 Mallard Lane, Monticello
$425,000
399902 MLS
33+ acres in very nice rural subdivision. All wooded and will need some clearing for a homesite. Easy access to Tallahassee. Community water is available with tap in charge approx. $2500.

TBD E Cavallo Trail, 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
$424,900
4 Beds ⋅ 3 Baths ⋅ 402136 MLS
Stunning New Construction recently built by Southern Construction. Centrally located in downtown Monticello, with mature landscaping, and plenty of room for the family. This 4 bed and 3 bath home features vinyl plank flooring, granite countertops, walk in tile shower and tub in master, upgraded trim package, and stainless appliances. Nice large back porch with deck, over looking the large beautiful back yard!! Come see all this home has to offer today!!

855 S Waukeenah Street, Monticello
$398,900
3 Beds ⋅ 3 Baths ⋅ 399132 MLS
For generations, this beautifully maintained, one-family owned brick home has been a place where holidays were celebrated, children were raised, and life's everyday moments became treasured memories. Today, with only one family member remaining, the home has simply become more space than one person needs. Rather than seeing it sit too quietly, she hopes to pass it on to another family who will fill its rooms with laughter, traditions, and memories of their own. It is a home that has been deeply loved, carefully preserved, and is ready for its next chapter. Situated on 1.5 peaceful acres along North Jefferson Highway, this neo-classic 3-bedroom, 2 and a 1/2 bath home offers 3127 square feet of comfortable living space. A 24x10 screened porch invites you to slow down and enjoy quiet mornings, evening conversations, and security of nearby neighbors. Outside a concrete driveway loops around all the way to the rear, and open green space creates a setting where children can run, family pets can roam, gardens can flourish, and memories can be made. The detached 24x12 workshop provides valuable storage with a 12x12 chicken coop and multi use 12x12 farm stall behind that. An entertainment deck 24x24 is built around "The Magnolia" and a 16x28 bonus room with a half bath is waiting for your ideas to finish and decorate. Ideally located between historic downtown Monticello and Thomasville, Georgia, this property offers the rare combination of privacy, convenience, and room to grow. Whether you're gathering multiple generations under one roof, creating your forever home, or simply looking for space to breathe, this is more than a house—it's an opportunity to continue a legacy of love, laughter, and cherished memories for years to come.

1628 N Jefferson Highway, Monticello
$364,900
400229 MLS
Located in the heart of Monticello, this 5-unit investment property offers a prime opportunity for investors looking to add value and generate income. Positioned just minutes from local businesses, shopping, dining, and convenient interstate access, the location provides strong appeal for tenants seeking both convenience and accessibility. Currently, 3 of the units are occupied, providing immediate rental income, while the remaining 2 units are vacant and present an excellent value-add opportunity. Both vacant units are 1-bedroom, 1-bath units that need updating and repairs to become rent-ready, allowing the next owner to renovate and increase overall cash flow potential. Total Bedroom Count is 6 bedrooms and 5 bathrooms. Whether you are looking to expand your investment portfolio, renovate for increased returns, or capitalize on the growing demand for rental housing in Monticello, this property offers strong upside potential in a desirable in-town location.

480 S JEFFERSON Street Unit -, 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
$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
$349,000
3 Beds ⋅ 2 Baths ⋅ 397112 MLS
Rare Find! Country Living on 1 Acre-No HOA! Enjoy peaceful country living on a full 1-acre property with no HOA restrictions. This spacious 1774 square foot home features 3 bedrooms and 2 bathrooms with a bright open concept layout. The home features LVP flooring throughout, fresh interior paint in main living area, and a new roof in 2023 for added piece of mind. The primary suite includes a beautifully tiled walk-in shower in master bath. Shows like a newer home. Step outside and enjoy the freedom of country life-ideal for gardening, micro-farming, and raising chickens or goats. Conveniently located with easy access to Tallahassee. Don't miss this opportunity to own your own slice of the country!

8156 Waukeenah Highway, Monticello