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!
HOME HAS BRAND NEW LUXURY PLANK VINYL~ Custom home built by Kessler Construction on 2 full acres in desirable Crook Creek subdivision~4 bedrooms/3 full baths~gourmet kitchen~split bedroom plan~luxury master bath~incredibly high ceilings~42x14 screened porch~oversized 2-car garage~located on a cul-de-sac, this home offers peaceful privacy
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
Leave Urbana and breathe… 10.54 acres in Exclusive Casa Bianca Ridge. Beautiful, rare lot on which to build your dream home. There is room to create a multi-generational paradise or your own personal playground. Nicely wooded parcel with a gentle stream deeper into the property. Very private. Survey in associated docs. Move quickly. Gate at Driveway. Do not enter the property without approval.
Just WOW this beautiful new construction home, with top-of-the-line custom finishes. This home gives you all the luxury you are looking for - a primary suite with stunning tongue and groove wood tray ceilings, master bath with stand-alone soaking tub, walk-in shower, double vanity with quartz countertops, an oversized walk-in custom master closet with built-ins. As you approach the living area, you are greeted with a beautiful space designed for comfort and luxury - tongue and groove wood tray ceilings to complement the ones in the primary suite, gas brick fireplace. luxury vinyl plank flooring. The open concept allows for the living space and stunning kitchen to compliment each other perfectly. In the kitchen you will find custom cabinets, quartz countertops, tile backsplash, luxury LG appliance package with touchscreen stove/oven. The dining area is the perfect space to gather together, and right off the dining area a door leads you to your 1 acre backyard oasis with a large covered porch area. Back inside the home, you have an additional two bedrooms, with carpet, and a beautiful additional bathroom with a bathtub/shower combo with tile. The Sanctuary neighborhood has a 100 acre HOA owned property that can be used to walking, trail/golf cart riding, or hunting. This neighborhood and this home are at the top of their class! You don't want to miss out on this one! Measurements are not exact, up to buyer to confirm.
Introducing a stunning 1.2 acre estate in the heart of Historic Downtown Monticello. The Simon-Ridgeway home was built in 1888 and boasts a generous 4,500 sq ft of living space and features 7 spacious bedrooms, 5 of which come with its own en-suite bathroom for ultimate privacy and convenience. City granted BNB status - making this perfect for an owner/occupier wanting to work from home and enjoy small town life! You'll fall in love with the intricately designed hardwood floors that flow throughout the home, perfectly complementing the timeless charm. The newly remodeled kitchen is a chef's dream, blending modern amenities with classic elegance, from the large farmhouse sink to the new Stainless Steel appliances. Too many updates to list- but some include a new roof, AC's, bathrooms, and kitchen, just to name a few! Enjoy the slower pace of life from the huge, Double-Story Gothic Revival front porches or the large back deck. Other outdoor features include: Large Detached Double garage with washer dryer hookups; and 2 small houses in the backyard for multigenerational living, Airbnb income or extra space for guests! Don't miss your chance to own a piece of history that offers both luxury and comfort. Schedule a showing today! Creative Financing available.
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.
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!
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!
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.
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.
New Construction. Images are renderings. 4-bedroom, 3-bath home coming soon in Tally Hills Estates. Construction has started on this beautifully designed, new construction home set on over 5 acres.
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.
Welcome to this beautifully custom-built 3 bedroom, 2 bath home completed in 2024 and located in the desirable Hemings Pond Subdivision. Offering the perfect blend of modern construction and thoughtful upgrades, this move-in ready showcases luxury vinyl plank flooring, upgraded light fixtures, premium countertops, and elegant bath fixtures. Owner selected custom enhancements elevate the space even further, including wooden plantation shutters, remote-control roller shades in all the bedrooms, a shadow box privacy fence enclosing the backyard, and a full irrigation system for easy outdoor maintenance. Also included in the owner upgrades is a covered patio for outdoor entertaining. Situated just outside the city limits, this home provides the comfort of new construction with added privacy and convenience. Don't miss your chance to own this stylish, turnkey property in a growing community! Seller offering $10,000 in closing cost with acceptable offer!
Very convenient location in the heart of Monticello. Excellent condition. Very good condition, new roof, new windows, newer flooring throughout. 10X12 storage shed.
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.
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.
Nestled on 5.56 acres of fenced pastureland, this stunning estate, is framed by majestic oak trees and welcomes you through a private gated entrance. From the rocking chair front porch to the thoughtfully designed interior, this property offers the perfect blend of luxury and country living. Living room kitchen combination with the stone fireplace creating a warm and inviting focal point. The primary suite is enormous with a sitting room separated by a two sided electric fireplace, massive bath 10x20, and an huge walkin closet 10x18. The upstairs offers 2 bedrooms, each with its own large bonus room attached. Additional features include a whole house generator, large workshop with 4 roll up doors, rv pad with power and water, and the property is totally fenced.
Back on the Market! Out of town buyers financing fell through. Welcome to this stunning new construction masterpiece, meticulously designed and built by the esteemed Kasdorf Design & Build, LLC. This craftsman beauty is awaiting its first owners and will be ready for occupancy by the mid of June. Spanning an impressive 2134 square feet, this home offers a spacious and open concept floor plan, perfect for modern living. The split floor plan provides privacy and convenience, while the huge 4.25 acre lot offers ample space and tranquility. Nestled in a Hiawatha Farms gated community this property provides a secluded feel while still being conveniently close to I-10. You'll enjoy the benefits of a friendly neighborhood association. Step inside and be greeted by the inviting atmosphere of this 3-bedroom home. Additionally, an office or bonus room with a barn door entrance provides flexibility to suit your needs. The 2.5 bathrooms feature modern tile and luxurious finishes. The heart of the home is the living room, boasting a electric fireplace with a shiplap accent wall that adds warmth and character. The tray ceiling create an elegant and unique touch. The kitchen is a chef's dream, with quartz countertops, a large island offering plenty of storage, and sleek matte black finishes that exude contemporary style. Throughout the main living spaces and all bedrooms, you'll find durable and stylish luxury vinyl plank flooring, providing both beauty and functionality. The meticulous attention to detail extends to every aspect of this home. Please note that the pictures provided are from a previous build with the same floor plan, offering a glimpse into the quality and craftsmanship that will be present in your new home. Don't miss this extraordinary opportunity to own a brand-new, move-in ready home in a secluded yet convenient location. Schedule a private showing and explore the endless possibilities that await you in this exceptional new construction build.
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.
Great location for this property in Lloyd Acres. The property has 2.26 acres of partially wooded area. The property consists of the single family home, detached garage/carport/workshop and a singlewide mobile home. The vinyl sided home will need some repair and updating but has tremendous potential. The detached garage is large with 2 stalls. The mobile home is in need of a total renovation (or demolition).
Gated rural community, lakefront 10 acres with large hardwoods. Tranquility awaits, gently sloping land with some clearing.
**MOTIVATED SELLERS - CONCESSION(S) BEING OFFERED** Remarkable, peaceful in-town oasis on 3.54 acres! An incredible find in the heart of downtown Monticello, FL. Not only is this home located on a private 3.54 acre spread, surrounded by a perimeter of natural foliage, but the home itself has been beautifully updated, blending the charm of old and the convenience of new. The 3 bedroom/3 bathroom, 2,000+ sq ft home has a kitchen flooded with natural light overlooking beautiful back yard views. The Master Suite is incredibly spacious, with it's own sitting area and/or office space. The Master Bath has a double vanity and tiled walked in shower. The Master also has it's own private, exterior door access. Outdoors, there is a pool house with a lap pool, a commercial grade greenhouse, (2) additional outbuildings (1 with electric/water), a koi pond and beautiful landscaping throughout, with a multitude of gorgeous flowers, planted by a professional gardener/florist, that bloom throughout the year. Hummingbirds are plentiful daily (except during winter) if you keep the feeders full of nectar! Also, the property has a citrus grove with three large orange trees (2 naval and 1 honeybell) and two lime trees. Roof (2022) A/C (upgraded, 2021). A must see for sure! **Note: One bedroom (10x10) is not pictured, because it was being used for storage at the time photos were taken.
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.
Gorgeous brand new construction on half acre or more! One story split floorplan with large master suite. Granite countertops with custom cabinetry. Ample living space and open concept with 10' trey ceilings. 3 bedrooms and 2 full baths and huge master shower. Fiber cement siding and architectural shingles. 185 total square feet of outside sitting space. Large 2 car garage. We have some homes in progress and some that have not even been started. No matter your timeframe, we can accommodate. Photos are of previous built home. Estimated completion date is 03/31/2023.
The data relating to real estate for sale on this website comes in part from the Internet Data Exchange Program of Tallahassee Board of Realtors. The information is provided exclusively for consumers’ personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate.
Monticello is located in Florida. Monticello, Florida has a population of 2,539. Monticello is less family-centric than the surrounding county with 15.42% of the households containing married families with children. The county average for households married with children is 20.81%.
The median household income in Monticello, Florida is $43,780. The median household income for the surrounding county is $53,080 compared to the national median of $69,021. The median age of people living in Monticello is 53.5 years.
The average high temperature in July is 91.4 degrees, with an average low temperature in January of 38.5 degrees. The average rainfall is approximately 53.9 inches per year, with 0.1 inches of snow per year.
