Monticello, Florida listings for sale

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$2,499,000 - Monticello, FL
305 Old Lloyd Road Monticello, FL - Private Estate on Nearly 30 Acres in Beautiful Monticello. Welcome to your own private retreat! This custom-built estate sits on 29.93 serene acres and offers the perfect blend of luxury, comfort, and room to roam. The main home features 5 spacious bedrooms, 4.5 baths, plus an office/family room, separate dining room, living room, playroom, and a dedicated laundry room—ideal for both everyday living and entertaining. Gorgeous cherry and pine wood floors flow throughout, and a wood-burning fireplace brings cozy charm to the living space. The oversized primary suite is a true escape with two walk-in closets and a large spa-like bathroom. Step outside to enjoy the covered porch, saltwater pool, and spa—perfect for relaxing or hosting guests. Just off the pool is a stunning 27x27 recreation room with expansive sliding glass doors that open on one side to the pool and on the other to a private basketball court. The rec space also includes a half bath, wet bar, and an upstairs 30x11 guest suite with a full bath—ideal for visitors or a private retreat. The property also includes a powered pole barn, a gated driveway, and offers additional acreage available for purchase. If you're looking for space, privacy, and a one-of-a-kind home with room to grow—this is it. Option to buy additional 150+ acres.
2007 | 6 | 6 | 6,350 sqft.
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$1,599,000 - Monticello, FL
221 Kiley Drive Monticello, FL - Welcome to a rare and exquisite, turn-key, 15-acre modern luxury estate, where timeless elegance meets Southern charm. Custom built by Riley Palmer, this exclusive, gated property is nestled just minutes from Tallahassee, Florida's Capital City, and Thomasville, GA in Monticello-home to a storied opera house and chic dining options-and offers the perfect blend of privacy, prestige and proximity. The heart of the estate is a grand Great House, designed for both refined living and effortless entertaining. Soaring ceilings, elegant finishes, and a gourmet chef's kitchen create an inviting atmosphere for everything from intimate dinners to lavish gatherings and holiday hosting. Retreat to the luxurious, spa inspired primary owner's suite on the main level, where relaxation awaits in a serene soaking tub framed by a tranquil view. Indulge in the spacious double-head shower, complete with an oversized bench designed for ultimate comfort and rejuvenation. A versatile Coach House with sink and electricity, offers ample space for horses, a workshop, or lawn equipment, plus a grassy paddock for pasturing, ideal for equestrian enthusiasts or hobbyists. Nearby, the Pool House doubles as a fully equipped guest house with full bath, kitchen and laundry, perfect for hosting weekend visitors, a rather permanent caretaker or guest, or providing a private owner art studio, jam canning, winery production or retreat. Plant in your green house, or enjoy multiple micro-vineyards boasting white Scuppernong and red Muscadine grapes for annual Fall harvesting, or make fresh peach, orange, and fig jams, or pecan pie, from your robust fruit tree offerings. Work and play from home with ample connectivity powered by Conexon Connect, the leading optic fiber broadband solution! A bonus warehouse and second well are a short walk on the adjoining 5-acre parcel with a spectacular hill-top view! Roof (2022) offering luxury Belmont by CertainTeed with lifetime transferrable warranty. Extensive Notable Estate Features list available including Vivint touch screen security system with options for 24/7 monitoring & motion detection, Generac Generator, Elan sound system, laundry shoot from second floor to mudroom, guest wet bar, side-by-side stainless KitchenAid in gourmet kitchen, plus two half refrigerators, a full-size stainless dishwasher, plus a convenient additional half dishwasher, Viking Professional six-burner gas cooktop, substantial walk-in pantry & Brew Express built-in coffee maker! Schools: Jefferson County K-12 Charter, Turning Point Alternative School or Aucilla Christian Academy, or plenty of options for classroom style home schooling. Square feet includes 576 sqft. pool guest house. 15 acres includes 3-5 acre cleared parcels. Lots 15, 16 & 17 in Timber Trace. Buyer can sell adjoining parcels if preferred, no subdividing less than 5 acres. Total bathroom count is 4 full and one half bath (4.5). Pop's Sanitation Waste Pick up option. Room measurements approximate. Buyer to verify. Welcome home!
2009 | 5 | 4 | 5,476 sqft.
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$1,390,000 - Monticello, FL
193 Nautilus Drive Monticello, FL - Introducing a breathtaking fusion of modern convenience and medieval charm nestled in the heart of the woods. This meticulouslyrenovated 9,848 square foot architectural marvel boasts a captivating design, featuring uniquely sized windows and curving wallsthat exude artistic allure at every turn. Step inside and experience the epitome of luxury living. The main building offers a seamlessblend of functionality and elegance, with a spacious kitchen offering expansive views, a library capable of housing 10,000 books,currently fill with about 6000 books that convey with the library. The ensuite bedrooms provide unparalleled comfort and privacy.The master bedroom is situated on the upper level, offering ample space and featuring a generously sized walk-in closet and twobathrooms. It provides direct access to the expansive 2000-square-foot rooftop patio, enhancing the living experience with outdoorleisure opportunities. Stay productive in the spacious office with large soundproof glass providing all the natural light, wherecreativity thrives, or use the spacious room as an additional bedroom. Discover hidden realms within the office- secret rooms!Adding an element of mystery to this home, a secret room leading to the most entertaining room in the house, the movie room!Entertainment knows no bounds within the sprawling 2,500 square-foot movie living room, complete with its own kitchen, bar,laundry setup, and bathroom for seamless hosting. Need extra space there is a cozy in-law suite/cottage in the garden equippedwith a full bathroom, kitchenette and mini-split. Outside, the grounds unfold like a verdant oasis, with a picturesque ½ acre pondwith patio and dock. Outside dinners are perfect by this serene pond on the patio furniture. Explore the outbuildings, including,chicken shed/potting shed, mushroom shed, Hügelkultur Garden beds, and greenhouse, each a testament to the estate'scommitment to sustainable living. Organic gardens include pineapple guava, loquat, black raspberries, mulberries, pears, peach,paw paws, persimmons, pomegranates, figs, hazelnuts, coneflowers, agapanthus, wildflowers, azaleas, spirea, confederate rose, abelias and so many more. An abundance of woodland, adorned with a tranquil creek meandering through its midst. Parking is abreeze with 2 different carports and a new steel 3-bay detached garage and workshop combo. An additional concrete garageshaped like a majestic whale, adding a touch of whimsy to the property's charm for extra storage. Experience a lifestyle ofunparalleled luxury and artistic inspiration where modern living harmonizes with the timeless beauty of a medieval castle, withnuggets of history still on the property through books, sculptures, and artifacts. Additional Improved Property for sale (Check out178 Nautilus Drive). Also Fiber Optics available.
1987 | 4 | 5 | 9,848 sqft.
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$1,200,000 - Monticello, FL
740 Kinsey Road Monticello, FL - Location: Jefferson County, FL Size: 155 acres Features: Rolling pastures Planted pines Natural hardwoods Pond Home: 1941 built 1,146 square feet Updated Outbuildings: With power Opportunities for workshops, storage, and more Additional Homesites: Breathtaking views Peaceful living Proximity: 10 miles from downtown Monticello, FL 5 miles to I-10 Wildlife: Deer Turkey Waterfowl Ideal for: Outdoor enthusiasts Grazing Diverse farming opportunities
1941 | 3 | 1 | 1,146 sqft.
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$1,200,000 - Monticello, FL
1165 Dills Road Monticello, FL - Nature Lover’s Dream – Custom Estate on 21+ Acres. Escape to peace and privacy in this stunning custom-built home surrounded by over 21 acres of natural beauty. Thoughtfully designed with both comfort and function in mind, this spacious estate features a gourmet kitchen with gas stove and butler’s pantry, formal and casual living spaces, a cozy library, and a luxurious primary suite with porch access overlooking a heated saltwater pool and spa. Upstairs offers two additional bedrooms, two full baths, a playroom or office, and a massive bonus room with wet bar—perfect for entertaining. A private suite above the carport provides ideal space for guests or extended family. Outdoors, enjoy a cookhouse, saltwater pool, pole barn, chicken coop, and more—ideal for hobby farming or simply soaking in the scenery. Priced at appraised value, this is the ultimate retreat for those who crave space, nature, and timeless charm. Priced at recent appraisal.
2002 | 5 | 6 | 4,700 sqft.
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$1,125,000 - Monticello, FL
825 Rainey Run Monticello, FL - Stunning estate on 10 acres in private gated community, situated just outside of Tallahassee and Monticello, Florida. This all-brick home boasts 3,696 square feet of indoor living space which includes a primary suite downstairs with 2 large closets, soaking tub and a walk in shower. The chef’s kitchen is fully equipped for hosting with touches like a GE Monogram stove and additional built-in oven, warming drawer and wine fridge, as well as a prep sink on the island. The kitchen has a wraparound bar open to the living room as well, so the chef never misses out on conversation! The living room has grand 12-foot ceilings bringing plenty of light and openness with beautiful built-in shelves flanking the gas fireplace. 10-foot ceilings throughout the rest of the home, including the formal dining room and office located on the first floor. Brand new hardwood floors run throughout the home including the 3 additional bedrooms upstairs and one of the largest bonus rooms you will find. The bonus room has a built-in bar and would fit a pool table with ease. The grounds contain beautiful live oaks and pines, pear and citrus trees, and a sandy bottom creek that runs along the east side of the property which flows north into Lake Miccosukee. The gated entrance to the property leads up a long concrete driveway to the home. Behind the home there is a 36x24 enclosed workshop with power and a 36x12 covered porch complete with porch fan and a sitting area, as well. Additionally, the oversized 2 car garage has plenty of storage space, with a newer garage door opener, the roof is brand new, new gas water heater downstairs and 2 year old gas water heater upstairs. HVAC is maintained regularly, the yard is fully irrigated and professionally landscaped. There is even gas piping ready for a grill on the back porch for an outdoor kitchen! This home has it all, including a historic look but with modern conveniences!
2007 | 4 | 4 | 3,696 sqft.
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$694,000 - Monticello, FL
17 Old Tung Grove Road Monticello, FL - Ready to move into your new home. The Ridge At Tung Grove. A small subdivision of only 5 lots. A spectacular rural location with convenient access to Tallahassee, only a 12 minute drive away. Another quality new home by Southern Coastal Homes on 6.82 wooded acres. 3 bedroom 2 bath with a bonus room with half bath. Open living space. Spacious mud room and laundry room with built ins. Other lots and homes available with varying acreage sizes.
2024 | 3 | 2 | 2,344 sqft.
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$650,000 - Monticello, FL
974 Hiawatha Farms Road Monticello, FL - Perfect blend of comfort and flexibility on this beautiful, horse-friendly property spanning over 6 acres. The main home offers 3 bedrooms and 3 full bathrooms, featuring a spacious layout designed for everyday living and effortless entertaining. Just steps away, a detached 2-bedroom, 2-bath in-law suite provides the ideal setup for multi-generational living, guests, or potential rental income. Whether you’re dreaming of a mini farm, need space for your horses, or simply crave the peace and privacy that comes with acreage, this property delivers. There's room to grow, roam, and relax—all while enjoying the kind of lifestyle that’s getting harder to find.
2007 | 5 | 5 | 3,770 sqft.
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$624,900 - Monticello, FL
181 Heritage Blvd Monticello, FL - Craftsman style house in Heritage Hills subdivision~ The house features 3 bedrooms/2 bathrooms and is energy efficient (Green Certified) ~ Luxurious hardwood flooring and a deluxe primary bathroom with separate jetted tub & large shower ~ Custom built-in cabinets in the living room and office ~ Regal craftsman style interior trim throughout and stainless-steel appliances ~ Full Solar with emergency battery backup system ~ Exterior freshly painted (Nov 2024) and new central heat pump (Aug 2024) ~ Lovely, screened porch, patio and elevated deck with the feeling of country living~ Includes heated 18’ MasterSpa H2X swimspa for relaxation and exercise ~ Landscape lighting and programable irrigation system ~ A major addition is an unattached office/mancave building (20’ x 22’) (498 square foot is part of description) with heat/AC, half bathroom and outdoor shower ~ An amazing space for music, exercise, hobbies, or home-office~ Also, designed for easy conversion to unattached garage, if desired~ All on a three-acre lot with majestic oaks in a location surprisingly convenient to Tallahassee compared to many subdivisions in Leon County!
2011 | 3 | 2 | 2,560 sqft.
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$599,900 - Monticello, FL
3873 N Jefferson Highway Monticello, FL - Stunning 4 Bedroom, 3.5 Bath Home on 9.73 Acres with Large Detached Garage plus Oversized Attached 2 Car Garage Located just north of this spacious 3,862 square foot home sits on 9.73 acres with a tranquil creek running through the rear of the property. The home is built on high and dry ground, and not located in a flood zone or HOA. Built in 2007, the home features 10-foot ceilings, hardwood flooring, carpeted bedrooms, and tiled bathrooms. Both the first and second floors boast large master suites. The second floor master includes dual walk in closets and an oversized bathroom In addition to the 4 bedrooms, this home offers an office with attached bathroom, large bonus room, separate laundry room, an expansive kitchen with a breakfast nook, a great room, and a separate dining room. The oversized attached 2-car garage is equipped with a door opener. The property includes Ethernet and RG6 cabling throughout, is wired for whole-house audio, features an HD IP camera system for added security. The exterior features a wraparound front porch, back porch, and a second-floor master balcony. A 10KW gasoline generator is included for peace of mind, with a sound-insulated enclosure and manual transfer switch. A 60x40 detached garage with workshop area, large workbench, and plenty of storage options provides an ideal space for projects. The garage is plumbed for water and drain, wired for power, and includes LED overhead lighting, a 5HP air compressor, and built-in workbenches. Conveniently located on Highway 19, just north of Monticello, you will have easy access to both Thomasville, GA, and Tallahassee, FL. Don’t miss out on this amazing property! Buyer to verify all dimensions. Property lines are approximate.
2007 | 4 | 4 | 3,862 sqft.