Monticello, Florida listings for sale

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$595,000 - Monticello, FL
3827 N Jefferson Street Monticello, FL - Stylish Brick Home on 5 acres with pond. Extra roomy with 3000 + sf of living area. Home has formal living and dining along with a lovey family room with fireplace off of kitchen. Additionally, there is an office and large sun-porch. Master Bedroom is extra large with oversized master bath. Easy commute to Thomasville, Georgia.
2007 | 3 | 3 | 3,026 sqft.
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$589,000 - Monticello, FL
Xxx Taylor Road Monticello, FL - Proposed Construction on 5.2 acres Taylor Rd. Wonderful Jefferson County location. Minutes from I-10/ Gamble Rd. + downtown Monticello. New 5 lot mini subdivision paved frontage, minimal restrictions to protect values. Underground County water available.
2024 | 3 | 2 | 1,924 sqft.
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$565,000 - Monticello, FL
141 Shumard Court Monticello, FL - This stunning 3-bedroom, 3-bath home is perfectly situated on a quiet cul-de-sac, offering the ideal blend of modern comfort and thoughtful upgrades, all on a fully fenced 0.90-acre lot. The spacious open floor plan is designed for both entertaining and everyday living, complemented by a gourmet kitchen with stainless steel appliances. The garage includes an added sink for extra convenience, and the newly built TREX deck provides a serene outdoor retreat. Energy-efficient features include a tankless hot water heater and two solar exhaust fans, along with the added peace of mind of a whole-home generator. Additional upgrades include hurricane shutters, beautiful wood floors throughout, and a finished upstairs area with a full bath, ideal for guests or a home office. Nestled in a tranquil setting with so many thoughtful details, this home is ready to impress—schedule your tour today!
2021 | 3 | 3 | 2,661 sqft.
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$499,000 - Monticello, FL
4287 Bassett Dairy Road Monticello, FL - Rare COUNTRY Farmhouse OASIS AWAITS! – Discover the perfect blend of rustic charm in this stunning 5-bedroom, 3-bathroom home, nestled on five fully fenced acres of picturesque pastureland. Located just 15 minutes from downtown Monticello, this peaceful retreat offers breathtaking views, abundant wildlife, and plenty of space for your pets to roam. Step inside to a beautifully updated, cabin-inspired interior, where every detail has been thoughtfully enhanced: Recent Upgrades: New Roof in 2018 Generac generator 2023 The well is tied in & there is a 220 gallon propane tank buried in the front yard. Brand-new plumbing throughout 2024. All three bathrooms fully remodeled 2023. New HVAC system 2023. Two complete septic systems, well pump, and drain fields 2023. Two new hot water heaters 2023. All-new flooring throughout 2023. 5-zone irrigation system 2023. New soffit around entire home, gutters, and downspouts 2023. New appliances 2023-2024. Office building for remote work or creative space. The electrical meter for the little house is in the Barn. Gazebo. Barns with sentry light, (All of the barns have been reinforced with new lumber. Additionally, the big wooden barn has a new roof.) New kitchen countertops. New custom garage door – Works perfectly but is locked down for security purposes. The screening on the porch is all new. Ceiling fans on porch are all new, paint on porch floor is new as well. Gorgeous stone fireplace- wood burning, the ridge cap outside on the top of the chimney for the fireplace is custom made. Bountiful Harvest Awaits! All the trees planted on the property have irrigation, with there being 5 irrigation zones. The clock for the irrigation is inside the big wooden barn by the well. Variety of thriving fruit trees, including: Gordon apples, Peaches, Navel oranges, Grapefruit, Mulberries, Blackberries, Blueberries, Plums, Pears, Figs, Satsumas, Persimmons, Pecans, Truly Move-In Ready! This home comes fully furnished with thoughtfully selected pieces, all purchased in 2023-2024. Bonus: A Kubota BX 1880 tractor with mowing, front loader, and tiller attachments conveys with the property, making land maintenance effortless! Property Notes: Vacant & Secure – Cameras and audio surveillance are in place for added security. There are two gates that are locked with motion detectors that ring into the home. Don't miss this rare opportunity to own a slice of paradise. Schedule your private tour today!
1983 | 4 | 3 | 2,555 sqft.
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$469,995 - Monticello, FL
52 Mire Court Monticello, FL - Amazing new construction 3 bedroom 3 bathroom by Nailed It Tallahassee LLC Come pick out all your finishes, home scheduled for completion August 2025. Luxurious master suite, Kitchen made of dreams, this is a must see! Preferred Lender offering 1% in closing costs! Photos of previous home come make this one your own!
2025 | 3 | 2 | 1,940 sqft.
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$460,995 - Monticello, FL
47 Mire Court Monticello, FL - Amazing new construction 3 bedroom 2 bathroom by Nailed It Tallahassee LLC Come pick out all your finishes, home scheduled for completion August 2025. Luxurious master suite, Kitchen made of dreams, this is a must see! Preferred Lender offering 1% in closing costs! Photos of previous home come make this one your own!
2025 | 3 | 2 | 1,806 sqft.
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$449,000 - Monticello, FL
4710 Waukeenah Highway Monticello, FL - Monticello living is good, peaceful living. This home is ready for a multi-generational family, or a family with loads of relatives and friends to entertain. This three bedroom, two bath home has an adjacent mother in law suite complete with bedroom, kitchen, bath and living room. Located on two acres with a 2025 a/c unit, 2019 roof, large screened and unscreened porch, 3 pad carport, 3 work/hobby/storage rooms, new speedy Conexon fiber internet service and a working greenhouse; this home accommodates all sorts of fun or work activities, or you can simply sit back, relax and enjoy the serenity.
1987 | 4 | 3 | 2,832 sqft.
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$439,000 - Monticello, FL
339 Silver Lake Road Monticello, FL - Beautiful private country setting with large oaks and open pasture! Extra roomy home with open concept kitchen/dining/living and wood burning fireplace. Bring the kids and the horses and chickens. Silver Lake Road is a dead end road which makes this property extra quiet and private. Lots of room to build a barn and/or workshop.
1980 | 3 | 3 | 2,706 sqft.
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$430,000 - Monticello, FL
173 Deerfield Road Monticello, FL - PHOTOS COMING SOON! Welcome to this beautifully maintained 3-bedroom, 2-bath home offering the perfect blend of peaceful country living and modern upgrades. Nestled on a full acre of land, this charming property is a rare gem with no HOA restrictions—giving you the freedom to truly make it your own. Step inside and be captivated by the open and inviting floor plan, featuring both a formal living room and a cozy family room—each space perfect for entertaining or relaxing with loved ones. A stunning fireplace in the family room creates the ideal ambiance for chilly evenings, while large windows allow natural light to flood the space. Elegant double tray ceilings add architectural interest and a sense of grandeur to the main living areas and primary suite. The heart of the home—the kitchen—boasts granite countertops, rich cabinetry, and a functional layout that will delight any home chef. Luxury vinyl plank flooring flows throughout the home, combining durability with a modern, stylish finish. The primary suite is a serene retreat, complete with a spa-like en-suite bathroom and generous closet space. Two additional bedrooms provide flexibility for guests, a home office, or growing families. Enjoy endless outdoor possibilities on the expansive, flat acre—ideal for a garden, play area, workshop, or even parking your recreational vehicles. With no HOA, you can truly customize your space to suit your lifestyle. Whether you're looking to escape the hustle and bustle of city life or simply want more room to breathe, this home delivers country living at its best—without compromising on comfort or style.
2025 | 3 | 2 | 1,865 sqft.
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$427,900 - Monticello, FL
115 Crooked Creek Lane Monticello, FL - New Construction in Crooked Creek on a spacious .72 acre lot! This open plan features 4 bedrooms, 2 bathrooms and a 2 car garage (floor plan and survey are attached in associated docs). The kitchen has a light and bright design with white cabinets, quartz counters, subway tile backsplash, and GE stainless appliances. LVP flooring throughout (tile in baths), electric fireplace, covered back patio, and pre-wired for security and surround sound. This home is a must-see!
2025 | 4 | 2 | 1,809 sqft.