Monticello Homes with Jefferson County K-12 School High School

Monticello Homes with Jefferson County K-12 School High School

Welcome to Monticello, Florida—a charming gem nestled in the heart of Jefferson County. Known for its rich history and picturesque landscapes, Monticello offers a unique blend of Southern hospitality and small-town charm. With tree-lined streets, historic homes, and a vibrant community, it’s no wonder that Monticello is often referred to as the "Gateway to the Big Bend."

One of the standout features of Monticello is its strong commitment to education, with access to top-notch K-12 schools, including Jefferson County High School. Families will appreciate the emphasis on academic excellence and community involvement, making it an ideal place to raise children. The school’s dedicated staff and diverse extracurricular programs ensure that students receive a well-rounded education, fostering both personal and academic growth.

The real estate market in Monticello is as diverse as its residents. From charming historic homes that tell the story of the town’s past to modern residences that cater to today’s lifestyle, there’s something for everyone. Whether you're a first-time homebuyer or looking to downsize, Monticello offers an array of options to suit your needs.

In addition to its educational offerings, Monticello boasts a variety of parks, local shops, and dining options, creating a vibrant community atmosphere. Enjoy leisurely strolls through the quaint downtown area or explore the beautiful natural surroundings that Jefferson County has to offer.

Discover the charm of Monticello, where history meets modern living, and let this delightful town become the backdrop for your next chapter. Come home to Monticello today!

Newest Monticello Homes with Jefferson County K-12 School High School

$39,900
403422 MLS
Discover the perfect spot to build your dream home or weekend getaway on this 1.91-acre property in Monticello! Featuring paved road frontage, a partially cleared homesite, and plenty of room to enjoy the surrounding natural beauty, this property offers the ideal balance of privacy and convenience. Located with easy access to both Monticello, FL and Thomasville, GA, you’ll enjoy peaceful country living while remaining close to shopping, dining, and everyday amenities. Don’t miss this great opportunity to own your piece of North Florida! No Mobile Homes Allowed. Additional 1.91 acres also available.

76 BARNES Road, Monticello
$175,000
403421 MLS
37 ACRES, AUCILLA RIVER HUNTING TRACT NEAR MONTICELLO. FL. Fronts on US 90 ½ mile west of the Aucilla River—perhaps the most prolific wildlife corridor in the county. The NE half of the property is an extension of the river’s drainway and borders SRWMD land on two sides--great wildlife habitat. The SW half along US 90 and Gramling Road is composed of a soil type (Plummer) suitable for planted pines or clearing for pasture. It has a decades-old stand of mature pine timber. There is a potential 1-acre site on the highway near Gramling Road that is out of the mapped river floodplain and should be suitable for a residential structure. Tie up this property NOW and be ready for the opening of gun season on Nov. 7.

Vacant E Washington Highway, Monticello
$915,000
3 Beds ⋅ 3 Baths ⋅ 403395 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
$919,000
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
$95,000
403343 MLS
Vacant building lot; inside the city limits, city water and sewer are available, all high and dry; very nice neighborhood, no HOA.

450 Oconee Lane, Monticello
$279,000
3 Beds ⋅ 2 Baths ⋅ 402985 MLS
Step into the timeless charm of historic downtown Monticello, Florida, with this unique property offering nearly 2000 square feet of character and endless potential. Located within walking distance of downtown shopping, dining, and community events, this property is perfectly suited for residential living, commercial use, or a combination of both. Featuring beautiful original wood floors, soaring high ceilings, and architectural details rarely found in modern construction. , this historic gem is full of warmth and personality. A spacious covered front porch provides the perfect place to relax and enjoy the charm of one of North Florida's most picturesque downtown neighborhoods. While the property does need maintenance and updating, it presents an outstanding opportunity to restore and personalize a truly special building. Whether you're envisioning a distinctive home , professional office, boutique retail space, gallery, or other business, the flexible zoning and prime location make the possibilities endless. If you've been searching for a property with history, character, and an unbeatable location, this downtown Monticello treasure is ready for its next chapter.

380 N Jefferson Street, Monticello
$41,000
402917 MLS
Welcome to this peaceful 2.5-acre property located in the established Aucilla Forest & Meadows subdivision. This property offers a wonderful opportunity to build your dream home or place a mobile home while enjoying plenty of space and quiet country living. Lot owners may fence their boundaries and graze livestock such as cows, horses, and goats. Although tucked away from the busyness of town, you are still conveniently located approximately 9 miles from I-10, 18 minutes from downtown Monticello, 35 minutes from Tallahassee and 45 minutes from Thomasville, GA. Enjoy the peace and quiet of having your own land while remaining within reach of nearby cities and everyday conveniences. Travel trailers, campers, motor homes, and tents are allowed on the lot for up to 90 days per year. If a permanent dwelling exists on the lot, you are allowed to park/keep a travel trailer or motor home indefinitely. Road Maintenance: Subject to annual road maintenance and capital improvement assessments. Don't miss your opportunity on this one.

N Forest Court, Monticello
$800,000
4 Beds ⋅ 3 Baths ⋅ 402860 MLS
Some homes are built. Others are curated. This extraordinary custom residence was thoughtfully constructed in 2006 to capture the timeless elegance and craftsmanship of a grand estate from the early 1900s, blending historic charm with modern convenience on five picturesque acres shaded by mature pecan trees. From the moment you arrive via the long paved driveway, you'll be captivated by the home's stately presence and expansive front porch, where six custom, hand-built French doors welcome natural light into the interior. Inside, every detail tells a story—from antique-sourced doors and lighting fixtures to stunning stained-glass interior windows salvaged from a historic New Orleans bank. Designed for both everyday living and entertaining, the home features a formal entry, elegant formal dining room, private library/office, custom kitchen cabinetry, and abundant storage throughout. The spacious primary suite offers a true retreat with an oversized walk-in closet, luxurious bath, and a separate flex room ideal for a nursery, private office, fitness room, or sitting area. Upstairs, a large bonus room easily serves as a fourth bedroom or additional living space. Outdoor living is equally impressive with a screened back porch, charming side porch with brick patio, beautifully established rose bushes and hydrangeas, and a rear-entry two-car garage. Adding to the property's unmistakable character is an original one-room schoolhouse, a rare and fascinating piece of local history that makes this estate truly unlike any other. Rich in architectural character yet built with the reliability of modern construction, this remarkable home offers all the romance of 1906 craftsmanship without sacrificing the comforts of a home built in 2006. A rare opportunity to own a property unlike anything else on the market.

728 Turney Anderson Road, Monticello
$109,000
402857 MLS
Mobile-home-friendly property with a cleared homesite and an existing well, septic system, and electrical service already on the property. Seller financing is available. Conveniently located near I-10 and approximately 30 minutes from Tallahassee. Bring your home plans and enjoy a quiet country setting with room for animals, gardening, outdoor projects, and additional storage. Fence the property and create the private rural lifestyle you have been looking for while remaining close to shopping, dining, and other conveniences.

130 Sweetfield Road, Monticello
$185,000
3 Beds ⋅ 2 Baths ⋅ 402731 MLS
Welcome to peaceful country living in the quiet community of Wacissa, Florida! Nestled on 3.38 beautiful acres, this 3-bedroom, 2-bathroom home offers the ideal opportunity for anyone dreaming of a hobby farm, homestead, or simply extra space to enjoy the outdoors. Designed with both comfort and functionality in mind, the 1,680-square-foot home features a desirable split floor plan, separating the primary suite from two guest bedrooms and a shared bath. The spacious kitchen offers abundant cabinetry, a breakfast bar, breakfast nook, and plenty of room for a large dining table—perfect for family meals or entertaining guests. The open living room is filled with natural light and opens through sliding glass doors to the enclosed back porch, creating the perfect place to enjoy your morning coffee while overlooking the property. Recent improvements include luxury vinyl plank flooring throughout most of the home, with only the two bedrooms remaining carpeted. While some updates and repairs may be needed, the home is move in ready allowing you the opportunity to add your own personal style. An indoor laundry room provides everyday convenience, with additional laundry hookups available on one of the enclosed porches. The true highlight of this property is the incredible outdoor setup. Already established for country living, the land features multiple fenced and cross-fenced areas that are ideal for separating livestock or creating rotational grazing pastures. Whether you're raising chickens, goats, sheep, pigs, or other farm animals, the infrastructure is already in place to help bring your mini-farm vision to life. Several outbuildings provide excellent flexibility for equipment storage, workshops, feed rooms, or hobby spaces. Existing chicken coops, livestock shelters, and a cook shed offer endless possibilities for homesteading or expanding your agricultural pursuits. A small stocked pond attracts deer and other wildlife, adding to the peaceful setting and providing a picturesque backdrop for everyday life. The pond is stocked with fish to offer plenty of catch and release days and entertainment for all watching the fish come up to be fed in the hoop area. The property features two wells for irrigation needs, but the home is serviced by city water. Enjoy the privacy and tranquility of rural North Florida without sacrificing convenience. Located just 20 minutes south of Monticello and approximately 30 minutes from Tallahassee, this property offers the perfect balance of quiet country living with an easy commute to shopping, dining, and employment. Whether you're looking to start a homestead, establish a hobby farm, or simply enjoy wide-open spaces with room to grow, this unique Wacissa property is ready to make your country living dreams a reality.

304 Limestone Road, Monticello
$949,000
3 Beds ⋅ 3 Baths ⋅ 402573 MLS
One or more photos are enhanced. 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
$125,000
402606 MLS
Back on the market - Discover the perfect place to build your dream home on this beautiful nearly 6-acre parcel! Enjoy the peace and privacy of country living with the convenience of being just minutes from the interstate and a short drive to Tallahassee. With plenty of room for your custom home, workshop, gardens, or recreational space, the possibilities are endless! Whether you’re looking to create your forever home or invest in land with an ideal location, this is an opportunity you won’t want to miss. Come experience the freedom and potential this exceptional property has to offer!

Eastwood Road, Monticello
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