Monticello Real Estate

Monticello Real Estate

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 delightful blend of small-town charm and Southern hospitality. With a population of just over 2,500 residents, this quaint city boasts a close-knit community where neighbors become friends and local businesses thrive.

Monticello is steeped in history, with its roots dating back to the early 19th century. As you stroll through the historic downtown area, you’ll be captivated by the beautifully preserved architecture, including the iconic Monticello Opera House and the Jefferson County Courthouse. The city is also home to a variety of antique shops, boutiques, and cozy cafes, perfect for a leisurely afternoon of exploration.

Nature enthusiasts will find Monticello to be a paradise, surrounded by lush forests and serene landscapes. The nearby Aucilla River and the Apalachicola National Forest offer endless opportunities for outdoor activities such as hiking, fishing, and kayaking. The region’s mild climate allows residents to enjoy these natural wonders year-round.

In addition to its natural beauty, Monticello hosts a variety of community events and festivals that celebrate its rich culture and heritage. From the annual Watermelon Festival to farmers' markets, there’s always something happening that brings the community together.

Whether you’re considering a move or simply looking for a weekend getaway, Monticello, FL, offers a peaceful retreat with a strong sense of community, making it a wonderful place to call home. Come discover the charm of Monticello—where history meets hospitality!

Newest Listings in 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
$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
$225,000
403342 MLS
Commercial lot, good location, great zoning, cleared, surveyed.

36 Shiver Road, Monticello
$279,000
403115 MLS
A piece of history in historic downtown Monticello. Tremendous charm for an office, retail store or combination home office.. Walk to downtown shops and restaurants. Spacious front porch overlooks picturesque downtown.

380 N jefferson Street, 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
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