Monticello Homes for Sale

Monticello Homes for Sale

Welcome to Monticello, Florida – a hidden gem nestled in the heart of Jefferson County! Known for its rich history and charming Southern hospitality, Monticello offers a unique blend of small-town charm and modern conveniences. With its picturesque oak-lined streets, historic buildings, and vibrant local culture, Monticello is a place where community spirit thrives.

As you explore this delightful city, you'll find a variety of recreational activities, from hiking in the nearby Apalachicola National Forest to enjoying a leisurely afternoon at one of the local parks. Monticello is also home to a thriving arts scene, with local galleries and events that showcase the talents of its residents. The city’s downtown area boasts an array of quaint shops, delightful eateries, and warm, welcoming locals, making it an ideal spot for both visitors and residents alike.

For those looking to make Monticello their home, there are numerous homes for sale that cater to a variety of tastes and budgets. Whether you’re seeking a charming historic home with character or a modern residence with all the latest amenities, Monticello has something for everyone. With its affordable housing market and serene surroundings, it’s no wonder that more people are choosing to call this enchanting city home.

Discover the beauty and warmth of Monticello, Florida, where your dream home awaits! Explore the available listings today and take the first step toward embracing the vibrant lifestyle this community has to offer. Welcome to your new beginning in Monticello!

Newest Monticello Homes for Sale

$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
$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
$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
$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
$235,000
3 Beds ⋅ 1 Baths ⋅ 402594 MLS
Step back in time and discover the charm of this classic Monticello home, offering timeless character and endless possibilities. Built in 1915, this Craftsman-style residence features 1,700 square feet of living space with hardwood floors, separate living and dining areas that reflect the home's historic appeal, 3 full bedrooms, with a large mud room and separate sitting room, a wood-burning fireplace in the living room and primary bedroom, soaring ceilings, and charming details throughout. Situated on a spacious .23 acre in-town lot, the property offers convenient access to Monticello's historic downtown, where you'll enjoy locally owned shops, dining, and community events. The spacious backyard is fully fenced, with a large deck, 2-car garage/workshop, a chicken coop, and plenty of room for the kids and pets to play. Whether you're looking to restore a piece of Jefferson County history or simply appreciate the quality craftsmanship and sturdiness of a home that was built to last, this home presents a wonderful opportunity to make it your own.

810 E Dogwood Street, Monticello
$337,000
4 Beds ⋅ 2 Baths ⋅ 402551 MLS
Escape to your own private 5-acre retreat! A long, secluded driveway leads to this charming cottage-style 4-bedroom, 2-bath home surrounded by the natural beauty of North Florida. Enjoy the peace and privacy you've been dreaming of with no HOA and no flood insurance required. The thoughtfully designed floor plan features a spacious primary suite and two additional bedrooms on the main level, while upstairs offers a fourth bedroom and an oversized flex room—perfect as a 5th bedroom, home office, playroom, or home gym. The primary suite includes a walk-in closet, double vanity, garden tub, and separate shower. A brand-new roof, two-car carport, and storage shed add to the home's appeal, while the peaceful setting feels worlds away from it all. Yet you're less than 2 miles from I-10 and only 15 minutes from the shops, restaurants, and historic charm of downtown Monticello. If you've been searching for privacy, space, and the freedom to enjoy country living without sacrificing convenience, this is the one.

4081 Gamble Road, Monticello
$365,000
3 Beds ⋅ 2 Baths ⋅ 402445 MLS
Only minutes east of Tallahassee, nestled in 5 beautifully wooded acres, this impecably maintained and freshly painted home is the perfect getaway for peaceful rural living. A massive living room with dramatic vaulted ceiling and windows that let you experience all the natural surroundings. The kitchen features double wall ovens + cooktop. A tall pole barn for storing equipment is large enough for an RV. A power inlet box allows you to plug your generator up to the house during emergencies. A huge sunroom off the back of the house, lets you be outside while staying comfortable. This beautiful house won't last long!

1391 Paul Thompson Road, Monticello
$1,100,000
3 Beds ⋅ 3 Baths ⋅ 402379 MLS
Country Living at Its Finest! This stunning 2,800-square-foot 3-bedroom, 3-bath home is nestled on nearly 30 breathtaking acres. Offering the perfect blend of comfort, beauty, and functionality, this exceptional property is ideal for those seeking peaceful country living without sacrificing modern amenities. Inside, you’ll find spacious living areas with high ceilings, an eat-in kitchen, family room with a wood-burning fireplace, beautiful sunroom and a spacious master suite. This home is equipped with a tankless water heater and a whole-house generator. Step outside to enjoy true outdoor living perfect for entertaining family and friends in the fully equipped outdoor kitchen or unwind year-round on the screened porch featuring a wood-burning fireplace. Whether you’re enjoying quiet mornings or hosting gatherings, this home was designed to embrace the beauty of its natural setting. The property also offers a detached three-car garage complete with a workshop, a pole barn, and ample room for equipment, recreational vehicles, or hobbies. With nearly 30 acres of open space, there’s endless potential for horses, farming, recreation, or simply enjoying the privacy and serenity of your own land. If you’ve been dreaming of a country estate with room to roam, spectacular views, and exceptional amenities, this one-of-a-kind property is ready to welcome you home.

458 Watermill Road, Monticello
$305,000
3 Beds ⋅ 2 Baths ⋅ 402340 MLS
Welcome home to this charming 3-bedroom, 2-bath property set on a spacious lot with a fully fenced backyard. Thoughtfully updated throughout, major improvements include a 2023 metal roof, new HVAC system, new windows, and a new electric on-demand water heater. The renovated kitchen features all new appliances and a clean, modern look. The second full bath is conveniently located just off the rear sunroom, making it ideal for guests or easy access from the backyard and pool area. Outdoors, enjoy a huge yard complete with an above-ground pool, all pool equipment included, a mature blueberry bush, a large shed or workshop, and chicken coops. As an added bonus, the home is being offered with all furniture and yard equipment, including the mower, making this a truly move-in-ready opportunity. Conveniently located on a great street in downtown Monticello with easy access to both Tallahassee and Thomasville.

395 Sunset Drive, Monticello
$254,900
3 Beds ⋅ 2 Baths ⋅ 402231 MLS
New construction; very convenient to downtown; house is close to completion - should be ready in about 45 days.

360 Bowman Street, Monticello
$350,500
3 Beds ⋅ 2 Baths ⋅ 402229 MLS
This home is currently coming out of the permitting phase. New construction will start in the next week. Completion date should be approx 4 months or less. We will update the comments as the construction progresses. Picture is virtual. More to come as construction continues.

1565 Sweetbay Court, Monticello
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