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

$175,000
2 Beds ⋅ 1 Baths ⋅ 405104 MLS
If you are looking for your opportunity, this home's for you! This 1950's bungalow is within reach for all. Whether a first time buyer, down-sizer, or investor, this home has ample opportunity for all! At a price where designer re-dos and renovations are possible, anyone can can make this dream come true! The huge addition (500+ sqft) off the rear of the home offers ample square footage that could possibly be reconfigured to a new owner's desires. The original home features a two bedroom one bath floor plan. The kitchen is sandwiched between two large living areas making opportunities for renovations and modernization ideal. With a third acre that's fully fenced, existing dog kennel, and a true garage, this property has built in bonuses in addition to the stellar location just moments away from Monticello's town center, access to I-10 and Hwy90 for easy commutes. Monticello is still known for its downtown charm and community events and connectedness. Just check out the chamber's facebook page! :D In addition to the Ecological Park and Legion right across the street, the house is minutes from town square where you can enjoy entertainment at Old Monticello Opera House, Vintage Stores, Restaurants. And if you wanted to, the Aldi and DG Market are walking distance to the home! So if you are looking for true potential not just in making a home, but making and enjoying community, see what 1060 S Water Street has to offer in charming Monticello, Florida!

1060 S Water Street, Monticello
$249,000
3 Beds ⋅ 2 Baths ⋅ 404983 MLS
Discover this charming 3-bedroom, 2-bath home, ideally located just off Mahan Road and conveniently close to Downtown Monticello. Featuring a vaulted living room and cozy gas fireplace, this residence offers a welcoming and spacious atmosphere. The large fenced-in yard is perfect for pets and outdoor gatherings. The master suite is generously sized for comfort. Additional highlights include a single-car garage and plenty of room for your personal touch. Don't miss the opportunity to make this lovely home yours!

30 PINE NEEDLE TRCE, Monticello
$254,900
3 Beds ⋅ 2 Baths ⋅ 404967 MLS
New construction; very convenient to downtown; house is close to completion.

360 Bowman Street, Monticello
$357,000
3 Beds ⋅ 2 Baths ⋅ 404878 MLS
Wonderful Cottage Home in Quaint Crooked Creek Subdivision in Monticello Florida. Open Floor Plan with 3 Beds/2 Baths. Tiled Covered Front Porch with a Large Tiled Screened Porch and Deck for Grilling. There is a Built in Storage Shed approx. 4x7. Spacious Garage with Shelves. Additional 30Amp for RV with Parking Space Designed for RV or could be used for Additional Parking. Landscape is Beautiful and Creates Privacy from Streetside and Privacy Fence with Jasmine in the Backyard. Adorable Home, Perfect for Small Family or Retiree!

535 Holly Road, Monticello
$895,000
3 Beds ⋅ 3 Baths ⋅ 404823 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
$115,000
3 Beds ⋅ 2 Baths ⋅ 404606 MLS
Calling all investors, house-flippers, and handy homewoners! Fix & Flip for cash or hold for rental income. Located just 3 minutes from downtown Monticello and 30 minutes to Tallahassee. This 1968 two-story home is built on concrete blocks (1st story), & sits on a large 0.38-acre lot with mature vegetation for privacy on 2 sides. Has a metal roof (unknown age), HVAC~ 2020. Utilities are on for showings. Priced for an AS-IS sale, including any bulk junk left from tenants. Exterior stairs are unsafe. Do not use.

1420 Tennessee Avenue, Monticello
$429,900
3 Beds ⋅ 2 Baths ⋅ 404440 MLS
Experience a nearly new construction with this stunning 3-bedroom, 2-bathroom home crafted by Nailed It Tallahassee LLC. Featuring a luxurious master suite and a dream kitchen, this property is a must-see. It includes plantation shutters and remote-controlled blinds throughout. Enjoy the privacy of a fenced-in backyard. Move-in ready!

107 Tarn Way, Monticello
$175,000
3 Beds ⋅ 2 Baths ⋅ 404538 MLS
AFFORDABLE OLD MONTICELLO (FL) HOME. Spacious, good condition, move-in-ready. Convenient, easy walk to charming downtown. Recent basic repairs and renovations (roofing, electrical, plumbing, etc). Old but very livable, with a flexible floor plan. Four possible bedrooms, two baths. Recent central heat and air. Large deck equipped with a hot tub (unknown condition) and fenced. Handicap ramp. Huge two-story storage shed. Spacious lot. This early 1900s home is still very livable and very affordable, with lots of potential to add upgrades and value.

520 E High Street, Monticello
$360,500
3 Beds ⋅ 2 Baths ⋅ 404500 MLS
Construction has begun. 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. Propane appliances and Rinnai Tankless Water Heater.

1605 Sweetbay Court, Monticello
$700,000
3 Beds ⋅ 3 Baths ⋅ 404453 MLS
Set on 18+ acres of beautifully maintained pasture, this private country property is built for both everyday living, true equestrian use or small livestock farm. The land is the star- fully fenced with new wood fencing that cleanly defines multiple pastures, a peaceful pond, and wide open space to ride, graze and enjoy. The 6-stall horse barn is ready to work with paddocks attached to each stall, rubber mats, LED lights and stall fans installed recently, a large tack room and wash racks. This an ideal setup for anyone looking for a functional, turn-key horse property. The home itself is in excellent condition and thoughtfully laid out, with a spacious living room anchored by a large fireplace, a kitchen with bar seating, breakfast nook and new appliances and a separate formal dining room. Every room has a beautiful view of the farm surrounding it. Wood floors run throughout the main living areas, adding warmth and character, while all bedrooms and office are tucked upstairs for a quiet retreat. A new 2024 roof and fully repainted interior, adds peace of mind. Enjoy sweeping views of the surrounding countryside and a true sense of privacy, all while being conveniently located to both Tallahassee and Thomasville. This is a property you don't want to miss!

660 Whispering Hills Road, Monticello
$299,900
3 Beds ⋅ 2 Baths ⋅ 404317 MLS
Great opportunity to be in the lovely town of Monticello off of Pearl Street. Acre lot & Concrete swimming pool with this single story home. Large rooms, hardwood floors throughout much of the house, updated kitchen cabinetry, large detached garage. House has been cleaned up & some fresh painting done but does need work and is priced accordingly. Being sold AS-IS w/right to inspect.

515 Sunset Drive, Monticello
$695,000
5 Beds ⋅ 3 Baths ⋅ 403842 MLS
Just 3 miles south of Monticello, FL and only 2.5 miles from I-10, this 10.45 acre working homestead has been thoughtfully set up for country living, livestock and extended family. The 3,536 sq. ft. home features 4 bedrooms/2 baths in the main house (with the set up for an additional bath upstairs) master is conveniently located downstairs with two walk-in closets, private access, plenty of lighting and a huge newly renovated bathroom, whirlpool tub in spare bath, high ceilings in the living area with a wood burning fireplace, bright beautiful kitchen with corrian counter tops, new dishwasher, new stovetop and french doors leading to the best views of the back of the property. This exceptional property also includes a private one bedroom, one bath mother in law suite with its own private entrance, connected to the main home by an enclosed breezeway (initially set up for a small hair salon business). The suite offers a large living area, new step in shower, new refrigerator, kitchen sink, microwave even their own back porch! Ideal for a parent, grown child, guests or simply someone who needs a little independence while staying close to family. Outside is where the property really earns the name farmstead. Six fenced paddocks (Bekaret 4ft high tensile sheep and goat fence) along with "no climb fencing in the back yard for the dogs. Pines, crape myrtles, beautiful live oaks run on the back side of the house providing ample shade for livestock. There is a three bay pole barn (25x30), equipment shed/potting house (15x50), additional equipment barn (25x60), chicken coop (10x16), peach trees and blueberry bushes, plus plenty of room to continue growing, gardening and raising animals. New pitcher pump well provides access to water even when the power is out with the option to hook up to community water. Water is ran to EVERY pasture clear up to the main road! The property is gated with Ghost Controls, fenced and has excellent frontage on Waukeenah Highway. Best of all, there is no HOA and no deed restrictions to tell you how to use your own 10.45 acres. This insn't just a house with acreage. It's an established country homestead with the infrastructure already in place and close enough to town for conveniences. Most everything on the property is negotiable...including tractor with attachments, chickens, as well as other equipment and furnishings.

2247 Waukeenah Hwy, Monticello
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