Monticello Homes under $350,000

Monticello Homes under $350,000

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Newest Monticello Homes under $350,000

1195 E PEARL Street, Monticello
$274,500
2 Beds ⋅ 1 Baths ⋅ 405614 MLS
Come check out this sweet cottage nestled in charming Monticello! This 1947 property is ready for the next chapter of its distinguished journey. Move in ready with tons of updates including recent kitchen appliances, HVAC and hot water. Tucked in on desirable Pearl St this house lives bigger than it looks with open kitchen, dining and living spaces. Sip coffee in the mornings under your very own century oak tree! Walking distance to historic Monticello’s downtown for shopping, restaurants and local butcher and farmers markets. Small town living at its best, but convenient to Tallahassee and Thomasville.

1195 E PEARL Street, Monticello
620 S Jefferson Street, Monticello
$179,000
1 Beds ⋅ 1 Baths ⋅ 405565 MLS
Discover the charm and versatility of this cozy cottage style home conveniently located on S. Jefferson Street in Monticello, Fl. Zoned B2 Business use, this property offers flexibility for both personal use and potential business opportunities. The home features one bedroom and one bathroom, a cozy kitchen, and a large open living/family/dining room that creates a comfortable, inviting space for relaxing or entertaining. Private backyard is perfect for enjoying outdoors with good space for grilling and relaxing. With its cottage charm, flexible zoning, convenient location, and private outdoor space, this property offers a unique opportunity for a homeowner, investor, or entrepreneur looking for a property with character and potential. BROKER/OWNER

620 S Jefferson Street, Monticello
380 Poplar Street, Monticello
$175,000
3 Beds ⋅ 1 Baths ⋅ 405416 MLS
Situated on over half an acre and within walking distance of charming downtown Monticello, this carefully maintained home offers great bones, plenty of space, and so much potential to make it your own. The fully fenced yard is lined with mature greenery, creating a wonderful sense of privacy while still giving you plenty of room to enjoy the outdoors. Inside, you’ll find an open kitchen, living, and dining area, plus a large separate family room perfect for entertaining, hosting family and friends, or creating an additional flex space. A two-car carport provides covered parking, while a ramp to the entrance offers easy accessibility. Major updates include a 2014 roof and 2016 HVAC, water heater, and windows. The home also features an up-to-date WDO bond and a CLEAR 4-point inspection. With a little updating and your personal touch, this property has incredible potential to become something truly special! Buyers to verify dimensions.

380 Poplar Street, Monticello
190 Serenity Lane, Monticello
$339,000
4 Beds ⋅ 2 Baths ⋅ 405361 MLS
Check out this extra-spacious home featuring over 2000 sq ft of comfortable living space! The home includes a large master suite with a sitting area, spacious living room, separate family room with a cozy fireplace, and a large kitchen with island. The property also features an impressive 1,600 square-foot concrete-floor garage/workshop, offering plenty of space for vehicles, equipment, hobbies, storage, or a home-based project. Cozy chicken coop adds even more versatility for those looking to enjoy a little country living. Located with an easy commute to Tallahassee and Florida's state capital. PRICE INCLUDES JOHN DEER TRACTOR AND ATTACHMENTS, JOHN DEERE ZERO TURN MOWER AND EQUIPMENT TRAILER.

190 Serenity Lane, Monticello
1060 S Water Street, Monticello
$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
30 PINE NEEDLE TRCE, 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
360 Bowman Street, Monticello
$252,500
3 Beds ⋅ 2 Baths ⋅ 404967 MLS
New construction; very convenient to downtown; house is close to completion.

360 Bowman Street, Monticello
1420 Tennessee Avenue, Monticello
$116,500
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 repaired.

1420 Tennessee Avenue, Monticello
520 E High Street, 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
515 Sunset Drive, 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
490 N Cherry Court, Monticello
$249,000
2 Beds ⋅ 2 Baths ⋅ 404023 MLS
This is the kind of home you can move into and simply enjoy. Located in Cherry Street Square, a desirable community in the heart of historic Monticello, this immaculate two-bedroom, two-bath townhome with a bonus room or office has been thoughtfully updated from top to bottom. The interior feels fresh, bright and completely move-in ready, with luxury vinyl plank flooring, updated doors and windows, modern hardware and fixtures, and a full suite of kitchen appliances, all completed in 2022. Since then, the owners have continued improving the home with new gutters, toilets and faucets, an insulated garage door, storm door, smoke and carbon monoxide detectors, updated electrical switches and outlets, a new water heater, kitchen faucet and roof. The enclosed screened porch was added in 2025, creating a comfortable place to enjoy your morning coffee or unwind at the end of the day. A one-car garage, private driveway and back patio provide the space and convenience that can be difficult to find in townhome living. The HOA handles the yardwork and fence maintenance, giving you more time to enjoy your home—and far less time worrying about upkeep. From Cherry Court, you can walk or bike beneath Monticello’s canopy-lined streets to locally owned restaurants, coffee shops, boutiques, antique stores, craft shops and outdoor sporting stores. Downtown is centered around its historic courthouse and filled with preserved architecture, including the Monticello Opera House, giving the town a character that feels distinctly different from anywhere else in North Florida. It offers a slower pace without feeling disconnected, with Tallahassee approximately 25 miles away. Immaculately maintained, extensively updated and positioned in one of Monticello’s most convenient communities, this home offers an opportunity to simplify without sacrificing comfort, quality or location.

490 N Cherry Court, Monticello
112 Long Leaf Drive, Monticello
$250,000
3 Beds ⋅ 2 Baths ⋅ 403825 MLS
Nearly 6 Acres of Opportunity in Beautiful Monticello! If you're looking for space, privacy, and the possibility to create a home that truly reflects your vision, this property is it! This spacious 3-bedroom, 2-bathroom modular home offers a desirable open and split floor plan with generously sized living spaces. The expansive primary suite provides a private retreat and features a walk-in closet, dual vanities, and a separate shower. Just off the primary suite, a separate living room with a wood-burning fireplace creates a warm and inviting space to relax and unwind. The home also offers a spacious kitchen, separate dining room, and a large indoor laundry room. Step outside from the dining room to enjoy the natural, flat backyard and the privacy that nearly 6 acres provides. With plenty of room to spread out and enjoy the peaceful surroundings, this property offers an exciting opportunity for someone looking to add their personal touches and create something special. Whether you're dreaming of a private country retreat, room for hobbies and outdoor activities, or simply more space to enjoy, this Monticello property offers the land, layout, and potential to make it your own.

112 Long Leaf Drive, Monticello
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