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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
465 Crooked Creek Lane, Monticello
$469,900
3 Beds ⋅ 2 Baths ⋅ 405605 MLS
Beautifully appointed and move-in ready, this nearly new three-bedroom, two-bath home with a dedicated home office offers elevated style, thoughtful upgrades, and exceptional indoor-outdoor living, all just minutes from the charm of historic Monticello. The private office features custom wood detailing, creating a distinctive and inviting workspace separate from the home’s three spacious bedrooms. Inside, carefully selected designer paint colors, custom wall details, upgraded lighting, French pantry doors, cordless bamboo blinds, and stylish cabinet and door hardware give the home a polished, custom feel. The beautifully designed kitchen is anchored by a large center island overlooking the main living area, creating an effortless flow for everyday living and entertaining. A wood-burning fireplace adds warmth and character to the heart of the home. The luxurious primary suite is a true retreat, featuring a beautifully finished bath with a large walk-in shower, soaking tub, generous walk-in closet, and elevated finishes throughout. Spacious guest bedrooms provide comfortable accommodations for family and guests. Outside, the large, privacy-fenced backyard offers plenty of room to relax, entertain, and enjoy the outdoors. Thoughtful landscaping, a flagstone walking path, and outdoor fire pit create a welcoming backyard setting with privacy and room to make it your own. Meticulously maintained and truly move-in ready, this home combines the ease of newer construction with the warmth, character, and designer details that make a home feel anything but ordinary.

465 Crooked Creek Lane, Monticello
1410 E Pearl Street, Monticello
$385,000
4 Beds ⋅ 2 Baths ⋅ 405602 MLS
Classic 1926 Craftsman in Beautiful Monticello, Florida. Step into the timeless charm of this beautiful home offering more than 2,700 square feet of heated and cooled living space and approximately 3,248 square feet under roof. Set on a spacious one-acre lot, this distinctive home combines historic character, generous living spaces, and the convenience of small town living. Inside, you'll find high ceilings and large, inviting rooms throughout, along with beautiful architectural details that give the home its warm and gracious character. The heart of the home is a large eat-in kitchen, complemented by a formal dining room and spacious living room perfect for cozy evenings and entertaining. A bright and welcoming sunroom overlooks the established grounds, creating a peaceful space to enjoy morning coffee, afternoon reading, or the changing seasons. Outside, the expansive one-acre setting offers plenty of room to enjoy the mature, well-established landscape. A convenient porte-cochere provides covered parking and adds to the home's classic architectural appeal . You can even ride your golf cart to nearby dining and shopping , making it easy to enjoy the community, while still coming home to the privacy and spaciousness of you own beautiful grounds.

1410 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
205 Crooked Creek Lane, Monticello
$564,900
3 Beds ⋅ 2 Baths ⋅ 405271 MLS
Welcome to this beautiful one-owner home in highly sought-after Crooked Creek, located just at the edge of town in Monticello, Florida. Built in 2021 and offering over 2,000 square of living space, this meticulously maintained home is truly turnkey. Set on an impressive.76-acre lot, the property offers exceptioanl privacy and outdoor living. The beautifully fenced backyard features a sparkling in-ground pool with fountain., creating the perfect setting for relaxing, entertaining, and enjoying Florida's beautiful weather. Inside, the home offers a desirable open floor plan with plenty of natural light and a warm, inviting feel. One of the home's standout features is the lovely sunroom overlooking the pool and backyard, providing a peaceful space to enjoy your morning coffee or unwind at the end of the day. PROPERTY HIGHLIGHTS: Whole House Generator, Pool, Fenced Backyard. ADJOINING .70 ACRE LOT AVAILABLE FOR PURCHASE.

205 Crooked Creek 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
535 Holly Road, 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
2462 Lloyd Creek Road, Monticello
$529,999
3 Beds ⋅ 2 Baths ⋅ 404670 MLS
Rare opportunity to own a fully operational 20-acre working farm in the beautiful North Florida countryside. This property is currently home to both dairy cows and goats and is set up for continued agricultural use with multiple fenced pastures, established and lush Argentine Bahia grass, a milking barn, livestock holding area, and additional farm infrastructure. The property includes a 2018 three-bedroom, two-bath mobile home offering comfortable living while you work the land. The thoughtfully laid-out acreage provides multiple pastures and plenty of room for livestock, making this an ideal setup for a dairy operation, small cattle or goat farm, hobby farm, homestead, or agricultural investment. From the established pastures to the existing livestock facilities, much of the hard work has already been done. Bring your animals, continue the existing operation, or create your own vision for a productive North Florida homestead. Located along Lloyd Creek Road in the Monticello area, this property offers the opportunity to enjoy rural living while remaining within reasonable reach of Tallahassee and surrounding communities.

2462 Lloyd Creek Road, 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
107 Tarn Way, 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
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
1605 Sweetbay Court, 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
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
78 Fen Court, Monticello
$470,000
3 Beds ⋅ 2 Baths ⋅ 403824 MLS
Photos of previous homes. Come choose all your finishes and upgrades. Home is just finishings the framing stage of construction. Amazing new construction 3 bedroom 2 bathroom by Nailed It Tallahassee LLC. Luxurious master suite, Kitchen made of dreams, this is a must see!

78 Fen Court, Monticello
195 Coopers Pond Road, Monticello
$325,000
3 Beds ⋅ 2 Baths ⋅ 403529 MLS
Wonderful family home in great neighborhood~Located on a quiet street, this home sits on a full acre and is ready for new owners~huge walk-in shower~breakfast nook~jetted tub in 2nd bathroom~walk-in closet in master~screened porch overlooking private backyard~partially fenced~2-car garage~nice yard with large oaks ~~Zero turn lawnmower included with acceptable offer~~

195 Coopers Pond Road, Monticello
947 Piney Woods Road, Monticello
$325,000
4 Beds ⋅ 2 Baths ⋅ 402384 MLS
Seller is offering $5000 toward closing costs! Charming 2022 Mobile Home on 5 Peaceful Acres A rare blend of modern comfort and wide-open space, this 2022 mobile home sits on 5+ acres—perfect for anyone craving privacy, freedom, and room to grow. Whether you dream of a hobby farm, a quiet country retreat, or simply a place with no close neighbors, this property delivers. Embrace freedom of country living with the convenience of a modern home. Wake up to quiet mornings and build the lifestyle you’ve always wanted. A short 5-minute drive to historic Monticello’s downtown for shopping, restaurants and local butcher and farmers markets. Small town / rural living at its best. Convenient to Tallahassee, Monticello, Perry and Thomasville. This home features a bright, open-concept living area with contemporary finishes. Enjoy your spacious kitchen with ample cabinetry, large pantry and modern appliances. Comfortable bedrooms and well-appointed bathrooms complete this move in ready home. Underground utilities include community water, electric and Century Link WiFi! You'll have plenty of space for gardens, animals, workshops and future expansion!

947 Piney Woods Road, Monticello
1565 Sweetbay Court, 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
855 S Waukeenah Street, Monticello
$424,900
4 Beds ⋅ 3 Baths ⋅ 402136 MLS
Stunning New Construction recently built by Southern Construction. Centrally located in downtown Monticello, with mature landscaping, and plenty of room for the family. This 4 bed and 3 bath home features vinyl plank flooring, granite countertops, walk in tile shower and tub in master, upgraded trim package, and stainless appliances. Nice large back porch with deck, over looking the large beautiful back yard!! Come see all this home has to offer today!!

855 S Waukeenah Street, Monticello
2664 W Washington Highway Unit Two Homes, Monticello
$425,000
401409 MLS
Two houses perfect for generational living or rental income. These move-in-ready homes are in good condition, convenient to Monticello while maintaining privacy. The larger home is a 1550's era brick ranch-style home that is well maintained with newer roof (2022), new electric (2025), new plumbing (2025), tankless water heater and whole house generator. The main living area is 2,659 sf with 5 bedroom and 2 full bathrooms. There's also a sunroom, and a 396 sf attached bonus room suitable for an office or workshop, plus 3 small outbuildings, one with working electric. The guest house includes 3 bedrooms and 2 bathrooms. Built in the 1950's, it's functional but not fancy. It is in good condition with newer roof, plumbing (2025), and electric (2025). Both homes have a fresh coat of paint. The houses are on 2 separate contiguous parcels (1.3 ac and 0.64 ac) but are being offered together. A great housing buy for someone looking for a lot of living space.

2664 W Washington Highway Unit Two Homes, Monticello
2664 A W Washington Highway, Monticello
$325,000
5 Beds ⋅ 2 Baths ⋅ 401408 MLS
FULLY RENOVATED SPACIOUS HOUSE, 1.3 acres, on picturesque US 90 near Monticello. This move-in-ready home in good condition is a 1950’s era brick ranch-style home with new plumbing, new electric, fresh paint, new roof, and a whole home generator. The main living area is 2,659 sf with a unique two levels. 5 bedrooms and 2 baths with plenty of character, including the "Captain's Room" with built-in drawers and cubbies. There’s also a 396 sf bonus room suitable for an office or workshop, plus 3 small outbuildings, one with power. Super location just 3 miles west of charming Monticello on beautiful U.S. 90; only 19 minutes from Tallahassee Amazon facility and Publix/Vineyard at I-10. Secluded due to natural vegetation, yet convenient to town.

2664 A W Washington Highway, Monticello
285 Mallard Lane, Monticello
$429,000
3 Beds ⋅ 2 Baths ⋅ 401255 MLS
*Jefferson County peaceful country living with a waterfront backdrop! Built in 2008, this well maintained 3 bedroom, 2 bath home sits on 4.89 beautifully (mostly cleared) acres offering privacy and natural beauty backing directly up to Lloyd Lake- perfect for relaxing evenings with scenic views. Pretty rocking chair front porch as well as a screened in back porch with a propane hookup for grilling and generator hookup. This split plan offers a large primary suite with dual vanities, large walk in shower w/separate soaking tub and large walk in closet. Other features include LVP wood flooring, wood burning fireplace, tankless water heater, an indoor laundry room, ceiling fans, alarm and water softener. Convenient outdoor storage w/2 tool sheds- one w/ power hook up.

285 Mallard Lane, Monticello
1550 Tennessee Street, Monticello
$200,000
3 Beds ⋅ 2 Baths ⋅ 400858 MLS
Charming and affordable home on the North side of Monticello in Nobles Subdivision. 3 BR 1.5 Baths. Upgrades in 2021 include new ac, new water heater, new roof. Recent interior paint. Large fenced backyard.

1550 Tennessee Street, Monticello
1070 Partridge Lane, Monticello
$298,900
3 Beds ⋅ 2 Baths ⋅ 400806 MLS
Currently under construction. Interior pictures are from a previous model home. Approximately 60 days until completion. Home qualifies for USDA financing.

1070 Partridge Lane, Monticello
480 S JEFFERSON Street Unit -, Monticello
$364,900
400229 MLS
Located in the heart of Monticello, this 5-unit investment property offers a prime opportunity for investors looking to add value and generate income. Positioned just minutes from local businesses, shopping, dining, and convenient interstate access, the location provides strong appeal for tenants seeking both convenience and accessibility. Currently, 3 of the units are occupied, providing immediate rental income, while the remaining 2 units are vacant and present an excellent value-add opportunity. Both vacant units are 1-bedroom, 1-bath units that need updating and repairs to become rent-ready, allowing the next owner to renovate and increase overall cash flow potential. Total Bedroom Count is 6 bedrooms and 5 bathrooms. Whether you are looking to expand your investment portfolio, renovate for increased returns, or capitalize on the growing demand for rental housing in Monticello, this property offers strong upside potential in a desirable in-town location.

480 S JEFFERSON Street Unit -, Monticello