Full of character, this spacious 1950s home offers 4 bedrooms and 3 full bathrooms on a generous 0.60-acre lot in the heart of Monticello. With over 2,200 square feet—including two bedrooms with ensuite baths—it also features flexible zoning for residential, business, or mixed use. The layout includes a cozy living room with a fireplace and an airy sunroom, perfect for an office or casual dining. Tongue-and-groove ceilings run throughout, with coffered details adding charm in the main living and dining areas. Updates include a 2019 roof and 2022 HVAC. French doors open to the cleared back yard with a wood deck—great for entertaining or gardening. A detached one-car garage/workshop and huge side yard offer even more space to enjoy or expand. Located just south of the historic courthouse, this home puts you close to everything Monticello has to offer—restaurants, shops and small-town charm. Bring your golf cart and enjoy an easy ride to it all.
Charming 1955 Cottage in the Heart of Monticello,Fl. Welcome home to this cozy yet surprisingly spacious 3-bedroom 1.5 -bath cottage on beautiful Oak Lined Pearl Street. Just a short walk or golf cart ride to historic downtown Monticello. Features include original hardwood floors, new windows, updated electrical and a sunroom with brick paver flooring- perfect for relaxing with morning coffee. Roomy master suite features French doors leading to master bath, while the cozy den sits at the heart of the home. The 1/2 bath could easily be converted back to a full bath. Outside, you will find a large .66 fenced lot along with storage shed with plenty of space for pets or gardening. Backyard is extra private!
This is an actual sunset over a 15 minute period in mid-October. Experience gorgeous sunsets and serene living at this exceptional single-story, multi-home estate on 15 high-and-dry acres in beautiful Valley View Estates, straddling the Leon and Jefferson County line. **With a NEW Roof prior to closing, the custom-built main residence (~4,000 sq. ft.) offers 12-foot ceilings throughout, an open-concept living, dining, and kitchen area, and seamless access to the screened lanai and pool overlooking open pastures. Three ensuite bedrooms plus two additional rooms—ideal for an office and craft space—offer flexibility and function. Whole Home Generator is perfect for peace of mind! Seller is providing a $25,000 upgrade allowance with acceptable offer!!! ***A second 2-bedroom, 2-bath residence (~1,200 sq. ft.) provides complete independence for guests or multi-generational living. ***The barn includes a second-story loft and an attached 460 sq. ft. efficiency apartment with kitchenette and full bath, while the 660 sq. ft. climate-controlled workshop is perfect for hobbies or creative pursuits. *** Enjoy the life-sized playhouse, peaceful privacy, and panoramic sunset views. Whether you’re seeking a family compound, working farm, or private retreat, this estate delivers space, serenity, and unmatched versatility in one breathtaking property.
Remarkable, peaceful in-town oasis on 3.54 acres! An incredible find in the heart of downtown Monticello, FL. Not only is this home located on a private 3.54 acre spread, surrounded by a perimeter of natural foliage, but the home itself has been beautifully updated, blending the charm of old and the convenience of new. The 3 bedroom/3 bathroom, 2,000+ sq ft home has a kitchen flooded with natural light overlooking beautiful back yard views. The Master Suite is incredibly spacious, with it's own sitting area and/or office space. The Master Bath has a double vanity and tiled walked in shower. The Master also has it's own private, exterior door access. Outdoors, there is a pool house with a lap pool, a commercial grade greenhouse, (2) additional outbuildings (1 with electric/water), a koi pond and beautiful landscaping throughout, with a multitude of gorgeous flowers, planted by a professional gardener/florist, that bloom throughout the year. Hummingbirds are plentiful daily (except during winter) if you keep the feeders full of nectar! Roof (2022) A/C (upgraded, 2021). A must see for sure! **Note: One bedroom (10x10) is not pictured, because it was being used for storage at the time photos were taken. Also: chicken coup (and chickens!) are excluded from the sale, and will be relocated on/before closing.`
2024 construction, shows like brand new home on large .68 acre lot, wooded buffer adds privacy. Open floor plan, kitchen with granite tops, counter seating and dining overlooks living room. Split bedroom plan , large master suite, walk in shower. 2 car garage, back screen porch overlooking privacy fenced backyard.
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.
Built between 1890-1910, this Classic Revival home sits on 1.77 acres along one of Monticello’s most admired streets and offers timeless architecture with room to make it your own. The two-story layout includes 4 bedrooms and 3 bathrooms, with a circular driveway framed by boxwoods leading to a wide front porch perfect for rocking chairs. Inside, two front parlors flank the entry—one used as a living room and one with a closet allowing for modern use as a bedroom—and a traditional staircase leads upstairs to two bedrooms and a full bath. The large dining room has been opened to expose the original rafters, giving the space a bright and airy feel. Six original fireplaces provide historic character throughout the home. Period details including original hardwood floors, banisters, and molding showcase the craftsmanship of the era. Downstairs also includes a family room off the kitchen, a full guest bath, and a primary suite with an attached bath and nearby laundry. The upstairs landing opens to a secondary covered porch offering another peaceful spot to enjoy the quiet beauty of Pearl Street. The back portion of the property remains wooded, providing privacy or potential to expand with a guest house, pool, or garden. Just a short walk to downtown Monticello’s shops and restaurants, about 25 minutes to Thomasville, and roughly 30 minutes to Tallahassee. This home has over a century of stories, it's just waiting for its next tale to unfold!
Remodeled brick home, 3 br 1 bath, open kitchen living room with fireplace. Large utility room with bonus room. Convenient Monticello location. Carport and privacy fenced back yard.
Brimming with rustic charm, this 2 bedroom, 2 bathroom home sits on .29 acres just outside Monticello, FL giving you the peace of county living with lower taxes and the convenience of a quick drive into town. Inside, the 1,096sqft layout features inviting wood paneling throughout, with updates to the guest bathroom, a full electrical rewire and new water line and cozy spaces filled with character. Outside, you’ll find a large 1-car garage attached to the home, plus a carport/pole barn, and shed that offer plenty of room for hobbies, projects, or extra storage. With a prime location close to Monticello and only 20 minutes to Thomasville, this home is a unique blend of charm and practicality. Seller will replace the roof with an acceptable offer!
This gorgeous, 3-bedroom, 2-bath modular home, recently renovated by Paul Davis, combines modern comfort and style. Inside, you’ll find an open floor plan, a brand-new kitchen with granite countertops, new appliances, and updated finishes that make everyday living and entertaining a joy. The primary bedroom offers a luxurious ensuite with double vanities, a walk-in shower, and garden tub, as well as a spacious walk-in closet. Recent upgrades include a new hot water heater and HVAC (2022), and new ductwork (2025), new roof (2023), offering long-term peace of mind. Thoughtful details add to the appeal—like a convenient mudroom and outdoor dog wash, perfect for muddy boots, sandy feet, and four-legged friends, tail wags guaranteed!!! Outside, enjoy a spacious fenced backyard, along with covered front and back porches ideal for relaxing or hosting guests. A brand-new shop and carport provide extra storage and weather-protected parking, completing this move-in ready property. Located just 2.5 miles from the downtown, historic Monticello area, you will have easy access to all the charming shops and restaurants the town has to offer, as well as a quick commute to Thomasville or Tallahassee. Don't miss out on this stunning property that offers both modern upgrades and a convenient location!
New Construction move in ready. Sacious over 2300 sq fr. with upstairs bonus room with bath and closet, could be 4th bedroom. 5.38 acre lot. Top of the lines finishes. Convenient to Tallahassee 15 minute drive.
Certified Florida Green Home on 3 acres in the highly sough after Heritage Hills s/d. Enjoy the perfect blend of privacy and convenience with this Craftsman-style home, offering an easy commute to both Tallahassee and Monticello. The like-new residence boasts high-end finishes throughout, including crown molding, coffered ceilings, wainscoting, and a cozy gas fireplace. Relax or entertain year-round on the brick paver screened porch, and unwind in the luxurious fitness heated swim spa complete with LED lighting. A separate structure with 498 sf fully heated and cooled with half bath could be home office, studio, man cave,she shed, hobby room. . Native landscaping adds beauty and keeps maintenance easy. NEW ROOF 8/25 Solar Panels available for an additional price, includes 13 commercial -size panels. Backup system includes three, 2-kilowat lithium batteries to power essential needs during power outages.
Set on 10 private acres, this exceptional estate offers a lifestyle defined by space, serenity, and effortless luxury. Surrounded by nature and bordered by a tranquil private creek, the property feels like a personal retreat—yet remains perfectly designed for modern living and entertaining. Inside, 3,696 square feet of light-filled living space unfolds with soaring ceilings, expansive windows, and layout that invites both connection and relaxation. Natural views are ever-present, creating a seamless blend between indoor comfort and the beauty of the outdoors. At the heart of the home, the gourmet kitchen is designed for gathering and creativity, featuring a 6-burner gas range, custom cabinetry, and solid countertops. Whether preparing casual meals or hosting memorable dinners, the space flows effortlessly into the dining and living areas, anchored by a fireplace. The home offers four bedrooms and 4.5 baths, including three ensuite bedrooms that provide flexibility for multigenerational living or extended guests. The spacious primary suite on the main level offers a spa-inspired retreat with soaking tub and peaceful views that start and end each day in calm. A custom office with built-ins creates a work-from-home environment, while thoughtful details throughout enhance comfort and functionality. Outdoors, the acreage invites endless possibilities—morning walks by the creek, evenings under the stars, or simply enjoying the quiet luxury of space and privacy. This is more than a home—it’s a lifestyle of tranquility, connection, and refined living. Schedule a private showing and experience it for yourself.
2024 Custom Built Home with Premium Upgrades in Hemings Pond Subdivision! Better than new - This 3 bedroom/2 Bathroom 2024-build by Nailed It Construction offers luxury vinyl plank floors throughout, upgraded light fixtures, premium countertops, and elegant bath finishes. Both bathrooms feature tastefully muted designer tile-work. Thoughtful owner upgrades include: custom wood plantation shutters across the front of the home (road-side), remote control roller shades in all the bedrooms and dining area, a shadow-box style wood privacy fence enclosing the back yard, and a full irrigation system for effortless lawn care. Enjoy the convenience of city water and sewer although located just outside city limits. Move-in Ready!
Just WOW this beautiful new construction home, with top-of-the-line custom finishes. This home gives you all the luxury you are looking for - a primary suite with stunning tongue and groove wood tray ceilings, master bath with stand-alone soaking tub, walk-in shower, double vanity with quartz countertops, an oversized walk-in custom master closet with built-ins. As you approach the living area, you are greeted with a beautiful space designed for comfort and luxury - tongue and groove wood tray ceilings to complement the ones in the primary suite, gas brick fireplace. luxury vinyl plank flooring. The open concept allows for the living space and stunning kitchen to compliment each other perfectly. In the kitchen you will find custom cabinets, quartz countertops, tile backsplash, luxury LG appliance package with touchscreen stove/oven. The dining area is the perfect space to gather together, and right off the dining area a door leads you to your 1 acre backyard oasis with a large covered porch area. Back inside the home, you have an additional two bedrooms, with carpet, and a beautiful additional bathroom with a bathtub/shower combo with tile. The Sanctuary neighborhood has a 100 acre HOA owned property that can be used to walking, trail/golf cart riding, or hunting. This neighborhood and this home are at the top of their class! You don't want to miss out on this one! Measurements are not exact, up to buyer to confirm.
Custom home built by Kessler Construction on 2 full acres in desirable Crook Creek subdivision~4 bedrooms/3 full baths~gourmet kitchen~split bedroom plan~luxury master bath~incredibly high ceilings~42x14 screened porch~oversized 2-car garage~located on a cul-de-sac, this home offers peaceful privacy
THIS PROPERTY WILL NEED A TOTAL RENOVATION ON BOTH HOMES. Discover the perfect blend of rustic charm and opportunity with this unique country property. Nestled on 3+ acres, this older farm house offers character and room to grow. The main home features spacious living areas with wood floors throughout and plenty of potential for updates to make it your own. Front screen porch and large utility room. Also included is a second block home that will also need renovation. Additional outbuildings include a 13X26 workshop/storage building and 12x13 block building. Enjoy country living with room to breathe; come see the potential this special place has to offer. Seller motivated!
Classic historical home built in the 1920's. Walking distance to charming downtown Monticello. Large covered front porch for kicking back and relaxing. Wood floors throughout, high ceiling and large open kitchen. This beauty boast over 2700 sf of heated and cooled living space. Beautiful entry into foyer with stairway leading to upstairs landing and two bedrooms. Formal living, formal dining and sun room with office area. Exterior of home was just repainted with some interior painting. Slow down and enjoy North Florida peaceful living in beautiful Monticello Florida.
New beautiful LVP flooring on mother in law suite side of the property and wdo repair underneath the new flooring!! So many options with this property!! It boasts 2 separate living spaces joined by a common family room. One side of the home has 1 bed and 1 bath, it's own kitchen and living space. The other side of the home has 3 bedrooms, 2 bathrooms and the kitchen and living area. The family room with laundry is in the middle of the home. Each side has an enclosed porch too! So much space and an expansive yard too! Located in Monticello and convenient commute to Tallahassee in the neighborhood of Montivilla.
Spacious Contemporary Home on 5 Acres with Pond, Minutes from Thomasville, Ga! Enjoy peaceful country living with modern comforts in this stunning 3 bedroom, 3 bathroom brick home on 5 beautiful acres with a private pond. With over 3,000 square feet of living space, this property offers room to spread out and features thoughtful touches throughout. Inside, you'll find a large den with cozy fireplace, a bright and airy sun-porch for relaxing or entertaining, and a well-designed floor plan that balances open living with privacy. The spacious kitchen opens into the den, and the separate formal and dining living areas are ideal for family gatherings. Also includes a bonus room ideal for office space. The primary suite includes a sitting area and en-suite bath, and all bedrooms are generously sized. A 2-car garage provides ample storage. Easy commute to both Thomasville, Ga or Tallahassee, Fl. A flooring allowance is being offered by the seller, so you can choose your own finishing touches. This property combines the serenity of nature with accessibility to town amenities.
Gorgeous brand new construction on half acre or more! One story split floorplan with large master suite. Granite countertops with custom cabinetry. Ample living space and open concept with 10' trey ceilings. 3 bedrooms and 2 full baths and huge master shower. Fiber cement siding and architectural shingles. 185 total square feet of outside sitting space. Large 2 car garage. We have some homes in progress and some that have not even been started. No matter your timeframe, we can accommodate. Photos are of previous built home. Estimated completion date is 03/31/2023.
Gorgeous brand new construction on half acre or more! One story split floorplan with large master suite. Granite countertops with custom cabinetry. Ample living space and open concept with 10' trey ceilings. 3 bedrooms and 2 full baths and huge master shower. Fiber cement siding and architectural shingles. 185 total square feet of outside sitting space. Large 2 car garage. We have some homes in progress and some that have not even been started. No matter your timeframe, we can accommodate. Photos are of previous built home. Estimated completion date is 03/31/2023.
Gorgeous brand new construction on half acre or more! One story split floorplan with large master suite. Granite countertops with custom cabinetry. Ample living space and open concept with 10' trey ceilings. 3 bedrooms and 2 full baths and huge master shower. Fiber cement siding and architectural shingles. 185 total square feet of outside sitting space. Large 2 car garage. We have some homes in progress and some that have not even been started. No matter your timeframe, we can accommodate. Photos are of previous built home. Estimated completion date is 03/31/2023.
Gorgeous brand new construction on half acre or more! One story split floorplan with large master suite. Granite countertops with custom cabinetry. Ample living space and open concept with 10' trey ceilings. 3 bedrooms and 2 full baths and huge master shower. Fiber cement siding and architectural shingles. 185 total square feet of outside sitting space. Large 2 car garage. We have some homes in progress and some that have not even been started. No matter your timeframe, we can accommodate. Photos are of previous built home. Estimated completion date is 03/31/2023.
Gorgeous brand new construction on half acre or more! One story split floorplan with large master suite. Granite countertops with custom cabinetry. Ample living space and open concept with 10' trey ceilings. 3 bedrooms and 2 full baths and huge master shower. Fiber cement siding and architectural shingles. 185 total square feet of outside sitting space. Large 2 car garage. We have some homes in progress and some that have not even been started. No matter your timeframe, we can accommodate. Photos are of previous built home. Estimated completion date is 03/31/2023.
The data relating to real estate for sale on this website comes in part from the Internet Data Exchange Program of Tallahassee Board of Realtors. The information is provided exclusively for consumers’ personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate.
Monticello is located in Florida. Monticello, Florida 32344has a population of 2,539. Monticello 32344 is less family-centric than the surrounding county with 18.27% of the households containing married families with children. The county average for households married with children is 20.81%.
The median household income in Monticello, Florida 32344 is $43,780. The median household income for the surrounding county is $53,080 compared to the national median of $69,021. The median age of people living in Monticello 32344 is 53.5 years.
The average high temperature in July is 91.4 degrees, with an average low temperature in January of 38.5 degrees. The average rainfall is approximately 53.9 inches per year, with 0.1 inches of snow per year.
