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$1,500,000
402579 MLS
Amazing location for this 8 pump gas station/convenience store on corner of US Hwy 27 and Waukeenah Hwy with a high traffic count. The station sits on 1.74 acres and has 4,880 sf heat/cooled concrete block building. When fully operational, the site averages 80,000 gallons of gas per month plus it will have a national branded AMCO TO GO C-Store to increase store sales if the buyer chooses to use the property as a gas station. The property is being sold "AS IS" with the right to inspections. If you have ever dreamed of owning your own business, this is a great opportunity as the pumps and tanks were upgraded in 2022.

9495 Waukeenah Highway, Monticello
$1,325,000
5 Beds ⋅ 5 Baths ⋅ 395876 MLS
Welcome to a rare North Florida estate just minutes from Tallahassee—where luxury, land, and lifestyle come together. 221 Kiley Road is situated on expansive acreage in Monticello, and this private retreat offers the perfect blend of seclusion and convenience, located just a short drive from the heart of Tallahassee. For buyers seeking space, privacy, and versatility without sacrificing proximity to town, this property delivers. This 5-bedroom, 3.5-bathroom estate is a true masterpiece, gracefully set on 5 private acres and complemented by a beautiful pool house with an additional bathroom. An additional adjoining 5-acre parcel is also available, offering the rare opportunity to expand your privacy, create a multi-generational compound, or enhance the estate even further. Set on picturesque rolling land, this one-of-a-kind property features your own private vineyard, offering a breathtaking and romantic backdrop for everyday living and entertaining. Imagine sunset dinners overlooking the vines, peaceful morning walks through the rows, or simply enjoying the beauty and serenity that only a setting like this can provide. Equestrian enthusiasts will appreciate the well-appointed horse stable, open pasture, and room to ride, creating the perfect environment for both horses and riders to thrive. Thoughtfully designed for function and beauty, the grounds invite you to embrace true North Florida country living. At the heart of the property sits an impressive residence offering approximately 5,500 square feet of living space, ideal for large households, multi-generational living, or those who love to entertain. The thoughtfully designed layout features expansive living areas filled with natural light, a spacious kitchen with abundant cabinetry and workspace, and oversized bedrooms that serve as peaceful private retreats. Multiple flex spaces provide endless possibilities for home offices, media rooms, fitness areas, hobby spaces, or additional guest accommodations — tailored to fit your lifestyle. Step outside to your private pool oasis, perfect for relaxing afternoons or hosting unforgettable gatherings. A separate guest house offers comfortable accommodations for visitors, extended family, or a private retreat, adding flexibility and value to this exceptional estate. From vineyard evenings and horseback mornings to poolside afternoons, this Tallahassee luxury home alternative is more than a home — it’s a lifestyle. Offering space, versatility, natural beauty, and privacy while still convenient to downtown Monticello, schools, shopping, and dining, this is a truly rare opportunity to own a remarkable property where memories are made for generations.

221 KILEY Drive, Monticello
$1,200,000
4 Beds ⋅ 3 Baths ⋅ 402221 MLS
**Some Photos are Virtually Enhanced** Experience luxury living in the prestigious gated community of Rainey Run. This is where privacy, nature, and convenience come together on 10 breathtaking acres. Surrounded by towering hardwoods and abundant wildlife, this remarkable property offers a convenient peaceful retreat. Built in 2020, this custom home showcases quality craftsmanship with a highly thought out design. Greeted by a beautifully crafted foyer, you immediately feel at home from the moment you walk through the door. The spacious kitchen opens to the living room offering the perfect entertainment design. The spacious floor plan is designed for both comfortable everyday living and effortless entertaining. Allowing privacy with its split floor plan, the primary bedroom features his and her walking closets with a spa like bathroom escape. 3 bedroom with office (or 4th bedroom) and bonus room (could be used as another bedroom). Step outside and enjoy your own private sanctuary, where deer, turkey, and other native wildlife are frequent visitors. A large workshop with electricity and water provides endless opportunities for hobbies or equipment storage. Located behind the gates of one of Jefferson County’s most desirable communities, Rainey Run offers the peaceful escape from the city with the convenience of Tallahassee being only a few minutes away. Schedule your private showing today, this home has so much more to share! Built by Saxon Hannon, of Hannon Construction. Buyers to verify all dimensions and measurements.

974 Rainey Run, 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
$775,000
4 Beds ⋅ 3 Baths ⋅ 396927 MLS
New Construction. Images are renderings. 4-bedroom, 3-bath home coming soon in Tally Hills Estates. Construction has started on this beautifully designed, new construction home set on over 5 acres.

693 Tally Hills Drive, Monticello
$599,000
7 Beds ⋅ 7 Baths ⋅ 398052 MLS
Introducing a stunning 1.2 acre estate in the heart of Historic Downtown Monticello. The Simon-Ridgeway home was built in 1888 and boasts a generous 4,500 sq ft of living space and features 7 spacious bedrooms, 5 of which come with its own en-suite bathroom for ultimate privacy and convenience. City granted BNB status - making this perfect for an owner/occupier wanting to work from home and enjoy small town life! You'll fall in love with the intricately designed hardwood floors that flow throughout the home, perfectly complementing the timeless charm. The newly remodeled kitchen is a chef's dream, blending modern amenities with classic elegance, from the large farmhouse sink to the new Stainless Steel appliances. Too many updates to list- but some include a new roof, AC's, bathrooms, and kitchen, just to name a few! Enjoy the slower pace of life from the huge, Double-Story Gothic Revival front porches or the large back deck. Other outdoor features include: Large Detached Double garage with washer dryer hookups; and 2 small houses in the backyard for multigenerational living, Airbnb income or extra space for guests! Don't miss your chance to own a piece of history that offers both luxury and comfort. Schedule a showing today! Creative Financing available.

625 E WASHINGTON Street, 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
$439,900
3 Beds ⋅ 2 Baths ⋅ 399057 MLS
Welcome to this exquisite soon to be finished new construction home in the quiet and quaint Crooked Creek Subdivision, conveniently located just off of 90E and only minutes away from the historic charm of Downtown Monticello. With easy access for commuting to Tallahassee or Thomasville, this location offers the perfect balance of peaceful living and convenient amenities. Immerse yourself in the local community, with nearby parks, charming shops, and a wealth of recreational opportunities right at your fingertips. Whether you're exploring the picturesque surroundings or enjoying the vintage shopping experiences, this location truly has it all. Step inside this stunning home and be captivated by the thoughtful builder specs and attention to detail. Spanning 1883 square feet, this spacious home features 3 bedrooms, with a versatile 4th room that can be used as an office or bonus room, accommodating all your lifestyle needs. The 2 full baths provide convenience and comfort, while the tray ceiling in the living room adds an elegant touch to the space. Luxury vinyl plank flooring throughout the home ensures durability and easy maintenance, while the solid wood cabinets and quartz countertops in the kitchen create a stylish and functional culinary haven. Admire the unique barn door leading to the 4th room, adding a touch of charm and versatility to the floor plan. The separate laundry and mudroom offer convenience and organization, while the electric fireplace adds warmth and ambiance to the living area. With a 2-car garage, you'll have plenty of space for parking and storage. The split floor plan and open concept layout make this home ideal for both entertaining and everyday living, providing a seamless flow between rooms and ample privacy for all. Don't miss the opportunity to make this new construction home yours, where comfort, style, and convenience blend seamlessly. Experience the beauty and craftsmanship of this remarkable property in the desirable Crooked Creek Subdivision. Expected completion date July 2026. Buyer to verify all measurements.

110 Crooked Creek Lane, 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
$395,000
4 Beds ⋅ 3 Baths ⋅ 391898 MLS
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 an opportunity to restore and 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—while upstairs includes two additional 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, while six original (not currently operational) fireplaces provide historic character throughout. 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 home features a two-zone HVAC system downstairs, with window units currently serving the upstairs bedrooms. The roof is estimated to have approximately 5–7 years of remaining life. This property offers an opportunity for thoughtful updates and stewardship, presenting a great fit for buyers looking to invest in a historic home with strong bones and character. The back portion of the property remains wooded, providing privacy or potential to expand with a guest house, pool, or garden. Conveniently located just a short walk to downtown Monticello’s shops and restaurants, about 25 minutes to Thomasville, and roughly 30 minutes to Tallahassee. Offered As-Is, this home has over a century of stories—it’s ready for its next chapter. Seller is motivated and will consider all offers.

930 E Pearl 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
$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
$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
$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
$279,000
403115 MLS
A piece of history in historic downtown Monticello. Tremendous charm for an office, retail store or combination home office.. Walk to downtown shops and restaurants. Spacious front porch overlooks picturesque downtown.

380 N jefferson Street, 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
$265,000
396434 MLS
OWN A PIECE OF HISTORIC DOWNTOWN MONTICELLO! Opportunity awaits in the heart of Historic Downtown Monticello! This versatile commercial space is currently operating as a retail shop and offers exceptional flexibility for a variety of business uses. Large front-facing windows provide abundant natural light and excellent visibility, overlooking the vibrant sidewalk area- perfect for attracting foot traffic and showcasing your business. Inside you will find spacious retail floor area, full kitchen, one bath with additional plumbing already in place for additional bath. Ample storage space leading to your own back entrance. Whether you envision a boutique, cafe, studio or specialty shop, this property offers the infrastructure and location to bring your concept to life.

185 E Dogwood Street, 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
$150,000
403463 MLS
Beautiful country property on nearly 10 acres to build your dream home on.

Watermill Road, Monticello
$135,750
404212 MLS
Discover the perfect opportunity to own a pristine 9-acre tract of raw land just on the outskirts of charming Monticello. This largely untouched property offers a peaceful country setting with rolling farmland and classic North Florida character, making it an ideal location for your future home or recreational retreat. Situated with road frontage on Ashville Highway, this buildable tract is covered in mature pine trees and teeming with abundant wildlife, creating a natural haven for outdoor enthusiasts. Whether you're dreaming of a family homestead, a working farm, or a legacy property to enjoy for generations, this land provides endless possibilities. Conveniently located just minutes from historic downtown Monticello, you'll have quick and easy access to local amenities, while also enjoying the serenity of a quiet country setting. Plus, with quick routes to Interstate 10, travel to Tallahassee, Thomasville, and beyond is effortless. Embrace the natural beauty, tranquility, and potential of this exceptional property—an ideal place for recreation, agriculture, or a peaceful family home. Don’t miss your chance to own a piece of North Florida’s timeless landscape.

XXX Ashville HWY, Monticello
$65,000
404328 MLS
Discover a rare opportunity to own 1.75 acres on Walker Springs Road, directly adjoining approximately 40,000-acres of the Aucilla Wildlife Management Area. Very few private parcels border this protected land, and this is currently the only adjoining property being offered on the market! Deer, turkey, and other wildlife are abundant and can often be seen right outside your back door. With the main entrance to the wildlife management area less than a quarter-mile away, this property is ideally situated for hunters, outdoor enthusiasts, or anyone seeking a peaceful escape surrounded by nature. The property features magnificent grandfather oaks draped in Spanish moss, creating the timeless atmosphere of old Florida. A 12x20-foot shed is already on the property and could potentially be used as a simple hunting camp, weekend retreat, or storage building. Conveniently located just minutes from the pristine Wacissa River, approximately 25 miles from Tallahassee and 20 miles from Monticello—this exceptional property offers privacy and natural beauty without being too far from town.

1602 Walker Springs Rd., Monticello
$39,900
403424 MLS
Discover the perfect spot to build your dream home or weekend getaway on this 1.91-acre property in Monticello! Featuring paved road frontage, a partially cleared homesite, and plenty of room to enjoy the surrounding natural beauty, this property offers the ideal balance of privacy and convenience. Located with easy access to both Monticello, FL and Thomasville, GA, you’ll enjoy peaceful country living while remaining close to shopping, dining, and everyday amenities. Don’t miss this great opportunity to own your piece of North Florida! No Mobile Homes Allowed. Additional 1.91 acres also available.

Vacant BARNES Road, Monticello
$39,900
403422 MLS
Discover the perfect spot to build your dream home or weekend getaway on this 1.91-acre property in Monticello! Featuring paved road frontage, a partially cleared homesite, and plenty of room to enjoy the surrounding natural beauty, this property offers the ideal balance of privacy and convenience. Located with easy access to both Monticello, FL and Thomasville, GA, you’ll enjoy peaceful country living while remaining close to shopping, dining, and everyday amenities. Don’t miss this great opportunity to own your piece of North Florida! No Mobile Homes Allowed. Additional 1.91 acres also available.

76 BARNES Road, Monticello