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Jefferson County FL Houses for Sale

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  • /42

    $339,000

    • 4 Beds
    • 4 Baths
    • 3,456 Sq Ft

    852 E Buckhorn Trail, Greenville, FL 32331

    Woodland Retreat and Unique Escape on 5 acres! Not your ordinary cookie cutter! Discover this private hilltop sanctuary tucked down a rustic, winding, woodsy lane, with 4 "lodge" inspired bedrooms, each with their own bathroom/closet combinations. On the approach in, take it slow, unwind from the city life and pass by "Mom and Pop" farms, fields, rusty barns, Grandpa's forgotten vehicles, chicken

    Agent Photo

    Lynette Sirmon

    All Realty Services

    (850) 930-1972

    852 E Buckhorn Trail, Greenville, FL 32331
  • /42

    $469,000

    • 5 Beds
    • 2 Baths
    • 2,184 Sq Ft

    10283 Ashville Hwy, Greenville, FL 32331

    Amazing opportunity to own this private solar-powered farm with a large house! Beautiful and serene 16 acres with fruit trees, fields, lots of horse potential and 40 solar panels less than 5 years old. Nearly free electric! 5 Bedroom, 2 Bath with Large Eat-in Kitchen, Stainless Steel Appliances, Huge Great Room, Beautiful Hardwood Floors throughout main floor of the house, TWO Large Screened-in

    Lee Hall Capital City Real Estate Group

    10283 Ashville Hwy, Greenville, FL 32331
  • /38

    $419,000

    • 3 Beds
    • 3 Baths
    • 2,706 Sq Ft

    339 Silver Lake Rd, Monticello, FL 32344

    Gorgeous home on 5 acres mostly pasture. Open concept with vaulted ceilings; great entertainment/family home. Private setting; must see to believe.

    Steve Walker Steve C. Walker Realty, LLC

    339 Silver Lake Rd, Monticello, FL 32344
  • /42

    $1,125,000

    • 3 Beds
    • 1 Bath
    • 1,146 Sq Ft

    740 Kinsey Rd, Monticello, FL 32344

    Location: Jefferson County, FL Size: 155 acres Features: Rolling pastures Planted pines Natural hardwoods Pond Home: 1941 built 1,146 square feet Updated Outbuildings: With power Opportunities for workshops, storage, and more Additional Homesites: Breathtaking views Peaceful living Proximity: 10 miles from downtown Monticello, FL 5 miles to I-10 Wildlife: Deer Turkey Waterfowl

    Ben Jones Southern Land & Homes

    740 Kinsey Rd, Monticello, FL 32344
  • /67

    $380,000

    • 3 Beds
    • 2 Baths
    • 1,722 Sq Ft

    525 Devane Rd, Monticello, FL 32344

    2024 custom-built, single story home on 3 acres near Jefferson Country Club with no HOA. Features 3 bedrooms plus a flexible bonus room—perfect for an office, studio, or guest space. Open floor plan with great room, bar seating, stainless appliances, high-end countertops, and LVP flooring throughout. Primary bath offers both a soaking tub and low-entry shower for accessibility. Storage

    Victoria Wilde Xcellence Realty

    525 Devane Rd, Monticello, FL 32344
  • /42

    $449,000

    • 3 Beds
    • 2 Baths
    • 1,921 Sq Ft

    2497 Boston Hwy, Monticello, FL 32344

    Charming Hillside Country Retreat with Barn and Acreage. Welcome to your dream countryside escape! This beautifully maintained brick home sits peacefully on a hillside, surrounded by sprawling fields dotted with mature pecan trees. Inside, the home features a spacious open floor plan, perfect for entertaining or relaxing with family. The large kitchen offers ample workspace and storage, while the

    Pam Kelly Kelly & Kelly Properties, Inc

    2497 Boston Hwy, Monticello, FL 32344
  • /39

    $624,900

    • 3 Beds
    • 2.5 Baths
    • 2,546 Sq Ft

    181 Heritage Blvd, Monticello, FL 32344

    Highly Desirable Heritage Hills Location! Enjoy the perfect blend of privacy and convenience with this Craftsman-style home located on 3 serene acres, 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

    Pam Kelly Kelly & Kelly Properties, Inc

    181 Heritage Blvd, Monticello, FL 32344
  • /34

    $499,000

    • 8 Beds
    • 4 Baths
    • 4,806 Sq Ft

    2664 W Washington Hwy, Monticello, FL 32344

    FULLY RENOVATED TWO HOUSES, 1.9 acres, on picturesque US 90 near Monticello. UNDER $99/SF! These move-in-ready homes in good condition have a total of 8 bedrooms, 4 baths, and 4,806 s.f. living area. The MAIN HOUSE is a 1950’s era brick ranch-style home with new plumbing, new electric, fresh paint, new roof, whole home generator. Great opportunity for multiple generations to live side by side, or

    Heather Boyd FL-GA Realty & Auction

    2664 W Washington Hwy, Monticello, FL 32344
  • /39

    $529,000

    • 3 Beds
    • 2.5 Baths
    • 1,915 Sq Ft

    160 Lineage Ct, Monticello, FL 32344

    Beautiful 3-bedroom, 2.5-bath farmhouse offers privacy, charm, and modern conveniences. Built in 2016 and tucked away at the end of a cul-de-sac on 2.78 acres in desirable Heritage Hills. Home features an iron gate and long driveway—plenty of extra room for your boat or RV—along with a metal roof, a classic rocking chair front porch, large covered patio for entertaining and a 2-car garage.

    Leanne Groom The Naumann Group Real Estate

    160 Lineage Ct, Monticello, FL 32344
  • /69

    $695,000

    • 3 Beds
    • 2 Baths
    • 2,083 Sq Ft

    5301 Gentle Breeze Dr, Tallahassee, FL 32309

    NEW PRICE!!! RARE OPPORTUNITY to own lakefront property on the picturesque Lake Miccosukee! Charming cabin is discreetly nestled by the water’s edge, embracing a naturally beautiful 10-acre estate. Property features an inviting home with an expansive family room, complete with a stunning window wall, providing breathtaking views surrounded by nature with abundant local wildlife for hunting or

    Nancy Treadway Treadway Appraisal & Realty

    5301 Gentle Breeze Dr, Tallahassee, FL 32309
  • /63

    $519,000

    • 3 Beds
    • 2 Baths
    • 2,170 Sq Ft

    282 Long Leaf Dr, Monticello, FL 32344

    Enjoy space, privacy, and outdoor living on this well-maintained 5-acre property in Monticello. Tucked away on a private dirt road, this 3-bedroom, 2-bathroom home offers a functional 2,170 square foot layout with plenty of natural light. Outside is where this property really shines—featuring a screened-in patio, a sparkling pool with a Baja shelf, and multiple outdoor entertaining areas

    Catherine Hope All Realty Services

    282 Long Leaf Dr, Monticello, FL 32344
  • /40

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,985 Sq Ft

    480 W Washington St, Monticello, FL 32344

    OWNERS MOTIVATED-ALL REASONABLE OFFERS WILL BE CONSIDERED.Step Back In Time! Rare chance to own your own piece of "Old Florida". Craftsman Style beauty with soaring 10 ' bead-board ceilings and 10 " baseboards, original pine floors and 4 gas fireplaces. Perfect blend of old Florida charm and modern conveniences. Statuary Marble countertops and copper sink in kitchen, extra large dining room for

    Pam Kelly Kelly & Kelly Properties, Inc

    480 W Washington St, Monticello, FL 32344
  • /19

    $430,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,865 Sq Ft

    173 Deerfield Ln, Monticello, FL 32344

    NEW CONSTRUCTION COMPLETE! Walk into this stunningly crafted three-bedroom, two-bathroom home that is perfectly rooted on a corner lot just a few miles from town. Situated on a full acre of land, this charming property is a rare find, free from HOA restrictions—giving you the freedom to personalize your space as you wish. Inside, you'll discover an open and welcoming floor plan that includes

    Caleb Stephens Silo Hill Properties

    173 Deerfield Ln, Monticello, FL 32344
  • /41

    $455,995 New Construction

    • 3 Beds
    • 2 Baths
    • 1,806 Sq Ft

    47 Mire Ct, Monticello, FL 32344

    Amazing new construction 3 bedroom 2 bathroom by Nailed It Tallahassee LLC Come pick out all your finishes, home scheduled for completion August 2025. Luxurious master suite, Kitchen made of dreams, this is a must see! Preferred Lender offering 1% in closing costs! Photos of previous home come make this one your own!

    Amber McKinney Hamilton Realty Advisors LLC

    47 Mire Ct, Monticello, FL 32344
  • /64

    $1,200,000

    • 8 Beds
    • 6.5 Baths
    • 5,560 Sq Ft

    237 Valley View Ct, Monticello, FL 32344

    Unbelievable opportunity in Valley View Estates! Situated on 15+ (10+5) high-and-dry acres along the Leon/Jefferson County line, this unique property features two full-sized homes, a barn with additional living space, a heated/cooled workshop, and a screened pool with lanai. The custom-built main residence (~4000sf) offers 12’ ceilings, 3 bedrooms with ensuite baths, 2 additional bedrooms/flex

    Kelly Vinson Keller Williams Town & Country

    237 Valley View Ct, Monticello, FL 32344
  • /21

    $285,000

    • 3 Beds
    • 2 Baths
    • 1,740 Sq Ft

    104 Pine Cone Dr, Monticello, FL 32344

    Professional Photos coming soon. This gorgeous, recently renovated 3-bedroom, 2-bath modular home 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

    Trevor Ann Clark Keller Williams Town & Country

    104 Pine Cone Dr, Monticello, FL 32344
  • /35

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,370 Sq Ft

    1530 Sweetbay Ct, Monticello, FL 32344

    Like New! Barely lived in Home in the sought-after Crooked Creek Subdivision! Easy commute to Thomasville and Tallahassee with the small-town charm of Monticello! This beautiful 3/2 is on a spacious cul-de-sac lot and the house is upgraded to include but not limited to stainless steel appliances, recessed lighting, vaulted ceilings, with granite and quartz countertops, and a stunning kitchen

    Chance Shutes Keller Williams Town & Country

    1530 Sweetbay Ct, Monticello, FL 32344
  • /41

    $329,500

    • 4 Beds
    • 2 Baths
    • 2,162 Sq Ft

    4081 Gamble Rd, Monticello, FL 32344

    Nestled on a serene 5-acre retreat, this charming storybook cottage feels like a hidden gem, yet it’s just 15 minutes from downtown Monticello’s quaint shops and restaurants. Tucked back from the road for ultimate privacy, this well-maintained home is surrounded by natural beauty, including native plants, wild azaleas, and lush greenery. Step onto the inviting front porch and into a warm,

    Malissa Henning EXP Realty, LLC

    4081 Gamble Rd, Monticello, FL 32344
  • /4

    $209,900

    • 3 Beds
    • 2 Baths
    • 1,678 Sq Ft

    85 Pine Cone Dr, Monticello, FL 32344

    This beautifully renovated 3-bedroom, 2-bathroom modular home offers modern comfort and style. Inside, you'll find granite countertops, all new appliances, and updated finishes with a thoughtful layout perfect for both daily living and entertaining. A brand-new roof was installed in July 2025, and the HVAC system was replaced in October 2021, ensuring long-term peace of mind. Enjoy the outdoors

    Gabriela Sacco All Realty Services

    85 Pine Cone Dr, Monticello, FL 32344
  • /28

    $239,000

    • 3 Beds
    • 2 Baths
    • 1,234 Sq Ft

    44 Pine Needle Trace, Monticello, FL 32344

    Charming Home with Open Floor Plan in Beautiful Monticello, FL! Welcome to this cozy well maintained home featuring an inviting open floor plan, warm wood-burning fireplace and vaulted ceilings that add space and character. French doors off the main living area open to a spacious deck overlooking the backyard. Freshly pained throughout the interior. Seller offering a flooring allowance with

    Pam Kelly Kelly & Kelly Properties, Inc

    44 Pine Needle Trace, Monticello, FL 32344
  • /46

    $178,000

    • 3 Beds
    • 3 Baths
    • 2,635 Sq Ft

    18 Perkins Williams Rd, Monticello, FL 32344

    Opportunity to finish a traditional-style home on 2.02 acres in the Monticello countryside. Built in 2001 by a local contractor, the home is approximately 80% complete and has never been lived in. The structure needs a new roof, HVAC system, water heater, bedroom flooring, and completion of the master bath. There is visible foundation settlement—cause and extent unknown. Located in a flood

    Ashley Hartsfield Keller Williams Town & Country

    18 Perkins Williams Rd, Monticello, FL 32344
  • /70

    $1,050,000

    • 4 Beds
    • 4.5 Baths
    • 3,696 Sq Ft

    825 Rainey Run, Monticello, FL 32344

    Welcome to this rare Monticello, FL luxury home for sale on 10 pristine acres with private creek frontage. This 4-bedroom, 4.5-bathroom estate spans nearly 3,700 square feet of elegant living space, offering the perfect blend of privacy, acreage, and modern luxury just minutes from Tallahassee. Property Highlights: 10 acres with a private creek 4 bedrooms, 3 with ensuite bathrooms 3,696 sq. ft.

    Renee Dawkins Ketcham Realty Group, Inc.

    825 Rainey Run, Monticello, FL 32344
  • /70

    $989,000

    • 4 Beds
    • 3 Baths
    • 4,600 Sq Ft

    2024 Old Lloyd Rd, Monticello, FL 32344

    Square footage includes both the main house is 3200 square feet with 4 bedrooms and 3 baths. New barn apartment is 1400 square feet with 2 bedrooms and 1 bath. This would be an amazing income producing property for short and/or long term rental property of barn apt, horse boarding stables ... or even a wedding venue. This breathtaking property checks ALL of the boxes! Please see associated

    Katherine Hansli Searcy The Naumann Group Real Estate

    2024 Old Lloyd Rd, Monticello, FL 32344
  • /43

    $295,000

    • 3 Beds
    • 2 Baths
    • 2,044 Sq Ft

    300 Cedar St, Monticello, FL 32344

    Welcome to 300 Cedar Street ~ Located a stone's throw from Monticello's charming downtown, yet quiet & private ~ Relax in a rocking chair & enjoy sitting on your HUGE 64x8 screened in porch that runs the entire length of the back of the home & overlooks the serene 1.5 acre lot ~ Built in 1958, this single story home is a sturdy brick ranch style with 3 Bedrooms, 2 Baths, extra large attached 2

    Jonathan Rigsby Spotlight Real Estate

    300 Cedar St, Monticello, FL 32344
  • /45

    $275,000

    • 4 Beds
    • 2 Baths
    • 1,812 Sq Ft

    685 E Washington St, Monticello, FL 32344

    Perfect brick family home right downtown! Walk to the veggie stand across the street and all the Monticello shops! Renovated 4-bed, 2-bath home. New roof!! New Custom Kitchen cabinets, granite counters, and SS Appliance package perfect for all those home chefs. The open-plan kitchen opens directly into the dining and living room. New Flooring, Paint, Light fixtures, Custom closets and bookcases

    Lee Hall Capital City Real Estate Group

    685 E Washington St, Monticello, FL 32344
  • /33

    $215,900

    • 2 Beds
    • 2 Baths
    • 1,356 Sq Ft

    1065 S Mulberry St, Monticello, FL 32344

    This cozy home located in the heart of Monticello is the perfect 2/2 for a starter family looking to settle down or someone looking for a small, southern home in a quiet town! There is so much potential with good bones from the old hardwood floors to the floor-to-ceiling windows. This home is in walking distance to the roundabout near restaurants and antique shops or to the grocery store. With a

    Katherine Gonzalez Pearson Realty Inc.

    1065 S Mulberry St, Monticello, FL 32344
  • /34

    $269,000

    • 3 Beds
    • 2 Baths
    • 1,654 Sq Ft

    130 Simpson Ave, Monticello, FL 32344

    Beautiful home located in historic Monticello within walking distance to downtown shopping, restaurants, and farmers market. Featuring 3 spacious bedrooms with 2 large bathrooms and a walk-in closet. This charming cottage has an extra office/study area, original fireplace, glass french doors to dining room and updates throughout while staying true to its original character. Step outside to a

    Suzanna Malone Lauer Real Estate Group LLC

    130 Simpson Ave, Monticello, FL 32344
  • /14

    $175,000

    • 3 Beds
    • 2 Baths
    • 1,716 Sq Ft

    375 Maple St, Monticello, FL 32344

    Affordable home nestled in the heart of Monticello! This spacious home sports a freshly painted open floor plan. Wood finished line this home sharing a feeling of craftsmanship. Updated appliances make this home walk in ready for its next family. Nestled on a corner lot, this home has great curb appeal.

    Caleb Stephens Silo Hill Properties

    375 Maple St, Monticello, FL 32344
  • /29

    $285,000

    • 2 Beds
    • 2 Baths
    • 1,404 Sq Ft

    9497 Gamble Rd, Monticello, FL 32344

    Nestled on 6 beautiful wooded acres, this charming 2 bedroom, 2 bath cypress house offers the perfect blend of rustic charm and modern convenience. The house has a whole home generator, providing peace of mind during any power outages. Inside, you will find stunning cork floors throughout. Additionally, the property boasts 2 sheds with electricity, perfect for storage or workshop space. This

    Trevor Ann Clark Keller Williams Town & Country

    9497 Gamble Rd, Monticello, FL 32344
  • /61

    $589,900

    • 4 Beds
    • 3 Baths
    • 2,660 Sq Ft

    513 Creekside Ct, Monticello, FL 32344

    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

    Renee Smawley Steve C. Walker Realty, LLC

    513 Creekside Ct, Monticello, FL 32344
  • /27

    $225,000

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    140 E Buckhorn Trail, Greenville, FL 32331

    Welcome to this peaceful countryside retreat, located on a spacious, private lot in Greenville, FL. This charming 3-bedroom, 2-bath home combines warmth, functionality, and ample space both inside and out. As you enter, you'll find a bright and inviting living area with a wall of windows that allows natural light to pour in and provides serene views of the surrounding woods. The sunroom is a

    Christopher Worth Keller Williams Town & Country

    140 E Buckhorn Trail, Greenville, FL 32331
  • /5

    $65,000

    • 4 Beds
    • 1 Bath
    • 1,232 Sq Ft

    4618 E Capps Hwy, Lamont, FL 32336

    Fixer upper on 1 acre of land. Needs lots of work. Well and septic tank on property. Would need to check to make sure they are good working order.

    Nelda Parker-Pace Sawgrass Realty, LLC

    4618 E Capps Hwy, Lamont, FL 32336
  • /43

    $1,549,000

    • 5 Beds
    • 4.5 Baths
    • 5,476 Sq Ft

    221 Kiley Dr, Monticello, FL 32344

    Welcome to a rare and exquisite, turn-key, 15-acre modern luxury estate, where timeless elegance meets Southern charm. Custom built by Riley Palmer, this exclusive, gated property with soaring ceilings and interior doors, is nestled just minutes from Tallahassee, Florida's Capital City, and historic Thomasville, Georgia in Monticello-home to a storied opera house and chic dining options-and

    Barbra Engel & Völkers Tallahassee

    221 Kiley Dr, Monticello, FL 32344
  • /42

    $649,900

    • 3 Beds
    • 2.5 Baths
    • 3,214 Sq Ft

    150 N Ojibwa Rd, Monticello, FL 32344

    Tranquil 5.1 acre retreat nestled deep in a pecan grove just outside Monticello, Florida has it all. This recently remodeled 3BR/2BA home offers space, privacy and flexibility in a rural setting only 40 minutes from the heart of Tallahassee. Take advantage of everything Tallahassee offers while paying lower Jefferson County taxes. The pecan trees qualify for an agricultural land use status,

    Hettie Spooner Hill Spooner & Elliott Inc

    150 N Ojibwa Rd, Monticello, FL 32344
  • /42

    $219,000

    • 3 Beds
    • 2 Baths
    • 2,390 Sq Ft

    2436 N Jefferson Hwy, Monticello, FL 32344

    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 need

    Pam Kelly Kelly & Kelly Properties, Inc

    2436 N Jefferson Hwy, Monticello, FL 32344
  • /19

    $289,000

    • 4 Beds
    • 2 Baths
    • 1,858 Sq Ft

    575 E Palmer Mill Rd, Monticello, FL 32344

    Spacious home located within walking distance of Historic Downtown Monticello. This four bedroom home sits quietly on a manageable half acre lot. Sporting both original hardwood flooring and newly installed LVP flooring, this home blends perfectly for any new home owners. Updated bathrooms and appliances have all been done within the last 5 years. Sizes are approximate.

    Caleb Stephens Silo Hill Properties

    575 E Palmer Mill Rd, Monticello, FL 32344
  • /40

    $1,285,000

    • 4 Beds
    • 6 Baths
    • 9,848 Sq Ft

    193 Nautilus Dr, Monticello, FL 32344

    Introducing a breathtaking fusion of modern convenience and medieval charm nestled in the heart of the woods. This meticulously renovated 9,848 square foot architectural marvel boasts a captivating design, featuring uniquely sized windows and curving walls that exude artistic allure at every turn. Step inside and experience the epitome of luxury living. The main building offers a seamless blend

    Ondrea Maldonado Hamilton Realty Advisors LLC

    193 Nautilus Dr, Monticello, FL 32344
  • /42

    $599,900

    • 4 Beds
    • 5 Baths
    • 3,862 Sq Ft

    3873 N Jefferson St, Monticello, FL 32344

    Back on market due to no fault of the seller or home. Stunning 4 Bedroom, 3.5 Bath Home on 9.73 Acres with Large Detached Garage plus Oversized Attached 2 Car Garage Located just north of this spacious 3,862 square foot home sits on 9.73 acres with a tranquil creek running through the rear of the property. The home is built on high and dry ground, and not located in a flood zone or HOA.

    Stephanie Dobson Southern Land & Homes

    3873 N Jefferson St, Monticello, FL 32344
  • /32

    $285,000

    • 3 Beds
    • 2.5 Baths
    • 2,467 Sq Ft

    490 E Palmer Mill Rd, Monticello, FL 32344

    The Haile House originally built in 1893 is located in downtown Monticello FL. This wonderful victorian home features original hardwood pine floors, stain glass windows in the front parlor, original wavy glass windows throughout the home, 12 ft ceilings, a bay window and so much more! The 2,467 sqft beauty has 3 bedrooms and 2 and a half baths, fenced in yard, with a detached workshop. Less than

    Alicia Radtke All Realty Services

    490 E Palmer Mill Rd, Monticello, FL 32344
  • /18

    $229,900

    • 4 Beds
    • 3 Baths
    • 2,553 Sq Ft

    34 W Hummingbird Ln, Monticello, FL 32344

    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

    Susan Gillespie Lord & Stanley Realty, Inc.

    34 W Hummingbird Ln, Monticello, FL 32344

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