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

  Welcome to Your Hidden Hilltop Retreat! Perched atop a gentle rise (180 ft. above sea level) in Northeast Jefferson County, this three-story, 4-bedroom, 4-bathroom sanctuary offers a life lived deeply in tune with nature. Nestled on 5.11 acres of whimsical, lovingly tended land—where white-tailed deer browse the edges of a fenced garden and wild turkeys meander past the first floor, screened

  

  Lynette Sirmon

  All Realty Services

  (850) 930-1972

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

  $489,900

  • 3 Beds
  • 2 Baths
  • 2,061 Sq Ft

  350 Oconee, Monticello, FL 32344

  Welcome to Covey Run, a private estate community in the heart of Monticello. Your new 3 bedroom 2 bath 2 car garage sits on 2.24 acres. Home features open floor plan with primary on-suite and large walk-in closet. Kitchen is ready for the chef in mind with gas range and plenty of room for prep. Living room features 10 foot ceilings, fireplace and opens to a sunroom. House has Generac Home

  Steve Walker Steve C. Walker Realty, LLC

  350 Oconee, Monticello, FL 32344
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  /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
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  /2

  $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. More pictures coming next week.

  Steve Walker Steve C. Walker Realty, LLC

  339 Silver Lake Rd, Monticello, FL 32344
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  /48

  $525,000

  • 5 Beds
  • 3.5 Baths
  • 4,600 Sq Ft

  885 S Waukeenah St, Monticello, FL 32344

  Tucked into the charming heart of Monticello, yet only a short scenic drive to Tallahassee, this estate bridges the gap between past and present, country and capital, southern soul and worldly sophistication. Step beyond through the historic front door into a moment suspended in time where Southern grandeur, storied legacy, and modern luxury converge in a peaceful retreat just 30 minutes from the

  Jason Boone Keller Williams Town & Country

  885 S Waukeenah St, Monticello, FL 32344
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  /58

  $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
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  /28

  $420,000

  • 3 Beds
  • 2.5 Baths
  • 2,373 Sq Ft

  1205 E Pearl St, Monticello, FL 32344

  Charming 1956 Mid-Century Home. Fully Renovated with Modern Touches. Welcome to this beautifully reimagined 1956 classic, where character meets contemporary luxury. Every inch of this home has been thoughtfully renovated, blending original charm with stylish, modern upgrades. Step inside to discover a bright, open-concept living space featuring new floors, recessed lighting, and large windows

  Brian Bachman Kelly & Kelly Properties, Inc

  1205 E Pearl St, Monticello, FL 32344
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  /43

  $539,000

  • 3 Beds
  • 2.5 Baths
  • 3,054 Sq Ft

  79 Lakeside Rd, Monticello, FL 32344

  Welcome to your country escape — a timeless farmhouse nestled on 3+ scenic acres, offering the perfect blend of space, charm, and opportunity. This classic home features soaring high ceilings, oversized rooms, and a sprawling wraparound porch that invites you to sit back and soak in the peaceful surroundings. Inside, you’ll find large, light-filled living spaces with original character and room

  Michael Schilling Hill Spooner & Elliott Inc

  79 Lakeside Rd, Monticello, FL 32344
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  /47

  $459,000

  • 3 Beds
  • 2 Baths
  • 2,334 Sq Ft

  1293 Vista Rd, Monticello, FL 32344

  Country living at its finest! This beautifully maintained 3-bedroom, 2-bath brick home is nestled on 2.57 peaceful acres—just minutes from Monticello and Interstate 10. Enjoy a desirable split floor plan with hardwood floors throughout the main living areas and new carpeting in the bedrooms. The kitchen features new sparkling quartz countertops, stainless steel appliances, and abundant

  Leanne Groom The Naumann Group Real Estate

  1293 Vista Rd, Monticello, FL 32344
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  /38

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  151 N Ojibwa Rd, Monticello, FL 32344

  Spacious, Private, and Ready to Go! This 3-bed, 3-bath home sits on just over 5 acres of agricultural-zoned land, offering space, privacy, and freedom to live how you want. With 2,400 sq ft, there's plenty of room — including a bonus room over the 2-car garage with A/C, a dedicated home office space with an attached bathroom, and an oversized workshop ready for your tools, equipment, or weekend

  Clint Bailey Superior Realty Group LLC

  151 N Ojibwa Rd, Monticello, FL 32344
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  /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
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  /37

  $465,000

  • 4 Beds
  • 3 Baths
  • 2,076 Sq Ft

  376 Tecumseh Rd, Monticello, FL 32344

  BRAND NEW ROOF!! Gorgeous multigenerational, ranch style, 4 Bedroom/3 Bath home with 5th room that can be used as an office or additional bedroom. Perfect for a growing or downsizing family! Home rests on 4.60 acres of outdoor, partially wooded paradise. Enjoy tranquility from the all-season rear porch-removable panels allow you to turn room into a screened porch in minutes. Many recent updates

  Casey Skelton Pearson Realty Inc.

  376 Tecumseh Rd, Monticello, FL 32344
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  /27

  $399,000

  • 3 Beds
  • 2 Baths
  • 2,131 Sq Ft

  133 Devane Rd, Monticello, FL 32344

  Peaceful 10-Acre Country Retreat with Pool - Just Outside Chattahoochee, FL Discover the charm of country living with this spacious 3-bedroom, 2-bath single-family home located just minutes from the quaint town of Chattahoochee, Florida. Enter through the winding tree lined road that sets the stage for the home that welcomes you at the end. Set on a beautifully wooded 10-acre parcel, this 2,131

  Bubba McCants EXP Realty LLC

  133 Devane Rd, Monticello, FL 32344
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  /36

  $399,000

  • 3 Beds
  • 2 Baths
  • 2,020 Sq Ft

  259 Barnes Rd, Monticello, FL 32344

  Spacious Brick on 4.25 acres. Easy Thomasville commute. Discover peace and privacy with this well maintained brick ranch nestled in the woods. Step into the spacious living room with cozy wood burning fireplace, ideal for relaxing evenings or entertaining. Office, large utility room, 2 car garage, and workshop are some of the extras. Enjoy this quiet private setting.

  Pam Kelly Kelly & Kelly Properties, Inc

  259 Barnes Rd, Monticello, FL 32344
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  /37

  $398,000

  • 3 Beds
  • 2 Baths
  • 2,766 Sq Ft

  205 N Rhodes St, Monticello, FL 32344

  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

  Pam Kelly Kelly & Kelly Properties, Inc

  205 N Rhodes St, Monticello, FL 32344
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  /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
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  /3

  $499,900 New Construction

  • 4 Beds
  • 3 Baths
  • 1,798 Sq Ft

  855 S Waukeenah St, Monticello, FL 32344

  Stunning New Construction home currently being 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 will feature vinyl plank flooring, granite countertops, walk in tile shower and tub in master, upgraded trim package, and stainless appliances. Some finishes have been selected by builder,

  Jared Parramore Coastwise Realty

  855 S Waukeenah St, Monticello, FL 32344
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  /24

  $430,000 New Construction

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

  173 Deerfield Ln, Monticello, FL 32344

  Welcome to this beautifully maintained 3-bedroom, 2-bath home offering the perfect blend of peaceful country living and modern upgrades. Nestled on a full acre of land, this charming property is a rare gem with no HOA restrictions—giving you the freedom to truly make it your own. Step inside and be captivated by the open and inviting floor plan, featuring both a formal living room and a cozy

  Pamela Jordan-williams Superior Realty Group LLC

  173 Deerfield Ln, Monticello, FL 32344
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  /3

  $469,995 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,940 Sq Ft

  52 Mire Ct, Monticello, FL 32344

  Amazing new construction 3 bedroom 3 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

  52 Mire Ct, Monticello, FL 32344
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  /41

  $460,995 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
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  /33

  $220,000

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

  1065 S Mulberry St, Monticello, FL 32344

  This southern home located in the heart of Monticello is the perfect 2/2 for a starter family looking to settle down or a fast fixer upper! There is so much potential with good bones from the old hardwood floors to the floor-to-ceiling windows. Quiet, cute neighborhood in walking distance to the roundabout with restaurants and antique shops or to the grocery store. This house has a big backyard

  Katherine Gonzalez Pearson Realty Inc.

  1065 S Mulberry St, Monticello, FL 32344
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  /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
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  /41

  $349,500

  • 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
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  /14

  $189,000

  • 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
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  /55

  $1,100,000

  • 5 Beds
  • 5.5 Baths
  • 4,700 Sq Ft

  1165 Dills Rd, Monticello, FL 32344

  Nature Lover’s Dream — a rare opportunity to own a stunning custom estate offering peace, privacy, and over 21 acres of unspoiled natural beauty. Thoughtfully designed for both comfort and function, this spacious home boasts more than 4,500 square feet of living space. Inside, enjoy a gourmet kitchen with gas range and butler’s pantry, formal and casual living areas, a cozy library, and a

  Callie Rhoads The Naumann Group Real Estate

  1165 Dills Rd, Monticello, FL 32344
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  /29

  $295,000

  • 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 cedar 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 house

  Trevor Ann Clark Keller Williams Town & Country

  9497 Gamble Rd, Monticello, FL 32344
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  /47

  $329,900

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

  1530 Sweetbay Ct, Monticello, FL 32344

  Beautiful 2021 built 3/2 home on quiet cul-de-sac across from a gorgeous green space with mature trees! Stunning light and bright features with an updated kitchen and baths, including laminate light oak wood flooring, granite counters, stainless appliances, covered back porch and two car garage. This home is a must-see!

  Amber Renaud The Nova Group Realty

  1530 Sweetbay Ct, Monticello, FL 32344
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  /4

  $259,900

  • 5 Beds
  • 3 Baths
  • 4,026 Sq Ft

  620 Hill St, Monticello, FL 32344

  Welcome to this charming home located at 620 Hill St in Monticello, FL. This delightful property features a spacious layout with multiple bedrooms and bathrooms, providing ample space for comfort and functionality. Enjoy the serene surroundings and beautiful exterior, complemented by a well-maintained yard. Inside, you'll find a bright and inviting living area, a modern kitchen, and elegant

  Steven Koleno Beycome of Florida LLC

  620 Hill St, Monticello, FL 32344
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  /42

  $614,900

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

  181 Heritage Blvd, Monticello, FL 32344

  Craftsman style house in Heritage Hills subdivision~ Seller contemplating backup contracts~ The house features 3 bedrooms/2 bathrooms and is energy efficient (Green Certified) ~ Luxurious hardwood flooring and a deluxe primary bathroom with separate jetted tub & large shower ~ Custom built-in cabinets in the living room and office ~ Regal craftsman style interior trim throughout and

  Mariela Bartens Coldwell Banker Hartung

  181 Heritage Blvd, Monticello, FL 32344
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  /27

  $240,000

  • 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
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  /42

  $375,000

  • 4 Beds
  • 3 Baths
  • 2,223 Sq Ft

  155 E Seminole Ave, Monticello, FL 32344

  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 en suite 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

  Catherine Hope All Realty Services

  155 E Seminole Ave, Monticello, FL 32344
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  /18

  $749,000

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft

  5301 Gentle Breeze Dr, Tallahassee, FL 32309

  Rare find. 10+/- acres located in Leon County, Florida on Lake Miccosukee. Rustic homestead with 455 feet of breathkaking views of the lake. Very secluded with lots of privacy. 1,650 SF lodge/home included in sale. Fantastic ducking, deer and turkey hunting, as well as world class fishing in your backyard! Entire home Generac generator included. Gentle Breeze Drive is located approximately

  Gerald McArthur Gerald McArthur Gulf Coast Real Estate Advisors, LLC

  5301 Gentle Breeze Dr, Tallahassee, FL 32309
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  /40

  $600,000

  • 4 Beds
  • 3.5 Baths
  • 2,771 Sq Ft

  44 S Ojibwa Rd, Monticello, FL 32344

  Back on the market due to Buyers Financing falling through... Now is your time to escape the hustle and enjoy peaceful country living with the convenience of modern amenities! This spacious 4 bedroom, 3.5 bathroom home offers 2,771 square feet of well-designed space sitting on 5 beautiful acres with producing pecan trees. Whether you're ready to start your homesteading journey or simply want

  Brett Miller Hollifield Real Estate Group

  44 S Ojibwa Rd, Monticello, FL 32344
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  /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
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  /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
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  /42

  $675,000

  • 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
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  /42

  $265,000

  • 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. Additional

  Pam Kelly Kelly & Kelly Properties, Inc

  2436 N Jefferson Hwy, Monticello, FL 32344
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  /19

  $299,000

  • 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
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  /40

  $1,390,000

  • 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

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