Homes for Sale in 32344

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  /21

  $349,000

  • Land
  • 15 Acres
  • $23,267 per Acre

  0000 Waukeenah Hwy, Monticello, FL 32344

  This stunning 15 acre property offers a mix of open land and wooded areas, providing a serene and private setting. Approximately 2 acres are equipped with an irrigation system, ideal for gardening, landscaping or small farming. This property includes a well-maintained barn with four spacious horse stables, perfect for equestrian enthusiasts. Power, well, and septic are already in place, making

  

  Shanna D'Attile

  Keller Williams Town & Country

  (850) 809-9683

  0000 Waukeenah Hwy, Monticello, FL 32344
• 

  

  

  /3

  $127,500

  • Land
  • 51 Acres
  • $2,500 per Acre

  000 Kinsey Rd, Monticello, FL 32344

  51 Acres of prime hunting/recreational land. Paved road access with owned easement. Wolf creek runs thrugh part of the property. $2500/Acre

  

  Buddy Witmer

  Steve C. Walker Realty, LLC

  (850) 726-3832

  000 Kinsey Rd, Monticello, FL 32344
• 

  

  

  /8

  $22,000

  • Land
  • 1.18 Acres
  • $18,644 per Acre

  874 Flatwoods, Monticello, FL 32344

  A square 1.18 acres with paved road frontage. It has a powerline easement that runs through the center of the property. It has several, abandoned, old mobile homes on the property (no titles will be given, only bill of sale) and other structures. It has about 50% wet lands and a portion of the property lies within the flood zone. It is wooded, with some, young, easy to mulch, growth and some

  

  Lynette Sirmon

  All Realty Services

  (448) 218-0926

  874 Flatwoods, Monticello, FL 32344
• 

  

  

  /31

  $60,000

  • Land
  • 8 Acres
  • $7,802 per Acre

  983 Mays Rd, Lamont, FL 32344

  Affordable recreational parcel! Buy now, build later. Ultimate weekend escape or future homestead offering fun, freedom and fresh air- 7.69 serene acres split on both sides of scenic Mays Road. Enjoy the best of two offerings: West side 5.3 acres +/- with the pond, partially cleared with lush pasture, mature shade trees and wide-open space, perfect for horses, livestock, camping, four wheeling,

  

  Lynette Sirmon

  All Realty Services

  (850) 752-4623

  983 Mays Rd, Lamont, FL 32344
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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
• 

  

  /51

  $349,900

  • Land
  • 44 Acres
  • $7,890 per Acre

  1069 N Salt Rd, Monticello, FL 32344

  44+ Acres - 1069 N Salt Road, Jefferson County, FL Located within 10 miles from downtown Monticello Quick and easy access to I-10 Secluded setting with peace and privacy Cleared homesite featuring a 40x60 pole barn Interior trail system for easy navigation and recreation Excellent deer, turkey, and duck hunting opportunities Multiple game habitats for

  Ben Jones

  1069 N Salt Rd, Monticello, FL 32344
• 

  

  /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
• 

  

  /16

  $609,878

  • Land
  • 122 Acres
  • $4,999 per Acre

  0 James Noble Rd, Greenville, FL 32331

  Millwood Timberland East is a balanced property located in a great recreational market. The Ashville area is home to numerous trophy grade recreational properties and is known for exceptional whitetail, turkey and waterfowl hunting. This property features an efficient footprint with good access and internal road infrastructure. The uplands are planted with slash pine that are approximately 8

  Bryant Peace Saunders Real Estate

  0 James Noble Rd, Greenville, FL 32331
• 

  

  /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
• 

  

  /20

  $570,000

  • Land
  • 71 Acres
  • $8,028 per Acre

  0 Aucilla Rd Unit 22696476, Monticello, FL 32344

  Located on Aucilla Rd in Monticello, FL, this versatile AG-5 property offers endless potential for residential, agricultural, and recreational use. The upland portion has been cleared, making it ideal for a homesite or multiple residences, with zoning allowing one unit per five acres and options for family transfers under county guidelines.For those looking to enjoy North Floridas natural

  Jeremiah Thompson Saunders Land

  0 Aucilla Rd Unit 22696476, Monticello, FL 32344
• 

  

  /3

  $471,000

  • Land
  • 58 Acres
  • $8,057 per Acre

  1310 Piney Woods Rd, Monticello, FL 32344

  This property contains three tax ID number. The other 2 numbers are: 03-1N-4E-0000-001F-0000 and 03-1N-4E-0000-001E-0000. A total of 58.46 acres; currently there is no for sale sign on the property. Very nice wooded tract with great location; easy access to Tallahassee. It has timber potential and would be a good home tract also. Community water is available for the property along with high

  Steve Walker Steve C. Walker Realty, LLC

  1310 Piney Woods Rd, Monticello, FL 32344
• 

  

  /38

  $7,800,000

  • Land
  • 3,089 Acres
  • $2,525 per Acre

  0 Turkey Scratch Rd Unit 18561092, Monticello, FL 32344

  Turkey Scratch Road Timberland is 3,089 Acres in Jefferson County just outside Monticello. The property features 616 Upland Acres (20%) / 2473 Wetland Acres (80%) and has 4 miles of combined road frontage on I-10, 4,450 feet of road frontage on Turkey Scratch Road, and 1,725 feet on Aucilla Road. It also has several miles of well-maintained internal roads for easy navigation and timber

  Richard Dempsey Saunders Land

  0 Turkey Scratch Rd Unit 18561092, Monticello, FL 32344
• 

  /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
• 

  /2

  $25,000

  • Land
  • 0.39 Acre
  • $64,103 per Acre

  0 Tram Rd Unit 21473387, Monticello, FL 32344

  Wooded lot located in the Wacissa area of Jefferson County; 15 to Tallahassee. Community water available to hook up to.Copyright © 2025 Tallahassee Board of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

  Steve Walker Steve C. Walker Realty, LLC

  0 Tram Rd Unit 21473387, Monticello, FL 32344
• 

  

  /18

  $1,300,000

  • Land
  • 200 Acres
  • $6,500 per Acre

  0 Gum Swamp, Greenville, FL 32331

  Millwood Timberland West is a balanced recreational asset located in the Ashville, FL region. The internal road system meanders through the ecologically diverse landscape of pine plantations, live oaks and forested wetlands. The uplands are planted in slash pine that are approximately 15 years old and ready to be thinned. The next owner will be able to thin the pines to their specification in

  Bryant Peace Saunders Real Estate

  0 Gum Swamp, Greenville, FL 32331
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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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /41

  $425,000

  • 5 Beds
  • 4 Baths
  • 3,330 Sq Ft

  4131 N Jefferson Hwy, Monticello, FL 32344

  3330 square foot home on a beautiful 6 acre property that backs up to Pine Haven Plantation! This is a solid brick home with a 2016 metal roof and a 2018 HVAC unit and well pump. The home was purchased back in 2023 and gutted along with some extensive repairs done to bones of the home. It is now waiting for the perfect person to come in and finish her out with their personal touches. The main

  Catherine Hope All Realty Services

  4131 N Jefferson Hwy, 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
• 

  

  /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
• 

  

  /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
• 

  

  /52

  $230,000

  • Land
  • 40 Acres
  • $5,750 per Acre

  3978 Quitman Hwy S, Greenville, FL 32331

  Welcome to 3978 S Quitman Hwy – 40 beautiful acres in the heart of Jefferson County, Florida. This versatile property is ideal for those seeking a private hunting retreat, weekend getaway, or future homesite. Over a quarter of the land is planted in pines, providing both aesthetic value and future timber potential. An older mobile home sits on-site, holding little value, but all essential

  Benjamin Sadler OaksFeather Realty

  3978 Quitman Hwy S, Greenville, FL 32331
• 

  

  /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
• 

  

  /3

  $45,000

  • Land
  • 2.00 Acres
  • $22,500 per Acre

  33 Kameron Dr, Waukeenah, FL 32344

  I am pleased to announce this beautiful piece of property available for purchase, consisting of 2 acres of raw land situated in the serene rural outskirts of Monticello, Florida. The asking price for this exceptional land is only $45,000. This property is nestled in the picturesque Keystone County of Florida. Jefferson County is renowned for its gently rolling hills, majestic oak trees, and the

  Meka Spencer Keller Williams Town & Country

  33 Kameron Dr, Waukeenah, FL 32344
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /11

  $26,000

  • Land
  • 2.00 Acres
  • $13,000 per Acre

  0 Flatwoods, Monticello, FL 32344

  Land for Sale – Flatwoods, FL 32344. Size: 2.0 Acres. Location: Flatwoods Road, Monticello, Florida 32344. Property Highlights: Buildable lot with plenty of space; Power available on the road; 411.75 feet of road frontage; Peaceful rural setting surrounded by large parcels; No HOA – flexible use for site-built or modular homes. About 40 minutes to Tallahassee. Ideal for a private

  Andrey Rossin CASH FLOW IN MIAMI REALTY

  0 Flatwoods, Monticello, FL 32344
• 

  

  /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
• 

  

  /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
• 

  

  /20

  $125,000

  • 3 Beds
  • 2 Baths
  • 1,836 Sq Ft

  195 E Meadow Rd, Monticello, FL 32344

  NEW Metal ROOF 2022! Welcome to the Aucilla Forest & Meadows Subdivision! Spacious 1836 square foot double wide mobile home built in 1999. 3 bedroom, 2 full bathroom on huge 2.50 acre lot! ~10 minutes to Aucilla River! Only $68/sq ft! Home needs cosmetic work that can be done over time! Primary bedroom has shower stall, garden tub + large walk-in closet. Split floor plan, huge kitchen with tons

  Chelsey Hough Keller Williams Town & Country

  195 E Meadow Rd, Monticello, FL 32344
• 

  

  /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
• 

  

  /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
• 

  

  /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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