Monticello, FL Homes

• 

  

  

  /29

  $60,000 Sold Apr 29, 2025

  • 2,612 Sq Ft
  • $23/SF
  • 52 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1914

  1150 Sage St, Monticello, FL 32344

  Built in 1914, this historic home in the heart of Monticello, Florida, offers a rare opportunity to own a piece of the past. With 5 spacious bedrooms and 2 full bathrooms, this charming property sits on a generous 0.63-acre lot, providing ample outdoor space. While the home requires significant renovation, it boasts original historical elements throughout, including beautiful hardwood floors,

  Gabriela Sacco All Realty Services

  1150 Sage St, Monticello, FL 32344
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  /28

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,323 Sq Ft

  1993 Hartsfield Rd, Monticello, FL 32344

  1993 Hartsfield Rd, Monticello, FL 32344
• 

  

  

  /42

  $449,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,832 Sq Ft

  4710 Waukeenah Hwy, Monticello, FL 32344

  Monticello living is good, peaceful living. This home is ready for a multi-generational family, or a family with loads of relatives and friends to entertain. This three bedroom, two bath home has an adjacent mother in law suite complete with bedroom, kitchen, bath and living room. Located on two acres with a 2025 a/c unit, 2019 roof, large screened and unscreened porch, 3 pad carport, 3

  Fay Armstrong Keller Williams Town & Country

  4710 Waukeenah Hwy, Monticello, FL 32344
• 

  

  

  /14

  $230,000 Sold Apr 24, 2025

  • 1,316 Sq Ft
  • $175/SF
  • 26 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1970

  523 Silver Lake Rd, Monticello, FL 32344

  Prime location in NE Jefferson County! Just 5 minutes to historic Monticello with easy travel to Tallahassee, Thomasville and Quitman. Lots of properties boast horse potential, but this 12 acre parcel truly has room for all your equine needs. High and dry with paved roads. Unlock the potential of this home that’s ready for a transformation! While extensive repairs are needed, this property

  Brian Bachman Kelly & Kelly Properties, Inc

  523 Silver Lake Rd, Monticello, FL 32344
• 

  

  

  /31

  Est $393,479 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft

  1613 Yaupon Ct, Monticello, FL 32344

  1613 Yaupon Ct, Monticello, FL 32344
• 

  

  /40

  $419,900 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,809 Sq Ft

  115 Crooked Creek Ln, Monticello, FL 32344

  New 2025 Built Home in Crooked Creek on a spacious .72 acre lot! This open plan features 4 bedrooms, 2 bathrooms, 2 car garage, and beautiful shiplap accent walls. The kitchen has a light and bright design with white cabinets, quartz counters, subway tile backsplash, and GE stainless appliances. LVP flooring throughout (tile in baths), fireplace, covered back patio, and pre-wired for security and

  Amber Renaud The Nova Group Realty

  115 Crooked Creek Ln, Monticello, FL 32344
• 

  

  /39

  $321,000 Sold Apr 24, 2025

  • 1,680 Sq Ft
  • $191/SF
  • 43 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2022

  1260 E Washington St, Monticello, FL 32344

  Beautiful Modern Home on a Spacious corner Lot. Built in 2022, this stunning 1,680 sq. ft. home offers modern living with an open floor plan, perfect for entertaining. Featuring three bedrooms and two bathrooms, this energy-efficient home boasts a stylish kitchen, a convenient mudroom, and a two-car carport. Located near downtown Monticello, you'll enjoy easy access to the local shops, dining,

  Shanna D'Attile Keller Williams Town & Country

  1260 E Washington St, Monticello, FL 32344
• 

  

  /3

  Est $62,000 Not Listed For Sale

  420 N Forest Ct, Monticello, FL 32344

  420 N Forest Ct, Monticello, FL 32344
• 

  

  /42

  $459,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,555 Sq Ft

  4287 Bassett Dairy Rd, Monticello, FL 32344

  Rare COUNTRY Farmhouse OASIS AWAITS! – Discover the perfect blend of rustic charm in this stunning 5-bedroom, 3-bathroom home, nestled on five fully fenced acres of picturesque pastureland. Located just 15 minutes from downtown Monticello, this peaceful retreat offers breathtaking views, abundant wildlife, and plenty of space for your pets to roam. Step inside to a beautifully updated,

  Destiny Jones Keller Williams Town & Country

  4287 Bassett Dairy Rd, Monticello, FL 32344
• 

  

  /27

  $384,000 Sold Apr 22, 2025

  • Land
  • 25 Acres
  • $15,534 per Acre

  • 812 Days On Market

  162 Natural Bridge Rd, Monticello, FL 32344

  LOCATED ON THE CORNER OF FANLEW ROAD AND NATURAL BRIDGE ROAD IN A LITTLE COMMUNITY CALLED FANLEW. THIS COMMUNITY SERVED SAWMILLS AND TURPENTINE STILLS THAT ONCE POPULATED THIS AREA. IT STRADDLES JEFFERSON WAKULLA AND LEON COUNTY. THE PROPERTY IS A MIXTURE OF PINES AND HARDWOODS AND SPORTS AN ORIGINAL HOMESTEAD, NOT LIVEABLE. THERE IS A MOBILE HOME ON THE PROPERTY WITH WELL, POWER AND SEPTIC. LOTS

  Amy Crain The American Dream

  162 Natural Bridge Rd, Monticello, FL 32344
• 

  

  /11

  Not Listed For Sale

  xxx St Augustine Parcel #4 Rd, Monticello, FL 32344

  xxx St Augustine Parcel #4 Rd, Monticello, FL 32344
• 

  

  /42

  $699,000

  • 5 Beds
  • 5 Baths
  • 3,770 Sq Ft

  974 Hiawatha Farms Rd, Monticello, FL 32344

  New roof w/ acceptable offer, 2025 HVAC. Gated, horse friendly community of Hiawatha Farms is just minutes from the hustle and bustle of "city" life. Property spans over 6 acres. The main home offers 3 bedrooms and 3 full bathrooms, featuring a spacious layout designed for everyday living and effortless entertaining. Just steps away, a detached 2-bedroom, 2-bath in-law suite provides the ideal

  Kayana Gaines Hill Spooner & Elliott Inc

  974 Hiawatha Farms Rd, Monticello, FL 32344
• 

  

  /27

  $399,900 Sold Apr 21, 2025

  • 1,601 Sq Ft
  • $250/SF
  • 129 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  81 Coopers Pond Rd, Monticello, FL 32344

  New build, under construction! Completion date set for April 2025. Beautiful, private lot on 2.62 acres, close to downtown Monticello and no HOA!! 5 mins to I-10 and 4 mins to US90 - - > see similar new build, under construction @ 149 Coopers Pond on 1.05 acres @ $349,900. Highlights of builder specs are as followed: - 1601sqft - 3 bedrooms - 2 full baths - 10' tray ceiling in living room - LVP

  Tiffany Kasdorf The Nova Group Realty

  81 Coopers Pond Rd, Monticello, FL 32344
• 

  

  /14

  Est $348,261 Not Listed For Sale

  • 2 Beds

  4131 Ashville Hwy, Monticello, FL 32344

  4131 Ashville Hwy, 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
• 

  

  /40

  $425,000 Sold Apr 18, 2025

  • 3,174 Sq Ft
  • $134/SF
  • 27 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1895

  310 E Dogwood St, Monticello, FL 32344

  Step into history with the breathtaking Camellia House, a stunning Queen Anne-style home built in 1895-96 by William Bishop, a prominent local business owner with ties to the tung oil, retail, and lumber industries. Originally crafted as a wedding gift for his eldest sister, this home boasts intricate features and craftsmanship typically reserved for affluent families of the era. Its beauty has

  Devin Lohman Lohman Realty LLC

  310 E Dogwood St, Monticello, FL 32344
• 

  

  /38

  Est $202,416 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,276 Sq Ft

  5118 E Washington Hwy, Monticello, FL 32344

  5118 E Washington Hwy, 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
• 

  

  /34

  $250,000 Sold Apr 17, 2025

  • 1,731 Sq Ft
  • $144/SF
  • 83 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1994

  194 Deer Run Rd, Monticello, FL 32344

  Enjoy the peaceful vibes of this creekside Barndominium in the woods. This property has quaint country living upstairs to include the primary bedroom, on suite bathroom and large walking closet, antique wood stove and a beautiful lookout porch in the rear of the property. Downstairs you have plenty of open space for entertaining your guests including 2 bedrooms, on suite bathroom and laundry as

  Christopher Taylor Xcellence Realty

  194 Deer Run Rd, Monticello, FL 32344
• 

  

  /5

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,128 Sq Ft

  271 Tecumseh Rd, Monticello, FL 32344

  271 Tecumseh Rd, 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
• 

  

  /34

  $550,000 Sold Apr 15, 2025

  • 2,126 Sq Ft
  • $259/SF
  • 107 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2007

  136 Bob White Trail, Monticello, FL 32344

  Make this piece of paradise your own! As you pull into the driveway, you will feel as if you have escaped the stresses of every day life and have just arrived at your vacation destination. This property features a beautiful home, ample outdoor entertaining space, two ponds (one fully stocked including a duck), chicken coup, a pole barn, workshop with space for a man cave/game room, and 10 acres

  Angela Wills Team Wills Real Estate Group

  136 Bob White Trail, Monticello, FL 32344
• 

  

  /16

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,801 Sq Ft

  157 White Oak Dr, Monticello, FL 32344

  157 White Oak Dr, 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
• 

  

  /19

  $120,000 Sold Apr 15, 2025

  • 2,600 Sq Ft
  • $46/SF
  • 255 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1956

  1385 Florida Ave, Monticello, FL 32344

  **Multiple Offers** *Short Sale 3rd Party Approval Required* Main House 3Bdrm 2Ba w/attached Apartment/2Bdrm 1Ba In-Law Suite w/Kitchen, Living Area, Private Entrance & separate Driveway. Single Family Home, One Home w/Apartment as Rental, or Multi-Family/Generational Living. Corner Double Lot. Roof Replacement & HVAC (Main House) needed. Updates/Upgrades and General TLC needed. Buyer to verify

  Christopher Chaback Keller Williams Town & Country

  1385 Florida Ave, Monticello, FL 32344
• 

  

  /39

  Est $482,762 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  210 Deer Run, Monticello, FL 32344

  210 Deer Run, 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
• 

  

  /17

  $189,000 Sold Apr 02, 2025

  • 2,525 Sq Ft
  • $75/SF
  • 233 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1960

  485 Morris Rd, Monticello, FL 32344

  New Roof! New HVAC! Some repairs needed such as finishing half bath. Nearly a half acre of stunning backyard on the lake with outbuilding and shed for picnics and gatherings. Enclosed carport increases living/gathering space inside! So much opportunity here!

  Susan Gillespie Lord & Stanley Realty, Inc.

  485 Morris Rd, Monticello, FL 32344
• 

  

  /41

  Not Listed For Sale

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

  927 Quail Ln, Monticello, FL 32344

  927 Quail Ln, 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
• 

  

  /13

  $34,000 Sold Mar 31, 2025

  • 660 Sq Ft
  • $52/SF
  • 27 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1911

  265 Bowman St, Monticello, FL 32344

  Great potential to build a new home just steps away from historic downtown Monticello, the courthouse, restaurants, and shops! There are beautiful homes across the street making this an idea piece of land to build a new home. The property that is currently on this lot is in very poor condition and is most likely a tear down or at minimum a gut-job but lots of great potential on this one!

  Amber Renaud The Nova Group Realty

  265 Bowman St, Monticello, FL 32344
• 

  

  /36

  Est $289,595 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,421 Sq Ft

  275 Rudolph Ln, Monticello, FL 32344

  275 Rudolph Ln, Monticello, FL 32344
• 

  

  /20

  $139,000

  • 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 $75/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
• 

  

  /3

  $72,000 Sold Mar 31, 2025

  • Land
  • 38 Acres
  • $1,891 per Acre

  • 62 Days On Market

  4019 Ashville Hwy Unit o, Monticello, FL 32344

  Total of 38.07 acres in desirable Ashville Highway area of Monticello. Five miles from Downtown. East Jefferson County, known for beautiful rolling hills, lined with majestic century oaks. 12.35-acre parcel with an older mobile home (minimal value) fronting Ashville Highway, and an additional 25.72-acre tract on Steen Road 1.1 mile from the 12-acre parcel on Ashville Highway. The older mobile

  Sarah Scott Coldwell Banker Hartung

  4019 Ashville Hwy Unit o, Monticello, FL 32344
• 

  

  /11

  Est $97,527 Not Listed For Sale

  • 2 Beds

  161 Meadow Dr, Monticello, FL 32344

  161 Meadow Dr, 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
• 

  

  /32

  $390,000 Sold Mar 27, 2025

  • 1,803 Sq Ft
  • $216/SF
  • 90 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1987

  39 Indian Hills Rd, Monticello, FL 32344

  Beautiful four bedroom 2 bath home; spacious kitchen with coffee bar and second sink; formal dining room; cozy living room with a wood-burning fireplace; this leads you to a large deck with a 30 foot pool. Walk-in closet in master bath; variety of fruit trees and flowers located on 5 high and dry acres. 12x20 shed with electric, AC & water. Pole barn. Quick access to Tallahassee. Also shown by

  Steve Walker Steve C. Walker Realty, LLC

  39 Indian Hills Rd, Monticello, FL 32344
• 

  

  /3

  Est $119,928 Not Listed For Sale

  • 30000 Beds

  393 E Glenn Rd, Monticello, FL 32344

  393 E Glenn Rd, 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
• 

  

  /35

  $541,500 Sold Mar 27, 2025

  • 1,945 Sq Ft
  • $278/SF
  • 67 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2024

  129 White Oak Dr, Monticello, FL 32344

  The builder is offering a $10,000 buyer's credit for closing costs or interest rate buy down. Beautifully appointed home with 4 bedrooms, flex room, and commercial style kitchen backs up to 100 acre greenspace. Watch the deer and turkeys in your own yard from the covered porch. Beautiful quartz countertops, oversize drawers, and upscale appliances with 36" gas range with griddle. Tray ceilings

  Marshall Gibbs Capital City Real Estate Group

  129 White Oak Dr, Monticello, FL 32344

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