Jefferson County FL Homes for Sale

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  /32

  $106,000

  • 4 Beds
  • 2 Baths
  • 2,070 Sq Ft

  273 W 12th Dr, Greenville, FL 32331

  This four bedroom two bath home is located in the Smokehouse Farms Community in Greenville. Situated on over five acres, this home features living and dining area combo, large kitchen, family room with fireplace, split plan with a large walk in closet in the main suite. Partially fenced with a nice sized shed. Make this your home today with a little TLC.

  Othell Broger Broger Real Estate Services

  273 W 12th Dr, Greenville, FL 32331
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  /42

  $635,000

  • 5 Beds
  • 4.5 Baths
  • 2,658 Sq Ft

  8818 Gamble Rd, Monticello, FL 32344

  Stunning turnkey home on 5.5 acres on the highly sought after Gamble Road in Jefferson County, FL. Built in 2020, this bright and spacious 5 bedroom, 4.5 bathroom home is full of custom features! Downstairs features an open concept living space with beautiful kitchen, quartz countertops and island with seating. Kitchen and dining space flow into the living room, with French doors to the patio.

  Catherine Hope All Realty Services

  8818 Gamble Rd, Monticello, FL 32344
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  /18

  $150,000

  • 2 Beds
  • 2 Baths
  • 812 Sq Ft

  1405 Florida St, Monticello, FL 32344

  Why pay rent-affordable living in this like new 2/2 singlewide on large lot. Conveniently located just north of Monticello.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 233-4922

  1405 Florida St, Monticello, FL 32344
• 

  

  

  /57

  $230,000

  • 2 Beds
  • 1 Bath
  • 1,741 Sq Ft

  265 W Seminole Ave, Monticello, FL 32344

  You must see this -Charming all-brick corner-lot home ideally located directly across from the Legion Hall and the entrance to Monticello Ecological Park—plus just a short walk to midtown shops and restaurants. The screened In front porch welcomes you inside. Inside, you’ll find wood floors (including beneath the carpet in the bonus room) and a layout that offers flexibility for today’s living.

  Karen Gillispie Keller Williams Town & Country

  265 W Seminole Ave, Monticello, FL 32344
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  /41

  $575,000

  • 4 Beds
  • 2.5 Baths
  • 2,431 Sq Ft

  234 Legacy Way, Monticello, FL 32344

  Highly Desirable Heritage Hills- Minutes from Tallahassee ! Welcome to this beautifully crafted 4-bedroom, 2.5 bath Craftsman-style home. Situated on a spacious 3- acre lot, this home offers privacy, room to roam, and timeless curb appeal. Step inside to an inviting open-concept living area featuring a cozy gas fireplace with custom buily-in bookshelves- perfect for relaxing or entertaining. The

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 230-5054

  234 Legacy Way, Monticello, FL 32344
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  /29

  $95,000

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  290 Parkway Pines Ct, Monticello, FL 32344

  Explore this three bedroom, two bathroom mobile home located on a little over half an acre in the Parkway Pines subdivision in Monticello Florida! Featuring newer carpet/vynil flooring throughout the home, a spacious front porch, and plenty of yard space for outdoor activities! Home is being offered "AS IS". Metal roof is about 3-5 years old. Original HVAC, duct work replaced summer 2025. All

  Alicia Radtke All Realty Services

  290 Parkway Pines Ct, Monticello, FL 32344
• 

  

  /35

  $375,000

  • 4 Beds
  • 3.5 Baths
  • 2,768 Sq Ft

  925 E Pearl St, Monticello, FL 32344

  Charming historic home with bonus guest cottage, located on the most beautiful oak lined street in picturesque Monticello, Florida. OWNER FINANCING AVAILABLE call for convenient terms. Enjoy small-town living in this updated home featuring a 2020 Roof, 2022 HVAC, 2025 Water Heater, Updated Electrical, CPVC and Copper Plumbing, Schedule 40 sewer piping, and mostly updated windows. New mini split

  Tom Grasberger Gaff's Realty Company

  925 E Pearl St, Monticello, FL 32344
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  /3

  $79,900

  • Land
  • 1.39 Acres
  • $57,482 per Acre

  TBD Pineview Rd, Monticello, FL 32344

  Very nice high and dry 1.39 acres, ideal for new home or mobile home.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 333-1312

  TBD Pineview Rd, Monticello, FL 32344
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  /38

  $449,900

  • 3 Beds
  • 2 Baths
  • 1,774 Sq Ft

  107 S Tarn Way, Monticello, FL 32344

  Welcome to this beautifully custom-built 3 bedroom, 2 bath home completed in 2024 and located in the desirable Hemings Pond Subdivision. Offering the perfect blend of modern construction and thoughtful upgrades, this move-in ready showcases luxury vinyl plank flooring, upgraded light fixtures, premium countertops, and elegant bath fixtures. Owner selected custom enhancements elevate the space

  Joana Villeneuve Hill Spooner & Elliott Inc

  107 S Tarn Way, Monticello, FL 32344
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  /25

  $879,900

  • 3 Beds
  • 2.5 Baths
  • 2,412 Sq Ft

  4216 W Washington Hwy, Monticello, FL 32344

  Magnolia Rise, a retreat on a 10.84 acre tract, located in the prestigious Rainey Run neighborhood, with a private entrance. Prepare to fall in love with a home that transcends ordinary living. Meticulously crafted by Hannon Construction, this 2023 architectural gem represents the pinnacle of European farmhouse design and functionality. Offering the perfect blend of modern comfort and farmhouse

  Moe Mossa Savvy Avenue, LLC

  4216 W Washington Hwy, Monticello, FL 32344
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  /50

  $599,900

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

  5301 Gentle Breeze Dr, Tallahassee, FL 32309

  BRING ANY AND ALL OFFERS!!!! A true diamond in the rough, perfectly positioned on Lake Miccosukee. A bass fisherman’s dream come true. You truly won’t find another gem like this. This stunning 10-acre waterfront estate sits right at the water’s edge, offering wide-open space ideal for horses, outdoor adventures, and total privacy. Surrounded by abundant wildlife, this property is perfect for

  Lindsay Pearson Pearson Realty Inc.

  5301 Gentle Breeze Dr, Tallahassee, FL 32309
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  /11

  $45,000

  • Land
  • 2.5 Acres
  • $18,000 per Acre

  1 W Meadow Rd, Monticello, FL 32344

  2.5 Acres of land, partially cleared for home-site. Private quiet road. All high and dry ready to build your homestead. mobile homes okay. Close to aucilla river. Convenient to Monticello, FL and Thomasville Ga. Valdosta and Tallahassee 45 minutes away. Horse Friendly area. Owner financing options available.

  Starbuck Rissman Steve C. Walker Realty, LLC

  1 W Meadow Rd, Monticello, FL 32344
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  /70

  $1,325,000

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

  221 Kiley Dr, Monticello, FL 32344

  Welcome to 221 Kiley Road in Monticello, Florida — a rare estate where vineyard charm, equestrian living, and exceptional space come together to create an unforgettable lifestyle. 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

  Wilda Sigler Keller Williams Town & Country

  221 Kiley Dr, Monticello, FL 32344
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  /49

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 3,832 Sq Ft

  4589 Ashville Hwy, Monticello, FL 32344

  Nestled on 5.56 acres of fenced pastureland, this stunning estate, is framed by majestic oak trees and welcomes you through a private gated entrance. From the rocking chair front porch to the thoughtfully designed interior, this property offers the perfect blend of luxury and country living. Living room kitchen combination with the stone fireplace creating a warm and inviting focal point. The

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 218-0015

  4589 Ashville Hwy, Monticello, FL 32344
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  /36

  $674,900

  • 5,139 Sq Ft

  625 E Washington St, Monticello, FL 32344

  Amazing Investment Opportunity as a Large family home, multi-generational property or Cash flowing investment! Own your piece of history and enjoy some great cash flow in this beautiful Downton Monticello Home. Built in 1888 and almost 4500 SF in the main house with 9 bedrooms, 7 bathrooms and common areas for the tenants. Currently set up with tenants as a BNB type property with longer term

  Lee Hall Capital City Real Estate Group

  625 E Washington St, Monticello, FL 32344
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  /60

  $700,000

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft

  925 Hiawatha Farms Rd, Monticello, FL 32344

  Custom hurricane-resistant/efficiency home on 3.6 private acres in a gated equestrian community, just 17 miles east of Tallahassee and 1 mile to I-10 (Exit 217). Built in 2013, this 2,112 sq ft home features 4 bedrooms, 3 full baths, and 9’ ceilings throughout. Constructed with Nudura ICF 12” insulated concrete exterior walls for superior strength, energy efficiency, and sound insulation.

  

  Joann Jacobs

  Coldwell Banker Hartung

  (448) 230-7519

  925 Hiawatha Farms Rd, Monticello, FL 32344
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  /16

  $549,000

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  640 Nautilus Dr, Monticello, FL 32344

  Secluded 56.37 Acres with Metal Building & Living Quarters -Western Jefferson County. This property offers privacy, versatility and room to build or expand. The land features a 2880 sq ft heavy-gauged metal building designed for both residential and workshop use. Second floor includes 1200 sf of living space currently unfinished featuring two bedrooms, kitchen and living area and one bath. A

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 231-5287

  640 Nautilus Dr, Monticello, FL 32344
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  /38

  $599,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,134 Sq Ft

  261 Hiawatha Farms S, Monticello, FL 32344

  Welcome to this stunning new construction masterpiece, meticulously designed and built by the esteemed Kasdorf Homes, LLC. This craftsman beauty is awaiting its first owners and will be ready for occupancy by the beginning of May. Spanning an impressive 2134 square feet, this home offers a spacious and open concept floor plan, perfect for modern living. The split floor plan provides privacy and

  Ross Kozloski Kozloski Realty, LLC

  261 Hiawatha Farms S, Monticello, FL 32344
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  /14

  $37,000

  • Land
  • 1 Acre
  • $37,000 per Acre

  1264 Quail Ln, Monticello, FL 32344

  Corner lot off of paved road in Lloyd Acres. Wooded, pines and hardwoods. High elevation. Mobile homes are allowed. An additional 3.30 acres available for purchase.

  Callie Rhoads The Naumann Group Real Estate

  1264 Quail Ln, Monticello, FL 32344
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  /19

  $480,000 New Construction

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

  855 S Waukeenah St, Monticello, FL 32344

  Stunning New Construction recently 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 features vinyl plank flooring, granite countertops, walk in tile shower and tub in master, upgraded trim package, and stainless appliances. Nice large back porch with deck, over looking the large

  Jared Parramore Coastwise Realty

  855 S Waukeenah St, Monticello, FL 32344
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  /54

  $525,000

  • 4 Beds
  • 3 Baths
  • 2,784 Sq Ft

  70 Generation Ct, Monticello, FL 32344

  Wow! Special opportunity to add your personal touches! Design your dream kitchen! Craftsman style home features a roomy floorplan with lots of storage nooks and crannies, huge primary suite waiting for your perfect finishes, open kitchen and all nestled on private 4.45 acres. Many of the are there to finish trim, there’s extra stone and extra tile. LVP and ceramic tile flooring throughout home,

  Lee Duggar Re/Max Professionals Realty

  70 Generation Ct, Monticello, FL 32344
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  /38

  $274,900

  • 2 Beds
  • 2 Baths
  • 1,411 Sq Ft

  490 N Cherry Ct, Monticello, FL 32344

  Step into city living just steps from Downtown Monticello, Fl. This one-story condo with private backyard blends modern convenience in this coveted over 55 neighborhood of only 8 units. 2 bedrooms & 2 baths, laundry room with stack unit, W/D included, but the favorite room in the house is the sunroom. Inside, enjoy the bright open-concept living with high ceilings, crown molding, LVP & engineered

  

  Pam Hoveland

  Landcorp, Inc.

  (448) 231-4689

  490 N Cherry Ct, Monticello, FL 32344
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  /70

  $700,000

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

  1627 Lloyd Creek Rd, Monticello, FL 32344

  Enjoy the gorgeous water views from the porch of this like-new, 2022 built home! A Gated driveway leads to your 5 acre parcel on a beautiful 10 acre spring-fed lake with great fishing. 6 ft windows and 8x8 sliding doors allow the open living, dining, and kitchen areas to view the sunny outdoors. Kitchen features a large island with seating area, stainless appliances, gas stove, and fridge with

  Nan Greynolds The Naumann Group Real Estate

  1627 Lloyd Creek Rd, Monticello, FL 32344
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  /2

  $244,900

  • 3 Beds
  • 2 Baths
  • 1,235 Sq Ft

  350 Bowman St, Monticello, FL 32344

  New construction; very convenient to downtown; house is close to completion - should be ready in about 45 days.

  Steve Walker Steve C. Walker Realty, LLC

  350 Bowman St, Monticello, FL 32344
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  /33

  $999,900

  • 3 Beds
  • 2.5 Baths
  • 4,383 Sq Ft

  728 Turney Anderson Rd, Monticello, FL 32344

  A Timeless Treasure, built by Riley Palmer Construction in 2006, this exceptional home captures the warmth and character of an early-1900s Craftsman farmhouse. It is located on 5 beautiful acres with mature pecan trees in the front and pines in the back yard. A spacious wrap around front porch welcomes you and features reclaimed New Orleans style doors and classic architectural details. Inside,

  Jared Parramore Coastwise Realty

  728 Turney Anderson Rd, Monticello, FL 32344
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  /8

  $450,000

  • Land
  • 85.26 Acres
  • $5,278 per Acre

  1899 Big Joe Rd, Monticello, FL 32344

  Known for its white tail deer, hog and turkey populations, this 85.26 acres in Jefferson County, FL would make a perfect hunting camp. Pristine pine tree property just minutes from Interstate 10 / Exit 225. Ideal Country Estate or weekend get-away. Seller financing available to qualified buyer.

  Tom Woodyard Woodyard & Associates, LLC

  1899 Big Joe Rd, Monticello, FL 32344
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  /44

  $420,000 Open Sun 2PM - 4PM

  • 5 Beds
  • 2 Baths
  • 2,324 Sq Ft

  40 W Cavallo Trail, Monticello, FL 32344

  Showings will begin at Open House on March 1st, from 2-4pm. Beautiful 5BR/2BA home on 3.13 fully fenced acres in Jefferson County, just minutes from Monticello. Built in 2006, this property blends modern comfort with horse-ready potential and includes a horse barn/stable and fencing. Fresh interior paint highlights a spacious layout featuring a cozy fireplace, dedicated laundry room, and a

  Joyce Gardner Signature Realty Professionals

  40 W Cavallo Trail, Monticello, FL 32344
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  /14

  $294,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,351 Sq Ft

  1090 Partridge Ln, Monticello, FL 32344

  Currently under construction. Interior pictures are from a previous model home. Approximately 60 days until completion. Home qualifies for USDA financing.

  Steve Walker Steve C. Walker Realty, LLC

  1090 Partridge Ln, Monticello, FL 32344
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  /24

  $179,900

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  963 Quail Ln, Monticello, FL 32344

  Great location for this property in Lloyd Acres. The property has 2.26 acres of partially wooded area. The property consists of the single family home, detached garage/carport/workshop and a singlewide mobile home. The vinyl sided home will need some repair and updating but has tremendous potential. The detached garage is large with 2 stalls. The mobile home is in need of a total renovation (or

  Van Drake Drake Realty, Inc.

  963 Quail Ln, Monticello, FL 32344
• 

  

  /49

  $375,000

  • 3 Beds
  • 2 Baths
  • 2,268 Sq Ft

  84 Lakeside Rd, Monticello, FL 32344

  This beautifully maintained modular home sits on 2.77 acres, offering peaceful waterfront living and modern updates throughout. Built in 2005 and thoughtfully upgraded, this 3-bedroom, 2-bathroom home combines comfort, style, and space for an idyllic Jefferson County setting. The expansive open-concept-style main living/dining area is perfect for entertaining or relaxing with family. An adjoining

  

  Brenna Kelly-Ward

  Kelly & Kelly Properties, Inc

  (448) 413-6516

  84 Lakeside Rd, Monticello, FL 32344
• 

  

  /13

  $70,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  40 Westview Ln, Monticello, FL 32344

  Don't judge this home by its exterior!! The outside siding shows significant deterioration, which is fully reflected in the price. However, once inside, you'll find a livable interior that's far more functional than first impressions suggest. This double-wide is currently occupied and offers ;an opportunity for a buyer willing to look past the exterior and focus on the potential within. Not

  Alicia Radtke All Realty Services

  40 Westview Ln, Monticello, FL 32344
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  /67

  $399,900

  • 4 Beds
  • 2 Baths
  • 2,314 Sq Ft

  701 Barber Hill, Lamont, FL 32336

  Just reduced! Welcome to a classic country farmhouse set on 19.21 picturesque acres, offering the space, infrastructure, and versatility today’s buyers are seeking. From the aerial view, the property unfolds as a true working farm with fenced and cross-fenced pastures, mature trees, and a thoughtfully laid-out compound of multiple outbuildings, including a barn, tobacco barn, and additional

  

  Joann Jacobs

  Coldwell Banker Hartung

  (448) 233-6452

  701 Barber Hill, Lamont, FL 32336
• 

  

  /13

  $69,900

  • Land
  • 5.01 Acres
  • $13,952 per Acre

  TBD Smokehouse Farms Dr, Greenville, FL 32331

  Drive by's won't do this property justice! This 5 acre corner parcel sits high and dry with great elevation and drainage, but from the road you can't see what makes it special. The land rises back and up the hill, revealing a park like natural setting with solid ground and mature trees - perfect for a future homesite. There is some roadside overgrowth of vines and natural vegetation plus some

  

  Lynette Sirmon

  All Realty Services

  (448) 994-3376

  TBD Smokehouse Farms Dr, Greenville, FL 32331
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  /45

  $455,995 New Construction

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

  47 Mire Ct, Monticello, FL 32344

  Amazing new construction Available Now 3 bedroom 2 bathroom by Nailed It Tallahassee LLC Luxurious master suite, Kitchen made of dreams, this is a must see! Preferred Lender offering 1% in closing costs! Photos of current home!

  Amber McKinney Hamilton Realty Advisors LLC

  47 Mire Ct, Monticello, FL 32344
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  /32

  $269,000

  • 3 Beds
  • 2 Baths
  • 1,338 Sq Ft

  1511 Spring Hollow Dr, Monticello, FL 32344

  Charming home on large .87 acre lot in established subdivision. Sunporch overlooks wooded back yard, a nature lovers paradise. Open floor plan, kitchen/dining/living room combination. 2 car garage with breezeway to the home. An additional 1 acre lot is available for sale with the home for a total of 1.87 acre for $319,000.

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 233-5401

  1511 Spring Hollow Dr, Monticello, FL 32344
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  /42

  $472,500

  • 2 Beds
  • 2 Baths
  • 2,499 Sq Ft

  75 E 5th Ct, Greenville, FL 32331

  "Fly-in" living at its finest! Located on 5 acres featuring a main residence, a guest house, an impressive 60x48 aircraft hangar + 40x48 apron with direct access to a 6,000 foot grass airstrip. Land then taxi directly to your 2 homes, hangar and fly out with ease. The two homes total sq. ft. equals 2,499 sq. ft. (one is 1152 sq. ft. and the other one is 1347 sq. ft). Located on a total of FIVE

  

  Lynette Sirmon

  All Realty Services

  (448) 256-3329

  75 E 5th Ct, Greenville, FL 32331
• 

  

  /21

  $265,900

  • 3 Beds
  • 2 Baths
  • 1,290 Sq Ft

  1125 E Dogwood St, Monticello, FL 32344

  Must see this brand new home built by Southern Construction in the downtown Monticello area. Home is complete and ready for its new owners!! Home features 3 bed, 2 baths, granite countertops, upgraded trim package, vinyl plank flooring throughout, tile bathroom and laundry floors, and stainless appliance package. Come get this beautiful home before its gone!!

  Jared Parramore Coastwise Realty

  1125 E Dogwood St, Monticello, FL 32344
• 

  

  /16

  $65,000

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft

  980 Mays St, Monticello, FL 32344

  Probate proceedings underway. Cannot close until court approval. Concrete Block 2/1 Home less than a mile from downtown Monticello! This quaint 888sqft home sits under a metal roof and only requires your vision and a little effort to become a superb starter home or investment opportunity. Property is fully fenced and on city utilities. Room measurements are approximate

  Ben Marinelli All Realty Services

  980 Mays St, Monticello, FL 32344
• 

  

  /31

  $434,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  285 Mallard Ln, Monticello, FL 32344

  *Jefferson County peaceful country living with a waterfront backdrop! Built in 2008, this well maintained 3 bedroom, 2 bath home sits on 4.89 beautifully (mostly cleared) acres offering privacy and natural beauty backing directly up to Lloyd Lake- perfect for relaxing evenings with scenic views. Pretty rocking chair front porch as well as a screened in back porch with a propane hookup for

  Shelley Duke Red Bird Realty

  285 Mallard Ln, Monticello, FL 32344
• 

  

  /28

  $185,000

  • 3 Beds
  • 2 Baths
  • 1,292 Sq Ft

  463 Murmuring Creek Rd, Monticello, FL 32344

  Move in ready home on over 5 acres in beautiful Monticello Florida. Newer Roof 2024, Freshly painted, , windows, hot water heater 2024, flooring. reduced price, No HOA

  Jennifer Atwell Ketcham Realty Group, Inc.

  463 Murmuring Creek Rd, Monticello, FL 32344

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