Jefferson County FL Homes for Sale

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  /42

  $447,500

  $25K PRICE DROP

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

  75 E 5th Ct, Greenville, FL 32331

  Escape the congestion and fly into your own private rural retreat featuring two seperate living quarters, expansive hangar space and direct access to a 6,000 foot grass airstrip. Not your typical cookie cutter community! 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. Taxi directly

  

  Lynette Sirmon

  All Realty Services

  75 E 5th Ct, Greenville, FL 32331
• 

  

  

  /33

  $329,000

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  233 Attatulga Rd, Lamont, FL 32336

  Spacious Triplewide mobile home on 5 private acres, plenty room for family and guests, 4 bedrooms, 3 baths, open floor plan. Huge master suite (12x25), additional bedroom with private bathroom. Huge deck for entertaining or just enjoying nature. Open pole barn and carport. Enjoy peaceful country living with ample outdoor space for animals, hobbies, or recreation. Conveniently located with easy

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  233 Attatulga Rd, Lamont, FL 32336
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  /18

  $25,000

  • Land
  • 4 Acres
  • $6,250 per Acre

  TBD S Salt Rd, Monticello, FL 32344

  This beautiful old Florida habitat is great for wildlife observation, birding, native forest growth, riding four-wheelers, building nesting boxes for ducks and bats or a hammock and a place to get away for primitive camping. Costco in Tallahassee, Florida is 30.4 miles and Walmart Supercenter in Perry, Florida is 32.1 miles. Monticello, Florida is 9.3 miles for Ice Cream and boutiques, shops,

  

  Lynette Sirmon

  All Realty Services

  TBD S Salt Rd, Monticello, FL 32344
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  /60

  $539,500

  • 4 Beds
  • 2 Baths
  • 1,718 Sq Ft

  333 N Post Oak Cir, Lloyd, FL 32344

  ENJOY THE QUIET SPACE OF THE SANCTUARY IN LLOYD*JUST 20 MINUTES FROM TALLAHASSEE* THIS FOUR BEDROOM TWO BATH HOME WAS BUILT IN 2020 WITH STYLISH FIXTURES AND DESIGN* ENJOY ONE ACRE ON A CORNER LOT WITH A FULLY FENCED BACKYARD* PLENTY OF SPACE FOR A BIG FAMILY AND PETS TO ROAM* THE HOME FEATURES A SPLIT BEDROOM FLOOR PLAN WITH A GORGEOUS OPEN LIVING, DINING AND KITCHEN SPACE* 2 CAR GARAGE AND

  

  Sarah Eden

  Eden & Company

  333 N Post Oak Cir, Lloyd, FL 32344
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  /7

  $135,000

  • Land
  • 10 Acres
  • $13,500 per Acre

  576 Cox Rd, Monticello, FL 32344

  Looking for privacy, this 10 acres provides an ideal homesite with some clearing for your homesite completed. The balance of the land is woorded with a mix of hardwoords and pines. Some of the land is in welands/flood which provides a nice buffer for privacy and a wildlife habitat. There is a well/pump (no tank), an older septic, and power pole. 15 ft easement leads to the property. Located just

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  576 Cox Rd, Monticello, FL 32344
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  /56

  $1,175,000

  • 3 Beds
  • 2 Baths
  • 2,612 Sq Ft

  1590 Tyson Rd, Monticello, FL 32344

  Experience the beauty and tranquility of North Florida living on this stunning estate located just south of Monticello with an easy commute to Tallahassee. This remarkable property features a mature pecan grove, two scenic ponds, along with a creek and open pasture perfect for horses or livestock. The centerpiece of the property is a beautifully crafted home filled with warmth, charm, and custom

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  1590 Tyson Rd, Monticello, FL 32344
• 

  

  /25

  $164,900

  $60K PRICE DROP

  • Land
  • 14.9 Acres
  • $11,067 per Acre

  Lot 8 Sneads Dr, Greenville, FL 32331

  Seller Motivated to Sell! Discover 14.9 acres of pristine residential/recreational land along the Upper Aucilla River, near Sneads Lake in Jefferson County, Florida. This unique property offers a rare combination of upland and waterfront ownership with a portion of the property submerged by the flowing river. "Own out into & beyond the river channel (all the way to other bank) on the "Aucilla

  

  Lynette Sirmon

  All Realty Services

  Lot 8 Sneads Dr, Greenville, FL 32331
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  /4

  $99,500

  $26K PRICE DROP

  • Land
  • 5.05 Acres
  • $19,703 per Acre

  455 E Duck Pond Dr, Greenville, FL 32331

  This natual beauty of 5 acres with house and shed is priced for land value. The delapidated structures holds little to no value. With ownership afar, the property has been untouched for years. Hinting at what once was and what could be again, this property invites a lifestyle of peace and seclusion giving you a unique opportunity to create your own sanctuary complete with a pond that mirrors the

  

  Ursula Hannah

  1st Realty Appraisal Inc

  455 E Duck Pond Dr, Greenville, FL 32331
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  /37

  $345,000

  $75K PRICE DROP

  • 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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  /38

  $267,900

  • 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.

  490 N Cherry Ct, Monticello, FL 32344
• 

  

  /4

  $425,000

  • Land
  • 33.26 Acres
  • $12,778 per Acre

  TBD Cavallo Trail, Lloyd, FL 32344

  33+ acres in very nice rural subdivision. All wooded and will need some clearing for a homesite. Easy access to Tallahassee. Community water is available with tap in charge approx. $2500.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD Cavallo Trail, Lloyd, FL 32344
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  /70

  $2,000,000

  • 7 Beds
  • 7 Baths
  • 5,756 Sq Ft

  305 Old Lloyd Rd, Monticello, FL 32344

  Welcome to a rare opportunity to own a true estate property where space, craftsmanship, and privacy come together on 18 beautiful acres. This impressive 7-bedroom, 5 full bath, 2 half bath two-story home offers a thoughtfully designed layout ideal for both everyday living and entertaining on a grand scale. Upstairs features 4 bedrooms and 2 full baths, while the downstairs includes 2 bedrooms,

  

  Chance Shutes

  Keller Williams Town & Country

  305 Old Lloyd Rd, Monticello, FL 32344
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  /8

  $69,000

  • Land
  • 10.2 Acres
  • $6,765 per Acre

  tbd E 2nd Way, Greenville, FL 32331

  10.2 acre wooded wonderland, corner acreage fronting on 3 roads. Will sell as 2 - 5 acre parcels for $39,500 for each parcel.

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  tbd E 2nd Way, Greenville, FL 32331
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  /2

  $65,000

  $10K PRICE DROP

  • Land
  • 1.7 Acres
  • $38,235 per Acre

  TBD Scott Dr, Monticello, FL 32344

  1.7 acres, two lots hidden in Monticello. Will not divide. Private setting with Plantation to the west. There is a 15 ft recorded easement to the property but currently working on additional road access. No sign on property. .

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD Scott Dr, Monticello, FL 32344
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  /60

  $550,000

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

  925 Hiawatha Farms Rd, Monticello, FL 32344

  (One or more photos has been virtually staged) 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,

  

  Joann Jacobs

  ROGERS BARRY, REALTOR

  925 Hiawatha Farms Rd, Monticello, FL 32344
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  /51

  $398,900

  $26K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,127 Sq Ft

  1628 N Jefferson Hwy, Monticello, FL 32344

  Picturesque, 3/2, brick beauty with a whimsical style that evokes the charm of a traditional storybook estate, with 3,127 sq. ft., bordering a large acreage holding on 2 sides. Beautiful attributes from the 1955 era such as cedar lined closet, crystal door knobs, original oak floors, wide baseboards, double bay windows, 24x10 screened porch and entertainment deck. Lifetime metal Roof! Boasting

  

  Lynette Sirmon

  All Realty Services

  1628 N Jefferson Hwy, Monticello, FL 32344
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  /27

  $349,000

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

  8156 Waukeenah Hwy, Monticello, FL 32344

  Rare Find! Country Living on 1 Acre-No HOA! Enjoy peaceful country living on a full 1-acre property with no HOA restrictions. This spacious 1774 square foot home features 3 bedrooms and 2 bathrooms with a bright open concept layout. The home features LVP flooring throughout, fresh interior paint in main living area, and a new roof in 2023 for added piece of mind. The primary suite includes a

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  8156 Waukeenah Hwy, Monticello, FL 32344
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  /21

  $172,500

  • Land
  • 10 Acres
  • $17,250 per Acre

  TBD Rainey Run, Monticello, FL 32344

  Gated rural community, lakefront 10 acres with large hardwoods. Tranquility awaits, gently sloping land with some clearing.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD Rainey Run, Monticello, FL 32344
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  /57

  $529,000

  $56K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,187 Sq Ft

  515 E Palmer Mill Rd, Monticello, FL 32344

  **MOTIVATED SELLERS - CONCESSION(S) BEING OFFERED** Remarkable, peaceful in-town oasis on 3.54 acres! An incredible find in the heart of downtown Monticello, FL. Not only is this home located on a private 3.54 acre spread, surrounded by a perimeter of natural foliage, but the home itself has been beautifully updated, blending the charm of old and the convenience of new. The 3 bedroom/3 bathroom,

  

  Brenna Kelly-Ward

  Kelly & Kelly Properties, Inc

  515 E Palmer Mill Rd, Monticello, FL 32344
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  /67

  $425,000

  $25K PRICE INCREASE

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

  701 Barber Hill, Lamont, FL 32336

  (One or more photos has been virtually staged) 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,

  

  Joann Jacobs

  ROGERS BARRY, REALTOR

  701 Barber Hill, Lamont, FL 32336
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  /35

  $435,000

  Open Sun 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,919 Sq Ft

  1680 Willow Rd, Monticello, FL 32344

  Built in 2021 | 1,919 Sq. Ft. | Modern Upgrades | Move-In Ready Welcome home to this beautifully maintained 2021-built residence offering approximately 1,900 square feet of thoughtfully designed living space with today’s most sought-after features. This move-in ready home boasts an open-concept floor plan, durable luxury vinyl plank (LVP) flooring, abundant natural light, and high-end finishes

  

  Chance Shutes

  Keller Williams Town & Country

  1680 Willow Rd, Monticello, FL 32344
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  /14

  $200,000

  • 3 Beds
  • 1.5 Baths
  • 1,304 Sq Ft

  1550 Tennessee Ave, Monticello, FL 32344

  Charming and affordable home on the North side of Monticello in Nobles Subdivision. 3 BR 1.5 Baths. Upgrades in 2021 include new ac, new water heater, new roof. Recent interior paint. Large fenced backyard.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  1550 Tennessee Ave, Monticello, FL 32344
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  /70

  $2,785,850

  • 7 Beds
  • 7 Baths
  • 5,756 Sq Ft

  305 Old Lloyd Rd, Monticello, FL 32344

  Welcome to a rare opportunity to own a true estate property where space, craftsmanship, and privacy come together on 70 beautiful acres. Only 15 minutes to Whole foods & trader Joe's This impressive 7-bedroom, 5 full bath, 2 half bath two-story home offers a thoughtfully designed layout ideal for both everyday living and entertaining on a grand scale. Upstairs features 4 bedrooms and 2 full

  

  Chance Shutes

  Keller Williams Town & Country

  305 Old Lloyd Rd, Monticello, FL 32344
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  /12

  $165,000

  $10K PRICE DROP

  • Land
  • 10.47 Acres
  • $15,759 per Acre

  5936 Vista Rd, Monticello, FL 32344

  Perfect opportunity to own 10+ acres to build your dream home on this blank slate. Lot is mostly flat and backs up to a power line so no building behind the property. Abundant wildlife present (deer and turkey) and bring all your yard animals. Ride up Vista Road to see your neighbors on larger lots to Waukeenah Hwy to visit the beautiful Monticello Vineyards and Winery. Lot dimensions are

  

  Jacquelynn Harrison-Cofty

  Advantage Premier Realty LLC

  5936 Vista Rd, Monticello, FL 32344
• 

  

  /55

  $765,000

  • 3 Beds
  • 2.5 Baths
  • 2,436 Sq Ft

  9901 Gamble Rd, Monticello, FL 32344

  PRIVATE 20-ACRE ESTATE MINUTES FROM TALLAHASSEE - TRAILS, WILDLIFE, PASTURE & CUSTOM HOME (ADJOINING 21 ACRES AVAILABLE-MLS#400837) Nestled among majestic oaks and rolling countryside, this exceptional estate offers a rare combination of privacy, natural beauty and comfortable country living. Beyond the gated entrance lies a beautiful setting of open land, mature trees, and abundant wildlife,

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  9901 Gamble Rd, Monticello, FL 32344
• 

  

  /19

  $239,000

  • 3 Beds
  • 1 Bath
  • 1,164 Sq Ft

  220 Eaton St, Monticello, FL 32344

  Very convenient location in the heart of Monticello. Excellent condition. Very good condition, new roof, new windows, newer flooring throughout. 10X12 storage shed.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  220 Eaton St, Monticello, FL 32344
• 

  

  /4

  $130,000

  • Land
  • 9.96 Acres
  • $13,052 per Acre

  00 Mallard Blue Jay Ln Unit 2/3, Monticello, FL 32344

  The listing contains (2) adjacent raw land parcels in the Lloyd Acres Subdivision = 9.96 acres total. See parcel IDs: 18-1N-4E-0113-000C-0010 (6.41 acres; Mallard Lane) + 18-1N-4E-0112-000C-0050 (3.55 acres; Bluejay Rd). Look for real estate signs (2) to help identify the acreage for sale. The property is zoned Residential-01 (1 home/1 acre), making it a great opportunity for someone wanting to

  

  Brenna Kelly-Ward

  Kelly & Kelly Properties, Inc

  00 Mallard Blue Jay Ln Unit 2/3, Monticello, FL 32344
• 

  

  /45

  $1,805,000

  • Land
  • 192 Acres
  • $9,401 per Acre

  Vacant N Salt Rd, Monticello, FL 32344

  192 Acre Organic Cattle Farm in Jefferson County, Florida192 acre organic cattle farm located in beautiful Jefferson County, FloridaCertified organic operation for 20+ years with a long-standing history of sustainable land stewardshipFully fenced and cross-fenced for efficient cattle rotation and livestock managementImproved pastureland ideal for

  

  Ben Jones

  Mossy Oak Properties Southern Land and Homes, LLC

  Vacant N Salt Rd, Monticello, FL 32344
• 

  

  /30

  $175,000

  • 3 Beds
  • 1 Bath
  • 1,662 Sq Ft

  167 Phelps Rd, Lamont, FL 32336

  Charming 3BR/1BA home with incredible potential, nestled on a gorgeous and private one acre lot with no neighbors in sight. The property is filled with beautiful Camelia trees, creating a serene and picturesque setting. A newer workshop sits out back - perfect for hobbies, storage, or projects. Major update includes a 2025 metal roof. Crawlspace inspection has identified needed repairs to

  

  Carmen Mansfield

  McClellan Realty, LLC

  167 Phelps Rd, Lamont, FL 32336
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  /42

  $519,000

  $31K PRICE DROP

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

  121 Shumard Ct, Monticello, FL 32344

  Beautiful, like-new 2022 farmhouse-style home located in the sought after Crooked Creek area. This spacious 2134 sq ft home features 4 bedrooms and 2.5 baths on a generous .85 acre lot, ideally situated on a quiet cul-de-sac on the west side of Monticello. The open-concept layout offers elegant coffered ceilings crown molding and a cozy gas fireplace with built-in shelving in the living room-

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  121 Shumard Ct, Monticello, FL 32344
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  /41

  $499,000

  $51K PRICE DROP

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

  398 Tecumseh Rd, Monticello, FL 32344

  Charming Cape Cod-style home tucked away on 5 acres just minutes to downtown Monticello. This one owner home has been lovingly maintained and reflects years of care and pride of ownership. With over 2200 square feet of living space, the home offers a comfortable layout. The main floor features three bedrooms, one bath, a welcoming living room with a gas fireplace, dining area, kitchen and a

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  398 Tecumseh Rd, Monticello, FL 32344
• 

  

  /5

  $199,000

  • Land
  • 5.03 Acres
  • $39,563 per Acre

  TBD W Washington, Monticello, FL 32344

  Fronting on Hwy-90 this high elevation lot is lightly wooded. Some restrictions apply.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD W Washington, Monticello, FL 32344
• 

  

  /10

  $253,080

  • Land
  • 21.09 Acres
  • $12,000 per Acre

  tbd Gamble Rd, Monticello, FL 32344

  Nature at its best, 21 acres of virgin forest with massive pines and a variety of hardwoods including a mixture of oaks, magnolias and hickory. Beautiful natural setting of rolling land with trails that meander through the property with an abundance of wildlife. Just up the road from the Wacissa River. The second parcel ID is 22-1S-3W-0000-0023-0000. ADJOINING HOME AND 20 ACRES AVAIABLE FOR

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  tbd Gamble Rd, Monticello, FL 32344
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  /6

  $50,000

  • Land
  • 26,571 Sq Ft
  • $81,967 per Acre

  790 Rd, Lamont, FL 32336

  Beautiful building lot, ideal for home or mobile home. Existing doublewide on the property in poor condition. Do not enter mobile home due to condition. The home may be repairable for the right buyer, roof has been leaking so it will be a major repair.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  790 Rd, Lamont, FL 32336
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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

  4589 Ashville Hwy, Monticello, FL 32344
• 

  

  /16

  $495,000

  $54K PRICE DROP

  • 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

  640 Nautilus Dr, Monticello, FL 32344
• 

  

  /57

  $699,000

  • 6 Beds
  • 3.5 Baths
  • 3,114 Sq Ft

  365 S Mulberry St, Monticello, FL 32344

  Historic soul. Modern substance. A rare circa-late 1800s home, beautifully restored and thoughtfully made NEW. Some houses simply endure... and some are given the rare chance to begin again. Better than New Construction! Just two blocks from the courthouse square in Monticello, Fl, this circa-late 1800s home—a classic Southern I-house shaped by Greek Revival influence—once stood quietly

  Lee Hall Capital City Real Estate Group

  365 S Mulberry St, Monticello, FL 32344
• 

  

  /19

  $281,800

  $68K PRICE DROP

  • Land
  • 70.45 Acres
  • $4,000 per Acre

  265 Neely Rd, Monticello, FL 32344

  Secluded, but not remote, this 70.45 acre tract in eastern Jefferson County, Florida would make an ideal hunting getaway property or a rural homesite. Virtually no ambient noise or light that will disturb the quiet woods. About half the tract is in 7-year-old planted loblolly pines and the rest is in natural woods and cypress ponds. You will be smack in the middle of some of the best deer and

  Dave Lewis Southern Forestry Realty

  265 Neely Rd, Monticello, FL 32344
• 

  

  /16

  $487,878

  $220K PRICE DROP

  • Land
  • 122 Acres
  • $3,999 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
• 

  

  /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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