Jefferson County FL Homes for Sale

• 

  

  /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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  /49

  $398,900

  $26K PRICE DROP

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

  1628 N Jefferson Hwy, Monticello, FL 32344

  For generations, this beautifully maintained, one-family owned brick home has been a place where holidays were celebrated, children were raised, and life's everyday moments became treasured memories. Today, with only one family member remaining, the home has simply become more space than one person needs. Rather than seeing it sit too quietly, she hopes to pass it on to another family who will

  

  Lynette Sirmon

  All Realty Services

  1628 N Jefferson Hwy, 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

  Coldwell Banker Hartung

  701 Barber Hill, Lamont, FL 32336
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  /36

  $279,000

  • 3 Beds
  • 1.5 Baths
  • 1,880 Sq Ft

  380 N Jefferson St, Monticello, FL 32344

  Step into the timeless charm of historic downtown Monticello, Florida, with this unique property offering nearly 2000 square feet of character and endless potential. Located within walking distance of downtown shopping, dining, and community events, this property is perfectly suited for residential living, commercial use, or a combination of both. Featuring beautiful original wood floors, soaring

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  380 N Jefferson St, 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

  $2,735,850

  $50K PRICE DROP

  • 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
• 

  /2

  $199,000

  • Land
  • 5.85 Acres
  • $34,017 per Acre

  TBD Old Tung Grove Rd, Monticello, FL 32344

  Wooded 5.85 acre homesite. Convenient to Tallahassee. Access road has not been cleared yet to access this parcel.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD Old Tung Grove Rd, Monticello, FL 32344
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  /48

  $254,000

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

  490 N Cherry Ct, Monticello, FL 32344

  This is the kind of home you can move into and simply enjoy. Located in Cherry Street Square, a desirable community in the heart of historic Monticello, this immaculate two-bedroom, two-bath townhome with a bonus room or office has been thoughtfully updated from top to bottom. The interior feels fresh, bright and completely move-in ready, with luxury vinyl plank flooring, updated doors and

  

  Lindsey Sadler

  OaksFeather Realty

  490 N Cherry Ct, Monticello, FL 32344
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  /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
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  /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 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 cattle,

  

  Ben Jones

  Mossy Oak Properties Southern Land and Homes, LLC

  Vacant N Salt Rd, Monticello, FL 32344
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  /50

  $510,000

  $40K PRICE DROP

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

  121 Shumard Ct, Monticello, FL 32344

  Exceptionally maintained , this turn key 2022 farmhouse-style home is located in the sought after Crooked Creek area.Seller is motivated! This home is ready for immediate occupancy and includes whole house generator still under warranty. 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

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  121 Shumard Ct, Monticello, FL 32344
• 

  /2

  $139,000

  • Land
  • 5 Acres
  • $27,800 per Acre

  TBD Orchard Ln, Monticello, FL 32344

  Great Location in Western Jefferson County offering country living with the convenience of Tallahassee only minutes away. Wooded 5 acres on private lane. Restricted for site built homes with minimum of 1200 sq ft heated and cooled. Adjoining 5 available for sale.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD Orchard Ln, 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
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  /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
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  /36

  $584,000

  • 3 Beds
  • 3.5 Baths
  • 2,148 Sq Ft

  8250 Waukeenah Hwy, Monticello, FL 32344

  Enjoy two private year around spring fed ponds! Escape to your own private sanctuary on 30 breathtaking acres where nature, privacy, and craftsmanship come together. This custom-built retreat features soaring vaulted ceilings, expansive windows, & French doors- blurring the line between indoors and out, flooding every room with natural light and serene views. 2 Bed, 2.5 Bath, thoughtfully

  

  Bhishma Benedict

  FLORIDA HOMES REALTY & MORTGAGE GVILLE

  8250 Waukeenah Hwy, Monticello, FL 32344
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  /46

  $325,000

  • 4 Beds
  • 2 Baths
  • 2,304 Sq Ft

  947 Piney Woods Rd, Monticello, FL 32344

  Charming 2022 Mobile Home on 5 Peaceful Acres A rare blend of modern comfort and wide-open space, this 2022 mobile home sits on 5+ acres—perfect for anyone craving privacy, freedom, and room to grow. Whether you dream of a hobby farm, a quiet country retreat, or simply a place with no close neighbors, this property delivers. Embrace freedom of country living with the convenience of a modern home.

  

  Brian Bachman

  Kelly & Kelly Properties, Inc

  947 Piney Woods 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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  /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
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  /2

  $50,000

  • Land
  • 2.5 Acres
  • $20,000 per Acre

  TBD E Meadow Rd, Monticello, FL 32344

  Wooded lot, pines and hardwoods. Mobile homes are allowed. High elevation.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD E Meadow Rd, Monticello, FL 32344
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  /32

  $1,805,000

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

  Vacant N Salt Rd, Monticello, FL 32344

  192± acre organic cattle farm located in beautiful Jefferson County, Florida Certified organic operation for 20+ years with a long-standing history of sustainable land stewardship Fully fenced and cross-fenced for efficient cattle rotation and livestock management Improved pastureland ideal for cattle, horses, or continued agricultural use Several picturesque homesites overlooking the scenic

  

  Ben Jones

  MOSSY OAK PROPERTIES

  Vacant N Salt Rd, Monticello, 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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  /55

  $899,000

  $20K PRICE DROP

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

  9901 Gamble Rd, Monticello, FL 32344

  PRIVATE 41-ACRE ESTATE MINUTES FROM TALLAHASSEE - TRAILS, WILDLIFE, PASTURE & CUSTOM HOME 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, offering endless possibilities for equestrian

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  9901 Gamble 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
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  /25

  $162,900

  $62K PRICE DROP

  • Land
  • 14.9 Acres
  • $10,933 per Acre

  96 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

  96 Sneads Dr, Greenville, FL 32331
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  /4

  $80,500

  $45K PRICE DROP

  • Land
  • 5.05 Acres
  • $15,941 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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  /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

  $1,950,000

  $50K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /11

  $45,000

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

  1 W Meadow Rd, Monticello, FL 32344

  All Offers considered..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
• 

  /2

  $125,000

  • Land
  • 5.96 Acres
  • $20,973 per Acre

  0 Eastwood Unit 402606, Monticello, FL 32344

  Back on the market - Discover the perfect place to build your dream home on this beautiful nearly 6-acre parcel! Enjoy the peace and privacy of country living with the convenience of being just minutes from the interstate and a short drive to Tallahassee. With plenty of room for your custom home, workshop, gardens, or recreational space, the possibilities are endless! Whether you’re looking to

  D. Scott Kilgore Superior Realty Group LLC

  0 Eastwood Unit 402606, Monticello, FL 32344
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  /24

  $298,900

  New Construction

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

  1070 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

  1070 Partridge Ln, 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
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  /70

  $185,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  304 Limestone Rd, Monticello, FL 32344

  Welcome to peaceful country living in the quiet community of Wacissa, Florida! Nestled on 3.38 beautiful acres, this 3-bedroom, 2-bathroom home offers the ideal opportunity for anyone dreaming of a hobby farm, homestead, or simply extra space to enjoy the outdoors. Designed with both comfort and functionality in mind, the 1,680-square-foot home features a desirable split floor plan, separating

  Dee Leslie OaksFeather Realty

  304 Limestone Rd, Monticello, FL 32344
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  /41

  $399,000

  • 5 Beds
  • 2 Baths
  • 2,184 Sq Ft

  10283 Ashville Hwy, Greenville, FL 32331

  Short Sale Potential! Dreaming of owning your own private farm with a large house AND Solar Powered? Look no further! Beautiful and serene 16 acres with fruit trees, fields, lots of horse potential and 40 solar panels about 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

  Lee Hall Bespoke Realty of Tallahassee

  10283 Ashville Hwy, Greenville, FL 32331
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  /70

  $915,000

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

  4216 W Washington Hwy, Monticello, FL 32344

  Tucked away on 10.87 private acres behind its own gated entrance in the sought-after Rainey Run community, this custom-built home offers the perfect balance of quality craftsmanship, modern comfort, and peaceful country living. Built by Hannon Construction in 2023, the 3-bedroom, 2.5-bath home spans 2,412 square feet and was thoughtfully designed with timeless finishes and functional spaces

  Savannah Stephens Hill Spooner & Elliott Inc

  4216 W Washington Hwy, Monticello, FL 32344
• 

  

  /31

  $677,500

  $53K PRICE INCREASE

  • 4 Beds
  • 3 Baths
  • 2,716 Sq Ft

  140 Shumard Ct, Monticello, FL 32344

  NOW INCLUDES ADDITIONAL LOT!! Discover this stunning 2,600+ sqft home built in 2021, offering the perfect blend of quiet country living and modern convenience. Adjoinging additional lot can also be purchased! Features include: 4 spacious bedrooms and 3 full bathrooms 2 master bedrooms located downstairs Dedicated office/bonus room – ideal for work or hobbies Modern kitchen and open living spaces

  Caleb Stephens Silo Hill Properties

  140 Shumard Ct, Monticello, FL 32344
• 

  /2

  $79,000

  • Land
  • 19,602 Sq Ft
  • $175,556 per Acre

  Lot 12 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes BOTH Lot 12 & 23 directly behind it totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 12 E Washington St, Monticello, FL 32344
• 

  

  /7

  $104,000

  $5K PRICE DROP

  • Land
  • 5 Acres
  • $20,800 per Acre

  130 Sweetfield Rd, Monticello, FL 32344

  Mobile-home-friendly property with a cleared homesite and an existing well, septic system, and electrical service already on the property. Seller financing is available. Conveniently located near I-10 and approximately 30 minutes from Tallahassee. Bring your home plans and enjoy a quiet country setting with room for animals, gardening, outdoor projects, and additional storage. Fence the property

  Moe Mossa Savvy Avenue, LLC

  130 Sweetfield Rd, Monticello, FL 32344
• 

  

  /19

  $65,000

  • Land
  • 1.75 Acres
  • $37,143 per Acre

  1602 Walker Springs Rd, Monticello, FL 32344

  Discover a rare opportunity to own 1.75 acres on Walker Springs Road, directly adjoining approximately 40,000-acres of the Aucilla Wildlife Management Area. Very few private parcels border this protected land, and this is currently the only adjoining property being offered on the market! Deer, turkey, and other wildlife are abundant and can often be seen right outside your back door. With the

  Alicia Radtke All Realty Services

  1602 Walker Springs Rd, Monticello, FL 32344

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