Jefferson County FL Homes for Sale

• 

  

  

  /12

  $74,999

  • 3 Beds
  • 2 Baths

  11 N Back Ct, Monticello, FL 32344

  Fall into Savings when you take advantage of our limited-time special offer! Purchase this home and receive 4 months FREE site rent plus pay NO application fees. Hurry! Offer expires September 30, 2026. Act fast! Restrictions apply. Discover the brand-new Cornerstone 72, offering 1,152 square feet of thoughtfully designed living space with modern style and everyday comfort. The open-concept

  Patty Davis Jefferson Pines

  11 N Back Ct, Monticello, FL 32344
• 

  

  

  /35

  $3,300,000

  • Land
  • 8.01 Acres
  • $411,985 per Acre

  1410 Malloy Landing Rd, Monticello, FL 32344

  An exceptionally rare opportunity to acquire 8+ acres with 630 ft of riverfront property on the crystal-clear, spring-fed Wacissa River in Jefferson County, FL. Bordering it's own tributary called Little River just off of the main river channel between the head of the river and the "Big Blue" Spring, this extraordinary property offers a level of privacy, exclusivity, and natural beauty rarely

  Natalie Goley All Realty Services

  1410 Malloy Landing Rd, Monticello, FL 32344
• 

  

  

  /70

  $895,000

  • 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
• 

  

  

  /12

  $76,999

  • 3 Beds
  • 2 Baths

  7 N Front Ct, Monticello, FL 32344

  Fall into Savings when you take advantage of our limited-time special offer! Purchase this home and receive 4 months FREE site rent plus pay NO application fees. Hurry! Offer expires September 30, 2026. Act fast! Restrictions apply. Welcome home to the Cornerstone 76 by Clayton, a brand-new 3-bedroom, 2-bathroom home offering 1,152 square feet of comfortable, modern living space. Designed with an

  Patty Davis Jefferson Pines

  7 N Front Ct, Monticello, FL 32344
• 

  

  

  /23

  $357,000

  $98K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,326 Sq Ft

  535 Holly Rd, Monticello, FL 32344

  Wonderful Cottage Home in Quaint Crooked Creek Subdivision in Monticello Florida. Open Floor Plan with 3 Beds/2 Baths. Tiled Covered Front Porch with a Large Tiled Screened Porch and Deck for Grilling. There is a Built in Storage Shed approx. 4x7. Spacious Garage with Shelves. Additional 30Amp for RV with Parking Space Designed for RV or could be used for Additional Parking. Landscape is

  Susan Coker Advantage Premier Realty LLC

  535 Holly Rd, Monticello, FL 32344
• 

  /2

  $360,500

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft

  1605 Sweetbay Ct, Monticello, FL 32344

  Construction has begun. Completion date should be approx 4 months or less. We will update the comments as the construction progresses. Picture is virtual. More to come as construction continues. Propane appliances and Rinnai Tankless Water Heater.

  Steve Walker Steve C. Walker Realty, LLC

  1605 Sweetbay Ct, Monticello, FL 32344
• 

  

  /19

  $249,000

  • 3 Beds
  • 2 Baths
  • 1,210 Sq Ft

  30 Pine Needle Trace, Monticello, FL 32344

  Discover this charming 3-bedroom, 2-bath home, ideally located just off Mahan Road and conveniently close to Downtown Monticello. Featuring a vaulted living room and cozy gas fireplace, this residence offers a welcoming and spacious atmosphere. The large fenced-in yard is perfect for pets and outdoor gatherings. The master suite is generously sized for comfort. Additional highlights include a

  Caleb Stephens Silo Hill Properties

  30 Pine Needle Trace, Monticello, FL 32344
• 

  

  /31

  $599,900

  $25K PRICE DROP

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

  140 Shumard Ct, Monticello, FL 32344

  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 Attached 2-car garage Just

  Caleb Stephens Silo Hill Properties

  140 Shumard Ct, Monticello, FL 32344
• 

  /2

  $59,500

  $20K PRICE DROP

  • Land
  • 19,602 Sq Ft
  • $132,222 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
• 

  

  /14

  $115,000

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  1420 Tennessee Ave, Monticello, FL 32344

  Calling all investors, house-flippers, and handy homewoners! Fix & Flip for cash or hold for rental income. Located just 3 minutes from downtown Monticello and 30 minutes to Tallahassee. This 1968 two-story home is built on concrete blocks (1st story), & sits on a large 0.38-acre lot with mature vegetation for privacy on 2 sides. Has a metal roof (unknown age), HVAC~ 2020. Utilities are on for

  Cindy Teem Armor Realty, Inc

  1420 Tennessee Ave, Monticello, FL 32344
• 

  

  /10

  $60,000

  • Land
  • 5.07 Acres
  • $11,834 per Acre

  Vacant E Duckpond Dr, Greenville, FL 32331

  Five acres of freedom. Tucked back and surrounded by oaks, magnolias, and other native vegetation, this property offers privacy, usable land, and plenty of room to explore. The property is high and dry, with areas clear enough to easily walk and enjoy. No HOA and high-speed internet available at the road. Native beautyberries, wild grapes, chanterelles, and other seasonal finds make it

  Alexandria Marinelli All Realty Services

  Vacant E Duckpond Dr, Greenville, FL 32331
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  /7

  $41,000

  • Land
  • 1.19 Acres
  • $34,454 per Acre

  XX Quail Ln, Monticello, FL 32344

  1.19 acre lot off of paved road in Lloyd Acres. Partially cleared. High elevation. Mobile homes are allowed. An additional 2.12 acres available for purchase.

  Callie Rhoads The Naumann Group Real Estate

  XX Quail Ln, Monticello, FL 32344
• 

  

  /18

  $254,900

  New Construction

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

  360 Bowman St, Monticello, FL 32344

  New construction; very convenient to downtown; house is close to completion.

  Steve Walker Steve C. Walker Realty, LLC

  360 Bowman St, Monticello, FL 32344
• 

  /2

  $59,500

  $20K PRICE DROP

  • Land
  • 19,602 Sq Ft
  • $132,222 per Acre

  Lot 13 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 13 & 22 directly behind it totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 13 E Washington St, Monticello, FL 32344
• 

  

  /31

  $259,900

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  1164 Oaklands Plantation Rd, Monticello, FL 32344

  Nestled on 5.5 peaceful, private acres, this charming 3-bedroom, 2-bath home offers the perfect blend of space, comfort, and tranquility. Step inside to an open floor plan designed for both everyday living and effortless entertaining, with a seamless flow between the living, dining, and kitchen areas. The spacious primary suite is a true retreat, featuring a large en-suite bathroom complete with

  Norris Bishop Norris Bishop Realty, LLC

  1164 Oaklands Plantation Rd, Monticello, FL 32344
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  /24

  $175,000

  • 3 Beds
  • 2 Baths
  • 1,825 Sq Ft

  520 E High St, Monticello, FL 32344

  AFFORDABLE OLD MONTICELLO (FL) HOME. Spacious, good condition, move-in-ready. Convenient, easy walk to charming downtown. Recent basic repairs and renovations (roofing, electrical, plumbing, etc). Old but very livable, with a flexible floor plan. Four possible bedrooms, two baths. Recent central heat and air. Large deck equipped with a hot tub (unknown condition) and fenced. Handicap ramp. Huge

  Hines Boyd FL-GA Realty & Auction

  520 E High St, Monticello, FL 32344
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  /11

  $45,000

  $5K PRICE DROP

  • Land
  • 5.01 Acres
  • $8,982 per Acre

  TBD Aucilla Plantation Ct, Greenville, FL 32331

  5.01 wooded acres, well known for the large amount of Indian Artifacts due to the nearby Aucilla River, beautiful native trees, close to Smokehouse boat landing, Aucilla Shores Subdivision contains a private airstrip, animal Friendly & only a couple miles off Ashville Highway on well maintained roads.

  Justin Peel Maclay Realty & Management LLC

  TBD Aucilla Plantation Ct, Greenville, FL 32331
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  /26

  $69,000

  • Land
  • 5 Acres
  • $13,800 per Acre

  vacant E 2nd Way, Greenville, FL 32331

  Located just off Ashville Highway, this 5-acre homesite offers the kind of North Florida setting buyers search for but rarely find. Tucked along a quiet road with minimal traffic, the property provides peace, privacy, and room to create the lifestyle you’ve been wanting. Scattered with beautiful mature oak trees, the land has character, shade, and a timeless natural feel that is hard to

  Hunter Key OaksFeather Realty

  vacant E 2nd Way, Greenville, FL 32331
• 

  

  /70

  $470,000

  $34K PRICE INCREASE

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

  78 Fen Ct, Monticello, FL 32344

  Photos of previous homes. Come choose all your finishes and upgrades. Home is just finishings the framing stage of construction. Amazing new construction 3 bedroom 2 bathroom by Nailed It Tallahassee LLC. Luxurious master suite, Kitchen made of dreams, this is a must see!

  Amber McKinney Hamilton Realty Advisors LLC

  78 Fen Ct, Monticello, FL 32344
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  /12

  $399,000

  • Land
  • 60 Acres
  • $6,650 per Acre

  0 Fallow Rd Unit 373902, Lamont, FL 32336

  Private recreational tract located in western Jefferson County surrounded by very large managed private tracts. The quality of game rivals the best low fence hunting Florida has to offer. White tailed deer, wild turkey, ducks and bears. Owners have seen no sign of wild hogs. The 60 acres has good access off Fallow Road with building sites on both sides of the road. The majority of the acreage is

  Monroe Rogers Landcorp, Inc.

  0 Fallow Rd Unit 373902, Lamont, FL 32336
• 

  

  /4

  $299,000

  • Land
  • 85.69 Acres
  • $3,489 per Acre

  0 Big Joe Rd Unit 399642, Monticello, FL 32344

  85.69 acres of land located on Big Joe Road in Monticello. Zoned Agri-05, this versatile property offers a unique blend of privacy, natural beauty, and development potential. Featuring a mix of wetlands and usable upland areas, the property may be ideal for a variety of uses including recreational development, camping, hunting retreat, RV park, event venue, outdoor hospitality concepts, or future

  Lynnaye Boyd Resilience Realty

  0 Big Joe Rd Unit 399642, Monticello, FL 32344
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  /50

  $108,000

  $12K PRICE DROP

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

  1150 Sage St, Monticello, FL 32344

  Investor special! Cash only!

  Matthew Soltis Robert Slack LLC

  1150 Sage St, Monticello, FL 32344
• 

  

  /13

  $90,000

  • Land
  • 2.12 Acres
  • $42,453 per Acre

  1264 Quail Ln, Monticello, FL 32344

  Looking for a place where you can spread out, bring a mobile home, build a workshop, raise chickens, plant a garden, and create your own little slice of country life? This 2.12-acre property in Lloyd Acres gives you the space and flexibility to make it happen. Located just off a paved road and sitting at a high elevation, this property already has some of the hard work done. Power, well, and

  Callie Rhoads The Naumann Group Real Estate

  1264 Quail Ln, Monticello, FL 32344
• 

  /2

  $95,000

  • Land
  • 2.22 Acres
  • $42,793 per Acre

  450 Oconee Ln, Monticello, FL 32344

  Vacant building lot; inside the city limits, city water and sewer are available, all high and dry; very nice neighborhood, no HOA.

  Steve Walker Steve C. Walker Realty, LLC

  450 Oconee Ln, Monticello, FL 32344
• 

  

  /12

  $149,900

  $35K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,312 Sq Ft

  670 Poplar St, Monticello, FL 32344

  Solid 3/1 SFR brick less than a mile from downtown Monticello! This quaint 1,312 sq ft home sits under a metal roof and only requires your vision and a little TLC to become a superb starter home or investment opportunity. It also includes an additional lot.

  Spencer Conner Keller Williams Town & Country

  670 Poplar St, Monticello, FL 32344
• 

  /2

  $49,500

  $20K PRICE DROP

  • Land
  • 19,602 Sq Ft
  • $110,000 per Acre

  Lot 14 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 14 & 21 directly behind it totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 14 E Washington St, Monticello, FL 32344
• 

  

  /21

  $60,000

  • Land
  • 2.2 Acres
  • $27,273 per Acre

  000 Walker Springs Rd, Monticello, FL 32344

  Experience the peace and natural beauty of North Florida on this attractive 2.2 acre lot located on Walker Springs Road. The property features mature oak trees and long leaf pines and a quiet setting overlooking the Cody Escarpment. Beautiful open pastures adjoin the rear of the property, along with a picturesque pond where deer, turkey, and other wildlife regularly come to water. With abundant

  Alicia Radtke All Realty Services

  000 Walker Springs Rd, Monticello, FL 32344
• 

  

  /7

  $150,000

  $48K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,366 Sq Ft

  870 Shady Ln, Monticello, FL 32344

  Welcome to 870 Shady Lane in Monticello, Florida—a charming property that offers the perfect blend of privacy, space, and small-town appeal. Nestled on a quiet, tree-lined street, this home provides a peaceful retreat while still being conveniently close to the historic downtown district, local shops, and dining. Surrounded by mature trees and natural beauty, the property offers a serene setting

  Angela Graham Hamilton Realty Advisors LLC

  870 Shady Ln, Monticello, FL 32344
• 

  

  /68

  $695,000

  • 5 Beds
  • 3 Baths
  • 3,536 Sq Ft

  2247 Waukeenah Hwy, Monticello, FL 32344

  Just 3 miles south of Monticello, FL and only 2.5 miles from I-10, this 10.45 acre working homestead has been thoughtfully set up for country living, livestock and extended family. The 3,536 sq. ft. home features 4 bedrooms/2 baths in the main house (with the set up for an additional bath upstairs) master is conveniently located downstairs with two walk-in closets, private access, plenty of

  Alicia Radtke All Realty Services

  2247 Waukeenah Hwy, Monticello, FL 32344
• 

  

  /3

  $19,500

  • Land
  • 37,461 Sq Ft
  • $22,674 per Acre

  0 Cox Rd Unit 400763, Monticello, FL 32344

  0.84-Acre Monticello Lot on Cox Rd – SURVEY & ELEVATION LETTER ALREADY COMPLETED! Excellent opportunity to own a peaceful 0.84-acre parcel (Lots 89 & 90 of Springdale Pecan Plantation) located on Cox Road in beautiful Jefferson County. Surrounded by natural North Florida beauty, this lot offers rural tranquility while keeping you just minutes from historic downtown Monticello and 25-30 minutes to

  Stephen Hachey Flat Fee MLS Realty

  0 Cox Rd Unit 400763, Monticello, FL 32344
• 

  

  /19

  $325,000

  $174K PRICE DROP

  • Land
  • 3.2 Acres
  • $101,562 per Acre

  XX Shiver Rd, Monticello, FL 32345

  Beautiful High lot at corner of Hwy 19, Shiver and Lake Rd. This listing is compilation of 3 contiguous parcels : (19-2N-5E-0140-0000-0300 and 19-2N-5E-0000-0210-0000 and 19-2N-5E-0140-0000-0170). for a total of 3.25 acres . PRIME location for multi-family, office, mixed use commercial business that needs visibility and ease of access. Utilities available- Water access to main line is Under Hwy

  Jennifer Ward Century 21 First Story

  XX Shiver Rd, Monticello, FL 32345
• 

  

  /11

  $80,999

  • 4 Beds
  • 2 Baths

  4 Franks Ct, Monticello, FL 32344

  Fall into Savings when you take advantage of our limited-time special offer! Purchase this home and receive 4 months FREE site rent plus pay NO application fees. Hurry! Offer expires September 30, 2026. Act fast! Restrictions apply. Step into the brand-new Blazer 76 4A by Clayton, a beautifully designed 4-bedroom, 2-bath home offering 1,216 square feet of comfortable, modern living. The bright,

  Patty Davis Jefferson Pines

  4 Franks Ct, Monticello, FL 32344
• 

  

  /10

  $79,999

  • 3 Beds
  • 2 Baths

  11 N Front Ct, Monticello, FL 32344

  Fall into Savings when you take advantage of our limited-time special offer! Purchase this home and receive 4 months FREE site rent plus pay NO application fees. Hurry! Offer expires September 30, 2026. Act fast! Restrictions apply. Discover the brand-new Blazer 76 F by Clayton, a beautifully designed 3-bedroom, 2-bath home offering 1,216 square feet of modern comfort. The spacious kitchen

  Patty Davis Jefferson Pines

  11 N Front Ct, Monticello, FL 32344
• 

  

  /37

  $429,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  107 Tarn Way, Monticello, FL 32344

  Experience a nearly new construction with this stunning 3-bedroom, 2-bathroom home crafted by Nailed It Tallahassee LLC. Featuring a luxurious master suite and a dream kitchen, this property is a must-see. It includes plantation shutters and remote-controlled blinds throughout. Enjoy the privacy of a fenced-in backyard. Move-in ready!

  Amber McKinney Hamilton Realty Advisors LLC

  107 Tarn Way, Monticello, FL 32344
• 

  

  /7

  $660,000

  • Land
  • 44.32 Acres
  • $14,892 per Acre

  XXX Steen Rd, Monticello, FL 32344

  The opportunity to own a pristine 44+ acre tract of raw land just on the outskirts of charming Monticello is now available. This largely untouched property offers a peaceful country setting with rolling farmland and classic North Florida character, making it an ideal location for your future home or recreational retreat. Situated with road frontage on Steen Road, this buildable tract is covered

  Caleb Stephens Silo Hill Properties

  XXX Steen Rd, Monticello, FL 32344
• 

  /2

  $85,000

  • Land
  • 19,602 Sq Ft
  • $188,889 per Acre

  Lot 11 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 11 & 24 directly behind it totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 11 E Washington St, Monticello, FL 32344
• 

  

  /11

  $78,999

  • 3 Beds
  • 2 Baths

  8 N Front Ct, Monticello, FL 32344

  Fall into Savings when you take advantage of our limited-time special offer! Purchase this home and receive 4 months FREE site rent plus pay NO application fees. Hurry! Offer expires September 30, 2026. Act fast! Restrictions apply. Discover the brand-new Foothills 76 by Clayton, a beautifully designed 3-bedroom, 2-bath home offering 1,216 square feet of stylish and comfortable living space. The

  Patty Davis Jefferson Pines

  8 N Front Ct, Monticello, FL 32344
• 

  /2

  $59,500

  $26K PRICE DROP

  • Land
  • 2.05 Acres
  • $29,024 per Acre

  Lot 25 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 10 Lots- 25-35 (Survey) totaling 2.05 Acres.

  Liz Kuntz Keller Williams Town & Country

  Lot 25 E Washington St, Monticello, FL 32344
• 

  

  /11

  $144,900

  • Land
  • 10.5 Acres
  • $13,800 per Acre

  XXX Vista Rd, Monticello, FL 32344

  Beautiful live oaks, pines and other mature landscape on this 10.5 acres in quaint Monticello. 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

  Jacquelynn Harrison-Cofty Advantage Premier Realty LLC

  XXX Vista Rd, Monticello, FL 32344
• 

  

  /11

  $80,999

  • 4 Beds
  • 2 Baths

  2 N Front Ct, Monticello, FL 32344

  Fall into Savings when you take advantage of our limited-time special offer! Purchase this home and receive 4 months FREE site rent plus pay NO application fees. Hurry! Offer expires September 30, 2026. Act fast! Restrictions apply. Step into the brand-new Blazer 76 4A by Clayton, a beautifully designed 4-bedroom, 2-bath home offering 1,216 square feet of comfortable, modern living. The bright,

  Patty Davis Jefferson Pines

  2 N Front Ct, Monticello, FL 32344

Showing Results 41 - 80, Page 2 of 3