Jefferson County FL Homes for Sale

• 

  

  

  /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
• 

  

  

  /54

  $149,000

  • 2 Beds
  • 2 Baths
  • 1,792 Sq Ft

  12447 Gamble Rd, Monticello, FL 32344

  Corner Lot! This 2 bedroom (could be a 3rd Bdrm but most 1930's homes did not have closets), 2 bathroom home offers 1,792 sq ft of living on 1 acre in Wacissa, Florida, just 1 minute from the Wacissa River headwaters (first magnitude Spring) and boat launch in Monticello, Jefferson County, Florida. It’s an ideal spot for a hunting or fishing lodge or "Air B & B type of rental" specializing in

  

  Lynette Sirmon

  All Realty Services

  (448) 233-2927

  12447 Gamble Rd, Monticello, FL 32344
• 

  

  

  /44

  $595,000

  • 3 Beds
  • 2.5 Baths
  • 3,054 Sq Ft

  79 Lakeside Rd, Monticello, FL 32344

  Go Back in time in this traditional farmhouse nestled on 4.44 acres totally fence and cross fenced. Over 1110 sq ft of screened porch for entertaing, relaxing, or looking at the 20x30 Koi pond. Sparkling wood foors throughout create warmth to the spacious rooms. 9x32 central hallway, large living room, family room, and all bedrooms are oversized. 600 sq ft garage with loft and attached 1 car

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 230-7686

  79 Lakeside Rd, Monticello, FL 32344
• 

  

  

  /45

  $599,900

  • 3 Beds
  • 2.5 Baths
  • 2,546 Sq Ft

  181 Heritage Blvd, Monticello, FL 32344

  Certified Florida Green Home on 3 acres in the highly sough after Heritage Hills s/d. Enjoy the perfect blend of privacy and convenience with this Craftsman-style home, offering an easy commute to both Tallahassee and Monticello. The like-new residence boasts high-end finishes throughout, including crown molding, coffered ceilings, wainscoting, and a cozy gas fireplace. Relax or entertain

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 678-3070

  181 Heritage Blvd, Monticello, FL 32344
• 

  

  

  /25

  $198,000

  • Land
  • 14.9 Acres
  • $13,289 per Acre

  Lot 8 Sneads Dr, Greenville, FL 32331

  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 River". Outdoor enthusiasts

  

  Lynette Sirmon

  All Realty Services

  (448) 231-6582

  Lot 8 Sneads Dr, Greenville, FL 32331
• 

  

  /49

  $385,000

  • 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) 230-5161

  84 Lakeside Rd, Monticello, FL 32344
• 

  

  /43

  $295,000

  • 5 Beds
  • 2 Baths
  • 3,320 Sq Ft

  425 N Mulberry St, Monticello, FL 32344

  Charming 1920's Two-Story Home in the Heart of Downtown Monticello, Fl. Step back in time with this beautiful home nestled on a spacious 1/2 acre lot in the heart of Monticello. Bursting with character and potential, this property is perfect for those looking to restore a classic Southern gem. Inside, you will find original, wood ceiling, floors , and walls that are just waiting to be brought

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 222-3718

  425 N Mulberry St, Monticello, FL 32344
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  /37

  $365,000

  • 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

  (448) 236-0470

  205 N Rhodes St, Monticello, FL 32344
• 

  

  /12

  $93,500

  • Land
  • 5 Acres
  • $18,700 per Acre

  489 Ashville Highlands Dr, Greenville, FL 32331

  Come and camp while you are waiting to build. Many improvements on this 5 acre parcel. Partly cleared (approx 2.5 ac), large septic with comnection for RV with macerator pump, 200 amp power service with meter and pole and 30 amp RV connection. High speed internet running through the property. No HOA, freedom to build what you want. Enjoy an abundance of wildlife. Some area is in flood zone see

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 678-3158

  489 Ashville Highlands Dr, Greenville, FL 32331
• 

  

  /28

  $120,000

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  159 W Notre Dame St, Monticello, FL 32344

  A perfect redevelopment opportunity or your next home or investment property awaits! Lot could be subdivided into two lots. Enjoy peaceful country living just minutes from I-10 with this well-maintained 2-bedroom, 1-bath mobile home on a half acre in beautiful Lloyd, Florida. The home features about 600 square feet of cozy, efficient living space that’s been lovingly cared for and is move-in

  

  Raymond Seaman

  Dalton Wade, Inc

  (448) 200-2241

  159 W Notre Dame St, Monticello, FL 32344
• 

  

  /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

  (448) 233-5231

  TBD Rainey Run, Monticello, FL 32344
• 

  

  /59

  $585,000

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

  515 E Palmer Mill Rd, Monticello, FL 32344

  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, 2,000+ sq ft home has a kitchen flooded with natural

  

  Brenna Kelly-Ward

  Kelly & Kelly Properties, Inc

  (448) 334-5445

  515 E Palmer Mill Rd, Monticello, FL 32344
• 

  

  /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
• 

  

  /17

  $252,000

  • 3 Beds
  • 1 Bath
  • 1,334 Sq Ft

  1160 E Washington St, Monticello, FL 32344

  Remodeled brick home, 3 br 1 bath, open kitchen living room with fireplace. Large utility room with bonus room. Convenient Monticello location. Carport and privacy fenced back yard.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 231-4719

  1160 E Washington St, Monticello, FL 32344
• 

  

  /12

  $175,000

  • Land
  • 10.47 Acres
  • $16,714 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

  

  Jaquelynn Harrison-Cofty

  Property Finders Nguyen Realty

  (448) 334-6928

  5936 Vista Rd, Monticello, FL 32344
• 

  

  /67

  $425,000

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

  701 Barber Hill, Lamont, FL 32336

  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 storage

  

  Joann Jacobs

  Coldwell Banker Hartung

  (448) 218-0512

  701 Barber Hill, Lamont, FL 32336
• 

  

  /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
• 

  

  /4

  $60,000

  • Land
  • 0.43 Acre
  • $139,535 per Acre

  tbd Jackson St, Monticello, FL 32344

  2 building lots in the heart of Monticello, quiet side street. Each lot is 50 ft wide by approx. 190 deep. The lots back up to Waukeenah Street.

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 334-6781

  tbd Jackson St, Monticello, FL 32344
• 

  

  /37

  $319,000

  • 3 Beds
  • 1.5 Baths
  • 1,855 Sq Ft

  950 E Pearl St, Monticello, FL 32344

  Charming 1955 Cottage in the Heart of Monticello,Fl. Welcome home to this cozy yet surprisingly spacious 3-bedroom 1.5 -bath cottage on beautiful Oak Lined Pearl Street. Just a short walk or golf cart ride to historic downtown Monticello. Features include original hardwood floors, new windows, updated electrical and a sunroom with brick paver flooring- perfect for relaxing with morning coffee.

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 333-2115

  950 E Pearl St, Monticello, FL 32344
• 

  

  /30

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft

  354 Pine Cone Dr, Monticello, FL 32344

  2024 construction, shows like brand new home on large .68 acre lot, wooded buffer adds privacy. Open floor plan, kitchen with granite tops, counter seating and dining overlooks living room. Split bedroom plan , large master suite, walk in shower. 2 car garage, back screen porch overlooking privacy fenced backyard.

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 334-5234

  354 Pine Cone Dr, Monticello, FL 32344
• 

  

  /32

  $525,000

  • 3 Beds
  • 3 Baths
  • 3,026 Sq Ft

  3827 N Jefferson St, Monticello, FL 32344

  Spacious Contemporary Home on 5 Acres with Pond, Minutes from Thomasville, Ga! Enjoy peaceful country living with modern comforts in this stunning 3 bedroom, 3 bathroom brick home on 5 beautiful acres with a private pond. With over 3,000 square feet of living space, this property offers room to spread out and features thoughtful touches throughout. Inside, you'll find a large den with cozy

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (850) 367-9518

  3827 N Jefferson St, Monticello, FL 32344
• 

  /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

  (448) 333-2923

  TBD E Meadow Rd, Monticello, FL 32344
• 

  

  /11

  $125,000

  • 4 Beds
  • 1 Bath
  • 1,325 Sq Ft

  820 Shady Ln, Monticello, FL 32344

  Investor opportunity! 4BR/1BA home in Monticello, FL with great potential. Spacious layout, ideal for renovation, rental, or flip. Convenient location near downtown. Sold as-is.

  Shanna D'Attile

  Keller Williams Town & Country

  (448) 288-6490

  820 Shady Ln, Monticello, FL 32344
• 

  

  /8

  $199,000

  • Land
  • 5.12 Acres
  • $38,867 per Acre

  3621 E Capps Hwy, Monticello, FL 32336

  Vacant land with highway frontage on US-27 S., in Lamont, FL, just 4 miles east of the US-19 S/US-27 intersection in Capps. Zoned AG-5 (1 home/5 acres) - various commercial uses are allowed within AG-5 zoning. Refer to the county's Comprehensive Plan for specifics. The Northeast portion of the property is in wetlands, and majority of the parcel is located in Flood Zone A, except for small portion

  

  Brenna Kelly-Ward

  Kelly & Kelly Properties, Inc

  (850) 779-4681

  3621 E Capps Hwy, Monticello, FL 32336
• 

  

  /69

  $555,000 New Construction

  • 4 Beds
  • 2 Baths
  • 1,945 Sq Ft

  64 Sanctuary Dr, Monticello, FL 32344

  Just WOW this beautiful new construction home, with top-of-the-line custom finishes. This home gives you all the luxury you are looking for - a primary suite with stunning tongue and groove wood tray ceilings, master bath with stand-alone soaking tub, walk-in shower, double vanity with quartz countertops, an oversized walk-in custom master closet with built-ins. As you approach the living area,

  

  Chance Shutes

  Keller Williams Town & Country

  (448) 305-5882

  64 Sanctuary Dr, Monticello, FL 32344
• 

  

  /42

  $725,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,365 Sq Ft

  81 Old Tung Grove Rd, Monticello, FL 32344

  New Construction move in ready. Sacious over 2300 sq fr. with upstairs bonus room with bath and closet, could be 4th bedroom. 5.38 acre lot. Top of the lines finishes. Convenient to Tallahassee 15 minute drive.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 334-6582

  81 Old Tung Grove Rd, Monticello, FL 32344
• 

  

  /50

  $449,900 New Construction

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

  107 Tarn Way, Monticello, FL 32344

  2024 Custom Built Home with Premium Upgrades in Hemings Pond Subdivision! Better than new - This 3 bedroom/2 Bathroom 2024-build by Nailed It Construction offers luxury vinyl plank floors throughout, upgraded light fixtures, premium countertops, and elegant bath finishes. Both bathrooms feature tastefully muted designer tile-work. Thoughtful owner upgrades include: custom wood plantation shutters

  

  Brenna Kelly-Ward

  Kelly & Kelly Properties, Inc

  (448) 428-7831

  107 Tarn Way, Monticello, FL 32344
• 

  

  /56

  $275,000

  • 2 Beds
  • 2 Baths
  • 1,672 Sq Ft

  660 N Jefferson St, Monticello, FL 32344

  This updated craftsman bungalow sits just minutes from historic downtown Monticello and all its shops, restaurants and small-town living activities. The big welcoming front porch maintains a great view of Jefferson street and opens inside to a light-filled living space – great for entertaining, with an easy flow to a fenced lawn perfect for pets and weekend gatherings. The split-bedroom plan

  David Wesolowski American Real Estate Agency, I

  660 N Jefferson St, Monticello, FL 32344
• 

  

  /19

  $299,000

  • Land
  • 70.45 Acres
  • $4,244 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

  • 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
• 

  

  /3

  $244,900

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft

  45 N Cherry St, Monticello, FL 32344

  New construction in the heart of Monticello's Historic District! This beautifully built 1,092 sq ft off-grade home offers modern finishes while fitting seamlessly into the character of the neighborhood. The open floor plan features luxury vinyl plank flooring throughout, a stylish kitchen and stainless steel appliances, and quality craftsmanship from top to bottom. Bathrooms are finished with

  Steve Walker Steve C. Walker Realty, LLC

  45 N Cherry St, Monticello, FL 32344
• 

  

  /38

  $419,000

  • 3 Beds
  • 3 Baths
  • 2,706 Sq Ft

  339 Silver Lake Rd, Monticello, FL 32344

  Gorgeous home on 5 acres mostly pasture. Open concept with vaulted ceilings; great entertainment/family home. Private setting; must see to believe.

  Steve Walker Steve C. Walker Realty, LLC

  339 Silver Lake Rd, Monticello, FL 32344
• 

  

  /20

  $570,000

  • Land
  • 71 Acres
  • $8,028 per Acre

  0 Aucilla Rd Unit 22696476, Monticello, FL 32344

  Located on Aucilla Rd in Monticello, FL, this versatile AG-5 property offers endless potential for residential, agricultural, and recreational use. The upland portion has been cleared, making it ideal for a homesite or multiple residences, with zoning allowing one unit per five acres and options for family transfers under county guidelines.For those looking to enjoy North Floridas natural

  Jeremiah Thompson Saunders Land

  0 Aucilla Rd Unit 22696476, Monticello, FL 32344
• 

  

  /18

  $1,100,000

  • Land
  • 200 Acres
  • $5,500 per Acre

  0 Gum Swamp, Greenville, FL 32331

  Millwood Timberland West is a balanced recreational asset located in the Ashville, FL region. The internal road system meanders through the ecologically diverse landscape of pine plantations, live oaks and forested wetlands. The uplands are planted in slash pine that are approximately 15 years old with pockets of oak hammock and natural ponds. The ecosystem provides exceptional habitat for

  Bryant Peace Saunders Real Estate

  0 Gum Swamp, Greenville, FL 32331
• 

  

  /8

  $450,000

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

  0 Big Joe Rd Unit 2025007616, 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.

  Florie Gage Cornerstone Coastal Properties

  0 Big Joe Rd Unit 2025007616, Monticello, FL 32344
• 

  

  /23

  $325,000

  • 5 Beds
  • 2 Baths
  • 2,659 Sq Ft

  2664 W Washington Hwy, Monticello, FL 32344

  FULLY RENOVATED SPACIOUS HOUSE, 1.3 acres, on picturesque US 90 near Monticello. This move-in-ready home in good condition is a 1950’s era brick ranch-style home with new plumbing, new electric, fresh paint, new roof, and a whole home generator. The main living area is 2,659 sf with a unique two levels. 5 bedrooms and 2 baths with plenty of character, including the "Captain's Room" with built-in

  Heather Boyd FL-GA Realty & Auction

  2664 W Washington Hwy, Monticello, FL 32344
• 

  

  /4

  $135,000

  • Land
  • 5 Acres
  • $27,000 per Acre

  276 E Blue Bird Rd, Monticello, FL 32344

  Beautiful home sight in a quiet neighborhood. Fence and have animals

  S.W. Ellis Blue Bird Homes & Lands

  276 E Blue Bird Rd, Monticello, FL 32344
• 

  

  /37

  $240,000

  • 3 Beds
  • 3 Baths
  • 1,617 Sq Ft

  43 Depot St, Lamont, FL 32336

  Welcome to 43 Depot Street — where charm meets modern comfort in the heart of Lamont, FL. Step onto the inviting front porch, where you can sip your morning coffee and watch the sunrise over a neatly landscaped yard. Inside, you'll be greeted by a bright, open layout with new flooring, abundant windows, and fresh finishes that bring warmth to every room. The fully remodeled kitchen is a

  Crystal Daviner Marzucco Real Estate LLC

  43 Depot St, Lamont, FL 32336
• 

  

  /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
• 

  

  /4

  $19,500

  • Land
  • 0.86 Acre
  • $22,674 per Acre

  0 Cox Rd Unit 392538, Monticello, FL 32344

  Beautiful wooded 0.86 of an acre for sale on a very quiet street just north of downtown Monticello. It is in Flood Zone A which means you can build on it. The lot allows for a site built or mobile home. Check with the local county building and coding department to confirm. There is a land survey and elevation letter from 2023 that you may request to see if interested.

  Stephen Hachey Flat Fee MLS Realty

  0 Cox Rd Unit 392538, Monticello, FL 32344

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