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Newest Homes for Sale in Monticello, FL

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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
  • /70

    $1,325,000

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

    221 Kiley Dr, Monticello, FL 32344

    Welcome to a rare North Florida estate just minutes from Tallahassee—where luxury, land, and lifestyle come together. 221 Kiley Road is situated on expansive acreage in Monticello, and this private retreat offers the perfect blend of seclusion and convenience, located just a short drive from the heart of Tallahassee. For buyers seeking space, privacy, and versatility without sacrificing proximity

    Wilda Sigler Keller Williams Town & Country

    221 Kiley Dr, Monticello, FL 32344
  • /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

    Agent Photo

    Barry Kelly

    Kelly & Kelly Properties, Inc

    (448) 222-3877

    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

    Agent Photo

    Pam Kelly

    Kelly & Kelly Properties, Inc

    (448) 231-9639

    640 Nautilus Dr, Monticello, FL 32344
  • /38

    $609,900

    New Construction $10K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 2,134 Sq Ft

    261 Hiawatha Farms S, Monticello, FL 32344

    Back on the Market! Out of town buyers financing fell through. Welcome to this stunning new construction masterpiece, meticulously designed and built by the esteemed Kasdorf Design & Build, 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

    Ross Kozloski Kozloski Realty, LLC

    261 Hiawatha Farms S, Monticello, FL 32344
  • /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

    Agent Photo

    Pam Hoveland

    Landcorp, Inc.

    (448) 288-3932

    490 N Cherry Ct, Monticello, FL 32344
  • /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
  • /13

    $65,000

    $5K PRICE DROP
    • 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
  • /2

    $40,000

    • Land
    • 2.3 Acres
    • $17,391 per Acre

    0 Mallard Ln Unit 394437, Monticello, FL 32344

    Escape to peace & privacy, and with this beautiful 2.30-acre homesite located in the Lloyd Acres / Mallard Lane area of Jefferson County. Whether you’re planning your next home, a weekend retreat, or a smart land investment, this property offers the perfect blend of rural living with convenient access to Monticello and Tallahassee. Enjoy the natural surroundings, abundant trees, and quiet country

    Hunter Bowden Keller Williams Town & Country

    0 Mallard Ln Unit 394437, Monticello, FL 32344
  • /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.

    Agent Photo

    Pam Kelly

    Kelly & Kelly Properties, Inc

    (448) 678-3650

    1511 Spring Hollow Dr, Monticello, FL 32344
  • /31

    $434,000

    $5K PRICE DROP
    • 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
  • /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.

    Agent Photo

    Barry Kelly

    Kelly & Kelly Properties, Inc

    (448) 678-2958

    TBD Rainey Run, Monticello, FL 32344
  • /57

    $549,000

    $36K PRICE DROP
    • 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

    Agent Photo

    Brenna Kelly-Ward

    Kelly & Kelly Properties, Inc

    (448) 233-4937

    515 E Palmer Mill Rd, 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
  • /52

    $425,000

    $24K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,188 Sq Ft

    930 E Pearl St, Monticello, FL 32344

    Built between 1890–1910, this Classic Revival home sits on 1.77 acres along one of Monticello’s most admired streets and offers timeless architecture with an opportunity to restore and make it your own. The two-story layout includes 4 bedrooms and 3 bathrooms, with a circular driveway framed by boxwoods leading to a wide front porch perfect for rocking chairs. Inside, two front parlors flank the

    Rachel Sparling All Realty Services

    930 E Pearl St, Monticello, FL 32344
  • /11

    $105,000

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

    40 Westview Ln, Monticello, FL 32344

    Being offered "AS IS" two separate 1 acre parcels combined 18-1N-4E-0108-000G-0030 & 18-1N-4E-0108-000G-0040 for a total of 2.01 acres. 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

    Alicia Radtke All Realty Services

    40 Westview Ln, Monticello, FL 32344
  • /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

    Agent Photo

    Jacquelynn Harrison-Cofty

    Advantage Premier Realty LLC

    (448) 233-5846

    5936 Vista Rd, Monticello, FL 32344
  • /19

    $299,000

    $51K PRICE DROP
    • 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
  • /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. .

    Agent Photo

    Barry Kelly

    Kelly & Kelly Properties, Inc

    (448) 327-3237

    TBD Scott Dr, Monticello, FL 32344
  • /28

    $397,000

    $23K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,373 Sq Ft

    1205 E Pearl St, Monticello, FL 32344

    Charming 1956 Mid-Century Home. Fully Renovated with Modern Touches. Welcome to this beautifully reimagined 1956 classic, where character meets contemporary luxury. Every inch of this home has been thoughtfully renovated, blending original charm with stylish, modern upgrades. Step inside to discover a bright, open-concept living space featuring new floors, recessed lighting, and large windows

    Agent Photo

    Brian Bachman

    Kelly & Kelly Properties, Inc

    (448) 327-5761

    1205 E Pearl St, Monticello, FL 32344
  • /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

    Agent Photo

    Pam Kelly

    Kelly & Kelly Properties, Inc

    (448) 994-2623

    205 N Rhodes 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

    Agent Photo

    Brenna Kelly-Ward

    Kelly & Kelly Properties, Inc

    (448) 208-8969

    00 Mallard Blue Jay Ln Unit 2/3, 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

    $174,900

    $100K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,553 Sq Ft

    34 W Hummingbird Ln, Monticello, FL 32344

    New beautiful LVP flooring on mother in law suite side of the property and wdo repair underneath the new flooring!! So many options with this property!! It boasts 2 separate living spaces joined by a common family room. One side of the home has 1 bed and 1 bath, it's own kitchen and living space. The other side of the home has 3 bedrooms, 2 bathrooms and the kitchen and living area. The family

    Susan Gillespie Lord & Stanley Realty, Inc.

    34 W Hummingbird Ln, Monticello, FL 32344
  • /19

    $395,000

    $104K PRICE DROP
    • Land
    • 3.2 Acres
    • $123,438 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
  • /4

    $75,000

    $16K PRICE INCREASE
    • Land
    • 12,632 Sq Ft
    • $258,621 per Acre

    205 E Cherokee Ave, Monticello, FL 32344

    Prime vacant cleared commercial lot in downtown Monticello. Zoned Commercial B-2 Business Highway. Located Steps from US 19 South Across street from Burger King and Dollar Tree. Next door to Oreilly's Auto parts. High Traffic area and Good visibility. Address is for GPS only. Acreage is subject to survey.

    Starbuck Rissman Steve C. Walker Realty, LLC

    205 E Cherokee Ave, Monticello, FL 32344

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