Homes for Sale in 32344

• 

  

  

  /31

  $285,000

  • 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

  Cole Davis The Naumann Group Real Estate

  1164 Oaklands Plantation Rd, Monticello, FL 32344
• 

  

  

  /17

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,502 Sq Ft

  406 Robin Rd, Monticello, FL 32344

  This charming 3-bedroom, 2-bath residence offers spacious living with vaulted ceilings, all nestled on five acres of private land. The property features a new roof for peace of mind, and the large deck is perfect for outdoor entertaining.This home also has a large unfinished basement to fit many of needs. The acreage is divided into 4 lots, providing plenty of space and potential. Located on a

  406 Robin Rd, Monticello, FL 32344
• 

  

  

  /57

  $549,000

  • 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

  515 E Palmer Mill Rd, Monticello, FL 32344
• 

  

  

  /17

  $242,000

  • 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.

  1160 E Washington St, Monticello, FL 32344
• 

  

  

  /4

  $299,000

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

  0 Big Joe Rd Unit 399642, Monticello, FL 32344

  Exceptional opportunity to own 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

  Lynnaye Boyd Resilience Realty

  0 Big Joe Rd Unit 399642, Monticello, FL 32344
• 

  

  /6

  $462,000

  • Land
  • 58.46 Acres
  • $7,903 per Acre

  1310 Piney Woods Rd, Monticello, FL 32344

  No sign on property, Must be accompanied. Nature and tree lover, timber value on the property, many great homesite locations. Pines and hardwoods, Power easement on the property. Community water and high speed internet through Tri County Electric. 3 separate parcel ID 3#s 03-1N-4E-0000-001F-0000, 03-1-4E-0000-001E-0000

  1310 Piney Woods Rd, Monticello, FL 32344
• 

  

  /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

  305 Old Lloyd Rd, Monticello, FL 32344
• 

  

  /45

  $789,000

  • 4 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  900 Ridge Rd, Monticello, FL 32344

  Tucked just outside of historic Monticello, this exceptional 11+ acre property offers a refined rural lifestyle without sacrificing everyday convenience. This Jefferson County gem features a much sought after combination of home, acreage, pool, barn and location. The residence itself is over 2300 square feet and is filled with natural light throughout. The open floor plan is perfect for

  900 Ridge Rd, Monticello, FL 32344
• 

  

  /8

  $25,000

  • Land
  • 14,374 Sq Ft
  • $75,758 per Acre

  923 King St, Monticello, FL 32344

  Exceptional cleared corner lot with a concrete slab already in place—ready for your vision! City water and sewer connections are available, with electric at the road. Conveniently located just minutes from downtown Monticello. Motivated Sellers!

  Alicia Radtke All Realty Services

  923 King St, Monticello, FL 32344
• 

  

  /12

  $185,000

  • 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
• 

  

  /12

  $165,000

  • 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

  5936 Vista Rd, Monticello, FL 32344
• 

  

  /6

  $20,999

  • 2 Beds
  • 2 Baths

  10 S Front Ct, Monticello, FL 32344

  TAKE ADVANTAGE OF OUR MEMORIAL DAY MEGA MOVE-IN EVENT! If you purchase this home, receive 2 months FREE site rent and NO application fees. Offer expires May 31, 2026. Act fast! Restrictions apply. A beautifully refurbished home is coming soon-and it's definitely one to keep an eye on. Renovations are currently underway with an estimated completion date of 5/31 (subject to change), bringing fresh

  Patty Davis Jefferson Pines

  10 S Front Ct, 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

  221 Kiley Dr, Monticello, FL 32344
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  /4

  $550,000

  • 6,024 Sq Ft

  535 Hagan St, Monticello, FL 32344

  Rare Investor Opportunity: 7-Unit Residential Complex for Sale Don't miss this fantastic investment opportunity! This well-maintained 7-unit complex features: Six 3-bedroom, 1-bathroom units One 2-bedroom, 1-bathroom unit Walking distance to downtown – perfect for tenants seeking convenience Corner lot location with excellent visibility Designated parking spots for each unit 2023 Roof Whether

  535 Hagan St, Monticello, FL 32344
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  /9

  $198,000

  • 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
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  /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.

  1511 Spring Hollow Dr, Monticello, FL 32344
• 

  

  /12

  $128,900

  • Land
  • 6.86 Acres
  • $18,790 per Acre

  1407 S Jefferson St, Monticello, FL 32344

  This property presents a strong commercial opportunity along the highly visible Hwy 19 corridor. The property consists of approximately 6.8± acres of B-2 Highway Commercial land with over 400± feet of frontage on Highway 19, offering excellent exposure and accessibility in a growing retail and service trade area.The site includes an approved development plan; however, the only designated

  1407 S Jefferson St, 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.

  220 Eaton St, Monticello, FL 32344
• 

  

  /13

  $65,000

  • 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

  40 Westview Ln, Monticello, FL 32344
• 

  

  /19

  $395,000

  • 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

  XX Shiver Rd, Monticello, FL 32345
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  /33

  $999,900

  • 3 Beds
  • 2.5 Baths
  • 4,383 Sq Ft

  728 Turney Anderson Rd, Monticello, FL 32344

  A Timeless Treasure, built by Riley Palmer Construction in 2006, this exceptional home captures the warmth and character of an early-1900s Craftsman farmhouse. It is located on 5 beautiful acres with mature pecan trees in the front and pines in the back yard. A spacious wrap around front porch welcomes you and features reclaimed New Orleans style doors and classic architectural details. Inside,

  728 Turney Anderson Rd, Monticello, FL 32344
• 

  

  /29

  $79,900

  • Land
  • 6.4 Acres
  • $12,484 per Acre

  XXX Hopson Rd, Monticello, FL 32344

  Unique shaped parcel located in a serene rural area—perfect for building, recreation, or investment

  Shanna D'Attile Keller Williams Town & Country

  XXX Hopson Rd, 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

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

  

  /25

  $400,000

  • 4 Beds
  • 3 Baths
  • 2,870 Sq Ft

  49 Foggy Ln, Monticello, FL 32344

  Welcome to 49 Foggy Lane in Monticello, FL—an exceptional opportunity to own a spacious property with endless potential! This 2,870 sq ft home features 4 generously sized bedrooms and 3 full bathrooms, along with a dedicated office space—perfect for remote work or added flexibility. Enjoy cozy evenings by the wood-burning fireplace, creating a warm and inviting atmosphere throughout the home. The

  Cyndi Ritchey Tallahassee Board of REALTORS®

  49 Foggy Ln, Monticello, FL 32344
• 

  

  /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,

  64 Sanctuary Dr, 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

  167 Phelps Rd, Lamont, FL 32336
• 

  

  /11

  $60,000

  • Land
  • 2.36 Acres
  • $25,424 per Acre

  0 Central Rd Unit 381525, Midway, FL 32344

  2.36 acre wooded lot for sale located down a paved road with access to cable and internet services. Land is high and dry. No mobile homes allowed.

  Erica Stallings KILLEARN SALES CENTER,

  0 Central Rd Unit 381525, Midway, FL 32344
• 

  

  /41

  $550,000

  • 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

  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.

  TBD W Washington, Monticello, FL 32344
• 

  

  /18

  $174,900

  • 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

  Mackenzie Biehl Tapestry Senior Living

  34 W Hummingbird Ln, 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

  40 Westview Ln, 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

  4589 Ashville Hwy, Monticello, FL 32344
• 

  

  /16

  $549,000

  • 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

  640 Nautilus Dr, 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.

  TBD E Meadow Rd, Monticello, FL 32344
• 

  

  /4

  $75,000

  • 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.

  205 E Cherokee Ave, 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

  0 Mallard Ln Unit 394437, Monticello, FL 32344
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  /38

  $549,000 Open Sat 10AM - 5PM

  • 4 Beds
  • 2.5 Baths
  • 2,233 Sq Ft

  35 Tarn Way, Monticello, FL 32344

  2026 Nailed It Tallahassee Parade of Homes Entry! **Photos are of previous build home will have different finishes. Home will be move in ready May 20th. Amazing new construction 4 bedroom 3 bathroom. Luxurious master suite, Kitchen made of dreams, this is a must see!

  Amber McKinney Hamilton Realty Advisors LLC

  35 Tarn Way, Monticello, FL 32344

Showing Results 41 - 77, Page 2 of 2