Homes for Sale in 32344

• 

  

  

  /56

  $305,000

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft

  395 Sunset Dr, Monticello, FL 32344

  Welcome home to this charming 3-bedroom, 2-bath property set on a spacious lot with a fully fenced backyard. Thoughtfully updated throughout, major improvements include a 2023 metal roof, new HVAC system, new windows, and a new electric on-demand water heater. The renovated kitchen features all new appliances and a clean, modern look. The second full bath is conveniently located just off the rear

  Catherine Hope All Realty Services

  395 Sunset Dr, Monticello, FL 32344
• 

  

  

  /67

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 4,762 Sq Ft

  974 Rainey Run, Monticello, FL 32344

  **Professional pictures coming soon** Experience luxury living in the prestigious gated community of Rainey Run. This is where privacy, nature, and convenience come together on 10 breathtaking acres. Surrounded by towering hardwoods and abundant wildlife, this remarkable property offers a convenient peaceful retreat. Built in 2020, this custom home showcases quality craftsmanship with a highly

  Renee Dawkins Dawkins Realty LLC

  974 Rainey Run, Monticello, FL 32344
• 

  

  

  /37

  $62,800

  • Land
  • 7.85 Acres
  • $8,000 per Acre

  XXX Neely Rd, Monticello, FL 32344

  The following parcels are included in the sale: 32-2N-6E-0000-0023-0000 & 32-2N-6E-0000-0024-0000 This beautiful, wooded property offers a diverse landscape that's ideal for recreation, hunting, or building your private retreat. Mature hardwoods and towering pines create a peaceful forest setting, while natural clearings provide excellent locations for a homesite, food plots, or camping. The

  Chris Cammarata CONSULTANTS TO HOMEBUI

  XXX Neely Rd, Monticello, FL 32344
• 

  

  /2

  $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 - should be ready in about 45 days.

  Steve Walker Steve C. Walker Realty, LLC

  360 Bowman St, Monticello, FL 32344
• 

  

  /2

  $350,500

  New Construction

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

  1565 Sweetbay Ct, Monticello, FL 32344

  This home is currently coming out of the permitting phase. New construction will start in the next week. 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.

  Steve Walker Steve C. Walker Realty, LLC

  1565 Sweetbay Ct, Monticello, FL 32344
• 

  

  /19

  $444,900

  New Construction

  • 4 Beds
  • 3 Baths
  • 1,798 Sq Ft

  855 S Waukeenah St, Monticello, FL 32344

  Stunning New Construction recently built by Southern Construction. Centrally located in downtown Monticello, with mature landscaping, and plenty of room for the family. This 4 bed and 3 bath home features vinyl plank flooring, granite countertops, walk in tile shower and tub in master, upgraded trim package, and stainless appliances. Nice large back porch with deck, over looking the large

  Jared Parramore Coastwise Realty

  855 S Waukeenah St, Monticello, FL 32344
• 

  

  /36

  $584,000

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

  8250 Waukeenah Hwy, Monticello, FL 32344

  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 designed floor plan. Expansive wood deck where morning

  

  Bhishma Benedict

  FLORIDA HOMES REALTY & MORTGAGE GVILLE

  8250 Waukeenah Hwy, Monticello, FL 32344
• 

  

  /37

  $269,900

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  60 Bob White Trail, Monticello, FL 32344

  Tucked behind a gated entrance and nestled on 5.54 acres, this property offers the privacy, space, and freedom that is hard to find at this price point. With no HOA, you'll have the flexibility to enjoy true country living with plenty of room for horses, livestock, RVs, trailers, ATVs, UTVs, and more. Upon arrival, you're greeted by a large, open parking area with ample space for vehicles,

  Kyle Footman ROGERS BARRY, REALTOR

  60 Bob White Trail, 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
• 

  

  /60

  $539,500

  • 4 Beds
  • 2 Baths
  • 1,718 Sq Ft

  333 N Post Oak Cir, Lloyd, FL 32344

  ENJOY THE QUIET SPACE OF THE SANCTUARY IN LLOYD*JUST 20 MINUTES FROM TALLAHASSEE* THIS FOUR BEDROOM TWO BATH HOME WAS BUILT IN 2020 WITH STYLISH FIXTURES AND DESIGN* ENJOY ONE ACRE ON A CORNER LOT WITH A FULLY FENCED BACKYARD* PLENTY OF SPACE FOR A BIG FAMILY AND PETS TO ROAM* THE HOME FEATURES A SPLIT BEDROOM FLOOR PLAN WITH A GORGEOUS OPEN LIVING, DINING AND KITCHEN SPACE* 2 CAR GARAGE AND

  

  Sarah Eden

  Eden & Company

  333 N Post Oak Cir, Lloyd, FL 32344
• 

  

  /61

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 2,873 Sq Ft

  761 Hawkins Rd, Monticello, FL 32344

  This one truly has it all! Nestled on 5+ private acres in beautiful Monticello, Florida, this 4-bedroom, 2.5-bath home offers the perfect blend of comfort, privacy, and charm. Step inside to a spacious split floor plan featuring 10-foot tray ceilings, real hardwood floors, a cozy wood-burning fireplace, and abundant natural light throughout. The beautifully updated kitchen features granite

  Kayla Meadows Keller Williams Town & Country

  761 Hawkins Rd, Monticello, FL 32344
• 

  

  /3

  $299,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,575 Sq Ft

  12180 Gamble Rd, Monticello, FL 32344

  New Construction currently being built by Southern Construction. Home should be completed in August 2026. Home is located in a great location in S. Jefferson County, close to the Wacissa River. Home features 3 beds and 2 baths, hardi siding, granite countertops with large kitchen island, open floor plan, and vinyl plank flooring in bedrooms and common area. Master bath features large walk-in tile

  Jared Parramore Coastwise Realty

  12180 Gamble Rd, Monticello, FL 32344
• 

  

  /18

  $25,000

  • Land
  • 4 Acres
  • $6,250 per Acre

  TBD S Salt Rd, Monticello, FL 32344

  This beautiful old Florida habitat is great for wildlife observation, birding, native forest growth, riding four-wheelers, building nesting boxes for ducks and bats or a hammock and a place to get away for primitive camping. Costco in Tallahassee, Florida is 30.4 miles and Walmart Supercenter in Perry, Florida is 32.1 miles. Monticello, Florida is 9.3 miles for Ice Cream and boutiques, shops,

  

  Lynette Sirmon

  All Realty Services

  TBD S Salt 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
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  /34

  $425,000

  • 5,818 Sq Ft

  2664 W Washington Hwy Unit Two Homes, Monticello, FL 32344

  Two houses perfect for generational living or rental income. These move-in-ready homes are in good condition, convenient to Monticello while maintaining privacy. The larger home is a 1550's era brick ranch-style home that is well maintained with newer roof (2022), new electric (2025), new plumbing (2025), tankless water heater and whole house generator. The main living area is 2,659 sf with 5

  Heather Boyd FL-GA Realty & Auction

  2664 W Washington Hwy Unit Two Homes, Monticello, FL 32344
• 

  

  /35

  $435,000

  • 3 Beds
  • 2 Baths
  • 1,919 Sq Ft

  1680 Willow Rd, Monticello, FL 32344

  Built in 2021 | 1,919 Sq. Ft. | Modern Upgrades | Move-In Ready Welcome home to this beautifully maintained 2021-built residence offering approximately 1,900 square feet of thoughtfully designed living space with today’s most sought-after features. This move-in ready home boasts an open-concept floor plan, durable luxury vinyl plank (LVP) flooring, abundant natural light, and high-end finishes

  

  Chance Shutes

  Keller Williams Town & Country

  1680 Willow Rd, Monticello, FL 32344
• 

  

  /29

  $434,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  285 Mallard Ln, Monticello, FL 32344

  One or more pictures is virtually enhanced *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

  Shelley Duke Red Bird Realty

  285 Mallard Ln, Monticello, FL 32344
• 

  

  /3

  $1,190,000

  • 4 Beds
  • 4 Baths
  • 3,043 Sq Ft

  4264 Safari Run, Tallahassee, FL 32309

  New construction, East side of town this 4 Bedroom 4 Bath home with office and private sitting in master this home is a luxury on 2/12 acres. completion in early Aug 2026

  Robert Paynter Keller Williams Town & Country

  4264 Safari Run, Tallahassee, FL 32309
• 

  

  /5

  $58,000

  • Land
  • 38,768 Sq Ft
  • $65,169 per Acre

  0 Spring Hollow Dr, Monticello, FL 32344

  Don't miss this exceptional 0.89-acre homesite in the Desirable Cooper's Pond community. This lot offers the perfect opportunity to create your dream home in a well-established neighborhood known for its attractive surroundings and welcoming atmosphere. Enjoy the convenience of being just minutes from town, with easy access to shopping, dining, schools, and everday amenities while still

  Ellen Fokes CONSULTANTS TO HOMEBUI

  0 Spring Hollow Dr, Monticello, FL 32344
• 

  

  /38

  $267,900

  • 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

  

  Pam Hoveland

  Landcorp, Inc.

  490 N Cherry Ct, Monticello, FL 32344
• 

  

  /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
• 

  

  /55

  $765,000

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

  9901 Gamble Rd, Monticello, FL 32344

  PRIVATE 20-ACRE ESTATE MINUTES FROM TALLAHASSEE - TRAILS, WILDLIFE, PASTURE & CUSTOM HOME (ADJOINING 21 ACRES AVAILABLE-MLS#400837) 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,

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  9901 Gamble Rd, Monticello, FL 32344
• 

  

  /10

  $253,080

  • Land
  • 21.09 Acres
  • $12,000 per Acre

  tbd Gamble Rd, Monticello, FL 32344

  Nature at its best, 21 acres of virgin forest with massive pines and a variety of hardwoods including a mixture of oaks, magnolias and hickory. Beautiful natural setting of rolling land with trails that meander through the property with an abundance of wildlife. Just up the road from the Wacissa River. The second parcel ID is 22-1S-3W-0000-0023-0000. ADJOINING HOME AND 20 ACRES AVAIABLE FOR

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  tbd Gamble Rd, Monticello, FL 32344
• 

  

  /14

  $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
• 

  /2

  $319,900

  New Construction $2K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,550 Sq Ft

  300 Bowman St, Monticello, FL 32344

  Recently built home featuring spacious open floor plan. Kitchen has raised cabinets, granite counters, stainless steel appliances, large island with plenty of seating & a pantry....overlooks spacious family area with plenty of room for large gatherings, plus separate dining space. First floor also offers 1/2 bath and large storage area under stairs. Upstairs you are greeted with open reading area

  Steve Walker Steve C. Walker Realty, LLC

  300 Bowman St, 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
• 

  

  /24

  $736,951

  • 2 Beds
  • 1 Bath
  • 1,296 Sq Ft

  10481 Ashville Hwy, Greenville, FL 32331

  Bring All Offers!!! Sportsman's Paradise Nature Preserve Quiet Country Living (2 Ponds) Bordering Plantation on 2 sides. "Out in the country past the city limit signs"..a diamond in the rough giving "Little House on the Prairie" vibes could easily be manicured and restored to perfection. Plenty of potential with almost 30 acres. Two ponds seem to be spring fed full of water, fantastic

  Starbuck Rissman Steve C. Walker Realty, LLC

  10481 Ashville Hwy, Greenville, FL 32331
• 

  

  /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 organic 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

  

  Ben Jones

  Mossy Oak Properties Southern Land and Homes, LLC

  Vacant N Salt Rd, Monticello, FL 32344
• 

  

  /44

  $390,000

  $40K PRICE INCREASE

  • 2,750 Sq Ft

  480 S Jefferson St, Monticello, FL 32344

  Located in the heart of Monticello, this 5-unit investment property offers a prime opportunity for investors looking to add value and generate income. Positioned just minutes from local businesses, shopping, dining, and convenient interstate access, the location provides strong appeal for tenants seeking both convenience and accessibility. Currently, 3 of the units are occupied, providing

  Chip Williams Keller Williams Town & Country

  480 S Jefferson St, Monticello, FL 32344
• 

  

  /38

  $90,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,864 Sq Ft

  340 S Waukeenah St, Monticello, FL 32344

  They don’t build them like they used to! This historic 1900 home located in downtown Monticello sits on nearly a half-acre lot and is full of timeless character waiting to be restored. Featuring original hardwood floors throughout most of the home, beadboard walls, 9+ foot ceilings, and original glass windows, this property offers the charm and craftsmanship so many buyers desire. Spacious

  Alicia Radtke All Realty Services

  340 S Waukeenah St, Monticello, FL 32344
• 

  

  /42

  $469,997

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  51 Tarn Way, Monticello, FL 32344

  MOVE IN READY!! Amazing new construction 3 bedroom 2 bathroom plus office. Luxurious master suite, Kitchen made of dreams, this is a must see!

  Amber McKinney Hamilton Realty Advisors LLC

  51 Tarn Way, Monticello, FL 32344
• 

  

  /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
• 

  

  /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
• 

  

  /43

  $375,000

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

  339 Silver Lake Rd, Monticello, FL 32344

  Large home on 5 acres mostly pasture~very peaceful setting~BRAND NEW LVP~Open concept with vaulted ceilings~large oaks~perfect pasture for horses or cattle~No HOA~

  Steve Walker Steve C. Walker Realty, LLC

  339 Silver Lake Rd, Monticello, FL 32344
• 

  

  /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
• 

  

  /63

  $259,999

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft

  196 Private Rd, Monticello, FL 32344

  Back on the market at NO FAULT TO THE SELLERS! Looking for a peaceful escape from the hustle and bustle? Welcome to your own private piece of North Florida! Tucked away on 5 beautiful acres between Tallahassee and historic Monticello, this spacious mobile home offers 1,664 square feet of comfortable living space with room to spread out and make it your own.Enjoy quiet mornings on the inviting

  Hunter Key OaksFeather Realty

  196 Private Rd, Monticello, FL 32344
• 

  

  /5

  $3,999

  $17K PRICE DROP

  • 2 Beds
  • 2 Baths

  10 S Front Ct, Monticello, FL 32344

  Celebrate our summer of savings with our limited-time offer! If you purchase this home, receive 2 months FREE site rent and pay NO application fees. Hurry, offer expires July 31, 2026. Act fast! Restrictions apply. Looking for an affordable home with plenty of potential? This handyman special is the perfect opportunity to add your personal touch and build instant sweat equity. With a functional

  Patty Davis Jefferson Pines

  10 S Front Ct, Monticello, FL 32344
• 

  

  /70

  $395,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,891 Sq Ft

  1637 N Jefferson Hwy, Monticello, FL 32344

  Awesome all brick 3 bedroom 2 bathroom home on 4 beautiful acres along North Jefferson Highway in Jefferson County, FL. Hardwood floors run throughout with tile in the kitchen and bathrooms. The kitchen offers solid wood cabinetry with soft-close drawers, updated appliances, and ample storage. Mature longleaf pines dot the property, which features a circular driveway and a 24x24 concrete pad with

  Catherine Hope All Realty Services

  1637 N Jefferson Hwy, 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
• 

  

  /27

  $227,900

  • 3 Beds
  • 2 Baths
  • 1,323 Sq Ft

  120 Larry's Ln, Monticello, FL 32344

  Recently renovated home on large lot out in the country. Quiet living at it's best only a couple miles from I-10. Metal roof, new carpet and LVP flooring, fresh paint and fixtures. Home is in great shape and move in ready.

  Randy Kamenicky Mainstreet Realty Of Tallahass

  120 Larry's Ln, Monticello, FL 32344

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