Homes for Sale in 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
• 

  

  /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
• 

  

  /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
• 

  

  /70

  $470,000

  Open Sat 11AM - 1PM $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
• 

  

  /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
• 

  

  /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 Open Sat 11AM - 1PM

  • 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

  $60,000

  $20K PRICE INCREASE

  • 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.

  Malcolm Davis Broger Real Estate Services

  0 Central Rd Unit 381525, Midway, 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
• 

  

  /19

  $424,900

  New Construction $20K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /70

  $700,000

  • 3 Beds
  • 2.5 Baths
  • 2,160 Sq Ft

  660 Whispering Hills Rd, Monticello, FL 32344

  Set on 18+ acres of beautifully maintained pasture, this private country property is built for both everyday living, true equestrian use or small livestock farm. The land is the star- fully fenced with new wood fencing that cleanly defines multiple pastures, a peaceful pond, and wide open space to ride, graze and enjoy. The 6-stall horse barn is ready to work with paddocks attached to each stall,

  Catherine Hope All Realty Services

  660 Whispering Hills Rd, Monticello, FL 32344
• 

  

  /49

  $175,000

  • 2 Beds
  • 1 Bath
  • 1,488 Sq Ft

  1060 S Water St, Monticello, FL 32344

  If you are looking for your opportunity, this home's for you! This 1950's bungalow is within reach for all. Whether a first time buyer, down-sizer, or investor, this home has ample opportunity for all! At a price where designer re-dos and renovations are possible, anyone can can make this dream come true! The huge addition (500+ sqft) off the rear of the home offers ample square footage that

  Sarah Springer Pathways Realty

  1060 S Water St, Monticello, FL 32344
• 

  

  /34

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,980 Sq Ft

  112 Long Leaf Dr, Monticello, FL 32344

  Nearly 6 Acres of Opportunity in Beautiful Monticello! If you're looking for space, privacy, and the possibility to create a home that truly reflects your vision, this property is it! This spacious 3-bedroom, 2-bathroom modular home offers a desirable open and split floor plan with generously sized living spaces. The expansive primary suite provides a private retreat and features a walk-in

  Marylou Johnston Keller Williams Town & Country

  112 Long Leaf Dr, Monticello, FL 32344
• 

  

  /44

  $364,900

  $15K 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
• 

  /2

  $49,500

  $20K PRICE DROP

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

  Lot 16 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 4 Lots- 16 & 17 with 18 & 19 directly behind it, totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 16 E Washington St, Monticello, FL 32344
• 

  

  /56

  $299,900

  • 3 Beds
  • 2 Baths
  • 2,583 Sq Ft

  515 Sunset Dr, Monticello, FL 32344

  Great opportunity to be in the lovely town of Monticello off of Pearl Street. Acre lot & Concrete swimming pool with this single story home. Large rooms, hardwood floors throughout much of the house, updated kitchen cabinetry, large detached garage. House has been cleaned up & some fresh painting done but does need work and is priced accordingly. Being sold AS-IS w/right to inspect.

  Nancy Stedman Coldwell Banker Hartung

  515 Sunset Dr, Monticello, FL 32344

Showing Results 41 - 80, Page 2 of 3