Jefferson County FL Houses for Sale

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  /27

  $349,000

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

  8156 Waukeenah Hwy, Monticello, FL 32344

  Rare Find! Country Living on 1 Acre-No HOA! Enjoy peaceful country living on a full 1-acre property with no HOA restrictions. This spacious 1774 square foot home features 3 bedrooms and 2 bathrooms with a bright open concept layout. The home features LVP flooring throughout, fresh interior paint in main living area, and a new roof in 2023 for added piece of mind. The primary suite includes a

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  8156 Waukeenah Hwy, Monticello, FL 32344
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  /57

  $529,000

  $56K PRICE DROP

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

  515 E Palmer Mill Rd, Monticello, FL 32344

  **MOTIVATED SELLERS - CONCESSION(S) BEING OFFERED** 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,

  

  Brenna Kelly-Ward

  Kelly & Kelly Properties, Inc

  515 E Palmer Mill Rd, Monticello, FL 32344
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  /67

  $425,000

  $25K PRICE INCREASE

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

  701 Barber Hill, Lamont, FL 32336

  (One or more photos has been virtually staged) Just reduced! 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,

  

  JoAnn Jacobs

  Coldwell Banker Hartung

  701 Barber Hill, Lamont, FL 32336
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  /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
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  /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

  

  Chance Shutes

  Keller Williams Town & Country

  305 Old Lloyd Rd, Monticello, FL 32344
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  /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
• 

  

  /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.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  220 Eaton St, Monticello, FL 32344
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  /30

  $149,900

  $25K PRICE DROP

  • 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

  

  Carmen Mansfield

  McClellan Realty, LLC

  167 Phelps Rd, Lamont, FL 32336
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  /42

  $519,000

  $31K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,134 Sq Ft

  121 Shumard Ct, Monticello, FL 32344

  Beautiful, like-new 2022 farmhouse-style home located in the sought after Crooked Creek area. This spacious 2134 sq ft home features 4 bedrooms and 2.5 baths on a generous .85 acre lot, ideally situated on a quiet cul-de-sac on the west side of Monticello. The open-concept layout offers elegant coffered ceilings crown molding and a cozy gas fireplace with built-in shelving in the living room-

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  121 Shumard Ct, Monticello, FL 32344
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  /41

  $499,000

  $51K PRICE DROP

  • 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

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  398 Tecumseh Rd, Monticello, FL 32344
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  /36

  $584,000

  Open Sat 10AM - 1PM

  • 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
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  /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

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  640 Nautilus Dr, Monticello, FL 32344
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  /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
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  /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

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  205 N Rhodes St, Monticello, FL 32344
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  /70

  $2,000,000

  • 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 18 beautiful acres. 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 baths, while the downstairs includes 2 bedrooms,

  

  Chance Shutes

  Keller Williams Town & Country

  305 Old Lloyd Rd, Monticello, FL 32344
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  /49

  $398,900

  $26K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,127 Sq Ft

  1628 N Jefferson Hwy, Monticello, FL 32344

  For generations, this beautifully maintained, one-family owned brick home has been a place where holidays were celebrated, children were raised, and life's everyday moments became treasured memories. Today, with only one family member remaining, the home has simply become more space than one person needs. Rather than seeing it sit too quietly, she hopes to pass it on to another family who will

  

  Lynette Sirmon

  All Realty Services

  1628 N Jefferson Hwy, Monticello, FL 32344
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  /57

  $699,000

  • 6 Beds
  • 3.5 Baths
  • 3,114 Sq Ft

  365 S Mulberry St, Monticello, FL 32344

  Historic soul. Modern substance. A rare circa-late 1800s home, beautifully restored and thoughtfully made NEW. Some houses simply endure... and some are given the rare chance to begin again. Better than New Construction! Just two blocks from the courthouse square in Monticello, Fl, this circa-late 1800s home—a classic Southern I-house shaped by Greek Revival influence—once stood quietly

  Lee Hall Bespoke Realty of Tallahassee

  365 S Mulberry St, Monticello, FL 32344
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  /57

  $599,000

  • 7 Beds
  • 7 Baths
  • 5,139 Sq Ft

  625 E Washington St, Monticello, FL 32344

  Introducing a stunning 1.2 acre estate in the heart of Historic Downtown Monticello. The Simon-Ridgeway home was built in 1888 and boasts a generous 4,500 sq ft of living space and features 7 spacious bedrooms, 5 of which come with its own en-suite bathroom for ultimate privacy and convenience. City granted BNB status - making this perfect for an owner/occupier wanting to work from home and enjoy

  Lee Hall Bespoke Realty of Tallahassee

  625 E Washington St, Monticello, FL 32344
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  /20

  $295,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft

  170 W Cherokee Ave, Monticello, FL 32344

  We have owned this home for 15 years. It was fully remodeled 2024. It has a new roof, insulation, HVAC including ductwork, new drywall, new ceilings, light fixtures, plumbing, electrical. New kitchen and baths. Granite counters, white shaker cabinets, large corner lot. Walk to the grocery store. This is like a new home with older home charm. Original oak floors in most of the house, fireplace.

  Ken Foster FosterGrant Real Estate, LLC

  170 W Cherokee Ave, Monticello, FL 32344
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  /66

  $379,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,280 Sq Ft

  1012 S Main Ave, Monticello, FL 32344

  Tucked away on 5 private acres down a quiet, wooded road, this brick home offers 2,280 square feet with a split floor plan featuring 3 bedrooms and 2 baths, providing both space and functionality. New HVAC June 2026 with 10 year parts warranty, plus new roof November 2025, Well 2022, and septic drain field replaced 2016. Inside, you’ll find a cozy fireplace and a bright sunroom that brings the

  Catherine Hope All Realty Services

  1012 S Main Ave, Monticello, FL 32344
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  /38

  $429,900

  $20K PRICE DROP

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

  107 S Tarn Way, Monticello, FL 32344

  Welcome to this beautifully custom-built 3 bedroom, 2 bath home completed in 2024 and located in the desirable Hemings Pond Subdivision. Offering the perfect blend of modern construction and thoughtful upgrades, this move-in ready showcases luxury vinyl plank flooring, upgraded light fixtures, premium countertops, and elegant bath fixtures. Owner selected custom enhancements elevate the space

  Joana Villeneuve Hill Spooner & Elliott Inc

  107 S Tarn Way, Monticello, FL 32344
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  /24

  $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
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  /61

  $1,100,000

  Open Sat 1PM - 4PM

  • 3 Beds
  • 3 Baths
  • 2,815 Sq Ft

  458 Watermill Rd, Monticello, FL 32344

  Country Living at Its Finest! This stunning 2,800-square-foot 3-bedroom, 3-bath home is nestled on nearly 30 breathtaking acres. Offering the perfect blend of comfort, beauty, and functionality, this exceptional property is ideal for those seeking peaceful country living without sacrificing modern amenities. Inside, you’ll find spacious living areas with high ceilings, an eat-in kitchen, family

  D. Scott Kilgore Superior Realty Group LLC

  458 Watermill Rd, Monticello, FL 32344
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  /70

  $754,000

  $41K PRICE DROP

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

  660 Whispering Hill, 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 Hill, 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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  /31

  $679,900

  $55K PRICE INCREASE

  • 4 Beds
  • 3 Baths
  • 2,716 Sq Ft

  140 Shumard Ct, Monticello, FL 32344

  NOW INCLUDES ADDITIONAL LOT!! 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

  Caleb Stephens Silo Hill Properties

  140 Shumard Ct, Monticello, FL 32344
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  /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
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  /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
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  /46

  $347,500

  • 4 Beds
  • 2 Baths
  • 2,162 Sq Ft

  4081 Gamble Rd, Monticello, FL 32344

  Escape to your own private 5-acre retreat! A long, secluded driveway leads to this charming cottage-style 4-bedroom, 2-bath home nestled among mature trees and surrounded by the natural beauty of North Florida. Enjoy the peace and privacy you've been dreaming of with no HOA and no flood insurance required. Featuring a brand-new roof, versatile bonus space, two-car carport, and storage shed, this

  Alisa McMahon Bluewater Realty Group

  4081 Gamble Rd, Monticello, FL 32344
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  /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
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  /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
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  /44

  $235,000

  • 3 Beds
  • 1 Bath
  • 1,700 Sq Ft

  810 E Dogwood St, Monticello, FL 32344

  Step back in time and discover the charm of this classic Monticello home, offering timeless character and endless possibilities. Built in 1915, this Craftsman-style residence features 1,700 square feet of living space with hardwood floors, separate living and dining areas that reflect the home's historic appeal, 3 full bedrooms, with a large mud room and separate sitting room, a wood-burning

  Michael Balanoff Re/Max Professionals Realty

  810 E Dogwood St, Monticello, FL 32344
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  /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
• 

  /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
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  /52

  $395,000

  $54K 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
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  /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
• 

  

  /19

  $434,900

  New Construction $10K 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
• 

  /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
• 

  

  /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

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