34

Monticello, FL Houses for Sale

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  • /42

    $345,000

    • 4 Beds
    • 2 Baths
    • 1,551 Sq Ft

    580 Holly Rd, Monticello, FL 32344

    Looking for that small town life but still wanting to be close to Tallahassee? This is it! The quiet neighborhood of Crooked Creek subdivision could be the place for you! Located just outside of Monticello, FL. this roomy 4 bedroom, 2 bathroom 2012 built house has it all. Beautifully land scaped yard with two gazebos and a greenhouse. Vaulted ceilings in the main living area and large over sized

    Agent Photo

    Anthony Gifford

    Ketcham Realty Group, Inc.

    (850) 616-7294

    580 Holly Rd, Monticello, FL 32344
  • /42

    $1,125,000

    • 3 Beds
    • 1 Bath
    • 1,146 Sq Ft

    740 Kinsey Rd, Monticello, FL 32344

    Location: Jefferson County, FL Size: 155 acres Features: Rolling pastures Planted pines Natural hardwoods Pond Home: 1941 built 1,146 square feet Updated Outbuildings: With power Opportunities for workshops, storage, and more Additional Homesites: Breathtaking views Peaceful living Proximity: 10 miles from downtown Monticello, FL 5 miles to I-10 Wildlife: Deer Turkey Waterfowl

    Ben Jones Southern Land & Homes

    740 Kinsey Rd, Monticello, FL 32344
  • /42

    $495,900 New Construction

    • 3 Beds
    • 2 Baths
    • 2,061 Sq Ft

    350 Oconee, Monticello, FL 32344

    Welcome to Covey Run, a private estate community in the heart of Monticello. Your new 3 bedroom 2 bath 2 car garage sits on 2.24 acres. Home features open floor plan with primary on-suite and large walk-in closet. Kitchen is ready for the chef in mind with gas range and plenty of room for prep. Living room features 10 foot ceilings, fireplace and opens to a sunroom. House has Generac Home

    Steve Walker Steve C. Walker Realty, LLC

    350 Oconee, Monticello, FL 32344
  • /27

    $450,000

    • 3 Beds
    • 2 Baths
    • 2,131 Sq Ft

    133 Devane Rd, Monticello, FL 32344

    Peaceful 10-Acre Country Retreat with Pool - Just Outside Chattahoochee, FL Discover the charm of country living with this spacious 3-bedroom, 2-bath single-family home located just minutes from the quaint town of Chattahoochee, Florida. Enter through the winding tree lined road that sets the stage for the home that welcomes you at the end. Set on a beautifully wooded 10-acre parcel, this 2,131

    Bubba McCants EXP Realty LLC

    133 Devane Rd, Monticello, FL 32344
  • /39

    $675,000 Open Sat 11AM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 2,771 Sq Ft

    44 S Ojibwa Rd, Monticello, FL 32344

    Escape the hustle and enjoy peaceful country living with the convenience of modern amenities! This spacious 4 bedroom, 3.5 bathroom home offers 2,771 square feet of well-designed space sitting on 5 beautiful acres with producing pecan trees. Whether you're ready to start your homesteading journey or simply want more space and privacy, this property is ready for you. With plenty of room to grow,

    Brett Miller Hollifield Real Estate Group

    44 S Ojibwa Rd, Monticello, FL 32344
  • /42

    $685,000

    • 3 Beds
    • 2.5 Baths
    • 3,214 Sq Ft

    150 N Ojibwa Rd, Monticello, FL 32344

    Peaceful 5.10+ acre retreat in Objiwa Acres! This beautifully maintained 3BR/2BA home offers space, privacy, and flexibility—surrounded by a manicured lawn, rows of pecan trees, a dedicated herb garden, and a saltwater plunge pool with fountain. Enjoy multiple outdoor living spaces including a screened front porch, screened back porch, and a bright true Florida room with vaulted ceilings. A

    Hettie Spooner Hill Spooner & Elliott Inc

    150 N Ojibwa Rd, Monticello, FL 32344
  • /42

    $449,000

    • 4 Beds
    • 3 Baths
    • 2,832 Sq Ft

    4710 Waukeenah Hwy, Monticello, FL 32344

    Monticello living is good, peaceful living. This home is ready for a multi-generational family, or a family with loads of relatives and friends to entertain. This three bedroom, two bath home has an adjacent mother in law suite complete with bedroom, kitchen, bath and living room. Located on two acres with a 2025 a/c unit, 2019 roof, large screened and unscreened porch, 3 pad carport, 3

    Fay Armstrong Keller Williams Town & Country

    4710 Waukeenah Hwy, Monticello, FL 32344
  • /34

    $650,000

    • 5 Beds
    • 5 Baths
    • 3,770 Sq Ft

    974 Hiawatha Farms Rd, Monticello, FL 32344

    OPEN HOUSE 2-4pm Saturday, May 17th & 2-4pm Sunday May 18th! Perfect blend of comfort and flexibility on this beautiful, horse-friendly property spanning over 6 acres. The main home offers 3 bedrooms and 3 full bathrooms, featuring a spacious layout designed for everyday living and effortless entertaining. Just steps away, a detached 2-bedroom, 2-bath in-law suite provides the ideal setup for

    Kayana Gaines Hill Spooner & Elliott Inc

    974 Hiawatha Farms Rd, Monticello, FL 32344
  • /42

    $599,900

    • 4 Beds
    • 5 Baths
    • 3,862 Sq Ft

    3873 N Jefferson St, Monticello, FL 32344

    Stunning 4 Bedroom, 3.5 Bath Home on 9.73 Acres with Large Detached Garage plus Oversized Attached 2 Car Garage Located just north of this spacious 3,862 square foot home sits on 9.73 acres with a tranquil creek running through the rear of the property. The home is built on high and dry ground, and not located in a flood zone or HOA. Built in 2007, the home features 10-foot ceilings,

    Stephanie Dobson Southern Land & Homes

    3873 N Jefferson St, Monticello, FL 32344
  • /42

    $609,900

    • 3 Beds
    • 2.5 Baths
    • 2,560 Sq Ft

    181 Heritage Blvd, Monticello, FL 32344

    Craftsman style house in Heritage Hills subdivision~ The house features 3 bedrooms/2 bathrooms and is energy efficient (Green Certified) ~ Luxurious hardwood flooring and a deluxe primary bathroom with separate jetted tub & large shower ~ Custom built-in cabinets in the living room and office ~ Regal craftsman style interior trim throughout and stainless-steel appliances ~ Exterior freshly

    Mariela Bartens Coldwell Banker Hartung

    181 Heritage Blvd, Monticello, FL 32344
  • /34

    $465,000

    • 4 Beds
    • 3 Baths
    • 2,076 Sq Ft

    376 Tecumseh Rd, Monticello, FL 32344

    Gorgeous multigenerational, ranch style, 4 Bedroom/3 Bath home with 5th room that can be used as an office or additional bedroom. Perfect for a growing or downsizing family! Home rests on 4.60 acres of outdoor, partially wooded paradise. Enjoy tranquility from the all-season rear porch-removable panels allow you to turn room into a screened porch in minutes. Many recent updates include freshly

    Casey Skelton Pearson Realty Inc.

    376 Tecumseh Rd, Monticello, FL 32344
  • /3

    $469,995 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,940 Sq Ft

    52 Mire Ct, Monticello, FL 32344

    Amazing new construction 3 bedroom 3 bathroom by Nailed It Tallahassee LLC Come pick out all your finishes, home scheduled for completion August 2025. Luxurious master suite, Kitchen made of dreams, this is a must see! Preferred Lender offering 1% in closing costs! Photos of previous home come make this one your own!

    Amber McKinney Hamilton Realty Advisors LLC

    52 Mire Ct, Monticello, FL 32344
  • /41

    $460,995 New Construction

    • 3 Beds
    • 2 Baths
    • 1,806 Sq Ft

    47 Mire Ct, Monticello, FL 32344

    Amazing new construction 3 bedroom 2 bathroom by Nailed It Tallahassee LLC Come pick out all your finishes, home scheduled for completion August 2025. Luxurious master suite, Kitchen made of dreams, this is a must see! Preferred Lender offering 1% in closing costs! Photos of previous home come make this one your own!

    Amber McKinney Hamilton Realty Advisors LLC

    47 Mire Ct, Monticello, FL 32344
  • /36

    $435,000

    • 3 Beds
    • 2 Baths
    • 2,020 Sq Ft

    259 Barnes Rd, Monticello, FL 32344

    Spacious Brick on 4.25 acres. Easy Thomasville commute. Discover peace and privacy with this well maintained brick ranch nestled in the woods. Step into the spacious living room with cozy wood burning fireplace, ideal for relaxing evenings or entertaining. Office, large utility room, 2 car garage, and workshop are some of the extras. Enjoy this quiet private setting.

    Pam Kelly Kelly & Kelly Properties, Inc

    259 Barnes Rd, Monticello, FL 32344
  • /38

    $424,900

    • 4 Beds
    • 2 Baths
    • 1,809 Sq Ft

    115 Crooked Creek Ln, Monticello, FL 32344

    New Construction in Crooked Creek on a spacious .72 acre lot! This open plan features 4 bedrooms, 2 bathrooms, 2 car garage, and beautiful shiplap accent walls. The kitchen has a light and bright design with white cabinets, quartz counters, subway tile backsplash, and GE stainless appliances. LVP flooring throughout (tile in baths), fireplace, covered back patio, and pre-wired for security and

    Amber Renaud The Nova Group Realty

    115 Crooked Creek Ln, Monticello, FL 32344
  • /42

    $1,599,000

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

    221 Kiley Dr, Monticello, FL 32344

    Welcome to a rare and exquisite, turn-key, 15-acre modern luxury estate, where timeless elegance meets Southern charm. Custom built by Riley Palmer, this exclusive, gated property is nestled just minutes from Tallahassee, Florida's Capital City, and Thomasville, GA in Monticello-home to a storied opera house and chic dining options-and offers the perfect blend of privacy, prestige and proximity.

    Barbra Engel & Volkers Tallahassee

    221 Kiley Dr, Monticello, FL 32344
  • /42

    $1,200,000

    • 5 Beds
    • 5.5 Baths
    • 4,700 Sq Ft

    1165 Dills Rd, Monticello, FL 32344

    Nature Lover’s Dream – Custom Estate on 21+ Acres. Escape to peace and privacy in this stunning custom-built home surrounded by over 21 acres of natural beauty. Thoughtfully designed with both comfort and function in mind, this spacious estate features a gourmet kitchen with gas stove and butler’s pantry, formal and casual living spaces, a cozy library, and a luxurious primary suite with porch

    Callie Rhoads The Naumann Group Real Estate

    1165 Dills Rd, Monticello, FL 32344
  • /42

    $265,000

    • 3 Beds
    • 2 Baths
    • 2,390 Sq Ft

    2436 N Jefferson Hwy, Monticello, FL 32344

    Discover the perfect blend of rustic charm and opportunity with this unique country property. Nestled on 3+ acres, this older farm house offers character and room to grow. The main home features spacious living areas with wood floors throughout and plenty of potential for updates to make it your own. Front screen porch and large utility room. Also included is a second block home. Additional

    Pam Kelly Kelly & Kelly Properties, Inc

    2436 N Jefferson Hwy, Monticello, FL 32344
  • /19

    $299,000

    • 4 Beds
    • 2 Baths
    • 1,858 Sq Ft

    575 E Palmer Mill Rd, Monticello, FL 32344

    Spacious home located within walking distance of Historic Downtown Monticello. This four bedroom home sits quietly on a manageable half acre lot. Sporting both original hardwood flooring and newly installed LVP flooring, this home blends perfectly for any new home owners. Updated bathrooms and appliances have all been done within the last 5 years. Sizes are approximate.

    Caleb Stephens Waypoint Properties East

    575 E Palmer Mill Rd, Monticello, FL 32344
  • /41

    $365,000

    • 2 Beds
    • 1.5 Baths
    • 1,140 Sq Ft

    265 Still Rd, Monticello, FL 32344

    This inviting 2-bedroom, 1.5-bath home sits on 5 peaceful acres between Monticello, FL, and Thomasville, GA, offering a great mix of indoor comfort and outdoor space. It’s just as cute as you want it, with endless potential for outdoor living! Inside, the open great-room layout feels both spacious and cozy, with a large utility room leading to the screened porch and a covered carport that’s

    Catherine Hope All Realty Services

    265 Still Rd, Monticello, FL 32344
  • /37

    $419,900

    • 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
  • /41

    $374,999

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

    4081 Gamble Rd, Monticello, FL 32344

    Nestled on a serene 5-acre retreat, this charming storybook cottage feels like a hidden gem, yet it’s just 15 minutes from downtown Monticello’s quaint shops and restaurants. Tucked back from the road for ultimate privacy, this well-maintained home is surrounded by natural beauty, including native plants, wild azaleas, and lush greenery. Step onto the inviting front porch and into a warm,

    Malissa Henning EXP Realty, LLC

    4081 Gamble Rd, Monticello, FL 32344
  • /40

    $1,390,000

    • 4 Beds
    • 6 Baths
    • 9,848 Sq Ft

    193 Nautilus Dr, Monticello, FL 32344

    Introducing a breathtaking fusion of modern convenience and medieval charm nestled in the heart of the woods. This meticulously renovated 9,848 square foot architectural marvel boasts a captivating design, featuring uniquely sized windows and curving walls that exude artistic allure at every turn. Step inside and experience the epitome of luxury living. The main building offers a seamless blend

    Ondrea Maldonado Hamilton Realty Advisors LLC

    193 Nautilus Dr, Monticello, FL 32344
  • /40

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,985 Sq Ft

    480 W Washington St, Monticello, FL 32344

    OWNERS MOTIVATED-ALL REASONABLE OFFERS WILL BE CONSIDERED.Step Back In Time! Rare chance to own your own piece of "Old Florida". Craftsman Style beauty with soaring 10 ' bead-board ceilings and 10 " baseboards, original pine floors and 4 gas fireplaces. Perfect blend of old Florida charm and modern conveniences. Statuary Marble countertops and copper sink in kitchen, extra large dining room for

    Pam Kelly Kelly & Kelly Properties, Inc

    480 W Washington St, Monticello, FL 32344
  • /41

    $425,000

    • 5 Beds
    • 4 Baths
    • 3,330 Sq Ft

    4131 N Jefferson Hwy, Monticello, FL 32344

    3330 square foot home on a beautiful 6 acre property that backs up to Pine Haven Plantation! This is a solid brick home with a 2016 metal roof and a 2018 HVAC unit and well pump. The home was purchased back in 2023 and gutted along with some extensive repairs done to bones of the home. It is now waiting for the perfect person to come in and finish her out with their personal touches. The main

    Catherine Hope All Realty Services

    4131 N Jefferson Hwy, Monticello, FL 32344
  • /40

    $285,000

    • 3 Beds
    • 2 Baths
    • 2,206 Sq Ft

    185 Main St, Monticello, FL 32344

    Nestled in the heart of historic Lloyd, this beautiful 1914 Charmer boasts the craftsmanship of an older home with the luxuries of brand new finishes! This Beautiful 3 Bedroom, 2 Bath home has been tastefully remodeled, ready for it's new family. It property possesses 4 new electric fireplaces with brand new tiling throughout. Any couple will enjoy the huge double-head shower with a matching

    Lee Hall Capital City Real Estate Group

    185 Main St, Monticello, FL 32344
  • /20

    $269,000

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

    170 W Cherokee Ave, Monticello, FL 32344

    Know vacant!! We have owned this home for 15 years. It was fully remodeled one year ago. It has a new roof, insulation, HVAC including ductwork, new drywall, new ceilings, light fixtures, plumbing, electrical. New kitchen and baths. Large corner lot. Walk to the grocery store. This is a new home with older home charm. Original oak floors in most of the house, fireplace. Home is rented till

    Ken Foster FosterGrant Real Estate, LLC

    170 W Cherokee Ave, Monticello, FL 32344
  • /18

    $239,900

    • 4 Beds
    • 3 Baths
    • 2,553 Sq Ft

    34 W Hummingbird Ln, Monticello, FL 32344

    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 room with laundry is in the middle of the home. Each side has an enclosed porch too! So much space and an

    Susan Gillespie Lord & Stanley Realty, Inc.

    34 W Hummingbird Ln, Monticello, FL 32344
  • /2

    $589,000

    • 3 Beds
    • 2.5 Baths
    • 1,924 Sq Ft

    XXX Taylor Rd, Monticello, FL 32344

    Proposed Construction on 5.2 acres Taylor Rd. Wonderful Jefferson County location. Minutes from I-10/ Gamble Rd. + downtown Monticello. New 5 lot mini subdivision paved frontage, minimal restrictions to protect values. Underground County water available.

    Kevin Davis The Naumann Group Real Estate

    XXX Taylor Rd, Monticello, FL 32344
  • /32

    $595,000

    • 3 Beds
    • 3 Baths
    • 3,026 Sq Ft

    3827 N Jefferson St, Monticello, FL 32344

    Spacious Contemporary Home on 5 Acres with Pond, Minutes from Thomasville, Ga! Enjoy peaceful country living with modern comforts in this stunning 3 bedroom, 3 bathroom brick home on 5 beautiful acres with a private pond. With over 3,000 square feet of living space, this property offers room to spread out and features thoughtful touches throughout. Inside, you'll find a large den with cozy

    Pam Kelly Kelly & Kelly Properties, Inc

    3827 N Jefferson St, Monticello, FL 32344
  • /5

    $250,000

    • 3 Beds
    • 2 Baths
    • 1,210 Sq Ft

    1490 Hampton Place, Monticello, FL 32344

    Great single family home situated on large lot in desirable Coopers Pond Community near I-10 East. Own this 3 bedrooms 2 bathrooms home as a first time home buyer or retirement home. It is currently occupied with a tenant and can be purchased with an opportunity of immediate income. New roof 2024, ceramic tile floors throughout, partially fenced back yard, large patio with one car garage. A

    Jackie Austin Shamrock Professionals Realty

    1490 Hampton Place, Monticello, FL 32344
  • /31

    $694,000

    • 3 Beds
    • 2.5 Baths
    • 2,344 Sq Ft

    17 Old Tung Grove Rd, Monticello, FL 32344

    Ready to move into your new home. The Ridge At Tung Grove. A small subdivision of only 5 lots. A spectacular rural location with convenient access to Tallahassee, only a 12 minute drive away. Another quality new home by Southern Coastal Homes on 6.82 wooded acres. 3 bedroom 2 bath with a bonus room with half bath. Open living space. Spacious mud room and laundry room with built ins. Other lots

    Barry Kelly Kelly & Kelly Properties, Inc

    17 Old Tung Grove Rd, Monticello, FL 32344
  • /24

    $430,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,865 Sq Ft

    173 Deerfield Ln, Monticello, FL 32344

    PHOTOS COMING SOON! Welcome to this beautifully maintained 3-bedroom, 2-bath home offering the perfect blend of peaceful country living and modern upgrades. Nestled on a full acre of land, this charming property is a rare gem with no HOA restrictions—giving you the freedom to truly make it your own. Step inside and be captivated by the open and inviting floor plan, featuring both a formal living

    Pamela Jordan-williams Superior Realty Group LLC

    173 Deerfield Ln, Monticello, FL 32344
  • /27

    $349,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,601 Sq Ft

    149 Coopers Pond Rd, Monticello, FL 32344

    New build, under construction on 1.05 acres, close to downtown Monticello and no HOA!! Five mins to I-10 and four mins to US90. Completion date set for April 2025 - - > see similar new build, under construction @ 81 Coopers Pond on 2.62 acres @ $399,900. Highlights of builder specs are as followed: - 1601sqft - 3 bedrooms - 2 full baths - 10' tray ceiling in living room - LVP throughout -

    Tiffany Kasdorf The Nova Group Realty

    149 Coopers Pond Rd, Monticello, FL 32344

Why Live in Monticello

Founded in 1827, the small town of Monticello is blooming with historic charm and community spirit. As the seat of Jefferson County, the downtown area is home to multiple buildings dating from the 1800s, including the historic Perkins Opera House, as well as restaurants, coffee shops, boutiques, bed and breakfasts and more. “Monticello is a modern-day Mayberry. People are very nice. When somebody passes away, everybody goes to the funeral, and it’s standing room only. It's caring and neighborly,” says Lynette Sirmon, a real estate agent with Al ...

Home Trends in Monticello, FL

Housing Trends

Median Sale Price
$385,000
Median Single Family Sale Price
$399,950
Average Price Per Sq Ft
$206
Number of Homes for Sale
35
Last 12 months Home Sales
89
Months of Supply
4.70
Median List Price
$419,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
29%
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