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$269,900
3 Beds ⋅ 2 Baths ⋅ 401821 MLS
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, equipment, and guests. The expansive front porch sets the tone, inviting you to enjoy quiet mornings with a cup of coffee overlooking your land and relaxing evenings surrounded by nature. Inside, the well-maintained home features a functional layout designed for everyday living and entertaining. The entry opens into a spacious family room, separate living room, and dining area just off the kitchen, offering multiple gathering spaces. The generously sized kitchen provides abundant workspace and connects to a dedicated laundry room for added convenience. The split-bedroom floor plan offers privacy, with the primary suite featuring a garden tub, double vanities, and a walk-in closet. On the opposite side of the home, you'll find two additional bedrooms and a full guest bathroom. Step outside to the screened-in porch, the perfect place to entertain family and friends or simply relax while taking in the peaceful surroundings. The property also includes a heated and cooled shed that's ideal for a home office, gym, or creative studio, a fire pit for evenings under the stars, and an additional storage shed. Complete with a fenced yard and meticulously maintained grounds, this versatile property offers a rare opportunity to enjoy the privacy, flexibility, and lifestyle that only acreage living can provide.

60 Bob White Trail, Monticello
$139,000
401806 MLS
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.

tbd Orchard, Monticello
$139,000
401805 MLS
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.

TBD Orchard Lane, Monticello
$539,500
4 Beds ⋅ 2 Baths ⋅ 401695 MLS
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 GORGEOUS COMMUNITY WITH NO HOA FEES*

333 Post Oak Circle, Monticello
$254,999
3 Beds ⋅ 2 Baths ⋅ 401558 MLS
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 1,792 square feet of comfortable living space with room to spread out and make it your own.Enjoy quiet mornings on the inviting front porch with a cup of coffee or unwind in the evenings on the large back porch overlooking your own slice of paradise. The property is enhanced by a beautiful collection of mature trees and landscaping, including cedar, hickory, southern magnolia, Japanese loquat, hardy orange, mulberry, pineapple guava (Feijoa), camellias, crape myrtles, Chinese fringe flowers, Spanish Sunset roses, holly, and more—creating year-round beauty, shade, and privacy.Nature lovers will appreciate the seasonal creek that meanders through the property, adding to the peaceful setting and attracting local wildlife. Two storage sheds provide plenty of space for tools, equipment, hobbies, or additional storage. Whether you’re looking for a homestead, hobby farm, weekend retreat, or simply a place to enjoy the freedom and tranquility of country living, this property offers endless possibilities. Experience the best of both worlds—privacy, acreage, and natural beauty—while remaining just a short drive from Tallahassee, Monticello, shopping, dining, and everyday conveniences.

196 Private Road, Monticello
$539,000
4 Beds ⋅ 3 Baths ⋅ 401514 MLS
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 countertops, a stone backsplash, tiled flooring, a large pantry, and a charming breakfast nook. The inviting living room opens through French doors to an expansive screened porch—the perfect place to relax while enjoying the peaceful views, birds, and local wildlife. The spacious primary suite is a true retreat with three large bay windows, private access to the screened porch, a luxurious ensuite bath featuring a deep whirlpool tub, walk-in shower, double vanities, and an oversized walk-in closet. Outside, you'll find even more to love, including a 2022 roof, 2 - 2 car garages - an oversized attached garage, an additional detached two-car garage, and a red barn complete with power and lighting. Additional upgrades include LeafFilter gutters, a water softener system, and both the front and backyard are fenced for added privacy and functionality. Manual transfer switch with 50 amp RV plug installed early last year If you've been dreaming of peaceful country living without sacrificing modern conveniences, this property is a must-see!

761 Hawkins Road, Monticello
$299,900
3 Beds ⋅ 2 Baths ⋅ 401502 MLS
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 shower. Home is situated on larger over an acre lot, with plenty of room for the entire family!! Come see all this home has to offer today!!

12180 Gamble Road, Monticello
$25,000
401490 MLS
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, churches and restaurants.

TBD S Salt Road, Monticello
$425,000
401409 MLS
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 bedroom and 2 full bathrooms. There's also a sunroom, and a 396 sf attached bonus room suitable for an office or workshop, plus 3 small outbuildings, one with working electric. The guest house includes 3 bedrooms and 2 bathrooms. Built in the 1950's, it's functional but not fancy. It is in good condition with newer roof, plumbing (2025), and electric (2025). Both homes have a fresh coat of paint. The houses are on 2 separate contiguous parcels (1.3 ac and 0.64 ac) but are being offered together. A great housing buy for someone looking for a lot of living space.

2664 W Washington Highway Unit Two Homes, Monticello
$325,000
5 Beds ⋅ 2 Baths ⋅ 401408 MLS
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 drawers and cubbies. There’s also a 396 sf bonus room suitable for an office or workshop, plus 3 small outbuildings, one with power. Super location just 3 miles west of charming Monticello on beautiful U.S. 90; only 19 minutes from Tallahassee Amazon facility and Publix/Vineyard at I-10. Secluded due to natural vegetation, yet convenient to town.

2664 A W Washington Highway, Monticello
$175,000
3 Beds ⋅ 2 Baths ⋅ 401390 MLS
AFFORDABLE OLD MONTICELLO (FL) HOME. Spacious, good condition, move-in-ready. Convenient, easy walk to charming downtown. Recent basic repairs and renovations (roofing, electrical, etc). Old but very livable and 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 two-story storage shed. Spacious lot. This early 1900’s home is still very livable, very affordable, but with lots of potential for adding upgrades and value.

520 E High Street, Monticello
$435,000
3 Beds ⋅ 2 Baths ⋅ 401282 MLS
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 throughout. The spacious kitchen is the heart of the home, featuring quartz countertops, gas appliances, ample cabinetry, generous prep space, and a functional layout that flows seamlessly into the living and dining areas—perfect for entertaining or everyday living. The private owner’s suite offers a relaxing retreat, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to enjoy the fully fenced backyard, ideal for pets, children, gardening, or outdoor gatherings. A powered storage shed offers endless possibilities as a workshop, hobby space, or extra storage for tools and equipment. Additional highlights include energy-efficient newer construction, modern finishes, low-maintenance living, quality craftsmanship, and a desirable layout designed for today’s lifestyle. Whether you’re searching for a primary residence or your next investment, this exceptional home checks all the boxes with its modern amenities, functional design, and turnkey condition.

1680 Willow Road, Monticello
$429,000
3 Beds ⋅ 2 Baths ⋅ 401255 MLS
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 back porch with a propane hookup for grilling and generator hookup. This split plan offers a large primary suite with dual vanities, large walk in shower w/separate soaking tub and large walk in closet. Other features include LVP wood flooring, wood burning fireplace, tankless water heater, an indoor laundry room, ceiling fans, alarm and water softener. Convenient outdoor storage w/2 tool sheds- one w/ power hook up.

285 Mallard Lane, Monticello
$58,000
400968 MLS
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 maintaining the peace and privacy of a residential setting. With ample space for your custom home and outdoor living areas, this property combines neighborhood charm with practical convenience.

Spring Hollow Drive, Monticello
$200,000
3 Beds ⋅ 2 Baths ⋅ 400858 MLS
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.

1550 Tennessee Street, Monticello
$298,900
3 Beds ⋅ 2 Baths ⋅ 400806 MLS
Currently under construction. Interior pictures are from a previous model home. Approximately 60 days until completion. Home qualifies for USDA financing.

1070 Partridge Lane, Monticello
$319,900
3 Beds ⋅ 3 Baths ⋅ 400805 MLS
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 or study and laundry room. Large master bedroom with on-suite...double sinks and more granite. Walk-in closet and just off nook is optional "his" closet. Two spacious bedrooms and another large bathroom. This home also has a front porch and 2 car garage; is within walking distance to library, historic downtown and coffee house. Pictures are of a model home nearby.

300 Bowman Street, Monticello
$765,000
3 Beds ⋅ 3 Baths ⋅ 400801 MLS
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, offering endless possibilities for equestrian pursuits, a hobby farm, outdoor recreation, or simply a peaceful retreat from the pace of city life. Enjoy morning walks under the forest canopy, spend evenings watching deer and wild turkey from your porch, and observing stars under the dark skies. Yet despite its secluded setting, the property is conveniently located within easy reach of Tallahassee’s shopping, dining, medical facilities, universities, and airport, and a short drive to the historic town of Monticello. The beautifully maintained custom home is designed for both comfort and connection to the surrounding landscape, featuring a main-floor owner’s suite with a luxurious spa bath, energy-efficient Pella double-paned windows, a new roof, and high-speed internet. Outside, a swim spa, covered RV/farm equipment storage, small pond, and acreage for future expansion, barns, guest accommodations, gardens, or additional agricultural pursuits make this property as versatile as it is inviting. Outdoor enthusiasts will appreciate the close proximity to the Wacissa River, known for kayaking, fishing, and plentiful wildlife. With no HOA restrictions, you have the freedom to create the lifestyle you’ve imagined while experiencing the beauty and tranquility that only a truly exceptional North Florida estate can provide.

9901 GAMBLE Road, Monticello
$364,900
400229 MLS
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 immediate rental income, while the remaining 2 units are vacant and present an excellent value-add opportunity. Both vacant units are 1-bedroom, 1-bath units that need updating and repairs to become rent-ready, allowing the next owner to renovate and increase overall cash flow potential. Total Bedroom Count is 6 bedrooms and 5 bathrooms. Whether you are looking to expand your investment portfolio, renovate for increased returns, or capitalize on the growing demand for rental housing in Monticello, this property offers strong upside potential in a desirable in-town location.

480 S JEFFERSON Street Unit -, Monticello
$90,000
3 Beds ⋅ 1 Baths ⋅ 400131 MLS
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 3-bedroom floor plan with an updated kitchen and bathroom already in place. While the home has solid bones and endless potential, it will require significant renovations including electrical updates, roof replacement, plumbing updates, and HVAC installation. A rare opportunity to bring new life to a true piece of Monticello history! All dimensions are approximate.

340 S Waukeenah St, Monticello
$469,997
3 Beds ⋅ 2 Baths ⋅ 399958 MLS
MOVE IN READY!! Amazing new construction 3 bedroom 2 bathroom plus office. Luxurious master suite, Kitchen made of dreams, this is a must see!

51 Tarn Way, Monticello
$425,000
399902 MLS
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.

TBD E Cavallo Trail, Monticello
$1,175,000
3 Beds ⋅ 2 Baths ⋅ 399764 MLS
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 details throughout. Expansive wraparound covered slate porches invite you to relax and take in the peaceful surroundings. The oversized screened back porch and large patio overlook ponds and pecan grove, creating the perfect setting for gatherings or quiet evenings at home. Inside you will find exceptional craftsmanship including reclaimed pine floors, solid wood doors throughout, elegant crown molding, soaring vaulted ceilings, and a stunning stone gas fireplace. The spacious chef’s kitchen is designed for both everyday living and entertaining, featuring Corian countertops, wine cooler, abundant prep space, and a professional style 6 burner gas stove. Additional property features include a 3 car attached carport with storage area. There are 2 outbuildings with concrete floors, power, and water. The 48x36 barn includes a bedroom with full bath. Both buildings could be ideal for horses, kennels, hobbies or workshop space. There is also a 70x24 pole barn with water, great for equipment, RV, or hay storage. This unique property offers the perfect combination of luxury country living, functional acreage, and endless possibilities for equestrian use, recreation, farming, or multi-generational living. A rare opportunity to own a truly special estate in the heart of North Florida!

1590 Tyson Road, Monticello
$375,000
3 Beds ⋅ 3 Baths ⋅ 399744 MLS
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~

339 Silver Lake Rd., Monticello
$299,000
399642 MLS
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 subdivision opportunities. Buildable portions of the property may potentially be subdivided into 5-acre parcels, creating flexibility for investors, developers, or those seeking a large private tract with long-term upside. An 80-foot setback from wetlands applies. Buyer to verify all zoning regulations, permitted uses, subdivision potential, wetland boundaries, and development feasibility with the appropriate authorities. Enjoy the peaceful North Florida setting while still being conveniently located near Monticello and within driving distance of Tallahassee. Whether you are looking for an investment opportunity, recreational property, or future development site, this acreage offers tremendous potential.

BIG JOE Road, Monticello
$150,000
3 Beds ⋅ 1 Baths ⋅ 398842 MLS
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 ideal for relaxing mornings, outdoor gatherings, or simply enjoying North Florida’s laid-back lifestyle. Whether you're looking for a primary residence, a weekend escape, or an investment opportunity, this home presents incredible potential. Inside, you’ll find a comfortable layout with ample natural light and flexible living spaces ready to suit your needs. The generous lot provides plenty of room for gardening, recreation, or future enhancements. Located just a short drive from Tallahassee, Monticello is known for its rich history, friendly community, and scenic countryside. This property is a wonderful opportunity to enjoy the charm of rural living without sacrificing accessibility. Don’t miss your chance to own a slice of tranquility at 870 Shady Lane—where comfort, character, and opportunity come together.

870 Shady Lane, Monticello
$395,000
3 Beds ⋅ 2 Baths ⋅ 399473 MLS
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 electrical already in place- ideal for a barn, pole barn, or other future use. A unique basement/root cellar beneath the home provides additional storage or flexible space. Perfectly sized acreage to spread out and enjoy, ideally located between downtown Monticello and Thomasville, GA. A lovely setting offering a comfortable blend of space, function, and character.

1637 N Jefferson Highway, Monticello
$699,000
6 Beds ⋅ 4 Baths ⋅ 399129 MLS
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 waiting—its wide double porches still catching the breeze, its bones still strong, its story not yet finished. From the front porch, the gentle toll of the town bell drifts through the air, a quiet reminder of the rhythm of life just beyond the square. When its current stewards first stepped inside, they uncovered more than a home in need of repair. Tucked within its walls were photographs, letters, and fragments of lives once lived—small reminders that this home had always been something worth saving. What followed was not simply a renovation, but a full revival. With great care, the home was brought back to life—retaining its historic character while thoughtfully rebuilding nearly every major system. A new roof now shelters the structure, while updated electrical, plumbing, and HVAC systems provide modern reliability. Inside, a fully beautifully renovated kitchen and bathrooms offer the comforts of today without sacrificing the home’s original soul. Original heart pine floors remain throughout the main portion of the home. The kitchen and rear addition feature reclaimed oak flooring, carefully sourced from a late-1800s building in Chattanooga—an intentional detail that honors the home’s history at every turn. Spanning approximately 3,200 square feet, the home offers six bedrooms and three and a half baths, along with gracious living spaces, a formal dining room, and a central hallway plan that draws light and air from front to back. Tall ceilings, reaching nearly eleven feet, and decorative downstairs fireplaces lend a sense of warmth, scale, and quiet grandeur that only a home of this era can provide Outside, the signature double gallery porch stretches across both levels, inviting slow mornings, evening conversations, and the simple rhythm of small-town life—where a porch swing sways and rocking chairs settle into the day. A detached carport with an adjacent utility room adds everyday practicality without detracting from the home’s historic charm. This is not a restoration that erased the past. It is a home that has been carefully renewed—its history respected, its future secured. Set within one of North Florida’s most charming small towns, this home is just steps from the courthouse square—the heart of daily life in Monticello. Here, the pace is slower, neighbors greet one another by name, and a sense of community still quietly endures. The Mulberry House now proudly stands ready for its next chapter.

365 S MULBERRY Street, Monticello
$179,900
3 Beds ⋅ 1 Baths ⋅ 399392 MLS
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.

670 Poplar Street, Monticello
$227,900
3 Beds ⋅ 2 Baths ⋅ 399311 MLS
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.

120 Larry's Lane, Monticello