Refine Search
Map
Sort by
$175,000
403421 MLS
37 ACRES, AUCILLA RIVER HUNTING TRACT NEAR MONTICELLO. FL. Fronts on US 90 ½ mile west of the Aucilla River—perhaps the most prolific wildlife corridor in the county. The NE half of the property is an extension of the river’s drainway and borders SRWMD land on two sides. It’s a great wildlife habitat. The SW half along US 90 and Gramling Road is composed of a soil type (Plummer) suitable for planted pines or clearing for pasture. It has a decades-old stand of mature pine timber. There is a potential 1-acre homesite on the highway near Gramling Road that is out of the mapped river floodplain and should be suitable for a residential structure. Tie up this property NOW and be ready for the opening of gun season on Nov. 7.

Vacant E Washington Highway, Monticello
$899,000
3 Beds ⋅ 3 Baths ⋅ 403355 MLS
PRIVATE 41-ACRE ESTATE MINUTES FROM TALLAHASSEE - TRAILS, WILDLIFE, PASTURE & CUSTOM HOME 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
$95,000
403343 MLS
Vacant building lot; inside the city limits, city water and sewer are available, all high and dry; very nice neighborhood, no HOA.

450 Oconee Lane, Monticello
$279,000
3 Beds ⋅ 2 Baths ⋅ 402985 MLS
Step into the timeless charm of historic downtown Monticello, Florida, with this unique property offering nearly 2000 square feet of character and endless potential. Located within walking distance of downtown shopping, dining, and community events, this property is perfectly suited for residential living, commercial use, or a combination of both. Featuring beautiful original wood floors, soaring high ceilings, and architectural details rarely found in modern construction. , this historic gem is full of warmth and personality. A spacious covered front porch provides the perfect place to relax and enjoy the charm of one of North Florida's most picturesque downtown neighborhoods. While the property does need maintenance and updating, it presents an outstanding opportunity to restore and personalize a truly special building. Whether you're envisioning a distinctive home , professional office, boutique retail space, gallery, or other business, the flexible zoning and prime location make the possibilities endless. If you've been searching for a property with history, character, and an unbeatable location, this downtown Monticello treasure is ready for its next chapter.

380 N Jefferson Street, Monticello
$104,000
402857 MLS
Mobile-home-friendly property with a cleared homesite and an existing well, septic system, and electrical service already on the property. Seller financing is available. Conveniently located near I-10 and approximately 30 minutes from Tallahassee. Bring your home plans and enjoy a quiet country setting with room for animals, gardening, outdoor projects, and additional storage. Fence the property and create the private rural lifestyle you have been looking for while remaining close to shopping, dining, and other conveniences.

130 Sweetfield Road, Monticello
$949,000
3 Beds ⋅ 3 Baths ⋅ 402573 MLS
A rare opportunity to own a truly one-of-a-kind custom estate! Nestled on a private, fully fenced homesite overlooking 26 acres of golf course-like grounds, this 2021 custom-build home offers over 2,700 square feet of thoughtfully designed living space with breathtaking 270° views, including peaceful creek frontage. Built for both luxury and peace of mind, the home features hurricane shutters, a 250 mph-rated safe room, whole-home generator, soaring 10' and 16' ceilings, and extensive porcelain tile outdoor living areas, including an outdoor kitchen. Car enthusiasts, hobbyists, and RV owners will appreciate the impressive 1,500 sq. ft. insulated and cooled 4-car garage/workshop with water, additional equipment building, and 65-amp RV hookup with dedicated septic. Private, secure, and conveniently located, this exceptional property delivers the perfect blend of comfort, functionality and unforgettable views.

307 Crabapple Drive, Monticello
$125,000
402606 MLS
Back on the market - Discover the perfect place to build your dream home on this beautiful nearly 6-acre parcel! Enjoy the peace and privacy of country living with the convenience of being just minutes from the interstate and a short drive to Tallahassee. With plenty of room for your custom home, workshop, gardens, or recreational space, the possibilities are endless! Whether you’re looking to create your forever home or invest in land with an ideal location, this is an opportunity you won’t want to miss. Come experience the freedom and potential this exceptional property has to offer!

Eastwood Road, Monticello
$235,000
3 Beds ⋅ 1 Baths ⋅ 402594 MLS
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 fireplace in the living room and primary bedroom, soaring ceilings, and charming details throughout. Situated on a spacious .23 acre in-town lot, the property offers convenient access to Monticello's historic downtown, where you'll enjoy locally owned shops, dining, and community events. The spacious backyard is fully fenced, with a large deck, 2-car garage/workshop, a chicken coop, and plenty of room for the kids and pets to play. Whether you're looking to restore a piece of Jefferson County history or simply appreciate the quality craftsmanship and sturdiness of a home that was built to last, this home presents a wonderful opportunity to make it your own.

810 E Dogwood Street, Monticello
$59,500
402393 MLS
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.

Lot 25 E Washington Street, Monticello
$49,500
402390 MLS
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.

Lot 14 E Washington Street, Monticello
$49,500
402391 MLS
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 15 & 20 directly behind it totaling .45 Acre.

Lot 15 E Washington Street, Monticello
$49,500
402392 MLS
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.

Lot 16 E Washington Street, Monticello
$59,500
402389 MLS
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.

Lot 13 E Washington Street, Monticello
$85,000
402387 MLS
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.

Lot 11 E Washington Street, Monticello
$59,500
402388 MLS
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.

Lot 12 E Washington Street, Monticello
$325,000
4 Beds ⋅ 2 Baths ⋅ 402384 MLS
Seller is offering $5000 toward closing costs! Charming 2022 Mobile Home on 5 Peaceful Acres A rare blend of modern comfort and wide-open space, this 2022 mobile home sits on 5+ acres—perfect for anyone craving privacy, freedom, and room to grow. Whether you dream of a hobby farm, a quiet country retreat, or simply a place with no close neighbors, this property delivers. Embrace freedom of country living with the convenience of a modern home. Wake up to quiet mornings and build the lifestyle you’ve always wanted. Convenient to Tallahassee, Monticello, Perry and Thomasville. This home features a bright, open-concept living area with contemporary finishes. Enjoy your spacious kitchen with ample cabinetry, large pantry and modern appliances. Comfortable bedrooms and well-appointed bathrooms complete this move in ready home. Underground utilities include community water, electric and Century Link WiFi! You'll have plenty of space for gardens, animals, workshops and future expansion!

947 Piney Woods Road, Monticello
$1,100,000
3 Beds ⋅ 3 Baths ⋅ 402379 MLS
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 room with a wood-burning fireplace, beautiful sunroom and a spacious master suite. This home is equipped with a tankless water heater and a whole-house generator. Step outside to enjoy true outdoor living perfect for entertaining family and friends in the fully equipped outdoor kitchen or unwind year-round on the screened porch featuring a wood-burning fireplace. Whether you’re enjoying quiet mornings or hosting gatherings, this home was designed to embrace the beauty of its natural setting. The property also offers a detached three-car garage complete with a workshop, a pole barn, and ample room for equipment, recreational vehicles, or hobbies. With nearly 30 acres of open space, there’s endless potential for horses, farming, recreation, or simply enjoying the privacy and serenity of your own land. If you’ve been dreaming of a country estate with room to roam, spectacular views, and exceptional amenities, this one-of-a-kind property is ready to welcome you home.

458 Watermill Road, Monticello
$350,500
3 Beds ⋅ 2 Baths ⋅ 402229 MLS
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.

1565 Sweetbay Court, Monticello
$424,900
4 Beds ⋅ 3 Baths ⋅ 402136 MLS
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 beautiful back yard!! Come see all this home has to offer today!!

855 S Waukeenah Street, 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
$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
$429,000
3 Beds ⋅ 2 Baths ⋅ 401255 MLS
*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
$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
$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
$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
$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