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$564,900
3 Beds ⋅ 2 Baths ⋅ 405271 MLS
Welcome to this beautiful one-owner home in highly sought-after Crooked Creek, located just at the edge of town in Monticello, Florida. Built in 2021 and offering over 2,000 square of living space, this meticulously maintained home is truly turnkey. Set on an impressive.76-acre lot, the property offers exceptioanl privacy and outdoor living. The beautifully fenced backyard features a sparkling in-ground pool with fountain., creating the perfect setting for relaxing, entertaining, and enjoying Florida's beautiful weather. Inside, the home offers a desirable open floor plan with plenty of natural light and a warm, inviting feel. One of the home's standout features is the lovely sunroom overlooking the pool and backyard, providing a peaceful space to enjoy your morning coffee or unwind at the end of the day. PROPERTY HIGHLIGHTS: Whole House Generator, Pool, Fenced Backyard. ADJOINING .70 ACRE LOT AVAILABLE FOR PURCHASE.

205 Crooked Creek Lane, Monticello

$175,000
2 Beds ⋅ 1 Baths ⋅ 405104 MLS
If you are looking for your opportunity, this home's for you! This 1950's bungalow is within reach for all. Whether a first time buyer, down-sizer, or investor, this home has ample opportunity for all! At a price where designer re-dos and renovations are possible, anyone can can make this dream come true! The huge addition (500+ sqft) off the rear of the home offers ample square footage that could possibly be reconfigured to a new owner's desires. The original home features a two bedroom one bath floor plan. The kitchen is sandwiched between two large living areas making opportunities for renovations and modernization ideal. With a third acre that's fully fenced, existing dog kennel, and a true garage, this property has built in bonuses in addition to the stellar location just moments away from Monticello's town center, access to I-10 and Hwy90 for easy commutes. Monticello is still known for its downtown charm and community events and connectedness. Just check out the chamber's facebook page! :D In addition to the Ecological Park and Legion right across the street, the house is minutes from town square where you can enjoy entertainment at Old Monticello Opera House, Vintage Stores, Restaurants. And if you wanted to, the Aldi and DG Market are walking distance to the home! So if you are looking for true potential not just in making a home, but making and enjoying community, see what 1060 S Water Street has to offer in charming Monticello, Florida!

1060 S Water Street, Monticello

$895,000
3 Beds ⋅ 3 Baths ⋅ 404823 MLS
Tucked away on 10.87 private acres behind its own gated entrance in the sought-after Rainey Run community, this custom-built home offers the perfect balance of quality craftsmanship, modern comfort, and peaceful country living. Built by Hannon Construction in 2023, the 3-bedroom, 2.5-bath home spans 2,412 square feet and was thoughtfully designed with timeless finishes and functional spaces throughout. At the heart of the home, the kitchen features a premium ILVE range and cooktop, Electrolux refrigerator, freezer, and dishwasher, custom cabinetry by Carroll's Cabinets & Countertops of Thomasville, quartz countertops, and a spacious walk-in pantry. Custom and antique lighting adds warmth and character, while the laundry room includes a folding station or convenient drop zone with storage. The open living area is centered around a gas fireplace, and large E-rated energy-efficient windows fill the home with natural light. Storage was thoughtfully incorporated throughout the home, including an impressive 52-foot by 8-foot walk-up attic with double flooring and a dedicated storage closet pre-wired for future security technology. Just off the laundry room, you'll find a brick patio and a half bath that was thoughtfully designed to serve as a future pool bath, making it easy to expand your outdoor living space if desired. Outside, a Morton building with electricity and water provides plenty of space for a workshop, equipment, hobbies, or storage. The home also features a whole-house generator and a Rinnai tankless water heater for added convenience and peace of mind. In addition to the community gate, the property has its own private gated entrance, offering an added sense of privacy and easy access. Enjoy the peace and privacy of country living without giving up convenience. Ideally located just minutes from downtown Monticello and a short drive to Tallahassee, this home offers the best of both worlds. If you've been looking for newer construction on acreage without sacrificing quality, convenience, or location, this home is one that truly stands out. Every detail has already been thoughtfully considered, creating a property that's as functional as it is beautiful.

4216 W Washington Highway, Monticello

$700,000
3 Beds ⋅ 3 Baths ⋅ 404453 MLS
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, rubber mats, LED lights and stall fans installed recently, a large tack room and wash racks. This an ideal setup for anyone looking for a functional, turn-key horse property. The home itself is in excellent condition and thoughtfully laid out, with a spacious living room anchored by a large fireplace, a kitchen with bar seating, breakfast nook and new appliances and a separate formal dining room. Every room has a beautiful view of the farm surrounding it. Wood floors run throughout the main living areas, adding warmth and character, while all bedrooms and office are tucked upstairs for a quiet retreat. A new 2024 roof and fully repainted interior, adds peace of mind. Enjoy sweeping views of the surrounding countryside and a true sense of privacy, all while being conveniently located to both Tallahassee and Thomasville. This is a property you don't want to miss!

660 Whispering Hills Road, Monticello

$695,000
5 Beds ⋅ 3 Baths ⋅ 403842 MLS
Just 3 miles south of Monticello, FL and only 2.5 miles from I-10, this 10.45 acre working homestead has been thoughtfully set up for country living, livestock and extended family. The 3,536 sq. ft. home features 4 bedrooms/2 baths in the main house (with the set up for an additional bath upstairs) master is conveniently located downstairs with two walk-in closets, private access, plenty of lighting and a huge newly renovated bathroom, whirlpool tub in spare bath, high ceilings in the living area with a wood burning fireplace, bright beautiful kitchen with corrian counter tops, new dishwasher, new stovetop and french doors leading to the best views of the back of the property. This exceptional property also includes a private one bedroom, one bath mother in law suite with its own private entrance, connected to the main home by an enclosed breezeway (initially set up for a small hair salon business). The suite offers a large living area, new step in shower, new refrigerator, kitchen sink, microwave even their own back porch! Ideal for a parent, grown child, guests or simply someone who needs a little independence while staying close to family. Outside is where the property really earns the name farmstead. Six fenced paddocks (Bekaret 4ft high tensile sheep and goat fence) along with "no climb fencing in the back yard for the dogs. Pines, crape myrtles, beautiful live oaks run on the back side of the house providing ample shade for livestock. There is a three bay pole barn (25x30), equipment shed/potting house (15x50), additional equipment barn (25x60), chicken coop (10x16), peach trees and blueberry bushes, plus plenty of room to continue growing, gardening and raising animals. New pitcher pump well provides access to water even when the power is out with the option to hook up to community water. Water is ran to EVERY pasture clear up to the main road! The property is gated with Ghost Controls, fenced and has excellent frontage on Waukeenah Highway. Best of all, there is no HOA and no deed restrictions to tell you how to use your own 10.45 acres. This insn't just a house with acreage. It's an established country homestead with the infrastructure already in place and close enough to town for conveniences. Most everything on the property is negotiable...including tractor with attachments, chickens, as well as other equipment and furnishings.

2247 Waukeenah Hwy, 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

$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

$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

$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

$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

$1,200,000
4 Beds ⋅ 3 Baths ⋅ 402221 MLS
**Some Photos are Virtually Enhanced** Experience luxury living in the prestigious gated community of Rainey Run. This is where privacy, nature, and convenience come together on 10 breathtaking acres. Surrounded by towering hardwoods and abundant wildlife, this remarkable property offers a convenient peaceful retreat. Built in 2020, this custom home showcases quality craftsmanship with a highly thought out design. Greeted by a beautifully crafted foyer, you immediately feel at home from the moment you walk through the door. The spacious kitchen opens to the living room offering the perfect entertainment design. The spacious floor plan is designed for both comfortable everyday living and effortless entertaining. Allowing privacy with its split floor plan, the primary bedroom features his and her walking closets with a spa like bathroom escape. 3 bedroom with office (or 4th bedroom) and bonus room (could be used as another bedroom). Step outside and enjoy your own private sanctuary, where deer, turkey, and other native wildlife are frequent visitors. A large workshop with electricity and water provides endless opportunities for hobbies or equipment storage. Located behind the gates of one of Jefferson County’s most desirable communities, Rainey Run offers the peaceful escape from the city with the convenience of Tallahassee being only a few minutes away. Schedule your private showing today, this home has so much more to share! Built by Saxon Hannon, of Hannon Construction. Buyers to verify all dimensions and measurements.

974 Rainey Run, 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

$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

$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

$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