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$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
$450,000
3 Beds ⋅ 2 Baths ⋅ 399265 MLS
Custom home on 4.29 private acres~split bedroom plan~separate dining room~rocking chair front porch~screened porch overlooking wooded backyard~fireplace~upstairs room could be office or playroom~huge 40x40 workshop~FIRST TIME ON THE MARKET

254 Woodland Drive, Monticello
$199,000
399248 MLS
Fronting on Hwy-90 this high elevation lot is lightly wooded. Some restrictions apply.

TBD W Washington, Monticello
$259,900
3 Beds ⋅ 2 Baths ⋅ 399174 MLS
Nestled on 5.5 peaceful, private acres, this charming 3-bedroom, 2-bath home offers the perfect blend of space, comfort, and tranquility. Step inside to an open floor plan designed for both everyday living and effortless entertaining, with a seamless flow between the living, dining, and kitchen areas. The spacious primary suite is a true retreat, featuring a large en-suite bathroom complete with a beautifully tiled shower. Two additional bedrooms provide flexibility for family, guests, or a home office. Outside, enjoy the privacy and possibilities that come with 5.5 acres—ideal for relaxing, gardening, or simply taking in the quiet surroundings. Whether you’re looking for a peaceful homestead or a place to unwind, this property delivers. Don’t miss your chance to own your own slice of country living

1164 Oaklands Plantation Road, Monticello
$398,900
3 Beds ⋅ 3 Baths ⋅ 399132 MLS
For generations, this beautifully maintained, one-family owned brick home has been a place where holidays were celebrated, children were raised, and life's everyday moments became treasured memories. Today, with only one family member remaining, the home has simply become more space than one person needs. Rather than seeing it sit too quietly, she hopes to pass it on to another family who will fill its rooms with laughter, traditions, and memories of their own. It is a home that has been deeply loved, carefully preserved, and is ready for its next chapter. Situated on 1.5 peaceful acres along North Jefferson Highway, this neo-classic 3-bedroom, 2 and a 1/2 bath home offers 3127 square feet of comfortable living space. A 24x10 screened porch invites you to slow down and enjoy quiet mornings, evening conversations, and security of nearby neighbors. Outside a concrete driveway loops around all the way to the rear, and open green space creates a setting where children can run, family pets can roam, gardens can flourish, and memories can be made. The detached workshop provides valuable storage with a chicken coop and multi use farm stall behind that. An entertainment deck 24x24 is built around "The Magnolia" and a bonus room that has a half bath is heated and cooled is waiting for your ideas to finish and decorate. Ideally located between historic downtown Monticello and Thomasville, Georgia, this property offers the rare combination of privacy, convenience, and room to grow. Whether you're gathering multiple generations under one roof, creating your forever home, or simply looking for space to breathe, this is more than a house—it's an opportunity to continue a legacy of love, laughter, and cherished memories for years to come.

1628 N Jefferson Highway, Monticello
$439,900
3 Beds ⋅ 2 Baths ⋅ 399057 MLS
Welcome to this exquisite soon to be finished new construction home in the quiet and quaint Crooked Creek Subdivision, conveniently located just off of 90E and only minutes away from the historic charm of Downtown Monticello. With easy access for commuting to Tallahassee or Thomasville, this location offers the perfect balance of peaceful living and convenient amenities. Immerse yourself in the local community, with nearby parks, charming shops, and a wealth of recreational opportunities right at your fingertips. Whether you're exploring the picturesque surroundings or enjoying the vintage shopping experiences, this location truly has it all. Step inside this stunning home and be captivated by the thoughtful builder specs and attention to detail. Spanning 1883 square feet, this spacious home features 3 bedrooms, with a versatile 4th room that can be used as an office or bonus room, accommodating all your lifestyle needs. The 2 full baths provide convenience and comfort, while the tray ceiling in the living room adds an elegant touch to the space. Luxury vinyl plank flooring throughout the home ensures durability and easy maintenance, while the solid wood cabinets and quartz countertops in the kitchen create a stylish and functional culinary haven. Admire the unique barn door leading to the 4th room, adding a touch of charm and versatility to the floor plan. The separate laundry and mudroom offer convenience and organization, while the electric fireplace adds warmth and ambiance to the living area. With a 2-car garage, you'll have plenty of space for parking and storage. The split floor plan and open concept layout make this home ideal for both entertaining and everyday living, providing a seamless flow between rooms and ample privacy for all. Don't miss the opportunity to make this new construction home yours, where comfort, style, and convenience blend seamlessly. Experience the beauty and craftsmanship of this remarkable property in the desirable Crooked Creek Subdivision. Expected completion date July 2026. Buyer to verify all measurements.

110 Crooked Creek Lane, Monticello
$2,735,850
7 Beds ⋅ 7 Baths ⋅ 398839 MLS
Welcome to a rare opportunity to own a true estate property where space, craftsmanship, and privacy come together on 70 beautiful acres. Only 15 minutes to Whole foods & trader Joe's This impressive 7-bedroom, 5 full bath, 2 half bath two-story home offers a thoughtfully designed layout ideal for both everyday living and entertaining on a grand scale. Upstairs features 4 bedrooms and 2 full baths, while the downstairs includes 2 bedrooms, 2.5 baths, a formal dining room, and a cozy private study—perfect for working from home or quiet retreat. At the heart of the home, a massive kitchen opens seamlessly into the living room, creating an inviting open floor plan that flows effortlessly to the outdoor living space. Step outside to your outdoor kitchen overlooking a stunning paver pool deck, hot tub, and resort-style setting built for gatherings and relaxation. Just steps away, the pool house offers even more flexibility with a loft and full bath upstairs. Downstairs, you’ll find remarkable character and craftsmanship featuring herringbone brick floors, pecky cypress ceilings, a custom bar area with half bath, and a discreet hidden gun room that adds a unique touch to this one-of-a-kind property. Whether you’re hosting guests, enjoying peaceful country living, or looking for a multi-functional estate with room to roam, this property delivers unmatched charm, privacy, and versatility. A property like this is more than a home—it’s a lifestyle. NEW 2025 Roof/HVAC

305 old lloyd Road, Monticello
$69,900
398743 MLS
Owner Financing available with 20% down. Motivated Seller! Unique shaped parcel located in a serene rural area—perfect for building, recreation, or investment

XXX Hopson Road, Monticello
$379,000
3 Beds ⋅ 2 Baths ⋅ 398555 MLS
Tucked away on 5 private acres down a quiet, wooded road, this brick home offers 2,280 square feet with a split floor plan featuring 3 bedrooms and 2 baths, providing both space and functionality. New HVAC June 2026 with 10 year parts warranty, plus new roof November 2025, Well 2022, and septic drain field replaced 2016. Inside, you’ll find a cozy fireplace and a bright sunroom that brings the outdoors in, while the solid layout offers plenty of opportunity to make it your own. A huge laundry/utility room just off the attached garage adds extra convenience and flexibility for amazing storage or workspace needs. The property is filled with mature trees, lush greenery, and blooming flowers that create a vibrant, natural setting. It also includes a large detached garage/workshop with power, concrete floor and a lean-to along two sides, perfect for projects, equipment, or hobbies, plus a small Green House. Conveniently located in Monticello with easy access to US-90, you’re just a short drive to Tallahassee while enjoying the privacy of country living. Measurements are approximate.

1012 S Main Avenue, Monticello
$679,900
4 Beds ⋅ 3 Baths ⋅ 398548 MLS
NOW INCLUDES ADDITIONAL LOT!! Discover this stunning 2,600+ sqft home built in 2021, offering the perfect blend of quiet country living and modern convenience. Adjoinging additional lot can also be purchased! Features include: 4 spacious bedrooms and 3 full bathrooms 2 master bedrooms located downstairs Dedicated office/bonus room – ideal for work or hobbies Modern kitchen and open living spaces Attached 2-car garage Just minutes from downtown, providing a quick and easy commute Enjoy serene country surroundings with the benefits of a new, move-in-ready home. Don’t miss out on this incredible opportunity!

140 SHUMARD Court, Monticello
$754,000
3 Beds ⋅ 3 Baths ⋅ 398493 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
$1,950,000
7 Beds ⋅ 7 Baths ⋅ 398259 MLS
Welcome to a rare opportunity to own a true estate property where space, craftsmanship, and privacy come together on 18 beautiful acres. This impressive 7-bedroom, 5 full bath, 2 half bath two-story home offers a thoughtfully designed layout ideal for both everyday living and entertaining on a grand scale. Upstairs features 4 bedrooms and 2 full baths, while the downstairs includes 2 bedrooms, 2.5 baths, a formal dining room, and a cozy private study—perfect for working from home or quiet retreat. At the heart of the home, a massive kitchen opens seamlessly into the living room, creating an inviting open floor plan that flows effortlessly to the outdoor living space. Step outside to your outdoor kitchen overlooking a stunning paver pool deck, hot tub, and resort-style setting built for gatherings and relaxation. Just steps away, the pool house offers even more flexibility with a loft and full bath upstairs. Downstairs, you’ll find remarkable character and craftsmanship featuring herringbone brick floors, pecky cypress ceilings, a custom bar area with half bath, and a discreet hidden gun room that adds a unique touch to this one-of-a-kind property. Whether you’re hosting guests, enjoying peaceful country living, or looking for a multi-functional estate with room to roam, this property delivers unmatched charm, privacy, and versatility. A property like this is more than a home—it’s a lifestyle. NEW 2025 Roof/HVAC

305 Old Lloyd Road, Monticello
$599,000
7 Beds ⋅ 7 Baths ⋅ 398052 MLS
Introducing a stunning 1.2 acre estate in the heart of Historic Downtown Monticello. The Simon-Ridgeway home was built in 1888 and boasts a generous 4,500 sq ft of living space and features 7 spacious bedrooms, 5 of which come with its own en-suite bathroom for ultimate privacy and convenience. City granted BNB status - making this perfect for an owner/occupier wanting to work from home and enjoy small town life! You'll fall in love with the intricately designed hardwood floors that flow throughout the home, perfectly complementing the timeless charm. The newly remodeled kitchen is a chef's dream, blending modern amenities with classic elegance, from the large farmhouse sink to the new Stainless Steel appliances. Too many updates to list- but some include a new roof, AC's, bathrooms, and kitchen, just to name a few! Enjoy the slower pace of life from the huge, Double-Story Gothic Revival front porches or the large back deck. Other outdoor features include: Large Detached Double garage with washer dryer hookups; and 2 small houses in the backyard for multigenerational living, Airbnb income or extra space for guests! Don't miss your chance to own a piece of history that offers both luxury and comfort. Schedule a showing today! Creative Financing available.

625 E WASHINGTON Street, Monticello
$510,000
4 Beds ⋅ 3 Baths ⋅ 397236 MLS
Exceptionally maintained , this turn key 2022 farmhouse-style home is located in the sought after Crooked Creek area.Seller is motivated! This home is ready for immediate occupancy and includes whole house generator still under warranty. This spacious 2134 sq ft home features 4 bedrooms and 2.5 baths on a generous .85 acre lot, ideally situated on a quiet cul-de-sac on the west side of Monticello. The open-concept layout offers elegant coffered ceilings crown molding and a cozy gas fireplace with built-in shelving in the living room- perfect for relaxing or entertaining. Primary suite offers an extra large bath with large walk- in shower and slipper tub. The light -filled interior creates warm and inviting atmosphere throughout the home. Enjoy peaceful living just on the edge of town, with convenient access to state capital, Tallahassee. A perfect blend of modern comfort, style, and location in a quiet neighborhood setting.

121 Shumard Court, Monticello
$349,000
3 Beds ⋅ 2 Baths ⋅ 397112 MLS
Rare Find! Country Living on 1 Acre-No HOA! Enjoy peaceful country living on a full 1-acre property with no HOA restrictions. This spacious 1774 square foot home features 3 bedrooms and 2 bathrooms with a bright open concept layout. The home features LVP flooring throughout, fresh interior paint in main living area, and a new roof in 2023 for added piece of mind. The primary suite includes a beautifully tiled walk-in shower in master bath. Shows like a newer home. Step outside and enjoy the freedom of country life-ideal for gardening, micro-farming, and raising chickens or goats. Conveniently located with easy access to Tallahassee. Don't miss this opportunity to own your own slice of the country!

8156 Waukeenah Highway, Monticello
$499,000
5 Beds ⋅ 2 Baths ⋅ 397098 MLS
Charming Cape Cod-style home tucked away on 5 acres just minutes to downtown Monticello. This one owner home has been lovingly maintained and reflects years of care and pride of ownership. With over 2200 square feet of living space, the home offers a comfortable layout. The main floor features three bedrooms, one bath, a welcoming living room with a gas fireplace, dining area, kitchen and a convenient laundry room. The second floor includes two additional bedrooms, a full bath, and a lovely reading /library room could also serve as a playroom or flexible living space. Extra attic storage provides plenty of room for seasonal items and additional storage needs. Relax on the back enclosed porch while enjoying the beautiful views of the surrounding trees and well kept grounds. Additional features include a workshop/storage/mancave for hobbies or projects, plus and extra carport/tractor shed with additional enclosed space perfect for a potting shed and garden tools This well maintained property offers warmth, character, and peaceful surroundings . Newer roof and windows and exterior paint!

398 Tecumseh Road, Monticello
$135,000
397041 MLS
Looking for privacy, this 10 acres provides an ideal homesite with some clearing for your homesite completed. The balance of the land is woorded with a mix of hardwoords and pines. Some of the land is in welands/flood which provides a nice buffer for privacy and a wildlife habitat. There is a well/pump (no tank), an older septic, and power pole. 15 ft easement leads to the property. Located just a few minutes north of Monticello.

576 Cox Road, Monticello
$775,000
4 Beds ⋅ 3 Baths ⋅ 396927 MLS
New Construction. Images are renderings. 4-bedroom, 3-bath home coming soon in Tally Hills Estates. Construction has started on this beautifully designed, new construction home set on over 5 acres.

693 Tally Hills Drive, Monticello
$239,000
3 Beds ⋅ 1 Baths ⋅ 396818 MLS
Very convenient location in the heart of Monticello. Excellent condition. Very good condition, new roof, new windows, newer flooring throughout. 10X12 storage shed.

220 Eaton Street, Monticello
$275,000
396434 MLS
OWN A PIECE OF HISTORIC DOWNTOWN MONTICELLO! Opportunity awaits in the heart of Historic Downtown Monticello! This versatile commercial space is currently operating as a retail shop and offers exceptional flexibility for a variety of business uses. Large front-facing windows provide abundant natural light and excellent visibility, overlooking the vibrant sidewalk area- perfect for attracting foot traffic and showcasing your business. Inside you will find spacious retail floor area, full kitchen, one bath with additional plumbing already in place for additional bath. Ample storage space leading to your own back entrance. Whether you envision a boutique, cafe, studio or specialty shop, this property offers the infrastructure and location to bring your concept to life.

185 E Dogwood Street, Monticello
$429,900
3 Beds ⋅ 2 Baths ⋅ 396075 MLS
Welcome to this beautifully custom-built 3 bedroom, 2 bath home completed in 2024 and located in the desirable Hemings Pond Subdivision. Offering the perfect blend of modern construction and thoughtful upgrades, this move-in ready showcases luxury vinyl plank flooring, upgraded light fixtures, premium countertops, and elegant bath fixtures. Owner selected custom enhancements elevate the space even further, including wooden plantation shutters, remote-control roller shades in all the bedrooms, a shadow box privacy fence enclosing the backyard, and a full irrigation system for easy outdoor maintenance. Also included in the owner upgrades is a covered patio for outdoor entertaining. Situated just outside the city limits, this home provides the comfort of new construction with added privacy and convenience. Don't miss your chance to own this stylish, turnkey property in a growing community! Seller offering $10,000 in closing cost with acceptable offer!

107 S TARN Way, Monticello
$1,325,000
5 Beds ⋅ 5 Baths ⋅ 395876 MLS
Welcome to a rare North Florida estate just minutes from Tallahassee—where luxury, land, and lifestyle come together. 221 Kiley Road is situated on expansive acreage in Monticello, and this private retreat offers the perfect blend of seclusion and convenience, located just a short drive from the heart of Tallahassee. For buyers seeking space, privacy, and versatility without sacrificing proximity to town, this property delivers. This 5-bedroom, 3.5-bathroom estate is a true masterpiece, gracefully set on 5 private acres and complemented by a beautiful pool house with an additional bathroom. An additional adjoining 5-acre parcel is also available, offering the rare opportunity to expand your privacy, create a multi-generational compound, or enhance the estate even further. Set on picturesque rolling land, this one-of-a-kind property features your own private vineyard, offering a breathtaking and romantic backdrop for everyday living and entertaining. Imagine sunset dinners overlooking the vines, peaceful morning walks through the rows, or simply enjoying the beauty and serenity that only a setting like this can provide. Equestrian enthusiasts will appreciate the well-appointed horse stable, open pasture, and room to ride, creating the perfect environment for both horses and riders to thrive. Thoughtfully designed for function and beauty, the grounds invite you to embrace true North Florida country living. At the heart of the property sits an impressive residence offering approximately 5,500 square feet of living space, ideal for large households, multi-generational living, or those who love to entertain. The thoughtfully designed layout features expansive living areas filled with natural light, a spacious kitchen with abundant cabinetry and workspace, and oversized bedrooms that serve as peaceful private retreats. Multiple flex spaces provide endless possibilities for home offices, media rooms, fitness areas, hobby spaces, or additional guest accommodations — tailored to fit your lifestyle. Step outside to your private pool oasis, perfect for relaxing afternoons or hosting unforgettable gatherings. A separate guest house offers comfortable accommodations for visitors, extended family, or a private retreat, adding flexibility and value to this exceptional estate. From vineyard evenings and horseback mornings to poolside afternoons, this Tallahassee luxury home alternative is more than a home — it’s a lifestyle. Offering space, versatility, natural beauty, and privacy while still convenient to downtown Monticello, schools, shopping, and dining, this is a truly rare opportunity to own a remarkable property where memories are made for generations.

221 KILEY Drive, Monticello