Welcome to 221 Kiley Road in Monticello, Florida — a rare estate where vineyard charm, equestrian living, and exceptional space come together to create an unforgettable lifestyle. 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, 221 Kiley Road 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.
Amazing Investment Opportunity as a Large family home, multi-generational property or Cash flowing investment! Own your piece of history and enjoy some great cash flow in this beautiful Downton Monticello Home. Built in 1888 and almost 4500 SF in the main house with 9 bedrooms, 7 bathrooms and common areas for the tenants. Currently set up with tenants as a BNB type property with longer term rent. Too many improvements to list but here are a few: New roof 2024, new HVAC 2022 and mini splits, New kitchen and bathrooms 2022, 2 Tankless Hot water heaters and many more improvements! Property also includes two other houses in the backyard; a 2 bed, 1 bath and a 1 bed, 1 bath home. Separate oversized garage with half bath and W/D hookups behind main house. Large 1.2 acre property right in the heart of downtown- walk anywhere in Monticello! Fully rented it brings in $11,000 a month gross!
Perfect brick family home right downtown! Walk to the veggie stand across the street and all the Monticello shops! Renovated 4-bed, 2-bath home. New roof!! New Custom Kitchen cabinets, granite counters, and SS Appliance package perfect for you home chefs. The open-plan kitchen opens directly into the dining and living room. New Flooring, Paint, Light fixtures, Custom closets and bookcases throughout, and a fun hidden door from the front bedroom to the hall bathroom! Brand New Large capacity LG Laundry Tower included too! The lot is a great size as well- running from Washington to Palmer Mill Rd- and even has a second driveway from that road. Backyard is fully fenced and has a large, older shop with electric and a smaller shed at the back of the yard. You can't miss this one!
Custom hurricane-resistant/efficiency home on 3.6 private acres in a gated equestrian community, just 17 miles east of Tallahassee and 1 mile to I-10 (Exit 217). Built in 2013, this 2,112 sq ft home features 4 bedrooms, 3 full baths, and 9’ ceilings throughout. Constructed with Nudura ICF 12” insulated concrete exterior walls for superior strength, energy efficiency, and sound insulation. All-electric home with avg. electric bill approx. $100/month. New roof 2024. Interior highlights include large closets, walk-in shower, sun tunnels in 2 baths and laundry, ultra-quiet Panasonic vent fans, and stand-up attic with full walkway and lighting. Oversized garage with three 8’ doors, built-in shelving, Deese Elite floor coating, water tank for freeze protection, and generator. Exterior features include paved 12’ x 240’ driveway, automated underground irrigation to fruit trees, outdoor sink, underground water line, floodlights, motion sensors, camera and security systems. Private well and septic. Community offers paved private roads, 1.7-mile walking loop, and nearby horse facilities.
Welcome to this stunning new construction masterpiece, meticulously designed and built by the esteemed Kasdorf Homes, LLC. This craftsman beauty is awaiting its first owners and will be ready for occupancy by the beginning of May. Spanning an impressive 2134 square feet, this home offers a spacious and open concept floor plan, perfect for modern living. The split floor plan provides privacy and convenience, while the huge 4.25 acre lot offers ample space and tranquility. Nestled in a Hiawatha Farms gated community this property provides a secluded feel while still being conveniently close to I-10. You'll enjoy the benefits of a friendly neighborhood association. Step inside and be greeted by the inviting atmosphere of this 3-bedroom home. Additionally, an office or bonus room with a barn door entrance provides flexibility to suit your needs. The 2.5 bathrooms feature modern tile and luxurious finishes. The heart of the home is the living room, boasting a electric fireplace with a shiplap accent wall that adds warmth and character. The tray ceiling create an elegant and unique touch. The kitchen is a chef's dream, with quartz countertops, a large island offering plenty of storage, and sleek matte black finishes that exude contemporary style. Throughout the main living spaces and all bedrooms, you'll find durable and stylish luxury vinyl plank flooring, providing both beauty and functionality. The meticulous attention to detail extends to every aspect of this home. Please note that the pictures provided are from a previous build with the same floor plan, offering a glimpse into the quality and craftsmanship that will be present in your new home. Don't miss this extraordinary opportunity to own a brand-new, move-in ready home in a secluded yet convenient location. Schedule a private showing and explore the endless possibilities that await you in this exceptional new construction build.
Secluded 56.37 Acres with Metal Building & Living Quarters -Western Jefferson County. This property offers privacy, versatility and room to build or expand. The land features a 2880 sq ft heavy-gauged metal building designed for both residential and workshop use. Second floor includes 1200 sf of living space currently unfinished featuring two bedrooms, kitchen and living area and one bath. A freight/lift system provides easy transport of materials and equipment to the second floor. Ground level consists of a spacious workshop/hobby area ideal for storage, projects or business use along with an attached carport for parking or equipment storage. This property is well suited for a private retreat, recreational use, homestead or a buyer seeking land with and existing structure ready for customization. There is approximately 15 acres of good usable land with the remaining land in flood zone/wetlands.
Enjoy this quaint, well kept 2/2 mobile home on 1.5 acres of usable land. Brand new flooring and 2 brand new water heaters. This homestead is perfect for a small family, or retired couple who want to be in nature, without sacrificing community. Convenient to both I-10 and Monticello, this home has lots to offer. Spend hours on the screened porch watching the birds and wildlife. Work in the large on-site shop. Float in the above ground pool in the back yard. Park your RV on the RV pad in the back yard. Enjoy the serenity of the wooded surroundings, while utilizing the fenced back yard to keep your dogs or animals nearby.
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!!
Picturesque Setting. Beautiful home on a hill surrounded by fenced and cross fenced pasture with wooded areas with beautiful Oaks! Sit on your rocking chair front porch and soak in the beauty. Enjoy entertaining your friends and family, in the open floor pan with 9 foot ceilings. Stainless Steel Range in the spacious kitchen. This amazing home comes complete with a 4 stall barn, ready for your horses or livestock. You will also find, just beyond the back woodline, a 40x90 Quonset hut with underground power in place...ready for your farm equipment, recreational toys or workshop. ' Oversized 2 Car Garage with 2 Tack Rooms/Storage with outdoor access. An amazing property with all of the beauty of the countyside, convenient to I-10 and Tallahassee.
Step into city living just steps from Downtown Monticello, Fl. This one-story condo with private backyard blends modern convenience in this coveted over 55 neighborhood of only 8 units. 2 bedrooms & 2 baths, laundry room with stack unit, W/D included, but the favorite room in the house is the sunroom. Inside, enjoy the bright open-concept living with high ceilings, crown molding, LVP & engineered flooring with a cozy electric fireplace that can be converted to gas very easily if desired. Kitchen is spacious & the best part is all of the stainless appliances were new in 2022. AC/heat pump unit was installed in 2022, all windows & doors replaced in 2023, hot water heater & roof in 2025. 1 car garage is perfect for the days that it rains and adds storage if needed. Outside, your enchanting patio features privacy, grassy area for your pet and fencing. Hardi-plank siding is almost maintenance free and adds to the almost new-look of this home. This is a must see home as it is beautiful!
Enjoy the gorgeous water views from the porch of this like-new, 2022 built home! A Gated driveway leads to your 5 acre parcel on a beautiful 10 acre spring-fed lake with great fishing. 6 ft windows and 8x8 sliding doors allow the open living, dining, and kitchen areas to view the sunny outdoors. Kitchen features a large island with seating area, stainless appliances, gas stove, and fridge with dual ice maker. Living spaces spill over onto the covered front porch, and screened back porch. Primary suite includes a huge 8x18 closet, spacious bathroom with double sinks, large walk-in shower, tub, and separate toilet area. Almost entire attic space is floored for lots of additional storage. 20x20 insulated workshop with electricity, hot water, mini split AC, and loft area for storage and outdoor projects, plus an additional shed with power, and an RV hookup. 2 tankless water heaters. LVP floors throughout. Standing seam metal roof.
New construction; very convenient to downtown; house is close to completion - should be ready in about 45 days.
A Timeless Treasure, built by Riley Palmer Construction in 2006, this exceptional home captures the warmth and character of an early-1900s Craftsman farmhouse. It is located on 5 beautiful acres with mature pecan trees in the front and pines in the back yard. A spacious wrap around front porch welcomes you and features reclaimed New Orleans style doors and classic architectural details. Inside, the home is rich with custom craftsmanship, including 10-foot ceilings, custom wood floors milled from trees on the property, antique light fixtures, and extensive, detailed trim throughout. This home reflects thoughtful design and timeless quality. Truly one of a kind, this is a must see property that must be experienced in person to be fully appreciated.
Currently under construction. Interior pictures are from a previous model home. Approximately 60 days until completion. Home qualifies for USDA financing.
Great location for this property in Lloyd Acres. The property has 2.26 acres of partially wooded area. The property consists of the single family home, detached garage/carport/workshop and a singlewide mobile home. The vinyl sided home will need some repair and updating but has tremendous potential. The detached garage is large with 2 stalls. The mobile home is in need of a total renovation (or demolition).
This beautifully maintained modular home sits on 2.77 acres, offering peaceful waterfront living and modern updates throughout. Built in 2005 and thoughtfully upgraded, this 3-bedroom, 2-bathroom home combines comfort, style, and space for an idyllic Jefferson County setting. The expansive open-concept-style main living/dining area is perfect for entertaining or relaxing with family. An adjoining family room/flex-space offers additional versatility — it is currently set up with a pool table and is being partially utilized as a home office. It’s adjacency to the kitchen and direct access to the deck affords convenience for all uses. The kitchen boasts a breakfast bar, updated stainless steel appliances, a separate pantry with added shelving, plenty of counter space, and ample cabinetry for storage. The impressive master suite, features private deck access from the bedroom, generous his-and-hers walk-in closets, and an updated en-suite bath with a tiled walk-in shower, jetted tub with tiled surround, two new separate vanities, and a private water closet – your very own sanctuary! Other notable upgrades and key system updates include: wood laminate flooring throughout, fresh interior and exterior paint, all new exterior doors, a brand-new HVAC system (2025), Hot Water Heater (2024), and Roof (2018). Outdoors, enjoy the private deck, which overlooks the pond – perfect for sipping morning coffee, backyard barbecues, or simply taking in the evening sunsets. Hardie Board siding, a large circle drive, professionally landscaped front flower beds and scattered, mature oak trees enhance the home’s welcoming curb appeal. The property utilizes Jefferson Communities Water for it’s water supply and is on a private septic system. Conveniently located within proximity to I-10, making for an easy 20-minute commute to/from Tallahassee, and just minutes from historic downtown Monticello.
New construction in the heart of Monticello's Historic District! This beautifully built 1,092 sq ft off-grade home offers modern finishes while fitting seamlessly into the character of the neighborhood. The open floor plan features luxury vinyl plank flooring throughout, a stylish kitchen and stainless steel appliances, and quality craftsmanship from top to bottom. Bathrooms are finished with tile shower and bath surrounds, providing both durability and a clean, contemporary look. Conveniently located near downtown Monticello, shops, dining, and local amenities. A rare opportunity to own brand-new construction in a historic setting. Pictures are virtual.
Don't judge this home by its exterior!! The outside siding shows significant deterioration, which is fully reflected in the price. However, once inside, you'll find a livable interior that's far more functional than first impressions suggest. This double-wide is currently occupied and offers ;an opportunity for a buyer willing to look past the exterior and focus on the potential within. Not insurable in present condition. Must be a cash purchase. Appt. required! Bring all offers! Additional 1 acre parcel adjacent to property available to purchase as well parcel ID: 18-1N-4E-0108-000G-0030.All dimensions approximate, buyer to confirm.
Amazing new construction Available Now 3 bedroom 2 bathroom by Nailed It Tallahassee LLC Luxurious master suite, Kitchen made of dreams, this is a must see! Preferred Lender offering 1% in closing costs! Photos of current home!
Charming home on large .87 acre lot in established subdivision. Sunporch overlooks wooded back yard, a nature lovers paradise. Open floor plan, kitchen/dining/living room combination. 2 car garage with breezeway to the home. An additional 1 acre lot is available for sale with the home for a total of 1.87 acre for $319,000.
Must see this brand new home built by Southern Construction in the downtown Monticello area. Home is complete and ready for its new owners!! Home features 3 bed, 2 baths, granite countertops, upgraded trim package, vinyl plank flooring throughout, tile bathroom and laundry floors, and stainless appliance package. Come get this beautiful home before its gone!!
Probate proceedings underway. Cannot close until court approval. Concrete Block 2/1 Home less than a mile from downtown Monticello! This quaint 888sqft home sits under a metal roof and only requires your vision and a little effort to become a superb starter home or investment opportunity. Property is fully fenced and on city utilities. Room measurements are approximate
One or more photos have been virtually staged (fire in fireplace). Welcome to this beautifully updated modern farmhouse set on 2.14 acres of picturesque and private farmland, offering the perfect blend of peaceful country living and convenient access to town. Surrounded by open skies and scenic views, this property provides privacy, charm, and versatility rarely found. The 4BR/2BA main house features a thoughtfully designed open floor plan. Recent cosmetic updates throughout enhance the home’s warm, modern appeal, while the updated kitchen and bathrooms offer both style and functionality. An encapsulated crawlspace & refinished metal roof add long-term value and peace of mind. Complementing the home is a spacious workshop/barn, complete with a bathroom and an office or additional bedroom, making it ideal for a home business, guest quarters, studio, or hobby space. An adjoining carport provides ample covered parking or equipment storage. While the property feels serene and secluded, it is just minutes from downtown Monticello and offers a quick, convenient drive to Tallahassee, FL, & Thomasville, GA, providing easy access to shopping, dining, and employment. This exceptional property combines modern comforts, flexible spaces, and a tranquil setting - an ideal opportunity for those seeking the best of rural charm and nearby city convenience.
*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.
Move in ready home on over 5 acres in beautiful Monticello Florida. Newer Roof 2024, Freshly painted, new skirting, windows, hot water heater 2024, flooring. No HOA
The data relating to real estate for sale on this website comes in part from the Internet Data Exchange Program of Tallahassee Board of Realtors. The information is provided exclusively for consumers’ personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate.
Monticello is located in Florida. Monticello, Florida has a population of 2,539. Monticello is less family-centric than the surrounding county with 15.42% of the households containing married families with children. The county average for households married with children is 20.81%.
The median household income in Monticello, Florida is $43,780. The median household income for the surrounding county is $53,080 compared to the national median of $69,021. The median age of people living in Monticello is 53.5 years.
The average high temperature in July is 91.4 degrees, with an average low temperature in January of 38.5 degrees. The average rainfall is approximately 53.9 inches per year, with 0.1 inches of snow per year.
