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870 Shady Lane, 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
670 Poplar Street, Monticello
$149,900
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
1164 Oaklands Plantation Road, 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
1628 N Jefferson Highway, 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 24x12 workshop provides valuable storage with a 12x12 chicken coop and multi use 12x12 farm stall behind that. An entertainment deck 24x24 is built around "The Magnolia" and a 16x28 bonus room with a half bath 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
110 Crooked Creek Lane, Monticello
$459,900
3 Beds ⋅ 2 Baths ⋅ 399057 MLS
These photos are from a previous build and some of the photos have been virtually enhanced.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 October 2026. Buyer to verify all measurements.

110 Crooked Creek Lane, Monticello
625 E WASHINGTON Street, 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
121 Shumard Court, Monticello
$495,000
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
8156 Waukeenah Highway, 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
398 Tecumseh Road, 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
220 Eaton Street, 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
640 Nautilus Drive, Monticello
$495,000
2 Beds ⋅ 1 Baths ⋅ 395668 MLS
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.

640 Nautilus Drive, Monticello
930 E Pearl Street, Monticello
$395,000
4 Beds ⋅ 3 Baths ⋅ 391898 MLS
Built between 1890–1910, this Classic Revival home sits on 1.77 acres along one of Monticello’s most admired streets and offers timeless architecture with an opportunity to restore and make it your own. The two-story layout includes 4 bedrooms and 3 bathrooms, with a circular driveway framed by boxwoods leading to a wide front porch perfect for rocking chairs. Inside, two front parlors flank the entry—one used as a living room and one with a closet allowing for modern use as a bedroom—while upstairs includes two additional bedrooms and a full bath. The large dining room has been opened to expose the original rafters, giving the space a bright and airy feel, while six original (not currently operational) fireplaces provide historic character throughout. Period details including original hardwood floors, banisters, and molding showcase the craftsmanship of the era. Downstairs also includes a family room off the kitchen, a full guest bath, and a primary suite with an attached bath and nearby laundry. The home features a two-zone HVAC system downstairs, with window units currently serving the upstairs bedrooms. The roof is estimated to have approximately 5–7 years of remaining life. This property offers an opportunity for thoughtful updates and stewardship, presenting a great fit for buyers looking to invest in a historic home with strong bones and character. The back portion of the property remains wooded, providing privacy or potential to expand with a guest house, pool, or garden. Conveniently located just a short walk to downtown Monticello’s shops and restaurants, about 25 minutes to Thomasville, and roughly 30 minutes to Tallahassee. Offered As-Is, this home has over a century of stories—it’s ready for its next chapter. Seller is motivated and will consider all offers.

930 E Pearl Street, Monticello