buyandselltallahassee.com Search Results

$699,000

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.

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

$149,900

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.

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

$398,900

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.

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

$439,900

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.

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

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

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

$599,900

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!

4 Beds ⋅ 3 Baths ⋅ 398548 MLS

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

$1,950,000

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

6 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

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.

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

$495,000

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.

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

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!

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

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!

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

$775,000

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.

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

Very convenient location in the heart of Monticello. Excellent condition. Very good condition, new roof, new windows, newer flooring throughout. 10X12 storage shed.

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

$1,325,000

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.

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

$495,000

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.

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

$395,000

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.

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