buyandselltallahassee.com Search Results

$450,000

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

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

Fronting on Hwy-90 this high elevation lot is lightly wooded. Some restrictions apply.

399248 MLS

Fronting on Hwy-90 this high elevation lot is lightly wooded. Some restrictions apply.

TBD W Washington, Monticello

$259,900

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

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

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.

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

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

$69,900

Owner Financing available with 20% down. Motivated Seller! Unique shaped parcel located in a serene rural area—perfect for building, recreation, or investment

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

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.

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

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!

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

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!

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

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

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

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

$510,000

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

$135,000

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.

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

$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

$429,900

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!

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

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

$45,000

All Offers considered..2.5 Acres of land, partially cleared for home-site. Private quiet road. All high and dry ready to build your homestead. mobile homes okay. Close to aucilla river. Convenient to Monticello, FL and Thomasville Ga. Valdosta and Tallahassee 45 minutes away. Horse Friendly area. Owner financing options available.

395854 MLS

All Offers considered..2.5 Acres of land, partially cleared for home-site. Private quiet road. All high and dry ready to build your homestead. mobile homes okay. Close to aucilla river. Convenient to Monticello, FL and Thomasville Ga. Valdosta and Tallahassee 45 minutes away. Horse Friendly area. Owner financing options available.

1 W meadow Road, 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

$259,000

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.

3 Beds ⋅ 2 Baths ⋅ 394368 MLS

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.

1511 Spring Hollow Road, Monticello

$50,000

Wooded lot, pines and hardwoods. Mobile homes are allowed. High elevation.

393415 MLS

Wooded lot, pines and hardwoods. Mobile homes are allowed. High elevation.

TBD E Meadow Road, Monticello

$529,000

**MOTIVATED SELLERS - CONCESSION(S) BEING OFFERED** Remarkable, peaceful in-town oasis on 3.54 acres! An incredible find in the heart of downtown Monticello, FL. Not only is this home located on a private 3.54 acre spread, surrounded by a perimeter of natural foliage, but the home itself has been beautifully updated, blending the charm of old and the convenience of new. The 3 bedroom/3 bathroom, 2,000+ sq ft home has a kitchen flooded with natural light overlooking beautiful back yard views. The Master Suite is incredibly spacious, with it's own sitting area and/or office space. The Master Bath has a double vanity and tiled walked in shower. The Master also has it's own private, exterior door access. Outdoors, there is a pool house with a lap pool, a commercial grade greenhouse, (2) additional outbuildings (1 with electric/water), a koi pond and beautiful landscaping throughout, with a multitude of gorgeous flowers, planted by a professional gardener/florist, that bloom throughout the year. Hummingbirds are plentiful daily (except during winter) if you keep the feeders full of nectar! Also, the property has a citrus grove with three large orange trees (2 naval and 1 honeybell) and two lime trees. Roof (2022) | A/C (upgraded, 2021). A must see for sure! **Note: One bedroom (10x10) is not pictured, because it was being used for storage at the time photos were taken.

3 Beds ⋅ 3 Baths ⋅ 392310 MLS

**MOTIVATED SELLERS - CONCESSION(S) BEING OFFERED** Remarkable, peaceful in-town oasis on 3.54 acres! An incredible find in the heart of downtown Monticello, FL. Not only is this home located on a private 3.54 acre spread, surrounded by a perimeter of natural foliage, but the home itself has been beautifully updated, blending the charm of old and the convenience of new. The 3 bedroom/3 bathroom, 2,000+ sq ft home has a kitchen flooded with natural light overlooking beautiful back yard views. The Master Suite is incredibly spacious, with it's own sitting area and/or office space. The Master Bath has a double vanity and tiled walked in shower. The Master also has it's own private, exterior door access. Outdoors, there is a pool house with a lap pool, a commercial grade greenhouse, (2) additional outbuildings (1 with electric/water), a koi pond and beautiful landscaping throughout, with a multitude of gorgeous flowers, planted by a professional gardener/florist, that bloom throughout the year. Hummingbirds are plentiful daily (except during winter) if you keep the feeders full of nectar! Also, the property has a citrus grove with three large orange trees (2 naval and 1 honeybell) and two lime trees. Roof (2022) | A/C (upgraded, 2021). A must see for sure! **Note: One bedroom (10x10) is not pictured, because it was being used for storage at the time photos were taken.

515 E Palmer Mill Road, 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

$65,000

1.7 acres, two lots hidden in Monticello. Will not divide. Private setting with Plantation to the west. There is a 15 ft recorded easement to the property but currently working on additional road access. No sign on property. .

388787 MLS

1.7 acres, two lots hidden in Monticello. Will not divide. Private setting with Plantation to the west. There is a 15 ft recorded easement to the property but currently working on additional road access. No sign on property. .

TBD Scott Drive, Monticello

$130,000

The listing contains (2) adjacent raw land parcels in the Lloyd Acres Subdivision = 9.96 acres total. See parcel IDs: 18-1N-4E-0113-000C-0010 (6.41 acres; Mallard Lane) + 18-1N-4E-0112-000C-0050 (3.55 acres; Bluejay Rd). Look for real estate signs (2) to help identify the acreage for sale. The property is zoned Residential-01 (1 home/1 acre), making it a great opportunity for someone wanting to subdivide, or those looking for a multi-generational property to accommodate several residences for family. Mobile homes are allowed. There are currently no utilities in place; electric, well & septic will be required. *Property is subject to a drainage easement over and across the easterly 15.0 ft.**Note - Dimensions shown are for the Mallard Ln parcel only.

383017 MLS

The listing contains (2) adjacent raw land parcels in the Lloyd Acres Subdivision = 9.96 acres total. See parcel IDs: 18-1N-4E-0113-000C-0010 (6.41 acres; Mallard Lane) + 18-1N-4E-0112-000C-0050 (3.55 acres; Bluejay Rd). Look for real estate signs (2) to help identify the acreage for sale. The property is zoned Residential-01 (1 home/1 acre), making it a great opportunity for someone wanting to subdivide, or those looking for a multi-generational property to accommodate several residences for family. Mobile homes are allowed. There are currently no utilities in place; electric, well & septic will be required. *Property is subject to a drainage easement over and across the easterly 15.0 ft.**Note - Dimensions shown are for the Mallard Ln parcel only.

00 Mallard/Blue Jay Lane Unit 2/3, Monticello

$164,900

*Some photos may be virtually staged* New beautiful LVP flooring on mother in law suite side of the property and wdo repair underneath the new flooring!! So many options with this property!! It boasts 2 separate living spaces joined by a common family room. One side of the home has 1 bed and 1 bath, it's own kitchen and living space. The other side of the home has 3 bedrooms, 2 bathrooms and the kitchen and living area. The family room with laundry is in the middle of the home. Each side has an enclosed porch too! So much space and an expansive yard too! Located in Monticello and convenient commute to Tallahassee in the neighborhood of Montivilla.

4 Beds ⋅ 3 Baths ⋅ 380257 MLS

*Some photos may be virtually staged* New beautiful LVP flooring on mother in law suite side of the property and wdo repair underneath the new flooring!! So many options with this property!! It boasts 2 separate living spaces joined by a common family room. One side of the home has 1 bed and 1 bath, it's own kitchen and living space. The other side of the home has 3 bedrooms, 2 bathrooms and the kitchen and living area. The family room with laundry is in the middle of the home. Each side has an enclosed porch too! So much space and an expansive yard too! Located in Monticello and convenient commute to Tallahassee in the neighborhood of Montivilla.

34 W Hummingbird Lane, Monticello

$75,000

Prime vacant cleared commercial lot in downtown Monticello. Zoned Commercial B-2 Business Highway. Located Steps from US 19 South Across street from Burger King and Dollar Tree. Next door to Oreilly's Auto parts. High Traffic area and Good visibility. Address is for GPS only. Acreage is subject to survey.

357658 MLS

Prime vacant cleared commercial lot in downtown Monticello. Zoned Commercial B-2 Business Highway. Located Steps from US 19 South Across street from Burger King and Dollar Tree. Next door to Oreilly's Auto parts. High Traffic area and Good visibility. Address is for GPS only. Acreage is subject to survey.

205 E Cherokee Avenue, Monticello

$325,000

Beautiful High lot at corner of Hwy 19, Shiver and Lake Rd. This listing is compilation of 3 contiguous parcels : (19-2N-5E-0140-0000-0300 and 19-2N-5E-0000-0210-0000 and 19-2N-5E-0140-0000-0170). for a total of 3.25 acres . PRIME location for multi-family, office, mixed use commercial business that needs visibility and ease of access. Utilities available- Water access to main line is Under Hwy 19 and across road. (verify with County) ZONING IS: Mixed Use Residential.

367916 MLS

Beautiful High lot at corner of Hwy 19, Shiver and Lake Rd. This listing is compilation of 3 contiguous parcels : (19-2N-5E-0140-0000-0300 and 19-2N-5E-0000-0210-0000 and 19-2N-5E-0140-0000-0170). for a total of 3.25 acres . PRIME location for multi-family, office, mixed use commercial business that needs visibility and ease of access. Utilities available- Water access to main line is Under Hwy 19 and across road. (verify with County) ZONING IS: Mixed Use Residential.

XX SHIVER Road, Monticello