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360 Bowman Street, Monticello

This home is currently coming out of the permitting phase. New construction will start in the next week. Completion date should be approx 4 months or less. We will update the comments as the construction progresses. Picture is virtual. More to come as construction continues.

3 Beds ⋅ 2 Baths ⋅ 402229 MLS

This home is currently coming out of the permitting phase. New construction will start in the next week. Completion date should be approx 4 months or less. We will update the comments as the construction progresses. Picture is virtual. More to come as construction continues.

1565 Sweetbay Court, Monticello

$1,200,000

**Some Photos are Virtually Enhanced** Experience luxury living in the prestigious gated community of Rainey Run. This is where privacy, nature, and convenience come together on 10 breathtaking acres. Surrounded by towering hardwoods and abundant wildlife, this remarkable property offers a convenient peaceful retreat. Built in 2020, this custom home showcases quality craftsmanship with a highly thought out design. Greeted by a beautifully crafted foyer, you immediately feel at home from the moment you walk through the door. The spacious kitchen opens to the living room offering the perfect entertainment design. The spacious floor plan is designed for both comfortable everyday living and effortless entertaining. Allowing privacy with its split floor plan, the primary bedroom features his and her walking closets with a spa like bathroom escape. 3 bedroom with office (or 4th bedroom) and bonus room (could be used as another bedroom). Step outside and enjoy your own private sanctuary, where deer, turkey, and other native wildlife are frequent visitors. A large workshop with electricity and water provides endless opportunities for hobbies or equipment storage. Located behind the gates of one of Jefferson County’s most desirable communities, Rainey Run offers the peaceful escape from the city with the convenience of Tallahassee being only a few minutes away. Schedule your private showing today, this home has so much more to share! Built by Saxon Hannon, of Hannon Construction. Buyers to verify all dimensions and measurements.

4 Beds ⋅ 3 Baths ⋅ 402221 MLS

**Some Photos are Virtually Enhanced** Experience luxury living in the prestigious gated community of Rainey Run. This is where privacy, nature, and convenience come together on 10 breathtaking acres. Surrounded by towering hardwoods and abundant wildlife, this remarkable property offers a convenient peaceful retreat. Built in 2020, this custom home showcases quality craftsmanship with a highly thought out design. Greeted by a beautifully crafted foyer, you immediately feel at home from the moment you walk through the door. The spacious kitchen opens to the living room offering the perfect entertainment design. The spacious floor plan is designed for both comfortable everyday living and effortless entertaining. Allowing privacy with its split floor plan, the primary bedroom features his and her walking closets with a spa like bathroom escape. 3 bedroom with office (or 4th bedroom) and bonus room (could be used as another bedroom). Step outside and enjoy your own private sanctuary, where deer, turkey, and other native wildlife are frequent visitors. A large workshop with electricity and water provides endless opportunities for hobbies or equipment storage. Located behind the gates of one of Jefferson County’s most desirable communities, Rainey Run offers the peaceful escape from the city with the convenience of Tallahassee being only a few minutes away. Schedule your private showing today, this home has so much more to share! Built by Saxon Hannon, of Hannon Construction. Buyers to verify all dimensions and measurements.

974 Rainey Run, Monticello

$62,800

The following parcels are included in the sale: 32-2N-6E-0000-0023-0000 & 32-2N-6E-0000-0024-0000 This beautiful, wooded property offers a diverse landscape that's ideal for recreation, hunting, or building your private retreat. Mature hardwoods and towering pines create a peaceful forest setting, while natural clearings provide excellent locations for a homesite, food plots, or camping. The property features a mix of open understory and dense cover, supporting abundant wildlife habitat. Existing trails make it easy to explore, and an elevated hunting stand is already in place for outdoor enthusiasts. Whether you're looking for a quiet getaway, a hunting tract, or land to build your dream home, this property combines natural beauty, privacy, and endless potential.

402172 MLS

The following parcels are included in the sale: 32-2N-6E-0000-0023-0000 & 32-2N-6E-0000-0024-0000 This beautiful, wooded property offers a diverse landscape that's ideal for recreation, hunting, or building your private retreat. Mature hardwoods and towering pines create a peaceful forest setting, while natural clearings provide excellent locations for a homesite, food plots, or camping. The property features a mix of open understory and dense cover, supporting abundant wildlife habitat. Existing trails make it easy to explore, and an elevated hunting stand is already in place for outdoor enthusiasts. Whether you're looking for a quiet getaway, a hunting tract, or land to build your dream home, this property combines natural beauty, privacy, and endless potential.

XXX Neely Road, Monticello

$424,900

Stunning New Construction recently built by Southern Construction. Centrally located in downtown Monticello, with mature landscaping, and plenty of room for the family. This 4 bed and 3 bath home features vinyl plank flooring, granite countertops, walk in tile shower and tub in master, upgraded trim package, and stainless appliances. Nice large back porch with deck, over looking the large beautiful back yard!! Come see all this home has to offer today!!

4 Beds ⋅ 3 Baths ⋅ 402136 MLS

Stunning New Construction recently built by Southern Construction. Centrally located in downtown Monticello, with mature landscaping, and plenty of room for the family. This 4 bed and 3 bath home features vinyl plank flooring, granite countertops, walk in tile shower and tub in master, upgraded trim package, and stainless appliances. Nice large back porch with deck, over looking the large beautiful back yard!! Come see all this home has to offer today!!

855 S Waukeenah Street, Monticello

$285,000

Great potential, use one side and lease out the other. Duplex 310 and 320 N. Cherry St., each unit has a bathroom. The building is currently under renovation with new roof in 2025, new front windows, new vinyl plank flooring throughout most of the building.

401828 MLS

Great potential, use one side and lease out the other. Duplex 310 and 320 N. Cherry St., each unit has a bathroom. The building is currently under renovation with new roof in 2025, new front windows, new vinyl plank flooring throughout most of the building.

320 N Cherry Street, Monticello

$269,900

Tucked behind a gated entrance and nestled on 5.54 acres, this property offers the privacy, space, and freedom that is hard to find at this price point. With no HOA, you'll have the flexibility to enjoy true country living with plenty of room for horses, livestock, RVs, trailers, ATVs, UTVs, and more. Upon arrival, you're greeted by a large, open parking area with ample space for vehicles, equipment, and guests. The expansive front porch sets the tone, inviting you to enjoy quiet mornings with a cup of coffee overlooking your land and relaxing evenings surrounded by nature. Inside, the well-maintained home features a functional layout designed for everyday living and entertaining. The entry opens into a spacious family room, separate living room, and dining area just off the kitchen, offering multiple gathering spaces. The generously sized kitchen provides abundant workspace and connects to a dedicated laundry room for added convenience. The split-bedroom floor plan offers privacy, with the primary suite featuring a garden tub, double vanities, and a walk-in closet. On the opposite side of the home, you'll find two additional bedrooms and a full guest bathroom. Step outside to the screened-in porch, the perfect place to entertain family and friends or simply relax while taking in the peaceful surroundings. The property also includes a heated and cooled shed that's ideal for a home office, gym, or creative studio, a fire pit for evenings under the stars, and an additional storage shed. Complete with a fenced yard and meticulously maintained grounds, this versatile property offers a rare opportunity to enjoy the privacy, flexibility, and lifestyle that only acreage living can provide.

3 Beds ⋅ 2 Baths ⋅ 401821 MLS

Tucked behind a gated entrance and nestled on 5.54 acres, this property offers the privacy, space, and freedom that is hard to find at this price point. With no HOA, you'll have the flexibility to enjoy true country living with plenty of room for horses, livestock, RVs, trailers, ATVs, UTVs, and more. Upon arrival, you're greeted by a large, open parking area with ample space for vehicles, equipment, and guests. The expansive front porch sets the tone, inviting you to enjoy quiet mornings with a cup of coffee overlooking your land and relaxing evenings surrounded by nature. Inside, the well-maintained home features a functional layout designed for everyday living and entertaining. The entry opens into a spacious family room, separate living room, and dining area just off the kitchen, offering multiple gathering spaces. The generously sized kitchen provides abundant workspace and connects to a dedicated laundry room for added convenience. The split-bedroom floor plan offers privacy, with the primary suite featuring a garden tub, double vanities, and a walk-in closet. On the opposite side of the home, you'll find two additional bedrooms and a full guest bathroom. Step outside to the screened-in porch, the perfect place to entertain family and friends or simply relax while taking in the peaceful surroundings. The property also includes a heated and cooled shed that's ideal for a home office, gym, or creative studio, a fire pit for evenings under the stars, and an additional storage shed. Complete with a fenced yard and meticulously maintained grounds, this versatile property offers a rare opportunity to enjoy the privacy, flexibility, and lifestyle that only acreage living can provide.

60 Bob White Trail, Monticello

$139,000

Great Location in Western Jefferson County offering country living with the convenience of Tallahassee only minutes away. Wooded 5 acres on private lane. Restricted for site built homes with minimum of 1200 sq ft heated and cooled. Adjoining 5 available for sale.

401806 MLS

Great Location in Western Jefferson County offering country living with the convenience of Tallahassee only minutes away. Wooded 5 acres on private lane. Restricted for site built homes with minimum of 1200 sq ft heated and cooled. Adjoining 5 available for sale.

tbd Orchard, Monticello

$139,000

Great Location in Western Jefferson County offering country living with the convenience of Tallahassee only minutes away. Wooded 5 acres on private lane. Restricted for site built homes with minimum of 1200 sq ft heated and cooled. Adjoining 5 available for sale.

401805 MLS

Great Location in Western Jefferson County offering country living with the convenience of Tallahassee only minutes away. Wooded 5 acres on private lane. Restricted for site built homes with minimum of 1200 sq ft heated and cooled. Adjoining 5 available for sale.

TBD Orchard Lane, Monticello

$539,500

ENJOY THE QUIET SPACE OF THE SANCTUARY IN LLOYD*JUST 20 MINUTES FROM TALLAHASSEE* THIS FOUR BEDROOM TWO BATH HOME WAS BUILT IN 2020 WITH STYLISH FIXTURES AND DESIGN* ENJOY ONE ACRE ON A CORNER LOT WITH A FULLY FENCED BACKYARD* PLENTY OF SPACE FOR A BIG FAMILY AND PETS TO ROAM* THE HOME FEATURES A SPLIT BEDROOM FLOOR PLAN WITH A GORGEOUS OPEN LIVING, DINING AND KITCHEN SPACE* 2 CAR GARAGE AND GORGEOUS COMMUNITY WITH NO HOA FEES*

4 Beds ⋅ 2 Baths ⋅ 401695 MLS

ENJOY THE QUIET SPACE OF THE SANCTUARY IN LLOYD*JUST 20 MINUTES FROM TALLAHASSEE* THIS FOUR BEDROOM TWO BATH HOME WAS BUILT IN 2020 WITH STYLISH FIXTURES AND DESIGN* ENJOY ONE ACRE ON A CORNER LOT WITH A FULLY FENCED BACKYARD* PLENTY OF SPACE FOR A BIG FAMILY AND PETS TO ROAM* THE HOME FEATURES A SPLIT BEDROOM FLOOR PLAN WITH A GORGEOUS OPEN LIVING, DINING AND KITCHEN SPACE* 2 CAR GARAGE AND GORGEOUS COMMUNITY WITH NO HOA FEES*

333 Post Oak Circle, Monticello

$254,999

Back on the market at NO FAULT TO THE SELLERS! Looking for a peaceful escape from the hustle and bustle? Welcome to your own private piece of North Florida! Tucked away on 5 beautiful acres between Tallahassee and historic Monticello, this spacious mobile home offers 1,792 square feet of comfortable living space with room to spread out and make it your own.Enjoy quiet mornings on the inviting front porch with a cup of coffee or unwind in the evenings on the large back porch overlooking your own slice of paradise. The property is enhanced by a beautiful collection of mature trees and landscaping, including cedar, hickory, southern magnolia, Japanese loquat, hardy orange, mulberry, pineapple guava (Feijoa), camellias, crape myrtles, Chinese fringe flowers, Spanish Sunset roses, holly, and more—creating year-round beauty, shade, and privacy.Nature lovers will appreciate the seasonal creek that meanders through the property, adding to the peaceful setting and attracting local wildlife. Two storage sheds provide plenty of space for tools, equipment, hobbies, or additional storage. Whether you’re looking for a homestead, hobby farm, weekend retreat, or simply a place to enjoy the freedom and tranquility of country living, this property offers endless possibilities. Experience the best of both worlds—privacy, acreage, and natural beauty—while remaining just a short drive from Tallahassee, Monticello, shopping, dining, and everyday conveniences.

3 Beds ⋅ 2 Baths ⋅ 401558 MLS

Back on the market at NO FAULT TO THE SELLERS! Looking for a peaceful escape from the hustle and bustle? Welcome to your own private piece of North Florida! Tucked away on 5 beautiful acres between Tallahassee and historic Monticello, this spacious mobile home offers 1,792 square feet of comfortable living space with room to spread out and make it your own.Enjoy quiet mornings on the inviting front porch with a cup of coffee or unwind in the evenings on the large back porch overlooking your own slice of paradise. The property is enhanced by a beautiful collection of mature trees and landscaping, including cedar, hickory, southern magnolia, Japanese loquat, hardy orange, mulberry, pineapple guava (Feijoa), camellias, crape myrtles, Chinese fringe flowers, Spanish Sunset roses, holly, and more—creating year-round beauty, shade, and privacy.Nature lovers will appreciate the seasonal creek that meanders through the property, adding to the peaceful setting and attracting local wildlife. Two storage sheds provide plenty of space for tools, equipment, hobbies, or additional storage. Whether you’re looking for a homestead, hobby farm, weekend retreat, or simply a place to enjoy the freedom and tranquility of country living, this property offers endless possibilities. Experience the best of both worlds—privacy, acreage, and natural beauty—while remaining just a short drive from Tallahassee, Monticello, shopping, dining, and everyday conveniences.

196 Private Road, Monticello

$539,000

This one truly has it all! Nestled on 5+ private acres in beautiful Monticello, Florida, this 4-bedroom, 2.5-bath home offers the perfect blend of comfort, privacy, and charm. Step inside to a spacious split floor plan featuring 10-foot tray ceilings, real hardwood floors, a cozy wood-burning fireplace, and abundant natural light throughout. The beautifully updated kitchen features granite countertops, a stone backsplash, tiled flooring, a large pantry, and a charming breakfast nook. The inviting living room opens through French doors to an expansive screened porch—the perfect place to relax while enjoying the peaceful views, birds, and local wildlife. The spacious primary suite is a true retreat with three large bay windows, private access to the screened porch, a luxurious ensuite bath featuring a deep whirlpool tub, walk-in shower, double vanities, and an oversized walk-in closet. Outside, you'll find even more to love, including a 2022 roof, 2 - 2 car garages - an oversized attached garage, an additional detached two-car garage, and a red barn complete with power and lighting. Additional upgrades include LeafFilter gutters, a water softener system, and both the front and backyard are fenced for added privacy and functionality. Manual transfer switch with 50 amp RV plug installed early last year If you've been dreaming of peaceful country living without sacrificing modern conveniences, this property is a must-see!

4 Beds ⋅ 3 Baths ⋅ 401514 MLS

This one truly has it all! Nestled on 5+ private acres in beautiful Monticello, Florida, this 4-bedroom, 2.5-bath home offers the perfect blend of comfort, privacy, and charm. Step inside to a spacious split floor plan featuring 10-foot tray ceilings, real hardwood floors, a cozy wood-burning fireplace, and abundant natural light throughout. The beautifully updated kitchen features granite countertops, a stone backsplash, tiled flooring, a large pantry, and a charming breakfast nook. The inviting living room opens through French doors to an expansive screened porch—the perfect place to relax while enjoying the peaceful views, birds, and local wildlife. The spacious primary suite is a true retreat with three large bay windows, private access to the screened porch, a luxurious ensuite bath featuring a deep whirlpool tub, walk-in shower, double vanities, and an oversized walk-in closet. Outside, you'll find even more to love, including a 2022 roof, 2 - 2 car garages - an oversized attached garage, an additional detached two-car garage, and a red barn complete with power and lighting. Additional upgrades include LeafFilter gutters, a water softener system, and both the front and backyard are fenced for added privacy and functionality. Manual transfer switch with 50 amp RV plug installed early last year If you've been dreaming of peaceful country living without sacrificing modern conveniences, this property is a must-see!

761 Hawkins Road, Monticello

$299,900

New Construction currently being built by Southern Construction. Home should be completed in August 2026. Home is located in a great location in S. Jefferson County, close to the Wacissa River. Home features 3 beds and 2 baths, hardi siding, granite countertops with large kitchen island, open floor plan, and vinyl plank flooring in bedrooms and common area. Master bath features large walk-in tile shower. Home is situated on larger over an acre lot, with plenty of room for the entire family!! Come see all this home has to offer today!!

3 Beds ⋅ 2 Baths ⋅ 401502 MLS

New Construction currently being built by Southern Construction. Home should be completed in August 2026. Home is located in a great location in S. Jefferson County, close to the Wacissa River. Home features 3 beds and 2 baths, hardi siding, granite countertops with large kitchen island, open floor plan, and vinyl plank flooring in bedrooms and common area. Master bath features large walk-in tile shower. Home is situated on larger over an acre lot, with plenty of room for the entire family!! Come see all this home has to offer today!!

12180 Gamble Road, Monticello

$25,000

This beautiful old Florida habitat is great for wildlife observation, birding, native forest growth, riding four-wheelers, building nesting boxes for ducks and bats or a hammock and a place to get away for primitive camping. Costco in Tallahassee, Florida is 30.4 miles and Walmart Supercenter in Perry, Florida is 32.1 miles. Monticello, Florida is 9.3 miles for Ice Cream and boutiques, shops, churches and restaurants.

401490 MLS

This beautiful old Florida habitat is great for wildlife observation, birding, native forest growth, riding four-wheelers, building nesting boxes for ducks and bats or a hammock and a place to get away for primitive camping. Costco in Tallahassee, Florida is 30.4 miles and Walmart Supercenter in Perry, Florida is 32.1 miles. Monticello, Florida is 9.3 miles for Ice Cream and boutiques, shops, churches and restaurants.

TBD S Salt Road, Monticello

$425,000

Two houses perfect for generational living or rental income. These move-in-ready homes are in good condition, convenient to Monticello while maintaining privacy. The larger home is a 1550's era brick ranch-style home that is well maintained with newer roof (2022), new electric (2025), new plumbing (2025), tankless water heater and whole house generator. The main living area is 2,659 sf with 5 bedroom and 2 full bathrooms. There's also a sunroom, and a 396 sf attached bonus room suitable for an office or workshop, plus 3 small outbuildings, one with working electric. The guest house includes 3 bedrooms and 2 bathrooms. Built in the 1950's, it's functional but not fancy. It is in good condition with newer roof, plumbing (2025), and electric (2025). Both homes have a fresh coat of paint. The houses are on 2 separate contiguous parcels (1.3 ac and 0.64 ac) but are being offered together. A great housing buy for someone looking for a lot of living space.

401409 MLS

Two houses perfect for generational living or rental income. These move-in-ready homes are in good condition, convenient to Monticello while maintaining privacy. The larger home is a 1550's era brick ranch-style home that is well maintained with newer roof (2022), new electric (2025), new plumbing (2025), tankless water heater and whole house generator. The main living area is 2,659 sf with 5 bedroom and 2 full bathrooms. There's also a sunroom, and a 396 sf attached bonus room suitable for an office or workshop, plus 3 small outbuildings, one with working electric. The guest house includes 3 bedrooms and 2 bathrooms. Built in the 1950's, it's functional but not fancy. It is in good condition with newer roof, plumbing (2025), and electric (2025). Both homes have a fresh coat of paint. The houses are on 2 separate contiguous parcels (1.3 ac and 0.64 ac) but are being offered together. A great housing buy for someone looking for a lot of living space.

2664 W Washington Highway Unit Two Homes, Monticello

$325,000

FULLY RENOVATED SPACIOUS HOUSE, 1.3 acres, on picturesque US 90 near Monticello. This move-in-ready home in good condition is a 1950’s era brick ranch-style home with new plumbing, new electric, fresh paint, new roof, and a whole home generator. The main living area is 2,659 sf with a unique two levels. 5 bedrooms and 2 baths with plenty of character, including the "Captain's Room" with built-in drawers and cubbies. There’s also a 396 sf bonus room suitable for an office or workshop, plus 3 small outbuildings, one with power. Super location just 3 miles west of charming Monticello on beautiful U.S. 90; only 19 minutes from Tallahassee Amazon facility and Publix/Vineyard at I-10. Secluded due to natural vegetation, yet convenient to town.

5 Beds ⋅ 2 Baths ⋅ 401408 MLS

FULLY RENOVATED SPACIOUS HOUSE, 1.3 acres, on picturesque US 90 near Monticello. This move-in-ready home in good condition is a 1950’s era brick ranch-style home with new plumbing, new electric, fresh paint, new roof, and a whole home generator. The main living area is 2,659 sf with a unique two levels. 5 bedrooms and 2 baths with plenty of character, including the "Captain's Room" with built-in drawers and cubbies. There’s also a 396 sf bonus room suitable for an office or workshop, plus 3 small outbuildings, one with power. Super location just 3 miles west of charming Monticello on beautiful U.S. 90; only 19 minutes from Tallahassee Amazon facility and Publix/Vineyard at I-10. Secluded due to natural vegetation, yet convenient to town.

2664 A W Washington Highway, Monticello

$175,000

AFFORDABLE OLD MONTICELLO (FL) HOME. Spacious, good condition, move-in-ready. Convenient, easy walk to charming downtown. Recent basic repairs and renovations (roofing, electrical, etc). Old but very livable and flexible floor plan. Four possible bedrooms, two baths. Recent central heat and air. Large deck equipped with a hot tub (unknown condition) and fenced. Handicap ramp. Huge two-story storage shed. Spacious lot. This early 1900’s home is still very livable, very affordable, but with lots of potential for adding upgrades and value.

3 Beds ⋅ 2 Baths ⋅ 401390 MLS

AFFORDABLE OLD MONTICELLO (FL) HOME. Spacious, good condition, move-in-ready. Convenient, easy walk to charming downtown. Recent basic repairs and renovations (roofing, electrical, etc). Old but very livable and flexible floor plan. Four possible bedrooms, two baths. Recent central heat and air. Large deck equipped with a hot tub (unknown condition) and fenced. Handicap ramp. Huge two-story storage shed. Spacious lot. This early 1900’s home is still very livable, very affordable, but with lots of potential for adding upgrades and value.

520 E High Street, Monticello

$435,000

Built in 2021 | 1,919 Sq. Ft. | Modern Upgrades | Move-In Ready Welcome home to this beautifully maintained 2021-built residence offering approximately 1,900 square feet of thoughtfully designed living space with today’s most sought-after features. This move-in ready home boasts an open-concept floor plan, durable luxury vinyl plank (LVP) flooring, abundant natural light, and high-end finishes throughout. The spacious kitchen is the heart of the home, featuring quartz countertops, gas appliances, ample cabinetry, generous prep space, and a functional layout that flows seamlessly into the living and dining areas—perfect for entertaining or everyday living. The private owner’s suite offers a relaxing retreat, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to enjoy the fully fenced backyard, ideal for pets, children, gardening, or outdoor gatherings. A powered storage shed offers endless possibilities as a workshop, hobby space, or extra storage for tools and equipment. Additional highlights include energy-efficient newer construction, modern finishes, low-maintenance living, quality craftsmanship, and a desirable layout designed for today’s lifestyle. Whether you’re searching for a primary residence or your next investment, this exceptional home checks all the boxes with its modern amenities, functional design, and turnkey condition.

3 Beds ⋅ 2 Baths ⋅ 401282 MLS

Built in 2021 | 1,919 Sq. Ft. | Modern Upgrades | Move-In Ready Welcome home to this beautifully maintained 2021-built residence offering approximately 1,900 square feet of thoughtfully designed living space with today’s most sought-after features. This move-in ready home boasts an open-concept floor plan, durable luxury vinyl plank (LVP) flooring, abundant natural light, and high-end finishes throughout. The spacious kitchen is the heart of the home, featuring quartz countertops, gas appliances, ample cabinetry, generous prep space, and a functional layout that flows seamlessly into the living and dining areas—perfect for entertaining or everyday living. The private owner’s suite offers a relaxing retreat, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to enjoy the fully fenced backyard, ideal for pets, children, gardening, or outdoor gatherings. A powered storage shed offers endless possibilities as a workshop, hobby space, or extra storage for tools and equipment. Additional highlights include energy-efficient newer construction, modern finishes, low-maintenance living, quality craftsmanship, and a desirable layout designed for today’s lifestyle. Whether you’re searching for a primary residence or your next investment, this exceptional home checks all the boxes with its modern amenities, functional design, and turnkey condition.

1680 Willow Road, Monticello

$429,000

One or more pictures is virtually enhanced *Jefferson County peaceful country living with a waterfront backdrop! Built in 2008, this well maintained 3 bedroom, 2 bath home sits on 4.89 beautifully (mostly cleared) acres offering privacy and natural beauty backing directly up to Lloyd Lake- perfect for relaxing evenings with scenic views. Pretty rocking chair front porch as well as a screened in back porch with a propane hookup for grilling and generator hookup. This split plan offers a large primary suite with dual vanities, large walk in shower w/separate soaking tub and large walk in closet. Other features include LVP wood flooring, wood burning fireplace, tankless water heater, an indoor laundry room, ceiling fans, alarm and water softener. Convenient outdoor storage w/2 tool sheds- one w/ power hook up.

3 Beds ⋅ 2 Baths ⋅ 401255 MLS

One or more pictures is virtually enhanced *Jefferson County peaceful country living with a waterfront backdrop! Built in 2008, this well maintained 3 bedroom, 2 bath home sits on 4.89 beautifully (mostly cleared) acres offering privacy and natural beauty backing directly up to Lloyd Lake- perfect for relaxing evenings with scenic views. Pretty rocking chair front porch as well as a screened in back porch with a propane hookup for grilling and generator hookup. This split plan offers a large primary suite with dual vanities, large walk in shower w/separate soaking tub and large walk in closet. Other features include LVP wood flooring, wood burning fireplace, tankless water heater, an indoor laundry room, ceiling fans, alarm and water softener. Convenient outdoor storage w/2 tool sheds- one w/ power hook up.

285 Mallard Lane, Monticello

$58,000

Don't miss this exceptional 0.89-acre homesite in the Desirable Cooper's Pond community. This lot offers the perfect opportunity to create your dream home in a well-established neighborhood known for its attractive surroundings and welcoming atmosphere. Enjoy the convenience of being just minutes from town, with easy access to shopping, dining, schools, and everday amenities while still maintaining the peace and privacy of a residential setting. With ample space for your custom home and outdoor living areas, this property combines neighborhood charm with practical convenience.

400968 MLS

Don't miss this exceptional 0.89-acre homesite in the Desirable Cooper's Pond community. This lot offers the perfect opportunity to create your dream home in a well-established neighborhood known for its attractive surroundings and welcoming atmosphere. Enjoy the convenience of being just minutes from town, with easy access to shopping, dining, schools, and everday amenities while still maintaining the peace and privacy of a residential setting. With ample space for your custom home and outdoor living areas, this property combines neighborhood charm with practical convenience.

Spring Hollow Drive, Monticello

$200,000

Charming and affordable home on the North side of Monticello in Nobles Subdivision. 3 BR 1.5 Baths. Upgrades in 2021 include new ac, new water heater, new roof. Recent interior paint. Large fenced backyard.

3 Beds ⋅ 2 Baths ⋅ 400858 MLS

Charming and affordable home on the North side of Monticello in Nobles Subdivision. 3 BR 1.5 Baths. Upgrades in 2021 include new ac, new water heater, new roof. Recent interior paint. Large fenced backyard.

1550 Tennessee Street, Monticello

$298,900

Currently under construction. Interior pictures are from a previous model home. Approximately 60 days until completion. Home qualifies for USDA financing.

3 Beds ⋅ 2 Baths ⋅ 400806 MLS

Currently under construction. Interior pictures are from a previous model home. Approximately 60 days until completion. Home qualifies for USDA financing.

1070 Partridge Lane, Monticello

$319,900

Recently built home featuring spacious open floor plan. Kitchen has raised cabinets, granite counters, stainless steel appliances, large island with plenty of seating & a pantry....overlooks spacious family area with plenty of room for large gatherings, plus separate dining space. First floor also offers 1/2 bath and large storage area under stairs. Upstairs you are greeted with open reading area or study and laundry room. Large master bedroom with on-suite...double sinks and more granite. Walk-in closet and just off nook is optional "his" closet. Two spacious bedrooms and another large bathroom. This home also has a front porch and 2 car garage; is within walking distance to library, historic downtown and coffee house. Pictures are of a model home nearby.

3 Beds ⋅ 3 Baths ⋅ 400805 MLS

Recently built home featuring spacious open floor plan. Kitchen has raised cabinets, granite counters, stainless steel appliances, large island with plenty of seating & a pantry....overlooks spacious family area with plenty of room for large gatherings, plus separate dining space. First floor also offers 1/2 bath and large storage area under stairs. Upstairs you are greeted with open reading area or study and laundry room. Large master bedroom with on-suite...double sinks and more granite. Walk-in closet and just off nook is optional "his" closet. Two spacious bedrooms and another large bathroom. This home also has a front porch and 2 car garage; is within walking distance to library, historic downtown and coffee house. Pictures are of a model home nearby.

300 Bowman Street, Monticello

$765,000

PRIVATE 20-ACRE ESTATE MINUTES FROM TALLAHASSEE - TRAILS, WILDLIFE, PASTURE & CUSTOM HOME (ADJOINING 21 ACRES AVAILABLE-MLS#400837) Nestled among majestic oaks and rolling countryside, this exceptional estate offers a rare combination of privacy, natural beauty and comfortable country living. Beyond the gated entrance lies a beautiful setting of open land, mature trees, and abundant wildlife, offering endless possibilities for equestrian pursuits, a hobby farm, outdoor recreation, or simply a peaceful retreat from the pace of city life. Enjoy morning walks under the forest canopy, spend evenings watching deer and wild turkey from your porch, and observing stars under the dark skies. Yet despite its secluded setting, the property is conveniently located within easy reach of Tallahassee’s shopping, dining, medical facilities, universities, and airport, and a short drive to the historic town of Monticello. The beautifully maintained custom home is designed for both comfort and connection to the surrounding landscape, featuring a main-floor owner’s suite with a luxurious spa bath, energy-efficient Pella double-paned windows, a new roof, and high-speed internet. Outside, a swim spa, covered RV/farm equipment storage, small pond, and acreage for future expansion, barns, guest accommodations, gardens, or additional agricultural pursuits make this property as versatile as it is inviting. Outdoor enthusiasts will appreciate the close proximity to the Wacissa River, known for kayaking, fishing, and plentiful wildlife. With no HOA restrictions, you have the freedom to create the lifestyle you’ve imagined while experiencing the beauty and tranquility that only a truly exceptional North Florida estate can provide.

3 Beds ⋅ 3 Baths ⋅ 400801 MLS

PRIVATE 20-ACRE ESTATE MINUTES FROM TALLAHASSEE - TRAILS, WILDLIFE, PASTURE & CUSTOM HOME (ADJOINING 21 ACRES AVAILABLE-MLS#400837) Nestled among majestic oaks and rolling countryside, this exceptional estate offers a rare combination of privacy, natural beauty and comfortable country living. Beyond the gated entrance lies a beautiful setting of open land, mature trees, and abundant wildlife, offering endless possibilities for equestrian pursuits, a hobby farm, outdoor recreation, or simply a peaceful retreat from the pace of city life. Enjoy morning walks under the forest canopy, spend evenings watching deer and wild turkey from your porch, and observing stars under the dark skies. Yet despite its secluded setting, the property is conveniently located within easy reach of Tallahassee’s shopping, dining, medical facilities, universities, and airport, and a short drive to the historic town of Monticello. The beautifully maintained custom home is designed for both comfort and connection to the surrounding landscape, featuring a main-floor owner’s suite with a luxurious spa bath, energy-efficient Pella double-paned windows, a new roof, and high-speed internet. Outside, a swim spa, covered RV/farm equipment storage, small pond, and acreage for future expansion, barns, guest accommodations, gardens, or additional agricultural pursuits make this property as versatile as it is inviting. Outdoor enthusiasts will appreciate the close proximity to the Wacissa River, known for kayaking, fishing, and plentiful wildlife. With no HOA restrictions, you have the freedom to create the lifestyle you’ve imagined while experiencing the beauty and tranquility that only a truly exceptional North Florida estate can provide.

9901 GAMBLE Road, Monticello

$19,500

0.84-Acre Monticello Lot on Cox Rd – SURVEY & ELEVATION LETTER ALREADY COMPLETED! Excellent opportunity to own a peaceful 0.84-acre parcel (Lots 89 & 90 of Springdale Pecan Plantation) located on Cox Road in beautiful Jefferson County. Surrounded by natural North Florida beauty, this lot offers rural tranquility while keeping you just minutes from historic downtown Monticello and 25-30 minutes to both Thomasville, Ga and Tallahassee, Fla. x BUILDERS & BUYERS SAVE MONEY UPFRONT: Skip the hassle, delay, and out-of-pocket expenses of hiring engineers before you buy. The heavy lifting is already done for you! A full boundary survey (Delta Land Surveyors) and a professional Elevation Letter are completed and will be handed over directly to the buyer. Property Details & Building Advantages: Size: 0.84 +/- Acres with good road frontage on Cox Rd. Ready to Build: Property sits in FEMA Flood Zone A, but the professional elevation certificate proves the natural ground benchmarks sit at 121.0 to 121.28 feet—just inches (approx. 0.5 ft) below the Base Flood Elevation of 121.6 feet. Affordable Construction: Because the ground is so close to the base flood line, clearing requirements for building are minor compared to typical flood zone lots. Location: Zoned residential/agricultural. High-quality local neighborhood feel on a quiet, accessible road. Whether you are looking to build an elevated custom home, place a mobile home (subject to county guidelines), or hold a piece of beautiful Florida land, this lot is priced to move and engineered for your convenience. Documents are available upon request. Drive by and view the property anytime!

400763 MLS

0.84-Acre Monticello Lot on Cox Rd – SURVEY & ELEVATION LETTER ALREADY COMPLETED! Excellent opportunity to own a peaceful 0.84-acre parcel (Lots 89 & 90 of Springdale Pecan Plantation) located on Cox Road in beautiful Jefferson County. Surrounded by natural North Florida beauty, this lot offers rural tranquility while keeping you just minutes from historic downtown Monticello and 25-30 minutes to both Thomasville, Ga and Tallahassee, Fla. x BUILDERS & BUYERS SAVE MONEY UPFRONT: Skip the hassle, delay, and out-of-pocket expenses of hiring engineers before you buy. The heavy lifting is already done for you! A full boundary survey (Delta Land Surveyors) and a professional Elevation Letter are completed and will be handed over directly to the buyer. Property Details & Building Advantages: Size: 0.84 +/- Acres with good road frontage on Cox Rd. Ready to Build: Property sits in FEMA Flood Zone A, but the professional elevation certificate proves the natural ground benchmarks sit at 121.0 to 121.28 feet—just inches (approx. 0.5 ft) below the Base Flood Elevation of 121.6 feet. Affordable Construction: Because the ground is so close to the base flood line, clearing requirements for building are minor compared to typical flood zone lots. Location: Zoned residential/agricultural. High-quality local neighborhood feel on a quiet, accessible road. Whether you are looking to build an elevated custom home, place a mobile home (subject to county guidelines), or hold a piece of beautiful Florida land, this lot is priced to move and engineered for your convenience. Documents are available upon request. Drive by and view the property anytime!

COX Road, Monticello

$289,000

Bring your vision to life in the heart of Historic Downtown Monticello! The possibilities are endless with this beautifully restored commercial building located in the center of Monticello's charming shopping district. Thoughtfully restored with warm rustic character while maintaining its historic appeal, this unique property offers a blank canvas ready to become the home of your next business venture. Benefit from exceptional visibility with both steady pedestrian traffic and prominent road frontage, providing outstanding exposure for your business. The flexible open layout makes it ideal for a boutique, retail store, gallery, café, coffee shop, office, salon, studio, professional services, or countless other business opportunities. Surrounded by locally owned shops, restaurants, and the timeless charm of Historic Downtown Monticello, this property offers the perfect combination of character, location, and opportunity. Whether you're launching a new business, relocating, or expanding an existing one, this is your chance to establish a presence in one of North Florida's most picturesque downtown districts. If you've been searching for a distinctive commercial property with outstanding visibility, character, and unlimited potential, this beautifully restored downtown building is ready for your imagination to make it your own.

400499 MLS

Bring your vision to life in the heart of Historic Downtown Monticello! The possibilities are endless with this beautifully restored commercial building located in the center of Monticello's charming shopping district. Thoughtfully restored with warm rustic character while maintaining its historic appeal, this unique property offers a blank canvas ready to become the home of your next business venture. Benefit from exceptional visibility with both steady pedestrian traffic and prominent road frontage, providing outstanding exposure for your business. The flexible open layout makes it ideal for a boutique, retail store, gallery, café, coffee shop, office, salon, studio, professional services, or countless other business opportunities. Surrounded by locally owned shops, restaurants, and the timeless charm of Historic Downtown Monticello, this property offers the perfect combination of character, location, and opportunity. Whether you're launching a new business, relocating, or expanding an existing one, this is your chance to establish a presence in one of North Florida's most picturesque downtown districts. If you've been searching for a distinctive commercial property with outstanding visibility, character, and unlimited potential, this beautifully restored downtown building is ready for your imagination to make it your own.

230 N JEFFERSON Street, Monticello

$750,000

Warehouse with B-2 Zoning, square footage to be verified. Approx 9000 sq ft of warehouse with remaining space in kitchen, offices, storage. There is living space with large kitchen 19x20. Total of 9 offices/rooms with 3 baths. High visibility corner fronting on Hwy-90. Paint booth from previous out collision business.

400494 MLS

Warehouse with B-2 Zoning, square footage to be verified. Approx 9000 sq ft of warehouse with remaining space in kitchen, offices, storage. There is living space with large kitchen 19x20. Total of 9 offices/rooms with 3 baths. High visibility corner fronting on Hwy-90. Paint booth from previous out collision business.

765 E Washington Street, Monticello

$364,900

Located in the heart of Monticello, this 5-unit investment property offers a prime opportunity for investors looking to add value and generate income. Positioned just minutes from local businesses, shopping, dining, and convenient interstate access, the location provides strong appeal for tenants seeking both convenience and accessibility. Currently, 3 of the units are occupied, providing immediate rental income, while the remaining 2 units are vacant and present an excellent value-add opportunity. Both vacant units are 1-bedroom, 1-bath units that need updating and repairs to become rent-ready, allowing the next owner to renovate and increase overall cash flow potential. Total Bedroom Count is 6 bedrooms and 5 bathrooms. Whether you are looking to expand your investment portfolio, renovate for increased returns, or capitalize on the growing demand for rental housing in Monticello, this property offers strong upside potential in a desirable in-town location.

400229 MLS

Located in the heart of Monticello, this 5-unit investment property offers a prime opportunity for investors looking to add value and generate income. Positioned just minutes from local businesses, shopping, dining, and convenient interstate access, the location provides strong appeal for tenants seeking both convenience and accessibility. Currently, 3 of the units are occupied, providing immediate rental income, while the remaining 2 units are vacant and present an excellent value-add opportunity. Both vacant units are 1-bedroom, 1-bath units that need updating and repairs to become rent-ready, allowing the next owner to renovate and increase overall cash flow potential. Total Bedroom Count is 6 bedrooms and 5 bathrooms. Whether you are looking to expand your investment portfolio, renovate for increased returns, or capitalize on the growing demand for rental housing in Monticello, this property offers strong upside potential in a desirable in-town location.

480 S JEFFERSON Street Unit -, Monticello

$90,000

They don’t build them like they used to! This historic 1900 home located in downtown Monticello sits on nearly a half-acre lot and is full of timeless character waiting to be restored. Featuring original hardwood floors throughout most of the home, beadboard walls, 9+ foot ceilings, and original glass windows, this property offers the charm and craftsmanship so many buyers desire. Spacious 3-bedroom floor plan with an updated kitchen and bathroom already in place. While the home has solid bones and endless potential, it will require significant renovations including electrical updates, roof replacement, plumbing updates, and HVAC installation. A rare opportunity to bring new life to a true piece of Monticello history! All dimensions are approximate.

3 Beds ⋅ 1 Baths ⋅ 400131 MLS

They don’t build them like they used to! This historic 1900 home located in downtown Monticello sits on nearly a half-acre lot and is full of timeless character waiting to be restored. Featuring original hardwood floors throughout most of the home, beadboard walls, 9+ foot ceilings, and original glass windows, this property offers the charm and craftsmanship so many buyers desire. Spacious 3-bedroom floor plan with an updated kitchen and bathroom already in place. While the home has solid bones and endless potential, it will require significant renovations including electrical updates, roof replacement, plumbing updates, and HVAC installation. A rare opportunity to bring new life to a true piece of Monticello history! All dimensions are approximate.

340 S Waukeenah St, Monticello

$469,997

MOVE IN READY!! Amazing new construction 3 bedroom 2 bathroom plus office. Luxurious master suite, Kitchen made of dreams, this is a must see!

3 Beds ⋅ 2 Baths ⋅ 399958 MLS

MOVE IN READY!! Amazing new construction 3 bedroom 2 bathroom plus office. Luxurious master suite, Kitchen made of dreams, this is a must see!

51 Tarn Way, Monticello