Monticello, FL Homes

/42
$489,900 Under Contract
- 3 Beds
- 2 Baths
- 2,061 Sq Ft
350 Oconee, Monticello, FL 32344

Welcome to Covey Run, a private estate community in the heart of Monticello. Your new 3 bedroom 2 bath 2 car garage sits on 2.24 acres. Home features open floor plan with primary on-suite and large walk-in closet. Kitchen is ready for the chef in mind with gas range and plenty of room for prep. Living room features 10 foot ceilings, fireplace and opens to a sunroom. House has Generac Home

Steve Walker Steve C. Walker Realty, LLC

350 Oconee, Monticello, FL 32344
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/36
$110,000 Sold Jun 16, 2025
- 2,152 Sq Ft
- $51/SF
- 57 Days On Market
- 4 Beds
- 2 Baths
- Built 1920
955 E Pearl St, Monticello, FL 32344

Home to be decided on if it should be restored or torn down. Each person may see it differently as everyone has different opinions. The entire lot size is .77 acres.

Lynette Sirmon All Realty Services

955 E Pearl St, Monticello, FL 32344

/35
Not Listed For Sale
- 2 Beds
- 2 Baths
- 924 Sq Ft
418 Quail Ln, Monticello, FL 32344

418 Quail Ln, Monticello, FL 32344

/41
$519,000
- 3 Beds
- 2 Baths
- 2,170 Sq Ft
282 Long Leaf Dr, Monticello, FL 32344

Enjoy space, privacy, and outdoor living on this well-maintained 5-acre property in Monticello. Tucked away on a private dirt road, this 3-bedroom, 2-bathroom home offers a functional 2,170 square foot layout with plenty of natural light. Outside is where this property really shines—featuring a screened-in patio, a sparkling pool with a Baja shelf, and multiple outdoor entertaining areas

Catherine Hope All Realty Services

282 Long Leaf Dr, Monticello, FL 32344
/35
$375,000 Sold Jun 13, 2025
- 2,768 Sq Ft
- $135/SF
- 24 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1901
925 E Pearl St, Monticello, FL 32344

Charming historic home with bonus guest cottage, located on the most beautiful oak lined street in picturesque Monticello, Florida. OWNER FINANCING AVAILABLE call for convenient terms. Enjoy small-town living in this updated home featuring a 2020 Roof, 2022 HVAC, 2025 Water Heater, Updated Electrical, CPVC and Copper Plumbing, Schedule 40 sewer piping, and mostly updated windows. Relax on the

Tom Grasberger Gaff's Realty Company

925 E Pearl St, Monticello, FL 32344

/24
Est $279,937 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,604 Sq Ft
825 E Dogwood St, Monticello, FL 32344

825 E Dogwood St, Monticello, FL 32344

/28
$420,000 Open Sun 2PM - 5PM
- 3 Beds
- 2.5 Baths
- 2,373 Sq Ft
1205 E Pearl St, Monticello, FL 32344

Charming 1956 Mid-Century Home. Fully Renovated with Modern Touches. Welcome to this beautifully reimagined 1956 classic, where character meets contemporary luxury. Every inch of this home has been thoughtfully renovated, blending original charm with stylish, modern upgrades. Step inside to discover a bright, open-concept living space featuring new floors, recessed lighting, and large windows

Brian Bachman Kelly & Kelly Properties, Inc

1205 E Pearl St, Monticello, FL 32344
/42
$335,000 Sold Jun 10, 2025
- 1,370 Sq Ft
- $245/SF
- 6 Days On Market
- 3 Beds
- 2 Baths
- Built 2021
1535 Willow Rd, Monticello, FL 32344

Like New! Barely lived in Home in the sought-after Crooked Creek Subdivision! Easy commute to Thomasville and Tallahassee with the small-town charm of Monticello! This beautiful 3/2 is on a spacious corner lot and the house is upgraded to include but not limited to stainless steel appliances, recessed lighting, vaulted ceilings, with granite and quartz countertops, and a stunning kitchen island.

Chance Shutes Keller Williams Town & Country

1535 Willow Rd, Monticello, FL 32344

/3
Est $451,072 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,250 Sq Ft
1612 Rabon Rd, Monticello, FL 32344

1612 Rabon Rd, Monticello, FL 32344

/43
$539,000
- 3 Beds
- 2.5 Baths
- 3,054 Sq Ft
79 Lakeside Rd, Monticello, FL 32344

Welcome to your country escape — a timeless farmhouse nestled on 3+ scenic acres, offering the perfect blend of space, charm, and opportunity. This classic home features soaring high ceilings, oversized rooms, and a sprawling wraparound porch that invites you to sit back and soak in the peaceful surroundings. Inside, you’ll find large, light-filled living spaces with original character and room

Michael Schilling Hill Spooner & Elliott Inc

79 Lakeside Rd, Monticello, FL 32344
/25
$307,000 Sold Jun 06, 2025
- 1,584 Sq Ft
- $194/SF
- 51 Days On Market
- 3 Beds
- 2 Baths
- Built 2021
203 Pine Cone Dr, Monticello, FL 32344

Shows like a brand new home, Built in 2021 on half acre lot. Split floor plan with large bedrooms. Open floor plan with kitchen overlooking living space with 10 ft trey ceiling, granite countertops and custom cabinetry. Large master bedroom suite, walk-in shower and walk-in closet. 2 car garage, fenced backyard for the pets and privacy.

Barry Kelly Kelly & Kelly Properties, Inc

203 Pine Cone Dr, Monticello, FL 32344

/24
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,216 Sq Ft
6279 Aucilla Rd, Monticello, FL 32344

6279 Aucilla Rd, Monticello, FL 32344

/47
$459,000
- 3 Beds
- 2 Baths
- 2,334 Sq Ft
1293 Vista Rd, Monticello, FL 32344

Country living at its finest! This beautifully maintained 3-bedroom, 2-bath brick home is nestled on 2.57 peaceful acres—just minutes from Monticello and Interstate 10. Enjoy a desirable split floor plan with hardwood floors throughout the main living areas and new carpeting in the bedrooms. The kitchen features new sparkling quartz countertops, stainless steel appliances, and abundant

Leanne Groom The Naumann Group Real Estate

1293 Vista Rd, Monticello, FL 32344
/39
$425,000 Sold Jun 04, 2025
- 2,822 Sq Ft
- $151/SF
- 28 Days On Market
- 3 Beds
- 2 Baths
- Built 2005
120 Lacapra Rd, Monticello, FL 32344

Beautifully Maintained 2822 SF Home on 1.25 acres- Edge of town living! Enjoy the perfect blend of comfort, space, and convenience in this exceptionally maintained home. Peaceful country living with easy access to all nearby amenities. Step inside to a spacious open concept layout, ideal for everyday living and entertaining. The home features a supersized bonus room perfect for a media room,

Pam Kelly Kelly & Kelly Properties, Inc

120 Lacapra Rd, Monticello, FL 32344

/22
Est $706,013 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,620 Sq Ft
4679 W Washington Hwy, Monticello, FL 32344

4679 W Washington Hwy, Monticello, FL 32344

/38
$575,000
- 3 Beds
- 2.5 Baths
- 2,400 Sq Ft
151 N Ojibwa Rd, Monticello, FL 32344

Spacious, Private, and Ready to Go! This 3-bed, 3-bath home sits on just over 5 acres of agricultural-zoned land, offering space, privacy, and freedom to live how you want. With 2,400 sq ft, there's plenty of room — including a bonus room over the 2-car garage with A/C, a dedicated home office space with an attached bathroom, and an oversized workshop ready for your tools, equipment, or weekend

Clint Bailey Superior Realty Group LLC

151 N Ojibwa Rd, Monticello, FL 32344
/29
$541,000 Sold May 23, 2025
- Land
- 59 Acres
- $9,143 per Acre
- 55 Days On Market
Vacant Hartsfield Rd, Monticello, FL 32344

Picturesque 59.17 Acres of Pasture and Hardwood Bliss Discover your own slice of paradise with this exceptional 59.17-acre property, perfectly nestled just minutes from downtown Monticello, north of Highway 90. This unique offering combines the best of both worlds, showcasing a harmonious blend of lush pastures and majestic hardwoods, creating an ideal landscape for various uses, whether it be

Ben Jones Southern Land & Homes

Vacant Hartsfield Rd, Monticello, FL 32344

/19
Not Listed For Sale
- 2 Beds
- 2 Baths
- 960 Sq Ft
401 E Osprey Ln, Monticello, FL 32344

401 E Osprey Ln, Monticello, FL 32344

/61
$589,900
- 4 Beds
- 3 Baths
- 2,660 Sq Ft
513 Creekside Ct, Monticello, FL 32344

Custom home built by Kessler Construction on 2 full acres in desirable Crook Creek subdivision~4 bedrooms/3 full baths~gourmet kitchen~split bedroom plan~luxury master bath~incredibly high ceilings~42x14 screened porch~oversized 2-car garage~located on a cul-de-sac, this home offers peaceful privacy

Renee Smawley Steve C. Walker Realty, LLC

513 Creekside Ct, Monticello, FL 32344
/11
$95,000 Sold May 15, 2025
- Land
- 10 Acres
- $9,082 per Acre
- 170 Days On Market
0 E Glenn Rd, Monticello, FL 32344

Have you ever dreamed of building a home on several acres? Here is your chance to snag your slice of quaint, peaceful living, on more than 10 acres! Build the home of your dreams and there's even space to build an additional dwelling unit like a pool home, mother-in-law suite, etc. The possibilities on this beautiful land are endless.

Danielle Andrews Realty One Group Next Gen

0 E Glenn Rd, Monticello, FL 32344

/18
Est $256,399 Not Listed For Sale
- 5 Beds
- 2 Baths
- 1,728 Sq Ft
622 Limestone Rd, Monticello, FL 32344

622 Limestone Rd, Monticello, FL 32344

/42
$614,900
- 3 Beds
- 2.5 Baths
- 2,560 Sq Ft
181 Heritage Blvd, Monticello, FL 32344

Craftsman style house in Heritage Hills subdivision~ Seller contemplating backup contracts~ The house features 3 bedrooms/2 bathrooms and is energy efficient (Green Certified) ~ Luxurious hardwood flooring and a deluxe primary bathroom with separate jetted tub & large shower ~ Custom built-in cabinets in the living room and office ~ Regal craftsman style interior trim throughout and

Mariela Bartens Coldwell Banker Hartung

181 Heritage Blvd, Monticello, FL 32344
/3
$2,989,892 Sold May 12, 2025
- Land
- 420 Acres
- $7,119 per Acre
- 87 Days On Market
0 Bassett Dairy Rd Unit 380760, Monticello, FL 32344

Additional 420 acres to add to MLS listing 373105 which is 450 acres. May be purchased separately or together. Land has been in the family over 50 years. Beautiful rolling topography of crop land, pasture and timber. Elevation of 260 ft. above sea level. Water elements to enjoy.

Brian Proctor NAI TALCOR Commercial

0 Bassett Dairy Rd Unit 380760, Monticello, FL 32344

/31
Est $130,351 Not Listed For Sale
- 3 Beds
821 Old Lloyd Rd Unit 2, Monticello, FL 32344

821 Old Lloyd Rd Unit 2, Monticello, FL 32344

/37
$465,000
- 4 Beds
- 3 Baths
- 2,076 Sq Ft
376 Tecumseh Rd, Monticello, FL 32344

BRAND NEW ROOF!! Gorgeous multigenerational, ranch style, 4 Bedroom/3 Bath home with 5th room that can be used as an office or additional bedroom. Perfect for a growing or downsizing family! Home rests on 4.60 acres of outdoor, partially wooded paradise. Enjoy tranquility from the all-season rear porch-removable panels allow you to turn room into a screened porch in minutes. Many recent updates

Casey Skelton Pearson Realty Inc.

376 Tecumseh Rd, Monticello, FL 32344
/8
$3,069,542 Sold May 12, 2025
- Land
- 450 Acres
- $6,821 per Acre
- 284 Days On Market
0 Bassett Dairy Rd Unit 373105, Monticello, FL 32344

450 acres that has been in the family for over 50 years. Beautiful rolling topography of crop lands, pasture and timber. Elevation of 260 ft. above sea level. Water elements to enjoy. Adjacent 420 acres can be purchased for $3,150,000, see listing Number 380760, beautiful 870 acres total

Brian Proctor NAI TALCOR Commercial

0 Bassett Dairy Rd Unit 373105, Monticello, FL 32344

/5
Est $125,282 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,314 Sq Ft
220 Horseshoe Rd, Monticello, FL 32344

220 Horseshoe Rd, Monticello, FL 32344

/41
$425,000
- 5 Beds
- 4 Baths
- 3,330 Sq Ft
4131 N Jefferson Hwy, Monticello, FL 32344

3330 square foot home on a beautiful 6 acre property that backs up to Pine Haven Plantation! This is a solid brick home with a 2016 metal roof and a 2018 HVAC unit and well pump. The home was purchased back in 2023 and gutted along with some extensive repairs done to bones of the home. It is now waiting for the perfect person to come in and finish her out with their personal touches. The main

Catherine Hope All Realty Services

4131 N Jefferson Hwy, Monticello, FL 32344
/42
$900,000 Sold May 08, 2025
- 2,750 Sq Ft
- $327/SF
- 38 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2018
542 Tradition Way, Monticello, FL 32344

Stunning 3 BR 2.5 Bath custom pool home offering elegance and comfort. Situated on 7 landscaped and manicured acres, fenced and cross fenced. Meticulously maintained both inside and out. 10 ft ceilings, 8 ft doors, large windows, with upscale finishes throughout. Gourmet kitchen equipped with premium appliances, ample custom cabinets, spacious island with plenty of counters for entertaining.

Pam Kelly Kelly & Kelly Properties, Inc

542 Tradition Way, Monticello, FL 32344

/30
Est $529,555 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,016 Sq Ft
3214 Tram Rd, Monticello, FL 32344

3214 Tram Rd, Monticello, FL 32344

/24
$430,000 New Construction
- 3 Beds
- 2 Baths
- 1,865 Sq Ft
173 Deerfield Ln, Monticello, FL 32344

Welcome to this beautifully maintained 3-bedroom, 2-bath home offering the perfect blend of peaceful country living and modern upgrades. Nestled on a full acre of land, this charming property is a rare gem with no HOA restrictions—giving you the freedom to truly make it your own. Step inside and be captivated by the open and inviting floor plan, featuring both a formal living room and a cozy

Pamela Jordan-williams Superior Realty Group LLC

173 Deerfield Ln, Monticello, FL 32344
/10
$80,000 Sold May 05, 2025
- 782 Sq Ft
- $102/SF
- 27 Days On Market
- 2 Beds
- 1 Bath
- Built 1955
895 Independent St, Monticello, FL 32344

Charming cottage, affordable living under $100,000. Small lot for easy maintenance. New split ac unit. New roof, windows, flooring, new insulation in attic, and new appliances. Potential Owner financing $10,000 down, 6% interest, 3 year balloon.

Barry Kelly Kelly & Kelly Properties, Inc

895 Independent St, Monticello, FL 32344

/28
Est $381,745 Not Listed For Sale
- 3 Beds
- 2 Baths
- 3,328 Sq Ft
129 Indian Hills Rd, Monticello, FL 32344

129 Indian Hills Rd, Monticello, FL 32344

/3
$469,995 New Construction
- 3 Beds
- 2.5 Baths
- 1,940 Sq Ft
52 Mire Ct, Monticello, FL 32344

Amazing new construction 3 bedroom 3 bathroom by Nailed It Tallahassee LLC Come pick out all your finishes, home scheduled for completion August 2025. Luxurious master suite, Kitchen made of dreams, this is a must see! Preferred Lender offering 1% in closing costs! Photos of previous home come make this one your own!

Amber McKinney Hamilton Realty Advisors LLC

52 Mire Ct, Monticello, FL 32344
/42
$529,900 Sold Apr 30, 2025
- 1,868 Sq Ft
- $284/SF
- 16 Days On Market
- 3 Beds
- 2 Baths
- Built 2017
273 Legacy Way, Monticello, FL 32344

Stunning 2017 built home on 3.03 acres with mature trees on all sides for incredible privacy! This home features 3 bedrooms, 2 bathrooms, and a 2-car garage. Gorgeous design finishes include granite counters, stainless appliances, custom cabinets, built-in entertainment center with shiplap accent, craftsman style trim and crown molding, covered back porch with brick paver floor, and stone accents

Amber Renaud The Nova Group Realty

273 Legacy Way, Monticello, FL 32344

/38
Est $154,528 Not Listed For Sale
- 2 Beds
- 1 Bath
- 912 Sq Ft
310 N Olive St, Monticello, FL 32344

310 N Olive St, Monticello, FL 32344

/41
$460,995 New Construction
- 3 Beds
- 2 Baths
- 1,806 Sq Ft
47 Mire Ct, Monticello, FL 32344

Amazing new construction 3 bedroom 2 bathroom by Nailed It Tallahassee LLC Come pick out all your finishes, home scheduled for completion August 2025. Luxurious master suite, Kitchen made of dreams, this is a must see! Preferred Lender offering 1% in closing costs! Photos of previous home come make this one your own!

Amber McKinney Hamilton Realty Advisors LLC

47 Mire Ct, Monticello, FL 32344
/42
$449,000 Sold Apr 30, 2025
- 3,635 Sq Ft
- $124/SF
- 80 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1842
340 E Washington St, Monticello, FL 32344

Step into the timeless elegance of the Simpkins-Bailey House, a distinguished circa 1854 residence nestled in the heart of Monticello's Historic District. This 3-bedroom, 3.5-bathroom home offers 3,635 square feet of meticulously updated living space, seamlessly blending historic charm with modern comforts. Zoned for business-residential use, the property provides incredible flexibility for a

Sandy Ferrera All County Suncoast Property

340 E Washington St, Monticello, FL 32344

/36
Est $654,777 Not Listed For Sale
- 4 Beds
- 3 Baths
- 5,556 Sq Ft
250 Hiawatha Farms Rd, Monticello, FL 32344

250 Hiawatha Farms Rd, Monticello, FL 32344

/70
$425,000 Under Contract
- 2 Beds
- 2 Baths
- 1,452 Sq Ft
1291 Hayfield Spur, Monticello, FL 32344

Escape to your own private retreat in Monticello, FL! This spacious 5-acre property features two private ponds and two large outbuildings—both equipped with utilities. One outbuilding functions as a workshop with additional storage and a bathroom, offering endless potential. The 2-bedroom, 2-bathroom home is full of charm, featuring vaulted ceilings, a wood-burning fireplace, and an abundance of

Jason Naumann The Naumann Group Real Estate

1291 Hayfield Spur, Monticello, FL 32344

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