Jefferson, FL Homes

/42
$510,000 Sold Jun 30, 2025
- 1,898 Sq Ft
- $269/SF
- 18 Days On Market
- 3 Beds
- 2 Baths
- Built 2008
1094 Paul Thompson Rd, Monticello, FL 32344

This beautiful 2008-built home is set on five private acres with a gated entrance and offers 1,898 SQ FT of living space with three bedrooms, two full baths, stainless appliances, lots of windows for natural light, fireplace, and two car garage. Step outside to your own pool oasis with a screened patio overlooking gorgeous oak trees surrounding the property. This property also has a storage shed

Amber Renaud The Nova Group Realty

1094 Paul Thompson Rd, Monticello, FL 32344

/3
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,623 Sq Ft
132 Hilltop Dr, Monticello, FL 32344

132 Hilltop Dr, Monticello, FL 32344

/3
$469,995 Under Contract
- 3 Beds
- 2.5 Baths
- 1,940 Sq Ft
50 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

50 Mire Ct, Monticello, FL 32344
/20
$396,494 Sold Jun 30, 2025
- Land
- 31 Acres
- $12,700 per Acre
- 44 Days On Market
Lot 3 Watermill Rd, Monticello, FL 32344

Absolutely beautiful, 30 acre lot in Jefferson County! This gorgeous piece of heaven is mostly plantation cut with established hardwoods and just waiting for your dream home! The property is high and dry and conveniently located, with easy access to I-10 and 27, making it a quick trip to Tallahassee or Monticello. Road access and a community water tower make building one step easier. Whether

Sarah McKinzie Hum Real Estate

Lot 3 Watermill Rd, Monticello, FL 32344

/31
Est $400,647 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,883 Sq Ft
1613 Yaupon Ct, Monticello, FL 32344

1613 Yaupon Ct, Monticello, FL 32344

/41
$425,000 Under Contract
- 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
/40
$255,000 Sold Jun 30, 2025
- 2,206 Sq Ft
- $116/SF
- 93 Days On Market
- 3 Beds
- 2 Baths
- Built 1914
185 Main St, Monticello, FL 32344

Nestled in the heart of historic Lloyd, this beautiful 1914 Charmer boasts the craftsmanship of an older home with the luxuries of brand new finishes! This Beautiful 3 Bedroom, 2 Bath home has been tastefully remodeled, ready for it's new family. It property possesses 4 new electric fireplaces with brand new tiling throughout. Any couple will enjoy the huge double-head shower with a matching

Lee Hall Capital City Real Estate Group

185 Main St, Monticello, FL 32344

/3
Est $61,000 Not Listed For Sale
420 N Forest Ct, Monticello, FL 32344

420 N Forest Ct, Monticello, FL 32344

/40
$419,900 Under Contract
- 4 Beds
- 2 Baths
- 1,809 Sq Ft
115 Crooked Creek Ln, Monticello, FL 32344

**Buyer backed out because they couldn't get their current home under contract. Home inspection report available! New 2025 Built Home in Crooked Creek on a spacious .72 acre lot! This open plan features 4 bedrooms, 2 bathrooms, 2 car garage, and beautiful shiplap accent walls. The kitchen has a light and bright design with white cabinets, quartz counters, subway tile backsplash, and GE stainless

Amber Renaud The Nova Group Realty

115 Crooked Creek Ln, Monticello, FL 32344
/20
$129,000 Sold Jun 27, 2025
- 936 Sq Ft
- $138/SF
- 117 Days On Market
- 3 Beds
- 1 Bath
- Built 1945
450 W Dogwood St, Monticello, FL 32344

Charming cottage with great potential. 3 bedroom 1 bath with covered front porch in the heart of downtown Monticello. Wood floors in living and bedrooms, tile in kitchen and baths. Carport and shed. Walking distance to downtown restaurants and shopping. Home will need a new roof.

Pam Kelly Kelly & Kelly Properties, Inc

450 W Dogwood St, Monticello, FL 32344

/4
Not Listed For Sale
TBD Blackberry Tr, Monticello, FL 32344

TBD Blackberry Tr, Monticello, FL 32344

/41
$329,500
- 4 Beds
- 2 Baths
- 2,162 Sq Ft
4081 Gamble Rd, Monticello, FL 32344

Nestled on a serene 5-acre retreat, this charming storybook cottage feels like a hidden gem, yet it’s just 15 minutes from downtown Monticello’s quaint shops and restaurants. Tucked back from the road for ultimate privacy, this well-maintained home is surrounded by natural beauty, including native plants, wild azaleas, and lush greenery. Step onto the inviting front porch and into a warm,

Malissa Henning EXP Realty, LLC

4081 Gamble Rd, Monticello, FL 32344
/42
$390,000 Sold Jun 26, 2025
- 1,917 Sq Ft
- $203/SF
- 140 Days On Market
- 3 Beds
- 2 Baths
- Built 1987
1288 Indian Hills Rd, Monticello, FL 32344

Peace is what you will find when you visit this lovely home on 5.66 acres. Mostly wooded with a flowing creek. Brick home has a brand new roof 2025. One owner home that has been meticulously taken care of. Open kitchen /living room with vaulted ceilings and a wood burning stove for cozy evenings. Family room has an office nook an a wall of windows for great outdoor views. The workshop is

Pam Kelly Kelly & Kelly Properties, Inc

1288 Indian Hills Rd, Monticello, FL 32344

/4
Not Listed For Sale
XXXX St Augustine Rd Parcel #2, Monticello, FL 32344

XXXX St Augustine Rd Parcel #2, Monticello, FL 32344

/4
$209,900
- 3 Beds
- 2 Baths
- 1,678 Sq Ft
85 Pine Cone Dr, Monticello, FL 32344

This beautifully renovated 3-bedroom, 2-bathroom modular home offers modern comfort and style. Inside, you'll find granite countertops, all new appliances, and updated finishes with a thoughtful layout perfect for both daily living and entertaining. A brand-new roof was installed in July 2025, and the HVAC system was replaced in October 2021, ensuring long-term peace of mind. Enjoy the outdoors

Gabriela Sacco All Realty Services

85 Pine Cone Dr, Monticello, FL 32344
/42
$525,000 Sold Jun 25, 2025
- 1,907 Sq Ft
- $275/SF
- 16 Days On Market
- 2 Beds
- 2 Baths
- Built 1996
178 Nautilus Dr, Monticello, FL 32344

Introducing an architectural gem poised for a rebirth, this expansive building spanning 12,279 square feet emerges in a state of partial restoration and readiness. Its historical significance and potential for modern ventures converge to offer a unique opportunity. At the heart of this property lies a captivating 70’ diameter circular auditorium, boasting a soaring 41’ high ceiling and crowned

Ondrea Maldonado Hamilton Realty Advisors LLC

178 Nautilus Dr, Monticello, FL 32344

/41
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,160 Sq Ft
660 Whispering Hill, Monticello, FL 32344

660 Whispering Hill, Monticello, FL 32344

/8
$4,500,020
- Land
- 85 Acres
- $52,780 per Acre
0 Big Joe Rd Unit 2025007616, Monticello, FL 32344

Known for its white tail deer, hog and turkey populations, this 85.26 acres in Jefferson County, FL would make a perfect hunting camp. Pristine pine tree property just minutes from Interstate 10 / Exit 225. Ideal Country Estate or weekend get-away. Seller financing available to qualified buyer.

Florie Gage Cornerstone Coastal Properties

0 Big Joe Rd Unit 2025007616, Monticello, FL 32344
/41
$336,000 Sold Jun 23, 2025
- 1,555 Sq Ft
- $216/SF
- 33 Days On Market
- 3 Beds
- 2 Baths
- Built 2021
1600 Sweetbay Ct, Monticello, FL 32344

Beautiful craftsman 2021 built 3/2 home on spacious lot overlooking a wooded green space on a quiet cul-de-sac. Two car garage, granite counters, stainless appliances, laminate wood floors, covered/screened back porch, and fresh landscaping. This home is generator-ready with accessible electrical hookups and HVAC soft start to allow essential comforts during electrical outages. This home is a

Amber Renaud The Nova Group Realty

1600 Sweetbay Ct, Monticello, FL 32344

/11
Not Listed For Sale
XXX Parcel #3 St Augustine Rd, Monticello, FL 32344

XXX Parcel #3 St Augustine Rd, Monticello, FL 32344

/28
$239,000
- 3 Beds
- 2 Baths
- 1,234 Sq Ft
44 Pine Needle Trace, Monticello, FL 32344

Charming Home with Open Floor Plan in Beautiful Monticello, FL! Welcome to this cozy well maintained home featuring an inviting open floor plan, warm wood-burning fireplace and vaulted ceilings that add space and character. French doors off the main living area open to a spacious deck overlooking the backyard. Freshly pained throughout the interior. Seller offering a flooring allowance with

Pam Kelly Kelly & Kelly Properties, Inc

44 Pine Needle Trace, Monticello, FL 32344
/34
$300,000 Sold Jun 20, 2025
- 1,416 Sq Ft
- $212/SF
- 55 Days On Market
- 2 Beds
- 2 Baths
- Built 1993
4014 Ashville Hwy, Monticello, FL 32344

Stunning 10 plus acre property on the Ashville Hwy. This fully renovated 2 bedroom /2 bathroom home offers a cozy, private hideaway draped in Live Oaks, just minutes from historic, downtown Monticello, FL. Renovations include - custom kitchen cabinetry, granite countertops and a light-filled kitchen with sky lights and a corner sink boasting a large window overlooking the property. Custom wood

Barry Kelly Kelly & Kelly Properties, Inc

4014 Ashville Hwy, Monticello, FL 32344

/11
Not Listed For Sale
xxx St Augustine Parcel #4 Rd, Monticello, FL 32344

xxx St Augustine Parcel #4 Rd, Monticello, FL 32344

/46
$178,000
- 3 Beds
- 3 Baths
- 2,635 Sq Ft
18 Perkins Williams Rd, Monticello, FL 32344

Opportunity to finish a traditional-style home on 2.02 acres in the Monticello countryside. Built in 2001 by a local contractor, the home is approximately 80% complete and has never been lived in. The structure needs a new roof, HVAC system, water heater, bedroom flooring, and completion of the master bath. There is visible foundation settlement—cause and extent unknown. Located in a flood

Ashley Hartsfield Keller Williams Town & Country

18 Perkins Williams Rd, Monticello, FL 32344
/30
$349,000 Sold Jun 16, 2025
- 1,680 Sq Ft
- $208/SF
- 72 Days On Market
- 3 Beds
- 2 Baths
- Built 1991
460 W Osprey Ln, Monticello, FL 32344

17 ACRE HOBBY FARM, TINKERER’S DELIGHT, LOTS OF PRIVACY. Includes tractor & equipment, large barn, 7-bay equipment shed, workshop, trove of tools & supplies, greenhouse, half-acre vineyard, fruit trees, multiple garden sites, stocked pond (bream, bass, catfish) fed by one of two wells, cooking/canning/fish-cleaning shed, pasture for horses & livestock, and more. Comfortable, well-maintained 1680

Hines Boyd FL-GA Realty & Auction

460 W Osprey Ln, Monticello, FL 32344

/40
Est $455,227 Not Listed For Sale
- 2 Beds
- 3 Baths
- 1,833 Sq Ft
9255 Gamble Rd, Monticello, FL 32344

9255 Gamble Rd, Monticello, FL 32344

/70
$1,050,000
- 4 Beds
- 4.5 Baths
- 3,696 Sq Ft
825 Rainey Run, Monticello, FL 32344

Welcome to this rare Monticello, FL luxury home for sale on 10 pristine acres with private creek frontage. This 4-bedroom, 4.5-bathroom estate spans nearly 3,700 square feet of elegant living space, offering the perfect blend of privacy, acreage, and modern luxury just minutes from Tallahassee. Property Highlights: 10 acres with a private creek 4 bedrooms, 3 with ensuite bathrooms 3,696 sq. ft.

Renee Dawkins Ketcham Realty Group, Inc.

825 Rainey Run, Monticello, FL 32344
/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

/24
Not Listed For Sale
00 Valley View Rd, Monticello, FL 32344

00 Valley View Rd, Monticello, FL 32344

/70
$989,000
- 4 Beds
- 3 Baths
- 4,600 Sq Ft
2024 Old Lloyd Rd, Monticello, FL 32344

Square footage includes both the main house is 3200 square feet with 4 bedrooms and 3 baths. New barn apartment is 1400 square feet with 2 bedrooms and 1 bath. This would be an amazing income producing property for short and/or long term rental property of barn apt, horse boarding stables ... or even a wedding venue. This breathtaking property checks ALL of the boxes! Please see associated

Katherine Hansli Searcy The Naumann Group Real Estate

2024 Old Lloyd Rd, 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

/5
Not Listed For Sale
0 E Bear Hollow Trail Unit 373231, Monticello, FL 32331

0 E Bear Hollow Trail Unit 373231, Monticello, FL 32331

/43
$295,000
- 3 Beds
- 2 Baths
- 2,044 Sq Ft
300 Cedar St, Monticello, FL 32344

Welcome to 300 Cedar Street ~ Located a stone's throw from Monticello's charming downtown, yet quiet & private ~ Relax in a rocking chair & enjoy sitting on your HUGE 64x8 screened in porch that runs the entire length of the back of the home & overlooks the serene 1.5 acre lot ~ Built in 1958, this single story home is a sturdy brick ranch style with 3 Bedrooms, 2 Baths, extra large attached 2

Jonathan Rigsby Spotlight Real Estate

300 Cedar 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

/14
Est $350,901 Not Listed For Sale
- 2 Beds
4131 Ashville Hwy, Monticello, FL 32344

4131 Ashville Hwy, Monticello, FL 32344

/38
$799,000
- 5,139 Sq Ft
625 E Washington St, Monticello, FL 32344

Amazing Investment Opportunity! Own your piece of history and enjoy some great cash flow in this beautiful Downton Monticello Home. Built in 1888 and almost 4500 SF in the main house with 9 bedrooms, 7 bathrooms and common areas for the tenants. Currently set up as a rooming house with tenants. New roof 2024, new HVAC 2022 and mini splits, New kitchen and bathrooms 2022, Tankless Hot water

Lee Hall Capital City Real Estate Group

625 E Washington St, 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

/5
Not Listed For Sale
000 Taylor Rd, Monticello, FL 32344

000 Taylor Rd, Monticello, FL 32344

/45
$275,000
- 4 Beds
- 2 Baths
- 1,812 Sq Ft
685 E Washington St, Monticello, FL 32344

Perfect brick family home right downtown! Walk to the veggie stand across the street and all the Monticello shops! Renovated 4-bed, 2-bath home. New roof!! New Custom Kitchen cabinets, granite counters, and SS Appliance package perfect for all those home chefs. The open-plan kitchen opens directly into the dining and living room. New Flooring, Paint, Light fixtures, Custom closets and bookcases

Lee Hall Capital City Real Estate Group

685 E Washington St, 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

Showing Results 81 - 120, Page 3 of 18

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