Jefferson, FL Homes

/42
$335,000 Pending
- 4 Beds
- 2 Baths
- 1,551 Sq Ft
580 Holly Rd, Monticello, FL 32344

Looking for that small town life but still wanting to be close to Tallahassee? This is it! The quiet neighborhood of Crooked Creek subdivision could be the place for you! Located just outside of Monticello, FL. this roomy 4 bedroom, 2 bathroom 2012 built one owner house has it all. Beautifully land scaped yard with two gazebos and a greenhouse. Vaulted ceilings in the main living area and large

Anthony Gifford

Ketcham Realty Group, Inc.

(850) 616-7294

580 Holly Rd, Monticello, FL 32344
/13

Call for Price

Jefferson Pines

1 Bed

24 Parkway Pines, Monticello, FL 32344

24 Parkway Pines, Monticello, FL 32344
/27
$349,900 Sold Jul 18, 2025
- 1,601 Sq Ft
- $219/SF
- 106 Days On Market
- 3 Beds
- 2 Baths
- Built 2025
149 Coopers Pond Rd, Monticello, FL 32344

New build, under construction on 1.05 acres, close to downtown Monticello and no HOA!! Five mins to I-10 and four mins to US90. Completion date set for April 2025 - - > see similar new build, under construction @ 81 Coopers Pond on 2.62 acres @ $399,900. Highlights of builder specs are as followed: - 1601sqft - 3 bedrooms - 2 full baths - 10' tray ceiling in living room - LVP throughout -

Tiffany Kasdorf The Nova Group Realty

149 Coopers Pond Rd, Monticello, FL 32344

/39
Est $1,419,888 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 4,040 Sq Ft
25 Tallamont Rd, Monticello, FL 32344

25 Tallamont Rd, Monticello, FL 32344

/31
$60,000
- Land
- 8 Acres
- $7,802 per Acre
983 Mays Rd, Lamont, FL 32344

Affordable recreational parcel! Buy now, build later. Ultimate weekend escape or future homestead offering fun, freedom and fresh air- 7.69 serene acres split on both sides of scenic Mays Road. Enjoy the best of two offerings: West side 5.3 acres +/- with the pond, partially cleared with lush pasture, mature shade trees and wide-open space, perfect for horses, livestock, camping, four wheeling,

Lynette Sirmon

All Realty Services

(850) 752-4623

983 Mays Rd, Lamont, FL 32344
/18
$1,800 per month
- 3 Beds
- 2 Baths
- 2,112 Sq Ft
- House for Rent
80 Capri Ln, Monticello, FL 32344

Come see this brand new contrition move in ready home today.

Amber McKinney Hamilton Realty Advisors LLC

80 Capri Ln, Monticello, FL 32344
/20
$360,000 Sold Jul 11, 2025
- Land
- 31 Acres
- $11,531 per Acre
- 26 Days On Market
Lot 4 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 4 Watermill Rd, Monticello, FL 32344

/42
Est $198,000 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,680 Sq Ft
3908 N Salt Rd, Monticello, FL 32344

3908 N Salt Rd, Monticello, FL 32344

/42
$349,000
- 4 Beds
- 4 Baths
- 3,456 Sq Ft
852 E Buckhorn Trail, Greenville, FL 32331

Welcome to Your Hidden Hilltop Retreat! Perched atop a gentle rise (180 ft. above sea level) in Northeast Jefferson County, this three-story, 4-bedroom, 4-bathroom sanctuary offers a life lived deeply in tune with nature. Nestled on 5.11 acres of whimsical, lovingly tended land—where white-tailed deer browse the edges of a fenced garden and wild turkeys meander past the first floor, screened

Lynette Sirmon

All Realty Services

(850) 930-1972

852 E Buckhorn Trail, Greenville, FL 32331
/12
$1,200 per month
- 3 Beds
- 2 Baths
- 1,352 Sq Ft
- House for Rent
1640 Cherry Tree Rd, Monticello, FL 32344

3/2 HOME ON 2.4 ACRES NEAR WAUKEENAH. Just 18 minutes from Capital Circle out Apalachee Pwky. Backs up to Turner’s Avalon Plantation. Hugh front porch with swing, overlook spacious front yard. Comfy, well maintained 1300+ s.f. manufactured home with central air & heat, utility room with washer & dryer hookups. No pets or smokers, please. $1,200/month. Rental application required.

Hines Boyd FL-GA Realty & Auction

1640 Cherry Tree Rd, Monticello, FL 32344
/14
$179,000 Sold Jul 11, 2025
- 1,620 Sq Ft
- $110/SF
- 360 Days On Market
- 3 Beds
- 2 Baths
- Built 2002
120 E 1st Place, Greenville, FL 32331

These pictures were done before the building was tenant occupied.* Come see this large, high and dry 5 acre homestead. This home has a newer roof and AC unit. It sports brand new appliances, counter tops, vinyl plank flooring and cabinets. Surrounded by stunning oak trees and full of wildlife.

Caleb Stephens Silo Hill Properties

120 E 1st Place, Greenville, FL 32331

/36
Est $491,545 Not Listed For Sale
- 5 Beds
- 3 Baths
- 2,552 Sq Ft
874 Lake Rd, Monticello, FL 32344

874 Lake Rd, Monticello, FL 32344

/21
$349,000
- Land
- 15 Acres
- $23,267 per Acre
0000 Waukeenah Hwy, Monticello, FL 32344

This stunning 15 acre property offers a mix of open land and wooded areas, providing a serene and private setting. Approximately 2 acres are equipped with an irrigation system, ideal for gardening, landscaping or small farming. This property includes a well-maintained barn with four spacious horse stables, perfect for equestrian enthusiasts. Power, well, and septic are already in place, making

Shanna D'Attile

Keller Williams Town & Country

(850) 809-9683

0000 Waukeenah Hwy, Monticello, FL 32344
/4
$1,050 per month
- 1 Bed
- 1 Bath
- 4,439 Sq Ft
- House for Rent
625 E Washington St, Monticello, FL 32344

First floor of a historic Mansion nestled in downtown Monticello. Utilities and internet included. Off street parking with dedicated parking space. This room boasts 11ft ceilings with a private ensuite . Tenant will have access to common areas such as living and dining room, along with shared laundry. Private mini split A/C and heat included.

Lee Hall Capital City Real Estate Group

625 E Washington St, Monticello, FL 32344
/4
$80,000 Sold Jul 08, 2025
- Land
- 4.42 Acres
- $18,100 per Acre
- 78 Days On Market
TBD Devane, Monticello, FL 32344

Wooded 4.42 acres, peaceful location just on the outside of Monticello. Across from the Jefferson County Country Club.

Barry Kelly Kelly & Kelly Properties, Inc

TBD Devane, Monticello, FL 32344

/15
Not Listed For Sale
115 Timber Trace, Monticello, FL 32344

115 Timber Trace, Monticello, FL 32344

/3
$127,500
- Land
- 51 Acres
- $2,500 per Acre
000 Kinsey Rd, Monticello, FL 32344

51 Acres of prime hunting/recreational land. Paved road access with owned easement. Wolf creek runs thrugh part of the property. $2500/Acre

Buddy Witmer

Steve C. Walker Realty, LLC

(850) 726-3832

000 Kinsey Rd, Monticello, FL 32344
/4
$6,000 Sold Jul 08, 2025
- Land
- 0.25 Acre
- $24,000 per Acre
- 91 Days On Market
TBD Hangar Ln, Greenville, FL 32331

Hangar lots, each lot approx 50 x 75, The plan was for plane storage but they can be used for other storage possibilities. The lots are cleared. The measurements are approx. Over 6000 ft grass runway.

Barry Kelly Kelly & Kelly Properties, Inc

TBD Hangar Ln, Greenville, FL 32331

/5
Est $116,889 Not Listed For Sale
150 Georgia St, Monticello, FL 32344

150 Georgia St, Monticello, FL 32344

/17
$24,997 Pending
- Land
- 0.86 Acre
- $29,066 per Acre
98 Cox Rd, Monticello, FL 32344

Small, tract of land "bring the chickens, build a chicken coop" located between Monticello, FL and Thomasville, GA. This UNIQUE, .86 acres of land with its deeply, rich, flora and native fauna is thick and abundant with many different types of indigenous species. Use the 10x20 storage building as a primitive bunkhouse cabin, specimen container, wildlife observatory or weekend landing pad/fun

Lynette Sirmon

All Realty Services

(850) 990-4427

98 Cox Rd, Monticello, FL 32344
/34
$437,000 Sold Jul 07, 2025
- 2,472 Sq Ft
- $177/SF
- 19 Days On Market
- 3 Beds
- 2 Baths
- Built 2014
327 Kims Ln, Lamont, FL 32336

Escape to the serenity of the countryside with this beautifully maintained and well constructed 2014 home nestled on 5.24 acres. Designed with comfort and functionality in mind, picturesque pasture and mature woods. One owner property offers and inviting open floor plan that seamlessly blends indoor and outdoor living. Enjoy mornings on the 600 sq. ft. sun porch, or unwind on the wraparound

Barry Kelly Kelly & Kelly Properties, Inc

327 Kims Ln, Lamont, FL 32336

/36
Est $251,059 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,514 Sq Ft
415 S Cherry Ct Unit 4, Monticello, FL 32344

415 S Cherry Ct Unit 4, Monticello, FL 32344

/8
$22,000
- Land
- 1.18 Acres
- $18,644 per Acre
874 Flatwoods, Monticello, FL 32344

A square 1.18 acres with paved road frontage. It has a powerline easement that runs through the center of the property. It has several, abandoned, old mobile homes on the property (no titles will be given, only bill of sale) and other structures. It has about 50% wet lands and a portion of the property lies within the flood zone. It is wooded, with some, young, easy to mulch, growth and some

Lynette Sirmon

All Realty Services

(448) 218-0926

874 Flatwoods, Monticello, FL 32344
/42
$193,000 Sold Jul 02, 2025
- 2,088 Sq Ft
- $92/SF
- 30 Days On Market
- 4 Beds
- 2 Baths
- Built 2015
285 E 10th Way, Greenville, FL 32331

Welcome to your serene retreat in Greenville on over 5 acres, this well-appointed 2015 manufactured home offers over 2,000 sq ft of thoughtfully designed living space. Inside, you’ll find a flowing open floor plan with luxury vinyl tile throughout (ZERO CARPET), two expansive living areas- ideal for entertaining or relaxing. A generously sized primary suite complete with a spa-style ensuite. The

Michael Phillips Engel & Völkers Tallahassee

285 E 10th Way, Greenville, FL 32331

/16
Not Listed For Sale
00 Big Joe Rd, Monticello, FL 32344

00 Big Joe Rd, Monticello, FL 32344

/42
$469,000
- 5 Beds
- 2 Baths
- 2,184 Sq Ft
10283 Ashville Hwy, Greenville, FL 32331

Amazing opportunity to own this private solar-powered farm with a large house! Beautiful and serene 16 acres with fruit trees, fields, lots of horse potential and 40 solar panels less than 5 years old. Nearly free electric! 5 Bedroom, 2 Bath with Large Eat-in Kitchen, Stainless Steel Appliances, Huge Great Room, Beautiful Hardwood Floors throughout main floor of the house, TWO Large Screened-in

Lee Hall Capital City Real Estate Group

10283 Ashville Hwy, Greenville, FL 32331
/20
$82,500 Sold Jul 02, 2025
- Land
- 5.00 Acres
- $16,500 per Acre
- 30 Days On Market
91 W 7th Way, Greenville, FL 32331

Selectively cleared 5 acres in the agricultural and residential area of Jefferson Landing. This fly-in subdivision is flanked by Sneads Hideaway and Ashville Highlands. The buildable parcel is easily accessible with road frontage on two sides, Deerwood Boulevard and W 7th Way. This property is approximately one mile off scenic Ashville Highway and close to the Aucilla River and the Jefferson

Heather Rybak Rybak Realty, LLC

91 W 7th Way, Greenville, FL 32331

/25
Est $217,603 Not Listed For Sale
- 1 Bed
- 1.5 Baths
- 802 Sq Ft
293 Freeman Rd, Lamont, FL 32336

293 Freeman Rd, Lamont, FL 32336

/16
$609,878
- Land
- 122 Acres
- $4,999 per Acre
0 James Noble Rd, Greenville, FL 32331

Millwood Timberland East is a balanced property located in a great recreational market. The Ashville area is home to numerous trophy grade recreational properties and is known for exceptional whitetail, turkey and waterfowl hunting. This property features an efficient footprint with good access and internal road infrastructure. The uplands are planted with slash pine that are approximately 8

Bryant Peace Saunders Real Estate

0 James Noble Rd, Greenville, FL 32331
/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
00 Fountain Dr, Monticello, FL 32344

00 Fountain Dr, Monticello, FL 32344

/18
$1,300,000
- Land
- 200 Acres
- $6,500 per Acre
0 Gum Swamp, Greenville, FL 32331

Millwood Timberland West is a balanced recreational asset located in the Ashville, FL region. The internal road system meanders through the ecologically diverse landscape of pine plantations, live oaks and forested wetlands. The uplands are planted in slash pine that are approximately 15 years old and ready to be thinned. The next owner will be able to thin the pines to their specification in

Bryant Peace Saunders Real Estate

0 Gum Swamp, Greenville, FL 32331
/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

/9
Est $170,241 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,620 Sq Ft
2191 Rabon Rd, Monticello, FL 32344

2191 Rabon Rd, Monticello, FL 32344

/42
$1,125,000
- 3 Beds
- 1 Bath
- 1,146 Sq Ft
740 Kinsey Rd, Monticello, FL 32344

Location: Jefferson County, FL Size: 155 acres Features: Rolling pastures Planted pines Natural hardwoods Pond Home: 1941 built 1,146 square feet Updated Outbuildings: With power Opportunities for workshops, storage, and more Additional Homesites: Breathtaking views Peaceful living Proximity: 10 miles from downtown Monticello, FL 5 miles to I-10 Wildlife: Deer Turkey Waterfowl

Ben Jones Southern Land & Homes

740 Kinsey Rd, 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

/23
Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,800 Sq Ft
5585 Turkey Scratch Rd, Monticello, FL 32344

5585 Turkey Scratch Rd, Monticello, FL 32344

/20
$570,000
- Land
- 71 Acres
- $8,028 per Acre
0 Aucilla Rd Unit 22696476, Monticello, FL 32344

Located on Aucilla Rd in Monticello, FL, this versatile AG-5 property offers endless potential for residential, agricultural, and recreational use. The upland portion has been cleared, making it ideal for a homesite or multiple residences, with zoning allowing one unit per five acres and options for family transfers under county guidelines.For those looking to enjoy North Floridas natural

Jeremiah Thompson Saunders Land

0 Aucilla Rd Unit 22696476, 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

/26
Est $309,869 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,648 Sq Ft
560 E 6th Way, Greenville, FL 32331

560 E 6th Way, Greenville, FL 32331

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