Jefferson, FL Homes

/42
$339,000
- 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
/13

Call for Price

Jefferson Pines

1 Bed

24 Parkway Pines, Monticello, FL 32344

24 Parkway Pines, Monticello, FL 32344
/70
$425,000 Sold Aug 08, 2025
- 1,452 Sq Ft
- $293/SF
- 26 Days On Market
- 2 Beds
- 2 Baths
- Built 2009
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

/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

/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
/17
$1,500 per month
- 3 Beds
- 2 Baths
- 1,476 Sq Ft
- House for Rent
635 N Wirick St, Monticello, FL 32344

This newly remodeled 3-bedroom, 2-bath house is located in a quiet neighborhood within the city limits of Monticello. It features a spacious fenced yard, ideal for outdoor activities. The rent is affordable at $1,500 per month. The home includes a laundry area and pantry for added convenience. Available from 8/11/25, the property is smoke-free and does not allow pets inside. Renters are

Cecilia Williams-Crumitie 1st Realty Appraisal Inc

635 N Wirick St, Monticello, FL 32344
/7
$95,000 Sold Aug 01, 2025
- Land
- 5 Acres
- $18,375 per Acre
- 102 Days On Market
0 Taylor Rd Unit 384618, Monticello, FL 32344

5.17 acres Taylor Rd. Wonderful Jefferson County location. Minutes from I-10/ Gamble Rd. + downtown Monticello. New 5 lot mini subdivision paved frontage, minimal restrictions to protect values. See survey and site plans in associated docs. Underground County water available. Owner financing available. LAST LOT FOR SALE!

Kevin Davis The Naumann Group Real Estate

0 Taylor Rd Unit 384618, 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

/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
/24
$2,000 per month
- 3 Beds
- 2 Baths
- 1,650 Sq Ft
- House for Rent
170 W Cherokee St, Monticello, FL 32344

We have owned this home for 15 years. It was fully remodeled one year ago. It has a new roof, insulation, HVAC including ductwork, new drywall, new ceilings, light fixtures, plumbing, electrical. New kitchen and baths. Large corner lot. Walk to the grocery store. This is a new home with older home charm. Original oak floors in most of the house, fireplace. Home is also for sale at 255,000.

Ken Foster FosterGrant Real Estate, LLC

170 W Cherokee St, Monticello, FL 32344
/30
$270,000 Sold Jul 31, 2025
- 1,800 Sq Ft
- $150/SF
- 22 Days On Market
- 1 Bed
- 1.5 Baths
- Built 2009
358 Pineview Rd, Monticello, FL 32344

Barn style home, approx. 1100 sq ft living area with approx. 1400 sq feet workshop area all under one roof. Combination living/kitchen/dining with gas fireplace. Large master suite with walk-in closet. Screen porch and additional 11x 58 overhang for equipment storage. 2.93 acres half open and half wooded. Measurements are all approx.

Barry Kelly Kelly & Kelly Properties, Inc

358 Pineview Rd, Monticello, FL 32344

/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

/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
/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
/8
$35,000 Sold Jul 30, 2025
- Land
- 5.00 Acres
- $7,000 per Acre
- 341 Days On Market
1024 Vista Rd, Monticello, FL 32344

CREEK, BUILDING SITE NEAR ROAD, WOODS TO HUNT, NEAR MONTICELLO. This property is dominated by a mostly walkable wetland corridor connected to nearby land, making it attractive for hunting. There's a building site adjacent to Vista Road at the front of the land. Build what you want; no HOA or restrictive covenants. Mobile homes okay. Near charming Monticello; convenient to Tallahassee just

Heather Boyd FL-GA Realty & Auction

1024 Vista Rd, Monticello, FL 32344

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

115 Timber Trace, 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
$415,000 Sold Jul 28, 2025
- 2,832 Sq Ft
- $147/SF
- 89 Days On Market
- 4 Beds
- 3 Baths
- Built 1987
4710 Waukeenah Hwy, Monticello, FL 32344

Monticello living is good, peaceful living. This home is ready for a multi-generational family, or a family with loads of relatives and friends to entertain. This three bedroom, two bath home has an adjacent mother in law suite complete with bedroom, kitchen, bath and living room. Located on two acres with a 2025 a/c unit, 2019 roof, large screened and unscreened porch, 3 pad carport, 3

Fay Armstrong Keller Williams Town & Country

4710 Waukeenah Hwy, Monticello, FL 32344

/5
Est $113,858 Not Listed For Sale
150 Georgia St, Monticello, FL 32344

150 Georgia St, Monticello, FL 32344

/31
$55,000
- Land
- 8 Acres
- $7,152 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
/38
$280,000 Sold Jul 25, 2025
- 1,056 Sq Ft
- $265/SF
- 58 Days On Market
- 2 Beds
- 2 Baths
- Built 2002
Unlisted Address

Private Hunting Retreat on 20 Secluded Acres Just 25 minutes from Florida's Gulf Coast! Escape to your own slice of paradise with this private ,fully-equipped 20 acre property- ideal for hunters, or anyone seeking peace and privacy! Tucked away and surrounded by nature, this property offers the ultimate getaway with hunt-on-your-own-land freedom and thoughtful amenities designed for outdoor

Pam Kelly Kelly & Kelly Properties, Inc

Unlisted Address

/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

/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
/42
$459,000 Sold Jul 25, 2025
- 2,555 Sq Ft
- $180/SF
- 143 Days On Market
- 4 Beds
- 3 Baths
- Built 1983
4287 Bassett Dairy Rd, Monticello, FL 32344

Rare COUNTRY Farmhouse OASIS AWAITS! – Discover the perfect blend of rustic charm in this stunning 5-bedroom, 3-bathroom home, nestled on five fully fenced acres of picturesque pastureland. Located just 15 minutes from downtown Monticello, this peaceful retreat offers breathtaking views, abundant wildlife, and plenty of space for your pets to roam. Step inside to a beautifully updated,

Destiny Jones Keller Williams Town & Country

4287 Bassett Dairy Rd, Monticello, FL 32344

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

00 Big Joe Rd, Monticello, FL 32344

/38
$419,000
- 3 Beds
- 3 Baths
- 2,706 Sq Ft
339 Silver Lake Rd, Monticello, FL 32344

Gorgeous home on 5 acres mostly pasture. Open concept with vaulted ceilings; great entertainment/family home. Private setting; must see to believe.

Steve Walker Steve C. Walker Realty, LLC

339 Silver Lake Rd, Monticello, FL 32344
/26
$130,000 Sold Jul 25, 2025
- Land
- 14 Acres
- $9,220 per Acre
- 175 Days On Market
00 Cardinal Ln, Monticello, FL 32344

This property is located at the dead-end of Cardinal Lane, on a cul-de-sac, in the Lloyd Acres Subdivision (NO HOA). It's zoned Residential-01, and can be subdivided (1 home/1 acre). Some wetland spots exist, but there is plenty of room for (1) or more future home-sites. Property was partially cleared for a future home-site by the current owners, but they've since decided to stay in their current

Brenna Kelly-Ward Kelly & Kelly Properties, Inc

00 Cardinal Ln, Monticello, FL 32344

/25
Est $217,900 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
$487,878
- Land
- 122 Acres
- $3,999 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
$335,000 Sold Jul 24, 2025
- 1,551 Sq Ft
- $216/SF
- 45 Days On Market
- 4 Beds
- 2 Baths
- Built 2012
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.

580 Holly Rd, Monticello, FL 32344

/3
Not Listed For Sale
00 Fountain Dr, Monticello, FL 32344

00 Fountain Dr, Monticello, FL 32344

/18
$1,100,000
- Land
- 200 Acres
- $5,500 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
/6
$195,000 Sold Jul 21, 2025
- Land
- 4.00 Acres
- $48,750 per Acre
- 215 Days On Market
tbd Gamble Rd, Monticello, FL 32344

Mixed Use Suburban/Residential zoning, just south of I-10 Exit 217. Some clearing has been done. Several parcels make up this listing. A survey is needed to determine the exact acreage and distances. Current distances are approx. There is a drain that runs through a portion of the property making some of it wet.

Barry Kelly Kelly & Kelly Properties, Inc

tbd Gamble 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
/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

/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
$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

/12
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,344 Sq Ft
509 Waukeenah Hwy, Monticello, FL 32344

509 Waukeenah Hwy, Monticello, FL 32344

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