Jefferson, FL Homes

/42
$449,000
- 3 Beds
- 2 Baths
- 1,921 Sq Ft
2497 Boston Hwy, Monticello, FL 32344

Charming Hillside Country Retreat with Barn and Acreage. Welcome to your dream countryside escape! This beautifully maintained brick home sits peacefully on a hillside, surrounded by sprawling fields dotted with mature pecan trees. Inside, the home features a spacious open floor plan, perfect for entertaining or relaxing with family. The large kitchen offers ample workspace and storage, while the

Pam Kelly Kelly & Kelly Properties, Inc

2497 Boston Hwy, Monticello, FL 32344
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/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

/24
Est $275,435 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

/39
$635,000
- 3 Beds
- 2.5 Baths
- 2,546 Sq Ft
181 Heritage Blvd, Monticello, FL 32344

Highly Desirable Heritage Hills Location! Enjoy the perfect blend of privacy and convenience with this Craftsman-style home located on 3 serene acres, offering an easy commute to both Tallahassee and Monticello. The like-new residence boasts high-end finishes throughout, including crown molding, coffered ceilings, wainscoting, and a cozy gas fireplace. Relax or entertain year-round on the

Pam Kelly Kelly & Kelly Properties, Inc

181 Heritage Blvd, 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

/3
Est $446,252 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

/34
$499,000
- 8 Beds
- 4 Baths
- 4,806 Sq Ft
2664 W Washington Hwy, Monticello, FL 32344

FULLY RENOVATED TWO HOUSES, 1.9 acres, on picturesque US 90 near Monticello. UNDER $99/SF! These move-in-ready homes in good condition have a total of 8 bedrooms, 4 baths, and 4,806 s.f. living area. The MAIN HOUSE is a 1950’s era brick ranch-style home with new plumbing, new electric, fresh paint, new roof, whole home generator. Great opportunity for multiple generations to live side by side, or

Heather Boyd FL-GA Realty & Auction

2664 W Washington Hwy, Monticello, FL 32344
/17
$110,000 Sold Jul 31, 2025
- Land
- 11 Acres
- $9,848 per Acre
- 310 Days On Market
55 W Cavallo Trail, Monticello, FL 32344

Discover the allure of natural serenity with this captivating vacant property, an ideal canvas for your dream home. Nestled in a quiet, secluded subdivision, this spacious 11.1 acre plot boasts mature oak trees and a thoughtfully cleared homesite, providing an enchanting woodland backdrop combined with the readiness to build. What truly sets this property apart is its convenience coupled with

Tully Sparkman Bluewater Realty Group

55 W Cavallo Trail, 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

/39
$539,000
- 3 Beds
- 2.5 Baths
- 2,792 Sq Ft
160 Lineage Ct, Monticello, FL 32344

Beautiful 3-bedroom, 2.5-bath farmhouse offers privacy, charm, and modern conveniences. Built in 2016 and tucked away at the end of a cul-de-sac on 2.78 acres in desirable Heritage Hills. Home features an iron gate and long driveway—plenty of extra room for your boat or RV—along with a metal roof, a classic rocking chair front porch, large covered patio for entertaining and a 2-car garage.

Leanne Groom The Naumann Group Real Estate

160 Lineage Ct, 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

/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

/63
$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
/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

/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
/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

/18
Est $254,566 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
$649,900
- 3 Beds
- 2.5 Baths
- 3,214 Sq Ft
150 N Ojibwa Rd, Monticello, FL 32344

Tranquil 5.1 acre retreat nestled deep in a pecan grove just outside Monticello, Florida has it all. This recently remodeled 3BR/2BA home offers space, privacy and flexibility in a rural setting only 40 minutes from the heart of Tallahassee. Take advantage of everything Tallahassee offers while paying lower Jefferson County taxes. The pecan trees qualify for an agricultural land use status,

Hettie Spooner Hill Spooner & Elliott Inc

150 N Ojibwa Rd, Monticello, FL 32344
/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

/31
Est $129,669 Not Listed For Sale
- 3 Beds
821 Old Lloyd Rd Unit 2, Monticello, FL 32344

821 Old Lloyd Rd Unit 2, Monticello, FL 32344

/19
$430,000 New Construction
- 3 Beds
- 2 Baths
- 1,865 Sq Ft
173 Deerfield Ln, Monticello, FL 32344

NEW CONSTRUCTION COMPLETE! Walk into this stunningly crafted three-bedroom, two-bathroom home that is perfectly rooted on a corner lot just a few miles from town. Situated on a full acre of land, this charming property is a rare find, free from HOA restrictions—giving you the freedom to personalize your space as you wish. Inside, you'll discover an open and welcoming floor plan that includes

Caleb Stephens Silo Hill Properties

173 Deerfield Ln, 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

/5
Est $123,154 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,314 Sq Ft
220 Horseshoe Rd, Monticello, FL 32344

220 Horseshoe Rd, Monticello, FL 32344

/50
$499,000 New Construction
- 3 Beds
- 2 Baths
- 1,774 Sq Ft
107 Tarn Way, Monticello, FL 32344

2024 Custom Built Home with Premium Upgrades in Hemings Pond Subdivision! Better than new - This 3 bedroom/2 Bathroom 2024-build by Nailed It Construction offers luxury vinyl plank floors throughout, upgraded light fixtures, premium countertops, and elegant bath finishes. Both bathrooms feature tastefully muted designer tile-work. Thoughtful owner upgrades include: custom wood plantation shutters

Brenna Kelly-Ward Kelly & Kelly Properties, Inc

107 Tarn Way, Monticello, FL 32344
/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

/30
Est $530,764 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,016 Sq Ft
3214 Tram Rd, Monticello, FL 32344

3214 Tram Rd, Monticello, FL 32344

/3
$499,900 New Construction
- 4 Beds
- 3 Baths
- 1,798 Sq Ft
855 S Waukeenah St, Monticello, FL 32344

Stunning New Construction home currently being 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 will feature vinyl plank flooring, granite countertops, walk in tile shower and tub in master, upgraded trim package, and stainless appliances. Some finishes have been selected by builder,

Jared Parramore Coastwise Realty

855 S Waukeenah St, Monticello, FL 32344
/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

/28
Est $389,084 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

/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
/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

/38
Est $150,176 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

/38
$440,000 Under Contract
- 3 Beds
- 2 Baths
- 1,398 Sq Ft
478 Robert Thompson, Monticello, FL 32344

Pristine Home on Pristine Acreage! Freedom and space to live your lifestyle, your way, 18.9 acre homestead between Monticello, FL and Tallahassee, FL with easy access to Interstate 10. Mostly wooded and super private! This immaculately maintained, one-owner, 2002 home features 3-bedrooms, 2-bathrooms, with 1,398sqft. No restrictions, No HOA, ready for chickens, all livestock and horses are

Ben Marinelli All Realty Services

478 Robert Thompson, 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

/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

/47
$449,000 Under Contract
- 3 Beds
- 2 Baths
- 2,334 Sq Ft
1293 Vista Rd, Monticello, FL 32344

Country living at its finest and NO HOA! 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
/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

/28
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,323 Sq Ft
1993 Hartsfield Rd, Monticello, FL 32344

1993 Hartsfield Rd, Monticello, FL 32344

/37
$465,000 Under Contract
- 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

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