Homes in ZIP Code 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
/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

/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

/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
/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

/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

/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
/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

/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

/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
/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

/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

/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
/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

/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

/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
$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

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

420 N Forest Ct, Monticello, FL 32344

/9
$120,000
- Land
- 2.01 Acres
- $59,701 per Acre
40 Westview Ln, Monticello, FL 32344

Load up and take a ride to Lloyd Fl. located between Tallahassee and Monticello Fl. Being offered "AS IS" two 1 acre parcels 18-1N-4E-0108-000G-0030 & 18-1N-4E-0108-000G-0040 for a total of 2.01 acres! Power, septic and well on site, as well as access to city water. There is a 1989 mobile home on site that may be salvageable to the right buyer, or haul it off and prepare for a new build! Bring

Alicia Radtke All Realty Services

40 Westview Ln, 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

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

TBD Blackberry Tr, Monticello, FL 32344

/17
$27,900
- Land
- 1.25 Acres
- $22,320 per Acre
00 Gamble Rd, Monticello, FL 32344

This 1.25-acre tract in Jefferson County, Florida, offers a balanced combination of accessibility, usable land, and proximity to outdoor recreation. Situated in the small unincorporated community of Wacissa FL, the property fronts State Road 59, providing year-round paved access. Its location places it less than 1.2 miles from Wacissa Springs Park and boat launch, a well-known destination for

Thomas Lado WHITETAIL PROPERTIES REAL ESTATE

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

XXXX St Augustine Rd Parcel #2, 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

/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

/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

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

XXX Parcel #3 St Augustine Rd, 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 St Augustine Parcel #4 Rd, Monticello, FL 32344

xxx St Augustine Parcel #4 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

/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

/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

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

00 Valley View 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

Showing Results 81 - 120, Page 3 of 18

Florida Jefferson County Monticello 32344

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage