Monticello, FL Homes

/34
Not Listed For Sale

336 Lake Rd, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
- Built 1999
336 Lake Rd, Monticello, FL 32344

Last Sold Summary
- $137/SF
- 99 Days On Market
Last Sold Price $200,000

Last Listing Agent Tina Coombs Big Fish Real Estate Services

/38
$449,900 Under Contract
- 3 Beds
- 2 Baths
- 1,774 Sq Ft
107 S Tarn Way, Monticello, FL 32344

Welcome to this beautifully custom-built 3 bedroom, 2 bath home completed in 2024 and located in the desirable Hemings Pond Subdivision. Offering the perfect blend of modern construction and thoughtful upgrades, this move-in ready showcases luxury vinyl plank flooring, upgraded light fixtures, premium countertops, and elegant bath fixtures. Owner selected custom enhancements elevate the space

Joana Villeneuve Hill Spooner & Elliott Inc

107 S Tarn Way, Monticello, FL 32344
/29
$60,000 Sold Apr 29, 2025

1150 Sage St, Monticello, FL 32344
- 5 Beds
- 2 Baths
- 2,612 Sq Ft
- Built 1914
Last Sold Summary
- 31% Below List Price
- $23/SF
- 52 Days On Market
Current Estimated Value $144,740

Last Listing Agent Gabriela Sacco All Realty Services

1150 Sage St, Monticello, FL 32344

/28
Est $486,255 Not Listed For Sale

129 Indian Hills Rd, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 3,328 Sq Ft
- Built 1996
129 Indian Hills Rd, Monticello, FL 32344

Last Sold Summary
- 47% Above List Price
- $99/SF
- 180 Days On Market
Last Sold Price $330,000

Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

/31
$434,000
- 3 Beds
- 2 Baths
- 2,000 Sq Ft
285 Mallard Ln, Monticello, FL 32344

*Jefferson County peaceful country living with a waterfront backdrop! Built in 2008, this well maintained 3 bedroom, 2 bath home sits on 4.89 beautifully (mostly cleared) acres offering privacy and natural beauty backing directly up to Lloyd Lake- perfect for relaxing evenings with scenic views. Pretty rocking chair front porch as well as a screened in back porch with a propane hookup for

Shelley Duke Red Bird Realty

285 Mallard Ln, Monticello, FL 32344
/33
$186,000 Sold Nov 21, 2025

1065 S Mulberry St, Monticello, FL 32344
- 2 Beds
- 2 Baths
- 1,356 Sq Ft
- Built 1927
Last Sold Summary
- 2% Below List Price
- $137/SF
- 65 Days On Market
Current Estimated Value $192,963

Last Listing Agent Katherine Gonzalez Pearson Realty Inc.

1065 S Mulberry St, Monticello, FL 32344

/38
Est $179,572 Not Listed For Sale

310 N Olive St, Monticello, FL 32344
- 2 Beds
- 1 Bath
- 912 Sq Ft
- Built 1948
310 N Olive St, Monticello, FL 32344

Last Sold Summary
- 3% Below List Price
- $203/SF
- 36 Days On Market
Last Sold Price $185,000

Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

/54
$525,000 Under Contract
- 4 Beds
- 3 Baths
- 2,784 Sq Ft
70 Generation Ct, Monticello, FL 32344

Wow! Special opportunity to add your personal touches! Design your dream kitchen! Craftsman style home features a roomy floorplan with lots of storage nooks and crannies, huge primary suite waiting for your perfect finishes, open kitchen and all nestled on private 4.45 acres. Many of the are there to finish trim, there’s extra stone and extra tile. LVP and ceramic tile flooring throughout home,

Lee Duggar Re/Max Professionals Realty

70 Generation Ct, Monticello, FL 32344
/28
$202,000 Sold Oct 20, 2025

85 Pine Cone Dr, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,678 Sq Ft
- Built 2002
Last Sold Summary
- 4% Below List Price
- $120/SF
- 17 Days On Market
Current Estimated Value $218,746

Last Listing Agent Gabriela Sacco All Realty Services

85 Pine Cone Dr, Monticello, FL 32344

/36
Est $724,761 Not Listed For Sale

250 Hiawatha Farms Rd, Monticello, FL 32344
- 4 Beds
- 3 Baths
- 5,556 Sq Ft
- Built 1998
250 Hiawatha Farms Rd, Monticello, FL 32344

Last Sold Summary
- 23% Above List Price
- $106/SF
- 332 Days On Market
Last Sold Price $590,000

Last Listing Agent Don McLaughlin McLaughlin Real Estate Group

/58
$725,000 Under Contract
- 4 Beds
- 3 Baths
- 2,663 Sq Ft
296 Hunter Ridge, Monticello, FL 32344

Situated on 5 gorgeous acres in Monticello, Florida, this property is the epitome of privacy and modern farmhouse living. Built in 2021, this beautiful 4BR/3BA home also features a 36x30 detached workshop complete with electricity. Step inside to find a spacious office just off the foyer and a light-filled living room featuring a 10-foot lit tray ceiling and a stunning fireplace with built-ins

Hettie Spooner Hill Spooner & Elliott Inc

296 Hunter Ridge, Monticello, FL 32344
/9
$42,000 Sold Feb 26, 2026

50 E Pinhook Rd, Monticello, FL 32344
- Land
- 1.58 Acres
- $26,582 per Acre
Last Sold Summary
- 11% Above List Price
- 3 Days On Market
Last Listing Agent Heather Boyd FL-GA Realty & Auction

50 E Pinhook Rd, Monticello, FL 32344

/42
Est $278,050 Not Listed For Sale

52 Serenity Ln, Monticello, FL 32344
- Built 2019
52 Serenity Ln, Monticello, FL 32344

Last Sold Summary
- 16% Above List Price
- $1,667/SF
- 25 Days On Market
Last Sold Price $240,000

Last Listing Agent Sheena Lloyd Keller Williams Town & Country

/3
$775,000 New Construction
- 4 Beds
- 3 Baths
- 2,377 Sq Ft
693 Tally Hills Dr, Monticello, FL 32344

New Construction. Images are renderings. 4-bedroom, 3-bath home coming soon in Tally Hills Estates. Construction has started on this beautifully designed, new construction home set on over 5 acres.

Shelley Poppell Clover Key Realty

693 Tally Hills Dr, Monticello, FL 32344
/35
$325,000 Sold Nov 25, 2025

1530 Sweetbay Ct, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,370 Sq Ft
- Built 2021
Last Sold Summary
- $237/SF
- 58 Days On Market
Current Estimated Value $334,512

Last Listing Agent Chance Shutes Keller Williams Town & Country

1530 Sweetbay Ct, Monticello, FL 32344

/7
Not Listed For Sale

0 Taylor Rd Unit 375808, Monticello, FL 32344
0 Taylor Rd Unit 375808, Monticello, FL 32344

Last Sold Summary
- 20 Days On Market
Last Sold Price $113,900

Last Listing Agent Kevin Davis The Naumann Group

/61
$545,000
- 3 Beds
- 2 Baths
- 1,680 Sq Ft
2184 Tram Rd, Monticello, FL 32344

BEAUTIFULLY UPDATED ACREAGE HOME ON 22 ACRES WITH POND AND BLUEBERRIE FIELDS! UNIQUE PROPERTY WITH ACRES OF BLUEBERRIES, plus 60x 23, 4 bay garage with heated and cooled office, gym or storage space, 22x23 pole barn and 64x32 large red barn with kitchen and 2 bathrooms, 2 gazebo's, storage shed and more! There is plenty of room to roam on this beautiful property with over $195,000 of updates! The

Penny Herman Penny Herman Realty

2184 Tram Rd, Monticello, FL 32344
/3
$244,900 Sold Mar 21, 2026

655 N Cherry St, Monticello, FL 32344
- 2 Beds
- 2 Baths
- 1,092 Sq Ft
- Built 2026
Last Sold Summary
- $224/SF
- 35 Days On Market
Last Listing Agent Steve Walker Steve C. Walker Realty, LLC

655 N Cherry St, Monticello, FL 32344

/3
Not Listed For Sale

132 Hilltop Dr, Monticello, FL 32344
- 3 Beds
- 2.5 Baths
- 2,623 Sq Ft
- Built 2021
132 Hilltop Dr, Monticello, FL 32344

Last Sold Summary
- $308/SF
Last Sold Price $807,500

Last Listing Agent Kelly Vinson Keller Williams Town & Country

/52
$449,000
- 4 Beds
- 3 Baths
- 3,188 Sq Ft
930 E Pearl St, Monticello, FL 32344

Built between 1890-1910, this Classic Revival home sits on 1.77 acres along one of Monticello’s most admired streets and offers timeless architecture with room to make it your own. The two-story layout includes 4 bedrooms and 3 bathrooms, with a circular driveway framed by boxwoods leading to a wide front porch perfect for rocking chairs. Inside, two front parlors flank the entry—one used as a

Rachel Sparling All Realty Services

930 E Pearl St, Monticello, FL 32344
/2
$160,000 Sold Apr 17, 2025

288 Forest Dr, Monticello, FL 32344
- 2 Beds
- 2 Baths
- 990 Sq Ft
- Built 2020
Last Sold Summary
- 6% Below List Price
- $162/SF
- 165 Days On Market
Last Listing Agent Starbuck Rissman Steve C. Walker Realty, LLC

288 Forest Dr, Monticello, FL 32344

/17
Not Listed For Sale

000 Clark Rd, Monticello, FL 32344
000 Clark Rd, Monticello, FL 32344

Last Sold Summary
- 135 Days On Market
Last Sold Price $175,000

Last Listing Agent Channah Galbraith The American Dream

/44
$420,000 Under Contract
- 5 Beds
- 2 Baths
- 2,324 Sq Ft
40 W Cavallo Trail, Monticello, FL 32344

Beautiful 5BR/2BA home on 3.13 fully fenced acres in Jefferson County, just minutes from Monticello. Built in 2006, this property blends modern comfort with horse-ready potential and includes a horse barn/stable and fencing. Fresh interior paint highlights a spacious layout featuring a cozy fireplace, dedicated laundry room, and a private primary suite with a large soaking tub and separate

Joyce Gardner Signature Realty Professionals

40 W Cavallo Trail, Monticello, FL 32344
/42
$390,000 Sold Jun 26, 2025

1288 Indian Hills Rd, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,917 Sq Ft
- Built 1987
Last Sold Summary
- 8% Below List Price
- $203/SF
- 140 Days On Market
Current Estimated Value $443,379

Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

1288 Indian Hills Rd, Monticello, FL 32344

/31
Not Listed For Sale

112 Rudolph Ln, Monticello, FL 32344
- 4 Beds
- 2 Baths
- 2,112 Sq Ft
- Built 2022
112 Rudolph Ln, Monticello, FL 32344

Last Sold Summary
- $114/SF
- 68 Days On Market
Last Sold Price $240,000

Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

/70
$425,000
- 3 Beds
- 2.5 Baths
- 3,126 Sq Ft
1628 N Jefferson St, Monticello, FL 32344

BACK ON MARKET | IMPROVED PRICE: $425,000 1628 North Jefferson Hwy | 4 BR / 2 1/2 BA | 3,126 SQ FT | 1.5 ACRES Experience the perfect harmony of peaceful living and professional potential. Now offered at an improved price of $425,000, this expansive residence sits atop 1.5 acres of gorgeous landscape, offering a rare blend of space, serenity, and strategic location. The Highlights: ? Spacious

Jennifer Ward Century 21 First Story

1628 N Jefferson St, Monticello, FL 32344
/14
$168,100 Sold Nov 17, 2025

375 Maple St, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 1,716 Sq Ft
- Built 1920
Last Sold Summary
- 11% Below List Price
- $98/SF
- 70 Days On Market
Current Estimated Value $177,432

Last Listing Agent Caleb Stephens Silo Hill Properties

375 Maple St, Monticello, FL 32344

/4
Not Listed For Sale

TBD Blackberry Tr, Monticello, FL 32344
TBD Blackberry Tr, Monticello, FL 32344

Last Sold Summary
- 38 Days On Market
Last Sold Price $49,250

Last Listing Agent Barry Kelly Kelly & Kelly Properties, Inc

/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
/7
$95,000 Sold Aug 01, 2025

0 Taylor Rd Unit 384618, Monticello, FL 32344
- Land
- 5.17 Acres
- $18,375 per Acre
Last Sold Summary
- 21% Below List Price
- 102 Days On Market
Last Listing Agent Kevin Davis The Naumann Group Real Estate

0 Taylor Rd Unit 384618, 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

Last Sold Summary
- 38 Days On Market
Last Sold Price $135,000

Last Listing Agent Hines Boyd FL-GA Realty & Auction

/60
$525,000 Under Contract
- 4 Beds
- 2 Baths
- 1,838 Sq Ft
965 Robert Thompson Rd, Monticello, FL 32344

Quiet country living near everything Tallahassee FL offers. Beautiful 4BR/2BA home on 5 acres. Split bedroom plan. Living room opens to large kitchen and breakfast nook. Sunroom not included in SqFt. Primary bedroom with tray ceilings, private bath with a jetted tub and separate shower. Plantation shutters throughout home. Generator installed 2017. 2 car attached garage and a large detached

Suzanne McGhee Mattox Realty, Inc

965 Robert Thompson Rd, Monticello, FL 32344
/10
$220,000 Sold Aug 26, 2025

1400 Gamble Rd, Monticello, FL 32344
- Land
- 7 Acres
- $31,429 per Acre
Last Sold Summary
- 6% Below List Price
- 119 Days On Market
Current Estimated Value $232,412

Last Listing Agent Kenneth Ayers Primesouth Fezler, Russell and

1400 Gamble Rd, Monticello, FL 32344

/41
Not Listed For Sale

660 Whispering Hill, Monticello, FL 32344
- 3 Beds
- 2.5 Baths
- 2,160 Sq Ft
- Built 2000
660 Whispering Hill, Monticello, FL 32344

Last Sold Summary
- $309/SF
- 31 Days On Market
Last Sold Price $667,000

Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

/19
$480,000 New Construction
- 4 Beds
- 3 Baths
- 1,798 Sq Ft
855 S Waukeenah St, Monticello, FL 32344

Stunning New Construction recently 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 features vinyl plank flooring, granite countertops, walk in tile shower and tub in master, upgraded trim package, and stainless appliances. Nice large back porch with deck, over looking the large

Jared Parramore Coastwise Realty

855 S Waukeenah St, Monticello, FL 32344
/42
$165,000 Sold Feb 27, 2026

2436 N Jefferson Hwy, Monticello, FL 32344
- 3 Beds
- 2 Baths
- 2,390 Sq Ft
- Built 1951
Last Sold Summary
- 38% Below List Price
- $69/SF
- 285 Days On Market
Current Estimated Value $260,957

Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

2436 N Jefferson Hwy, 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

Last Sold Summary
- 31 Days On Market
Last Sold Price $184,440

Last Listing Agent Hines Boyd FL-GA Realty & Auction

/47
$295,000 Under Contract
- 3 Beds
- 1.5 Baths
- 1,834 Sq Ft
575 W Madison St, Monticello, FL 32344

Perfectly located just around the corner from downtown Monticello, this charming 1950s brick home is ready for its next owners! Step inside to find a desirable split floor plan, beautifully maintained new hardwood floors, a cozy wood-burning fireplace, and an updated kitchen featuring newer stainless steel appliances. The spacious half bath offers plumbing already in place to easily convert it

Brooke Feld Keller Williams Town & Country

575 W Madison St, Monticello, FL 32344
/3
$94,500 Sold Sep 05, 2025

0 W Osprey Ln Unit 381026, Monticello, FL 32344
- Land
- 20 Acres
- $4,725 per Acre
Last Sold Summary
- 32% Below List Price
- 222 Days On Market
Last Listing Agent Pam Kelly Kelly & Kelly Properties, Inc

0 W Osprey Ln Unit 381026, 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

Last Sold Summary
- 0 Days On Market
Last Sold Price $202,500

Last Listing Agent Hines Boyd FL-GA Realty & Auction

Showing Results 121 - 160, Page 4 of 18

Florida Jefferson County Monticello

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Monticello, FL Homes

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