Homes for Sale near Jefferson Virtual Middle and High

• 

  

  

  /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
• 

  

  

  /38

  $427,900

  • 4 Beds
  • 2 Baths
  • 1,809 Sq Ft

  115 Crooked Creek Ln, Monticello, FL 32344

  New Construction in Crooked Creek on a spacious .72 acre lot! This open plan features 4 bedrooms, 2 bathrooms and a 2 car garage (floor plan and survey are attached in associated docs). The kitchen has a light and bright design with white cabinets, quartz counters, subway tile backsplash, and GE stainless appliances. LVP flooring throughout (tile in baths), electric fireplace, covered back patio,

  Amber Renaud The Nova Group Realty

  115 Crooked Creek Ln, Monticello, FL 32344
• 

  

  

  /35

  $399,000

  • 4 Beds
  • 3.5 Baths
  • 2,768 Sq Ft

  925 E Pearl St, Monticello, FL 32344

  Charming historic home with bonus guest cottage, located on the most beautiful oak lined street in picturesque Monticello, Florida. OWNER FINANCING AVAILABLE call for convenient terms. Enjoy small-town living in this updated home featuring a 2020 Roof, 2022 HVAC, 2025 Water Heater, Updated Electrical, CPVC and Copper Plumbing, Schedule 40 sewer piping, and mostly updated windows. Relax on the

  Tom Grasberger Gaff's Realty Company

  925 E Pearl St, Monticello, FL 32344
• 

  

  

  /37

  $419,900

  • 3 Beds
  • 2 Baths
  • 2,766 Sq Ft

  205 N Rhodes St, Monticello, FL 32344

  Classic historical home built in the 1920's. Walking distance to charming downtown Monticello. Large covered front porch for kicking back and relaxing. Wood floors throughout, high ceiling and large open kitchen. This beauty boast over 2700 sf of heated and cooled living space. Beautiful entry into foyer with stairway leading to upstairs landing and two bedrooms. Formal living, formal dining and

  Pam Kelly Kelly & Kelly Properties, Inc

  205 N Rhodes St, Monticello, FL 32344
• 

  

  

  /41

  $425,000

  • 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

  $599,900

  • 4 Beds
  • 5 Baths
  • 3,862 Sq Ft

  3873 N Jefferson St, Monticello, FL 32344

  Stunning 4 Bedroom, 3.5 Bath Home on 9.73 Acres with Large Detached Garage plus Oversized Attached 2 Car Garage Located just north of this spacious 3,862 square foot home sits on 9.73 acres with a tranquil creek running through the rear of the property. The home is built on high and dry ground, and not located in a flood zone or HOA. Built in 2007, the home features 10-foot ceilings,

  Stephanie Dobson Southern Land & Homes

  3873 N Jefferson St, Monticello, FL 32344
• 

  

  /34

  $465,000

  • 4 Beds
  • 3 Baths
  • 2,076 Sq Ft

  376 Tecumseh Rd, Monticello, FL 32344

  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 include freshly

  Casey Skelton Pearson Realty Inc.

  376 Tecumseh Rd, Monticello, FL 32344
• 

  

  /40

  $549,900

  • 3 Beds
  • 3 Baths
  • 2,661 Sq Ft

  141 Shumard Ct, Monticello, FL 32344

  This stunning 3-bedroom, 3-bath home is perfectly situated on a quiet cul-de-sac, offering the ideal blend of modern comfort and thoughtful upgrades, all on a fully fenced 0.90-acre lot. The spacious open floor plan is designed for both entertaining and everyday living, complemented by a gourmet kitchen with stainless steel appliances. The garage includes an added sink for extra convenience, and

  Kara Richetti Real Broker LLC

  141 Shumard Ct, Monticello, FL 32344
• 

  

  /32

  $595,000

  • 3 Beds
  • 3 Baths
  • 3,026 Sq Ft

  3827 N Jefferson St, Monticello, FL 32344

  Stylish Brick Home on 5 acres with pond. Extra roomy with 3000 + sf of living area. Home has formal living and dining along with a lovey family room with fireplace off of kitchen. Additionally, there is an office and large sun-porch. Master Bedroom is extra large with oversized master bath. Easy commute to Thomasville, Georgia.

  Pam Kelly Kelly & Kelly Properties, Inc

  3827 N Jefferson St, Monticello, FL 32344
• 

  

  /42

  $495,900 New Construction

  • 3 Beds
  • 2 Baths
  • 2,061 Sq Ft

  350 Oconee, Monticello, FL 32344

  Welcome to Covey Run, a private estate community in the heart of Monticello. Your new 3 bedroom 2 bath 2 car garage sits on 2.24 acres. Home features open floor plan with primary on-suite and large walk-in closet. Kitchen is ready for the chef in mind with gas range and plenty of room for prep. Living room features 10 foot ceilings, fireplace and opens to a sunroom. House has Generac Home

  Steve Walker Steve C. Walker Realty, LLC

  350 Oconee, Monticello, FL 32344
• 

  

  /41

  $334,995

  • 3 Beds
  • 2 Baths
  • 1,555 Sq Ft

  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
• 

  

  /42

  $1,599,000

  • 5 Beds
  • 4.5 Baths
  • 5,476 Sq Ft

  221 Kiley Dr, Monticello, FL 32344

  Welcome to a rare and exquisite, turn-key, 15-acre modern luxury estate, where timeless elegance meets Southern charm. Custom built by Riley Palmer, this exclusive, gated property is nestled just minutes from Tallahassee, Florida's Capital City, and Thomasville, GA in Monticello-home to a storied opera house and chic dining options-and offers the perfect blend of privacy, prestige and proximity.

  Barbra Engel & Volkers Tallahassee

  221 Kiley Dr, Monticello, FL 32344
• 

  

  /42

  $1,200,000

  • 5 Beds
  • 5.5 Baths
  • 4,700 Sq Ft

  1165 Dills Rd, Monticello, FL 32344

  Nature Lover’s Dream – Custom Estate on 21+ Acres. Escape to peace and privacy in this stunning custom-built home surrounded by over 21 acres of natural beauty. Thoughtfully designed with both comfort and function in mind, this spacious estate features a gourmet kitchen with gas stove and butler’s pantry, formal and casual living spaces, a cozy library, and a luxurious primary suite with porch

  Callie Rhoads The Naumann Group Real Estate

  1165 Dills Rd, Monticello, FL 32344
• 

  

  /42

  $265,000

  • 3 Beds
  • 2 Baths
  • 2,390 Sq Ft

  2436 N Jefferson Hwy, Monticello, FL 32344

  Discover the perfect blend of rustic charm and opportunity with this unique country property. Nestled on 3+ acres, this older farm house offers character and room to grow. The main home features spacious living areas with wood floors throughout and plenty of potential for updates to make it your own. Front screen porch and large utility room. Also included is a second block home. Additional

  Pam Kelly Kelly & Kelly Properties, Inc

  2436 N Jefferson Hwy, Monticello, FL 32344
• 

  

  /3

  $150,000

  • Land
  • 11 Acres
  • $14,045 per Acre

  Vacant N Jefferson St, Monticello, FL 32344

  Tucked away just off North Jefferson Highway, this beautiful 10.68-acre parcel offers a quiet setting with plenty of potential. Located just 2.5 miles from the Georgia border, it's an easy 20-minute drive to downtown Thomasville and only 8 minutes to Monticello. The land is fully wooded with a mix of mature oaks and pines. Approximately 75% is high and dry—perfect for building, clearing a

  Catherine Hope All Realty Services

  Vacant N Jefferson St, Monticello, FL 32344
• 

  

  /19

  $305,000

  • 4 Beds
  • 2 Baths
  • 1,858 Sq Ft

  575 E Palmer Mill Rd, Monticello, FL 32344

  Spacious home located within walking distance of Historic Downtown Monticello. This four bedroom home sits quietly on a manageable half acre lot. Sporting both original hardwood flooring and newly installed LVP flooring, this home blends perfectly for any new home owners. Updated bathrooms and appliances have all been done within the last 5 years. Sizes are approximate.

  Caleb Stephens Waypoint Properties East

  575 E Palmer Mill Rd, Monticello, FL 32344
• 

  

  /4

  $89,000

  • Land
  • 4.42 Acres
  • $20,136 per Acre

  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

  $437,500

  • Land
  • 22 Acres
  • $19,770 per Acre

  00 Boston Hwy, Monticello, FL 32344

  2 MILES FROM Monticello Courthouse! Bordering Jefferson County Country Club. 2 Parcels for total of 22.13 Acres adjacent to Jefferson County Golf Club and bordering Boston Hwy- 1028 ft. frontage - and Mamie Scott Drive. 2 Acres on Mamie Scott with 360' FRONTAGE AND has City Water/Electric Access and is actually within City Limits with zoning of RESIDENTIAL-MULTIFAMILY. Remaining property zoning

  Jennifer Ward Century 21 First Story

  00 Boston Hwy, Monticello, FL 32344
• 

  

  /41

  $365,000

  • 2 Beds
  • 1.5 Baths
  • 1,140 Sq Ft

  265 Still Rd, Monticello, FL 32344

  This inviting 2-bedroom, 1.5-bath home sits on 5 peaceful acres between Monticello, FL, and Thomasville, GA, offering a great mix of indoor comfort and outdoor space. It’s just as cute as you want it, with endless potential for outdoor living! Inside, the open great-room layout feels both spacious and cozy, with a large utility room leading to the screened porch and a covered carport that’s

  Catherine Hope All Realty Services

  265 Still Rd, Monticello, FL 32344
• 

  

  /42

  $269,000

  • 3 Beds
  • 3 Baths
  • 2,280 Sq Ft

  2422 N Jefferson St, Monticello, FL 32344

  This beautiful double-wide has been immaculately maintained, with recent updates, including new floors in the kitchen/laundry/guest bath (2014), a new refrigerator (2022), and a new hot water heater (2021). The roof was also replaced in (2014). The living area boasts a space large enough to accommodate separate living and family rooms. The kitchen has a 2nd prep sink in the island with a

  Brenna Kelly-Ward Kelly & Kelly Properties, Inc

  2422 N Jefferson St, Monticello, FL 32344
• 

  

  /42

  $2,499,000

  • 6 Beds
  • 7 Baths
  • 6,350 Sq Ft

  305 Old Lloyd Rd, Monticello, FL 32344

  Private Estate on Nearly 30 Acres in Beautiful Monticello. Welcome to your own private retreat! This custom-built estate sits on 29.93 serene acres and offers the perfect blend of luxury, comfort, and room to roam. The main home features 5 spacious bedrooms, 4.5 baths, plus an office/family room, separate dining room, living room, playroom, and a dedicated laundry room—ideal for both everyday

  Callie Rhoads The Naumann Group Real Estate

  305 Old Lloyd Rd, Monticello, FL 32344
• 

  

  /26

  $249,000

  • 2 Beds
  • 2 Baths
  • 1,338 Sq Ft

  495 N Cherry Ct, Monticello, FL 32344

  Over 55 Townhome community of only 8 homes in downtown Monticello. Walk to restaurants and shops. Mint condition 2 bedroom 2 bath with nice screened porch and walk in tub system. This end unit is extra private. New Roof (March 2025).

  Pam Kelly Kelly & Kelly Properties, Inc

  495 N Cherry Ct, Monticello, FL 32344
• 

  

  /41

  $349,900

  • 3 Beds
  • 2.5 Baths
  • 3,348 Sq Ft

  665 W Washington St, Monticello, FL 32344

  Owner Financing available!! A brand new roof is being installed this week, adding immediate value and peace of mind, while maintaining the integrity and character of this historic home! Step back in time in the T.T. Turnbull House designed by Neel Reid. This stunning 1915 home is a true architectural treasure in the heart of downtown Monticello, FL. Sitting on .68 acres, this historic gem is

  Catherine Hope All Realty Services

  665 W Washington St, Monticello, FL 32344
• 

  

  /42

  $1,125,000

  • 4 Beds
  • 4.5 Baths
  • 3,696 Sq Ft

  825 Rainey Run, Monticello, FL 32344

  Stunning estate on 10 acres in private gated community, situated just outside of Tallahassee and Monticello, Florida. This all-brick home boasts 3,696 square feet of indoor living space which includes a primary suite downstairs with 2 large closets, soaking tub and a walk in shower. The chef’s kitchen is fully equipped for hosting with touches like a GE Monogram stove and additional built-in

  Catherine Hope All Realty Services

  825 Rainey Run, Monticello, FL 32344
• 

  

  /20

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft

  170 W Cherokee Ave, 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 rented till then end of May. A

  Ken Foster FosterGrant Real Estate, LLC

  170 W Cherokee Ave, Monticello, FL 32344
• 

  

  /42

  $390,000

  • 3 Beds
  • 2 Baths
  • 1,917 Sq Ft

  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
• 

  

  /32

  $295,000

  • 3 Beds
  • 2.5 Baths
  • 2,467 Sq Ft

  490 E Palmer Mill Rd, Monticello, FL 32344

  The Haile House originally built in 1893 is located in downtown Monticello FL. This wonderful victorian home features original hardwood pine floors, stain glass windows in the front parlor, original wavy glass windows throughout the home, 12 ft ceilings, a bay window and so much more! The 2,467 sqft beauty has 3 bedrooms and 2 and a half baths, fenced in yard, with a detached workshop. Less than

  Alicia Radtke All Realty Services

  490 E Palmer Mill Rd, Monticello, FL 32344
• 

  

  /3

  $55,000

  • Land
  • 0.53 Acre
  • $103,774 per Acre

  0 Tarn Way Unit 380408, Monticello, FL 32344

  Welcome to Hemings Pond in the charming town of Monticello. Nestled amidst the tranquil beauty of lush greenery and shimmering ponds. Savor the convenience of local dining and shopping that are only a short drive away, whether you choose to explore downtown Monticello, FL or Thomasville, GA. Our stunning community promises to envelop you in warmth and a sense of belonging. Let us start building

  Amber McKinney Hamilton Realty Advisors LLC

  0 Tarn Way Unit 380408, Monticello, FL 32344
• 

  

  /3

  $65,000

  • Land
  • 1.15 Acres
  • $56,522 per Acre

  0 Tarn Way Unit 380407, Monticello, FL 32344

  Welcome to Hemings Pond in the charming town of Monticello. Nestled amidst the tranquil beauty of lush greenery and shimmering ponds. Savor the convenience of local dining and shopping that are only a short drive away, whether you choose to explore downtown Monticello, FL or Thomasville, GA. Our stunning community promises to envelop you in warmth and a sense of belonging. Let us start building

  Amber McKinney Hamilton Realty Advisors LLC

  0 Tarn Way Unit 380407, Monticello, FL 32344
• 

  

  /18

  $249,900

  • 4 Beds
  • 3 Baths
  • 2,553 Sq Ft

  34 W Hummingbird Ln, Monticello, FL 32344

  So many options with this property!! It boasts 2 separate living spaces joined by a common family room. One side of the home has 1 bed and 1 bath, it's own kitchen and living space. The other side of the home has 3 bedrooms, 2 bathrooms and the kitchen and living area. The family room with laundry is in the middle of the home. Each side has an enclosed porch too! So much space and an

  Susan Gillespie Lord & Stanley Realty, Inc.

  34 W Hummingbird Ln, Monticello, FL 32344
• 

  

  /6

  $816,000

  • Land
  • 68 Acres
  • $12,000 per Acre

  290 Oetinger Rd, Monticello, FL 32344

  68 acres in Northern Jefferson County Fl. Beautiful Pasture surrounded by Old Growth Pine Timber. Pond sits in the middle of the property and this property has a Plantation on Two sides. Well, Septic Tank and Barn are included with property. Deer and Turkey are abundant with an excellent spot for a Dove Field. Minutes from Monticello Fl. and Thomasville Ga. this is an ideal spot for someone

  Charles Ward Hayden Outdoors Real Estate

  290 Oetinger Rd, Monticello, FL 32344
• 

  

  /5

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,210 Sq Ft

  1490 Hampton Place, Monticello, FL 32344

  Great single family home situated on large lot in desirable Coopers Pond Community near I-10 East. Own this 3 bedrooms 2 bathrooms home as a first time home buyer or retirement home. It is currently occupied with a tenant and can be purchased with an opportunity of immediate income. New roof 2024, ceramic tile floors throughout, partially fenced back yard, large patio with one car garage. A

  Jackie Austin Shamrock Professionals Realty

  1490 Hampton Place, Monticello, FL 32344
• 

  

  /7

  $410,000

  • 2,311 Sq Ft

  1496 Hampton Place Unit 2, Monticello, FL 32344

  INVESTMENT OPPORTUNITY in desirable Coopers Pond Community near I-10 East. Own this fully occupied Duplex 3 bedrooms 2 full bathrooms (2 units). Immediate income producing property in a growing renters market with lots of growth potentials. Well maintained property with new roof 2024, ceramic tile floors throughout, partially fenced back yard and patio, located on a large lot and plenty of

  Jackie Austin Shamrock Professionals Realty

  1496 Hampton Place Unit 2, Monticello, FL 32344
• 

  

  /3

  $471,000

  • Land
  • 58 Acres
  • $8,057 per Acre

  1310 Piney Woods Rd, Monticello, FL 32344

  This property contains three tax ID number. The other 2 numbers are: 03-1N-4E-0000-001F-0000 and 03-1N-4E-0000-001E-0000. A total of 58.46 acres; currently there is no for sale sign on the property. Very nice wooded tract with great location; easy access to Tallahassee. It has timber potential and would be a good home tract also. Community water is available for the property along with high

  Steve Walker Steve C. Walker Realty, LLC

  1310 Piney Woods Rd, Monticello, FL 32344
• 

  

  /8

  $42,500

  • Land
  • 5.00 Acres
  • $8,500 per Acre

  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
• 

  

  /19

  $395,000

  • Land
  • 3.20 Acres
  • $123,438 per Acre

  XX Shiver Rd, Monticello, FL 32345

  Beautiful High lot at corner of Hwy 19, Shiver and Lake Rd. This listing is compilation of 3 contiguous parcels : (19-2N-5E-0140-0000-0300 and 19-2N-5E-0000-0210-0000 and 19-2N-5E-0140-0000-0170). for a total of 3.25 acres . PRIME location for multi-family, office, mixed use commercial business that needs visibility and ease of access. Utilities available- Water access to main line is Under Hwy

  Jennifer Ward Century 21 First Story

  XX Shiver Rd, Monticello, FL 32345
• 

  

  /4

  $69,000

  • Land
  • 0.29 Acre
  • $237,931 per Acre

  205 E Cherokee Ave, Monticello, FL 32344

  Prime vacant cleared commercial lot in downtown Monticello. Zoned Commercial B-2 Business Highway. Located Steps from US 19 South Across street from Burger King and Dollar Tree. Next door to Oreilly's Auto parts. High Traffic area and Good visibility. Address is for GPS only. Acreage is subject to survey.

  Starbuck Rissman Steve C. Walker Realty, LLC

  205 E Cherokee Ave, Monticello, FL 32344
• 

  /2

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,370 Sq Ft

  1535 Willow Rd, Monticello, FL 32344

  Like New! Barely lived in Home in the sought-after Crooked Creek Subdivision! Easy commute to Thomasville and Tallahassee with the small-town charm of Monticello! This beautiful 3/2 is on a spacious corner lot and the house is upgraded to include but not limited to stainless steel appliances, recessed lighting, vaulted ceilings, with granite and quartz countertops, and a stunning kitchen island.

  Chance Shutes Keller Williams Town & Country

  1535 Willow Rd, Monticello, FL 32344
• 

  

  /3

  $469,995 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,940 Sq Ft

  52 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

  52 Mire Ct, 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

Showing Results 1 - 40, Page 1 of 2