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Homes for Sale near Jefferson County Turning Point School

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  • /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

    Agent Photo

    Shanna D'Attile

    Keller Williams Town & Country

    (850) 809-9683

    0000 Waukeenah Hwy, 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
  • /42

    $489,900 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
  • /47

    $459,000

    • 3 Beds
    • 2 Baths
    • 2,334 Sq Ft

    1293 Vista Rd, Monticello, FL 32344

    Country living at its finest! 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
  • /38

    $575,000

    • 3 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    151 N Ojibwa Rd, Monticello, FL 32344

    Spacious, Private, and Ready to Go! This 3-bed, 3-bath home sits on just over 5 acres of agricultural-zoned land, offering space, privacy, and freedom to live how you want. With 2,400 sq ft, there's plenty of room — including a bonus room over the 2-car garage with A/C, a dedicated home office space with an attached bathroom, and an oversized workshop ready for your tools, equipment, or weekend

    Clint Bailey Superior Realty Group LLC

    151 N Ojibwa Rd, 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
  • /37

    $465,000

    • 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
  • /40

    $600,000

    • 4 Beds
    • 3.5 Baths
    • 2,771 Sq Ft

    44 S Ojibwa Rd, Monticello, FL 32344

    Escape the hustle and enjoy peaceful country living with the convenience of modern amenities! This spacious 4 bedroom, 3.5 bathroom home offers 2,771 square feet of well-designed space sitting on 5 beautiful acres with producing pecan trees. Whether you're ready to start your homesteading journey or simply want more space and privacy, this property is ready for you. With plenty of room to grow,

    Brett Miller Hollifield Real Estate Group

    44 S Ojibwa Rd, 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
  • /40

    $525,000

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

    141 Shumard Ct, Monticello, FL 32344

    Back on the Market- Buyer's Financing Fell Thru. 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

    Kara Richetti Real Broker LLC

    141 Shumard Ct, 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
  • /14

    $189,000

    • 3 Beds
    • 2 Baths
    • 1,716 Sq Ft

    375 Maple St, Monticello, FL 32344

    Affordable home nestled in the heart of Monticello! This spacious home sports a freshly painted open floor plan. Wood finished line this home sharing a feeling of craftsmanship. Updated appliances make this home walk in ready for its next family. Nestled on a corner lot, this home has great curb appeal.

    Caleb Stephens Silo Hill Properties

    375 Maple St, Monticello, FL 32344
  • /55

    $1,100,000

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

    1165 Dills Rd, Monticello, FL 32344

    Nature Lover’s Dream — a rare opportunity to own a stunning custom estate offering peace, privacy, and over 21 acres of unspoiled natural beauty. Thoughtfully designed for both comfort and function, this spacious home boasts more than 4,500 square feet of living space. Inside, enjoy a gourmet kitchen with gas range and butler’s pantry, formal and casual living areas, a cozy library, and a

    Callie Rhoads The Naumann Group Real Estate

    1165 Dills Rd, Monticello, FL 32344
  • /27

    $325,000

    • 3 Beds
    • 1.5 Baths
    • 1,772 Sq Ft

    395 W Palmer Mill Rd, Monticello, FL 32344

    Check out this craftsman style home in the heart of Monticello. This 1920s charmer has 3 bedrooms, 1 & 1/2 baths, wrap around porches, fenced in yards (front and back) with sidewalks to the center of town just a few blocks away. This home was previously a daycare and could be again if you choose.

    Mark Vollertsen Advanced Real Estate Sales

    395 W Palmer Mill Rd, Monticello, FL 32344
  • /47

    $329,900

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

    1530 Sweetbay Ct, Monticello, FL 32344

    Beautiful 2021 built 3/2 home on quiet cul-de-sac across from a gorgeous green space with mature trees! Stunning light and bright features with an updated kitchen and baths, including laminate light oak wood flooring, granite counters, stainless appliances, covered back porch and two car garage. This home is a must-see!

    Amber Renaud The Nova Group Realty

    1530 Sweetbay Ct, Monticello, FL 32344
  • /4

    $264,900

    • 5 Beds
    • 3 Baths
    • 4,026 Sq Ft

    620 Hill St, Monticello, FL 32344

    Welcome to this charming home located at 620 Hill St in Monticello, FL. This delightful property features a spacious layout with multiple bedrooms and bathrooms, providing ample space for comfort and functionality. Enjoy the serene surroundings and beautiful exterior, complemented by a well-maintained yard. Inside, you'll find a bright and inviting living area, a modern kitchen, and elegant

    Steven Koleno Beycome of Florida LLC

    620 Hill St, Monticello, FL 32344
  • /42

    $375,000

    • 4 Beds
    • 3 Baths
    • 2,223 Sq Ft

    155 E Seminole Ave, Monticello, FL 32344

    Full of character, this spacious 1950s home offers 4 bedrooms and 3 full bathrooms on a generous 0.60-acre lot in the heart of Monticello. With over 2,200 square feet—including two bedrooms with en suite baths—it also features flexible zoning for residential, business, or mixed use. The layout includes a cozy living room with a fireplace and an airy sunroom, perfect for an office or casual

    Catherine Hope All Realty Services

    155 E Seminole Ave, Monticello, FL 32344
  • /27

    $399,000

    • 3 Beds
    • 2 Baths
    • 2,131 Sq Ft

    133 Devane Rd, Monticello, FL 32344

    Peaceful 10-Acre Country Retreat with Pool - Just Outside Chattahoochee, FL Discover the charm of country living with this spacious 3-bedroom, 2-bath single-family home located just minutes from the quaint town of Chattahoochee, Florida. Enter through the winding tree lined road that sets the stage for the home that welcomes you at the end. Set on a beautifully wooded 10-acre parcel, this 2,131

    Bubba McCants EXP Realty LLC

    133 Devane Rd, Monticello, FL 32344
  • /42

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,841 Sq Ft

    952 Turney Anderson Rd, Monticello, FL 32344

    Discover your own private retreat with this charming home set on a fully fenced 10-acre lot. Nestled among mature pecan and fruit trees, this property offers the perfect blend of tranquility, space, and functionality. Enjoy relaxing mornings and evenings on the spacious front and back porches, ideal for soaking in the serene surroundings. The home features a practical layout with a cozy living

    Katherine Hansli Searcy The Naumann Group Real Estate

    952 Turney Anderson Rd, Monticello, FL 32344
  • /36

    $399,000

    • 3 Beds
    • 2 Baths
    • 2,020 Sq Ft

    259 Barnes Rd, Monticello, FL 32344

    Spacious Brick on 4.25 acres. Easy Thomasville commute. Discover peace and privacy with this well maintained brick ranch nestled in the woods. Step into the spacious living room with cozy wood burning fireplace, ideal for relaxing evenings or entertaining. Office, large utility room, 2 car garage, and workshop are some of the extras. Enjoy this quiet private setting.

    Pam Kelly Kelly & Kelly Properties, Inc

    259 Barnes Rd, Monticello, FL 32344
  • /43

    $1,549,000

    • 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 with soaring ceilings and interior doors, is nestled just minutes from Tallahassee, Florida's Capital City, and historic Thomasville, Georgia in Monticello-home to a storied opera house and chic dining options-and

    Barbra Engel & Völkers Tallahassee

    221 Kiley Dr, Monticello, FL 32344
  • /42

    $685,000

    • 3 Beds
    • 2.5 Baths
    • 3,214 Sq Ft

    150 N Ojibwa Rd, Monticello, FL 32344

    Peaceful 5.10+ acre retreat in Objiwa Acres! This beautifully maintained 3BR/2BA home offers space, privacy, and flexibility—surrounded by a manicured lawn, rows of pecan trees, a dedicated herb garden, and a saltwater plunge pool with fountain. Enjoy multiple outdoor living spaces including a screened front porch, screened back porch, and a bright true Florida room with vaulted ceilings. A

    Hettie Spooner Hill Spooner & Elliott Inc

    150 N Ojibwa 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
  • /19

    $299,000

    • 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 Silo Hill Properties

    575 E Palmer Mill Rd, 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
  • /37

    $398,000

    • 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
  • /40

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,985 Sq Ft

    480 W Washington St, Monticello, FL 32344

    OWNERS MOTIVATED-ALL REASONABLE OFFERS WILL BE CONSIDERED.Step Back In Time! Rare chance to own your own piece of "Old Florida". Craftsman Style beauty with soaring 10 ' bead-board ceilings and 10 " baseboards, original pine floors and 4 gas fireplaces. Perfect blend of old Florida charm and modern conveniences. Statuary Marble countertops and copper sink in kitchen, extra large dining room for

    Pam Kelly Kelly & Kelly Properties, Inc

    480 W Washington St, 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
  • /32

    $595,000

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

    3827 N Jefferson St, Monticello, FL 32344

    Spacious Contemporary Home on 5 Acres with Pond, Minutes from Thomasville, Ga! Enjoy peaceful country living with modern comforts in this stunning 3 bedroom, 3 bathroom brick home on 5 beautiful acres with a private pond. With over 3,000 square feet of living space, this property offers room to spread out and features thoughtful touches throughout. Inside, you'll find a large den with cozy

    Pam Kelly Kelly & Kelly Properties, Inc

    3827 N Jefferson St, 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
  • /8

    $38,500

    • Land
    • 5.00 Acres
    • $7,700 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
  • /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
  • /8

    $289,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,290 Sq Ft

    1125 E Dogwood St, Monticello, FL 32344

    Must see this brand new home being built by Southern Construction in the downtown Monticello area. Home features 3 bed, 2 baths, granite countertops, upgraded trim package, vinyl plank flooring throughout, tile bathroom and laundry floors, and stainless appliance package. Pics are of previous build, buyer may have time to pick finishes pending time of contract. Home expected to be completed in

    Jared Parramore Coastwise Realty

    1125 E Dogwood St, Monticello, FL 32344
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