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Homes for Sale near Jefferson County Turning Point School

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  • /21

    $172,500

    • Land
    • 10 Acres
    • $17,250 per Acre

    TBD Rainey Run, Monticello, FL 32344

    Gated rural community, lakefront 10 acres with large hardwoods. Tranquility awaits, gently sloping land with some clearing.

    Agent Photo

    Barry Kelly

    Kelly & Kelly Properties, Inc

    (448) 233-5231

    TBD Rainey Run, Monticello, FL 32344
  • /57

    $579,000

    • 3 Beds
    • 3 Baths
    • 2,187 Sq Ft

    515 E Palmer Mill Rd, Monticello, FL 32344

    Remarkable, peaceful in-town oasis on 3.54 acres! An incredible find in the heart of downtown Monticello, FL. Not only is this home located on a private 3.54 acre spread, surrounded by a perimeter of natural foliage, but the home itself has been beautifully updated, blending the charm of old and the convenience of new. The 3 bedroom/3 bathroom, 2,000+ sq ft home has a kitchen flooded with natural

    Agent Photo

    Brenna Kelly-Ward

    Kelly & Kelly Properties, Inc

    (448) 334-5445

    515 E Palmer Mill Rd, Monticello, FL 32344
  • /17

    $252,000

    • 3 Beds
    • 1 Bath
    • 1,334 Sq Ft

    1160 E Washington St, Monticello, FL 32344

    Remodeled brick home, 3 br 1 bath, open kitchen living room with fireplace. Large utility room with bonus room. Convenient Monticello location. Carport and privacy fenced back yard.

    Agent Photo

    Barry Kelly

    Kelly & Kelly Properties, Inc

    (448) 231-4719

    1160 E Washington St, Monticello, FL 32344
  • /12

    $165,000

    • Land
    • 10.47 Acres
    • $15,759 per Acre

    5936 Vista Rd, Monticello, FL 32344

    Perfect opportunity to own 10+ acres to build your dream home on this blank slate. Lot is mostly flat and backs up to a power line so no building behind the property. Abundant wildlife present (deer and turkey) and bring all your yard animals. Ride up Vista Road to see your neighbors on larger lots to Waukeenah Hwy to visit the beautiful Monticello Vineyards and Winery. Lot dimensions are

    Agent Photo

    Jaquelynn Harrison-Cofty

    Property Finders Nguyen Realty

    (448) 334-6928

    5936 Vista Rd, Monticello, FL 32344
  • /32

    $269,000

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

    1511 Spring Hollow Dr, Monticello, FL 32344

    Charming home on large .87 acre lot in established subdivision. Sunporch overlooks wooded back yard, a nature lovers paradise. Open floor plan, kitchen/dining/living room combination. 2 car garage with breezeway to the home. An additional 1 acre lot is available for sale with the home for a total of 1.87 acre for $319,000.

    Agent Photo

    Pam Kelly

    Kelly & Kelly Properties, Inc

    (448) 233-5401

    1511 Spring Hollow Dr, Monticello, FL 32344
  • /4

    $60,000

    • Land
    • 0.43 Acre
    • $139,535 per Acre

    tbd Jackson St, Monticello, FL 32344

    2 building lots in the heart of Monticello, quiet side street. Each lot is 50 ft wide by approx. 190 deep. The lots back up to Waukeenah Street.

    Agent Photo

    Pam Kelly

    Kelly & Kelly Properties, Inc

    (448) 334-6781

    tbd Jackson St, Monticello, FL 32344
  • /37

    $300,000

    • 3 Beds
    • 1.5 Baths
    • 1,855 Sq Ft

    950 E Pearl St, Monticello, FL 32344

    Charming 1955 Cottage in the Heart of Monticello,Fl. Welcome home to this cozy yet surprisingly spacious 3-bedroom 1.5 -bath cottage on beautiful Oak Lined Pearl Street. Just a short walk or golf cart ride to historic downtown Monticello. Features include original hardwood floors, new windows, updated electrical and a sunroom with brick paver flooring- perfect for relaxing with morning coffee.

    Agent Photo

    Pam Kelly

    Kelly & Kelly Properties, Inc

    (448) 333-2115

    950 E Pearl St, Monticello, FL 32344
  • /32

    $499,500

    • 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

    Agent Photo

    Pam Kelly

    Kelly & Kelly Properties, Inc

    (850) 367-9518

    3827 N Jefferson St, Monticello, FL 32344
  • /37

    $365,000

    • 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

    Agent Photo

    Pam Kelly

    Kelly & Kelly Properties, Inc

    (448) 236-0470

    205 N Rhodes St, Monticello, FL 32344
  • /38

    $274,900

    • 2 Beds
    • 2 Baths
    • 1,411 Sq Ft

    490 N Cherry Ct, Monticello, FL 32344

    Step into city living just steps from Downtown Monticello, Fl. This one-story condo with private backyard blends modern convenience in this coveted over 55 neighborhood of only 8 units. 2 bedrooms & 2 baths, laundry room with stack unit, W/D included, but the favorite room in the house is the sunroom. Inside, enjoy the bright open-concept living with high ceilings, crown molding, LVP & engineered

    Agent Photo

    Pam Hoveland

    Landcorp, Inc.

    (448) 231-4689

    490 N Cherry Ct, Monticello, FL 32344
  • /14

    $294,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,351 Sq Ft

    1090 Partridge Ln, Monticello, FL 32344

    Currently under construction. Interior pictures are from a previous model home. Approximately 60 days until completion. Home qualifies for USDA financing.

    Steve Walker Steve C. Walker Realty, LLC

    1090 Partridge Ln, Monticello, FL 32344
  • /3

    $244,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,092 Sq Ft

    655 N Cherry St, Monticello, FL 32344

    New construction in the heart of Monticello's Historic District! This beautifully built 1,092 sq ft off-grade home offers modern finishes while fitting seamlessly into the character of the neighborhood. The open floor plan features luxury vinyl plank flooring throughout, a stylish kitchen and stainless steel appliances, and quality craftsmanship from top to bottom. Bathrooms are finished with

    Steve Walker Steve C. Walker Realty, LLC

    655 N Cherry St, Monticello, FL 32344
  • /2

    $244,900

    • 3 Beds
    • 2 Baths
    • 1,235 Sq Ft

    350 Bowman St, Monticello, FL 32344

    New construction; very convenient to downtown; house is close to completion - should be ready in about 45 days.

    Steve Walker Steve C. Walker Realty, LLC

    350 Bowman St, Monticello, FL 32344
  • /5

    $75,000

    • Land
    • 5 Acres
    • $15,000 per Acre

    200 Samanthas Ln, Monticello, FL 32344

    Rare opportunity to own 5± acres on Aucilla Road. This beautiful property features planted pines and offers a blank canvas with endless possibilities for a future homesite, no restrictions! Conveniently located near Monticello and Aucilla Christian Academy, only 8 minutes from I-10 and 30 minutes from Tallahassee. 5 +/- acres — exact acreage to be determined by survey during contract period.

    Allison Smith OaksFeather Realty

    200 Samanthas Ln, Monticello, FL 32344
  • /23

    $325,000

    • 5 Beds
    • 2 Baths
    • 2,659 Sq Ft

    2664 W Washington Hwy, Monticello, FL 32344

    FULLY RENOVATED SPACIOUS HOUSE, 1.3 acres, on picturesque US 90 near Monticello. This move-in-ready home in good condition is a 1950’s era brick ranch-style home with new plumbing, new electric, fresh paint, new roof, and a whole home generator. The main living area is 2,659 sf with a unique two levels. 5 bedrooms and 2 baths with plenty of character, including the "Captain's Room" with built-in

    Heather Boyd FL-GA Realty & Auction

    2664 W Washington Hwy, Monticello, FL 32344
  • /45

    $455,995 New Construction

    • 3 Beds
    • 2 Baths
    • 1,806 Sq Ft

    47 Mire Ct, Monticello, FL 32344

    Amazing new construction Available Now 3 bedroom 2 bathroom by Nailed It Tallahassee LLC Luxurious master suite, Kitchen made of dreams, this is a must see! Preferred Lender offering 1% in closing costs! Photos of current home!

    Amber McKinney Hamilton Realty Advisors LLC

    47 Mire Ct, Monticello, FL 32344
  • /16

    $65,000

    • 2 Beds
    • 1 Bath
    • 888 Sq Ft

    980 Mays St, Monticello, FL 32344

    Probate proceedings underway. Cannot close until court approval. Concrete Block 2/1 Home less than a mile from downtown Monticello! This quaint 888sqft home sits under a metal roof and only requires your vision and a little effort to become a superb starter home or investment opportunity. Property is fully fenced and on city utilities. Room measurements are approximate

    Ben Marinelli All Realty Services

    980 Mays St, Monticello, FL 32344
  • /7

    $135,000

    • Land
    • 10 Acres
    • $13,500 per Acre

    576 Cox Rd, Monticello, FL 32344

    Discover a fantastic future homesite on a secluded 10-acre parcel in northern Jefferson County, Florida! Accessed via a 15-foot-wide easement off a private road, the property opens up to a beautiful, private clearing ideal for building your dream home. The land features a mix of large pines, hardwoods, and magnolias, creating a serene, natural setting. Key utilities are already in place or

    Gabriela Sacco All Realty Services

    576 Cox Rd, Monticello, FL 32344
  • /31

    $277,000

    • 3 Beds
    • 2 Baths
    • 1,740 Sq Ft

    104 Pine Cone Dr, Monticello, FL 32344

    This gorgeous, 3-bedroom, 2-bath modular home, recently renovated by Paul Davis, combines modern comfort and style. Inside, you’ll find an open floor plan, a brand-new kitchen with granite countertops, new appliances, and updated finishes that make everyday living and entertaining a joy. The primary bedroom offers a luxurious ensuite with double vanities, a walk-in shower, and garden tub, as well

    Trevor Ann Clark Keller Williams Town & Country

    104 Pine Cone Dr, Monticello, FL 32344
  • /70

    $1,325,000

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

    221 Kiley Dr, Monticello, FL 32344

    Welcome to 221 Kiley Road in Monticello, Florida — a rare estate where vineyard charm, equestrian living, and exceptional space come together to create an unforgettable lifestyle. This 5-bedroom, 3.5-bathroom estate is a true masterpiece, gracefully set on 5 private acres and complemented by a beautiful pool house with an additional bathroom. An additional adjoining 5-acre parcel is also

    Wilda Sigler Keller Williams Town & Country

    221 Kiley Dr, Monticello, FL 32344
  • /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
  • /3

    $437,500

    • Land
    • 22.13 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
  • /42

    $325,000

    • 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 ensuite 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 dining.

    Catherine Hope All Realty Services

    155 E Seminole Ave, Monticello, FL 32344
  • /70

    $470,000

    • 4 Beds
    • 3 Baths
    • 2,032 Sq Ft

    54 Woodland Dr, Monticello, FL 32344

    One or more photos have been virtually staged (fire in fireplace). Welcome to this beautifully updated modern farmhouse set on 2.14 acres of picturesque and private farmland, offering the perfect blend of peaceful country living and convenient access to town. Surrounded by open skies and scenic views, this property provides privacy, charm, and versatility rarely found. The 4BR/2BA main house

    Lisa Carey Coldwell Banker Hartung

    54 Woodland Dr, Monticello, FL 32344
  • /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
  • /19

    $395,000

    • Land
    • 3.2 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
  • /33

    $999,900

    • 3 Beds
    • 2.5 Baths
    • 4,383 Sq Ft

    728 Turney Anderson Rd, Monticello, FL 32344

    A Timeless Treasure, built by Riley Palmer Construction in 2006, this exceptional home captures the warmth and character of an early-1900s Craftsman farmhouse. It is located on 5 beautiful acres with mature pecan trees in the front and pines in the back yard. A spacious wrap around front porch welcomes you and features reclaimed New Orleans style doors and classic architectural details. Inside,

    Jared Parramore Coastwise Realty

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

    $675,000

    • 5,139 Sq Ft

    625 E Washington St, Monticello, FL 32344

    Amazing Investment Opportunity as a Large family home, multi-generational property or Cash flowing investment! Own your piece of history and enjoy some great cash flow in this beautiful Downton Monticello Home. Built in 1888 and almost 4500 SF in the main house with 9 bedrooms, 7 bathrooms and common areas for the tenants. Currently set up with tenants as a BNB type property with longer term

    Lee Hall Capital City Real Estate Group

    625 E Washington St, Monticello, FL 32344
  • /21

    $265,900

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

    1125 E Dogwood St, Monticello, FL 32344

    Must see this brand new home built by Southern Construction in the downtown Monticello area. Home is complete and ready for its new owners!! Home features 3 bed, 2 baths, granite countertops, upgraded trim package, vinyl plank flooring throughout, tile bathroom and laundry floors, and stainless appliance package. Come get this beautiful home before its gone!!

    Jared Parramore Coastwise Realty

    1125 E Dogwood St, 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
  • /67

    $995,000

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

    825 Rainey Run, Monticello, FL 32344

    Set on 10 private acres, this exceptional estate offers a lifestyle defined by space, serenity, and effortless luxury. Surrounded by nature and bordered by a tranquil private creek, the property feels like a personal retreat—yet remains perfectly designed for modern living and entertaining. Inside, 3,696 square feet of light-filled living space unfolds with soaring ceilings, expansive windows,

    Renee Dawkins Dawkins Realty LLC

    825 Rainey Run, Monticello, FL 32344
  • /18

    $179,900

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

    34 W Hummingbird Ln, Monticello, FL 32344

    New beautiful LVP flooring on mother in law suite side of the property and wdo repair underneath the new flooring!! 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

    Susan Gillespie Lord & Stanley Realty, Inc.

    34 W Hummingbird Ln, Monticello, FL 32344
  • /24

    $185,000

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

    490 E Palmer Mill Rd, Monticello, FL 32344

    This striking Victorian home built in 1892 and located near downtown Monticello. The home features original hardwood pine floors, soaring 12-foot ceilings, a large bay window with bench seating (and storage) and several fireplaces. The master bathroom has been completely redone and complements the spacious master bedroom. The exterior of the home has a wraparound front deck, a rear screened

    Van Drake Drake Realty, Inc.

    490 E Palmer Mill Rd, Monticello, FL 32344
  • /45

    $269,000

    • 4 Beds
    • 2 Baths
    • 1,812 Sq Ft

    685 E Washington St, Monticello, FL 32344

    Perfect brick family home right downtown! Walk to the veggie stand across the street and all the Monticello shops! Renovated 4-bed, 2-bath home. New roof!! New Custom Kitchen cabinets, granite counters, and SS Appliance package perfect for you home chefs. The open-plan kitchen opens directly into the dining and living room. New Flooring, Paint, Light fixtures, Custom closets and bookcases

    Lee Hall Capital City Real Estate Group

    685 E Washington St, Monticello, FL 32344
  • /4

    $75,000

    • Land
    • 0.29 Acre
    • $258,621 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
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