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Homes for Sale near Turning Point

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  • /7

    $135,000

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

    576 Cox Rd, Monticello, FL 32344

    Looking for privacy, this 10 acres provides an ideal homesite with some clearing for your homesite completed. The balance of the land is woorded with a mix of hardwoords and pines. Some of the land is in welands/flood which provides a nice buffer for privacy and a wildlife habitat. There is a well/pump (no tank), an older septic, and power pole. 15 ft easement leads to the property. Located just

    Agent Photo

    Barry Kelly

    Kelly & Kelly Properties, Inc

    (448) 242-0428

    576 Cox Rd, Monticello, FL 32344
  • /43

    $489,000

    • 4 Beds
    • 2 Baths
    • 1,864 Sq Ft

    4235 N Jefferson St, Monticello, FL 32344

    Shows like new and impeccably maintained, this beautiful brick home sits on 5.14 acres tucked away in a serene pine forest, offering both tranquility and convenience with an ease commute to Thomasville, GA and Monticello, Fl. This spacious 4-bedroom home features a thoughtfully designed layout, including a large screened back porch perfect for relaxing or entertaining while enjoying the peaceful

    Agent Photo

    Pam Kelly

    Kelly & Kelly Properties, Inc

    (448) 202-4022

    4235 N Jefferson St, Monticello, FL 32344
  • /37

    $345,000

    • 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) 218-4974

    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
  • /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.

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    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.

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    Barry Kelly

    Kelly & Kelly Properties, Inc

    (448) 231-4719

    1160 E Washington St, Monticello, FL 32344
  • /45

    $789,000

    • 4 Beds
    • 2.5 Baths
    • 2,376 Sq Ft

    900 Ridge Rd, Monticello, FL 32344

    Tucked just outside of historic Monticello, this exceptional 11+ acre property offers a refined rural lifestyle without sacrificing everyday convenience. This Jefferson County gem features a much sought after combination of home, acreage, pool, barn and location. The residence itself is over 2300 square feet and is filled with natural light throughout. The open floor plan is perfect for

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    Brian Bachman

    Kelly & Kelly Properties, Inc

    (448) 200-2138

    900 Ridge Rd, 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

    Advantage Premier Realty LLC

    (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.

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    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.

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    Pam Kelly

    Kelly & Kelly Properties, Inc

    (448) 334-6781

    tbd Jackson St, Monticello, FL 32344
  • /19

    $239,000

    • 3 Beds
    • 1 Bath
    • 1,164 Sq Ft

    220 Eaton St, Monticello, FL 32344

    Very convenient location in the heart of Monticello. Excellent condition. Very good condition, new roof, new windows, newer flooring throughout. 10X12 storage shed.

    Agent Photo

    Barry Kelly

    Kelly & Kelly Properties, Inc

    (448) 231-1638

    220 Eaton St, Monticello, FL 32344
  • /30

    $175,000

    • 3 Beds
    • 1 Bath
    • 1,662 Sq Ft

    167 Phelps Rd, Lamont, FL 32336

    Charming 3BR/1BA home with incredible potential, nestled on a gorgeous and private one acre lot with no neighbors in sight. The property is filled with beautiful Camelia trees, creating a serene and picturesque setting. A newer workshop sits out back - perfect for hobbies, storage, or projects. Major update includes a 2025 metal roof. Crawlspace inspection has identified needed repairs to

    Agent Photo

    Carmen Mansfield

    McClellan Realty, LLC

    (448) 200-3241

    167 Phelps Rd, Lamont, FL 32336
  • /41

    $525,000

    • 4 Beds
    • 2.5 Baths
    • 2,134 Sq Ft

    121 Shumard Ct, Monticello, FL 32344

    Beautiful, like-new 2022 farmhouse-style home located in the sought after Crooked Creek area. This spacious 2134 sq ft home features 4 bedrooms and 2.5 baths on a generous .85 acre lot, ideally situated on a quiet cul-de-sac on the west side of Monticello. The open-concept layout offers elegant coffered ceilings crown molding and a cozy gas fireplace with built-in shelving in the living room-

    Agent Photo

    Pam Kelly

    Kelly & Kelly Properties, Inc

    (448) 200-1052

    121 Shumard Ct, 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
  • /41

    $550,000

    • 5 Beds
    • 2 Baths
    • 2,268 Sq Ft

    398 Tecumseh Rd, Monticello, FL 32344

    Charming Cape Cod-style home tucked away on 5 acres just minutes to downtown Monticello. This one owner home has been lovingly maintained and reflects years of care and pride of ownership. With over 2200 square feet of living space, the home offers a comfortable layout. The main floor features three bedrooms, one bath, a welcoming living room with a gas fireplace, dining area, kitchen and a

    Agent Photo

    Barry Kelly

    Kelly & Kelly Properties, Inc

    (448) 428-7669

    398 Tecumseh Rd, Monticello, FL 32344
  • /49

    $615,000

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

    3873 N Jefferson Hwy, Monticello, FL 32344

    Stunning 4 Bedroom, 5 Bath Home on 9.73 Acres with Large Detached Garage plus Oversized Attached 2 Car GarageLocated just north of Monticello, 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 is not located in a flood zone or HOA. Built in 2007, the home features

    Stephanie Fox Mossy Oak Properties Southern Land and Homes, LLC

    3873 N Jefferson Hwy, 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
  • /38

    $449,900

    • 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
  • /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
  • /11

    $65,000

    • Land
    • 3 Acres
    • $21,667 per Acre

    1309 Cook Rd, Monticello, FL 32344

    Investor Special on 3 Acres in Monticello, FL! Opportunity awaits with this 3-acre property just 20 minutes from Tallahassee! A mobile home is present on property that will require significant renovation—taken down to the shell and rebuilt—or removal entirely, this has been priced accordingly for investors or buyers looking to start fresh.The existing home has experienced water damage to the

    Alicia Radtke All Realty Services

    1309 Cook Rd, Monticello, FL 32344
  • /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
  • /57

    $200,000

    • 2 Beds
    • 1 Bath
    • 1,741 Sq Ft

    265 W Seminole Ave, Monticello, FL 32344

    You must see this -Charming all-brick corner-lot home ideally located directly across from the Legion Hall and the entrance to Monticello Ecological Park—plus just a short walk to midtown shops and restaurants. The screened In front porch welcomes you inside. Inside, you’ll find wood floors (including beneath the carpet in the bonus room) and a layout that offers flexibility for today’s living.

    Karen Gillispie Keller Williams Town & Country

    265 W Seminole Ave, Monticello, FL 32344
  • /31

    $275,000

    • 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
  • /3

    $415,500

    • Land
    • 22.13 Acres
    • $18,775 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
  • /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
  • /29

    $95,000

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    290 Parkway Pines Ct, Monticello, FL 32344

    Explore this three bedroom, two bathroom mobile home located on a little over half an acre in the Parkway Pines subdivision in Monticello Florida! Featuring newer carpet/vynil flooring throughout the home, a spacious front porch, and plenty of yard space for outdoor activities! Home is being offered "AS IS". Metal roof is about 3-5 years old. Original HVAC, duct work replaced summer 2025. All

    Alicia Radtke All Realty Services

    290 Parkway Pines Ct, Monticello, FL 32344
  • /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
  • /36

    $674,900

    • 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
  • /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
  • /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
  • /44

    $615,000

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

    3873 N Jefferson St, Monticello, FL 32344

    Stunning 4 Bedroom, 5 Bath Home on 9.73 Acres with Large Detached Garage plus Oversized Attached 2 Car Garage. Located just north of Monticello, 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 is not located in a flood zone or HOA. Built in 2007, the home features 10-foot

    Stephanie Dobson Southern Land & Homes

    3873 N Jefferson St, Monticello, FL 32344
  • /35

    $375,000

    • 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. New mini split

    Tom Grasberger Gaff's Realty Company

    925 E Pearl 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
  • /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
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