Homes for Sale near Turning Point

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  /51

  $425,000

  • 3 Beds
  • 2.5 Baths
  • 3,127 Sq Ft

  1628 N Jefferson Hwy, Monticello, FL 32344

  Picturesque, 4/2, brick beauty with a whimsical style that evokes the charm of a traditional storybook estate, with 3,217 sq. ft., bordering a large acreage holding on 2 sides. Beautiful attributes from the 1955 era such as cedar lined closet, crystal door knobs, original oak floors, wide baseboards, double bay windows, 24x10 screened porch and entertainment deck. Lifetime metal Roof! Boasting

  

  Lynette Sirmon

  All Realty Services

  (448) 288-6919

  1628 N Jefferson Hwy, Monticello, FL 32344
• 

  Explore Turning Point

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  /28

  $545,000

  • 3 Beds
  • 2 Baths
  • 1,810 Sq Ft

  512 Creekside Ct, Monticello, FL 32344

  Like New!Barely lived in 2020 Home in sought-after Crooked Creek Subdivision! Whole home Generac generator, fenced in backyard, screened in back porch along with all the interior upgrades! Easy commute to Thomasville and Tallahassee with the small-town charm of Monticello! This beautiful 3/2 is on a spacious cul-de-sac lot that backs up to the HOA-owned conservation property with a pond. This

  

  Chance Shutes

  Keller Williams Town & Country

  (448) 218-5546

  512 Creekside Ct, Monticello, FL 32344
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  /28

  $397,000

  • 3 Beds
  • 2.5 Baths
  • 2,373 Sq Ft

  1205 E Pearl St, Monticello, FL 32344

  Charming 1956 Mid-Century Home. Fully Renovated with Modern Touches. Welcome to this beautifully reimagined 1956 classic, where character meets contemporary luxury. Every inch of this home has been thoughtfully renovated, blending original charm with stylish, modern upgrades. Step inside to discover a bright, open-concept living space featuring new floors, recessed lighting, and large windows

  

  Brian Bachman

  Kelly & Kelly Properties, Inc

  (448) 327-5761

  1205 E Pearl St, Monticello, FL 32344
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  /57

  $699,000

  • 6 Beds
  • 3.5 Baths
  • 3,114 Sq Ft

  365 S Mulberry St, Monticello, FL 32344

  Historic soul. Modern substance. A rare circa-late 1800s home, beautifully restored and thoughtfully made NEW. Some houses simply endure... and some are given the rare chance to begin again. Better than New Construction! Just two blocks from the courthouse square in Monticello, Fl, this circa-late 1800s home—a classic Southern I-house shaped by Greek Revival influence—once stood quietly

  Lee Hall Capital City Real Estate Group

  365 S Mulberry St, Monticello, FL 32344
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  /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
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  /57

  $599,000

  • 7 Beds
  • 7 Baths
  • 5,139 Sq Ft

  625 E Washington St, Monticello, FL 32344

  Introducing a stunning 1.2 acre estate in the heart of Historic Downtown Monticello. The Simon-Ridgeway home was built in 1888 and boasts a generous 4,500 sq ft of living space and features 7 spacious bedrooms, 5 of which come with its own en-suite bathroom for ultimate privacy and convenience. City granted BNB status - making this perfect for an owner/occupier wanting to work from home and enjoy

  625 E Washington St, Monticello, FL 32344
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  /2

  $470,000 Open Sat 10AM - 5PM

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  51 Tarn Way, Monticello, FL 32344

  **Photos Coming Soon! Home will be move in ready May 20th. Amazing new construction 3 bedroom 2 bathroom plus office. Luxurious master suite, Kitchen made of dreams, this is a must see!

  Amber McKinney Hamilton Realty Advisors LLC

  51 Tarn Way, Monticello, FL 32344
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  /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

  4235 N Jefferson St, Monticello, FL 32344
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  /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

  107 S Tarn Way, Monticello, FL 32344
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  /70

  $795,000

  • 3 Beds
  • 2.5 Baths
  • 2,160 Sq Ft

  660 Whispering Hill, Monticello, FL 32344

  Set on 18+ acres of beautifully maintained pasture, this private country property is built for both everyday living, true equestrian use or small livestock farm. The land is the star- fully fenced with new wood fencing that cleanly defines multiple pastures, a peaceful pond, and wide open space to ride, graze and enjoy. The 6-stall horse barn is ready to work with paddocks attached to each stall,

  Catherine Hope All Realty Services

  660 Whispering Hill, Monticello, FL 32344
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  /31

  $625,000

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

  140 Shumard Ct, Monticello, FL 32344

  Discover this stunning 2,600+ sqft home built in 2021, offering the perfect blend of quiet country living and modern convenience. Features include: 4 spacious bedrooms and 3 full bathrooms 2 master bedrooms located downstairs Dedicated office/bonus room – ideal for work or hobbies Modern kitchen and open living spaces Attached 2-car garage Just minutes from downtown, providing a quick and easy

  140 Shumard Ct, Monticello, FL 32344
• 

  

  /19

  $470,000 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

  855 S Waukeenah St, Monticello, FL 32344
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  /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.

  Marlinda Bullock KILLEARN SALES CENTER,

  693 Tally Hills Dr, Monticello, FL 32344
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  /57

  $549,000

  • 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

  515 E Palmer Mill Rd, Monticello, FL 32344
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  /52

  $425,000

  • 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

  Robert Donovan Tallahassee Board of REALTORS®

  930 E Pearl St, Monticello, FL 32344
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  /46

  $450,000

  • 3 Beds
  • 2 Baths
  • 2,239 Sq Ft

  254 Woodland Dr, Monticello, FL 32344

  Custom home on 4.29 private acres~split bedroom plan~separate dining room~rocking chair front porch~screened porch overlooking wooded backyard~fireplace~upstairs room could be office or playroom~huge 40x40 workshop~FIRST TIME ON THE MARKET

  254 Woodland Dr, Monticello, FL 32344
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  /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-

  121 Shumard Ct, Monticello, FL 32344
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  /32

  $415,000

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

  3827 N Jefferson St, Monticello, FL 32344

  PRICED TO SELL AND READY FOR A QUICK CLOSING! Situated on 5 acres with private pond, this 3 bedroom 3 bath offers over 3000 sf of potential in a highly convenient location just minutes from Thomasville Ga and Monticello Fl. The home features a spacious primary suite, dedicated office, formal living and dining rooms, and a den with fireplace, plus a sun porch overlooking the peaceful acreage. With

  3827 N Jefferson St, Monticello, FL 32344
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  /19

  $157,000

  • Land
  • 10.54 Acres
  • $14,896 per Acre

  XX Ridge Rd, Monticello, FL 32344

  Leave Urbana and breathe... 10.54 acres in Exclusive Casa Bianca Ridge. Beautiful, rare lot on which to build your dream home. There is room to create a multi-generational paradise or your own personal playground. Nicely wooded parcel with a gentle stream deeper into the property. Very private. Survey in associated docs. Move quickly. Gate at Driveway. Do not enter the property without approval.

  Johanna Money The Williams Group

  XX Ridge Rd, Monticello, FL 32344
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  /66

  $399,000

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

  1012 S Main Ave, Monticello, FL 32344

  Tucked away on 5 private acres down a quiet, wooded road, this brick home offers 2,280 square feet with a split floor plan featuring 3 bedrooms and 2 baths, providing both space and functionality. New Roof November 2025, Well 2022, and septic drain field replaced 2016. Inside, you’ll find a cozy fireplace and a bright sunroom that brings the outdoors in, while the solid layout offers plenty of

  Robert Donovan Tallahassee Board of REALTORS®

  1012 S Main Ave, Monticello, FL 32344
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  /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

  2664 W Washington Hwy, Monticello, FL 32344
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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

  576 Cox Rd, Monticello, FL 32344
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  /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

  205 N Rhodes St, Monticello, FL 32344
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  /70

  $2,000,000

  • 7 Beds
  • 7 Baths
  • 5,756 Sq Ft

  305 Old Lloyd Rd, Monticello, FL 32344

  Welcome to a rare opportunity to own a true estate property where space, craftsmanship, and privacy come together on 18 beautiful acres. This impressive 7-bedroom, 5 full bath, 2 half bath two-story home offers a thoughtfully designed layout ideal for both everyday living and entertaining on a grand scale. Upstairs features 4 bedrooms and 2 full baths, while the downstairs includes 2 bedrooms,

  305 Old Lloyd Rd, Monticello, FL 32344
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  /11

  $170,000

  • 2 Beds
  • 1 Bath
  • 962 Sq Ft

  275 W High St, Monticello, FL 32344

  This cozy home is situated in the heart of charming Monticello within walking distance to all the local shops and restaurants. It's perfect for a starter home or someone wanting to downsize for simplicity. The home features an open concept with plenty of natural light from the many windows. Use two barstools at the kitchen island, or set a nice table for a more formal dining experience. The

  Heather Boyd FL-GA Realty & Auction

  275 W High St, Monticello, FL 32344
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  /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

  Amber LeDoux Destination Real Estate Corp

  490 N Cherry Ct, Monticello, FL 32344
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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.

  TBD Rainey Run, Monticello, FL 32344
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  /17

  $242,000

  • 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.

  1160 E Washington St, Monticello, FL 32344
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  /6

  $462,000

  • Land
  • 58.46 Acres
  • $7,903 per Acre

  1310 Piney Woods Rd, Monticello, FL 32344

  No sign on property, Must be accompanied. Nature and tree lover, timber value on the property, many great homesite locations. Pines and hardwoods, Power easement on the property. Community water and high speed internet through Tri County Electric. 3 separate parcel ID 3#s 03-1N-4E-0000-001F-0000, 03-1-4E-0000-001E-0000

  1310 Piney Woods Rd, Monticello, FL 32344
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  /70

  $2,785,850

  • 7 Beds
  • 7 Baths
  • 5,756 Sq Ft

  305 Old Lloyd Rd, Monticello, FL 32344

  Welcome to a rare opportunity to own a true estate property where space, craftsmanship, and privacy come together on 70 beautiful acres. Only 15 minutes to Whole foods & trader Joe's This impressive 7-bedroom, 5 full bath, 2 half bath two-story home offers a thoughtfully designed layout ideal for both everyday living and entertaining on a grand scale. Upstairs features 4 bedrooms and 2 full

  305 Old Lloyd Rd, Monticello, FL 32344
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  /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

  900 Ridge Rd, Monticello, FL 32344
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  /8

  $25,000

  • Land
  • 14,374 Sq Ft
  • $75,758 per Acre

  923 King St, Monticello, FL 32344

  Exceptional cleared corner lot with a concrete slab already in place—ready for your vision! City water and sewer connections are available, with electric at the road. Conveniently located just minutes from downtown Monticello. Motivated Sellers!

  Alicia Radtke All Realty Services

  923 King St, Monticello, FL 32344
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  /12

  $185,000

  • 3 Beds
  • 1 Bath
  • 1,312 Sq Ft

  670 Poplar St, Monticello, FL 32344

  Solid 3/1 SFR brick less than a mile from downtown Monticello! This quaint 1,312 sq ft home sits under a metal roof and only requires your vision and a little TLC to become a superb starter home or investment opportunity. It also includes an additional lot.

  Spencer Conner Keller Williams Town & Country

  670 Poplar St, Monticello, FL 32344
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  /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

  5936 Vista Rd, Monticello, FL 32344
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  /6

  $20,999

  • 2 Beds
  • 2 Baths

  10 S Front Ct, Monticello, FL 32344

  TAKE ADVANTAGE OF OUR MEMORIAL DAY MEGA MOVE-IN EVENT! If you purchase this home, receive 2 months FREE site rent and NO application fees. Offer expires May 31, 2026. Act fast! Restrictions apply. A beautifully refurbished home is coming soon-and it's definitely one to keep an eye on. Renovations are currently underway with an estimated completion date of 5/31 (subject to change), bringing fresh

  Patty Davis Jefferson Pines

  10 S Front Ct, Monticello, FL 32344
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  /70

  $1,325,000

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

  221 Kiley Dr, Monticello, FL 32344

  Welcome to a rare North Florida estate just minutes from Tallahassee—where luxury, land, and lifestyle come together. 221 Kiley Road is situated on expansive acreage in Monticello, and this private retreat offers the perfect blend of seclusion and convenience, located just a short drive from the heart of Tallahassee. For buyers seeking space, privacy, and versatility without sacrificing proximity

  221 Kiley Dr, Monticello, FL 32344
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  /4

  $550,000

  • 6,024 Sq Ft

  535 Hagan St, Monticello, FL 32344

  Rare Investor Opportunity: 7-Unit Residential Complex for Sale Don't miss this fantastic investment opportunity! This well-maintained 7-unit complex features: Six 3-bedroom, 1-bathroom units One 2-bedroom, 1-bathroom unit Walking distance to downtown – perfect for tenants seeking convenience Corner lot location with excellent visibility Designated parking spots for each unit 2023 Roof Whether

  535 Hagan St, Monticello, FL 32344
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  /9

  $198,000

  • 3 Beds
  • 1 Bath
  • 1,366 Sq Ft

  870 Shady Ln, Monticello, FL 32344

  Welcome to 870 Shady Lane in Monticello, Florida—a charming property that offers the perfect blend of privacy, space, and small-town appeal. Nestled on a quiet, tree-lined street, this home provides a peaceful retreat while still being conveniently close to the historic downtown district, local shops, and dining. Surrounded by mature trees and natural beauty, the property offers a serene setting

  Angela Graham Hamilton Realty Advisors LLC

  870 Shady Ln, Monticello, FL 32344
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  /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.

  1511 Spring Hollow Dr, Monticello, FL 32344
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  /12

  $128,900

  • Land
  • 6.86 Acres
  • $18,790 per Acre

  1407 S Jefferson St, Monticello, FL 32344

  This property presents a strong commercial opportunity along the highly visible Hwy 19 corridor. The property consists of approximately 6.8± acres of B-2 Highway Commercial land with over 400± feet of frontage on Highway 19, offering excellent exposure and accessibility in a growing retail and service trade area.The site includes an approved development plan; however, the only designated

  1407 S Jefferson St, Monticello, FL 32344

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