Homes for Sale in 32344

• 

  

  

  /61

  $545,000

  • 3 Beds
  • 2 Baths
  • 3,706 Sq Ft

  2184 Tram Rd, Monticello, FL 32344

  BEAUTIFULLY UPDATED ACREAGE HOME ON 22 ACRES WITH POND AND BLUEBERRIE FIELDS! UNIQUE PROPERTY WITH ACRES OF BLUEBERRIES, plus 60x 23, 4 bay garage with heated and cooled office, gym or storage space, 22x23 pole barn and 64x32 large red barn with kitchen and 2 bathrooms, 2 gazebo's, storage shed and more! There is plenty of room to roam on this beautiful property with over $195,000 of updates! The

  Penny Herman Penny Herman Realty

  2184 Tram Rd, Monticello, FL 32344
• 

  

  

  /19

  $400,000

  • 4 Beds
  • 3 Baths
  • 2,870 Sq Ft

  49 Foggy Ln, Monticello, FL 32344

  Welcome to 49 Foggy Lane in Monticello, FL—an exceptional opportunity to own a spacious property with endless potential! This 2,870 sq ft home features 4 generously sized bedrooms and 3 full bathrooms, along with a dedicated office space—perfect for remote work or added flexibility. Enjoy cozy evenings by the wood-burning fireplace, creating a warm and inviting atmosphere throughout the home. The

  Chellise Harrell Superior Realty Group LLC

  49 Foggy Ln, 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

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 202-4022

  4235 N Jefferson 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

  

  Carmen Mansfield

  McClellan Realty, LLC

  (448) 200-3241

  167 Phelps Rd, Lamont, FL 32336
• 

  

  

  /52

  $989,000

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

  9901 Gamble Rd, Monticello, FL 32344

  A LAND REMEMBERED-Discover a rare opportunity to own over 40 acres of land where conservation and nature meet comfort and privacy. Scenic walking trails wind throughout the property, creating a peaceful retreat for nature lovers. The home features major upgrades, including a new roof, Pella double-paned energy-efficient windows, and a new water heater. Inside, enjoy 9 foot ceilings throughout the

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 200-3108

  9901 Gamble Rd, Monticello, FL 32344
• 

  

  /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-

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 200-1052

  121 Shumard Ct, Monticello, FL 32344
• 

  

  /27

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,774 Sq Ft

  8156 Waukeenah Hwy, Monticello, FL 32344

  Rare Find! Country Living on 1 Acre-No HOA! Enjoy peaceful country living on a full 1-acre property with no HOA restrictions. This spacious 1774 square foot home features 3 bedrooms and 2 bathrooms with a bright open concept layout. The home features LVP flooring throughout, fresh interior paint in main living area, and a new roof in 2023 for added piece of mind. The primary suite includes a

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 288-3209

  8156 Waukeenah Hwy, 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

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 428-7669

  398 Tecumseh Rd, 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
• 

  

  /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

  

  Brian Bachman

  Kelly & Kelly Properties, Inc

  (448) 200-2138

  900 Ridge Rd, Monticello, FL 32344
• 

  

  /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

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 242-0428

  576 Cox Rd, Monticello, FL 32344
• 

  

  /48

  $1,000,000

  • 8 Beds
  • 6.5 Baths
  • 5,560 Sq Ft

  237 Valley View Ct, Monticello, FL 32344

  Opportunities like this are rare! You've been seeking close in country life. Enjoy the perfect balance of privacy and convenience on 15 acres with a true Estate. A main home, guest home, efficiency apartment, barn, climate controlled storage, life sized doll house with electric, screened pool, and whole home generator offer the perfect multi-generational set up and breathtaking sunset views just

  Kelly Vinson Keller Williams Town & Country

  237 Valley View Ct, Monticello, FL 32344
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  /60

  $525,000

  • 4 Beds
  • 2 Baths
  • 1,838 Sq Ft

  965 Robert Thompson Rd, Monticello, FL 32344

  Quiet country living near everything Tallahassee FL offers. Beautiful 4BR/2BA home on 5 acres. Split bedroom plan. Living room opens to large kitchen and breakfast nook. Sunroom not included in SqFt. Primary bedroom with tray ceilings, private bath with a jetted tub and separate shower. Plantation shutters throughout home. Generator installed 2017. 2 car attached garage and a large detached

  Suzanne McGhee Mattox Realty, Inc

  965 Robert Thompson 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
• 

  

  /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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  /35

  $650,000

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

  498 Heritage Blvd, Monticello, FL 32344

  Welcome to this beautifully crafted 3-bedroom, 2.5-bath Craftsman-style home nestled in the highly sought-after Heritage Hills community. Perfectly positioned on a spacious 2.99-acre lot, this property offers the ideal blend of privacy, room to roam, and timeless curb appeal—all with an easy commute to both Tallahassee and Monticello. Step inside to an inviting open-concept living area designed

  Brian Moser Bulldog Properties, LLC

  498 Heritage Blvd, 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
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  /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
• 

  

  /41

  $575,000

  • 4 Beds
  • 2.5 Baths
  • 2,431 Sq Ft

  234 Legacy Way, Monticello, FL 32344

  Highly Desirable Heritage Hills- Minutes from Tallahassee ! Welcome to this beautifully crafted 4-bedroom, 2.5 bath Craftsman-style home. Situated on a spacious 3- acre lot, this home offers privacy, room to roam, and timeless curb appeal. Step inside to an inviting open-concept living area featuring a cozy gas fireplace with custom buily-in bookshelves- perfect for relaxing or entertaining. The

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 230-5054

  234 Legacy Way, 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
• 

  

  /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
• 

  

  /3

  $79,900

  • Land
  • 1.39 Acres
  • $57,482 per Acre

  TBD Pineview Rd, Monticello, FL 32344

  Very nice high and dry 1.39 acres, ideal for new home or mobile home. New Well.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 333-1312

  TBD Pineview Rd, 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
• 

  

  /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.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 231-1638

  220 Eaton St, Monticello, FL 32344
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  /11

  $45,000

  • Land
  • 2.5 Acres
  • $18,000 per Acre

  1 W Meadow Rd, Monticello, FL 32344

  2.5 Acres of land, partially cleared for home-site. Private quiet road. All high and dry ready to build your homestead. mobile homes okay. Close to aucilla river. Convenient to Monticello, FL and Thomasville Ga. Valdosta and Tallahassee 45 minutes away. Horse Friendly area. Owner financing options available.

  Starbuck Rissman Steve C. Walker Realty, LLC

  1 W Meadow Rd, 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
• 

  

  /49

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 3,832 Sq Ft

  4589 Ashville Hwy, Monticello, FL 32344

  Nestled on 5.56 acres of fenced pastureland, this stunning estate, is framed by majestic oak trees and welcomes you through a private gated entrance. From the rocking chair front porch to the thoughtfully designed interior, this property offers the perfect blend of luxury and country living. Living room kitchen combination with the stone fireplace creating a warm and inviting focal point. The

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  (448) 218-0015

  4589 Ashville Hwy, 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
• 

  

  /60

  $700,000

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft

  925 Hiawatha Farms Rd, Monticello, FL 32344

  Custom hurricane-resistant/efficiency home on 3.6 private acres in a gated equestrian community, just 17 miles east of Tallahassee and 1 mile to I-10 (Exit 217). Built in 2013, this 2,112 sq ft home features 4 bedrooms, 3 full baths, and 9’ ceilings throughout. Constructed with Nudura ICF 12” insulated concrete exterior walls for superior strength, energy efficiency, and sound insulation.

  

  Joann Jacobs

  Coldwell Banker Hartung

  (448) 230-7519

  925 Hiawatha Farms Rd, Monticello, FL 32344
• 

  

  /16

  $549,000

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  640 Nautilus Dr, Monticello, FL 32344

  Secluded 56.37 Acres with Metal Building & Living Quarters -Western Jefferson County. This property offers privacy, versatility and room to build or expand. The land features a 2880 sq ft heavy-gauged metal building designed for both residential and workshop use. Second floor includes 1200 sf of living space currently unfinished featuring two bedrooms, kitchen and living area and one bath. A

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 231-5287

  640 Nautilus Dr, Monticello, FL 32344
• 

  

  /38

  $599,900 New Construction

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

  261 Hiawatha Farms S, Monticello, FL 32344

  Welcome to this stunning new construction masterpiece, meticulously designed and built by the esteemed Kasdorf Homes, LLC. This craftsman beauty is awaiting its first owners and will be ready for occupancy by the beginning of May. Spanning an impressive 2134 square feet, this home offers a spacious and open concept floor plan, perfect for modern living. The split floor plan provides privacy and

  Ross Kozloski Kozloski Realty, LLC

  261 Hiawatha Farms S, Monticello, FL 32344
• 

  

  /54

  $525,000

  • 4 Beds
  • 3 Baths
  • 2,784 Sq Ft

  70 Generation Ct, Monticello, FL 32344

  Wow! Special opportunity to add your personal touches! Design your dream kitchen! Craftsman style home features a roomy floorplan with lots of storage nooks and crannies, huge primary suite waiting for your perfect finishes, open kitchen and all nestled on private 4.45 acres. Many of the are there to finish trim, there’s extra stone and extra tile. LVP and ceramic tile flooring throughout home,

  Lee Duggar Re/Max Professionals Realty

  70 Generation Ct, 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

  

  Pam Hoveland

  Landcorp, Inc.

  (448) 231-4689

  490 N Cherry Ct, Monticello, FL 32344
• 

  

  /70

  $700,000

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

  1627 Lloyd Creek Rd, Monticello, FL 32344

  Enjoy the gorgeous water views from the porch of this like-new, 2022 built home! A Gated driveway leads to your 5 acre parcel on a beautiful 10 acre spring-fed lake with great fishing. 6 ft windows and 8x8 sliding doors allow the open living, dining, and kitchen areas to view the sunny outdoors. Kitchen features a large island with seating area, stainless appliances, gas stove, and fridge with

  Nan Greynolds The Naumann Group Real Estate

  1627 Lloyd Creek Rd, Monticello, FL 32344
• 

  

  /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
• 

  

  /8

  $450,000

  • Land
  • 85.26 Acres
  • $5,278 per Acre

  1899 Big Joe Rd, Monticello, FL 32344

  Known for its white tail deer, hog and turkey populations, this 85.26 acres in Jefferson County, FL would make a perfect hunting camp. Pristine pine tree property just minutes from Interstate 10 / Exit 225. Ideal Country Estate or weekend get-away. Seller financing available to qualified buyer.

  Tom Woodyard Woodyard & Associates, LLC

  1899 Big Joe Rd, Monticello, FL 32344
• 

  

  /24

  $174,900

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  963 Quail Ln, Monticello, FL 32344

  Great location for this property in Lloyd Acres. The property has 2.26 acres of partially wooded area. The property consists of the single family home, detached garage/carport/workshop and a singlewide mobile home. The vinyl sided home will need some repair and updating but has tremendous potential. The detached garage is large with 2 stalls. The mobile home is in need of a total renovation (or

  Van Drake Drake Realty, Inc.

  963 Quail Ln, Monticello, FL 32344
• 

  

  /13

  $65,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  40 Westview Ln, Monticello, FL 32344

  Don't judge this home by its exterior!! The outside siding shows significant deterioration, which is fully reflected in the price. However, once inside, you'll find a livable interior that's far more functional than first impressions suggest. This double-wide is currently occupied and offers ;an opportunity for a buyer willing to look past the exterior and focus on the potential within. Not

  Alicia Radtke All Realty Services

  40 Westview Ln, Monticello, FL 32344
• 

  /2

  $40,000

  • Land
  • 2.3 Acres
  • $17,391 per Acre

  0 Mallard Ln Unit 394437, Monticello, FL 32344

  Escape to peace & privacy, and with this beautiful 2.30-acre homesite located in the Lloyd Acres / Mallard Lane area of Jefferson County. Whether you’re planning your next home, a weekend retreat, or a smart land investment, this property offers the perfect blend of rural living with convenient access to Monticello and Tallahassee. Enjoy the natural surroundings, abundant trees, and quiet country

  Hunter Bowden Keller Williams Town & Country

  0 Mallard Ln Unit 394437, 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.

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  (448) 233-5401

  1511 Spring Hollow Dr, Monticello, FL 32344

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