Homes for Sale in 32344

• 

  

  

  /8

  $22,000

  • Land
  • 1.18 Acres
  • $18,644 per Acre

  874 Flatwoods, Monticello, FL 32344

  A square 1.18 acres with paved road frontage. It has a powerline easement that runs through the center of the property. It has several, abandoned, old mobile homes on the property (no titles will be given, only bill of sale) and other structures. It has about 50% wet lands and a portion of the property lies within the flood zone. It is wooded, with some, young, easy to mulch, growth and some

  

  Lynette Sirmon

  All Realty Services

  (448) 218-0926

  874 Flatwoods, Monticello, FL 32344
• 

  

  

  /32

  $52,500

  • Land
  • 7.69 Acres
  • $6,827 per Acre

  983 Mays Rd, Lamont, FL 32344

  Affordable recreational parcel! Buy now, build later. Ultimate weekend escape or future homestead offering fun, freedom and fresh air- 7.69 serene acres split on both sides of scenic Mays Road. Enjoy the best of two offerings: West side 5.3 acres +/- with the pond, partially cleared with lush pasture, mature shade trees and wide-open space, perfect for horses, livestock, camping, four wheeling,

  

  Lynette Sirmon

  All Realty Services

  (448) 428-7600

  983 Mays Rd, Lamont, FL 32344
• 

  

  

  /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

  Shanna D'Attile

  Keller Williams Town & Country

  (850) 809-9683

  0000 Waukeenah Hwy, Monticello, FL 32344
• 

  

  

  /12

  $175,000

  • Land
  • 10.47 Acres
  • $16,714 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

  

  Jaquelynn Harrison-Cofty

  Property Finders Nguyen Realty

  (448) 334-6928

  5936 Vista Rd, Monticello, FL 32344
• 

  

  

  /42

  $469,000

  • 5 Beds
  • 2 Baths
  • 2,184 Sq Ft

  10283 Ashville Hwy, Greenville, FL 32331

  Amazing opportunity to own this private solar-powered farm with a large house! Beautiful and serene 16 acres with fruit trees, fields, lots of horse potential and 40 solar panels less than 5 years old. Nearly free electric! 5 Bedroom, 2 Bath with Large Eat-in Kitchen, Stainless Steel Appliances, Huge Great Room, Beautiful Hardwood Floors throughout main floor of the house, TWO Large Screened-in

  Lee Hall Capital City Real Estate Group

  10283 Ashville Hwy, Greenville, FL 32331
• 

  

  /17

  $27,900

  • Land
  • 1.25 Acres
  • $22,320 per Acre

  00 Gamble Rd Unit LotWP001, Monticello, FL 32344

  This 1.25-acre tract in Jefferson County, Florida, offers a balanced combination of accessibility, usable land, and proximity to outdoor recreation. Situated in the small unincorporated community of Wacissa FL, the property fronts State Road 59, providing year-round paved access. Its location places it less than 1.2 miles from Wacissa Springs Park and boat launch, a well-known destination for

  Thomas Lado

  00 Gamble Rd Unit LotWP001, Monticello, FL 32344
• 

  

  /38

  $419,000

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

  339 Silver Lake Rd, Monticello, FL 32344

  Gorgeous home on 5 acres mostly pasture. Open concept with vaulted ceilings; great entertainment/family home. Private setting; must see to believe.

  Steve Walker Steve C. Walker Realty, LLC

  339 Silver Lake Rd, Monticello, FL 32344
• 

  

  /19

  $350,000

  • Land
  • 70.45 Acres
  • $4,968 per Acre

  265 Neely Rd, Monticello, FL 32344

  Secluded, but not remote, this 70.45 acre tract in eastern Jefferson County, Florida would make an ideal hunting getaway property or a rural homesite. Virtually no ambient noise or light that will disturb the quiet woods. About half the tract is in 7-year-old planted loblolly pines and the rest is in natural woods and cypress ponds. You will be smack in the middle of some of the best deer and

  Dave Lewis

  265 Neely Rd, Monticello, FL 32344
• 

  

  /16

  $487,878

  • Land
  • 122 Acres
  • $3,999 per Acre

  0 James Noble Rd, Greenville, FL 32331

  Millwood Timberland East is a balanced property located in a great recreational market. The Ashville area is home to numerous trophy grade recreational properties and is known for exceptional whitetail, turkey and waterfowl hunting. This property features an efficient footprint with good access and internal road infrastructure. The uplands are planted with slash pine that are approximately 8

  Bryant Peace Saunders Real Estate

  0 James Noble Rd, Greenville, FL 32331
• 

  

  /42

  $1,125,000

  • 3 Beds
  • 1 Bath
  • 1,146 Sq Ft

  740 Kinsey Rd, Monticello, FL 32344

  Location: Jefferson County, FL Size: 155 acres Features: Rolling pastures Planted pines Natural hardwoods Pond Home: 1941 built 1,146 square feet Updated Outbuildings: With power Opportunities for workshops, storage, and more Additional Homesites: Breathtaking views Peaceful living Proximity: 10 miles from downtown Monticello, FL 5 miles to I-10 Wildlife: Deer Turkey Waterfowl

  Ben Jones Southern Land & Homes

  740 Kinsey Rd, Monticello, FL 32344
• 

  

  /20

  $570,000

  • Land
  • 71 Acres
  • $8,028 per Acre

  0 Aucilla Rd Unit 22696476, Monticello, FL 32344

  Located on Aucilla Rd in Monticello, FL, this versatile AG-5 property offers endless potential for residential, agricultural, and recreational use. The upland portion has been cleared, making it ideal for a homesite or multiple residences, with zoning allowing one unit per five acres and options for family transfers under county guidelines.For those looking to enjoy North Floridas natural

  Jeremiah Thompson Saunders Land

  0 Aucilla Rd Unit 22696476, Monticello, FL 32344
• 

  

  /38

  $7,800,000

  • Land
  • 3,089 Acres
  • $2,525 per Acre

  0 Turkey Scratch Rd Unit 18561092, Monticello, FL 32344

  Turkey Scratch Road Timberland is 3,089 Acres in Jefferson County just outside Monticello. The property features 616 Upland Acres (20%) / 2473 Wetland Acres (80%) and has 4 miles of combined road frontage on I-10, 4,450 feet of road frontage on Turkey Scratch Road, and 1,725 feet on Aucilla Road. It also has several miles of well-maintained internal roads for easy navigation and timber

  Richard Dempsey Saunders Land

  0 Turkey Scratch Rd Unit 18561092, Monticello, FL 32344
• 

  /2

  $748,000

  290 Oetinger Rd, Monticello, FL 32344

  Land Description for 290 Oetinger Rd, Campbell Farm Welcome to the enchanting Campbell Farm, a sprawling 68-acre property nestled in the serene landscapes of Northern Jefferson County, Florida. This unique piece of real estate offers a harmonious blend of natural beauty and practical amenities, making it an ideal sanctuary for nature lovers and those seeking a peaceful retreat. Property

  Charles Ward Hayden Outdoors Real Estate

  290 Oetinger Rd, Monticello, FL 32344
• 

  /2

  $25,000

  • Land
  • 0.39 Acre
  • $64,103 per Acre

  0 Tram Rd Unit 21473387, Monticello, FL 32344

  Wooded lot located in the Wacissa area of Jefferson County; 15 to Tallahassee. Community water available to hook up to.Copyright © 2025 Tallahassee Board of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

  Steve Walker Steve C. Walker Realty, LLC

  0 Tram Rd Unit 21473387, Monticello, FL 32344
• 

  

  /18

  $1,100,000

  • Land
  • 200 Acres
  • $5,500 per Acre

  0 Gum Swamp, Greenville, FL 32331

  Millwood Timberland West is a balanced recreational asset located in the Ashville, FL region. The internal road system meanders through the ecologically diverse landscape of pine plantations, live oaks and forested wetlands. The uplands are planted in slash pine that are approximately 15 years old with pockets of oak hammock and natural ponds. The ecosystem provides exceptional habitat for

  Bryant Peace Saunders Real Estate

  0 Gum Swamp, Greenville, FL 32331
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  /52

  $595,000

  • 3 Beds
  • 3 Baths
  • 2,376 Sq Ft

  532 Dills Rd, Monticello, FL 32344

  Gorgeous Pool Home situated on 5.55 acres featuring wood floors, crown molding, quartz countertops, black stainless appliances. Spacious primary suite with spa-like master bath, Rinnai water heater, 2020 Roof, 2023 concrete Pool, 2024 Generac whole home generator, 2024 HVAC, New 48x32 Pole Barn w/200 amp svc and concrete floors, 2023 Carport epoxy concrete by Deese Elite Floors

  Staci Pigott The Nova Group Realty

  532 Dills Rd, Monticello, FL 32344
• 

  

  /42

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,921 Sq Ft

  2497 Boston Hwy, Monticello, FL 32344

  Charming Hillside Country Retreat with Barn and Acreage. Welcome to your dream countryside escape! This beautifully maintained brick home sits peacefully on a hillside, surrounded by sprawling fields dotted with mature pecan trees. Inside, the home features a spacious open floor plan, perfect for entertaining or relaxing with family. The large kitchen offers ample workspace and storage, while the

  Pam Kelly Kelly & Kelly Properties, Inc

  2497 Boston Hwy, Monticello, FL 32344
• 

  

  /45

  $624,900

  • 3 Beds
  • 2.5 Baths
  • 2,546 Sq Ft

  181 Heritage Blvd, Monticello, FL 32344

  Highly Desirable Heritage Hills Location! Enjoy the perfect blend of privacy and convenience with this Craftsman-style home located on 3 serene acres, offering an easy commute to both Tallahassee and Monticello. The like-new residence boasts high-end finishes throughout, including crown molding, coffered ceilings, wainscoting, and a cozy gas fireplace. Relax or entertain year-round on the

  Pam Kelly Kelly & Kelly Properties, Inc

  181 Heritage Blvd, Monticello, FL 32344
• 

  

  /34

  $499,000

  • 8 Beds
  • 4 Baths
  • 4,806 Sq Ft

  2664 W Washington Hwy, Monticello, FL 32344

  FULLY RENOVATED TWO HOUSES, 1.9 acres, on picturesque US 90 near Monticello. UNDER $99/SF! These move-in-ready homes in good condition have a total of 8 bedrooms, 4 baths, and 4,806 s.f. living area. The MAIN HOUSE is a 1950’s era brick ranch-style home with new plumbing, new electric, fresh paint, new roof, whole home generator. Great opportunity for multiple generations to live side by side, or

  Heather Boyd FL-GA Realty & Auction

  2664 W Washington Hwy, Monticello, FL 32344
• 

  

  /39

  $529,000

  • 3 Beds
  • 2.5 Baths
  • 1,915 Sq Ft

  160 Lineage Ct, Monticello, FL 32344

  Beautiful 3-bedroom, 2.5-bath farmhouse offers privacy, charm, and modern conveniences. Built in 2016 and tucked away at the end of a cul-de-sac on 2.78 acres in desirable Heritage Hills. Home features an iron gate and long driveway—plenty of extra room for your boat or RV—along with a metal roof, a classic rocking chair front porch, large covered patio for entertaining and a 2-car garage.

  Leanne Groom The Naumann Group Real Estate

  160 Lineage Ct, 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
• 

  

  /19

  $430,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,865 Sq Ft

  173 Deerfield Ln, Monticello, FL 32344

  NEW CONSTRUCTION COMPLETE! Walk into this stunningly crafted three-bedroom, two-bathroom home that is perfectly rooted on a corner lot just a few miles from town. Situated on a full acre of land, this charming property is a rare find, free from HOA restrictions—giving you the freedom to personalize your space as you wish. Inside, you'll discover an open and welcoming floor plan that includes

  Caleb Stephens Silo Hill Properties

  173 Deerfield Ln, Monticello, FL 32344
• 

  

  /41

  $455,995 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
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  /43

  $315,000

  • 5 Beds
  • 2 Baths
  • 3,320 Sq Ft

  425 N Mulberry St, Monticello, FL 32344

  Charming 1020's Two-Story Home in the Heart of Downtown Monticello, Fl. Step back in time with this beautiful home nestled on a spacious 1/2 acre lot in the heart of Monticello. Bursting with character and potential, this property is perfect for those looking to restore a classic Southern gem. Inside, you will find original, wood ceiling, floors , and walls that are just waiting to be brought

  Pam Kelly Kelly & Kelly Properties, Inc

  425 N Mulberry St, Monticello, FL 32344
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  /33

  $190,000

  • 2 Beds
  • 2 Baths
  • 1,356 Sq Ft

  1065 S Mulberry St, Monticello, FL 32344

  This cozy home located in the heart of Monticello is the perfect 2/2 for a starter family looking to settle down or someone looking for a small, southern home in a quiet town! There is so much potential with good bones from the old hardwood floors to the floor-to-ceiling windows. This home is in walking distance to the roundabout near restaurants and antique shops or to the grocery store. With a

  Katherine Gonzalez Pearson Realty Inc.

  1065 S Mulberry St, Monticello, FL 32344
• 

  

  /64

  $1,200,000

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

  237 Valley View Ct, Monticello, FL 32344

  Unbelievable opportunity in Valley View Estates! Situated on 15+ (10+5) high-and-dry acres along the Leon/Jefferson County line, this unique property features two full-sized homes, a barn with additional living space, a heated/cooled workshop, and a screened pool with lanai. The custom-built main residence (~4000sf) offers 12’ ceilings, 3 bedrooms with ensuite baths, 2 additional bedrooms/flex

  Kelly Vinson Keller Williams Town & Country

  237 Valley View Ct, Monticello, FL 32344
• 

  

  /26

  $279,000

  • 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
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  /67

  $380,000

  • 3 Beds
  • 2 Baths
  • 1,722 Sq Ft

  525 Devane Rd, Monticello, FL 32344

  2024 custom-built, single story home on 3 acres near Jefferson Country Club with no HOA. Features 3 bedrooms plus a flexible bonus room—perfect for an office, studio, or guest space. Open floor plan with great room, bar seating, stainless appliances, high-end countertops, and LVP flooring throughout. Primary bath offers both a soaking tub and low-entry shower for accessibility. Storage

  Victoria Wilde Xcellence Realty

  525 Devane Rd, Monticello, FL 32344
• 

  

  /35

  $325,000

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

  1530 Sweetbay Ct, Monticello, FL 32344

  Like New! Barely lived in Home in the sought-after Crooked Creek Subdivision! 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 and the house is upgraded to include but not limited to stainless steel appliances, recessed lighting, vaulted ceilings, with granite and quartz countertops, and a stunning kitchen

  Chance Shutes Keller Williams Town & Country

  1530 Sweetbay Ct, Monticello, FL 32344
• 

  

  /61

  $40,000

  • Land
  • 3 Acres
  • $13,333 per Acre

  Vacant N Forest Ct, Monticello, FL 32344

  Check out this amazing 3+/- acre lot in the Aucilla Forest & Meadows Subdivision in beautiful Jefferson County, FL! This spacious lot would be the perfect place to build your dream home, or place your new manufactured/mobile home! Site built, or manufactured homes must be a minimum of 720 heated square feet. The land is currently wooded with some beautiful Florida hardwoods and pines. Clear out

  Jerrod Trainer Jerrod A Trainer & Associates

  Vacant N Forest Ct, Monticello, FL 32344
• 

  

  /9

  $120,000

  • Land
  • 2.01 Acres
  • $59,701 per Acre

  40 Westview Ln, Monticello, FL 32344

  Load up and take a ride to Lloyd Fl. located between Tallahassee and Monticello Fl. Being offered "AS IS" two 1 acre parcels 18-1N-4E-0108-000G-0030 & 18-1N-4E-0108-000G-0040 for a total of 2.01 acres! Power, septic and well on site, as well as access to city water. There is a 1989 mobile home on site that may be salvageable to the right buyer, or haul it off and prepare for a new build! Bring

  Alicia Radtke All Realty Services

  40 Westview Ln, Monticello, FL 32344
• 

  

  /41

  $329,500

  • 4 Beds
  • 2 Baths
  • 2,162 Sq Ft

  4081 Gamble Rd, Monticello, FL 32344

  Nestled on a serene 5-acre retreat, this charming storybook cottage feels like a hidden gem, yet it’s just 15 minutes from downtown Monticello’s quaint shops and restaurants. Tucked back from the road for ultimate privacy, this well-maintained home is surrounded by natural beauty, including native plants, wild azaleas, and lush greenery. Step onto the inviting front porch and into a warm,

  Malissa Henning EXP Realty, LLC

  4081 Gamble Rd, Monticello, FL 32344
• 

  

  /8

  $4,500,020

  • Land
  • 85.26 Acres
  • $52,780 per Acre

  0 Big Joe Rd Unit 2025007616, 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.

  Florie Gage Cornerstone Coastal Properties

  0 Big Joe Rd Unit 2025007616, Monticello, FL 32344
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  /28

  $239,000

  • 3 Beds
  • 2 Baths
  • 1,234 Sq Ft

  44 Pine Needle Trace, Monticello, FL 32344

  Charming Home with Open Floor Plan in Beautiful Monticello, FL! Welcome to this cozy well maintained home featuring an inviting open floor plan, warm wood-burning fireplace and vaulted ceilings that add space and character. French doors off the main living area open to a spacious deck overlooking the backyard. Freshly pained throughout the interior. Seller offering a flooring allowance with

  Pam Kelly Kelly & Kelly Properties, Inc

  44 Pine Needle Trace, Monticello, FL 32344
• 

  

  /46

  $178,000

  • 3 Beds
  • 3 Baths
  • 2,635 Sq Ft

  18 Perkins Williams Rd, Monticello, FL 32344

  Opportunity to finish a traditional-style home on 2.02 acres in the Monticello countryside. Built in 2001 by a local contractor, the home is approximately 80% complete and has never been lived in. The structure needs a new roof, HVAC system, water heater, bedroom flooring, and completion of the master bath. There is visible foundation settlement—cause and extent unknown. Located in a flood

  Ashley Hartsfield Keller Williams Town & Country

  18 Perkins Williams Rd, Monticello, FL 32344
• 

  

  /70

  $1,050,000

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

  825 Rainey Run, Monticello, FL 32344

  Welcome to this rare Monticello, FL luxury home for sale on 10 pristine acres with private creek frontage. This 4-bedroom, 4.5-bathroom estate spans nearly 3,700 square feet of elegant living space, offering the perfect blend of privacy, acreage, and modern luxury just minutes from Tallahassee. Property Highlights: 10 acres with a private creek 4 bedrooms, 3 with ensuite bathrooms 3,696 sq. ft.

  Renee Dawkins Ketcham Realty Group, Inc.

  825 Rainey Run, Monticello, FL 32344
• 

  

  /70

  $989,000

  • 4 Beds
  • 3 Baths
  • 4,600 Sq Ft

  2024 Old Lloyd Rd, Monticello, FL 32344

  Square footage includes both the main house is 3200 square feet with 4 bedrooms and 3 baths. New barn apartment is 1400 square feet with 2 bedrooms and 1 bath. This would be an amazing income producing property for short and/or long term rental property of barn apt, horse boarding stables ... or even a wedding venue. This breathtaking property checks ALL of the boxes! Please see associated

  Katherine Hansli Searcy The Naumann Group Real Estate

  2024 Old Lloyd Rd, Monticello, FL 32344
• 

  

  /43

  $285,000

  • 3 Beds
  • 2 Baths
  • 2,044 Sq Ft

  300 Cedar St, Monticello, FL 32344

  Price Improvement! ~ Welcome to 300 Cedar Street ~ Located a stone's throw from Monticello's charming downtown, yet quiet & private ~ Relax in a rocking chair & enjoy sitting on your HUGE 64x8 screened in porch that runs the entire length of the back of the home & overlooks the serene 1.5 acre lot ~ Built in 1958, this single story home is a sturdy brick ranch style with 3 Bedrooms, 2 Baths,

  Jonathan Rigsby Spotlight Real Estate

  300 Cedar St, Monticello, FL 32344
• 

  

  /38

  $799,000

  • 5,139 Sq Ft

  625 E Washington St, Monticello, FL 32344

  Amazing Investment Opportunity! 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 as a rooming house with tenants. New roof 2024, new HVAC 2022 and mini splits, New kitchen and bathrooms 2022, Tankless Hot water

  Lee Hall Capital City Real Estate Group

  625 E Washington St, Monticello, FL 32344
• 

  

  /45

  $275,000

  • 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 all those 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

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