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Jefferson County FL Homes for Sale

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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

    Caleb Stephens Silo Hill Properties

    535 Hagan St, Monticello, FL 32344
  • /59

    $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 2,880 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

    Catherine Hope All Realty Services

    1012 S Main Ave, Monticello, FL 32344
  • /31

    $625,000

    • 4 Beds
    • 3 Baths
    • 2,706 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

    Caleb Stephens Silo Hill Properties

    140 Shumard Ct, Monticello, FL 32344
  • /19

    $475,000 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
  • /63

    $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
  • /56

    $165,000

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

    629 Smokehouse Farms Dr, Greenville, FL 32331

    2,280 square foot, 1998 mobile home on 5.01 acres located in Aucilla Shores, in Greenville, FL (Jefferson County). The expansive layout includes (4) bedrooms, (3) full bathrooms, a living room, dining room, and separate family room. The Master Bedroom includes an en suite, perfect for a home office or additional private living space, double walk-in closets, and a large bathroom with a shower

    Agent Photo

    Brenna Kelly-Ward

    Kelly & Kelly Properties, Inc

    (448) 202-5795

    629 Smokehouse Farms Dr, Greenville, FL 32331
  • /38

    $558,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,233 Sq Ft

    35 Tarn Way, Monticello, FL 32344

    2026 Nailed It Tallahassee Parade of Homes Entry! **Photos are of previous build home will have different finishes. Home will be move in ready May 20th. Amazing new construction 4 bedroom 3 bathroom. Luxurious master suite, Kitchen made of dreams, this is a must see!

    Amber McKinney Hamilton Realty Advisors LLC

    35 Tarn Way, Monticello, FL 32344
  • /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
  • /57

    $589,900

    • 4 Beds
    • 3 Baths
    • 2,660 Sq Ft

    513 Creekside Ct, Monticello, FL 32344

    HOME HAS BRAND NEW LUXURY PLANK VINYL~ 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
  • /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,

    Agent Photo

    Chance Shutes

    Keller Williams Town & Country

    (448) 327-4992

    305 Old Lloyd Rd, Monticello, FL 32344
  • /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.

    Nicholas Harrington Keller Williams Town & Country

    XX Ridge Rd, Monticello, FL 32344
  • /69

    $555,000 New Construction

    • 4 Beds
    • 2 Baths
    • 1,945 Sq Ft

    64 Sanctuary Dr, Monticello, FL 32344

    Just WOW this beautiful new construction home, with top-of-the-line custom finishes. This home gives you all the luxury you are looking for - a primary suite with stunning tongue and groove wood tray ceilings, master bath with stand-alone soaking tub, walk-in shower, double vanity with quartz countertops, an oversized walk-in custom master closet with built-ins. As you approach the living area,

    Agent Photo

    Chance Shutes

    Keller Williams Town & Country

    (448) 305-5882

    64 Sanctuary Dr, Monticello, FL 32344
  • /57

    $599,900

    • 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. You'll fall in love with the intricately designed hardwood floors that flow throughout the home,

    Lee Hall Capital City Real Estate Group

    625 E Washington St, Monticello, FL 32344
  • /51

    $325,000

    • 4 Beds
    • 3 Baths
    • 2,223 Sq Ft

    155 E Seminole Ave, Monticello, FL 32344

    Set along one of Monticello’s main routes, this 1950s home offers a rare chance to create something truly your own—whether that’s a residence, a business, or a thoughtful mix of both, with flexible Business/Residential zoning already in place. Sitting on 0.60 acres with over 2,200 square feet, the layout is surprisingly adaptable, with 4 bedrooms and 3 full bathrooms, including multiple ensuite

    Catherine Hope All Realty Services

    155 E Seminole Ave, 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
  • /21

    $230,000

    • 3 Beds
    • 2 Baths
    • 1,331 Sq Ft

    10567 S Salt Rd, Lamont, FL 32336

    Why pay new construction prices when this 3 Bdrm, 2 Bath, home has already been rebuilt? Every major component has been updated offering modern living on 1 acre. Located near the Gulf Coast and convenient to Tallahassee and Perry. Looking for Florida Sunshine and room to garden at an affordable price? This one has new walls & ceilings, new doors & windows, new bathrooms, new paint, new fixtures,

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    Lynette Sirmon

    All Realty Services

    (448) 200-5718

    10567 S Salt Rd, Lamont, FL 32336
  • /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
  • /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

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    Carmen Mansfield

    McClellan Realty, LLC

    (448) 200-3241

    167 Phelps Rd, Lamont, FL 32336
  • /61

    $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

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    Pam Kelly

    Kelly & Kelly Properties, Inc

    (448) 200-3108

    9901 Gamble Rd, Monticello, FL 32344
  • /22

    $95,000

    • 3 Beds
    • 2 Baths
    • 1,125 Sq Ft

    295 W J Hatchett Rd, Lamont, FL 32336

    Investor special with great potential! Situated on approximately .75 acres in Jefferson County, this 2022 mobile home offers a fantastic opportunity for the right buyer to complete the final steps and make it their own. Conveniently located just minutes from I-10 for easy access to Tallahassee and only about 10 minutes to downtown Monticello, the property combines rural space with excellent

    Catherine Hope All Realty Services

    295 W J Hatchett Rd, Lamont, FL 32336
  • /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

    Agent Photo

    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

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    Barry Kelly

    Kelly & Kelly Properties, Inc

    (448) 428-7669

    398 Tecumseh Rd, 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

    Agent Photo

    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

    Agent Photo

    Barry Kelly

    Kelly & Kelly Properties, Inc

    (448) 242-0428

    576 Cox 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
  • /50

    $550,000

    • 3 Beds
    • 2 Baths
    • 2,083 Sq Ft

    5301 Gentle Breeze Dr, Tallahassee, FL 32309

    BRING ANY AND ALL OFFERS!!!! A true diamond in the rough, perfectly positioned on Lake Miccosukee. A bass fisherman’s dream come true. You truly won’t find another gem like this. This stunning 10-acre waterfront estate sits right at the water’s edge, offering wide-open space ideal for horses, outdoor adventures, and total privacy. Surrounded by abundant wildlife, this property is perfect for

    Lindsay Pearson Pearson Realty Inc.

    5301 Gentle Breeze Dr, Tallahassee, FL 32309
  • /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
  • /33

    $329,000

    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft

    233 Attatulga Rd, Lamont, FL 32336

    Spacious Triplewide mobile home on 5 private acres, plenty room for family and guests, 4 bedrooms, 3 baths, open floor plan. Huge master suite (12x25), additional bedroom with private bathroom. Huge deck for entertaining or just enjoying nature. Open pole barn and carport. Enjoy peaceful country living with ample outdoor space for animals, hobbies, or recreation. Conveniently located with easy

    Agent Photo

    Barry Kelly

    Kelly & Kelly Properties, Inc

    (448) 208-8700

    233 Attatulga Rd, Lamont, FL 32336
  • /32

    $99,000

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

    290 Parkway Pines Ct, Monticello, FL 32344

    BOM! NEW HVAC to be installed April 10-15th. 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. New HVAC

    Alicia Radtke All Realty Services

    290 Parkway Pines Ct, 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.

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    Barry Kelly

    Kelly & Kelly Properties, Inc

    (448) 231-1638

    220 Eaton St, Monticello, FL 32344
  • /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 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

    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

    Agent Photo

    Barry Kelly

    Kelly & Kelly Properties, Inc

    (448) 218-0015

    4589 Ashville Hwy, 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.

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    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

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    Pam Kelly

    Kelly & Kelly Properties, Inc

    (448) 231-5287

    640 Nautilus Dr, 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

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    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

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