257

Madison County FL Homes for Sale

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  • /41

    $300,000

    • 3 Beds
    • 2.5 Baths
    • 2,682 Sq Ft

    186 NW Whispering Pines Loop, Madison, FL 32340

    Seller Motivated...New roof in 2024! This custom-built home offers exceptional space and craftsmanship with 2,682 sq. ft. heated (4,428 sq. ft. under roof) and soaring 9–11 ft. ceilings. Enjoy multiple living areas, a formal dining room, and a spacious kitchen with custom cabinetry, newer appliances, and a walk-in pantry. The large primary suite features a jetted tub, walk-in shower, and double

    Agent Photo

    Lynette Sirmon

    All Realty Services

    (850) 660-0205

    186 NW Whispering Pines Loop, Madison, FL 32340
  • /61

    $75,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    6859 SW County Road 14, Madison, FL 32340

    Welcome to “The Pool House” – a peaceful country retreat with incredible potential! Originally built in 2000 beside an inground pool (now filled and beautifully grassed over), this solid concrete-block structure is fully dried-in with a brand-new 2025 roof and a strong slab foundation—ready for you to customize and complete. Seller receives water from the well, will need a little while to get

    Agent Photo

    Lynette Sirmon

    All Realty Services

    (448) 233-3070

    6859 SW County Road 14, Madison, FL 32340
  • /26

    $125,000

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft

    699 NE Hillside Terrace, Lee, FL 32059

    Just reduced for your rehab pleasure. HVAC just fixed. Bring your best offer to this country home with porch made of lumber off the land. Plenty to do based on your credentials. Lots of potential. Metal roof. Quite neighborhood.

    Agent Photo

    John (Jeb) Stewart

    THE DARBY-ROGERS CO.

    (448) 334-8661

    699 NE Hillside Terrace, Lee, FL 32059
  • /26

    $216,900

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft

    313 SW Horry Ave, Madison, FL 32340

    Historic Beauty with Modern Comfort in the Heart of Madison Step into the past with all the ease of modern living at 313 SW Horry Ave, a timeless 1920-built home in Madison's treasured historic district. Located on a corner lot in the well-loved Town of Madison subdivision, this classic single-story home offers the perfect blend of old-world charm and thoughtful updates. Inside, you'll find 1,680

    Agent Photo

    William E Ramos

    Integrity Key Realty LLC

    (448) 334-6313

    313 SW Horry Ave, Madison, FL 32340
  • /25

    $235,000

    • Land
    • 40.49 Acres
    • $5,804 per Acre

    Lot 121 SW Pacific Dr, Greenville, FL 32331

    Lot 121 – 40.49 Acres in Gated Aucilla Plantation – Greenville, FL Lots 115 and 122 also available! Discover the perfect blend of seclusion, recreation, and investment potential with this beautiful 40.49-acre parcel located in Aucilla Plantation, a private, gated subdivision in Greenville, FL. This exclusive, monitored community spans over 3,000 acres and offers miles of private roads ideal for

    Agent Photo

    Carrie Taylor

    The American Dream

    (448) 233-2434

    Lot 121 SW Pacific Dr, Greenville, FL 32331
  • /38

    $85,000

    • 3 Beds
    • 3 Baths
    • 934 Sq Ft

    409 SW Obadiah St, Greenville, FL 32331

    Tiny house but with 3 Bedrooms and 3 Bathrooms. Yes you read that right...there are three BEAUTIFUL bathrooms. Easy to maintain city lot sized 40 ft. deep by 100 ft. wide. Located in the heart of Greenville, Florida this home is thoughtfully updated offering a delightful blend of old character and modern design. The brand new kitchen features beautiful cabinetry, sleek countertops, pendant

    Agent Photo

    Lynette Sirmon

    All Realty Services

    (448) 208-8423

    409 SW Obadiah St, Greenville, FL 32331
  • /58

    $437,000

    • 3 Beds
    • 2 Baths
    • 1,712 Sq Ft

    11942 SW Overstreet Ave, Lamont, FL 32336

    A LAND REMEMBERED-ESCAPE to OLD FLORIDA Welcome to your private 29+ acre rustic retreat in the heart of rural Madison County, FL - a rare and unrestriced recreational paradise where you can hunt, fish, farm, and play to your heart's content. Tucked away in the beauty of Old Florida, this property offers: a unique A-Fame home full of rustic character, multiple outbuildings for storage or creative

    Agent Photo

    Barry Kelly

    Kelly & Kelly Properties, Inc

    (448) 202-5031

    11942 SW Overstreet Ave, Lamont, FL 32336
  • /12

    $215,000

    • Land
    • 49.54 Acres
    • $4,340 per Acre

    Lot 115 SW Pier Rd, Greenville, FL 32331

    Lot 115 - 49.54 Acres in Gated Aucilla Plantation – Greenville, FL Welcome to your private slice of North Florida paradise! Nestled in the highly desirable Aucilla Plantation, this expansive 49.54-acre parcel offers the perfect blend of privacy, natural beauty, and recreational opportunity. Located within a gated and monitored 3,000+ acre community, this lot provides both seclusion and peace of

    Agent Photo

    Carrie Taylor

    The American Dream

    (448) 202-5075

    Lot 115 SW Pier Rd, Greenville, FL 32331
  • /22

    $799,500

    • Land
    • 123 Acres
    • $6,500 per Acre

    3282 NW Us 221, Greenville, FL 32331

    The Little Aucilla River Runs through it! This is truly a one of a kind property. With a mix of pasture, pines and hardwood hamocks and low lands, it is ideal for hunting as well as a small farming operation. The Little Aucilla River runs through the property offering unique recreational oportunities. There are two ponds as well as a number of established food plots. There are two mobile homes

    Agent Photo

    Buddy Witmer

    Steve C. Walker Realty, LLC

    (850) 641-7416

    3282 NW Us 221, Greenville, FL 32331
  • /51

    $215,000

    • 4 Beds
    • 2 Baths
    • 1,643 Sq Ft

    338 NE Kel Ln, Lee, FL 32059

    Newly Remodeled 2005 4/2 DWMH in Lee, FL for $215,000!!! There are VERY FEW properties and homes for sale in this quiet little sanctuary town. This home is nestled at the end of Kel Lane and backed up to a 80 ac tract of timber to provide peace and quiet. This home boasts brand new laminate flooring throughout, tile showers, new tub in BA #2, new ceiling fan in the LR, new kitchen cabinets, new

    Agent Photo

    Brad Smith

    United Country Smith & Associates

    (448) 428-4896

    338 NE Kel Ln, Lee, FL 32059
  • /25

    $235,000

    • Land
    • 40.5 Acres
    • $5,802 per Acre

    Lot 122 SW Oregon Trail, Greenville, FL 32331

    Lot 122 – 40.5 Acres in Gated Aucilla Plantation – Greenville, FL Adjacent Lot 121 Also Available! Located in the heart of Aucilla Plantation, this beautiful 40.5-acre parcel offers the perfect mix of privacy, recreation, and investment potential within a secure, gated community spanning over 3,000 acres in Greenville, FL. The property features approximately 30 acres of merchantable pine

    Agent Photo

    Carrie Taylor

    The American Dream

    (448) 256-2969

    Lot 122 SW Oregon Trail, Greenville, FL 32331
  • /60

    $125,000

    • 2 Beds
    • 2 Baths
    • 1,369 Sq Ft

    863 NW Whippoorwill Dr, Greenville, FL 32331

    SELLER MOTIVATED! Peaceful Country Retreat on Whippoorwill Way – This well-kept 2009 2 bedroom / 2 bathroom single-wide (16' x 76') offers a comfortable and serene setting along a quiet country lane between Monticello and Greenville in Madison County, Florida. The home features a large master ensuite, huge walk-in closet, and convenient washer/dryer hookup inside. The property includes well,

    Agent Photo

    Lynette Sirmon

    All Realty Services

    (448) 217-3393

    863 NW Whippoorwill Dr, Greenville, FL 32331
  • /70

    $588,500

    • 5 Beds
    • 6 Baths
    • 3,814 Sq Ft

    588 NW Pickle Ln, Madison, FL 32340

    This spacious 5-bedroom, 6-bath brick home—priced below appraisal— sits on 5 beautiful acres surrounded by peace and privacy. Offering two stories plus a heated and cooled basement, the home features a remodeled kitchen with stainless steel appliances, a full-size oven, and granite countertops. Flooring throughout includes hardwood, parquet, and slate. Enjoy multiple living spaces including a

    Dennis L Coxwell Keller Williams Town & Country

    588 NW Pickle Ln, Madison, FL 32340
  • /2

    $270,000

    • Land
    • 40.02 Acres
    • $6,747 per Acre

    0 SE Pebble Ridge St Unit 23525783, Lee, FL 32059

    This 40-acre property is part of Glenwood Forest. It includes 12 acres of pines that are over 20 years old, while the remaining 28 acres were planted less than a year ago. This land is a blank canvas, offering endless possibilities for your imagination. Manufactured homes are permitted. It is located on a county-maintained road and is surrounded by other large parcels of land.

    TINA DONALDSON Tina Donaldson with AFG Tristate Realty

    0 SE Pebble Ridge St Unit 23525783, Lee, FL 32059
  • /18

    $150,000

    • Land
    • 30.68 Acres
    • $4,889 per Acre

    0 Vacant Sw Jeanette Cir, Madison, FL 32340

    30.68 Acres of Prime Vacant Land in Madison - Ideal for Investment or Development! Parcels 28-1N-09-5083-000-000 & 28-1N-09-5083-001-000This 30.68-acre parcel offers a fantastic opportunity for investors and developers in a highly sought-after location. Situated within the city limits of Madison, this property is surrounded by land owned by the City of Madison, offering both privacy and

    Jessica Groover Southern Land & Homes

    0 Vacant Sw Jeanette Cir, Madison, FL 32340
  • /19

    $562,800

    • Land
    • 268 Acres
    • $2,100 per Acre

    0 County Line Rd Unit 19604811, Lee, FL 32059

    268 acres in the middle of over 600,000 acres of timberlands and private land owners. The watering holes and surrounding woods create an idyllic habitat for a wide variety of wildlife. Sit in your stand and look in awe as deer, turkeys, and more make their home in these woods. The roads have been recently mowed and repaired. Walk across the road on the southwest corner and you will be in

    TINA DONALDSON Tina Donaldson with AFG Tristate Realty

    0 County Line Rd Unit 19604811, Lee, FL 32059
  • /16

    $214,200

    • Land
    • 102 Acres
    • $2,100 per Acre

    0 SW Brown Rd, Lee, FL 32059

    102 acres sectioned from a larger parcel in the middle of over 600,000 acres of timberlands and private land owners. Deer, turkey and hogs are in abundance in this area. This parcel of land is situated where Madison, Lafayette and Taylor county all meet. No HOA or deed restrictions. Electric is more than 5 miles away so bring those generators or solar panels to enjoy hunting at its best!

    TINA DONALDSON Tina Donaldson with AFG Tristate Realty

    0 SW Brown Rd, Lee, FL 32059
  • /25

    $300,000

    • Land
    • 12.77 Acres
    • $23,493 per Acre

    1420 S State Road 53, Madison, FL 32340

    Madison Commercial 13 is ready for business. Located on SR 53 8/10 of a mile south of downtown Madison, Florida. The property boasts 512' of highway frontage on SR 53 and is conveniently located to both downtown Madison and Interstate 10. The site has an abandoned railroad spur that has the possibility of being connected to the Gulf Atlantic Railroad. This is a prime commercial site suited for

    Greg Driskell Saunders Land

    1420 S State Road 53, Madison, FL 32340
  • /54

    $699,000

    • Land
    • 45.05 Acres
    • $15,516 per Acre

    3859 SE Cr 255, Lee, FL 32059

    This property consists of 45.05 acres of pasture land featuring large pecan trees. The entire area is fully fenced and cross-fenced. It includes a 961-square-foot home with an in-ground pool, as well as two RV hook-ups. Additionally, there is a horse barn with a tack room, a large workshop located at the back of the property, and an all-purpose building measuring 100 by 20 feet in the front

    TINA DONALDSON Tina Donaldson with AFG Tristate Realty

    3859 SE Cr 255, Lee, FL 32059
  • /63

    $700,000

    • 4 Beds
    • 2 Baths
    • 2,316 Sq Ft

    397 SE Schooner Way, Lee, FL 32059

    Take a look at this private, like-new home on 40 acres of long leaf pines in Madison County. The home is totally powered by solar panels, offering sustainable and self-sufficient energy. Enjoy contemporary fixtures, a fully equipped kitchen, ample storage, and all the amenities required for comfortable living. The master suite exudes comfort and relaxation, offering an enormous soaker tub and

    Katy Yanossy POOLE REALTY INC.

    397 SE Schooner Way, Lee, FL 32059
  • /53

    $123,200

    • Land
    • 56 Acres
    • $2,200 per Acre

    0 County Line Rd Unit 18882882, Lee, FL 32059

    56 acres located in Madison county, FL in the city of Lee. It is a total of 631 acres and it is being offered in several different sized parcels. This land has abundant wildlife; Deer, Turkey and Hogs. It is connected to over 600,000 acres of timberlands and private land owners. There are no deed restrictions or HOA. You may have a camper or have a metal building. The land is combination of

    TINA DONALDSON Tina Donaldson with AFG Tristate Realty

    0 County Line Rd Unit 18882882, Lee, FL 32059
  • /7

    $165,000

    • Land
    • 75 Acres
    • $2,200 per Acre

    0 County Line Rd Unit 19597151, Lee, FL 32059

    75 acres with exceptional wildlife! In the middle of over 600,000 acres. No HOA and no deed restrictions. Buy this land and create your own hunting camp to your specifications. Madison county is known for its big bucks, it is on the list of top 10 counties for buck registrations. Come snag that prize buck today!

    TINA DONALDSON Tina Donaldson with AFG Tristate Realty

    0 County Line Rd Unit 19597151, Lee, FL 32059
  • /69

    $3,285,000

    • 4 Beds
    • 5 Baths
    • 5,395 Sq Ft

    1706 NW Radford Denson Rd, Greenville, FL 32331

    Cypress Hill – 198+/- Acres of Premier Recreational and Luxury Living in Madison County, Florida Welcome to Cypress Hill, a meticulously crafted 198-acre estate designed for both high-end living and exceptional recreation. From the moment you pass through the gate, it’s clear this isn’t just land—it’s a lifestyle. Every detail, from the curated topography to the architectural choices, reflects

    Ben Jones Southern Land & Homes

    1706 NW Radford Denson Rd, Greenville, FL 32331
  • /11

    $87,400

    • Land
    • 38 Acres
    • $2,300 per Acre

    0 SW Prine Rd, Lee, FL 32059

    Great hunting tract consisting of 38 acres, and an abundance of deer, turkey and hogs roam this property daily. Madison county is known for its big bucks, it is on the list of top 10 counties for typical and non-typical buck scores. Set up your own hunting camp and enjoy the outdoors! 6 miles from electric so bring your generators and camper

    TINA DONALDSON Tina Donaldson with AFG Tristate Realty

    0 SW Prine Rd, Lee, FL 32059
  • /55

    $900,000

    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft

    4087 NW Honey Lake Rd, Greenville, FL 32331

    Expansive 96-Acre FarmsteadEmbrace the serenity of naturePerfect mix of lush pasture and majestic hardwoodsCharming 1,450 Sq Ft HomeCozy and inviting interiorComfortable living spaces for the whole family Detached 1BR / 1BA CottageGreat for guests, extended family, or rental incomeOffers privacy and

    Ben Jones Mossy Oak Properties Southern Land and Homes, LLC

    4087 NW Honey Lake Rd, Greenville, FL 32331
  • /2

    $269,000

    • Land
    • 40.24 Acres
    • $6,685 per Acre

    SE County Road 255th, Lee, FL 32059

    Very Nice high & dry 40 Acre tract on paved County Road. Planted Long Leaf Pines. Great Recreational Tract.

    Dale Herring Herring Realty Group

    SE County Road 255th, Lee, FL 32059
  • /30

    $1,795,000

    • Land
    • 554 Acres
    • $3,240 per Acre

    NW Hawks Ave, Greenville, FL 32331

    The Hawks Ave 554 is a great recreational property located in northern Madison County, Florida. There are several roads throughout the property and openings for food plots to help create this into a sportsman's haven. Along with an amazing game population, there are over 40 acres of merchantable planted pines, helping make this a great investment. Just a short drive from Valdosta, Thomasville,

    Daniel Lanier Saunders Land

    NW Hawks Ave, Greenville, FL 32331
  • /74

    $1,249,000

    • 4 Beds
    • 2 Baths
    • 1,560 Sq Ft

    2681 U S 221 Hwy N, Greenville, FL 32331

    193 +/- acres of absolutely TURN-KEY ranchland. Move-in ready - bring your family and livestock and start your cattle operation! Located in North Florida's prime cattle country, this ranch is only 25 minutes from downtown Madison, FL, and just 45 minutes from Tallahassee. Everything has been meticulously maintained, with brand new fencing, new 4/2 mobile home, ponds, 2 wells and productive soils

    Gary Silvernell

    2681 U S 221 Hwy N, Greenville, FL 32331
  • /15

    $189,200

    • Land
    • 86 Acres
    • $2,200 per Acre

    0 SW Prine Rd Unit 19604535, Lee, FL 32059

    86 acres with an abundance of deer, turkey and hogs. Madison is known for its big bucks. Madison is in the top 10 counties on the buck registry. No deed restrictions or HOA. Build your camp to your desires. Bring an RV or put in a metal building, the choice is yours. Bring a generator too, electric is over 5 miles away.

    TINA DONALDSON Tina Donaldson with AFG Tristate Realty

    0 SW Prine Rd Unit 19604535, Lee, FL 32059
  • /31

    $412,500

    • Land
    • 74.72 Acres
    • $5,521 per Acre

    NW Co Rd 253, Greenville, FL 32331

    The North Madison 75 tract is a beautiful property just south of the Georgia line in picturesque Madison County, Florida. Perfect for growing timber, whitetail deer, and turkeys, make this parcel your personal recreational getaway. Easy access from I-10 via SR 53 and just a dozen or so miles outside of the small town of Madison, the property features over 1/4 mile of paved road frontage.

    Daniel Lanier Saunders Land

    NW Co Rd 253, Greenville, FL 32331
  • /36

    $790,500

    • Land
    • 93 Acres
    • $8,500 per Acre

    650 Flowers Rd, Madison, FL 32340

    93 Acres of Prime Hunting & Recreational Land Madison County, FLDiscover your own private outdoor paradise on this 93-acre tract nestled in the heart of Madison County, Florida. This exceptional property offers a perfect blend of mature hardwoods, pine stands, open clearings, and natural wetlands creating ideal habitat for deer, turkey, hogs, and small game.With established

    Ben Jones Mossy Oak Properties Southern Land and Homes, LLC

    650 Flowers Rd, Madison, FL 32340
  • /131

    $1,100,000

    • 6 Beds
    • 7.5 Baths
    • 6,600 Sq Ft

    11110 Andrews, Greenville, FL 32331

    Discover a rare opportunity to own a one-of-a-kind 38+ acre lakefront estate in the heart of North Floridaan absolute haven for sportsmen, nature lovers, and those seeking a more self-sufficient, off-the-grid lifestyle. With over 6,600 sq. ft. of living space, this 6-bedroom, 6.5-bathroom custom-built home sits high and dry on the shores of Lake Andrew, offering unmatched views, total privacy,

    Hope Webb The American Dream

    11110 Andrews, Greenville, FL 32331
  • /83

    $975,000

    • Land
    • 42.32 Acres
    • $23,039 per Acre

    3637 SE County Road 255, Lee, FL 32059

    Features include a 3 bedroom, 3 bath home, 4 outbuildings, and a large pole barn. The property is partially fenced, with several sides securely enclosed. Large, majestic oaks are scattered throughout. The 4 outbuildings have electric and a slab with a new metal roof. The home received a new roof in 2025, new stove top and over in November 2025. Pasture land produces Coastal Bermuda and is baled

    TINA DONALDSON Tina Donaldson with AFG Tristate Realty

    3637 SE County Road 255, Lee, FL 32059
  • /40

    $960,000

    • 1 Bed
    • 1 Bath

    0 Vacant Ne Duval Pond Rd, Madison, FL 32340

    OVERVIEW160 acres fronting the Duval Pond located in Madison County, FL! Featuring frontage on the Duval Pond with a great interior road system. Several beautiful homesites are scattered about, offering an excellent opportunity to escape to the serenity of Rural America for that forever home or weekend getaway! RECREATIONThis tract offers an array of outdoor

    Ben Jones Mossy Oak Properties Southern Land and Homes, LLC

    0 Vacant Ne Duval Pond Rd, Madison, FL 32340
  • /13

    $87,400

    • Land
    • 38 Acres
    • $2,300 per Acre

    0 SW Prine Rd Unit 20907962, Lee, FL 32059

    38 acres being sectioned from a larger parcel. Loaded with deer, turkey and hogs! 6 miles into the woods, secluded with a deeded road access. No deed restrictions or HOA. Come build your paradise in the woods and enjoy the great outdoors! Bring your generator or solar panels, electric is 6 miles away.

    TINA DONALDSON Tina Donaldson with AFG Tristate Realty

    0 SW Prine Rd Unit 20907962, Lee, FL 32059
  • /56

    $1,202,275

    • Land
    • 126.45 Acres
    • $9,508 per Acre

    Vacant Sw Cr 360a, Madison, FL 32340

    126.45 Acres Madison County, FloridaPrime Location: Just minutes from I-10 and Downtown Madison, FL convenient yet privateLand Features:Producing hay fields for ongoing agricultural incomePlanted pine with pine straw contract in place steady cash flow opportunityTowering majestic oaks creating natural beauty and shadeMultiple

    Ben Jones Mossy Oak Properties Southern Land and Homes, LLC

    Vacant Sw Cr 360a, Madison, FL 32340
  • /12

    $80,500

    • Land
    • 35 Acres
    • $2,300 per Acre

    0 SW Brown Rd, Lee, FL 32059

    35 acres being sectioned from a larger parcel. This land has abundant wildlife; Deer, Turkey and Hogs. It is connected to over 600,000 acres of timberlands and private landowners. There are no deed restrictions or HOA. You may have a camper or have a metal building. The land is combination of pines and hardwoods. It is 6 to 7 miles into the woods on legally deeded roads. Several roads border the

    TINA DONALDSON Tina Donaldson with AFG Tristate Realty

    0 SW Brown Rd, Lee, FL 32059
  • /66

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    2959 SE Winquepin Sr Lee Unit FL 32059, Lee, FL 32059

    40.02 Acres in Madison County, FL!Prime Location: Just 15 miles to downtown Madison & 6 miles to I-10High & Dry Land: 100% usable no flood worriesHome Onsite: 2016 1,800 sq ft mobile home Big Barn Bonus: 30x60 barn for equipment, toys, or animalsWildlife Galore: Healthy deer & turkey population for hunting or watchingRiver Life: Short dirt road

    Ben Jones Mossy Oak Properties Southern Land and Homes, LLC

    2959 SE Winquepin Sr Lee Unit FL 32059, Lee, FL 32059
  • /20

    $315,000

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

    5001 NW Little Cat Rd, Madison, FL 32340

    Hunter’s Paradise — 30 Acres of Prime North Florida Land in Madison, FL Escape to the quiet woods of Madison County, where 30 acres of pristine Florida land are waiting for your next outdoor adventure. Tucked away off a peaceful country road, this property offers privacy, wildlife, and endless opportunity — the perfect mix for hunters, campers, and nature lovers alike. Deer, turkey, and small

    William Gibson Southern Land & Homes

    5001 NW Little Cat Rd, Madison, FL 32340
  • /70

    $120,000

    • Land
    • 18.29 Acres
    • $6,561 per Acre

    0 SE River Rd Unit 25641257, Lee, FL 32059

    Check out this awesome 18.29+/- acre tract located in the southern part of Madison County, FL! Just minutes from the Lafayette County line. This beautiful property is naturally wooded with some nice Florida hardwoods, and scattered pines! This would make an excellent hunting, or recreational property! Wildlife sign is abundant on the property. Particularly whitetail deer tracks, fresh scrapes,

    Jerrod Trainer Jerrod A Trainer & Associates

    0 SE River Rd Unit 25641257, Lee, FL 32059

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