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Homes for Sale in 32344

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  • /5

    $275,000

    • Land
    • 3.30 Acres
    • $83,333 per Acre

    xxx W Washington St, Monticello, FL 32344

    **Prime Investment Opportunity: 3.3 Acre Lot in Monticello Growth Area** For Sale: A 3.3 acre lot situated in the highest traffic area of Monticello, offering unparalleled visibility and access. Located in the largest growth zone of Monticello, this property is ideally positioned to benefit from the eastward expansion of Tallahassee. It is conveniently near several of the most desirable

    Agent Photo

    Tina Coombs

    Big Fish Real Estate Services

    (850) 318-4086

    xxx W Washington St, Monticello, FL 32344
  • /3

    $145,350

    • Land
    • 51 Acres
    • $2,850 per Acre

    000 Kinsey Rd, Monticello, FL 32344

    60.6 Acres of prime hunting/recreational land. Paved road access with owned easement. Wolf creek runs thrugh part of the property. $2850/Acre

    Agent Photo

    Buddy Witmer

    Steve C. Walker Realty, LLC

    (850) 726-3832

    000 Kinsey Rd, Monticello, 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

    Agent Photo

    Shanna D'Attile

    Keller Williams Town & Country

    (850) 809-9683

    0000 Waukeenah Hwy, Monticello, FL 32344
  • /36

    $95,000

    • 4 Beds
    • 2 Baths
    • 2,152 Sq Ft

    955 E Pearl St, Monticello, FL 32344

    Circa 1920, 3 Bdrm, 2 Bath, has 2 extra lots available for a total purchase price of $165,000.00, Home is fully livable as it is and can be purchased for $95,000.00 with lot size 109x135. However, to qualify for insurance, updates to the wiring & roof replacement will be necessary. Sold "AS IS" with right to inspect. Price reflects need for renovations and will not pass 4 Point Inspection! Two

    Agent Photo

    Lynette Sirmon

    All Realty Services

    (850) 757-1853

    955 E Pearl St, Monticello, FL 32344
  • /17

    $24,997

    • Land
    • 0.86 Acre
    • $29,066 per Acre

    98 Cox Rd, Monticello, FL 32344

    Small, tract of land "bring the chickens, build a chicken coop" located between Monticello, FL and Thomasville, GA. This UNIQUE, .86 acres of land with its deeply, rich, flora and native fauna is thick and abundant with many different types of indigenous species. Use the 10x20 storage building as a primitive bunkhouse cabin, specimen container, wildlife observatory or weekend landing pad/fun

    Agent Photo

    Lynette Sirmon

    All Realty Services

    (850) 990-4427

    98 Cox Rd, Monticello, FL 32344
  • /16

    $609,878

    • Land
    • 122 Acres
    • $4,999 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

    $1,200,000

    • 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
  • /6

    $816,000

    • Land
    • 68 Acres
    • $12,000 per Acre

    290 Oetinger Rd, Monticello, FL 32344

    68 acres in Northern Jefferson County Fl. Beautiful Pasture surrounded by Old Growth Pine Timber. Pond sits in the middle of the property and this property has a Plantation on Two sides. Well, Septic Tank and Barn are included with property. Deer and Turkey are abundant with an excellent spot for a Dove Field. Minutes from Monticello Fl. and Thomasville Ga. this is an ideal spot for someone

    Charles Ward Hayden Outdoors Real Estate

    290 Oetinger Rd, Monticello, FL 32344
  • /3

    $471,000

    • Land
    • 58 Acres
    • $8,057 per Acre

    1310 Piney Woods Rd, Monticello, FL 32344

    This property contains three tax ID number. The other 2 numbers are: 03-1N-4E-0000-001F-0000 and 03-1N-4E-0000-001E-0000. A total of 58.46 acres; currently there is no for sale sign on the property. Very nice wooded tract with great location; easy access to Tallahassee. It has timber potential and would be a good home tract also. Community water is available for the property along with high

    Steve Walker Steve C. Walker Realty, LLC

    1310 Piney Woods Rd, Monticello, FL 32344
  • /42

    $495,900 New Construction

    • 3 Beds
    • 2 Baths
    • 2,061 Sq Ft

    350 Oconee, Monticello, FL 32344

    Welcome to Covey Run, a private estate community in the heart of Monticello. Your new 3 bedroom 2 bath 2 car garage sits on 2.24 acres. Home features open floor plan with primary on-suite and large walk-in closet. Kitchen is ready for the chef in mind with gas range and plenty of room for prep. Living room features 10 foot ceilings, fireplace and opens to a sunroom. House has Generac Home

    Steve Walker Steve C. Walker Realty, LLC

    350 Oconee, Monticello, FL 32344
  • /18

    $1,300,000

    • Land
    • 200 Acres
    • $6,500 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 and ready to be thinned. The next owner will be able to thin the pines to their specification in

    Bryant Peace Saunders Real Estate

    0 Gum Swamp, Greenville, FL 32331
  • /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
  • /26

    $750,000

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

    5080 Ashville Hwy, Monticello, FL 32344

    Welcome to your dream getaway nestled on the pristine bank of Silver Lake! This beautiful cabin style home has 3-bedroom, 2-bathroom and seamlessly combines rustic charm with modern conveniences, making it the perfect escape for families or those seeking tranquility on the edge of town. The cabin showcases stunning hardwood floors that add warmth and elegance to the living space. Enjoy your

    Caleb Stephens Waypoint Properties East

    5080 Ashville Hwy, Monticello, FL 32344
  • /42

    $632,000

    • 4 Beds
    • 3.5 Baths
    • 3,862 Sq Ft

    3873 N Jefferson St, Monticello, FL 32344

    Stunning 4 Bedroom, 3.5 Bath Home on 9.73 Acres with Large Detached Garage plus Oversized Attached 2 Car Garage Located just north of 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 not located in a flood zone or HOA. Built in 2007, the home features 10-foot ceilings,

    Stephanie Dobson Southern Land & Homes

    3873 N Jefferson St, Monticello, FL 32344
  • /42

    $649,000

    • 3 Beds
    • 2.5 Baths
    • 2,560 Sq Ft

    181 Heritage Blvd, Monticello, FL 32344

    Craftsman style house in Heritage Hills subdivision~ The house features 3 bedrooms/2 bathrooms and is energy efficient (Green Certified) ~ Luxurious hardwood flooring and a deluxe primary bathroom with separate jetted tub & large shower ~ Custom built-in cabinets in the living room and office ~ Regal craftsman style interior trim throughout and stainless-steel appliances ~ Full Solar with

    Mariela Bartens Coldwell Banker Hartung

    181 Heritage Blvd, Monticello, FL 32344
  • /42

    $505,000

    • 4 Beds
    • 3 Baths
    • 2,555 Sq Ft

    4287 Bassett Dairy Rd, Monticello, FL 32344

    Rare COUNTRY Farmhouse OASIS AWAITS! – Discover the perfect blend of rustic charm in this stunning 5-bedroom, 3-bathroom home, nestled on five fully fenced acres of picturesque pastureland. Located just 15 minutes from downtown Monticello, this peaceful retreat offers breathtaking views, abundant wildlife, and plenty of space for your pets to roam. Step inside to a beautifully updated,

    Destiny Jones Keller Williams Town & Country

    4287 Bassett Dairy Rd, Monticello, FL 32344
  • /25

    $434,900

    • 4 Beds
    • 2 Baths
    • 1,809 Sq Ft

    115 Crooked Creek Ln, Monticello, FL 32344

    New Construction in Crooked Creek by Hannon Construction on .72 acre lot! This open plan features 4 bedrooms, 2 bathrooms and a 2 car garage (floor plan and survey are attached in associated docs). Wood LVP flooring throughout (tile in baths), GE stainless appliances, electric fireplace and pre-wired for security and surround sound. *Estimated completion date is May 1, 2025. There is still time

    Amber Renaud The Nova Group Realty

    115 Crooked Creek Ln, Monticello, FL 32344
  • /42

    $735,000

    • 4 Beds
    • 2.5 Baths
    • 3,911 Sq Ft

    4589 Ashville Hwy, Monticello, FL 32344

    PRICED $35,000 BELOW RECENT APPRAISAL!! Welcome to your forever home on the most stunningly manicured 5.5+ acres nestled in a serene country setting. This is truly a showstopper starting right at the beginning with its grand gated entrance leading to a picturesque rocking chair front porch and a modern farmhouse aesthetic. Walking in the front door you’ll be greeted by a cathedral vault ceiling,

    Devin Lohman Lohman Realty LLC

    4589 Ashville Hwy, Monticello, FL 32344
  • /34

    $465,000

    • 4 Beds
    • 3 Baths
    • 2,076 Sq Ft

    376 Tecumseh Rd, Monticello, FL 32344

    Gorgeous multigenerational, ranch style, 4 Bedroom/3 Bath home with 5th room that can be used as an office or additional bedroom. Perfect for a growing or downsizing family! Home rests on 4.60 acres of outdoor, partially wooded paradise. Enjoy tranquility from the all-season rear porch-removable panels allow you to turn room into a screened porch in minutes. Many recent updates include freshly

    Casey Skelton Pearson Realty Inc.

    376 Tecumseh Rd, Monticello, FL 32344
  • /40

    $565,000

    • 3 Beds
    • 3 Baths
    • 2,661 Sq Ft

    141 Shumard Ct, Monticello, FL 32344

    This stunning 3-bedroom, 3-bath home is perfectly situated on a quiet cul-de-sac, offering the ideal blend of modern comfort and thoughtful upgrades, all on a fully fenced 0.90-acre lot. The spacious open floor plan is designed for both entertaining and everyday living, complemented by a gourmet kitchen with stainless steel appliances. The garage includes an added sink for extra convenience, and

    Kara Richetti Real Broker LLC

    141 Shumard Ct, Monticello, FL 32344
  • /27

    $439,000

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

    339 Silver Lake Rd, Monticello, FL 32344

    Beautiful private country setting with large oaks and open pasture! Extra roomy home with open concept kitchen/dining/living and wood burning fireplace. Bring the kids and the horses and chickens. Silver Lake Road is a dead end road which makes this property extra quiet and private. Lots of room to build a barn and/or workshop.

    Pam Kelly Kelly & Kelly Properties, Inc

    339 Silver Lake Rd, Monticello, FL 32344
  • /3

    $469,995 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,940 Sq Ft

    52 Mire Ct, Monticello, FL 32344

    Amazing new construction 3 bedroom 3 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

    52 Mire Ct, Monticello, FL 32344
  • /41

    $460,995 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
  • /19

    $305,000

    • 4 Beds
    • 2 Baths
    • 1,858 Sq Ft

    575 E Palmer Mill Rd, Monticello, FL 32344

    Spacious home located within walking distance of Historic Downtown Monticello. This four bedroom home sits quietly on a manageable half acre lot. Sporting both original hardwood flooring and newly installed LVP flooring, this home blends perfectly for any new home owners. Updated bathrooms and appliances have all been done within the last 5 years. Sizes are approximate.

    Caleb Stephens Waypoint Properties East

    575 E Palmer Mill Rd, Monticello, FL 32344
  • /7

    $119,900

    • Land
    • 5 Acres
    • $23,191 per Acre

    0 Taylor Rd Unit 384618, Monticello, FL 32344

    5.17 acres Taylor Rd. Wonderful Jefferson County location. Minutes from I-10/ Gamble Rd. + downtown Monticello. New 5 lot mini subdivision paved frontage, minimal restrictions to protect values. See survey and site plans in associated docs. Underground County water available. Owner financing available. LAST LOT FOR SALE- SELLER WILL GIVE CLEARING AND SEPTIC ALLOWANCE.

    Kevin Davis The Naumann Group Real Estate

    0 Taylor Rd Unit 384618, Monticello, FL 32344
  • /4

    $89,000

    • Land
    • 4.42 Acres
    • $20,136 per Acre

    TBD Devane, Monticello, FL 32344

    Wooded 4.42 acres, peaceful location just on the outside of Monticello. Across from the Jefferson County Countyr Club.

    Barry Kelly Kelly & Kelly Properties, Inc

    TBD Devane, Monticello, FL 32344
  • /3

    $437,500

    • Land
    • 22 Acres
    • $19,770 per Acre

    00 Boston Hwy, Monticello, FL 32344

    2 MILES FROM Monticello Courthouse! Bordering Jefferson County Country Club. 2 Parcels for total of 22.13 Acres adjacent to Jefferson County Golf Club and bordering Boston Hwy- 1028 ft. frontage - and Mamie Scott Drive. 2 Acres on Mamie Scott with 360' FRONTAGE AND has City Water/Electric Access and is actually within City Limits with zoning of RESIDENTIAL-MULTIFAMILY. Remaining property zoning

    Jennifer Ward Century 21 First Story

    00 Boston Hwy, Monticello, FL 32344
  • /3

    $117,036

    • Land
    • 11 Acres
    • $10,422 per Acre

    Lot 29, Block A E Meadow Rd, Monticello, FL 32344

    11.23 +/- acres at very end of East Meadow Road adjacent to 300+ acres owned by the Suwannee River Water Management District and nearby Aucilla River. Currently being used recreationally as a small hunting retreat by current owner. Additional connecting 9.4 +/- acres also available for purchase from same owner. Why not purchase both parcels and have 20 +/- acres all to yourself. These

    Justin Peel Maclay Realty & Management LLC

    Lot 29, Block A E Meadow Rd, Monticello, FL 32344
  • /3

    $97,964

    • Land
    • 9 Acres
    • $10,422 per Acre

    Lot 30, Block A E Meadow Rd, Monticello, FL 32344

    9.4 +/- acres at very end of East Meadow Road and nearby Aucilla River. Currently being used recreationally as a small hunting retreat by current owner. Additional connecting 11.23 +/- acres also available for purchase from same owner. Why not purchase both parcels and have 20 +/- acres all to yourself. These opportunities don’t come along very often so don’t miss out.

    Justin Peel Maclay Realty & Management LLC

    Lot 30, Block A E Meadow Rd, Monticello, FL 32344
  • /41

    $365,000

    • 2 Beds
    • 1.5 Baths
    • 1,140 Sq Ft

    265 Still Rd, Monticello, FL 32344

    This inviting 2-bedroom, 1.5-bath home sits on 5 peaceful acres between Monticello, FL, and Thomasville, GA, offering a great mix of indoor comfort and outdoor space. It’s just as cute as you want it, with endless potential for outdoor living! Inside, the open great-room layout feels both spacious and cozy, with a large utility room leading to the screened porch and a covered carport that’s

    Catherine Hope All Realty Services

    265 Still Rd, Monticello, FL 32344
  • /10

    $235,000

    • Land
    • 7 Acres
    • $33,571 per Acre

    1400 Gamble Rd, Monticello, FL 32344

    7 beautiful acres just right for your dream home! Power is on the property along with a 105' deep well. Mostly cleared with some pines and hardwoods.

    Kenneth Ayers Primesouth Fezler, Russell and

    1400 Gamble Rd, Monticello, FL 32344
  • /42

    $269,000

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

    2422 N Jefferson St, Monticello, FL 32344

    This beautiful double-wide has been immaculately maintained, with recent updates, including new floors in the kitchen/laundry/guest bath (2014), a new refrigerator (2022), and a new hot water heater (2021). The roof was also replaced in (2014). The living area boasts a space large enough to accommodate separate living and family rooms. The kitchen has a 2nd prep sink in the island with a

    Brenna Kelly-Ward Kelly & Kelly Properties, Inc

    2422 N Jefferson St, Monticello, FL 32344
  • /26

    $499,999

    • Land
    • 45 Acres
    • $11,013 per Acre

    TBD Walker Springs Rd, Monticello, FL 32344

    This 45.4-ACRE PROPERTY is a fantastic opportunity for DEVELOPMENT, FARMING, OR INVESTMENT! With PAVED ROAD FRONTAGE ON WALKER SPRINGS RD, access is easy and convenient. PRIME LOCATION! Just off US HIGHWAY 27, this property provides QUICK ACCESS TO TALLAHASSEE, SCHOOLS, SHOPPING, AND MAJOR ATTRACTIONS like Natural Bridge Battlefield Historic State Park, Cascades Park, and St. Mark’s Lighthouse.

    Moe Mossa Savvy Avenue, LLC

    TBD Walker Springs Rd, Monticello, FL 32344
  • /37

    $419,900

    • 3 Beds
    • 2 Baths
    • 2,766 Sq Ft

    205 N Rhodes St, Monticello, FL 32344

    Classic historical home built in the 1920's. Walking distance to charming downtown Monticello. Large covered front porch for kicking back and relaxing. Wood floors throughout, high ceiling and large open kitchen. This beauty boast over 2700 sf of heated and cooled living space. Beautiful entry into foyer with stairway leading to upstairs landing and two bedrooms. Formal living, formal dining and

    Pam Kelly Kelly & Kelly Properties, Inc

    205 N Rhodes St, Monticello, FL 32344
  • /10

    $625,000

    • Land
    • 40 Acres
    • $15,664 per Acre

    2672 Fulford Rd, Monticello, FL 32344

    Welcome to your slice of paradise on the outskirts of Historic Monticello, Florida! Incredible Live Oak entrance leading to nearly a 40-acre parcel of land is a rare find, perfectly zoned for agricultural use (AG-5), making it an ideal investment for farming, livestock, or recreational activities. The property is adorned with majestic live oak trees, providing shade and creating a picturesque

    Caleb Stephens Waypoint Properties East

    2672 Fulford Rd, Monticello, FL 32344
  • /41

    $399,000

    • 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
  • /40

    $1,390,000

    • 4 Beds
    • 6 Baths
    • 9,848 Sq Ft

    193 Nautilus Dr, Monticello, FL 32344

    Introducing a breathtaking fusion of modern convenience and medieval charm nestled in the heart of the woods. This meticulouslyrenovated 9,848 square foot architectural marvel boasts a captivating design, featuring uniquely sized windows and curving wallsthat exude artistic allure at every turn. Step inside and experience the epitome of luxury living. The main building offers a seamlessblend of

    Ondrea Maldonado Hamilton Realty Advisors LLC

    193 Nautilus Dr, Monticello, FL 32344
  • /31

    $51,900

    • Land
    • 3.46 Acres
    • $15,000 per Acre

    0 Malloy Landing Rd, Monticello, FL 32344

    This 3.46-ACRE PROPERTY is perfect for INVESTMENT, DEVELOPMENT, OR A PRIVATE RETREAT! Located at Maloy Landing Rd & E Pinhook Rd in Monticello, FL (Jefferson County), this land is ZONED AGRICUL TURAL (AG). With 100 FEET OF PAVED ROAD FRONTAGE and sitting at 91.6 FEET ELEVATION, this property offers FLEXIBILITY & NO HOA RESTRICTIONS! UTILITIES & ACCESSIBILITY! ELECTRICITY IS NEARBY BUT NOT YET

    Moe Mossa Savvy Avenue, LLC

    0 Malloy Landing Rd, Monticello, FL 32344
  • /19

    $135,000

    • Land
    • 10 Acres
    • $13,500 per Acre

    00002 Walker Springs Rd, Monticello, FL 32344

    OVER 10 ACRES OF BEAUTIFUL, BUILDABLE LAND IN JEFFERSON COUNTY! Just a SHORT DRIVE FROM TALLAHASSEE, this property is perfect for a PRIVATE RETREAT, HOMESTEAD, OR INVESTMENT! With PAVED ROAD FRONTAGE ON CHANCEY RD, access is easy and convenient! BUILD YOUR DREAM HOME! This AGRICUL TURAL-ZONED PROPERTY allows for a SINGLE-FAMILY HOME with NO HOA RESTRICTIONS, giving you the freedom to BRING YOUR

    Moe Mossa Savvy Avenue, LLC

    00002 Walker Springs Rd, Monticello, FL 32344
  • /26

    $854,280

    • Land
    • 95 Acres
    • $9,000 per Acre

    00001 Walker Springs Rd, Monticello, FL 32344

    This beautiful 94.92-ACRE PROPERTY in Monticello, FL offers incredible opportunities for investment, homesteading, or recreation! With PAVED ROAD FRONTAGE on E. Pinhook Rd, Tin Top Rd, and Walker Springs Rd, accessibility is a major plus! The land consists of 75 ACRES OF UPLAND and 20 ACRES OF LOWLAND, featuring PLANTED TIMBER (8-9 YEARS OLD)—a fantastic investment with potential harvesting in

    Moe Mossa Savvy Avenue, LLC

    00001 Walker Springs Rd, Monticello, FL 32344

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