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Chipley, FL Homes for Sale under $500,000

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  • /19

    $279,900

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    2148 Jensen Place, Chipley, FL 32428

    Welcome to this beautiful 3-bedroom, 2-bathroom Craftsman style home built in 2023, offering the perfect blend of modern design, quality construction, and small-town charm in the growing Sunny Hills community. Situated on a spacious 0.30 acre lot, this move-in-ready home features an open concept floor plan designed for both everyday living and entertaining. Step inside to discover modern finishes

    Cari Henry CENTURY 21 Commander Realty

    2148 Jensen Place, Chipley, FL 32428
  • /28

    $349,000

    $50K PRICE DROP
    • Land
    • 38.6 Acres
    • $9,041 per Acre

    767 & 783 Highway 90, Chipley, FL 32428

    Description: 1 4 13 1.4 ORB 1168 P 451 PRCL DESC IN ORB 1168 P 451Remarks: Stretching across 38± acres just minutes from downtown Chipley, this property tells the story of a dream that's ready for its next chapter. Two parcels, two access points directly off Hwy 90, and a landscape loaded with infrastructure and natural character waiting to be brought back to life. The front half of the

    Tyler Smith Legacy Premier Agency LLC

    767 & 783 Highway 90, Chipley, FL 32428
  • /15

    $285,900

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,598 Sq Ft

    2359 Rockford Dr, Chipley, FL 32428

    Hello, are you looking for some luxury in your life? Because in this gorgeous home located in desirable Sunny Hills Unit 1, you're going to find it! Beautiful new construction by a builder who knows that, besides high-quality construction, finishing touches matter. Nine-foot ceilings and plenty of windows to let in lots of natural light. Gorgeous stainless appliances, quartz countertops, kitchen

    Kristi Basinger RIGHT NOW! Real Estate

    2359 Rockford Dr, Chipley, FL 32428
  • /36

    $360,000

    $15K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,823 Sq Ft

    3995 Quail Ave, Chipley, FL 32428

    Located in the established Sunny Hills community, this well-maintained 4-bedroom, 2-bath home offers plenty of space and privacy. The open-concept floor plan creates an easy flow between the living, dining, and kitchen areas, while the fireplace adds warmth and character to the main living space. The fourth bedroom provides the perfect space for a home office, playroom, guest room, or growing

    Kelly Lathem Corcoran Reverie

    3995 Quail Ave, Chipley, FL 32428
  • /50

    $235,000

    • 4 Beds
    • 2 Baths
    • 2,052 Sq Ft

    1060 Florida 277, Chipley, FL 32428

    Located in a desirable area with convenience to all medical and shopping. The home sits on over 3 acres completely fenced, with electric gate. The home is over 2000 sq ft. It features 2 living spaces with a fireplace with electric logs in one of them. If your family needs space don't miss seeing this home. The kitchen has lots of cabinets with an island, Off the utility is a walk in pantry. Split

    Linda Cumbaa Elite Realty

    1060 Florida 277, Chipley, FL 32428
  • /30

    $229,997

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft

    4181 Luar, Chipley, FL 32428

    Welcome to Your Sunny Hills Dream Home! ~*~CORNER LOT!!~*~Brand-new construction, pristine design, and ultimate peace of mind! Located in the highly desirable Sunny Hills community, this beautifully crafted 3-bedroom, 2-bathroom home offers over 1,200 sq. ft. of modern comfort and style. Step inside to a bright, open-concept layout elevated by 9' ceilings and a soaring vaulted living area,

    John Cunningham Realty Destination LLC

    4181 Luar, Chipley, FL 32428
  • /21

    $299,900

    New Construction $4K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,760 Sq Ft

    3892 Bricknell Ave, Chipley, FL 32428

    Take a step inside The Garnet, a 3-bedroom, 2-bath, 2-car garage model available exclusively in Sunny Hills. This beautiful home boasts a large, open concept living area perfect for entertaining. Long day? Step outside the dining room into quiet, peaceful solitude and enjoy a nightcap on your covered back porch. The spacious master suite and large walk-in closet is sure to win your heart -

    Sara Iaropoli Deltona Marketing at Sunny Hills Inc

    3892 Bricknell Ave, Chipley, FL 32428
  • /25

    $343,000

    • Land
    • 80 Acres
    • $4,288 per Acre

    000 Oswald Gilbert Dr, Chipley, FL 32428

    Explore the potential of this expansive 80-acre property located on Oswald Road. Previously utilized as a municipal sprayfield and originally used for agricultural purposes, this tract offers a unique blend of infrastructure and acreage for a variety of possible future uses. The site currently contains in-ground distribution piping, with approximately 80-100 2'' riser pipes extending 4-5 feet

    Cindy Birge Elite Realty

    000 Oswald Gilbert Dr, Chipley, FL 32428
  • /56

    $436,000

    $14K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,038 Sq Ft

    3836A Belmar Place, Chipley, FL 32428

    ASSUMABLE at 6.1% (bal. under $401k), this 7.52 acres of peaceful tranquility and woodsy privacy is nestled in the heart of Sunny Hills. Two-story home features 3 bedrooms and 2 1/2 baths, plus BONUS room which can be your 4th bedroom, den or office. This home is wonderful and cozy with it's upstairs balcony looking out over a beautiful yard and pond, especially for some gorgeous evening sunsets,

    Kristi Basinger RIGHT NOW! Real Estate

    3836A Belmar Place, Chipley, FL 32428
  • /4

    $299,900

    New Construction $20K PRICE INCREASE
    • 4 Beds
    • 2 Baths
    • 1,801 Sq Ft

    TBD Elkcam Blvd Unit Lot 49, Chipley, FL 32428

    **TO BE BUILT** New construction in Sunny Hills with upgrades included as standard. 1,801 sqft open floor plan, 9' ceilings, LVP flooring, and modern finishes. Kitchen features quartz countertops, white shaker cabinets, subway tile backsplash, GE appliances, and farmhouse sink. Spacious primary suite with walk-in closet and dual vanities + private bath. Separate laundry room. The community of

    Abbott Martin Group EXP Realty LLC

    TBD Elkcam Blvd Unit Lot 49, Chipley, FL 32428
  • /33

    $225,000

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    783 West Blvd, Chipley, FL 32428

    Charming and exceptionally well-maintained 3-bedroom, 2-bath brick and vinyl home situated on a beautiful 1-acre lot within the city limits of Chipley, Florida. This move-in-ready property features a cozy kitchen with a large eat-at bar, recessed lighting, and an inviting floor plan designed for comfortable living. Step outside to enjoy the spacious patio deck and fire pit, perfect for

    Bettie Slay Bettie's Country Realty

    783 West Blvd, Chipley, FL 32428
  • /19

    $273,800

    New Construction $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,279 Sq Ft

    2272 Rockford Cir, Chipley, FL 32428

    Take a step inside The Emerald, a 3-bedroom, 2-bath, 2-car garage model available exclusively in Sunny Hills. This beautiful home boasts a large, open concept living area perfect for entertaining. The spacious master suite and walk-in closet is sure to win your heart. The attached master bath allows for your privacy, keeping your space separate from the shared spaces of the home. Roomy secondary

    Sara Iaropoli Deltona Marketing at Sunny Hills Inc

    2272 Rockford Cir, Chipley, FL 32428
  • /58

    $449,900

    $100K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 3,024 Sq Ft

    1294 Dragonfly Ln, Chipley, FL 32428

    Mother-in-law suite special! This 6 bedroom, 4 bathroom house features a connected 2 bedroom suite with large living room, modern bathroom suite with granite counter tops, a tile walk-in shower, and an office for a total of approximately 1,200 square feet. A door separates the mother-in-law suite from the rest of the 2-story home that just had a major makeover that includes new windows, concrete

    Harvey Webb Counts Real Estate Group

    1294 Dragonfly Ln, Chipley, FL 32428
  • /46

    $414,999

    $5K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,860 Sq Ft

    1012 Carlisle Rd, Chipley, FL 32428

    Welcome home to peaceful country living on approximately 2+/- acres, offering the perfect blend of privacy and convenience just minutes from town. This spacious 4 bedroom, 2.5 bath brick home offers a blend of charm, comfort, and room to spread out both inside and out. From the moment you arrive, the circular driveway, mature landscaping, and inviting front entry create a welcoming first

    Seamus O'neill SOUTHERN WAY REALTY, INC.

    1012 Carlisle Rd, Chipley, FL 32428
  • /2

    $255,990

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,773 Sq Ft

    ROANOKE Plan, Chipley, FL 32428

    4 bed | 2 Bath | 2-Bay | 1,773 Sq. Ft.

    2187 Sunny Hills Blvd Unit 41176278, Chipley, FL 32428
  • /15

    $459,900

    • 4 Beds
    • 3 Baths
    • 2,348 Sq Ft

    661 Highway 90, Chipley, FL 32428

    Discover the perfect blend of modern comfort and peaceful country living in this beautifully maintained 4-bedroom, 3-bath home offering 2,348 sq ft of living space on 2.31 mostly cleared acres. Built in 2016, this home features an open floor plan, stainless steel appliances, soft-close cabinets, and a spacious primary suite with two walk-in closets. Enjoy relaxing mornings on the covered front

    Steven Koleno Beycome of Florida LLC

    661 Highway 90, Chipley, FL 32428
  • /58

    $278,000

    • 3 Beds
    • 2 Baths
    • 1,377 Sq Ft

    3425 Quail Ridge Dr, Chipley, FL 32428

    Welcome to your lakefront retreat! This 3BR/2BA home sits on a beautifully wooded 1.01-acre lot and offers direct access for swimming, fishing, and non-motorized boating. The interior features LVP flooring, Corian kitchen countertops, and a fully equipped kitchen. Enjoy the screen-enclosed sunroom, perfect for morning coffee or watching sunsets over the lake. Major upgrades include a newer HVAC

    Meghan Hall Keller Williams Realty SRB

    3425 Quail Ridge Dr, Chipley, FL 32428
  • /27

    $345,000

    $40K PRICE DROP
    • Land
    • 3 Acres
    • $115,000 per Acre

    3831 Florida 77, Chipley, FL 32428

    This is a wonderful opportunity to own 3 acres on a very busy road just outside of Wausau Fl. on HWY 77 Endless possibilities with this property that has income producing properties already , has a 3 bay garage and a 1 bedroom house that has been completely remolded. Let it pay for itself or remove the buildings and start new. With the new four lane highway being finished up ,makes this a great

    Wanda Raney 850 Sunshine Realty

    3831 Florida 77, Chipley, FL 32428
  • /38

    $218,000

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

    1804 Ulmer Ln, Chipley, FL 32428

    Welcome to this spacious 3-bedroom, 2-bath home located in the desirable Sunny Hills community! The property is located on three lots totaling over half an acre-including a desirable corner lot. This home also features a versatile bonus room with windows and a closet, perfect for a Florida room, home office, or potential fourth bedroom. A separate oversized laundry room provides additional

    Caitlin Domer CENTURY 21 Commander Realty

    1804 Ulmer Ln, Chipley, FL 32428
  • /29

    $249,900

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    4597 Spotted Horse Ln, Chipley, FL 32428

    Looking for country living with all the hard work already done? This beautiful 3.94-acre property is move-in ready and packed with upgrades! The property features a like-new 2024 Southern Energy 14x60 manufactured home offering 2 bedrooms and 2 bathrooms. In addition, you'll find a new well, new underground power, and a septic system sized for a future 3-bedroom, 3-bath home--giving you room to

    Stan Fowler Think Real Estate

    4597 Spotted Horse Ln, Chipley, FL 32428
  • /50

    $359,900

    $30K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,624 Sq Ft

    3243 Quail Ridge Dr, Chipley, FL 32428

    *SELLER OFFERING $5,000 CONCESSIONS*Use it for rate buy down, aesthetic changes or down payment help.This move in ready home on 3 acres in the gated community of Leisure Lakes offers plenty of space inside and out. Situated with direct waterfront on Lake Suzanne, this cottage style home has over 1,600 sf of living space including 4 bedrooms and 2 bathrooms. 1 of the bedrooms can only be

    Tiffany Baker Hennessy Real Estate Group LLC

    3243 Quail Ridge Dr, Chipley, FL 32428
  • /89

    $439,900

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,938 Sq Ft

    1712 Shamrock Ln, Chipley, FL 32428

    Seller is offering a home warranty with an acceptable offer for added buyer peace of mind! Located in the desirable Orange Hill area just a few miles from town, this well-maintained brick home sits on acreage and offers updated windows, crown molding throughout, tile and luxury vinyl plank flooring, landscaped flower beds, fruit trees, and plenty of outdoor space to enjoy. A circular drive

    Denise Myers Elite Realty

    1712 Shamrock Ln, Chipley, FL 32428
  • /22

    $330,000

    $29K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft

    3047 Everest Dr, Chipley, FL 32428

    Motivated seller, Move-in ready and recent updates, this 3-bedroom, 2-bath home is nestled on 11 private acres at the end of a dead-end road in a gated community, offering the perfect blend of privacy and convenience. Ideally located between two lakes, this property is perfect for those who enjoy fishing, boating, and the outdoors. The home features a functional floor plan, comfortable living

    Amanda Creamer World Impact Real Estate

    3047 Everest Dr, Chipley, FL 32428
  • /50

    $224,999

    New Construction $7K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,294 Sq Ft

    2295 Rockford Cir, Chipley, FL 32428

    Located in desirable Sunny Hills Unit 1, this luxury floor plan 3-bed, 2-bath home in is ''brand new'' shape. Seller did not ended up living in this home and has not used the appliances. He's added a fence to the entire back yard and stained it for additional protection against WDOs (Fence is complete, tho not all pics have been updated). One feature of this beautiful home you'll notice right

    Kristi Basinger RIGHT NOW! Real Estate

    2295 Rockford Cir, Chipley, FL 32428
  • /37

    $274,999

    $5K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,768 Sq Ft

    872 1st St, Chipley, FL 32428

    Welcome to this charming home situated on four city lots, where classic Southern style blends seamlessly with thoughtful updates throughout this 4-bedroom, 2-bath property. From the moment you arrive, you'll appreciate the inviting curb appeal and the comfortable feel this home offers. Inside, the living room provides a spacious setting for everyday living and entertaining, featuring vinyl plank

    Seamus O'neill SOUTHERN WAY REALTY, INC.

    872 1st St, Chipley, FL 32428
  • /40

    $439,000

    • 3 Beds
    • 2.5 Baths
    • 2,525 Sq Ft

    1453 Highway 277, Chipley, FL 32428

    Looking for acreage, a workshop, and room to spread out? This 7 acre property with Hwy 277 frontage offers the flexibility and space many buyers are searching for. The brick home features a metal roof, covered front and back porches, fresh interior paint, updated flooring, and a primary bedroom on the main level. The oversized RV barn with attached workshop, lean to storage, fenced area, and

    Sheila Barbee Barbee Realty Inc

    1453 Highway 277, Chipley, FL 32428
  • /34

    $279,999

    • 3 Beds
    • 2 Baths
    • 1,502 Sq Ft

    1975 Ambassador Ct, Chipley, FL 32428

    Welcome home to this beautifully designed 3-bedroom, 2-bath residence offering the perfect blend of modern finishes, functional living spaces, and the quiet lifestyle Sunny Hills is known for. This thoughtfully designed home is filled with natural light and offers an open-concept layout that's perfect for both everyday living and entertaining. The spacious kitchen is the heart of the home,

    Seamus O'neill SOUTHERN WAY REALTY, INC.

    1975 Ambassador Ct, Chipley, FL 32428
  • /47

    $449,900

    • 4 Beds
    • 2 Baths
    • 2,128 Sq Ft

    1336 Orange Hill Rd, Chipley, FL 32428

    Don't let the age fool you on this beautiful, updated country 4/2 home that sits minutes from town. Offering a nice kitchen, dining area with gas fireplace, living room, spacious private master bedroom with access to covered patio, master bath with laundry, 3 additional bedrooms and a oversized hall bathroom with a walk in shower. There is a fenced in newer 14 x 20 salt water inground pool, 32x60

    Wanda Owens SOUTHERN WAY REALTY, INC.

    1336 Orange Hill Rd, Chipley, FL 32428
  • /40

    $237,000

    $13K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    2442 Pinewood Dr, Chipley, FL 32428

    Giddy up--or slow down--3.45 acres of freedom just hit the market.Whether you're dreaming of farm-to-table living, craving room to breathe, seeking a private retreat, or simply looking for a quieter pace of life, this unique property offers the space and flexibility to make it your own.Located in the sought-after community of Grassy Pond Ranches, this beautifully maintained 3-bedroom,

    Jessica Albritton Beachy Beach Real Estate

    2442 Pinewood Dr, Chipley, FL 32428
  • /39

    $289,000

    $31K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,296 Sq Ft

    1019 Hughes Rd, Chipley, FL 32428

    Country Living Near Falling Waters State Park! Welcome to your own slice of Northwest Florida paradise, where peaceful country living meets modern comfort and convenience. Situated on a beautiful 1-acre +/- homesite just a half mile from the renowned Falling Waters State Park, this completely updated home offers the perfect blend of charm, functionality, and outdoor enjoyment. Inside, you'll find

    Gina Williams Chipola Realty, Chipley Office

    1019 Hughes Rd, Chipley, FL 32428
  • /35

    $254,900

    New Construction $15K PRICE INCREASE
    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    TBD Florence Ct Unit Lot 14, Chipley, FL 32428

    **UNDER CONSTRUCTION - TO BE BUILT** New construction in Sunny Hills with upgrades included as standard. 1,300 sqft open floor plan, 9' ceilings, LVP flooring, and modern finishes. Kitchen features quartz countertops, white shaker cabinets, subway tile backsplash, GE appliances, and farmhouse sink. Spacious primary suite with dual vanities + private bath. Separate laundry room. Enjoy lakes, boat

    Abbott Martin Group EXP Realty LLC

    TBD Florence Ct Unit Lot 14, Chipley, FL 32428
  • 1857 Sunny Hills Blvd, Chipley, FL 32428

    $251,990

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,684 Sq Ft

    1857 Sunny Hills Blvd, Chipley, FL 32428

    4 bed | 2 bath | 2-bay | 1684 sqft *Closing costs are additional and not included in the USDA 30 year fixed rate 100% financing. Terms and availability of this loan program, and the sales price, are examples only and are subject to change without notice. Loans are subject to credit approval. Restrictions and conditions may apply. USDA loans are subject to income and geographic eligibility

    1857 Sunny Hills Blvd, Chipley, FL 32428
  • /33

    $219,997

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft

    4183 Luar, Chipley, FL 32428

    Welcome to Your Sunny Hills Dream Home!Brand-new construction, pristine design, and ultimate peace of mind! Located in the highly desirable Sunny Hills community, this beautifully crafted 3-bedroom, 2-bathroom home offers over 1,200 sq. ft. of modern comfort and style. Step inside to a bright, open-concept layout elevated by 9' ceilings and a soaring vaulted living area, creating an

    John Cunningham Realty Destination LLC

    4183 Luar, Chipley, FL 32428
  • /51

    $219,900

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    1764 Clayton Rd, Chipley, FL 32428

    Located in a desirable area with convenient access to town, this property includes two adjoining one-acre parcels (separate parcel IDs), and both parcels have been surveyed. The home sits on one fully grassed acre; the additional acre also features established grass and has been mostly cleared, with only a few trees remaining in the back west corner. The property is accessed through an electric

    Denise Myers Elite Realty

    1764 Clayton Rd, Chipley, FL 32428
  • /47

    $279,900

    $41K PRICE DROP
    • Land
    • 22 Acres
    • $12,723 per Acre

    107 Pike Pond Rd, Chipley, FL 32428

    Bring your building plans or mobile home this is an opportunity you don't want to miss! This versatile property is ready for your vision with a pole barn, RV electrical hookups, a 280-ft well, and an existing septic system already in place. Overlooking a beautiful 40-acre spring-fed pond, you'll enjoy peaceful views and abundant wildlife, including deer, turkey, ducks, bass, catfish, and

    Jewl Bagley Southern Choice Properties Llc

    107 Pike Pond Rd, Chipley, FL 32428
  • /25

    $273,900

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,799 Sq Ft

    1663 Salem Dr, Chipley, FL 32428

    Welcome to 1663 Salem Drive at Sunny Hills in Chipley, Florida. This pre-construction homesite offers the opportunity to secure new construction prior to groundbreaking. This property will be developed with the Cali floorplan and built to current design standards and specifications. Buyers may have the ability to personalize select finishes depending on the stage of construction. Estimated

    1663 Salem Dr, Chipley, FL 32428
  • /10

    $253,990

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,684 Sq Ft

    1847 Sunny Hills Blvd, Chipley, FL 32428

    4 bed | 2 bath | 2-bay | 1684 sqft *Closing costs are additional and not included in the USDA 30 year fixed rate 100% financing. Terms and availability of this loan program, and the sales price, are examples only and are subject to change without notice. Loans are subject to credit approval. Restrictions and conditions may apply. USDA loans are subject to income and geographic eligibility

    1847 Sunny Hills Blvd, Chipley, FL 32428
  • /27

    $209,000

    • 3 Beds
    • 2 Baths
    • 1,259 Sq Ft

    3918 Bricknell Ave, Chipley, FL 32428

    This 3 bedroom, 2 bathroom brick home offers a comfortable layout with plenty of space to make your own. The home features a welcoming living area, generously sized bedrooms, master bedroom includes a private bath along with a walk-in closet and a bright Florida-room that provides additional space perfect for relaxing, entertaining, a home office, or a playroom. On the opposite side of the

    Carly Harless Beachy Beach Real Estate

    3918 Bricknell Ave, Chipley, FL 32428
  • /27

    $293,900

    New Construction
    • 5 Beds
    • 3 Baths
    • 2,043 Sq Ft

    1994 Ambassador Ct, Chipley, FL 32428

    Welcome to 1994 Ambassador Court at Sunny Hills in Chipley, Florida. This pre-construction homesite offers the opportunity to secure new construction prior to groundbreaking. This is a corner lot that will be developed with the Lakeside floorplan and built to current design standards and specifications. Buyers may have the ability to personalize select finishes depending on the stage of

    1994 Ambassador Ct, Chipley, FL 32428
  • /4

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,918 Sq Ft

    1130 Timberlane Rd, Chipley, FL 32428

    Convenience to all the amenities to town while still enjoying the quiet seclusion of the country.close to florida falls state park .5 minutes to walmart and interstate 10 That's exactly what you get with this 3 bedroom 2 bath brick home on 2.2 acres. The house is 1,918 Sq. Ft. heated and cooled. A little over 2500 total. There have been multiple updates to the home. Must see to appreciate. The

    INVESTMENT REALTY Beach Realty of Florida

    1130 Timberlane Rd, Chipley, FL 32428

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