Chipley, FL Homes for Sale under $500,000

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  /34

  $274,999

  $5K PRICE DROP

  • 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

  $229,900

  $20K 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
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  /77

  $449,900

  $10K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,002 Sq Ft

  2547 Nightfall Place, Chipley, FL 32428

  *** OPEN HOUSE August 30th*** Welcome to 2547 Nightfall Place! Step inside this charming rustic cabin-style home with modern finishes situated on 4.52 acres of unrestricted land.Offering 4 bedrooms, 3 full bathrooms with a split bedroom floorplan nestled in a quiet country setting providing a perfect opportunity for avid homesteaders looking for a private retreat!Entering you will

  Adam Drysdale St Andrew Shores Realty Serv

  2547 Nightfall Place, Chipley, FL 32428
• 

  $259,990

  New Construction

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

  1710 Vicki Ct, Chipley, FL 32428

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

  1710 Vicki Ct, 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
• 

  

  /23

  $224,900

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft

  2774 Rolling Pines Rd, Chipley, FL 32428

  This 2 bedroom, 2bath 1 story home located on 1.9 acres with approximately 241' on Hwy 77 Is move in ready. Zoned single family but, seller says it can be split. Large outbuilding, several other sheds, brand new stainless electric stove & refrigerator. Split bedroom plan.

  Trudy VanHorn Berkshire Hathaway HomeServices Beach Properties of Florida

  2774 Rolling Pines Rd, Chipley, FL 32428
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  /27

  $209,000

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

  3918 Bricknell Ave, Chipley, FL 32428

  Back on the market! NO FAULT TO SELLER. 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

  Carly Harless Beachy Beach Real Estate

  3918 Bricknell Ave, Chipley, FL 32428
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  /27

  $282,653

  New Construction $11K PRICE DROP

  • 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
• 

  $262,990

  New Construction

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

  4301 Country Club Blvd, Chipley, FL 32428

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

  4301 Country Club Blvd, Chipley, FL 32428
• 

  

  /27

  $350,000

  $125K PRICE DROP

  • 2,682 Sq Ft

  5163 Florida 77, Chipley, FL 32428

  This commercial property beside the booming subdivision of Sunny Hills is ready for your business. It is located on Hwy 77 and about 30 minutes to Panama City and about 40 minutes to the World's Most Beautiful Beaches of Panama City Beach. The property includes a 9x6 walk-in cooler, four deep freezers, two standup refrigerators, one standup freezer, two standup coolers, deep chest, two sliding

  Harvey Webb Counts Real Estate Group

  5163 Florida 77, Chipley, FL 32428
• 

  

  /51

  $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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  /61

  $319,900

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  3726 Pine Log Rd, Chipley, FL 32428

  Escape to the country and enjoy the peace, privacy and open space that surrounds this home and the 5 acres of land it sits on. This home is perfect for those looking for a quiet rural lifestyle with plenty of room to spread out. The back porch is perfect for entertaining or just enjoying your morning coffee. There is a workshop and two pole barns that have more than enough room for storage. There

  Jessica Wilson Northwest Florida Realty, LLC

  3726 Pine Log Rd, Chipley, FL 32428
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  /25

  $250,400

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,458 Sq Ft

  4069 Ramus Dr, Chipley, FL 32428

  Welcome to 4066 Ramus 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 Freeport 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

  4069 Ramus Dr, Chipley, FL 32428
• 

  

  /54

  $375,000

  $20K PRICE DROP

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

  434 Tinker Ln, Chipley, FL 32428

  Pristine Home away from it all! Tucked away on 3.66 peaceful acres with very few neighbors, this newer, upgraded home offers the perfect blend of privacy, comfort, and functionality. Enjoy quiet country living with your own pond, wide open space, and room to breathe.This property is turn key!Inside, you'll find a beautifully finished kitchen with upgraded touches and a large pantry, ideal

  Leigh Clark Elite Realty

  434 Tinker Ln, Chipley, FL 32428
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  /49

  $350,000

  $25K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,763 Sq Ft

  1561 Snell Rd, Chipley, FL 32428

  Southern Charm on 1.83+/- Acres! Nestled beneath mature shade trees and surrounded by peaceful country scenery, this 3-bedroom, 2.5-bath home offers a timeless design, spacious living areas, and room to enjoy both inside and out. Step inside to find a welcoming floor plan featuring a formal dining room, a dedicated library, and a cozy breakfast area adjoining the kitchen. The spacious living room

  Seamus O'neill SOUTHERN WAY REALTY, INC.

  1561 Snell Rd, Chipley, FL 32428
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  /21

  $349,000

  $50K PRICE DROP

  • Land
  • 38.6 Acres
  • $9,041 per Acre

  783/767 Highway 90, Chipley, FL 32428

  Looking for your own outdoorsman's paradise? This 38± acre property just minutes from downtown Chipley offers a rare opportunity to create a private retreat built around hunting, fishing, wildlife, and the freedom of country living.Imagine building your home or cabin surrounded by woods, stepping outside to hunt your own land, spending the afternoon fishing the property's large

  Tyler Smith Legacy Premier Agency

  783/767 Highway 90, Chipley, FL 32428
• 

  $245,990

  New Construction

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

  2216 Acorn Place, 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

  2216 Acorn Place, Chipley, FL 32428
• 

  

  /45

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,852 Sq Ft

  4122 Highland Ave, Chipley, FL 32428

  Welcome to this well-maintained home located in the desirable Sunny Hills community, offering comfort, functionality, and convenience. Situated on a 0.229-acre lot, this property provides a peaceful setting while still being within a reasonable drive to the beautiful white-sand beaches of Northwest Florida. One of the standout features of this property is the private well system, complete with a

  Cindy Birge Elite Realty

  4122 Highland Ave, Chipley, FL 32428
• 

  

  /50

  $485,000

  • 4 Beds
  • 3 Baths
  • 3,756 Sq Ft

  620 4th St, Chipley, FL 32428

  Space, versatility, and an incredible outdoor setup come together in this impressive home! Offering approximately 3,700+ square feet of living space, this home provides an abundance of room with a layout that easily adapts to everyday living, entertaining, working from home, and more. Tucked away at the quiet end of a dead-end street, the home enjoys a peaceful setting away from through

  Seamus O'neill SOUTHERN WAY REALTY, INC.

  620 4th St, Chipley, FL 32428
• 

  

  /54

  $450,000

  • 4 Beds
  • 3.5 Baths
  • 3,745 Sq Ft

  700 2nd St, Chipley, FL 32428

  Discover the timeless charm of this classic home, nestled in the historic district of Chipley. Meticulously renovated and updated throughout, this residence blends historic character with modern luxury, offering an exceptional living experience marked by impeccable attention to detail and thoughtful craftsmanship. Boasting four spacious bedrooms and four bathrooms (three full and one half), the

  Justin Raley Think Real Estate

  700 2nd St, Chipley, FL 32428
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  /29

  $350,000

  $65K PRICE DROP

  • 1,557 Sq Ft

  1153 Main St, Chipley, FL 32428

  Positioned in a commercial zoning district with an average daily traffic count of 14,500 (2023 DOT Data), this versatile brick property offers exceptional potential for business, investment, or mixed-use occupancy. Currently configured as a 3-bedroom, 1.5-bath home with a full kitchen, the layout easily adapts to a variety of commercial uses including professional office, retail, medical, salon,

  Matthew Wright Think Real Estate

  1153 Main St, Chipley, FL 32428
• 

  

  /3

  $221,000

  • Land
  • 19.2 Acres
  • $11,510 per Acre

  000 Gilberts Mill Rd, Chipley, FL 32428

  Take advantage of this exceptional 19.2-acre residential tract in Chipley, Florida. With a beautiful natural setting, plenty of open space, and room to create your own private retreat, this property offers a variety of possibilities for a custom home, or family homestead. Enjoy the peace and privacy of country living while remaining conveniently located near Chipley's local amenities, shopping,

  Eddie Tarter Counts Real Estate Group Inc

  000 Gilberts Mill Rd, Chipley, FL 32428
• 

  

  /31

  $259,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  1214 Johnson Ave, Chipley, FL 32428

  Don't let the age of this home fool you--this beautifully renovated property is move-in ready and filled with modern updates! Situated on over an acre within the Chipley city limits, this 3-bedroom, 2-bath home offers a spacious and functional layout, along with a versatile bonus room that could serve as a fourth bedroom, home office, playroom, or additional den. Major improvements include a new

  Cindy Birge Elite Realty

  1214 Johnson Ave, Chipley, FL 32428
• 

  

  /46

  $335,000

  $65K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,529 Sq Ft

  1730 Firetower Rd, Chipley, FL 32428

  Seller offering $5,000 in Closing Costs assistance and Fidelity National Home Warranty. Escape to peace and quiet with this versatile 3-bedroom, 2-bathroom solid block home situated on over 7.3 acres of beautiful land. Offering 1,529 square feet of living space, this charming retreat features laminate and tile flooring, a functional kitchen complete with a breakfast bar and gas range, and a

  Eren Sullivan Counts Real Estate Group

  1730 Firetower Rd, Chipley, FL 32428
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  /45

  $349,000

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 432 Sq Ft

  5491 Highway 77, Chipley, FL 32428

  Reduced!! Many opportunities available for this 4.75 acre parcel with on 430 feet of Highway 77 frontage. The property has a number of improvements on it. The main structure is a 1200 square foot, 40x30 metal building that has a 10 by 8 shed converted to a half bathroom behind it that was used as a store.. There is also a 432 square foot building used as an efficiency that has a loft. Three other

  Victor Jed CENTURY 21 Commander Realty

  5491 Highway 77, Chipley, FL 32428
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  /5

  $429,000

  New Construction $51K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,577 Sq Ft

  2883 Paradise Lakes Rd, Chipley, FL 32428

  New Construction single family home spacious 2299 square feet on just about a 1/2 acre of land with some water views of Dunsford Lake The home is located in a gated community with private boat ramp. This home has tiled baths with glass shower enclosures vanities with Quartz counter tops the kitchen will have self closing wood cabinets and quartz counter tops. Flooring is water proof laminate

  Victor Carnero Blue Skies Real Estate

  2883 Paradise Lakes Rd, Chipley, FL 32428
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  /39

  $285,000

  $14K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,939 Sq Ft

  2199 Sunny Hills Blvd, Chipley, FL 32428

  Welcome to this spacious and beautifully maintained home, nestled in the peaceful community of Sunny Hills. Featuring an open-concept layout, this home offers a seamless flow between the kitchen, dining, and living areas, perfect for both everyday living and entertaining.The kitchen is designed to impress with granite countertops, abundant cabinet storage, newer appliances, a breakfast

  Paul Gibney Corcoran Reverie

  2199 Sunny Hills Blvd, Chipley, FL 32428
• 

  

  /32

  $371,400

  New Construction

  • 5 Beds
  • 3 Baths
  • 2,516 Sq Ft

  4059 Falcon Dr, Chipley, FL 32428

  Welcome to 4059 Falcon Drive at Sunny Hills in Freeport, Florida. This pre-construction homesite is situated in a cul-de-sac and offers the opportunity to secure new construction prior to groundbreaking. This property will be developed with the Sawyer floorplan and estimated completion timelines and build details available upon request.The Sawyer features five bedrooms and three full

  4059 Falcon Dr, Chipley, FL 32428
• 

  $258,990

  New Construction

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

  1714 Dora Ln, Chipley, FL 32428

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

  1714 Dora Ln, Chipley, FL 32428
• 

  

  /27

  $289,900

  New Construction $4K PRICE DROP

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

  4010 Linwood Dr, Chipley, FL 32428

  Welcome to 4010 Linwood Drive 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

  4010 Linwood Dr, Chipley, FL 32428
• 

  

  /19

  $276,900

  New Construction $27K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,279 Sq Ft

  3900 Bricknell Ave, 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

  3900 Bricknell Ave, Chipley, FL 32428

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