Chipley, FL Homes for Sale under $500,000

• 

  

  

  /20

  $278,848

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,728 Sq Ft

  2212 Chase St, Chipley, FL 32428

  Seize the opportunity to own the Lavender model by Homes by Deltona--beautifully situated in the tranquil community of Sunny Hills. This four-bedroom, two-bathroom gem is not just a house, but a showcase of standard features. As you step inside, you're greeted by a spacious open concept living area, crowned with a vaulted ceiling that elevates the home's aesthetic. The kitchen, designed to

  Sara Iaropoli Deltona Marketing at Sunny Hills Inc

  2212 Chase St, Chipley, FL 32428
• 

  $228,990

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft

  3571 Westbrook Dr, Chipley, FL 32428

  3 bed | 2 bath | 2-bay | 1416 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

  3571 Westbrook Dr, Chipley, FL 32428
• 

  

  

  /30

  $260,000

  $8K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,337 Sq Ft

  4533 Hancock Ct, Chipley, FL 32428

  Welcome to this peaceful Sunny Hills home on over one-third of an acre with a lake view and room for a boat or RV. Major updates include a 2021 metal roof and 2021 HVAC, plus a fully fenced yard and inviting screened porch overlooking the lake.- 2021 METAL ROOF- 2021 HVAC- 2021 ELECTRIC WATER HEATER- LAKE VIEW- OVER ONE-THIRD ACRE- ROOM FOR A BOAT AND/OR RV- 10 X

  Melissa Barbee Barbee Beach House Realty

  4533 Hancock Ct, Chipley, FL 32428
• 

  

  

  /48

  $400,000

  $85K PRICE DROP

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

  3034 Paradise Lakes Rd, Chipley, FL 32428

  Get your slice of paradise on Paradise Lake Road. This beautiful, custom-built waterfront home on Dunford (Paradise Lakes) Lake is only three years old and sits on just over an acre of land. The 3-bedroom, 2-bathroom residence features hardy board siding, a new roof, custom exterior doors, luxury vinyl plank flooring, custom cabinetry, and glass shower doors--showcasing thoughtful craftsmanship

  Robert Britton World Impact Real Estate

  3034 Paradise Lakes Rd, Chipley, FL 32428
• 

  

  

  /35

  $324,900

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,903 Sq Ft

  1277 South Blvd, Chipley, FL 32428

  **Preferred Lender credit $2,000 towards closing costs** Beautifully renovated 3BR/2BA home on a spacious 3/4-acre corner lot! Rebuilt after Hurricane Michael with updated plumbing, electrical, flooring, fixtures, roof, HVAC, and water heater. Open-concept floor plan features granite countertops, soft-close cabinets, stainless steel appliances, and an oversized walk-in pantry. Wood-look porcelain

  Katie Cave Epique Realty Inc

  1277 South Blvd, Chipley, FL 32428
• 

  

  /45

  $343,999

  $56K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,494 Sq Ft

  656 4th St, Chipley, FL 32428

  Step into timeless character with thoughtful modern updates in this well-maintained historic home, now ready for its next chapter. Offering over 3,400 sq ft, this 4-bedroom, 3.5 bath residence blends classic charm with recent improvements throughout. Inside, you'll find a formal dining room and a spacious family room with a wood-burning fireplace that flows seamlessly into the breakfast nook and

  Seamus O'neill SOUTHERN WAY REALTY, INC.

  656 4th St, Chipley, FL 32428
• 

  

  /44

  $259,900

  • 4 Beds
  • 3 Baths
  • 2,736 Sq Ft

  1324 Coggin Ave, Chipley, FL 32428

  Looking for a slice of history? Look no further! Construction on this timeless home began in 1899 and was completed in 1902, offering a rare opportunity to own a piece of the past. Bursting with historical charm, the home features classic details like a clawfoot tub, a wood-burning stove in the downstairs sitting area, and a fireplace with gas logs in the living room. The main level includes a

  Cindy Birge Elite Realty

  1324 Coggin Ave, Chipley, FL 32428
• 

  

  /60

  $429,900

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 2,634 Sq Ft

  2527 Frost Ln, Chipley, FL 32428

  Welcome to 2527 Frost Lane in Chipley, a spacious 2-bedroom, 2-bathroom home offering 2,634 square feet of living space on 20.50 beautiful acres just off Pioneer Road, providing quick and convenient access to Highway 77. The home features a durable brick and vinyl exterior with a metal roof, along with a flexible floor plan that offers the potential to be reconfigured into a 3-bedroom, 2-bathroom

  Cindy Birge Elite Realty

  2527 Frost Ln, Chipley, FL 32428
• 

  

  /20

  $369,900

  • 3 Beds
  • 2 Baths
  • 1,980 Sq Ft

  498 Quail Hollow Blvd, Chipley, FL 32428

  New stairs/decks recently added! Welcome to this exceptional custom-built home, where thoughtful design, modern comfort, and future potential come together on a beautiful private corner lot in the heart of Chipley. Built in 2021 and meticulously maintained, this nearly new residence offers the perfect blend of style, accessibility, and functionality.Step inside to discover an inviting

  Holly DiMemmo LPT REALTY, LLC

  498 Quail Hollow Blvd, Chipley, FL 32428
• 

  

  /21

  $236,928

  • 1 Bed
  • 1 Bath
  • 1,234 Sq Ft

  4995 Porter Pond Rd, Chipley, FL 32428

  Welcome to your own slice of paradise on beautiful Porter Pond in Washington County, Florida. The studio/efficiency apartment is nestled on more than 2 peaceful acres. This waterfront property offers lake views and the tranquility you've been searching for. Wake up each morning to the beauty of the water, enjoy coffee while watching the sunrise, and unwind each evening surrounded by nature.

  Sharon Gavin Elite Realty

  4995 Porter Pond Rd, Chipley, FL 32428
• 

  

  /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
• 

  

  /50

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,705 Sq Ft

  4541 Hancock Ct, Chipley, FL 32428

  Wake up to peaceful lake views and enjoy a home where the setting is just as inviting as the spaces inside. Situated along Watering Lake in the Sunny Hills community, this updated 3-bedroom, 2-bath block home offers 1,776 square feet with an open layout designed for comfortable everyday living and easy entertaining. Fresh paint and new wood laminate flooring give the interior a clean, updated

  The Wheeler Sauls Collective Salty Marlin Realty LLC

  4541 Hancock Ct, Chipley, FL 32428
• 

  

  /26

  $254,900

  New Construction $22K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,832 Sq Ft

  3993 Oxford Ave, Chipley, FL 32428

  Welcome to 3993 Oxford Avenue 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

  3993 Oxford Ave, Chipley, FL 32428
• 

  

  /36

  $329,999

  $45K 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

  $225,000

  $10K PRICE DROP

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

  1060 Florida 277, Chipley, FL 32428

  Price Reduction !!! 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

  Linda Cumbaa Elite Realty

  1060 Florida 277, Chipley, FL 32428
• 

  

  /41

  $239,900

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,350 Sq Ft

  2246 Orange Hill Rd, Chipley, FL 32428

  Welcome to this 3-bedroom, 1-bath brick home built in 1975 and nestled on over 1 acre in a peaceful rural setting just minutes from town. With approximately 1,350 sq. ft., a concrete foundation, a 2018 metal roof, and a brand-new HVAC system installed in 2026, this property offers a great combination of comfort, functionality, and outdoor space. Step inside to a rustic living room that flows into

  Tina Dixon Triple Crown Realty Team

  2246 Orange Hill Rd, 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
• 

  

  /57

  $319,000

  • 3 Beds
  • 2 Baths
  • 1,414 Sq Ft

  1788 Gap Blvd, Chipley, FL 32428

  Peaceful Waterfront Retreat on 14.79 AcresEscape to your own private slice of paradise with 14.79 beautiful acres featuring a one owner double-wide mobile home overlooking a peaceful branch of Gap Pond. Enjoy breathtaking views of the water from the back porch, where you can relax and take in the beauty and tranquility of nature.This property offers access from two

  Rebecca Weeks Elite Realty

  1788 Gap Blvd, 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
• 

  

  /26

  $254,900

  New Construction $19K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,832 Sq Ft

  3890 Merger Dr, Chipley, FL 32428

  Welcome to 3890 Merger 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

  3890 Merger Dr, Chipley, FL 32428
• 

  

  /46

  $399,999

  $20K 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
• 

  

  /27

  $320,000

  $65K PRICE DROP

  • Land
  • 3 Acres
  • $106,667 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

  $215,000

  $3K PRICE DROP

  • 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

  $224,900

  $25K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  4597 Spotted Horse Ln, Chipley, FL 32428

  **Motivated seller! Bring Offers****Price Improvement + $5K toward Buyer closing costs and prepaids**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

  Stan Fowler Think Real Estate

  4597 Spotted Horse Ln, Chipley, FL 32428
• 

  

  /32

  $361,400

  New Construction

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

  2014 Ambassador Ct, Chipley, FL 32428

  Welcome to 2014 Ambassador Court at Sunny Hills in Freeport, Florida. This pre-construction homesite 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 bathrooms. As you enter this

  2014 Ambassador Ct, Chipley, FL 32428
• 

  

  /40

  $269,900

  • 3 Beds
  • 1.5 Baths
  • 1,740 Sq Ft

  672 Main St, Chipley, FL 32428

  Welcome to this charming 3-bedroom, 1.5-bath home conveniently located in the heart of Chipley, Florida. Just minutes from shopping, dining, and everyday conveniences, this property offers both comfort and convenience. Step inside to an inviting entry featuring custom wood-beamed ceilings and a beautiful sliding barn door, creating a warm and welcoming space that can serve as a cozy sitting area

  Raul Hernandez Legacy Premier Agency

  672 Main St, Chipley, FL 32428
• 

  

  /27

  $214,900

  New Construction $19K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,281 Sq Ft

  4066 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 Poppy 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

  4066 Ramus Dr, Chipley, FL 32428
• 

  

  /50

  $355,000

  $35K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,624 Sq Ft

  3243 Quail Ridge Dr, Chipley, FL 32428

  *SELLER OFFERING $10,000 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
• 

  

  /74

  $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 minutes from town, this well-maintained brick home sits on approximately 4.5 acres and offers generous living space inside and out. Features include updated windows, crown molding throughout, tile and luxury vinyl plank flooring, a formal dining room, and a

  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
• 

  

  /30

  $244,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,580 Sq Ft

  2403 Windbrook St, Chipley, FL 32428

  Welcome to 2403 Windbrook Street 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 Lismore floorplan and built to current design standards and specifications. Buyers may have the ability to personalize select finishes depending on the stage of construction.

  2403 Windbrook St, Chipley, FL 32428
• 

  

  /23

  $244,900

  New Construction $12K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,580 Sq Ft

  4127 Merrick Dr, Chipley, FL 32428

  Welcome to 4127 Merrick 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 Lismore 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

  4127 Merrick Dr, Chipley, FL 32428
• 

  

  /35

  $250,000

  • Land
  • 8.92 Acres
  • $28,027 per Acre

  000000 Rio Vista Rd, Chipley, FL 32428

  For decades, Horselot Pond has been a quiet sanctuary for the Arnone family -- a place of peaceful water views, natural beauty, and lasting memories. Now this rare multi-lot offering invites you to create your own private retreat. With the platted (but not installed) Rio Vista Road included, the property provides a wide-open canvas for your vision, whether you're dreaming of a nature-inspired

  Sheran Whitaker New Town Realty

  000000 Rio Vista Rd, Chipley, FL 32428
• 

  

  /37

  $269,999

  $10K 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

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