Homes for sale under $500k in Chipley, FL

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ABOUT THIS HOME
Homes for sale under $500k in Chipley, FL
Come settle in to this well built, well maintained, and thoughtfully updated home in the Sunny Hills subdivision. They sure don't make them like they used to! With over 2,000 square feet of living space, it boasts 4 bedrooms, 2 and a half bathrooms, a formal dining room (or office), a large living area, a Florida room that is heated and cooled, a large outbuilding wired with power, a garage, plenty of closets and storage space, many beautiful flowering plants, and more, all on almost a half acre! The kitchen, air conditioning system, paint, electrical wiring, and floors have all been updated within the last several years. The guest half bathroom has been updated, but many of the ''vintage''

$297,000

4 beds2.5 baths2,116 sq ft

2056 Sunny Hills Blvd, Chipley, FL 32428

Florida room • Updated paint • Updated floors

3D WALKTHROUGH

ABOUT THIS HOME
Homes for sale under $500k in Chipley, FL
Nestled on just under an acre (. 95 acres) in the peaceful Crystal Lake community, this beautifully maintained home offers the perfect blend of modern updates, functional space, and outdoor enjoyment. Whether you're looking for a full-time residence surrounded by nature or a relaxing second-home getaway, this property delivers comfort and charm at every turn. From the front yard, enjoy breathtaking views of Crystal Lake, visible right from your kitchen sink, dining area, and the spacious front porch—the perfect spot to enjoy your morning coffee or unwind at sunset. The yard is immaculately maintained with lush Zoysia grass, mature landscaping, and plenty of room for kids or pets to pl

$294,000

4 beds2 baths2,108 sq ft

4318 Crystal Lake Dr, Chipley, FL 32428

Lush zoysia grass • Spacious front porch • Mature landscaping

NEW CONSTRUCTION3D WALKTHROUGH

ABOUT THIS HOME
Homes for sale under $500k in Chipley, FL
Discover Your Dream Home in the Martin's Woods Community! The stylish Essex Plan this is a 2-story gem offers a spacious open layout perfect for entertaining and everyday living. The inviting kitchen features elegant cabinetry, granite countertops and stainless steel appliances, including a range with a microwave hood and a modern dishwasher. The main floor also includes a versatile flex room and a chic half bathroom for guests. Upstairs, unwind in the tranquil primary suite with an en-suite bathroom and a generous walk-in closet. Three additional bedrooms with walk-in closets share a full bathroom. A cozy loft and a convenient walk-in laundry room enhance functionality. Energy-efficient Lo

$293,990

4 beds2.5 baths2,014 sq ft

966 Lera Ln, Chipley, FL 32428

Inviting kitchen • Elegant cabinetry • Flex room

READY TO BUILD

ABOUT THIS HOME
Homes for sale under $500k in Chipley, FL
4 bed | 2 bath | 2-bay | 2014 sqft

$289,990

4 beds2.5 baths2,014 sq ft

ESSEX Plan, Chipley, FL 32428

2 garage spots • Listed 121 days

Listing provided by Zillow

NEW CONSTRUCTION3D WALKTHROUGH

ABOUT THIS HOME
Homes for sale under $500k in Chipley, FL
The Willow A Model - Homes by Deltona | Sunny Hills, FL Welcome to The Willow A, a beautifully designed 4-bedroom, 2-bath home offering 1,716 square feet of living space and 2,241 total square feet under roof. This thoughtfully planned layout combines modern comfort, functionality, and style — making it a perfect choice for families or those who love open, airy spaces. Built with concrete block construction and a stucco finish, this home is as durable as it is elegant. Inside, you'll find luxury vinyl plank flooring, 3CM granite countertops, and designer wood cabinetry with soft-close dovetail doors and drawers — all complemented by Sherwin-Williams designer paint schemes tha

$283,956

4 beds2 baths1,716 sq ft

2225 Chase St, Chipley, FL 32428

Stucco finish • 9,975 sq ft lot • 2 garage spots

Property at 4210 Auburndale Dr, Chipley, FL 32428, 3 beds, 2 baths

$282,852

3 beds2 baths1,650 sq ft

4210 Auburndale Dr, Chipley, FL 32428

Property at 3989 Horizon Ave, Chipley, FL 32428, 4 beds, 2 baths

$279,068

4 beds2 baths1,716 sq ft

3989 Horizon Ave, Chipley, FL 32428

Property at 2212 Chase St, Chipley, FL 32428, 4 beds, 2 baths

$278,848

4 beds2 baths1,728 sq ft

2212 Chase St, Chipley, FL 32428

Property at 2216 Chase St, Chipley, FL 32428, 3 beds, 2 baths

$276,692

3 beds2 baths1,650 sq ft

2216 Chase St, Chipley, FL 32428

Property at 3068 Woodymarion Dr, Chipley, FL 32428, 3 beds, 2 baths

$275,000

3 beds2 baths1,650 sq ft

3068 Woodymarion Dr, Chipley, FL 32428

Property at 3425 Quail Ridge Dr, Chipley, FL 32428, 3 beds, 2 baths

$274,900

3 beds2 baths1,377 sq ft

3425 Quail Ridge Dr, Chipley, FL 32428

Property at Freeport Plan, Chipley, FL 32428, 4 beds, 2 baths

$274,900

4 beds2 baths1,458 sq ft

Freeport Plan, Chipley, FL 32428

Listing provided by Zillow

Property at 2387 Aquarius Dr, Chipley, FL 32428, 4 beds, 2 baths

$272,344

4 beds2 baths1,728 sq ft

2387 Aquarius Dr, Chipley, FL 32428

Property at 2221 Chase St, Chipley, FL 32428, 3 beds, 2 baths

$271,312

3 beds2 baths1,556 sq ft

2221 Chase St, Chipley, FL 32428

Property at 2263 Shenandoah Blvd, Chipley, FL 32428, 3 beds, 2 baths

$271,052

3 beds2 baths1,650 sq ft

2263 Shenandoah Blvd, Chipley, FL 32428

Property at ROANOKE Plan, Chipley, FL 32428, 4 beds, 2 baths

$269,990

4 beds2 baths1,773 sq ft

ROANOKE Plan, Chipley, FL 32428

Listing provided by Zillow

Property at 2209 Chase St, Chipley, FL 32428, 3 beds, 2 baths

$269,236

3 beds2 baths1,556 sq ft

2209 Chase St, Chipley, FL 32428

Property at CABOT Plan, Chipley, FL 32428, 4 beds, 2 baths

$265,990

4 beds2 baths1,684 sq ft

CABOT Plan, Chipley, FL 32428

Listing provided by Zillow

Property at 1764 Clayton Rd, Chipley, FL 32428, 3 beds, 2 baths

$260,000

3 beds2 baths1,248 sq ft

1764 Clayton Rd, Chipley, FL 32428

$259,990

4 beds2 baths1,684 sq ft

CABOT Plan, Chipley, FL 32428

Listing provided by Zillow

Property at 2269 Rockford Dr, Chipley, FL 32428, 4 beds, 2 baths

$256,990

4 beds2 baths1,648 sq ft

2269 Rockford Dr, Chipley, FL 32428

Property at 3833 Airmont Dr, Chipley, FL 32428, 4 beds, 2 baths

$256,990

4 beds2 baths1,648 sq ft

3833 Airmont Dr, Chipley, FL 32428

Property at 1509 Southern Way, Chipley, FL 32428, 3 beds, 3 baths

$254,900

3 beds3 baths1,440 sq ft

1509 Southern Way, Chipley, FL 32428

Property at 1021 Orange Hill Rd, Chipley, FL 32428, 4 beds, 2.5 baths

$253,888

4 beds2.5 baths2,014 sq ft

1021 Orange Hill Rd, Chipley, FL 32428

Property at Aldridge Plan, Chipley, FL 32428, 3 beds, 2 baths

$252,900

3 beds2 baths1,293 sq ft

Aldridge Plan, Chipley, FL 32428

Listing provided by Zillow

Property at BEAUMONT Plan, Chipley, FL 32428, 3 beds, 2 baths

$250,990

3 beds2 baths1,416 sq ft

BEAUMONT Plan, Chipley, FL 32428

Listing provided by Zillow

Property at 3309 Lykins Rd, Chipley, FL 32428, 4 beds, 2 baths

$250,000

4 beds2 baths2,128 sq ft

3309 Lykins Rd, Chipley, FL 32428

Property at 3931 Vistula Dr, Chipley, FL 32428, 3 beds, 2 baths

$250,000

3 beds2 baths1,535 sq ft

3931 Vistula Dr, Chipley, FL 32428

Property at 4494 Leisure Lakes Dr, Chipley, FL 32428, 4 beds, 2 baths

$250,000

4 beds2 baths2,052 sq ft

4494 Leisure Lakes Dr, Chipley, FL 32428

Property at 4139 Aquarius Dr, Chipley, FL 32428, 4 beds, 2 baths

$249,990

4 beds2 baths1,648 sq ft

4139 Aquarius Dr, Chipley, FL 32428

Property at 4131 Aquarius Dr, Chipley, FL 32428, 4 beds, 2 baths

$249,990

4 beds2 baths1,648 sq ft

4131 Aquarius Dr, Chipley, FL 32428

Property at 672 Main St, Chipley, FL 32428, 3 beds, 1.5 baths

$247,000

3 beds1.5 baths1,740 sq ft

672 Main St, Chipley, FL 32428

$245,990

4 beds2 baths1,684 sq ft

CABOT Plan, Chipley, FL 32428

Listing provided by Zillow

Property at 2335 Walkerton Dr, Chipley, FL 32428, 3 beds, 2 baths

$244,995

3 beds2 baths1,270 sq ft

2335 Walkerton Dr, Chipley, FL 32428

Property at 2362 Shenandoah Blvd, Chipley, FL 32428, 4 beds, 2 baths

$244,900

4 beds2 baths1,458 sq ft

2362 Shenandoah Blvd, Chipley, FL 32428

Property at 220 Highway 77, Chipley, FL 32428, 3 beds, 2 baths

$242,000

3 beds2 baths2,170 sq ft

220 Highway 77, Chipley, FL 32428

Property at 2219 Voltaire Dr, Chipley, FL 32428, 3 beds, 2 baths

$239,900

3 beds2 baths1,262 sq ft

2219 Voltaire Dr, Chipley, FL 32428

Property at 2292 Rockford Dr, Chipley, FL 32428, 3 beds, 2 baths

$239,900

3 beds2 baths1,262 sq ft

2292 Rockford Dr, Chipley, FL 32428

Property at 2349 Dumajack Rd, Chipley, FL 32428, 3 beds, 2 baths

$239,900

3 beds2 baths1,262 sq ft

2349 Dumajack Rd, Chipley, FL 32428

Property at Callaway Plan, Chipley, FL 32428, 3 beds, 2 baths

$239,900

3 beds2 baths1,204 sq ft

Callaway Plan, Chipley, FL 32428

Listing provided by Zillow

Property at 2294 Rockford Dr, Chipley, FL 32428, 3 beds, 2 baths

$239,900

3 beds2 baths1,262 sq ft

2294 Rockford Dr, Chipley, FL 32428

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Based on information submitted to the MLS GRID as of Sun Nov 30 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Homes for sale under $500k in Chipley

There are currently 138 homes for sale under $500k in Chipley. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chipley stay on the market for 130 days. This map is refreshed with the newest listings in Chipley every 15 minutes.

In the past month, 1 home has been sold in Chipley. In addition to houses in Chipley, there were also 0 condos, 1 townhouse, and 1 multi-family unit for sale in Chipley last month. Find your dream home in Chipley using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chipley are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chipley. Our Chipley real estate stats and trends will give you more information about home buying and selling trends in Chipley. If you're looking to sell your home in the Chipley area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chipley with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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