Vintage homes for sale & real estate in Chipley, FL

11 homes

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ABOUT THIS HOME
Vintage Home for sale in Chipley, FL:
This 3-bedroom, 2.5-bath home is nestled on a massive 1.34-acre lot within the city limits of Chipley, an ideal blend of space and location. This home is ready for a refresh and offers a great starting point to create the space you've been dreaming of. Whether you're looking for a primary residence or an investment property, this one has the space and location to make it worthwhile. Just a short walk to local schools, restaurants, and all that downtown Chipley has to offer!

$149,999

3 beds2.5 baths2,040 sq ft

777 West Blvd, Chipley, FL 32428

1.34 acre lot • Parking • Built 1956

ABOUT THIS HOME
Vintage Home for sale in Chipley, FL:
Charming 3-Bedroom Home and the Potential for a Commercial Opportunity in the Heart of Chipley, FL * * Welcome to this delightful 3-bedroom, 1.5-bathroom home located in the picturesque small town of Chipley, Florida—home to the stunning Falling Waters State Park and the beloved Watermelon Festival! This unique property is just steps away from local boutiques, hair salons, mouth-watering down south BBQ, and the best coffee shop for miles, making it an ideal spot for both relaxation and entertainment. As you enter the home, you are greeted by an inviting open area featuring custom beamed ceilings & custom barn door, perfect for a cozy sitting area or a stylish dining room. The

$247,000

3 beds1.5 baths1,740 sq ft

672 Main St, Chipley, FL 32428

Open-concept design • Custom bookshelves • Custom barn door

ABOUT THIS HOME
Vintage Home for sale in Chipley, FL:
BACK ON THE MARKET - NO FAULT OF SELLER! Discover the perfect blend of charm and convenience with this delightful Florida cottage, ideally situated on a spacious corner lot in the heart of downtown Chipley. Recent updates, including some new double-pane windows, laminate flooring, and fresh exterior paint, enhance the home's appeal and functionality. This home features a fully fenced backyard, offering privacy and space for outdoor activities. The flexible floor plan features a bonus room that can serve as either a bedroom or an office. Additionally, the master bedroom offers the option to be divided into two separate rooms—each with its own closet. One side even includes a walk-in cl

$164,900

3 beds2 baths1,428 sq ft

804 8th St, Chipley, FL 32428

0.31 acre lot • Garage • Built 1936

ABOUT THIS HOME
Vintage Home for sale in Chipley, FL:
Welcome to this charming cottage-style home located at 1222 Campbellton Avenue in Chipley! Nestled on an almost 0.3-acre lot, this property combines character, charm, and convenience — offering easy access to Hwy 273 and Hwy 77. This 3-bedroom, 1-bathroom home features a cozy galley-style kitchen and a warm, inviting atmosphere throughout. Enjoy relaxing on the large front porch, perfect for morning coffee or unwinding after a long day while taking in the peaceful surroundings. Outside, the yard is beautifully enhanced with several mature pecan trees, a stunning oak, and even a few lemon trees, creating a serene and picturesque setting. Ideally located just 40 minutes from Dothan,

$119,900

3 beds1 bath1,064 sq ft

1222 Campbellton Ave, Chipley, FL 32428

Mature pecan trees • Galley-style kitchen • Large front porch

ABOUT THIS HOME
Vintage Home for sale in Chipley, FL:
Country Cottage on 2.9 Acres with Guest Home & Multi-Family Potential! Tucked away on nearly 3 peaceful acres, this charming country cottage offers space, flexibility, and room to grow. Whether you're looking for a homestead, income-producing opportunity, or multi-generational living, this property is packed with potential. The main home features a metal roof installed in 2019 and includes two AC units for efficient climate control. With vinyl siding for low maintenance and a massive 24x51 ft 4-car garage, there's no shortage of space for vehicles, hobbies, or storage needs. Inside, enjoy a cozy living room with laminate flooring and an electric fireplace—perfect for relaxing

$349,000

3 beds2 baths2,108 sq ft

723 Sewell Farms Rd, Chipley, FL 32428

Laminate flooring • Metal roof • 4-car garage

Property at 807 Maple St, Chipley, FL 32428, 4 beds, 2 baths

$340,000

4 beds2 baths2,897 sq ft

807 Maple St, 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 896 Main St, Chipley, FL 32428, 5 beds, 3 baths

$650,000

5 beds3 baths2,184 sq ft

896 Main St, Chipley, FL 32428

Property at 3753 Bunyon Dr, Chipley, FL 32428

$145,000

— beds— baths— sq ft

3753 Bunyon Dr, Chipley, FL 32428

Property at 1291 Morris Ave, Chipley, FL 32428

$35,999

— beds— baths— sq ft

1291 Morris Ave, Chipley, FL 32428

Property at 0000 South Blvd, Chipley, FL 32428

$89,000

— beds— baths— sq ft

0000 South Blvd, Chipley, FL 32428

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ABOUT THIS HOME
Vintage Home for sale in Chipley, FL:
Brick Home in the Heart of Downtown! This 3-bedroom, 2-bath brick home has been fully renovated inside and out, offering modern comfort with timeless charm. Perfectly situated on a spacious corner lot, this move-in-ready home is located right in the heart of downtown—close to local restaurants, the hospital, and convenient grocery shopping. Step inside to find a bright and welcoming layout featuring a large kitchen, ideal for preparing family meals that can be enjoyed on the oversized back deck. The elegant arched entryway from the dining area adds a touch of classic character and style. Nestled next door to the historic Waits Mansion, the home enjoys a beautiful setting that comes a

$255,000

4 beds2 baths1,586 sq ft

203 W Kansas Ave, Bonifay, FL 32425

Fully renovated • Oversized back deck • Arched entryway

ABOUT THIS HOME
Vintage Home for sale in Chipley, FL:
This home was completely gutted down to the foundation and rebuilt with quality in mind. Major improvements include a new sewer line, new vent stacks, all-new wiring, PEX plumbing, newly framed walls, spray foam insulation, and moisture-resistant drywall throughout. The swirl-pattern ceiling was thoughtfully preserved, and the home features all-new single-hung double-pane windows along with new structural elements, including new subflooring. The bathroom has been fully renovated, and an additional bathroom has been added to the master bedroom, offering extra convenience and value. This partially renovated home is being sold as-is and is ready for you to complete the finishing touches! Conve

$119,900

2 beds2 baths786 sq ft

609 W Kansas Ave, Bonifay, FL 32425

Mini-split system • Fenced yard • Florida room

ABOUT THIS HOME
Vintage Home for sale in Chipley, FL:
Want to live off the grid? This unique property offers a great start for your homestead or getaway. Home is being sold As Is. According to the Property Appraiser, built in 1950 with an effective year built of 2022 and may have originally been a barn. Features include a concrete foundation, paneling and sheetrock walls, vinyl flooring, and wood sheathing ceiling. Electric installed with designated areas for a kitchen and bathroom, but plumbing not yet completed. Property includes an outdoor shed used as a bathhouse, window A/C unit, and space for two bedrooms. Covered front porch and attached carport. Almost 3 acres with approximately ¾ of an acre level lot, mostly cleared, with parti

$79,900

1 bed— baths720 sq ft

1680 Will Lee Rd, Bonifay, FL 32425

Covered front porch • Vinyl flooring • Concrete foundation

ABOUT THIS HOME
Vintage Home for sale in Chipley, FL:
Rare Find! Fronts on the 15th fairway at the Beautiful Dogwood Lakes Golf Course. Sits on approx. 1 acre with some large shade trees in a secluded setting. Older home is in good condition with a new roof installed about 7 years ago. This is an 18-hole golf course with very reasonable green fees and a 52-acre Lake with some great fishing. All this and no HOA fees.

$205,000

3 beds1 bath1,184 sq ft

1900 Olive Ln, Bonifay, FL 32425

15th fairway • 18-hole golf course • Large shade trees

ABOUT THIS HOME
Vintage Home for sale in Chipley, FL:
38 Acres with Multi-Family & Investment Potential - Holmes County This versatile property offers endless opportunity for investors or those seeking multi-family living. It features a large pond with pump, 36x24 pole barn, six RV hookups, three wells, two septic tanks, and 15 electric poles—excellent infrastructure already in place. The land includes two homes: a 1,690 sq. ft. 4BR/2BA block home and a 3BR/2BA mobile home, both ready for renovation or income-producing rentals. With fruit and nut trees, seasonal Chanterelle mushrooms, and abundant wildlife, this property blends country charm with investment value. A rare chance to create, develop, or expand in Holmes County!

$339,000

4 beds2.5 baths3,322 sq ft

1718 Robbins Brg, Bonifay, FL 32425

Six rv hookups • 36x24 pole barn • Two septic tanks

ABOUT THIS HOME
Vintage Home for sale in Chipley, FL:
Welcome to this inviting 3-bedroom, 2-bathroom home situated on a desirable corner lot in the heart of Bonifay. Step inside and discover an oversized formal living room, perfect for gathering or entertaining. The spacious master suite offers a private retreat complete with a cozy sitting area, while the formal dining room features built-in cabinetry that adds both charm and functionality. A separate den provides additional living space, and the 1-car attached carport adds everyday convenience. Outside, a detached building includes an additional bedroom with its own window A/C, ideal for guests, a hobby room, or a private office. Recent updates include a new shingle roof and a newer water he

$349,900

3 beds2 baths2,501 sq ft

110 W Michigan Ave, Bonifay, FL 32425

Master suite • Built-in cabinetry • Separate den

Property at 402 E Pennsylvania Ave, Bonifay, FL 32425, 3 beds, 2 baths

$258,900

3 beds2 baths1,728 sq ft

402 E Pennsylvania Ave, Bonifay, FL 32425

Property at 308 S Depot St, Bonifay, FL 32425, 3 beds, 1 bath

$159,900

3 beds1 bath1,261 sq ft

308 S Depot St, Bonifay, FL 32425

Property at 668 Wrights Creek Rd, Caryville, FL 32427, 3 beds, 2 baths

$159,000

3 beds2 baths1,695 sq ft

668 Wrights Creek Rd, Caryville, FL 32427

Property at 1748 Georgia St, Alford, FL 32420, 8 beds, 4 baths

$595,000

8 beds4 baths5,076 sq ft

1748 Georgia St, Alford, FL 32420

Property at 402 Hatcher Dr, Bonifay, FL 32425, 3 beds, 1 bath

$99,000

3 beds1 bath1,000 sq ft

402 Hatcher Dr, Bonifay, FL 32425

Property at 207 Compass Lake Dr, Alford, FL 32420, 3 beds, 2 baths

$1,200,000

3 beds2 baths1,785 sq ft

207 Compass Lake Dr, Alford, FL 32420

Vintage Homes for Sale in Chipley

There are currently 11 vintage homes for sale in Chipley at a median listing price of $200K. 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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