Chickasha Real Estate

Welcome to Chickasha, Oklahoma, a vibrant city nestled in the heart of Grady County. Known for its rich history and welcoming community, Chickasha offers a charming blend of small-town warmth and modern amenities, making it an ideal place to call home.

With a population of just over 16,000 residents, Chickasha boasts a close-knit atmosphere where neighbors become friends. The city is renowned for its annual events, including the beloved Chickasha Festival of Light, which transforms the downtown area into a winter wonderland each holiday season. Throughout the year, residents and visitors alike can enjoy local farmers' markets, art festivals, and community gatherings that celebrate the unique spirit of this Oklahoma gem.

Chickasha is also home to a variety of parks and recreational facilities, perfect for outdoor enthusiasts. Whether you’re exploring the scenic trails at Shannon Springs Park or enjoying a leisurely afternoon at the local golf course, there’s no shortage of ways to embrace the great outdoors. Families will appreciate the top-rated schools and safe neighborhoods, creating a nurturing environment for children to thrive.

For those who appreciate a taste of history, Chickasha is rich with heritage, featuring several historic landmarks and museums that tell the story of its past. The city is conveniently located just a short drive from larger metropolitan areas, providing easy access to additional shopping, dining, and entertainment options.

In Chickasha, you’ll find not just a place to live, but a community to belong to. Come discover the charm and warmth of Chickasha, where every day feels like home.

Newest Listings in Chickasha

$299,000

2 Beds ⋅ 3 Baths ⋅ 1255471 MLS

This beautifully completely remodeled duplex offers an incredible opportunity for investors or buyers looking to live in one unit while generating rental income from the other! The property also includes and additional empty lot to the West of the duplex. Each unit features 2 bedrooms and 1 bathroom, providing a total of 4 bedrooms and 2 bathrooms. Both units have undergone extensive renovations, offering fresh, modern interiors with beautiful new flooring, stylish cabinetry, and updated fixtures throughout. Additional improvements include new windows, roof, plumbing and new central heat/AC units. Both units have new appliances, including high end washer and dryers. The kitchens have gorgeous granite countertops, modern cabinetry, and sleek finishes. The bright, inviting living spaces offer a clean, contemporary feel, making both units attractive and comfortable. LOCATION, LOCATION, LOCATION! Conveniently situated within walking distance of local restaurants, banking, and grocery shopping, this property offers everyday convenience for residents. With extensive updates already completed, this turnkey duplex is an excellent addition to any investment portfolio or a fantastic opportunity for an owner-occupant looking to offset their mortgage with rental income. There is also an option to purchase the entire corner, that would be 5 doors total. Seller has a portfolio for sale including 10 doors total. Will separate.

715 W Wisconsin Avenue, Chickasha

$345,000

4 Beds ⋅ 4 Baths ⋅ 1252146 MLS

2,000 Sq Ft | Garage | Investment Opportunity | Incentives Available! This fully leased duplex features two units, each offering 2 bedrooms and 2 bathrooms, along with a dedicated laundry room with washer and dryer included. Each unit provides a functional layout with comfortable living spaces, natural light, all major appliances, blinds, and a fenced backyard area. A garage provides additional parking and storage space for each unit. Additional features include granite countertops, LVP wood-look flooring, and tiled shower walls, offering durable finishes designed for everyday use. Conveniently located with access to local amenities, schools, Fort Sill, and Mt. Scott. Schedule a showing today to explore this income-producing duplex opportunity. The property is owned by a licensed Oklahoma Real Estate Agent #210370.

3310 S 23rd, Chickasha

$175,000

3 Beds ⋅ 2 Baths ⋅ 1255399 MLS

Character and curb appeal welcome you to 1827 S 20th St in Chickasha! A distinctive blue painted-brick exterior and covered front porch framed by charming arches set the tone for this inviting home. Inside, warm wood floors, large windows, and neutral colors create a bright, comfortable atmosphere. The spacious living area features a classic mantel, while a wide opening connects the adjoining living and dining spaces. Built-in cabinetry adds both personality and practical storage. The kitchen offers white cabinetry, a mosaic tile backsplash, stainless steel appliances, a gas range, and a convenient pass-through to the adjoining dining area. A window above the sink brings in natural light, and arched interior doorways carry the home’s architectural character throughout. Outside, the covered porch provides a welcoming spot for morning coffee, with yard space ready for your landscaping touches. Full of distinctive details and opportunities to make it your own, this home deserves a closer look. Schedule your showing today!

1827 S 20th Street, Chickasha

$425,000

1255320 MLS

Think outside the box here! This is such a cool space with endless possibilities! The building is currently being used as a marine repair shop, however, with accessibility to downtown, there could be lots of other uses. There are two buildings available. The original space has a concrete floor with the most amazing tin ceiling tiles around! There is a faux wall separating it into two areas, and there is a small office that has been sectioned off with AC added. The second building is a metal building insulated and equipped with electricity and overhead doors. The property is fenced and there is space to add addl building(s) or add on to the existing structure and or add a truck bay. There is an overhead door on each building with on premise parking or street parking. Property sits just a block south of Chickasha Ave. between 2nd and 3rd Street. Future plans include a park off of 2nd, just east of this location. The Grady Co Fairgrounds is nearby as well as the Leg Lamp and lots of Chickasha's downtown attractions. Realist tax forms show buildings as 3700 sq ft and 4125 sq ft. Buyer to verify sq footage and flood status.

215 Kansas Avenue, Chickasha

$345,000

4 Beds ⋅ 4 Baths ⋅ 1252067 MLS

Brand New Duplex | Garage | Investment Opportunity | Incentives Available! This new construction duplex features two units, each offering 2 bedrooms and 2 bathrooms, along with a dedicated laundry room with washer and dryer included. Each unit provides a functional layout with comfortable living spaces, natural light, all major appliances, blinds, and a fenced backyard area. A garage provides additional parking and storage space for each unit. Additional features include granite countertops, LVP wood-look flooring, and tiled shower walls, offering durable finishes designed for everyday use. Conveniently located with access to local amenities, schools, Fort Sill, and Mt. Scott. Schedule a showing today to explore this income-producing duplex opportunity. The property is owned by a licensed Oklahoma Real Estate Agent #210370. Call for your tour today!

3316 S 23rd, Chickasha

$115,000

3 Beds ⋅ 1 Baths ⋅ 1254271 MLS

This charming 3-bedroom, 1-bath home offers a wonderful combination of character, comfort, and updates. Step inside to discover new flooring throughout, neutral tones, and spacious rooms filled with natural light. The home features two mini-split heating and cooling systems for added comfort and efficiency. An enclosed back porch provides additional space for storage or hobbies. Outside, you’ll appreciate the attractive dark exterior, metal roof, and inviting covered front porch, perfect for relaxing and enjoying the outdoors. The spacious yard offers room for outdoor activities. Whether you’re searching for a primary residence or an investment opportunity, this property has plenty to offer. Schedule your private showing today!

927 S 18th Street, Chickasha

$345,000

4 Beds ⋅ 4 Baths ⋅ 1252009 MLS

This beautifully appointed duplex offers two units, with each featuring 2 bedrooms and 2 bathrooms, and a dedicated laundry room (washers and dryers are included!). The functional layouts with comfortable living spaces and plenty of natural light are complete with all major appliances, blinds, and a fenced backyard area. The benefits for this investment property don't end there! Granite countertops, LVP wood-look flooring, and tiled shower walls offer both beauty that your tenants will love and longevity for the property. Conveniently located with access to local restaurants and shopping. Schedule your showing today and explore this income-producing duplex opportunity! The property is owned by a licensed Oklahoma Real Estate Agent #210370

3312 S 23rd, Chickasha

$159,000

3 Beds ⋅ 2 Baths ⋅ 1254959 MLS

Step back in time to this very well kept charmer with original hardwoods in a good portion of the house, lovely built-ins bround the fireplace, and a wonderful sitting porch for daydreaming! The roof is brand new and any loan type will be acceptable! With 3 bedroom and 2 full baths, this house also offers a bright kitchen, in home laundry area and a cellar/basement accessible from inside the home. There is a fully fenced yard and a single detached garage with opener for safety and security. The large corner lot offers plenty of space to play and stay!

1528 W Missouri Avenue, Chickasha

$234,900

3 Beds ⋅ 2 Baths ⋅ 1252072 MLS

This thoughtfully designed 3-bedroom, 2-bathroom home with a 2-car attached garage offers modern finishes, functional living spaces, and quality craftsmanship in Chickasha. The open-concept floor plan connects the living, dining, and kitchen areas, providing a functional layout for everyday living. Luxury vinyl plank flooring extends throughout the main living areas, while large windows provide natural light. The kitchen features granite countertops, ample cabinet storage, and a full suite of stainless steel appliances, including a refrigerator, gas range, microwave, and dishwasher, along with a washer and dryer. The primary suite includes a walk-in closet and a private bathroom with dual vanities and a tiled walk-in shower. Two additional bedrooms provide flexible space for guests, a home office, or other needs, with a second full bathroom conveniently located nearby. Additional features include a dedicated laundry room, white faux wood blinds, and an attached two-car garage. Conveniently located near local schools, shopping, dining, and major roadways, this home provides access to everyday amenities. Call to schedule a tour today!

1217 S Park Avenue, Chickasha

$169,900

3 Beds ⋅ 2 Baths ⋅ 1254976 MLS

Fully remodeled and move-in ready! These 3 beds, 2 bath home at 912 S 16th St in Chickasha offers 1,328 sq ft of updated living space, priced at $169,900. The remodel went well beyond cosmetic: all new plumbing, a new electrical panel, and a combo heat and air unit give you peace of mind for years to come. Inside, new LVP flooring runs throughout, and fresh paint brightens every room. The kitchen and both bathrooms have been completely renovated. The living room is anchored by a cozy fireplace and includes a flexible nook that works great as a home office, play area, or extra space for entertaining guests. Outside, enjoy a large covered front porch, a smaller covered back porch, and a fenced backyard. Fresh exterior paint and a detached one-car garage complete the package. Have questions about financing? Contact your Realtor for information about local lenders and available financing options. Schedule your showing today!

912 S 16th Street, Chickasha

$235,000

3 Beds ⋅ 2 Baths ⋅ 1254402 MLS

Welcome to 311 Christopher Drive in Chickasha! This 3-bedroom, 2-bathroom home offers approximately 1,763 square feet of living space on a 10,018-square-foot lot. Located in a well-established neighborhood right beside the Drover Hills Country Club golf course, this property offers a rare opportunity in an area where homes don’t come up for sale often. A brand-new roof installed October 15, 2026, adds value to the home. The backyard offers potential for your own outdoor retreat, complete with an in-ground pool that is currently not in working condition and will require some TLC. Bring your vision to create a welcoming spot for relaxing, entertaining, and gathering with family and friends. Schedule your showing and explore the possibilities!

311 Christopher Drive, Chickasha

$139,000

3 Beds ⋅ 1 Baths ⋅ 1254230 MLS

3-bedroom home situated on a large corner lot in Chickasha. Offering a spacious living area with beautiful flooring, abundant natural light, and a comfortable layout. The kitchen offers plenty of cabinet space and opens to a dining area, making everyday living and entertaining a breeze. This home has the character you're looking for. Step outside and enjoy the beautiful backyard deck, perfect for morning coffee, weekend cookouts, or simply relaxing outdoors. The spacious yard offers plenty of room for outdoor activities, while the detached garage provides additional parking or storage. Additional highlights include a custom West Shore back door, cellar and an existing security system that stays with the property! With its welcoming atmosphere, functional layout, and wonderful outdoor space, this home has so much to offer. Schedule your private showing today!

1327 S 16th Street, Chickasha

Start Your Search

Copyright © 2026 MLSOK, Inc. This information is believed to be accurate but is not guaranteed. Subject to verification by all parties. The listing information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. This data is copyrighted and may not be transmitted, retransmitted, copied, framed, repurposed, or altered in any way for any other site, individual and/or purpose without the express written permission of MLSOK, Inc. Information last updated on .

Chickasha Real Estate

Newest Listings in Chickasha

How much is your home worth?

How much is your home worth?