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

$254,990

4 Beds ⋅ 2 Baths ⋅ 1248437 MLS

This is more than a new home—it’s the fresh start you’ve been longing for. Step inside and feel the difference: soaring elevated ceilings, sunlight pouring into an open, spacious layout designed to breathe with you, not press in around you. Every detail speaks of care and comfort—luxury vinyl plank flooring underfoot, gleaming quartz countertops that elevate every moment in the kitchen. This isn’t just about beauty. It’s smart, too—energy efficient from top to bottom, with an EV charger ready for the future you’ve worked so hard to build. But here's the truth: homes like this don’t wait. Not in this market. Not with features like these. And not with the feeling you get the moment you walk through the door—the undeniable sense that this is it. Don’t let this one slip away. This is your chance. Schedule your showing today!

928 Hazy Brook Circle, Chickasha

$100,000

4 Beds ⋅ 1 Baths ⋅ 1248191 MLS

Offering fantastic functionality and space to spread out, this 4-bedroom, 1-bathroom Chickasha residence delivers an ideal layout for buyers seeking room to grow both inside and out. The interior provides four flexible bedrooms that can easily adapt to house a growing household, a home office, or a dedicated hobby room. Outside, the property truly shines with a expansive covered carport for weather-protected parking, alongside multiple outdoor storage sheds and versatile utility buildings—perfect for storing tools, setting up a custom workshop, or housing recreational equipment. Ideally located with quick access to local schools, parks, and downtown amenities, this property combines everyday practical convenience with incredible utility and outdoor potential—reach out today to schedule your private tour!

1923 W Louisiana Avenue, Chickasha

$320,000

4 Beds ⋅ 4 Baths ⋅ 1248047 MLS

This stately home catches the eye of everyone who passes! From the large corner lot, gorgeous brick/panel fencing and grand entrance, you may love the interior even more. The curved foyer staircase leads your eye up the second floor landing and enhances the high ceiling at the entrance. On the lower level, you'll find a formal dining room, office/den, kitchen and breakfast area, laundry, 1/2 bath, large family room, and a jr primary suite. Upstairs, the primary and en suite bathroom, hall bath and two guest bedrooms. And if storage is what you need, the home has it...18 closets, per owner. The backyard offers a nice covered patio, and built in flower beds. This is a must see if you need a home with lots of space!

116 Caulder Drive, Chickasha

$209,900

3 Beds ⋅ 2 Baths ⋅ 1248029 MLS

Space, updates, and a backyard made for living—without the higher price tag. This well-maintained 3-bedroom, 2-bath brick home offers 1,735 square feet of comfortable living space in Chickasha. Inside, you’ll find a spacious living room, an inviting kitchen with plenty of workspace and storage, and an open dining area that makes everyday living and entertaining easy. Wood-look tile runs through the main living areas, adding a clean, updated look while standing up to everyday life. The layout offers room to spread out, with three bedrooms and two full baths, making it a great fit for a growing household, first-time buyer, or anyone ready for more space. The large privacy-fenced backyard is one of the standout features, providing plenty of room for pets, play, cookouts, gardening, or simply enjoying Oklahoma evenings. If you’ve been looking for a home that gives you more living space, a substantial backyard, and the features you actually need at an attainable price point, this one deserves a closer look. Come see how much home you can get in Chickasha.

2225 W Country Club Road, Chickasha

$140,000

2 Beds ⋅ 2 Baths ⋅ 1248020 MLS

This charming, well-maintained property features a welcoming front porch and a spacious fenced backyard with plenty of room for outdoor activities. Upon entering the home, you’ll immediately notice the inviting atmosphere, enhanced by newly updated dark, moody interior walls that add depth and character throughout. The cozy living room features large windows that allow natural light to beautifully contrast and brighten the rich interior tones. The kitchen is modern and fully equipped with stainless steel appliances. The bedrooms are generously sized, and the primary suite includes spacious closets and a recently remodeled en-suite bathroom. The large basement provides laundry space along with ample storage. A detached two-car garage and carport offer additional storage and convenient access to the back door. As an added bonus, the property includes a 456 sq ft outbuilding that could be finished out and rented, bringing the total square footage of the property to 1,985 sq ft.

802 S 14th Street, Chickasha

$65,000

2 Beds ⋅ 1 Baths ⋅ 1248006 MLS

Great opportunity to finish this home and make it your own! This 2-bedroom, 1-bath home has been taken down to the studs, giving the next owner a head start on the renovation process. Major improvements already completed include new electrical wiring, new plumbing, and new windows. The unfinished interior provides a blank canvas to complete the home to your own style and specifications. Situated on a nice corner lot with a fenced yard, the property also features decks at both the front and back of the home, offering plenty of outdoor space. Whether you’re an investor looking for your next project or a buyer wanting the opportunity to finish a home exactly the way you want it, this property has plenty of potential. Much of the behind-the-walls work has already been started—bring your vision and finish it out!

1501 S 6th Street, Chickasha

$184,900

3 Beds ⋅ 2 Baths ⋅ 1247608 MLS

Embrace character and opportunity with this classic 3-bedroom, 2-bathroom Craftsman-style brick home located in a quiet Chickasha neighborhood. A cozy, covered front porch welcomes you into a functional layout where the kitchen stands out with rich, warm stained wood cabinetry and ample storage space. For bonus versatility, ductwork is already installed in the finished attic space, offering fantastic future expansion potential (attic space is not included in the posted square footage). Outside, a detached garage provides parking, additional storage, or a prime workspace setup for hobbies and projects. Whether you are searching for a character-filled personal residence or a high-upside investment property, this versatile home offers a sturdy foundation and endless possibilities to add value—reach out today to schedule your private tour!

1402 S 19th Street, Chickasha

$145,000

3 Beds ⋅ 1 Baths ⋅ 1247600 MLS

This Home is all ready!!! With updates like...new water, sewer and gas lines have been installed, Freshly painted, new garage door opener, and New Water Heater!! Schedule your showing today!

701 S 14th Street, Chickasha

$288,500

4 Beds ⋅ 2 Baths ⋅ 1247458 MLS

MOVE IN READY, close in 30 days! $0 down options, USDA & VA eligible!! rate buy down options!! This beautifully crafted home combines comfort and style in the highly sought-after Sleepy Hollow community! Fall in love with this spacious 4 bed, 2 bath brand new energy-efficient home that perfectly blends comfort, style, and smart living. From the moment you walk in, the elevated ceilings in the living areas and primary suite create an open, airy feel that’s simply unforgettable. Enjoy gorgeous quartz countertops, luxury vinyl plank flooring, and a layout designed for real life—roomy, modern, and made to impress. You’ll love knowing this home is built for the future, with a high-efficiency HVAC system, EV charger, tankless water heater, and a 10-year structural warranty providing peace of mind. Outside, the beautifully landscaped yard creates instant curb appeal, making this house feel like home from the very first glance. Located just minutes from the Turnpike and close to major employers like Cimarron Trailer, Standley Systems, HSI Sensing, LSPI, and Fort Sill, you’ll have both convenience and community right at your doorstep. Don’t wait—this is your chance to own new construction at an incredible value! Reserve this home today before someone else calls it home.

920 Hazy Brook Circle, Chickasha

$244,500

3 Beds ⋅ 2 Baths ⋅ 1247457 MLS

MOVE IN READY, close in 30 days! USDA & VA eligible!! Rate buy down options!!! This is more than a new home—it’s the fresh start you’ve been longing for. Step inside and feel the difference: soaring elevated ceilings, sunlight pouring into an open, spacious layout designed to breathe with you, not press in around you. Every detail speaks of care and comfort—luxury vinyl plank flooring underfoot, gleaming quartz countertops that elevate every moment in the kitchen. This isn’t just about beauty. It’s smart, too—energy efficient from top to bottom, with an EV charger ready for the future you’ve worked so hard to build. You’ll love knowing this home is built for the future, with a high-efficiency HVAC system, EV charger, tankless water heater, and a 10-year structural warranty providing peace of mind. Outside, the beautifully landscaped yard creates instant curb appeal, making this house feel like home from the very first glance. Located just minutes from the Turnpike and close to major employers like Cimarron Trailer, Standley Systems, HSI Sensing, LSPI, and Fort Sill, you’ll have both convenience and community right at your doorstep. Don’t wait—this is your chance to own new construction at an incredible value! But here's the truth: homes like this don’t wait. Not in this market or this community. Not with features like these. And not with the feeling you get the moment you walk through the door—the undeniable sense that this is it. Don’t let this home slip away. This is your chance. Secure your new home in the fast selling Sleepy Hollow community today!

924 Hazy Brook Circle, Chickasha

$199,900

4 Beds ⋅ 2 Baths ⋅ 1247000 MLS

Welcome home! This spacious 4-bedroom, 2-bath home is ideally situated on a corner lot within walking distance to local schools and USAO. The inviting open-concept layout features a large kitchen, living, and dining area designed for comfortable everyday living and entertaining. Step outside to the large covered patio, perfect for gatherings, relaxing, and enjoying the outdoors. The thoughtful floor plan offers three generously sized bedrooms on one end of the home, while the private mother-in-law suite is located on the opposite end, providing flexibility and added privacy for guests or family members. With plenty of space, a functional layout, and an unbeatable location, this home is one you won’t want to miss. Come take a look—you may just find the perfect place to call home!

2501 S 18th Street, Chickasha

$165,000

3 Beds ⋅ 3 Baths ⋅ 1247400 MLS

Great investment opportunity with an established tenant already in place! This 3-bedroom, 1.5 bath home is currently rented on a month-to-month lease, making it a great option for an investor looking to add an income-producing property to their portfolio. Situated on a large lot with a fenced backyard and no close neighbors, the property offers plenty of space and privacy. Conveniently located just off Highway 19, providing easy access to Chickasha and surrounding highways while still offering a quieter, more private setting. Whether you're looking for your next rental property or a home with room to spread out, this property offers plenty of potential.

921 E Highway 19, Chickasha

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