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

$185,000

3 Beds ⋅ 2 Baths ⋅ 1241292 MLS

Situated on just under a half-acre, this beautifully maintained home offers a spacious, fully fenced backyard with plenty of room to relax, play, and entertain. Located just one block from Chickasha's highly sought-after Shannon Springs Park, you'll enjoy easy access to scenic walking trails, the community pool, and multiple playgrounds right outside your door. Inside, the home features two generous living areas, with one easily serving as a fourth bedroom, home office, or flex space to fit your needs. The open layout between the living and kitchen areas creates an inviting atmosphere that's perfect for everyday living and hosting family and friends. For added peace of mind, the homeowner recently installed a durable metal roof designed to provide years of reliable protection. The oversized two-car garage offers ample space for vehicles, storage, and hobbies, while the property also includes a storm shelter and storage shed for added convenience. Freshly touched up and move-in ready, this home is clean, well cared for, and waiting for its next owner to make it their own!

2 Shannon Drive, Chickasha

$599,000

1241240 MLS

Prime Commercial Opportunity right off of Busy Highway 81! Excellent investment opportunity at 404 W. Country Club Rd. This 3,320± square foot commercial property features three separate retail/office units, offering flexibility for investors or owner-users. Ideally positioned just off Highway 81 with outstanding visibility and high daily traffic counts, this location provides excellent exposure for a variety of businesses. The property has a strong history of commercial use, including a liquor store, professional office, and vape shop, making it well-suited for retail, office, service businesses, or future redevelopment. Multiple storefronts allow for rental income from several tenants or the opportunity to occupy one space while leasing the others. Ample parking, easy access, and a highly visible location make this a standout commercial investment in Chickasha. Offered at $599,000. Property Highlights: • Unit A – 1,500 SF (IFLY Tobacco & Vape) – Features a retail counter, display shelving, and storage area; currently leased with stable tenant. • Unit B – 540 SF (Dispensary) – Includes secure entry, interior display space, and restroom; perfect for small retail or office use. • Unit C – 1,280 SF (Liquor Store) – Open floor plan with shelving, checkout area, and storage. High-visibility location just off Highway 81 Excellent traffic exposure Ample parking Ideal for investors or owner-occupants Endless possibilities for retail, office, or service-based businesses This is an exceptional opportunity to own a versatile commercial property in one of Chickasha’s busiest commercial corridors. Schedule your private showing today. Interior pictures coming soon.

404 W Country Club Road, Chickasha

$189,000

3 Beds ⋅ 2 Baths ⋅ 1241224 MLS

Are you a porch sitter? This home offers a sweet front porch where you can sip your tea and wave to the neighbors! As you drive up, you'll love the extended drive that will easily accommodate 6 cars, or a couple of cars and a couple of toy as well as a double garage.! Upon entering, you'll see the front room which could be an office, sitting room, piano room, formal dining, or second living area. The spacious kitchen offers space for a table and chairs and/or a rolling island, which would look great! As a bonus, the seller has offered to leave the refrigerator. Off the kitchen, the laundry room is huge and has plenty of storage. The den area has a nice fireplace and wood look floors which are throughout the house. The three bedrooms are generously sized and both bathrooms offer walk/roll in showers. New windows have been installed within the past few years too! Come take a look at this one. The price is right and the location offers easy access to HE Bailey and US Hwy 81.

12 Morrow Drive, Chickasha

$178,000

3 Beds ⋅ 1 Baths ⋅ 1241120 MLS

Move-in ready and completely remodeled in 2024! This 3-bedroom, 1-bath brick home offers 1,283 sq. ft. of updated living space on a spacious corner lot in Chickasha. The renovation brought a fresh, modern feel throughout with updated flooring, paint, lighting, windows, kitchen cabinetry, granite countertops, and appliances installed in 2024. The kitchen offers plenty of cabinet and counter space with a clean, functional layout that opens easily into the main living areas. A brand-new roof will be installed, adding another major update for the next owner. Outside, enjoy a large yard with mature shade trees, covered front porch, double carport, attached garage, and plenty of room to enjoy the outdoors. With the major updates already completed, and a newly added $8000 privacy fence. This home offers the character of an established neighborhood with the convenience of a remodeled interior. Clean, updated, and ready for its next owner—schedule your showing today!

827 S 20th Avenue, Chickasha

$65,000

2 Beds ⋅ 1 Baths ⋅ 1240408 MLS

Calling all investors! This charming 840-square-foot home has already had the hard work started for you, with fresh paint, new flooring, and other interior updates that give it a clean, refreshed feel. Opportunities like this don't come around often at this price point. The home is currently tenant-occupied, making it an excellent investment opportunity with rental income already in place. Please allow a 24-hour notice for all showings so we can respect the tenant's schedule.

1117 W Pennsylvania Avenue, Chickasha

$149,900

2 Beds ⋅ 1 Baths ⋅ 1240990 MLS

Adorable and updated home in the sweet town of Chickasha! So many updates! Beautifully done and gorgeous finishes to this historical home! Brand new Floors throughout... lovely Acacia Wood floors in all the living spaces, new tile in the kitchen and bath, new marble counters and sink in kitchen, all new paint and fixtures and backsplash, some cabinetry is new as well. All brand-new appliances they also added a pantry space. Bathroom has been updated with new sink, toilet and vanity along with floors. Plumbing was brought upstairs for an all-in-one Washer/Dryer in the hallway, but facilities remain down in the basement as well, with a laundry chute from the hallway upstairs. Newly Painted inside and outside. Owner added the side drive for extra parking convenience. Two sweet porches on the front and the side of home. The garage is a single car space with a good-sized carport attached and well as a workshop space. This is a wonderful home for you to enjoy! with a full priced offer - the brand new fridge and washer/dryer combo can stay

1228 W Florida Avenue, Chickasha

$259,900

3 Beds ⋅ 2 Baths ⋅ 1240364 MLS

Y'all, this is the kind of place that feels like home the minute you pull into the driveway. Beautifully remodeled and sitting on over a quarter-acre lot, this spacious 1,985-square-foot home has all the fresh updates you've been looking for. Step inside to discover gorgeous designer-inspired color palettes, brand-new carpet, and fresh paint throughout, creating a bright, inviting space that's ready for you to make memories. Every room feels refreshed, blending timeless comfort with modern style. Outside, the oversized lot gives you plenty of room to entertain, garden, play, or simply enjoy peaceful evenings under the open sky. Whether you're hosting family cookouts or sipping your morning coffee on the patio, you'll appreciate the extra space and the sense of home this property offers. Beautifully updated, move-in ready, and full of charm, this is one you'll want to see for yourself. Come on home!

1904 S 21st Street, Chickasha

$230,000

3 Beds ⋅ 3 Baths ⋅ 1240281 MLS

Completely remodeled and move-in ready 3-bedroom, 2.5-bath home with new roof, siding, doors, windows, privacy fence, and more. Pull into the oversized driveway and follow the concrete sidewalk from the front porch around to the covered side and back porch, where you’ll find a fully fenced backyard with a gated entrance. LVP flooring flows through the main living areas & primary bedroom, with carpet in the secondary bedrooms and tile in the full bathrooms. The living room opens to a kitchen that features a custom blend of open shelving and traditional black cabinetry with gold hardware, quartz countertops, an undermount sink, breakfast bar with pendant lighting, walk-in pantry with lighting and custom stained shelving. New stainless-steel dishwasher, microwave, and stove. Just off the kitchen, the mudroom keeps everything organized with custom cabinetry, quartz countertops, a built-in bench with cubbies and hooks, a drying rack, and an oversized utility closet. A convenient half bath is tucked nearby across from the pantry, while a large storage closet behind the front door offers even more space. The primary suite is a true retreat with dual closets, including 1 walk-in closet, and a spacious bathroom featuring dual vanities, a soaking tub, tiled walk-in shower with bench, and a private water closet. The secondary bathroom is finished with a herringbone tile tub surround and black fixtures for a clean, timeless look. Recessed lighting throughout, ceiling fans in the bedrooms, custom cabinetry, and quality finishes make this home feel comfortable from the moment you walk in. Listing agent related to seller see attached disclaimer in supplements license #181843.

1828 W Idaho Avenue, Chickasha

$135,000

2 Beds ⋅ 1 Baths ⋅ 1240086 MLS

Welcome to the peace and privacy of this charming 2 bedroom, 1 bath brick home nestled in a beautiful rural setting surrounded by mature trees. Enjoy a large gated, fully fenced yard and two storage sheds, offering plenty of space for hobbies, pets, or outdoor living. Inside, you'll find new luxury vinyl plank flooring throughout the living areas and bathroom, fresh paint, a nice remodeled shower (2024), and the peace of mind a storm shelter safe room and a brand-new HVAC system installed in July 2026. This property is eligible for VA, FHA, and USDA financing, making homeownership more accessible to a variety of buyers. Whether you're looking for your first home, a place to downsize, or a peaceful country retreat, this one is a must see! Don't miss your opportunity and schedule your private showing today!

2707 County Street 2831 Street, Chickasha

$255,000

1239886 MLS

Bring Oklahoma history back to life on this beautiful 34-acre property just west of Chickasha! Rich with character and potential, this scenic tract offers the perfect setting to build your dream home while preserving the charm of an old Oklahoma homestead. The original homesite is ready for its next chapter, with mature trees, peaceful surroundings, and breathtaking countryside views that stretch for miles. Whether you envision a custom home, modern farmhouse, or weekend retreat, this property provides an incredible foundation to create something truly special. Designed with livestock in mind, the acreage is cross-fenced and includes an existing barn and cattle working pens, making it well-suited for horses, cattle, FFA or 4-H projects, or a small ranch operation. The gently rolling terrain provides excellent grazing while still offering multiple ideal building locations with panoramic views. Modern conveniences are already nearby with rural water available at the road (buyer must obtain application approval and complete connection requirements through the rural water provider) and OEC Fiber available at the road, making it easy to enjoy country living without sacrificing high-speed internet access. Whether you're searching for a homesite with room to roam, a small cattle operation, or a place where generations can build new memories, this property offers endless possibilities. Imagine watching Oklahoma sunsets from your front porch while bringing this historic homestead back to life. Opportunities like this are becoming increasingly difficult to find. Schedule your private showing today and discover the beauty, history, and potential this exceptional 34-acre property has to offer.

251 County Road 1370, Chickasha

$130,000

1238257 MLS

Here is a great opportunity to have a commercial building for a variety of uses. The front offers office space,. approx. 500 feet, with a front counter and waiting/display area. It does offer heat/cool, however, owner says the compressor has been removed. The back section offers approx. 2000 feet of "garage" type area with an overhead heater and restroom. There is an overhead door separating the two areas, an overhead door on the west side and also on the north side. The construction is cinder block with a metal roof. There is a nice sign on property for your business info. too!

202 W Iowa Avenue, Chickasha

$229,900

3 Beds ⋅ 2 Baths ⋅ 1239599 MLS

Step inside a luminous, open-plan sanctuary that feels expansive and inviting from the moment you walk through the front door. Gorgeous, harmonious color palettes blend soft neutrals with warm accents, creating an environment that’s both restful and uplifting—an ambiance best described as peaceful, purposeful, and full of possibility The chef-inspired kitchen shines with sleek quartz countertops, a generous island perfect for gathering, and high-end finishes that make every meal feel special. Large windows drench the living spaces in natural light, enhancing the serene tones throughout and blurring the lines between indoors and out. In the garage, tankless water heater, & an EV charger–ready space ensures you’re driving right into the future, while eco-conscious families will appreciate the forward-looking convenience. Situated just moments from Grady Memorial Hospital, Fort Sill, LSPI, HSI Sensing, Amazon, and Halliburton, your commute can mean more time at home and less behind the wheel. And with Chickasha Public Schools nearby, this home offers both community and comfort—where school mornings feel seamless and family dinners feel perfectly framed. Feel the pull of a fresh start in a place that’s made to grow into your greatest chapter yet. Experience the one you’ve been dreaming of—this home is waiting, and it won't last long.

908 Shady Meadow Way, Chickasha

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