Chickasha Real Estate

Welcome to Chickasha, Oklahoma – a hidden gem nestled in the heart of Grady County! This charming city, with a population of around 16,000, boasts a rich history and a vibrant community spirit that makes it an ideal place to call home. Known for its friendly atmosphere and strong sense of community, Chickasha offers a delightful blend of small-town charm and modern conveniences.

Chickasha is renowned for its annual events, including the popular Chickasha Festival of Light, which transforms the city into a winter wonderland each holiday season. The city is also home to the historic Chickasha Depot, a beautifully restored train station that reflects the area’s rich railroad history. For those who enjoy the outdoors, the nearby Washita River and Lake Chickasha provide ample opportunities for fishing, hiking, and picnicking.

Education is a priority in Chickasha, with a strong public school system and access to higher education through the University of Science and Arts of Oklahoma. The city is well-connected, with easy access to major highways, making it a convenient hub for commuters traveling to nearby cities like Oklahoma City.

With a diverse range of housing options, from charming historic homes to modern developments, Chickasha is perfect for families, retirees, and everyone in between. Whether you’re looking to settle down or simply visit, Chickasha invites you to discover its warm hospitality and vibrant community. Come explore all that this wonderful city has to offer – you may just find your perfect place to call home!

Newest Listings in Chickasha

$79,900

2 Beds ⋅ 2 Baths ⋅ 1242017 MLS

Situated on approximately 5 acres in the Pioneer School District, this 2-bedroom, 1.1-bath home offers a unique opportunity to create the country retreat you've been dreaming of. Inside, you'll find two spacious living areas and two dining areas, providing a flexible layout with plenty of room to reimagine the space. The acreage offers endless possibilities for gardening, outdoor recreation, livestock, or simply enjoying the peaceful rural setting. Whether you're looking for a weekend getaway, a place to put your personal touch, or the chance to build your own private oasis, this property is ready for its next chapter. Conveniently located with easy access to Chickasha while still offering the privacy and space that acreage living provides.

531 County Road 1390 Road, Chickasha

$164,900

3 Beds ⋅ 2 Baths ⋅ 1240317 MLS

Well now, if you’ve been waitin’ on a place that feels brand-new but still knows how to feel like home, this one just might be singin’ your song. This beautiful 3-bedroom, 1.1-bath home has been completely remodeled from top to bottom — we’re talkin’ a new roof, new windows, central heat and air, a new water heater, fresh paint, new flooring... the list just keeps on goin’. Tucked right into the heart of Chickasha — yes, Christmas Town itself — this home shines just as bright on the outside as it does on the inside. It’s got all the charm, all the updates, and all the heart you’ve been lookin’ for. So don’t wait around hummin’ about it — call today and schedule your own private showing before someone else falls in love first.

917 W Colorado Avenue, Chickasha

$35,000

1241345 MLS

Great property to build a warehouse or use as parking for large equipment or vehicles. Property may be located in a flood area.

0000 0000, Chickasha

$140,000

3 Beds ⋅ 2 Baths ⋅ 1241620 MLS

Rare find in Chickasha, a full acre backing up to shannon springs lake! This 3-bedroom, 2-bath home sits on a spacious lot backing directly to the lake, offering privacy and a peaceful setting rarely available at this price point. Full of character, the home retains original finishes, a large sunroom, and vintage detail throughout, appealing to buyers who appreciate craftsmanship you won't find in new construction. A separate living area/workshop adds incredible flexibility, use it as a studio, hobby shop, guest quarters, or extra storage. Enjoy lake views right from your own backyard. Being sold as-is, this is a great opportunity for buyers ready to bring their vision and make it their own. Don't miss this one-of-a-kind property!

3409 S 4th Street, 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

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