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1523 Stewart Drive, Chickasha
$2,750,000
1209216 MLS
Large, high-visibility retail building located just off the heavily traveled 4th Street corridor in Chickasha. A Primary commercial business area. Currently operating as a liquor store, this property offers an exceptional opportunity for continued operation or redevelopment into a wide range of retail or commercial uses including marketplace, grocery, convenience, specialty retail, or showroom offer over 12,300 sq ft of retail space. The building features expansive double-pane storefront windows, providing excellent natural light and outstanding exposure for branding, signage, and product displays. Inside, the property is designed to support high-volume retail operations with 10 central air and/or gas HVAC units, 3-phase electrical service, and approximately 1,100 square feet of refrigerated cooler space. A massive paved parking lot provides approximately 70 parking spaces, including ADA-accessible parking, making it ideal for heavy customer traffic, delivery access, and peak retail hours. This property offers strong infrastructure, outstanding visibility, and flexible use potential in one of Chickasha’s most active commercial areas — an excellent opportunity for owner-operators or investors seeking a high-traffic retail location.

1523 Stewart Drive, Chickasha

1601 Highway 62, Chickasha
$695,000
3 Beds ⋅ 3 Baths ⋅ 1249921 MLS
Where timeless character meets modern comfort! Situated on 25 fenced acres, this beautifully renovated 1940 home offers 3 bedrooms, 3 bathrooms, abundant natural light, and incredible views of the surrounding countryside. Thoughtfully modernized from top to bottom, the home retains the charm that makes it special, including beautifully preserved original wood floors, while incorporating the updates today's buyers expect. The extensive renovation includes a new kitchen, updated bathrooms, new appliances, new upstairs A/C, and spray foam insulation throughout the home for improved efficiency and comfort. Large windows fill the interior with natural light and showcase the peaceful rural setting. The spacious upstairs family area offers tremendous flexibility and could easily be reconfigured to create additional bedrooms, giving the home the potential for a 4 or even 5 bedroom layout. A unique bonus room provides the perfect space for a craft room, playroom, hobby space, or home office. Outside, the 25 acres are fenced and feature a pond along with multiple outbuildings that add both character and functionality. An original milking parlor is a reminder of the property's agricultural history, while the modern 30x50 shop provides excellent space for equipment, projects, storage, or recreational toys. With highway frontage for convenient access yet a homesite that maintains a quiet, private, rural feel, this property offers a rare combination of accessibility and country living. Renovated with exceptional attention to detail and a commitment to preserving its original character, this is not simply an updated farmhouse—it's a property where the hard work has already been done. Move in, spread out, and enjoy 25 acres of Oklahoma country living.

1601 Highway 62, Chickasha

2439 Friend Circle, Chickasha
$582,000
3 Beds ⋅ 3 Baths ⋅ 1212114 MLS
Located in the brand new Falcon Ridge addition, this well-appointed home features a rock and brick exterior with tongue-and-groove detailing under the porches. The open-concept layout offers 3 bedrooms, 2 full baths, and 1 half bath. The kitchen includes abundant storage, a stained island with detailed woodwork, quartzite countertops, a gas range with custom hood, and a large window over the sink. Wood-look tile runs throughout main living areas, with patterned tile in the laundry and baths, quartz countertops in bathrooms, and carpeted bedrooms. The primary suite features double shower heads, stained cabinetry, and built-in dressers closets. Covered back patio is set up for an outdoor kitchen and includes a fireplace—ideal for entertaining. Convenient location with easy Turnpike access.

2439 Friend Circle, Chickasha

404 W Country Club Road, Chickasha
$559,000
1241240 MLS
Prime Commercial Opportunity right off of Busy Highway 81! Buy them all or LEASE a unit, 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

307 S 7th Street, Chickasha
$550,000
1223767 MLS
Tastefully remodeled commercial building located at 307 S 7th Street in Chickasha. Currently leased on a month-to-month basis, offering immediate income potential or flexibility for an owner-user. This ADA-compliant property features a functional layout including a spacious conference room, multiple private offices, reception area, breakroom, and a large group workspace. Additional rooms are currently utilized as playrooms and visitation areas, providing versatility for a variety of business uses. The property also includes a laundry room, multiple storage areas, and a comfortable lounge space. Renovated approximately five years ago, the building is well-maintained and equipped with three HVAC units for efficient climate control. Ample parking and easy access make this an excellent opportunity for office, medical, counseling, or service-based businesses.

307 S 7th Street, Chickasha

3508 Scissortail Lane, Chickasha
$499,900
4 Beds ⋅ 3 Baths ⋅ 1204258 MLS
Giant price reduction!! NEW CONSTRUCTION in the Beautiful Exclusive Gated Community of Redbud Ridge in Chickasha! Enter his Beautiful home from the covered front porch and through the beautiful double metal and glass arched front doors, this home features 4 bedrooms, 2 1/2 bathrooms and a 3 car garage a large kitchen with custom cabinets, stainless steel appliances, double ovens, smooth top cooktop, microwave mounted in a cabinet off the counter top, large island with a waterfall quarts counter top, soft close drawers, motion lighting under the cabinets to light your way at night and has several pullouts for spices and trash receptacles. The Primary bedroom features an en suite bathroom with a soaker tub, double sinks plus a separate make up area, stand alone shower and a large walk in closet with custom drawers. Two of the bedrooms are located on the opposite side of the home from the Primary and have a full connecting bath to share, the 4th bedroom could be used as an office and has a half bath next to it. The living room is large and feature arches into the kitchen and dining area and features a lovely modern electric fireplace. Large laundry room with sink, folding area on the countertop and lots of cabinet space, enough room for a stand up freezer or extra refrigerator and is conveniently across from the hall from the kitchen. The covered front porch features a set of arched double front doors. The covered back porch is large and had lots of room for enjoying cooking out or outdoor living. This will be an energy efficient home and includes spray foam insulation, total electric and has a heat pump. Comes with a 1 year builders warranty. Come be part of this exclusive gated community!

3508 Scissortail Lane, Chickasha

404 W Pikes Peak Road, Chickasha
$499,000
1236191 MLS
Want to buy? OK! Want to lease? OK! Either option works. Lease price is 3500.00/mo for one year lease. Opportunity awaits at this location! This versitile property offers two metal buildings, one is a 40x40 with 2 office spaces, restroom and conference area. There is a walk thru door to the fenced yard as well as an 8' overhead door. The second building is 30x40 and is only accessible from the fenced yard. It has a walk thru door and three 8' overhead doors. It is insulated and has 70 amp power. The yard has 6 outlets for diesel block heater plug in capability. There is 8" of rock with about 4" of crushed gravel on top of that to ensure usage for trucks. A 6' fence with barbed wire surrounds the property for security. The property has been used for utility companies, oil and gas companies, etc. If more property is needed, there are a few additional acres behind it that could be purchased with this property. Providers are: internet-Hillary water-Ninnekah gas-Summit (Heat and hot water) septic

404 W Pikes Peak Road, Chickasha

626 W Kansas Avenue, Chickasha
$489,000
1252240 MLS
Commercial property in Chickasha. This well-established brick commercial property offers approximately 4000 mol, square feet, including an approximately 900-square-foot enclosed breezeway, and is currently configured for multiple tenants and professional service businesses. HVAC on roof purchased in 2021. The versatile interior offers a combination of 4 private offices and 9 treatment rooms, reception and waiting areas, larger open treatment/work spaces, storage, restrooms, and a laundry area with sink. Built-in cabinetry and sinks in portions of the building add functionality for medical, therapy, wellness, or other professional uses. The enclosed breezeway provides additional usable space and natural light while connecting areas of the building. Additional features include metal-stud construction, rooftop HVAC, six exits, rear entry with loading access, and convenient on-site parking. The building’s multiple entrances and flexible floor plan allow individual businesses to operate within their own spaces while remaining under one roof. Multiple tenants are currently in place, providing an attractive opportunity for an investor seeking an established income-producing property. The configuration also offers future flexibility for an owner-user who may wish to occupy a portion of the building while continuing to lease the remaining spaces. With its distinctive brick exterior, highly visible commercial presence, established tenant configuration, and adaptable interior, 626 W. Kansas Ave. offers tremendous potential for continued investment use, professional offices, state offices, medical or therapy services, wellness businesses, or a variety of other commercial operations. Property is being sold as an entire building. Please do not disturb tenants. Shown by appointment only.

626 W Kansas Avenue, Chickasha

416 Fieldcrest Drive, Chickasha
$449,999
4 Beds ⋅ 4 Baths ⋅ 1217923 MLS
This beautiful custom-built 4-bedroom, 3.1-bathroom home is loaded with amenities! It features a spacious kitchen perfect for cooking and entertaining, along with a large primary suite complete with a cozy fireplace and an expansive primary bathroom. This home offers two oversized bedrooms with a Jack and Jill bathroom. The real gem of this home is the large addition that offers an extra living area or "Man Cave", a fourth bedroom and a large full bathroom. When you step outside you are greeted with a large covered patio with an outdoor kitchen with a stunning fireplace which is ideal for relaxing or hosting guests. A perfect home for entertaining and comfortable living in a beautiful and established neighborhood.

416 Fieldcrest Drive, Chickasha

2758 County Street 2780, Chickasha
$439,000
2 Beds ⋅ 2 Baths ⋅ 1245006 MLS
78 Acres of Scenic Bliss – Endless Possibilities Await! Discover the perfect blend of serenity and potential with this stunning 78-acre property just minutes from Chickasha and within the desirable Pioneer School District. Featuring breathtaking views, rolling hills, and open skies, this land offers a rare opportunity to embrace country living at its finest. Whether you're dreaming of building your custom dream home or looking for a peaceful retreat, this property delivers. A well-maintained mobile home is already in place, ideal for comfortable living while you plan your future build or use as a weekend getaway. Enjoy the quiet, tranquil surroundings with ample space for livestock, recreation, farming, or simply soaking in the natural beauty. With easy access to town and schools, yet tucked away from the hustle and bustle, this property truly offers the best of both worlds. Don’t miss your chance to own a slice of Oklahoma paradise – the possibilities are endless.

2758 County Street 2780, Chickasha

215 Kansas Avenue, 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

3812 W Hickorystick Drive, Chickasha
$414,647
4 Beds ⋅ 3 Baths ⋅ 1246499 MLS
Introducing the stunning Aaliyah Elite — an exceptional 2,401 square-foot home designed to elevate everyday living with elegance, comfort, and modern sophistication. Nestled within Sleepy Hollow, one of Chickasha’s most highly sought-after communities, this beautifully crafted home features 4 spacious bedrooms, 2.5 luxurious bathrooms, the versatile space is perfectly suited for remote work, study space & everyday organization. The private owner’s retreat provides a peaceful escape with a spa-inspired ensuite bath and generous closet space, while the additional bedrooms offer flexibility. Step outside to the beautifully covered back patio overlooking a huge homesite, creating the perfect outdoor oasis for relaxing evenings, gatherings, and enjoying Oklahoma sunsets. Conveniently located just minutes from the turnpike, the Aaliyah Elite offers quick access to major employers including Cimarron Trailers, Stanley Systems, HSI Sensing, LSPI, and Fort Sill, making this home the perfect blend of luxury, convenience, and lifestyle. Discover the elegance of the Aaliyah Elite — where sophisticated design meets everyday functionality in the heart of Chickasha.

3812 W Hickorystick Drive, Chickasha

3804 W Hickorystick Drive, Chickasha
$410,745
4 Beds ⋅ 3 Baths ⋅ 1246497 MLS
Meet the Chelsea in the highly sought after Sleepy Hollow community! We know you are going to fall in love with the thoughtful design and unrivaled expanse of the Chelsea! This brand-new, energy-efficient beauty is nestled in one of the area’s most desirable communities, presenting an extraordinary 4-bedroom, plus flex space, 2.5-bath layout, and a massive 3-car garage—all meticulously crafted to maximize comfort, style, and every aspect of modern living. Step inside and you’ll be greeted by dramatic, soaring ceilings that make the vast, open living spaces feel light, airy, and truly magnificent. The heart of the home—the kitchen—features a sleek quartz island that perfectly balances modern design with timeless appeal, creating an ideal central hub for large gatherings and effortless entertaining. Significantly expanding your usable space, the large covered back patio becomes a natural outdoor living room, perfect for enjoying the outdoors. You’ll enjoy total peace of mind knowing this home is built for the future. It includes a high-efficiency HVAC system, an EV charger, a tankless water heater, and a valuable 10-year structural warranty. 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 a fantastic community right at your doorstep. Reserve this brand-new, energy-efficient home today before it is gone like the others! This isn't just a place to live—it's a sprawling haven designed to plant roots, gather, and make memories for years to come.

3804 W Hickorystick Drive, Chickasha

1921 State Highway 92, Chickasha
$383,900
3 Beds ⋅ 2 Baths ⋅ 1245691 MLS
This property offers a great combination of comfort, functionality, and space, featuring 3 bedrooms and 2 bathrooms along with several valuable updates. The home has a new roof, new A/C unit, fresh paint, and updated windows, providing peace of mind and a refreshed look. A major highlight is the impressive 30x40 shop, featuring spray foam insulation and plenty of room for a workshop, vehicles, equipment, hobbies, or additional storage. The property also includes a 54' Conex building for even more secure storage, plus a small shop behind the house for added convenience. Outside, the garden area provides space for gardening, outdoor projects, or creating your own peaceful retreat. With multiple outbuildings and generous outdoor space, there is plenty of flexibility for work, storage, hobbies, and everyday living. Inside, the fresh paint and updated windows create a clean and inviting atmosphere, while the new roof and A/C provide important recent improvements. The 3-bedroom, 2-bathroom layout offers comfortable living space for a variety of needs. Located along State Highway 92, this property offers convenient access while providing the space and features that make it a versatile place to call home. With a new roof, new A/C, updated windows, fresh paint, a 30x40 shop, 54' Conex building, additional small shop, and garden area, 1921 State Highway 92 is ready for its next owner!

1921 State Highway 92, Chickasha

3808 W Hickorystick Drive, Chickasha
$380,411
4 Beds ⋅ 3 Baths ⋅ 1246495 MLS
Welcome to refined living in the highly sought after Sleepy Hollow community! This stunning 2,028 square-foot home seamlessly blends elegance, comfort, and modern functionality, offering 4 spacious bedrooms, 2.5 beautifully appointed bathrooms, and a thoughtfully designed tech area perfect for working from home, studying, or managing everyday life with ease. The gourmet kitchen serves as the heart of the home, showcasing stylish cabinetry, premium finishes, abundant counter space, and an inviting layout ideal for gatherings. Retreat to the serene owner’s suite featuring a spa-inspired bath and generous closet space, while the additional bedrooms provide flexibility. Step outside to enjoy the beautifully covered back patio overlooking an oversized homesite — the perfect setting for relaxing evenings, outdoor dining, and weekend entertaining. Ideally located just minutes from the turnpike, this exceptional home offers convenient access to major employers including Cimarron Trailers, Stanley Systems, HSI Sensing, LSPI, and Fort Sill, you'll have both convenience and an elevated lifestyle. Experience the perfect combination of sophistication, space, and location — a place you’ll be proud to call home.

3808 W Hickorystick Drive, Chickasha

3310 Pondridge Road, Chickasha
$380,000
3 Beds ⋅ 3 Baths ⋅ 1243953 MLS
Welcome to 3310 Pondridge Road, where peaceful waterfront living meets plenty of space to call home. This 3-bedroom, 2.1 bath home offers approximately 2,587 square feet of living space in the established Conrad Heights neighborhood of Chickasha. Built in 1992, the home features a brick exterior, fireplace, and a spacious layout with plenty of potential to make it your own. The highlight is out back—a large covered deck overlooking the neighborhood pond, creating a great setting for morning coffee, evening sunsets, entertaining, or simply enjoying the water and wildlife. The property sits on approximately 0.28 acres and offers a rare combination of an established neighborhood setting with a relaxing waterfront atmosphere. With its generous square footage, three full bathrooms, and one-of-a-kind backyard view, this Chickasha property is ready for its next owner. Come see the view from the back deck for yourself!

3310 Pondridge Road, Chickasha

2293 County Street 2814, Chickasha
$348,500
3 Beds ⋅ 3 Baths ⋅ 1236267 MLS
Interest rates a concern? Seller is willing to pay for up to two points toward rate buydown!! Need space? Here it is!! This roomy home not only offers space inside, but outside too! Located in the Rock Creek Addition on the west side of town, this home offers elbow room for spreading out, but it is a neighborhood for taking walks and seeing friends. What do we love about this home? *location...so close to town, yet feels rural *a neighborhood where people can spread out *just outside of city limits which means fewer limitations/rules *established shade trees-wonderful for a tire swing or for climbing *set up for multi generational space or potential rental possibility The street level offers the main bedroom and living/dining areas with an office/playroom with a wall of windows and laundry area, and the walk out basement offers more bedrooms with a full bathroom, bar area, fireplace and another laundry area. The backyard offers a nice patio and fenced yard with an outbuilding for storing extra belongings. If you're ready to spread out, but don't want to feel isolated, this is the home for you!

2293 County Street 2814, Chickasha

3310 S 23rd, 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

3316 S 23rd, 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

3308 S 23rd Unit 1, Chickasha
$345,000
4 Beds ⋅ 1216683 MLS
Stylish, Low-Maintenance Living in the Heart of Chickasha Discover comfort and modern design in this beautifully constructed 2-bedroom, 2-bath duplex nestled in a quiet Chickasha neighborhood. Thoughtfully designed with both style and functionality in mind, this home offers an inviting space that feels bright, open, and effortlessly livable. Step inside to a light-filled open-concept layout where the living, dining, and kitchen areas connect seamlessly—creating the perfect setting for entertaining friends or enjoying a relaxing night at home. Large windows enhance the airy feel, while the smart floor plan maximizes every square foot. The kitchen is a true highlight, featuring sleek granite countertops, stainless-steel appliances, abundant cabinetry, and clean, contemporary finishes. Even better, this home comes fully equipped with a complete appliance package—including refrigerator, dishwasher, gas range, microwave, washer, and dryer—so you can move in with ease from day one. The spacious primary suite serves as a private retreat with its own ensuite bath and generous closet space. A second bedroom and full bathroom provide versatility for guests, a home office, or additional household members. Outside, enjoy your fully fenced backyard—perfect for pets, gardening, weekend gatherings, or simply unwinding in your own private outdoor space. Conveniently located near schools, parks, shopping, and dining, this property offers the charm of small-town living with everyday essentials just minutes away. If you’re looking for modern comfort with minimal maintenance, this Chickasha gem is ready to welcome you home.

3308 S 23rd Unit 1, Chickasha

116 Caulder Drive, 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

CS 2860 Unit Tract C, Chickasha
$315,000
1235799 MLS
Here is a beautiful opportunity to own land just outside of Chickasha. Property is in the Friend School District and then Chickasha or Amber. There was a home on the property years ago, well and septic condition is unknown. Property offers an abundance of trees, bermuda grass. This is a good mixture of open terraced terrain and thick trees and brush. Just minutes from Chickasha, and with easy access to I-44 and Highway 62, you'll be hard pressed to find a parcel this large so close to town. Acreage and easement and tax information to be verified by buyer. This will be a pacel split off of a larger parcel. Survey will be completed upon contract acceptance. This is parcel C, on map. Actual acreage to be determined by survey. (Photos are from entire acreage being sold. Other mls #'s are 1235803, 1235790, 1235787)

CS 2860 Unit Tract C, Chickasha

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