Grady County Homes with Chickasha School District

Welcome to Grady County, Oklahoma, a hidden gem known for its rich history, vibrant community, and scenic landscapes. Nestled in the heart of the state, Grady County is home to the charming city of Chickasha, where small-town charm meets modern living. With its friendly atmosphere and welcoming residents, Chickasha is the perfect place for families, professionals, and retirees alike.

One of the standout features of Chickasha is its highly regarded Chickasha School District. Families seeking quality education will find a variety of public schools that prioritize academic excellence and cater to the diverse needs of students. The district is known for its dedicated educators, innovative programs, and a strong sense of community involvement, making it an attractive option for those with school-aged children.

When it comes to real estate, Grady County offers a delightful array of homes that cater to various lifestyles and budgets. From charming historic houses to modern family homes, there’s something for everyone. Many properties are conveniently located near schools, parks, and local amenities, ensuring that you and your family can enjoy everything this vibrant community has to offer.

Living in Grady County means embracing a lifestyle rich in outdoor activities, local festivals, and a close-knit community feel. Whether you’re exploring the picturesque landscapes or participating in local events, you’ll quickly discover why so many people choose to call Chickasha home. Come and experience the warmth and hospitality of Grady County—your dream home awaits!

Newest Grady County Homes with Chickasha School District

$449,500

4 Beds ⋅ 4 Baths ⋅ 1256575 MLS

Welcome to 416 Fieldcrest Drive, a beautifully maintained, custom-built brick estate offering 3,365 square feet of luxurious living space on a generous 0.45-acre lot in Chickasha with desirable circle drive. Combining classic traditional architecture with premium finishes, this 4-bedroom, 3.5-bathroom home is meticulously designed for both sophisticated entertaining and comfortable everyday living. As you step inside, you are greeted by elegant arched doorways that lead into a spacious, light-filled layout. The gourmet kitchen serves as the heart of the home, crafted with entertaining in mind and offering plenty of room for family gatherings. The expansive primary suite provides a true sanctuary, featuring its own cozy, private fireplace and an elegant en-suite bathroom. On the other side of the home, two oversized bedrooms are seamlessly connected by a convenient Jack-and-Jill bathroom, perfect for children or guests. A major highlight of this property is the massive, custom addition that serves as a versatile bonus living area or ultimate media room. Complete with a fourth bedroom and its own dedicated full bathroom, this wing is ideal for a multi-generational setup, a home office, or private guest quarters. The luxury extends outdoors into your own private backyard paradise. The large, fully covered patio is an entertainer’s dream, boasting a full outdoor kitchen, a stunning fireplace for chilly evenings, and a massive yard with endless possibilities for a pool, garden, or play area. Complete with a spacious three-car garage and unmatched curb appeal, this Chickasha gem truly has it all. Don’t miss your chance to own this exceptional property. Schedule your private tour today to experience this magnificent home in person.

416 Fieldcrest Drive, Chickasha

$202,000

4 Beds ⋅ 2 Baths ⋅ 1257431 MLS

Welcome to this beautifully updated and spacious home offering 4 bedrooms, 2 full bathrooms, and two separate living areas—perfect for both relaxing and entertaining. This property also features a versatile studio space, ideal for a home office, guest suite, or creative workspace. The home has been fully updated with newer vinyl flooring throughout and a modernized kitchen complete with stylish cabinetry. Both bathrooms have been thoughtfully renovated, providing a fresh and contemporary feel. Enjoy peace of mind with major system upgrades already completed, including a 2-year-old roof, updated HVAC, plumbing, and electrical systems. Additional highlights include a convenient 2-car garage with a carport addition at the back of the home, offering extra parking and functionality. This move-in-ready home combines space, comfort, and modern updates—don’t miss your opportunity to make it yours! Seller selling in "As-Is" condition and will only qualify for conventional or cash offers

1427 W Chickasha Avenue, Chickasha

$220,000

4 Beds ⋅ 2 Baths ⋅ 1256545 MLS

Santa’s sleigh will have a safe place to land this year, because 1710 Louisiana has a brand new roof. It went on in October 2026 with a full tear-off, ice & water shield, new shingles, new flashing and edge metal, and sharp new black gutters and downspouts. It also comes with a five-year labor warranty, so the hard part is already done. Inside, this 1961 two-story has 2,005 sq ft of living space with 4 bedrooms, 2 baths, and two living areas, so there’s room for the tree, the presents, and the relatives who “just stopped by.” The bonus is the Florida room. It’s heated and cooled with the rest of the house, so you can sip cocoa there in December and sweet tea in July. The kitchen is ready for cookie season. It has granite countertops, a 50/50 stainless sink, and freshly painted cabinets finished in a durable pro-grade urethane. Holiday baking just got a lot more stylish. Outside, there’s even more: A garage, plus a small shop for Santa’s workshop (or your own) A large backyard with a dog pen for your furry elves A 30x40 concrete pad with alley access for the RV, the boat, or one serious light display A concrete shelter room in the basement for Oklahoma’s not-so-merry weather And then there’s the location. You’re in Chickasha, home of the famous Festival of Light, where millions of twinkling lights make the whole town glow every holiday season. Every drive home will feel like a Christmas card. Schedule your showing before someone else unwraps this one first! ??

1710 W Louisiana Avenue, Chickasha

$330,000

4 Beds ⋅ 2 Baths ⋅ 1256860 MLS

Welcome to 109 St. Charles Place in Chickasha! This spacious 4-bedroom, 2-bathroom home offers plenty of room to spread out and enjoy! Inside, you'll find generous living space with plenty of room for gathering with family and friends. Step outside to enjoy the backyard and covered porch, perfect for entertaining, relaxing, or enjoying those beautiful Oklahoma evenings. Conveniently located just off Country Club Road, close to the golf course, shopping, dining, and other local amenities, this home offers both comfort and convenience in the Chickasha School District. Whether you're looking for room to grow, space to entertain, or a place to call home, this property is one you won't want to miss! Don't wait to make your move! Schedule your private showing today and see everything this home has to offer. Your next home could be waiting for you at 109 St. Charles Place!

109 Saint Charles Place, Chickasha

$249,900

4 Beds ⋅ 3 Baths ⋅ 1257222 MLS

Spacious, beautifully remodeled 4-bedroom, 3-bath home offering 2,237 square feet of versatile living space conveniently located near USAO in Chickasha! This property features two living areas, two kitchens, and a flexible layout with excellent potential for multi-generational living or rental income. Numerous updates include updated plumbing, mostly new windows, new vinyl flooring and carpet, fresh interior paint and some electrical improvements. It has updated fixtures, the main kitchen is equipped with high-quality stainless-steel appliances, while the second kitchen provides additional convenience and flexibility. Other features include central heat and air, supplemental window units in the back living area, two water heaters (one is new), a Florida room, and an open patio. Situated on a large lot with alley access, the property offers both a single-car attached garage and a single-car detached garage that could provide private parking for a potential tenant. With its extensive updates, generous living space, and unique possibilities for additional income, this property offers a valuable opportunity for homeowners!

2007 S 14th Street, Chickasha

$139,999

3 Beds ⋅ 2 Baths ⋅ 1257162 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

$154,900

3 Beds ⋅ 2 Baths ⋅ 1256670 MLS

Welcome to this charming 3-bedroom, 1.5-bath home offering 1,416 square feet of character and thoughtful updates! Featuring original hardwood floors, a distinctive red metal roof, and a delightful galley-style kitchen with quartz countertops, farmhouse sink, open shelving, and stylish finishes. Additional highlights include remodeled bathrooms, central heat and air, and a spacious walkable attic offering convenient storage potential. Outside, enjoy a generously sized fenced backyard with room for gardening, entertaining, or relaxing. With its cheerful curb appeal, timeless charm, and modern touches, this home has so much to offer. Schedule your showing today!

1616 S 14th Street, Chickasha

$180,000

2 Beds ⋅ 4 Baths ⋅ 1256595 MLS

A rare gem in Chickasha! Are you looking for a property that offers more than just a place to call home? This one is full of possibilities! Featuring 2 bedrooms, 2 bathrooms, and a BONUS den area, this recently updated home has plenty to offer. You'll notice the beautiful oak tree cabinets with upgraded features, adding warmth and character throughout the home. But that's not all! Out back, you will find a shop with overhead door and convenient access from the back of the lot, making it perfect for projects, hobbies, extra workspace, or all your storage needs. With plenty of room to spread out and make it your own, this property is truly a unique find!

201 N 17th Street, Chickasha

$159,900

3 Beds ⋅ 2 Baths ⋅ 1255663 MLS

Welcome home to a charming 3-bedroom, 1.5-bath home nestled in an established neighborhood where character and comfort come together! This home has some wonderful updates already taken care of, including a newer roof and an updated central heat and air unit, giving you a little extra peace of mind. But let's talk about those floors! The beautiful wood flooring is simply breathtaking and brings warmth, character, and timeless charm. Whether you're looking for a place to put down roots, make memories, or simply enjoy the comforts of home, this one is full of possibilities. She's got good bones, beautiful character, and plenty of heart. Don't let this sweet home pass you by!

209 Meadowdale Drive, Chickasha

$173,500

3 Beds ⋅ 2 Baths ⋅ 1256391 MLS

Welcome home to this well-maintained property located on a corner lot in Chickasha! This home offers several valuable recent updates, including a brand-new roof installed just two months ago, a hot water tank approximately two years old, new HVAC unit and furnace and new storm doors. The garage also features new windows. Outside, you’ll appreciate the spacious backyard with plenty of room for entertaining, gardening, pets, or enjoying the outdoors. Pride of ownership is evident throughout this property, making it a great opportunity for its next owner. Schedule your private showing today!

2002 W Alabama Avenue, Chickasha

$54,900

2 Beds ⋅ 1 Baths ⋅ 1256030 MLS

Opportunity awaits with this 2-bedroom, 1-bath home located on a corner lot in Chickasha! The home features wood flooring, central heat and air, and a functional layout. The property also includes a detached one-car garage and a carport, providing additional parking and storage options. With its corner lot location and existing features, this property offers an opportunity to make it your own. Conveniently located in Chickasha with potential for a variety of possibilities!

1427 S 14th Street, Chickasha

$195,000

3 Beds ⋅ 2 Baths ⋅ 1247315 MLS

Welcome to this beautiful, move-in-ready 3-bedroom, 2-bathroom home located in the desirable Sleepy Hollow Addition! Built in 2021, this home offers modern style and comfortable living with a thoughtfully designed layout. The kitchen features stainless steel appliances and beautiful countertops, creating an inviting space for cooking and entertaining. With its newer construction and appealing finishes, this home is ready for you to move in and make it your own. Don't miss the opportunity to make this wonderful home yours!

1001 Tarry Town Drive, Chickasha

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