Chickasha Homes with Guest Quarters Exterior features

Welcome to Chickasha, Oklahoma, a charming city nestled in Grady County, known for its warm community spirit and rich history. With a population of around 16,000, Chickasha boasts a vibrant downtown area filled with unique shops, delightful eateries, and a calendar full of events that celebrate local culture. The city is also home to the annual Chickasha Festival of Light, attracting visitors from all over to witness the dazzling holiday displays.

When it comes to real estate, Chickasha offers a unique selection of homes, including those with guest quarters. These properties are perfect for families seeking extra space for guests, in-laws, or even rental opportunities. Homes with guest quarters typically feature separate entrances, ensuring privacy while still being part of the main residence. This added versatility makes them an attractive option for those who value both comfort and convenience.

Exterior features of these homes often include beautifully landscaped yards, spacious patios, and outdoor living areas ideal for entertaining. Imagine hosting summer barbecues or enjoying peaceful evenings under the stars, all while having the flexibility of guest accommodations just steps away. With Chickasha's friendly atmosphere and a variety of recreational activities, including parks and nearby lakes, you'll find that these homes not only provide additional space but also enhance your lifestyle.

Whether you're a first-time homebuyer or looking to invest, Chickasha's real estate market offers a wealth of opportunities. Discover the charm of this delightful city and the potential of homes with guest quarters, where comfort and community come together harmoniously.

Newest Chickasha Homes with Guest Quarters Exterior features

$324,900

3 Beds ⋅ 3 Baths ⋅ 1234475 MLS

Main Residence: 3 Bed, 2.5 Bath, ~2,872 SQFT | Detached Guest House: 2 Bed, 1 Bath, ~850 SQFT. Located in the heart of Chickasha, this home puts you minutes from the town's best local dining, shopping, annual festivals, and classic small-town charm. Step into a remarkable piece of Chickasha history where timeless early-1900s architecture meets modern luxury. Meticulously renovated from top to bottom, the main residence combines preserved historic character with the ultimate peace of mind, boasting all-new PEX plumbing, updated electrical, energy-efficient Low-E windows, a tankless water heater, and a durable 50-year composition shingle roof. Original details have been lovingly restored throughout, including gorgeous pine floors, impressive 10-inch baseboards, vintage hardware, oversized pocket doors, and a grand staircase that creates an unforgettable first impression. At the heart of the home, a rare, one-of-a-kind triangular fireplace serves as an architectural masterpiece, providing warmth and ambiance to the living room, dining room, and luxurious primary suite simultaneously. The chef-inspired kitchen is flooded with natural light and showcases premium quartz countertops and custom cabinetry. Downstairs, the spacious primary retreat features a spa-like bathroom with designer tile, a soaking tub, a walk-in shower, and dual walk-in closets—each accented by its own elegant chandelier. Upstairs, you will find two additional bedrooms and a second versatile living space. Adding massive flexibility and value, the property includes a separate, fully remodeled 850-square-foot detached guest home featuring two bedrooms and one bathroom. This incredible bonus structure offers unmatched versatility, making it the perfect setup for multi-generational living, a private office/studio, a long-term guest cottage, or an income-producing asset. Properties with this level of historic detail, quality updates, and flexible square footage are a rare find—schedule your showing today!

1401 W Chickasha Avenue, Chickasha

$599,000

4 Beds ⋅ 3 Baths ⋅ 1223505 MLS

LOCATION. VISIBILITY. OPPORTUNITY. Positioned directly on Highway 81, this property offers incredible exposure in one of Chickasha’s busiest corridors. Whether you’re searching for your next home, investment property, or a site with potential for future use, this one checks the boxes. Properties with this kind of frontage and traffic don’t last. Not to mention, this home offers 4 bed, 2.5 bath with approximately 2,800 sq ft and has 14 rooms. Hard to find this combination of size, land, and accessibility! Perfect for buyers wanting room to live, grow, and invest. Properties like this don’t last—come see it before it’s gone!

2200 Highway 81, Chickasha

Start Your Search

Copyright © 2026 MLSOK, Inc. This information is believed to be accurate but is not guaranteed. Subject to verification by all parties. The listing information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. This data is copyrighted and may not be transmitted, retransmitted, copied, framed, repurposed, or altered in any way for any other site, individual and/or purpose without the express written permission of MLSOK, Inc. Information last updated on .