Chickasha Homes with Guest Quarters Exterior features

Welcome to Chickasha, Oklahoma—a charming city nestled in the heart of Grady County, where small-town hospitality meets vibrant community spirit. Known for its rich history and friendly atmosphere, Chickasha offers a delightful blend of modern amenities and nostalgic charm. With a population of around 16,000, this city is perfect for those seeking a close-knit community while still enjoying access to urban conveniences.

Chickasha is famous for its annual events, including the Chickasha Festival of Light, where the city transforms into a winter wonderland that attracts visitors from all over. The city is also home to a variety of parks, shops, and restaurants, providing ample opportunities for recreation and relaxation. Nature enthusiasts will appreciate the nearby Lake Chickasha, perfect for fishing, boating, and picnicking.

For those looking to invest in real estate, Chickasha features a variety of homes, including those with guest quarters—an ideal option for families, visitors, or even as rental opportunities. These homes often boast charming exteriors, complete with well-manicured lawns, spacious patios, and inviting entryways. The guest quarters provide a perfect retreat for guests or can serve as a private office or creative space.

Imagine hosting family gatherings or entertaining friends in your beautiful backyard, while your guests enjoy their own cozy space just steps away. With a range of styles and sizes available, homes with guest quarters in Chickasha offer flexibility and comfort, making them a fantastic choice for any homeowner. Discover the warmth and potential of Chickasha today—your dream home awaits!

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

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