Chickasha, OK Homes for Sale under $500,000

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  /39

  $294,400

  $26K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,369 Sq Ft

  2824 Nichols Rd, Chickasha, OK 73018

  Step back in time with this one of a kind find in a neighborhood full of story book charm, character & timeless curb appeal. Tucked away in a beloved area of Chickasha, on a winding cul-de sac street, this original home features woodwork, cabinetry & built-ins from an era known for craftsmanship. As you approach the front door, you’re greeted by 2 large concrete planters and a granite covered

  Tina Curtis eXp Realty, LLC

  2824 Nichols Rd, Chickasha, OK 73018
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  /16

  $232,000

  $3K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft

  2115 Ridge Way, Chickasha, OK 73018

  Discover the epitome of contemporary living at 2115 NONE Ridge Way ST, Chickasha OK 73018. This newly constructed single-family residence, built in 2024, offers a fresh start and the promise of a truly inspired lifestyle. With four thoughtfully designed bedrooms, this home provides ample personal space and flexibility, accommodating diverse needs from tranquil retreats to vibrant home offices.

  Renee Stallings Century 21 Mosley

  2115 Ridge Way, Chickasha, OK 73018
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  $211,000

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft

  Duxbury Plan at Sleepy Hollow, Chickasha, OK 73018

  Colony Fine Homes Builder

  926 Hudson Road St Unit 36916248, Chickasha, OK 73018
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  /4

  $410,745

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,221 Sq Ft

  3804 Hickory Stick Dr, Chickasha, OK 73018

  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

  John Burris Central Oklahoma Real Estate

  3804 Hickory Stick Dr, Chickasha, OK 73018
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  /4

  $380,411

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,030 Sq Ft

  3808 Hickory Stick Dr, Chickasha, OK 73018

  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

  John Burris Central Oklahoma Real Estate

  3808 Hickory Stick Dr, Chickasha, OK 73018
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  $211,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft

  Belmore Plan at Sleepy Hollow, Chickasha, OK 73018

  Colony Fine Homes Builder

  926 Hudson Road St Unit 36916230, Chickasha, OK 73018
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  /3

  $414,647

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,401 Sq Ft

  3812 Hickory Stick Dr, Chickasha, OK 73018

  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,

  John Burris Central Oklahoma Real Estate

  3812 Hickory Stick Dr, Chickasha, OK 73018
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  $240,000

  $35K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,078 Sq Ft

  513 County Road 1390, Chickasha, OK 73018

  Welcome to 513 County Road 1390 in Chickasha, located in the Pioneer School District and situated on a spacious 1-acre lot. This property offers a great combination of space, functionality, and recent updates. The home features 3 bedrooms and 2 bathrooms, with a garage conversion that functions as a fourth bedroom, providing flexibility for a home office, guest room, or additional living space.

  Morgan Elledge Eastwood Realty Group

  513 County Road 1390, Chickasha, OK 73018
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  /33

  $259,000

  • 3 Beds
  • 2 Baths
  • 1,683 Sq Ft

  Unlisted Address

  Welcome to 2297 CS 2880 in Chickasha, OK — a beautiful property sitting on 1 acre in the sought-after Friend Public School district! This 3 bedroom, 2 bathroom home offers the perfect mix of comfort, space, and functionality. Inside you’ll find a spacious living room, breakfast bar, granite countertops, pantry, tons of storage, and a large laundry room. The master suite offers great space with a

  Lindsey Bunch LB Realty Group-MB of Oklahoma

  Unlisted Address
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  /30

  $280,000

  $15K PRICE INCREASE

  • 4 Beds
  • 2 Baths
  • 1,706 Sq Ft

  910 Brookhollow Dr, Chickasha, OK 73018

  Welcome to 910 Brookhollow Drive in Chickasha, Oklahoma — a beautifully designed home offering the perfect blend of modern comfort, spacious living, and peaceful Oklahoma charm. Located in highly rated Chickasha Schools, this stunning 4-bedroom, 2-bath home sits on a generously sized lot and delivers the open-concept lifestyle today’s buyers are searching for. Step inside to high ceilings,

  Erica Lewis LUXE Realty Collective

  910 Brookhollow Dr, Chickasha, OK 73018
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  /39

  $244,900

  • 4 Beds
  • 2 Baths
  • 1,957 Sq Ft

  1527 S 5th St, Chickasha, OK 73018

  Welcome to this fully renovated, absolutely BEAUTIFUL home nestled on a spacious one-acre lot along one of the city’s quiet, slow-traffic streets. ***Renovations in the last two years include: new windows, doors, and spray foam insulation!*** From the moment you arrive, the stunning curb appeal is sure to tug at your heartstrings—so much so, you may be ready to call it yours before even stepping

  Becca Owens Downtown Realty Group

  1527 S 5th St, Chickasha, OK 73018
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  /48

  $202,000

  $8K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,584 Sq Ft

  1427 W Chickasha Ave, Chickasha, OK 73018

  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

  Catarina Roman H&W Realty Branch

  1427 W Chickasha Ave, Chickasha, OK 73018
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  /39

  $240,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,929 Sq Ft

  702 W Country Club Rd, Chickasha, OK 73018

  Charming updated home situated on a desirable corner lot! This well-maintained property offers plenty of space with two separate living areas, providing flexibility for entertaining, relaxing, or creating a home office or playroom. The spacious bedrooms offer comfort and room to spread out, while the main living areas feature durable vinyl flooring and the bedrooms are finished with cozy carpet.

  Neely Rozas Always Real Estate

  702 W Country Club Rd, Chickasha, OK 73018
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  $211,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,347 Sq Ft

  Wayne Plan at Sleepy Hollow, Chickasha, OK 73018

  Colony Fine Homes Builder

  926 Hudson Road St Unit 36907441, Chickasha, OK 73018
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  /22

  $220,000

  • 3 Beds
  • 3 Baths
  • 1,995 Sq Ft

  925 W Chickasha Ave, Chickasha, OK 73018

  Investor Special! This income-generating triplex brings in $2,100/month, and features three individual 1 bed/1 bath units, including one garage unit. Conveniently located less than 1 mile from the Downtown area, which is home to the famous Chickasha Leg Lamp and just a short distance to the fairgrounds, making this property even more desirable. During the holiday season, occupants can enjoy the

  Becca Owens Downtown Realty Group

  925 W Chickasha Ave, Chickasha, OK 73018
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  /31

  $299,999

  $15K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,045 Sq Ft

  1805 Todd Estate Dr, Chickasha, OK 73018

  Nestled in the sought after Todd Estates in Chickasha, Oklahoma, this home offers a single-family residence presenting a wonderful opportunity to establish roots in Grady County. Built in 1982, this property awaits your personal touch to unlock its full potential. The sunken living room presents itself for warm and cozy family time. The Jenn - air stove lends itself to homecooked meals that can

  Renee Stallings Century 21 Mosley

  1805 Todd Estate Dr, Chickasha, OK 73018
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  /17

  $215,900

  Open Sun 2PM - 4PM $9K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,525 Sq Ft

  254 County Road 1370, Chickasha, OK 73018

  Country Living at Its Finest – One Acre, Stunning Sunsets & USDA Eligible Experience the perfect blend of peaceful country living and modern comfort in this beautifully maintained 3-bedroom, 2-bath brick home situated on a picturesque one-acre homesite. With wide-open spaces, breathtaking Oklahoma sunsets, and welcoming neighbors, this property offers the lifestyle you've been dreaming about.

  Michael Carter Authentic Real Estate Svcs Grp

  254 County Road 1370, Chickasha, OK 73018
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  /17

  $210,000

  • 3 Beds
  • 2 Baths
  • 1,377 Sq Ft

  2928 Westbrook St, Chickasha, OK 73018

  Discover this newly painted and contemporary living at 2928 Westbrook ST, Chickasha, OK 73018, a single-family residence built in 2021. This property offers a fresh start in a home designed for modern comfort. The three bedrooms provide versatile spaces, accommodating various needs from tranquil sleeping quarters to productive home offices. A two-car garage offers convenient and secure parking,

  Renee Stallings Century 21 Mosley

  2928 Westbrook St, Chickasha, OK 73018
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  $211,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,394 Sq Ft

  Bristol Plan at Sleepy Hollow, Chickasha, OK 73018

  Colony Fine Homes Builder

  926 Hudson Road St Unit 36916229, Chickasha, OK 73018
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  /14

  $209,900

  New Construction $7K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,301 Sq Ft

  917 Hazy Brook Cir, Chickasha, OK 73018

  Brand New Energy-Efficient Home in Sought-After Sleepy Hollow Welcome to your forever home — a thoughtfully designed retreat where elevated ceilings, natural light, and intentional spaces invite you to breathe deeply, live fully, and settle into something truly special. Step inside and feel the difference. The spacious, continuous-flow layout creates a sense of calm and connection, perfect for

  John Burris Central Oklahoma Real Estate

  917 Hazy Brook Cir, Chickasha, OK 73018
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  /33

  $299,999

  • 4 Beds
  • 2 Baths
  • 2,404 Sq Ft

  585 County Road 1310, Chickasha, OK 73018

  Escape the city to this beautifully updated 4-bedroom, 2-bath retreat sitting on nearly 6 acres of Oklahoma gold. Spanning 2404, this home offers the perfect balance of rural peace and modern peace of mind—including a brand-new roof (July 2025) and an on site storm shelter. The interior features a split floor plan highlighted by a luxurious primary suite. You’ll love the spa-like master bath,

  Lindsey Bunch LB Realty Group-MB of Oklahoma

  585 County Road 1310, Chickasha, OK 73018
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  $211,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,257 Sq Ft

  Brady Plan at Sleepy Hollow, Chickasha, OK 73018

  Colony Fine Homes Builder

  926 Hudson Road St Unit 36907061, Chickasha, OK 73018
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  /18

  $274,900

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,853 Sq Ft

  925 Hazy Brook Cir, Chickasha, OK 73018

  MOVE IN READY, close on your new home in 30 days!! There’s just something special about walking into a home where every detail feels intentional—and this brand-new, energy-efficient beauty is exactly that. Nestled in one of the area’s most sought-after communities, this spacious 4-bedroom, 2-bath home (with an inviting covered front porch) was designed with comfort, style, and everyday living in

  John Burris Central Oklahoma Real Estate

  925 Hazy Brook Cir, Chickasha, OK 73018
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  $211,000

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,876 Sq Ft

  Ferris Plan at Sleepy Hollow, Chickasha, OK 73018

  Colony Fine Homes Builder

  926 Hudson Road St Unit 37540621, Chickasha, OK 73018
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  $211,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,502 Sq Ft

  Belmore Plus Plan at Sleepy Hollow, Chickasha, OK 73018

  Colony Fine Homes Builder

  926 Hudson Road St Unit 36916239, Chickasha, OK 73018

Showing Results 41 - 65, Page 2 of 2