Chickasha, OK Homes for Sale under $500,000

• 

  $211,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,342 Sq Ft

  Alistair Plan at Sleepy Hollow, Chickasha, OK 73018

  Colony Fine Homes Builder

  926 Hudson Road St Unit 36907308, Chickasha, OK 73018
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  /49

  $284,999

  • 3 Beds
  • 2.5 Baths
  • 2,365 Sq Ft

  2202 Lakewood Dr, Chickasha, OK 73018

  A rare opportunity to own a home with character, updates, and a stocked pond right in the backyard. Tucked into The Harbors with no active HOA, this property offers a peaceful setting with walking trails, stairs leading to the pond, and room to fish, kayak, or simply catch the sunset. Major updates completed this summer include a new HVAC, new roof, and updated plumbing. Inside, hardwood floors

  Lauren Ruth BHGRE The Platinum Collective

  2202 Lakewood Dr, Chickasha, OK 73018
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  /5

  $231,990

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,510 Sq Ft

  2800 Scissortail Dr, Chickasha, OK 73018

  1510 B3 - Lincoln The Lincoln Plan from our Liberty Series offers the perfect combination of efficiency, comfort, and value. This single-story home features 4 bedrooms, 2 bathrooms, a 2-car garage, and 1,510 square feet of thoughtfully designed living space. Upon entering, you ll find three secondary bedrooms, a full-size bathroom, and a conveniently located laundry room. The heart of the home is

  National Home Corp Builder

  2800 Scissortail Dr, Chickasha, OK 73018
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  /45

  $279,000

  • 5 Beds
  • 2 Baths
  • 2,640 Sq Ft

  701 S 6th St, Chickasha, OK 73018

  This exquisite Victorian charmer, ideally situated on a large corner lot in Chickasha, invites you to experience historic grandeur, starting with the stunning original woodwork gracing the banister upon entry. The chef's kitchen continues this theme of beautiful craftsmanship with complementary wood details, creating a warm and inviting space perfect for culinary endeavors. Boasting five spacious

  Tara Levinson LRE Realty, LLC

  701 S 6th St, Chickasha, OK 73018
• 

  $211,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,333 Sq Ft

  Abingdon Plan at Sleepy Hollow, Chickasha, OK 73018

  Colony Fine Homes Builder

  926 Hudson Road St Unit 36916227, Chickasha, OK 73018
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  /47

  $249,900

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,129 Sq Ft

  1624 W Idaho Ave, Chickasha, OK 73018

  Congratulations—you’ve found a 100-year-old home that somehow skipped the whole “crumbling and haunted” phase and went straight to “basically brand new.” This charming overachiever has been completely redone from top to bottom—plumbing, electrical, HVAC, drywall, flooring, cabinets, appliances, driveway... you name it, it’s new. So yes, you get all the character of a century-old home without

  Rachel Hartless Keller Williams Realty Elite

  1624 W Idaho Ave, Chickasha, OK 73018
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  /36

  $275,999

  $4K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,038 Sq Ft

  802 S 12th St, Chickasha, OK 73018

  Assignable VA loan! Situated on a corner lot in Chickasha, this beautiful 3 bedroom, 3 bathroom home offers approximately 2,250 square feet of living space with plenty of room to spread out. The interior features a comfortable layout with spacious living areas and large windows that bring in natural light throughout the home. Energy efficient Low E windows and recently added attic insulation help

  Amanda Bertelli Eastwood Rlty Group Inc (BO)

  802 S 12th St, Chickasha, OK 73018
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  /7

  $248,990

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,671 Sq Ft

  2320 S 28th Terrace, Chickasha, OK 73018

  1671 B3 - Grant The Grant Plan from our Liberty Series offers a spacious single-story layout with approximately 1,671 square feet, 4 bedrooms, and 2 bathrooms. Designed for comfortable everyday living, this home features an open-concept main living area, a private primary suite, and three additional bedrooms with flexible space for family, guests, or a home office. At the heart of the home, the

  National Home Corp Builder

  2320 S 28th Terrace, Chickasha, OK 73018
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  /5

  $312,500

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,005 Sq Ft

  Hadley Plan at Sleepy Hollow, Chickasha, OK 73018

  Welcome to the Hadley! A beautifully crafted, single-story brick house designed for comfort, connection, and lasting memories. Featuring 4 spacious bedrooms, 2 baths, and an open-concept living area with soaring 10-foot ceilings, this home offers the perfect blend of elegance and functionality. The heart of the home is a light-filled kitchen with a large island and walk-in pantry, opening into a

  Colony Fine Homes Builder

  926 Hudson Road St Unit 37540536, Chickasha, OK 73018
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  /33

  $225,000

  $22M PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,304 Sq Ft

  27 Shannon Dr, Chickasha, OK 73018

  Tucked away at the end of a quiet cul-de-sac and backing directly to Shannon Springs Park, this spacious home offers the perfect blend of privacy, convenience, and outdoor living. Step outside your backyard gate to enjoy scenic walking trails, playgrounds, peaceful morning coffee strolls, or relaxing evening walks through one of Chickasha’s most beloved parks. Inside, you’ll find generous living

  Becca Owens Downtown Realty Group

  27 Shannon Dr, 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
• 

  $211,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,458 Sq Ft

  Charlotte Plan at Sleepy Hollow, Chickasha, OK 73018

  Colony Fine Homes Builder

  926 Hudson Road St Unit 36916245, Chickasha, OK 73018
• 

  

  /7

  $248,990

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,671 Sq Ft

  2804 Scissortail Dr, Chickasha, OK 73018

  1671 B3 - Grant The Grant Plan from our Liberty Series offers a spacious single-story layout with approximately 1,671 square feet, 4 bedrooms, and 2 bathrooms. Designed for comfortable everyday living, this home features an open-concept main living area, a private primary suite, and three additional bedrooms with flexible space for family, guests, or a home office. At the heart of the home, the

  National Home Corp Builder

  2804 Scissortail Dr, Chickasha, OK 73018
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  /46

  $299,900

  $35K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,872 Sq Ft

  1401 W Chickasha Ave, Chickasha, OK 73018

  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

  Jeffrey Logan Logan Real Estate Co.

  1401 W Chickasha Ave, Chickasha, OK 73018
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  /32

  $219,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,016 Sq Ft

  2493 County Street 2806, Chickasha, OK 73018

  Welcome to your private one-acre retreat, where country freedom meets modern comfort! From the moment you pull up the driveway, this remarkable property impresses with its rare combination of expansive acreage and thoughtful, versatile living spaces. Step inside to discover a beautifully designed floor plan anchored by two separate, light-filled living rooms. This unique setup offers unmatched

  Michael Carter Authentic Real Estate Svcs Grp

  2493 County Street 2806, Chickasha, OK 73018
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  /5

  $232,990

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,510 Sq Ft

  2316 S 28th Terrace, Chickasha, OK 73018

  1510 B3 - Lincoln The Lincoln Plan from our Liberty Series offers the perfect combination of efficiency, comfort, and value. This single-story home features 4 bedrooms, 2 bathrooms, a 2-car garage, and 1,510 square feet of thoughtfully designed living space. Upon entering, you ll find three secondary bedrooms, a full-size bathroom, and a conveniently located laundry room. The heart of the home is

  National Home Corp Builder

  2316 S 28th Terrace, 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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  /5

  $265,990

  New Construction

  • 5 Beds
  • 3 Baths
  • 1,804 Sq Ft

  2808 Scissortail Dr, Chickasha, OK 73018

  1804-2 B3 - MadisonThe Madison Plan from our Liberty Series combines style and functionality in a layout that maximizes space for your family s needs. This 2-story home features 5 bedrooms, 3 bathrooms, a 2-car garage, and 1,804 square feet of well-designed living space.As you step inside, you ll find a main-level bedroom and a full bathroom, offering a convenient option for

  National Home Corp Builder

  2808 Scissortail Dr, Chickasha, OK 73018
• 

  /2

  $312,500

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,005 Sq Ft

  3404 Hickory Stick Dr, Chickasha, OK 73018

  This is more than a new home—it's the fresh start you've been longing for. Step inside and feel the difference: soaring elevated ceilings, sunlight pouring into an open, spacious layout designed to breathe with you, not press in around you in this thoughtful 4 bedroom 2 and a half bath home! Every detail speaks of care and comfort—luxury vinyl plank flooring underfoot, gleaming quartz countertops

  Colony Fine Homes Builder

  3404 Hickory Stick Dr, Chickasha, OK 73018
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  /48

  $445,000

  • 3 Beds
  • 2.5 Baths
  • 2,992 Sq Ft

  3304 Pondridge Rd, Chickasha, OK 73018

  Beautiful Home in Chickasha, Oklahoma for sale by broker Jon Brown. This home is 2992 sq. ft. with 3 bedrooms, 2 1/2 baths, Living area, media room, kitchen with bar and breakfast nook, dining area, utility, huge 3 car garage with shop area and stairs to large attic. The home located in one of the nicest additions in Chickasha, just south of Golf course, on a wonderful lot overlooking a small

  Jon Brown Brown Auction and Real Estate

  3304 Pondridge Rd, Chickasha, OK 73018
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  /51

  $209,900

  New Construction

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

  Ashton Plan at Sleepy Hollow, Chickasha, OK 73018

  The Ashton floor design offers affordability and versatility. This three-bedroom plan has a master oasis, two secondary rooms, and a spacious living room that is perfect for family movie nights or hosting friends for the big game! *Image is a rendering. Colors, styles, and options may deviate from the picture.

  Colony Fine Homes Builder

  926 Hudson Road St Unit 36916223, Chickasha, OK 73018
• 

  

  /22

  $244,500

  New Construction

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

  924 Hazy Brook Cir, Chickasha, OK 73018

  MOVE IN READY, close in 30 days! USDA & VA eligible!! Rate buy down options!!! This is more than a new home—it's the fresh start you've been longing for. Step inside and feel the difference: soaring elevated ceilings, sunlight pouring into an open, spacious layout designed to breathe with you, not press in around you.Every detail speaks of care and comfort—luxury vinyl plank flooring underfoot,

  Colony Fine Homes Builder

  924 Hazy Brook Cir, Chickasha, OK 73018
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  /37

  $268,800

  $51K 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, tucked away on a winding cul-de-sac street in a beloved Chickasha neighborhood full of storybook charm, character & timeless curb appeal. This original home offers the kind of space, craftsmanship & distinctive details increasingly difficult to find. Inside, original woodwork, cabinetry, built-ins & mid-century details offer glimpses of the home's

  Tina Curtis eXp Realty, LLC

  2824 Nichols Rd, Chickasha, OK 73018
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  /17

  $222,825

  New Construction

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

  921 Hazy Brook Cir, Chickasha, OK 73018

  MOVE IN READY! Close in 30 days!! $0 down options, USDA & VA eligable!!! Just Listed – Brand New Energy-Efficient Home in Sleepy Hollow There's something truly special about a home that's brand new—where every corner, every finish, and every detail has been thoughtfully designed with you in mind. Welcome to this beautifully crafted 3-bedroom, 2-bath home located in the highly sought-after Sleepy

  Colony Fine Homes Builder

  921 Hazy Brook Cir, Chickasha, OK 73018
• 

  

  /22

  $274,900

  New Construction

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

  925 Hazy Brook Cir, Chickasha, OK 73018

  MOVE IN READY! CLose in 30 days!! USDA $0 down options & VA eligibale!!! 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,

  Colony Fine Homes Builder

  925 Hazy Brook Cir, Chickasha, OK 73018
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  /44

  $265,000

  • 2 Beds
  • 2 Baths
  • 1,788 Sq Ft

  245 E Riddle Rd, Chickasha, OK 73018

  Enjoy peaceful country living just minutes from town at 245 E Riddle Rd. in Chickasha Situated on approximately 2.1 acres, this brick home offers 2 spacious bedrooms, 2 full bathrooms, and approximately 1,788 sq. ft. of living space with plenty of room both inside and out. The home features oversized bedrooms with excellent closet space and a large family room/sunroom across the back of the home,

  Shari Brunt Always Real Estate

  245 E Riddle Rd, Chickasha, OK 73018
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  /5

  $254,990

  New Construction

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

  Duxbury Plan at Sleepy Hollow, Chickasha, OK 73018

  The Duxbury design is a stunning layout. This four-bedroom plan has a primary oasis, three large secondary rooms, and a spacious living room that is perfect for family movie nights or hosting friends for the big game. The Duxbury Plan also includes a covered patio for grilling or watching the sunset! *Image is a rendering. Colors, styles, and options may deviate from the picture.

  Colony Fine Homes Builder

  926 Hudson Road St Unit 36916248, Chickasha, OK 73018
• 

  $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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  /2

  $288,500

  New Construction

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

  920 Hazy Brook Cir, Chickasha, OK 73018

  MOVE IN READY, close in 30 days! $0 down options, USDA & VA eligible!! rate buy down options!! This beautifully crafted home combines comfort and style in the highly sought-after Sleepy Hollow community! Fall in love with this spacious 4 bed, 2 bath brand new energy-efficient home that perfectly blends comfort, style, and smart living. From the moment you walk in, the elevated ceilings in the

  Colony Fine Homes Builder

  920 Hazy Brook Cir, Chickasha, OK 73018
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  /6

  $228,990

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,510 Sq Ft

  2812 Scissortail Dr, Chickasha, OK 73018

  1510 A3 - Lincoln The Lincoln Plan from our Liberty Series offers the perfect combination of efficiency, comfort, and value. This single-story home features 4 bedrooms, 2 bathrooms, a 2-car garage, and 1,510 square feet of thoughtfully designed living space. Upon entering, you ll find three secondary bedrooms, a full-size bathroom, and a conveniently located laundry room. The heart of the home is

  National Home Corp Builder

  2812 Scissortail Dr, Chickasha, OK 73018
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  /32

  $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 Rlty Group Inc (BO)

  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
• 

  

  /33

  $276,900

  $8K PRICE DROP

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

  1948 County Street 2826, Chickasha, OK 73018

  Experience the best of country living just minutes from Chickasha. Nestled on more than half an acre, this beautifully maintained property offers the perfect combination of space, comfort, and modern updates. Inside, you'll find a functional floor plan featuring three bedrooms, two full bathrooms, a two-car attached garage, generous storage throughout, and a versatile SHOP that provides endless

  Amanda Bertelli Eastwood Rlty Group Inc (BO)

  1948 County Street 2826, Chickasha, OK 73018
• 

  

  /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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  /34

  $254,900

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,985 Sq Ft

  1904 S 21st St, Chickasha, OK 73018

  Y'all, this is the kind of place that feels like home the minute you pull into the driveway. Beautifully remodeled and sitting on over a quarter-acre lot, this spacious 1,985-square-foot home has all the fresh updates you've been looking for.Step inside to discover gorgeous designer-inspired color palettes, brand-new carpet, and fresh paint throughout, creating a bright, inviting space

  Jason Baker Downtown Realty Group

  1904 S 21st 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

  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
• 

  $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
• 

  

  /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
• 

  

  /5

  $265,990

  New Construction

  • 5 Beds
  • 3 Baths
  • 1,804 Sq Ft

  2321 S 28th Terrace, Chickasha, OK 73018

  1804-2 B3 - MadisonThe Madison Plan from our Liberty Series combines style and functionality in a layout that maximizes space for your family s needs. This 2-story home features 5 bedrooms, 3 bathrooms, a 2-car garage, and 1,804 square feet of well-designed living space.As you step inside, you ll find a main-level bedroom and a full bathroom, offering a convenient option for

  National Home Corp Builder

  2321 S 28th Terrace, Chickasha, OK 73018

Showing Results 41 - 80, Page 2 of 3