Chickasha, OK Homes for Sale under $500,000

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  /31

  $289,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,970 Sq Ft

  1395 U S 62, Chickasha, OK 73018

  Beat the heat! Cool earth-sheltered living has low utility bills!Sweeping PANORAMIC views of the Washita Valley from this stunning HILLTOP RETREAT just off Highway 62 east of Chickasha. Tucked away in a SECLUDED setting on 1.7 acres, this property delivers the kind of peace and scenery you just can’t find every day. Picture evenings on the FLAGSTONE PATIO by the OUTDOOR wood-burning

  

  Kim Green

  Countryside Realty

  1395 U S 62, Chickasha, OK 73018
• Explore Chickasha

• 

  

  

  /33

  $219,500

  Open Sun 1PM - 3PM $6K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,735 Sq Ft

  2225 W Country Club Rd, Chickasha, OK 73018

  Welcome to 2225 Country Club Road in Chickasha, Oklahoma! This charming 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and summertime living.Step inside to a spacious living room that’s ideal for hosting friends, relaxing after a long day, or enjoying movie nights together. The open dining area flows seamlessly into the kitchen, creating a great space for gathering—whether

  

  Sarah Neal

  Metro Brokers of OK Connect

  2225 W Country Club Rd, Chickasha, OK 73018
• 

  

  

  /38

  $405,000

  • 5 Beds
  • 2.5 Baths
  • 2,064 Sq Ft

  1858 Highway 81, Chickasha, OK 73018

  Completely remodeled and move-in ready, this exceptional brick home on approximately 6 acres offers the perfect blend of modern updates, country living, and room to grow. Originally designed as a 3-bedroom, 2.5-bath home, it has been thoughtfully reconfigured into a spacious 5-bedroom, 2.5-bath residence, or utilize one of the oversized rooms as the perfect bonus room, game room, homeschool

  

  Tami Utsler

  Clear Choice Realty & Auction

  1858 Highway 81, Chickasha, OK 73018
• 

  

  

  /29

  $220,000

  • 3 Beds
  • 2 Baths
  • 2,005 Sq Ft

  203 Elmhurst Dr, Chickasha, OK 73018

  Opportunity awaits with this well-built ranch-style home nestled in a quiet, established neighborhood in Chickasha. Full of character and timeless appeal, this solid home has been lovingly maintained over the years and is ready for its next owner to bring their vision and personal style to life. Whether you're a first-time buyer looking to build equity, an investor searching for a quality

  

  Tami Utsler

  Clear Choice Realty & Auction

  203 Elmhurst Dr, Chickasha, OK 73018
• 

  

  

  /36

  $395,000

  Open Sat 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 2,017 Sq Ft

  523 W Country Club Rd, Chickasha, OK 73018

  OPEN HOUSE - Sat., July 18 - 2 to 4 PMPut your business where it can grow. Located on 4 commercial acres along Country Club Road just west of Highway 81 south of Chickasha, this C-1 zoned property offers the ideal combination of visibility, space, and functionality for small business owners, contractors, service companies, landscapers, tradesmen, equipment operators, or entrepreneurs needing

  

  Kim Green

  Countryside Realty

  523 W Country Club Rd, Chickasha, OK 73018
• 

  

  /41

  $309,000

  • 4 Beds
  • 2 Baths
  • 3,621 Sq Ft

  108 Saint Charles Place, Chickasha, OK 73018

  Move-in ready 4-bedroom, 2-bath home with a spacious living area that flows into a functional kitchen and dining space. The split floor plan offers added privacy, with a primary suite separate from the secondary bedrooms. Outside features a generously sized yard with room for outdoor activities. Conveniently located near schools, shopping, and dining.

  

  Alicia Perry

  Black Label Realty

  108 Saint Charles Place, Chickasha, OK 73018
• 

  

  /47

  $275,000

  $4K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,930 Sq Ft

  416 Quail Rd, Chickasha, OK 73018

  Enjoy wide-open country living on 10.21 acres including pasture, pond and a creek with a small bridge adds character to the landscape. This peaceful rural property features a large barn with working stalls, ideal for horses or livestock. Two additional sheds provide ample space for storage or projects. A secondary lateral line and well offer flexibility for future improvements, including a

  

  Suehzen Mosley

  Century 21 Mosley

  416 Quail Rd, Chickasha, OK 73018
• 

  

  /48

  $299,900

  $25K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,617 Sq Ft

  1928 W Idaho Ave, Chickasha, OK 73018

  This amazing property sits on almost 1/2 acre in town! If you're an outdoor enthusiast, this is the home for you! Complete with koi pond with waterfalls and a walking bridge, a fire pit, and several outbuildings including a two car detached garage with shop area, you will feel like you're in your own little oasis outside of the city. Add string lights to the multiple power outlets in the garden

  

  Suehzen Mosley

  Century 21 Mosley

  1928 W Idaho Ave, Chickasha, OK 73018
• 

  

  /38

  $237,500

  • Land
  • 25 Acres
  • $9,500 per Acre

  0 Cs 2860 Unit Tract D, Chickasha, OK 73018

  Here is a beautiful opportunity to own land just outside of Chickasha. Property is in the Friend School District and then Chickasha or Amber. Property offers an abundance of trees and bermuda grass. This is a good mixture of open terraced terrain and thick trees and brush. Just minutes from Chickasha, and with easy access to I-44 and Highway 62. This will be a pacel split off of a larger parcel.

  

  Suehzen Mosley

  Century 21 Mosley

  0 Cs 2860 Unit Tract D, Chickasha, OK 73018
• 

  

  /37

  $314,500

  • Land
  • 37 Acres
  • $8,500 per Acre

  0 Cs 2860 Unit Tract B, Chickasha, OK 73018

  Here is a beautiful opportunity to own land just outside of Chickasha. Property is in the Friend School District and then Chickasha or Amber. Property offers an abundance of trees, bermuda grass, as well as a nice pond. This is a good mixture of open terraced terrain and thick trees and brush. Just minutes from Chickasha, and with easy access to I-44 and Highway 62, you'll be hard pressed to find

  

  Suehzen Mosley

  Century 21 Mosley

  0 Cs 2860 Unit Tract B, Chickasha, OK 73018
• 

  

  /48

  $375,000

  • 3 Beds
  • 2 Baths
  • 2,624 Sq Ft

  2102 Lakewood Dr, Chickasha, OK 73018

  Welcome to lakefront living in The Harbors! This beautifully maintained 3-bedroom, 2-bath home with a Brand new class 4 roof on 2 lots totaling approximately 1.5 acres, offering a rare combination of space, privacy, and waterfront views right in Chickasha. With direct pond access, mature trees, and multiple outdoor entertaining areas, the backyard feels like your own private retreat complete with

  

  Trey Adams

  Downtown Realty Group

  2102 Lakewood Dr, Chickasha, OK 73018
• 

  

  /54

  $475,000

  $23K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,922 Sq Ft

  1887 State Highway 92, Chickasha, OK 73018

  Situated on 6.81 acres in the highly sought after Amber Pocasset School District, this beautifully positioned brick home offers the perfect balance of comfort, efficiency, and opportunity. Featuring 3 bedrooms with an optional 4th bedroom and 3 full baths, the home provides flexible living space ideal for a growing family, home office, guest suite, or hobby room. A geothermal heating and cooling

  

  Tami Utsler

  Clear Choice Realty and Auction LP

  1887 State Highway 92, Chickasha, OK 73018
• 

  

  /50

  $335,000

  • 4 Beds
  • 2.5 Baths
  • 3,092 Sq Ft

  1016 W Kansas Ave, Chickasha, OK 73018

  Imagine stepping into a piece of history at 1016 W Kansas Ave. The single family residence built in 1906 offers a unique blend of timeless character and modern potential. This property presents an opportunity to craft a living space that reflects your personal style and aspirations. The foyer offers charm and warmth and is flanked by a beautiful office/sitting room/music room. The Acacia wood

  

  Suehzen Mosley

  Century 21 Mosley

  1016 W Kansas Ave, Chickasha, OK 73018
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  /50

  $359,000

  • 3 Beds
  • 2.5 Baths
  • 3,933 Sq Ft

  2293 County Street 2814, Chickasha, OK 73018

  Need space? Here it is!! This roomy home not only offers space inside, but outside too! Located in the Rock Creek Addition on the west side of town, this home offers elbow room for spreading out, but it is a neighborhood for taking walks and seeing friends.This home offers great space with it being a home run for multi-generational needs. The street level offers the main bedroom and

  

  Suehzen Mosley

  Century 21 Mosley

  2293 County Street 2814, Chickasha, OK 73018
• 

  

  /39

  $357,000

  • Land
  • 42 Acres
  • $8,500 per Acre

  0 Cs 2860 Unit Tract C, Chickasha, OK 73018

  Here is a beautiful opportunity to own land just outside of Chickasha. Property is in the Friend School District and then Chickasha or Amber. There was a home on the property years ago, well and septic condition is unknown. Property offers an abundance of trees, bermuda grass. This is a good mixture of open terraced terrain and thick trees and brush. Just minutes from Chickasha, and with easy

  

  Suehzen Mosley

  Century 21 Mosley

  0 Cs 2860 Unit Tract C, Chickasha, OK 73018
• 

  

  /40

  $475,000

  $23K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,922 Sq Ft

  1887 State Highway 92, Chickasha, OK 73018

  Located in the desirable Amber Pocasset School District, this 3 bedroom home with optional 4th bedroom and 3 full baths offers the perfect blend of country living, efficiency, and future potential on 6.81 acres. The brick home provides a comfortable layout with flexible space that can easily accommodate a home office, guest room, or additional bedroom depending on your needs. A geothermal system

  

  Tami Utsler

  Clear Choice Realty & Auction

  1887 State Highway 92, Chickasha, OK 73018
• 

  

  /48

  $205,000

  $34K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,803 Sq Ft

  728 S 13th St, Chickasha, OK 73018

  NEW ROOF BEFORE CLOSING! BUYER MAY CHOOSE COLORSitting on a large corner lot at 728 S 13th ST, Chickasha, OK 73018, this property offers an opportunity to own a single-family residence in Chickasha with a fenced yard, garage, carport and easy in/out drive. This home offers a chance to settle into a comfortable lifestyle including three bedrooms that present a personal space for your specific

  

  Suehzen Mosley

  Century 21 Mosley

  728 S 13th St, Chickasha, OK 73018
• 

  

  /41

  $286,500

  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

  John Burris Central Oklahoma Real Estate

  920 Hazy Brook Cir, Chickasha, OK 73018
• 

  

  /11

  $229,900

  New Construction $4K PRICE DROP

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

  908 Shady Meadow Way, Chickasha, OK 73018

  Step inside a luminous, open-plan sanctuary that feels expansive and inviting from the moment you walk through the front door. Gorgeous, harmonious color palettes blend soft neutrals with warm accents, creating an environment that’s both restful and uplifting—an ambiance best described as peaceful, purposeful, and full of possibility The chef-inspired kitchen shines with sleek quartz countertops,

  John Burris Central Oklahoma Real Estate

  908 Shady Meadow Way, Chickasha, OK 73018
• 

  

  /11

  $399,000

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft

  2758 County Street 2780, Chickasha, OK 73018

  78 Acres of Scenic Bliss – Endless Possibilities Await! Discover the perfect blend of serenity and potential with this stunning 78-acre property just minutes from Chickasha and within the desirable Pioneer School District. Featuring breathtaking views, rolling hills, and open skies, this land offers a rare opportunity to embrace country living at its finest. Whether you're dreaming of building

  Sarah Van Ess Downtown Realty Group

  2758 County Street 2780, Chickasha, OK 73018
• 

  $211,000

  New Construction

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

  Finley Plan at Sleepy Hollow, Chickasha, OK 73018

  Colony Fine Homes Builder

  926 Hudson Road St Unit 36916272, Chickasha, OK 73018
• 

  

  /44

  $270,000

  $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,371 Sq Ft

  1224 W Minnesota Ave, Chickasha, OK 73018

  Stunning historic home full of character and timeless craftsmanship in the heart of Chickasha! Situated on a spacious 0.44-acre corner lot, this impressive 3 bedroom, 2 bathroom property offers over 3,300 square feet of living space with classic architectural details throughout. Built in 1900, this two-story brick home showcases beautiful arched entryways, clay tile roofing, and a truly unique

  Joshua Woods Cherrywood

  1224 W Minnesota Ave, Chickasha, OK 73018
• 

  

  /37

  $310,000

  Open Sun 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,844 Sq Ft

  722 County Road 1350, Chickasha, OK 73018

  A beautiful brick home with a NEW 2026 ROOF situated on a spacious rural setting, offering the perfect blend of comfort, functionality, and peaceful surroundings. This property features an inviting covered front porch, mature landscaping, and excellent curb appeal. NEW ROOF 2026!Step inside to an open-concept layout with a large living area, complete with a tray ceiling, abundant natural

  Shari Brunt Always Real Estate

  722 County Road 1350, Chickasha, OK 73018
• 

  

  /4

  $310,500

  New Construction

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

  3404 Hickorystick Dr, Chickasha, OK 73018

  Secure your opportunity to own The Brooke Floor Plan, now under construction and available for reservation before completion. This beautifully designed home offers the perfect balance of style, comfort, and value—ideal for today’s lifestyle, whether you work from home or simply want a space that elevates everyday living. Step inside and experience the inviting open-concept design where a spacious

  John Burris Central Oklahoma Real Estate

  3404 Hickorystick Dr, Chickasha, OK 73018
• 

  

  /11

  $350,000

  $150K PRICE DROP

  • Land
  • 8.45 Acres
  • $41,420 per Acre

  0000 Highway 81, Chickasha, OK 73067

  Prime location along S. Highway 81 just past the turnoff at N 2830 Road, directly across from the new Dollar General with excellent visibility and steady traffic exposure. This 8.45 acre property previously had a home that has since been removed, leaving a clean slate ready for your next venture. Positioned in the path of growth, Chickasha continues to see exciting development, including the

  Amanda Bertelli Eastwood Realty Group

  0000 Highway 81, Chickasha, OK 73067
• 

  

  /50

  $474,900

  $24K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,365 Sq Ft

  416 Fieldcrest Dr, Chickasha, OK 73018

  This beautiful custom-built 4-bedroom, 3.1-bathroom home is loaded with amenities! It features a spacious kitchen perfect for cooking and entertaining, along with a large primary suite complete with a cozy fireplace and an expansive primary bathroom. This home offers two oversized bedrooms with a Jack and Jill bathroom. The real gem of this home is the large addition that offers an extra living

  Sarah Van Ess Downtown Realty Group

  416 Fieldcrest Dr, Chickasha, OK 73018
• 

  

  /36

  $249,500

  • 3 Beds
  • 2 Baths
  • 1,598 Sq Ft

  2814 County Street 2870, Chickasha, OK 73018

  Escape to country living with this beautifully updated 3-bedroom, 2-bath home situated on 2 acres in Chickasha. Modern style with wide-open acreage, this move-in-ready property offers the perfect balance of comfort and rural charm. Step inside to discover a stunning remodeled kitchen featuring quartz countertops, a herringbone tile backsplash, floating wood shelves, stainless steel appliances,

  Janet Apitsch McGraw REALTORS (BO)

  2814 County Street 2870, Chickasha, OK 73018
• 

  

  /48

  $259,000

  $21K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,048 Sq Ft

  727 S 16th St, Chickasha, OK 73018

  Welcome to 727 S 16th Street in Chickasha! This 4-bedroom, 2 full bath, 1 half bath home offers space, flexibility, and functionality in an established neighborhood. Situated on a desirable corner lot, you’ll appreciate the extra yard space and added curb appeal. Inside, you’ll find generous living areas with a layout that provides room for everyone. The kitchen offers great workspace and

  Cheryl Gruntmeir Always Real Estate

  727 S 16th St, Chickasha, OK 73018
• 

  $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
• 

  

  /46

  $499,000

  $51K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,618 Sq Ft

  35 Mckenzie Dr, Chickasha, OK 73018

  Located on 2.18 acres just outside Chickasha city limits, this 4-bedroom, 3.5-bath home gives you the space and privacy of country living while still being just minutes from town. The property features an inground pool, a large shop, and a separate mother-in-law home that works great for guests, family, or extra space. Inside, you’ll find granite countertops in the kitchen along with a large

  Shari Brunt Always Real Estate

  35 Mckenzie Dr, Chickasha, OK 73018
• 

  

  /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
• 

  

  /36

  $275,999

  $4K PRICE DROP

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

  802 S 12th St, Chickasha, OK 73018

  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 improve comfort

  Amanda Bertelli Eastwood Realty Group

  802 S 12th St, Chickasha, OK 73018
• 

  $211,000

  New Construction

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

  Hadley Plan at Sleepy Hollow, Chickasha, OK 73018

  Colony Fine Homes Builder

  926 Hudson Road St Unit 37540536, Chickasha, OK 73018
• 

  

  /26

  $279,900

  • 4 Beds
  • 2 Baths
  • 1,726 Sq Ft

  911 Sleepy Hollow Blvd, Chickasha, OK 73018

  Nestled on the beloved Sleepy Hollow Boulevard in one of Chickasha's most sought-after and growing neighborhoods, this stunning 4-bedroom, 2.5-bathroom craftsman home, built in 2019, offers the perfect blend of comfort and style. Step inside to a cozy floor plan designed for easy living. The living room features a welcoming fireplace, while the open-concept main area boasts vaulted ceilings,

  Becca Owens Downtown Realty Group

  911 Sleepy Hollow Blvd, 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
• 

  

  /46

  $334,900

  • 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
• 

  

  /32

  $230,000

  Open Sun 2PM - 4PM

  • 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
• 

  

  /14

  $250,000

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

  3015 Brooke Rd, Chickasha, OK 73018

  Assume This 4.75% FHA Loan — Pay ~$234/mo Less Than Today’s Rates* **** NEW ROOF, NEW GUTTERS and SIDING being installed for insurance claim **** Rare assumable mortgage opportunity in Chickasha, OK! Here’s something you rarely see right now: any qualified buyer can take over this FHA loan at a low 4.75% interest rate while today’s market sits at 6.5% and up. On a home in this price range, that’s

  Brian Jamison Salt Real Estate Inc

  3015 Brooke Rd, Chickasha, OK 73018
• 

  

  /3

  $242,500

  New Construction

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

  924 Hazy Brook Cir, Chickasha, OK 73018

  This is more than a new home—it's the fresh start you've been longing for. Step inside and feelthe 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, gleaming quartz countertops that elevate every moment in the kitchen. This isn't

  John Burris Central Oklahoma Real Estate

  924 Hazy Brook Cir, Chickasha, OK 73018

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