Sleepy Hollow Homes under $400,000

Welcome to Sleepy Hollow, a charming neighborhood nestled in the heart of Oklahoma that seamlessly blends tranquility with community spirit. Known for its picturesque tree-lined streets and friendly atmosphere, Sleepy Hollow is the perfect place for families, young professionals, and retirees alike. The area boasts a rich tapestry of history, with homes that reflect a variety of architectural styles, from cozy cottages to modern designs, ensuring there’s something for everyone.

One of the standout features of Sleepy Hollow is its affordability. With a selection of homes available for under $400,000, this neighborhood offers an incredible opportunity for first-time buyers and those looking to invest in a welcoming community. Imagine finding your dream home complete with spacious backyards, perfect for weekend barbecues or quiet evenings under the stars.

Living in Sleepy Hollow means enjoying the best of both worlds—serenity and convenience. Residents have access to local parks, walking trails, and recreational facilities, making it easy to stay active and enjoy the outdoors. The neighborhood also features top-rated schools, shopping centers, and dining options just a short drive away, ensuring that all your needs are met without sacrificing the peaceful lifestyle you desire.

Whether you're looking to settle down or start anew, Sleepy Hollow invites you to explore its delightful homes and vibrant community. Discover the charm of this hidden gem in Oklahoma, where your ideal home awaits!

Newest Sleepy Hollow Homes under $400,000

$312,500

4 Beds ⋅ 3 Baths ⋅ 1252768 MLS

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 that elevate every moment in the kitchen. This isn’t just about beauty. It’s smart, too—energy efficient from top to bottom, with an EV charger ready for the future you’ve worked so hard to build. But here's the truth: homes like this don’t wait. Not in this market. Not with features like these. And not with the feeling you get the moment you walk through the door—the undeniable sense that this is it. The back patio is a true extension of your home & this homesite backs up to a treeline making evenings out back gorgeous & serene. Don’t let this one slip away. This is your chance. Anticipated completion September 2026, reserve your new home today!!

3404 Hickorystick Drive, Chickasha

$230,500

3 Beds ⋅ 2 Baths ⋅ 1252493 MLS

$0 down options, USDA & VA eligible. The Ashton is beautifully designed where style and function come together seamlessly. This is the perfect fhome for entertaining, with a big island kitchen that flows effortlessly into the living areas, making hosting a breeze. Imagine cozying up on the nice back patio that offers privacy backing up to a beautiful treeline, perfect for relaxing or sharing a moment with loved ones. The oversized primary bedroom is a true retreat—your own personal sanctuary. Elevated ceilings in both the living areas and primary bedroom make everything feel spacious and luxurious. With a tankless gas hot water heater, you'll never run out of comfort, and those quartz countertops, pure elegance. Plus, gorgeous luxury vinyl flooring in the wet areas gives you durability and beauty in one. Open, airy, and full of light—this home is everything you want and need. And for that added touch of convenience, it’s ready for an EV charger! This is your home. Your sanctuary. Your future. Don't let it slip away, schedule to have a look today

3420 Hickorystick Drive, Chickasha

$246,500

3 Beds ⋅ 2 Baths ⋅ 1252487 MLS

$0 down options, USDA & VA eligible. The Charlotte is a beautiful spacious, open-concept home with elevated ceilings that make every room feel grand, including the luxurious primary bedroom, it is spacious enough to create your own personal retreat. The luxury vinyl flooring in the wet areas is sleek and stylish, adding to the overall sophistication of the space. The kitchen is a masterpiece, with gorgeous quartz countertops and a flush bartop island perfect for entertaining or family gatherings.The pantry is perfectly positioned giving you plenty of space for all your kitchen essentials and more. Step into the primary bathroom and closet – they’re every girl’s dream! It’s not just big, it’s designed for comfort, with ample storage and beautiful finishes that make getting ready each day feel like a treat. The secondary bedrooms are roomy and perfect with a spacious hall bath to match.and with plenty of built-ins throughout, you’ll have all the storage you need.The covered back patio is perfect for relaxing and outdoor entertaining with a beautiful treeline that your new home backs up to. And let’s not forget about the large laundry room, tankless gas hot water heater, and the fact that this home is llocaqted in the highly sought after Sleepy Hollow making it the perfect choice for you. With easy access to highways and the turnpike, you’ll never be far from where you need to be. This isn’t just a house; it’s the home you’ve been waiting for – this home is anticipated to complete in December. Reserve your new home today.

3416 Hickorystick Drive, Chickasha

$245,500

3 Beds ⋅ 2 Baths ⋅ 1252485 MLS

$0 down options, USDA & VA eligible! The Charlotte offers a spacious, open-concept living area with elevated ceilings that make every room feel grand, including the luxurious owners suite, it is spacious enough to create your own personal retreat. The luxury vinyl flooring in the living areas is sleek and stylish, adding to the overall sophistication of the space. The kitchen is a masterpiece, with gorgeous quartz countertops and a beautiful flush bartop island perfect for entertaining or gatherings. The pantry gives you plenty of space for all your kitchen essentials and more. Step into the owners suit, It's not just big, it’s designed for comfort, with ample storage and beautiful finishes that make getting ready each day feel like a treat. The secondary bedrooms are roomy with a spacious hall bath to match and with plenty of built-ins throughout, you’ll have all the storage you need. The covered back patio is perfect for relaxing and outdoor entertaining, And let’s not forget about the large laundry room, tankless gas hot water heater, and the fact that this home is located in the highly sought after Sleepy Hollow. With easy access to highways and the turnpike, you’ll never be far from where you need to be. This isn’t just a house; it’s the home you’ve been waiting for – schedule today so you can have a look

3412 Hickorystick Drive, Chickasha

$233,500

3 Beds ⋅ 2 Baths ⋅ 1252482 MLS

$0 down options, USDA & VA eligible. The Abingdon—isn’t just a house, it’s the perfect home. Perfect for entertaining, the big island kitchen is the heart of the home, creating an effortless flow that makes hosting a breeze. BIG front porch to greet guests, and a covered back patio to relax in style—this is the space where memories are made. Elevated ceilings in the living areas and primary bedroom bring that WOW factor, giving you a sense of luxury and comfort every time you step inside. Tankless gas hot water heater—endless, efficient comfort. Stunning quartz countertops and gorgeous luxury vinyl flooring in the wet areas—practical yet beautiful at every turn. Spacious, open, airy—this home flows perfectly, every single day. Plus, EV charger ready to keep you and your future eco-friendly lifestyle powered up! This home is calling your name—don’t miss your chance, schedule to have a look today

3408 Hickorystick Drive, Chickasha

$288,500

4 Beds ⋅ 2 Baths ⋅ 1247458 MLS

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 living areas and primary suite create an open, airy feel that’s simply unforgettable. Enjoy gorgeous quartz countertops, luxury vinyl plank flooring, and a layout designed for real life—roomy, modern, and made to impress. You’ll love knowing this home is built for the future, with a high-efficiency HVAC system, EV charger, tankless water heater, and a 10-year structural warranty providing peace of mind. Outside, the beautifully landscaped yard creates instant curb appeal, making this house feel like home from the very first glance. Located just minutes from the Turnpike and close to major employers like Cimarron Trailer, Standley Systems, HSI Sensing, LSPI, and Fort Sill, you’ll have both convenience and community right at your doorstep. Don’t wait—this is your chance to own new construction at an incredible value! Reserve this home today before someone else calls it home.

920 Hazy Brook Circle, Chickasha

$244,500

3 Beds ⋅ 2 Baths ⋅ 1247457 MLS

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, gleaming quartz countertops that elevate every moment in the kitchen. This isn’t just about beauty. It’s smart, too—energy efficient from top to bottom, with an EV charger ready for the future you’ve worked so hard to build. You’ll love knowing this home is built for the future, with a high-efficiency HVAC system, EV charger, tankless water heater, and a 10-year structural warranty providing peace of mind. Outside, the beautifully landscaped yard creates instant curb appeal, making this house feel like home from the very first glance. Located just minutes from the Turnpike and close to major employers like Cimarron Trailer, Standley Systems, HSI Sensing, LSPI, and Fort Sill, you’ll have both convenience and community right at your doorstep. Don’t wait—this is your chance to own new construction at an incredible value! But here's the truth: homes like this don’t wait. Not in this market or this community. Not with features like these. And not with the feeling you get the moment you walk through the door—the undeniable sense that this is it. Don’t let this home slip away. This is your chance. Secure your new home in the fast selling Sleepy Hollow community today!

924 Hazy Brook Circle, Chickasha

$380,411

4 Beds ⋅ 3 Baths ⋅ 1246495 MLS

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 heart of the home, showcasing stylish cabinetry, premium finishes, abundant counter space, and an inviting layout ideal for gatherings. Retreat to the serene owner’s suite featuring a spa-inspired bath and generous closet space, while the additional bedrooms provide flexibility. Step outside to enjoy the beautifully covered back patio overlooking an oversized homesite — the perfect setting for relaxing evenings, outdoor dining, and weekend entertaining. Ideally located just minutes from the turnpike, this exceptional home offers convenient access to major employers including Cimarron Trailers, Stanley Systems, HSI Sensing, LSPI, and Fort Sill, you'll have both convenience and an elevated lifestyle. Experience the perfect combination of sophistication, space, and location — a place you’ll be proud to call home.

3808 W Hickorystick Drive, Chickasha

$119,000

3 Beds ⋅ 2 Baths ⋅ 1241543 MLS

Welcome home to this charming 3-bedroom, 1.25-bath home in the heart of Tecumseh! Freshly updated with new paint and flooring throughout, this home offers a clean, modern feel while maintaining its unique character. The standout feature is the stunning interior rock wall, creating the perfect focal point for adding a cozy wood-burning stove and making the living space warm and inviting. A functional floor plan provides comfortable living, while the attached 1-car garage adds convenience and extra storage. Whether you're a first-time homebuyer, looking to downsize, or searching for an investment opportunity, this move-in-ready home is one you won't want to miss. Schedule your private showing today! ***Living room furniture is an AI edited image to show what living room could look like***

1623 Hardwood Grove Street, Tecumseh

$274,900

4 Beds ⋅ 2 Baths ⋅ 1236295 MLS

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 mind. Step inside and you’ll be greeted by elevated ceilings that make the open living spaces feel light and airy, while luxury vinyl plank flooring runs throughout the main areas dding warmth and texture. The heart of the home—the kitchen—features sleek quartz countertops that perfectly balance modern design with timeless appeal. You’ll love knowing this home is built for the future, with a high-efficiency HVAC system, EV charger, tankless water heater, and a 10-year structural warranty giving you peace of mind. Outside, the beautifully landscaped yard creates instant curb appeal, making this house feel like home from the very first glance. Located just minutes from the Turnpike and close to major employers like Cimarron Trailer, Standley Systems, HSI Sensing, LSPI, and Fort Sill, you’ll have both convenience and community right at your doorstep. This isn’t just a place to live—it’s a place to plant roots, gather, and make memories for years to come.

925 Hazy Brook Circle, Chickasha

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