Sleepy Hollow Real Estate

Welcome to Sleepy Hollow, Oklahoma—a hidden gem that perfectly blends serene living with a vibrant community spirit. Nestled amidst rolling hills and lush landscapes, this charming neighborhood is an ideal retreat for families, retirees, and anyone seeking a tranquil lifestyle without sacrificing convenience.

Sleepy Hollow boasts a rich tapestry of natural beauty, with tree-lined streets and well-maintained parks that invite afternoon strolls and weekend picnics. The neighborhood is known for its friendly atmosphere, where neighbors greet each other with smiles and children play freely in safe, open spaces. The community hosts seasonal events, fostering connections and creating lasting memories for residents of all ages.

Education is a cornerstone of Sleepy Hollow, with access to reputable schools that prioritize student growth and achievement. Families can rest easy knowing their children are receiving a quality education in a supportive environment. For those who enjoy outdoor activities, the nearby parks and recreational facilities offer a variety of options, from hiking trails to sports fields, ensuring there’s always something to do.

Convenience is key in Sleepy Hollow, with local shops, restaurants, and essential services just a short drive away. Whether you’re in the mood for a cozy café or a family-owned diner, you’ll find delightful options that reflect the warmth of the community.

In Sleepy Hollow, you’re not just buying a home; you’re investing in a lifestyle. With its picturesque surroundings, strong sense of community, and commitment to quality living, Sleepy Hollow is more than a neighborhood—it’s a place to call home. Come discover the charm and tranquility that await you in this delightful Oklahoma enclave!

Newest Listings in Sleepy Hollow

$254,990

4 Beds ⋅ 2 Baths ⋅ 1248437 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. 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. Don’t let this one slip away. This is your chance. Schedule your showing today!

928 Hazy Brook Circle, 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

$414,647

4 Beds ⋅ 3 Baths ⋅ 1246499 MLS

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, study space & everyday organization. The private owner’s retreat provides a peaceful escape with a spa-inspired ensuite bath and generous closet space, while the additional bedrooms offer flexibility. Step outside to the beautifully covered back patio overlooking a huge homesite, creating the perfect outdoor oasis for relaxing evenings, gatherings, and enjoying Oklahoma sunsets. Conveniently located just minutes from the turnpike, the Aaliyah Elite offers quick access to major employers including Cimarron Trailers, Stanley Systems, HSI Sensing, LSPI, and Fort Sill, making this home the perfect blend of luxury, convenience, and lifestyle. Discover the elegance of the Aaliyah Elite — where sophisticated design meets everyday functionality in the heart of Chickasha.

3812 W Hickorystick Drive, Chickasha

$410,745

4 Beds ⋅ 3 Baths ⋅ 1246497 MLS

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 maximize comfort, style, and every aspect of modern living. Step inside and you’ll be greeted by dramatic, soaring ceilings that make the vast, open living spaces feel light, airy, and truly magnificent. The heart of the home—the kitchen—features a sleek quartz island that perfectly balances modern design with timeless appeal, creating an ideal central hub for large gatherings and effortless entertaining. Significantly expanding your usable space, the large covered back patio becomes a natural outdoor living room, perfect for enjoying the outdoors. You’ll enjoy total peace of mind knowing this home is built for the future. It includes a high-efficiency HVAC system, an EV charger, a tankless water heater, and a valuable 10-year structural warranty. 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 a fantastic community right at your doorstep. Reserve this brand-new, energy-efficient home today before it is gone like the others! This isn't just a place to live—it's a sprawling haven designed to plant roots, gather, and make memories for years to come.

3804 W Hickorystick Drive, 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

$44,900

1242197 MLS

Imagine designing your own custom home in Chickasha! This large lot, almost 3/4 of an acre, will allow you to have a great floor plan and still have room for a circle drive in front, a building in back, and a pool too, if desired. No required builder on this lot. No neighbors behind, and no floorplan you wish were different...just your custom plans!

3820 Hickory Stick Drive, Chickasha

$125,000

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

$312,500

4 Beds ⋅ 3 Baths ⋅ 1235443 MLS

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 island overlooks the main living area, highlighted by a cozy corner fireplace that creates the perfect setting for entertaining or relaxing. A private flex room with a stylish barn door offers the versatility for a home office, study, or creative space. The chef-inspired kitchen is a true centerpiece, featuring built-in stainless steel Samsung appliances, a 5-burner gas range, farmhouse sink, large pantry, under-cabinet lighting, soft-close cabinetry, and a striking freestanding island designed for both function and style. Located in the desirable Bellatona community, residents enjoy a scenic 6-acre park and playground along with convenient access to University of Oklahoma, Lake Thunderbird, Sooner Mall, and Interstate 35, placing shopping, dining, and entertainment just minutes away. Opportunities to secure a home like this before completion are limited. Schedule your private tour today and experience the style and convenience of The Brooke Floor Plan in Bellatona before it’s gone.

3404 Hickorystick Drive, Chickasha

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