Sleepy Hollow Homes for Sale

Sleepy Hollow Homes for Sale

Welcome to Sleepy Hollow, a hidden gem nestled in the heart of Florida! This enchanting subdivision offers a tranquil escape from the hustle and bustle of everyday life, making it the perfect place to call home. With its lush landscapes and charming tree-lined streets, Sleepy Hollow embodies the spirit of serene suburban living while remaining conveniently close to all the amenities you could desire.

As you explore the homes for sale in Sleepy Hollow, you’ll discover a diverse array of architectural styles, from cozy single-family homes to spacious modern residences. Each property boasts unique features, ensuring that there is something for everyone, whether you’re a first-time buyer or looking to upgrade. Many homes in this community come with generous yards, perfect for outdoor gatherings, gardening, or simply enjoying the Florida sunshine.

The community itself is family-friendly, with nearby parks, playgrounds, and excellent schools that cater to all ages. Residents of Sleepy Hollow enjoy a strong sense of community, with neighborhood events and gatherings that foster connections and friendships. Plus, with easy access to major highways, you’re just a short drive away from the vibrant culture of downtown Orlando, pristine beaches, and world-renowned attractions.

Whether you’re seeking a peaceful retreat or a lively community, Sleepy Hollow offers the perfect blend of both. Don’t miss your chance to find your dream home in this idyllic subdivision. Explore the homes for sale today and step into a lifestyle that embraces comfort, community, and convenience!

Newest Sleepy Hollow Homes for Sale

3 Beds ⋅ 2 Baths ⋅ 1229024 MLS

Make This Pool Home Your Dream Home! Welcome to this charming 3-bedroom, 2-bathroom pool home situated on a spacious oversized lot, offering plenty of room to relax, entertain, and enjoy your own private retreat. Inside, you'll find a cozy fireplace that adds warmth and character, while both the inviting front porch and screened rear porch provide the perfect spaces for morning coffee or evening gatherings. Major updates offer peace of mind, including a newer roof, resurfaced pool, newer electrical panel, and a 2024 A/C system. Conveniently located in the heart of Port Orange, this home is just minutes from shopping, dining, parks, top-rated schools, and a short drive to the area's beautiful beaches. As an added bonus, the voluntary HOA allows access to the community pool and clubhouse without the obligation of mandatory membership.

709 Tarry Town Trail, Port Orange

3 Beds ⋅ 2 Baths ⋅ 1228497 MLS

Great location in Port Orange near shopping and schools. Perfect home for a family with a huge oversized lot and community pool. Nestled in a cul-de-sac, this one needs a little TLC, so roll up your sleeves and get it before it's gone!

702 Ichabod Court, Port Orange

3 Beds ⋅ 2 Baths ⋅ OM725728 MLS

Under contract-accepting backup offers. WELCOME TO SLEEPY HOLLOW IN SE OCALA 3 BEDROOM, 2 BATH CONCRETE BLOCK BRICK POOL HOME AWAITS YOU FOR YOUR ADVENTURE. FAMILY FRIENDLY POOL to enjoy the sunshine and warm weather with a private, fenced back yard! LARGE OVERSIZED .34-acre lot with long driveway, perfect for your extra vehicles and company. All-important upgrades done on the home: NEW HVAC in 5/2024, NEW ROOF with Peel & Stick in 9/2024, POOL RENOVATED in 2024 with New Vinyl Liner, Pump, Filter, Timer, and Chlorinator, NEW WINDOWS in 12/2013 with transferable warranty. Kitchen comes with a Refrigerator, Newer Dishwasher, and Range. Home comes with a full brick fireplace in the Family room to keep you warm in the winter. Large bedrooms with plenty of closet space throughout the house. Oversized garage with workbench. Full Laundry Room inside home. Large back Screened in Lanai room to enjoy the weather. Professionally landscaped and cared for with routine maintenance on the pool and lawn. Home comes with meticulous records. Close and Convenient to local shopping centers, restaurants, golf courses, fitness clubs, and the YMCA. Enjoy strolling through the many walking paths at the Marion County Conservation Area just two blocks away, or kayaking on the incredible Silver River at the nearby Silver Springs State Park. Affordably Priced to Sell. So many more extras with this house, a must see! --

231 Se 52nd Court, Ocala

2 Beds ⋅ 2 Baths ⋅ 1227180 MLS

MOVE IN READY!!! Welcome home to this beautifully updated 2-bedroom, 2-bath residence in desirable Port Orange! Fresh interior paint and brand-new flooring create a bright, modern feel throughout. The updated kitchen features stylish finishes, ample cabinet space, and a functional layout perfect for everyday living and entertaining. The spacious primary suite offers comfort and privacy, while the second bedroom and bath provide flexibility for guests, family, or a home office. Conveniently located near shopping, dining, parks, schools, and just a short drive to the beach, this move-in-ready home is an excellent opportunity to enjoy the Florida lifestyle. Don't miss your chance to make it yours!

765 Tarry Town Trail, Port Orange

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Donna M. Rose, Owner - Broker in Charge - Lic. Realtor

Precision, Expertise and Results I am the key to your new home!! Say YES to a change of address!!! The Legal Edge: I am not your typical Realtor. With a legal background and a paralegal degree specializing in Real Estate and Family Law, I bring a level of precision to the table that is rare in this industry. Having spent years as a Real Estate Closer for a major local title company, I understand the "moving parts" of a transaction from the inside out. I don't just navigate deals; I anticipate hurdles before they arise. Award-Winning Service: Customer service isn't just a buzzword for me—it is my reputation. In 2006, I was honored with a prestigious customer service award nominated by my own peers. That award still sits on my desk today as a daily reminder of the standard I set for myself. When you work with me, you aren't just another file on my desk; my goal is to make you feel like my only client. Why Work With Me? As one of the most respected Realtors in the county with a consistent 5-star rating across major real estate platforms such as Zillow, Realtor.com and HomeLight, etc, I offer a RESULTS NOT GIMMICKS approach. * Negotiation with Precision: My legal training ensures your interests are protected at every turn. * Seamless Closings: I keep all parties on point and focused to ensure a successful, stress-free closing. * Total Dedication: Every client receives 100% of my effort from the first meeting to the final signature. Choosing the right Realtor is more than finding someone to open doors; its about finding a partner who can navigate the complexities of a legal contract and ensure a seamless closing. Call me, message me or text me. Let's get to work. 386-334-2264 donna@drpropertiesnow.com 130 Sycamore Sunshine Lane New Smyrna Beach, FL @donnaismyrealtor #donnaismyrealtor

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Stefani Turco, Broker Associate, Lic. Realtor

Turning Dreams into Addresses: Helping You Find Your Perfect Slice of Florida Paradise As a proud Florida resident for over 50 years, I’m not just invested in real estate—I’m deeply committed to this community, both professionally and personally. Married for over 23 years with four amazing children, and a lover of horses and German Shepherds, I’m passionate about helping families and investors find their perfect slice of paradise here in this beautiful state. Being a Broker Associate isn’t just about closing deals for me; it’s about turning dreams into reality. Whether you’re looking for a dream home, a vacation getaway, or a smart investment, I’m here to guide you through every step of the process with care, expertise, and a genuine commitment to your goals. In addition to being a Real Estate Broker Associate, I’m also a business owner and someone with a solid understanding of construction. This well-rounded background allows me to provide valuable insights into a property’s potential, helping you make informed decisions. My business experience has also sharpened my negotiation skills, ensuring that you get the best possible outcome—whether you’re buying or selling. With integrity, attention to detail, and a true heart for service, my goal is to make your real estate journey seamless, stress-free, and rewarding. Let’s work together to turn your vision into reality and help you find the Florida paradise you’ve always dreamed of! 130 Sycamore Sunshine Lane, New Smyrna Beach, FL 32168 386.316.7303 stefani@drpropertiesnow.com

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Jayce A. Rose, Lic. Realtor

Meet Jayce Rose - A Legacy of Excellence in Real Estate Real estate is about more than property; it's about people and the community we build together. For Jayce, real estate isn't just a career path, it’s a straightforward calling. It's literally in his blood, as the son of the founder of DR Properties, Jayce was raised in the heart of the industry. He was by his mother’s side, assisting with preparing and activating new listings, attending open houses, mastering the nuances of client communication, and observing his mother successfully navigate complex real estate transactions with grace and expertise. This early immersion provided him with a "boots-on-the-ground" education that few can match, instilling in him the core values that define his practice today. A Legacy of Excellence and a Foundation of Trust: From a young age, Jayce was more than just an observer; he was a fixture in the industry. Acting as a dedicated assistant to his mother on countless occasions, he gained an "over-the-shoulder" education that no classroom could provide. This experience instilled in him a high level of discipline, teamwork, and the competitive drive necessary to succeed in today’s fast-paced real estate market. This hands-on upbringing allowed him to witness the intricacies of the market, the art of the deal, and the importance of client relationships long before he ever held a license. Jayce understands that a successful real estate transaction is built on more than just paperwork; it’s built on trust and transparency. His years of experience have taught him the vital importance of proactive communication and expert negotiations. While using a sharp, articulate approach to advocate for his clients with an independent spirit and a relentless work ethic. he has earned a stellar reputation as a professional who is honest, trustworthy, reliable, and deeply rooted in the local community. Academic Excellence & Professional Dedication: After earning his Bachelor’s degree in Business from Daytona State College, Jayce is able to bring a strategic and well balanced edge to the team. He is able to combine his formal business education with a modern approach to a classic industry. The Tech-Forward Edge: In today’s fast-paced market, Jayce brings a vital, fresh look to the industry. He has an expert grasp of technology and social media. He knows exactly how to leverage these platforms to give properties the maximum exposure and connect with the modern buyer. Why Work With Jayce? Jayce is the "Modern Day Professional". Now, having officially passed his real estate exam, he is ready to step onto the front lines. He combines his formal business education with real-world experience to offer his clients a distinct advantage Beyond his professional credentials, Jayce is recognized by friends, colleagues and neighbors as an all-around great human being. His kindness and smart, empathetic nature makes him not just a capable Realtor, but a trusted partner in your next real estate journey.

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Dylan B. Rose, Lic. Realtor

Meet Dylan B. Rose - The Next Generation of Real Estate I believe that a successful closing is built on a foundation of honesty and data. My goal is to ensure every client feels empowered and educated at every turn. A lifelong resident with deep roots in the community, Dylan doesn’t just work in real estate, she was raised in it. For Dylan, real estate isn't just a career, its a natural progression. As the daughter of the founder of DR Properties, Dylan’s education in the industry began at the kitchen table and on-site at properties. Having served as a dedicated assistant within the family business from a young age, she developed an intuitive understanding of the market that few can match. Dylan spent her youth assisting her mother, gaining a "behind-the-scenes" education in the industry long before earning her professional credentials. A Foundation of Excellence: Dylan’s journey is backed by both experience and education. After years of hands-on training in the family business, she earned her degree from Daytona State College, blending traditional industry wisdom with a modern, academic perspective. Dylan enters the family legacy with a bold, fresh vision. She bridges the gap between traditional real estate values and the high-tech demands of today’s market. The Tech-Forward Edge: In today’s fast-paced market, Dylan brings a vital, fresh look to the industry. Recognized as a digital powerhouse in social media and technology, with a massive following across YouTube, Instagram, and Snapchat, she possesses the unique ability to turn digital engagement into real-world results. She understands that in the modern era, a property’s online presence is just as important as its curb appeal, and she uses her tech-savvy skill set to ensure her clients’ listings stand out in a crowded digital landscape. She is a true digital native with an expert grasp of technology and social media. This isn't just a hobby - ii’s a powerful marketing tool. She knows exactly how to leverage these platforms to give properties maximum exposure and connect with the modern buyer. When you work with Dylan, you aren't just getting a Realtor; you are gaining a tech-forward powerhouse who is committed to excellence, driven to succeed, and backed by a lifetime of industry expertise. She has been preparing for this role her entire life.

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Carter Brackett, Lic. Realtor

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Andrea Marlot, Lic. Realtor

As a transplant from MN, I’ve been a New Smyrna resident for only 5 years, but I was a devoted annual visitor for 25 years before relocating. I’m very acquainted with Volusia County. I’ve been a licensed Realtor since 2015 and love guiding people on their journey to homeownership. In addition to being a Realtor, I also work for an exterior home remodeling company, specifically dealing with storm related insurance claims. My knowledge of the claims industry has been very beneficial to buyers, sellers and home inspectors when issues arise during a home inspection. I have a keen eye for spotting potential damage, and I know how to seamlessly navigate the muddy waters of the claims process. Whether you’re looking to buy, sell or rent, I would love the opportunity to support your ambition!

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Susan Logan, Lic. Realtor

I have been a New Smyrna Beach resident for over 35 years and am very familiar with the area. I would love to work with you, family, or friends for all of your real estate needs.

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Marianne Breitenbruck, Event Assistant

Recently becoming a full time resident in the beautiful sunshine state, I have always believed and now I know for sure, LIFE IS BETTER AT THE BEACH!!! Come on down, the water is great. The only salt we use here is to rim the top of our margarita glass.

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