Winter Run Homes for Sale

Winter Run Homes for Sale

Welcome to Winter Run, a picturesque subdivision nestled in the heart of Orlando, Florida, within the vibrant Orange County. This charming community is renowned for its tranquil atmosphere, lush landscapes, and friendly neighborhood vibe, making it the perfect place to call home.

Winter Run boasts a diverse selection of homes for sale, catering to various preferences and lifestyles. Whether you're searching for a cozy single-family residence or a spacious townhome, you'll find an array of options that suit your needs. Many properties feature modern amenities, open floor plans, and beautiful outdoor spaces, ideal for entertaining or enjoying serene evenings under the Florida sky.

One of the standout features of Winter Run is its commitment to community living. Residents enjoy access to well-maintained parks, walking trails, and recreational facilities, promoting an active and engaging lifestyle. The neighborhood is also conveniently located near top-rated schools, shopping centers, and dining options, ensuring that everything you need is just a stone's throw away.

For families, Winter Run is a dream come true, with a strong sense of community and plenty of opportunities for social interaction. Kids can play safely in the parks, while parents can join in on community events that foster a welcoming environment.

If you're looking to make a move to Orlando, Winter Run is an exceptional choice. With homes for sale that reflect the warmth and charm of Florida living, this subdivision is not just a place to live—it's a place to thrive. Explore your options today and discover the perfect home in Winter Run!

Newest Winter Run Homes for Sale

3 Beds ⋅ 2 Baths ⋅ O6395675 MLS

Under contract-accepting backup offers. This unique property is a standout opportunity for a large family or a strategic investor. This quiet neighborhood is conveniently located close to shopping and major highways. 2017 roof, and a recently updated water heater, the home is move-in ready. Its location is unbeatable—less than a mile from I-4 and the Mall at Millenia, with world-class attractions just minutes away. This gem is priced to move, so schedule your tour before it’s gone! Should I focus the next version more on the interior features or the prime location?

5401 Winter Run Drive, Orlando

Start Your Search

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

Learn More

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

Learn More

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.

Learn More

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.

Learn More

Carter Brackett, Lic. Realtor

Learn More

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!

Learn More

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.

Learn More

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.

Learn More

Browse Winter Run Homes by Exterior features