NEW LISTING: Exceptional 5-Bedroom Home in Winchester's Rolling Hills Estates

Geri Deane
15 hours ago
4 min read

2708 Cassidy Ct., Winchester, VA 22601 | Offered at $650,000

There's a moment in every house hunt when you walk through the door and just know. That inexplicable feeling when a house whispers "welcome home" before you've even seen all the rooms. After helping families find their perfect homes for nearly two decades, I've learned to trust that feeling—and this Winchester beauty on Cassidy Court has it in spades.

View the full MLS listing here: 2708 Cassidy Ct., Winchester, VA 22601

A Home That Opens Doors to All Possibilities

Coming soon to the market (just in time for Thanksgiving!), 2708 Cassidy Court offers something increasingly rare in today's market: a home that's genuinely move-in ready while still leaving room for you to make it yours. Set on a peaceful cul-de-sac in Rolling Hills Estates, this five-bedroom residence checks every box my buyers have been searching for—and then some.

With approximately 3,552 square feet of beautifully maintained living space, this home effortlessly flows from intimate family moments to grand holiday gatherings. The main level's open floorplan—anchored by a gourmet kitchen with granite countertops, stainless steel appliances, and that butler's pantry we all dream about—creates the kind of natural gathering spaces where memories are made.

But here's what really captured my heart: the finished walk-out basement with its own private bedroom and full bath. In our new work-from-home world, this kind of flexible space isn't just nice to have—it's essential. Whether it becomes your home office, your teenager's retreat, or the perfect in-law suite, this space adapts to your life, not the other way around.

Why Winchester? Why Now?

Let me share something about Winchester that even some longtime Northern Virginians don't fully appreciate: this is a city that's managed to do what so few have—preserve its soul while thoughtfully planning for its future.

When I drive through Old Town Winchester's cobblestone streets, past George Washington's Office Museum (yes, our first president actually worked here!), I'm reminded that this isn't just another D.C. suburb. This is a place with its own identity, its own rhythm, its own story.

The Winchester You'll Fall in Love With

Historic Old Town: Just minutes from Rolling Hills Estates, the Loudoun Street Pedestrian Mall offers a walkable downtown that feels both timeless and totally current. On Saturday mornings, you'll find me at the Old Town Farmers Market, where local producers bring everything from heirloom tomatoes to artisan breads. The kids splash in the fountains while adults browse the boutiques and galleries that give Winchester its creative edge.

The Loudoun Street Pedestrain Mall in Winchester VA

Cultural Richness: Between Shenandoah University's performances, the Bright Box Theater's comedy nights, and the Museum of the Shenandoah Valley's stunning gardens, there's always something happening. And can we talk about the Apple Blossom Festival? This 100-year-old tradition transforms the entire city each spring into a ten-day celebration that rivals anything you'll find in the metro area.

The annual Apple Blossom Festival in Winchester, VA — Every spring since 1924, Winchester has crowned Queen Shenandoah, welcomed thousands of firefighters for the nation's largest firefighters' parade, and painted the town pink and green. This isn't just a festival—it's who we are.

Farm-to-Table Living: Winchester sits at the heart of Virginia's agricultural bounty. Places like West Oaks Farm Market and Virginia Farm Market aren't just stores—they're community gathering spots where you can pick up fresh sweet corn in the morning and enjoy farm-to-table dining by lunch. My personal favorite? Those warm apple cider donuts from Virginia Farm Market that practically melt in your mouth.

West Oaks Farm Market in Winchester VA — West Oaks Farm Market—where Sunday morning coffee comes with mountain views and everything from sweet corn to homemade pies is grown right here in Frederick County. This is why we love Winchester living.

The Great Outdoors: With the Shenandoah Valley as your backyard, outdoor adventures are limitless. The Museum of the Shenandoah Valley alone offers miles of trails dotted with sculptures, while Abrams Creek Wetlands Preserve provides peaceful nature walks just two miles from downtown. And when you want to really escape? Shenandoah National Park's northern entrance is just minutes away.

Abrams Creek Wetlands Preserve in Winchester VA — You haven't really experienced Winchester until you've spotted your first wood duck at Abrams Creek Wetlands. Just minutes from downtown, this preserve is where residents reconnect with nature without leaving the neighborhood

The Cedar Valley Factor: Winchester's Next Chapter

Here's insider information that savvy buyers need to know: the upcoming Cedar Valley development is about to transform this neighborhood in the best possible way. By March 2027, a 50,325-square-foot Publix will anchor this mixed-use project, bringing upscale grocery shopping practically to your doorstep. But it's not just about convenience—the planned rooftop recreational facilities, including pickleball courts, signal Winchester's evolution into a destination that honors its past while embracing an active, modern lifestyle.

What does this mean for Rolling Hills Estates? Early buyers here will benefit from Winchester's thoughtful growth while enjoying the established neighborhood charm that makes this area so special. It's the kind of opportunity that doesn't come along often—getting in before the transformation while prices still reflect today's market, not tomorrow's potential.

The Details That Matter

5 bedrooms, 3.5 baths – including that versatile basement suite
Approximately 3,552 square feet of thoughtfully designed living space
0.35-acre cul-de-sac lot in Rolling Hills Estates
Three-car garage with abundant storage
Fully fenced backyard with Trex deck and lighting
Walk-out basement with recreation room, office, and private bedroom suite
Offered at $650,000

Your Invitation to See It First

Professional photos will be available Tuesday, November 26th, and this home officially hits the market Wednesday—yes, the day before Thanksgiving. But here's what I know after years in this business: the best opportunities don't wait for perfect timing.

If you've been searching for a home that offers both the convenience of city amenities and the peace of suburban living, where you can walk to dinner downtown on Friday night and hike mountain trails on Saturday morning, where your investment is protected by thoughtful development and strong community values—this might be your moment.

Winchester is having its moment too. The question is: will you be part of it?

Let's schedule your private showing before the holiday rush begins. Because sometimes, the best gift you can give your family is a fresh start in a home that opens doors to all possibilities.

Ready to explore what Winchester living could mean for you? Contact Geri Deane at Hunt Country Sotheby's International Realty. Because your next chapter deserves nothing less than extraordinary.