From Overgrown to Enchanted: Transforming Doc’s Family Pittsburgh Airbnb
When I first set eyes on our Bellevue property four years ago, it felt more wilderness than welcoming retreat. The house itself had starter home vibes —but the grounds were completely overrun with invasive Japanese maples, tangled brush, overgrown hillside, and a drainage nightmare that pooled water at the back sliding door every time it rained hard. We knew that to offer guests a true “cottage in the woods” experience—just ten minutes from downtown Pittsburgh—we needed to rethink the landscape from the ground up.
A Vision Rooted in Nature and Community
Our inspiration was simple: create outdoor spaces where families could gather, dog tails could wag safely, and children could explore winding paths through the woods—while still being a stone’s throw from the city. We imagined a network of meandering trails connecting future guest cottages, a shared container-gym, a sauna, and a sparkling pool, all converging on a cozy Belgian stone-and-boulder patio under the trees. My husband’s foresight—seeing beyond the weeds to what could be—set the stage for every decision that followed.
Battling the Overgrowth
Before the overhaul, all four sides of the home needed desperate help battling the overgrowth. The hillside next to the home was a tangle of tall grass and weeds, and the wooded perimeter threatened to swallow our tiny backyard. The driveway was filled with uneven rock with treacherous dips, and rainwater rushed the driveway often flooding the rear sliding glass door entrance and softening the soil into a muddy mess. Our first task was simply to beat back the jungle—clearing invasive Japanese maple and reclaiming what had once been lawn.
Partnering with True Landscape Visionaries
Not all landscapers are created equal. After a couple of underwhelming attempts—local workers who mowed but never transformed—we found Sylvan Gardens. From the moment John Friend arrived with listening ears and sketchpad in hand, we knew we’d found partners who cared as much about this property as we did. John’s collaborative design wove our ideas into a practical plan that made the most of both the main lot and the adjacent vacant parcel.
As we pushed deeper into our phased expansion, we regularly call on trusted contractors such as John Grandstand to clear back new brush, and Nick Robbins to carefully remove aging or dangerous trees—keeping our vision moving forward, one section of woods at a time.
Reimagining the Driveway
Few things frustrate guests more than an uneven driveway and trying to drag luggage across it without tripping or spraining an ankle. It was not visually appealing and was one of the last areas on the main lot that we tackled in 2024. Earlier in 2024, after yet another flash flood at the back door, we asked Sylvan Gardens to completely redo the slope and grade. They smoothed out the dips, extended the lawn across the lower driveway edge, and built a raised flower bed to divert runoff away from the house. Today, the driveway feels like a natural extension of the home, guiding visitors toward the front porch or to the rear of the home easily without a single puddle in sight.
The Heart of the Yard: Our Patio Retreat
If there’s one “wow” moment on the property, it’s our outdoor patio built into the sloping hillside leading into the vacant lot. Using Belgian block and oversized boulders, Sylvan Gardens created a fireside gathering spot that looks plucked from a mountain cabin—complete with a handcrafted stairway leading into the woods. The lush, expanded lawn now stretches behind the house, replacing the former tangle with endless green space for kids and pups to roam.
Guests Feel the Magic
Since completing the overhaul, our reviews light up with praise:
“The back yard was fabulous for fur babies and was like a mini-park for them to run and explore. The location is private and the grounds are beautifully landscaped with wonderful areas to relax!”
“…the yard was paradise for our dogs! The home was better than pictured - we even saw deer, rabbits and a groundhog near the yard on a few occasions!”
It’s immensely rewarding to know that our home—once hidden under years of overgrowth—now offers that idyllic escape families crave.
Challenges, Lessons, and Commitment
As with any large, long-term undertaking, budget constraints control how fast we move on projects. We reinvest every dollar of Airbnb income back into the next phase of development and improvements for the home. The Pittsburgh seasons dictate the pace of work but Sylvan Gardens manages that well enough that we don’t have to worry about it. Our biggest lessons throughout these last few y ears are to pace ourselves, lean on trusted contractors, and staying true to our vision of creating a “cottage in the woods.” Each little milestone is another success we celebrate in our Airbnb journey.
Ongoing Care & Future Dreams
Today, Sylvan Gardens tends to our property from spring through fall, ensuring everything stays as pristine as the day it was installed. Guests will often see them in the springtime mowing and managing the property. Meanwhile, we’re laying the groundwork on the vacant lot—planning paths deeper into the woods, mapping out foundations for future guest cottages, and dreaming bigger every season.
Your Invitation to Experience the Transformation
At Doc’s Family Pittsburgh, we’re not just hosting—we’re sharing our home. Every tree cut, bush cleared, and stone placed was done with you in mind. We take your feedback seriously and pour it right back into creating the best stay possible. Come see for yourself how an overgrown lot became a family-friendly woodland retreat—just ten minutes from downtown. We can’t wait to welcome you.
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