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The Cape House

Quintessential Cape

By Julie Craven Wagner · Photography courtesy of Robert Paul Properties

For Keenan Flynn, what makes up a quintessential Cape Cod rental property is an understanding that is deeply ingrained in his body, mind and soul. Flynn, who grew up in Cotuit and spent childhood summers racing down to the docks of the iconic Mosquito Yacht Club and riding his bike in a quiet village atmosphere that is repeated up and down the region, knows what a summer experience on the Cape is all about. Today, he is member of the Robert Paul Real Estate team, representing both buyers and sellers, and considers himself fortunate to be able to raise his own family in Cotuit. After all, how many of us can claim that our children are growing up the way we did?

But, being a landlord was not forefront in Flynn’s life plans. A visit to a college friend’s new summer home in Edgartown planted the seed. “I asked them, ‘how did you manage to get such a great home?’” Flynn explains. “They said, ‘Well, we come for six weeks of the year, and we rent it the rest of the time. That covers all of the expenses.’ Suddenly, I started to look at real estate differently.” Flynn, who at the time was not in the real estate business, set about analyzing which parts of the Cape were in premium demand for high-quality seasonal rentals. His research concluded that the communities of Chatham and Osterville were the preferred destinations for the kind of properties that interested him; Osterville was a natural choice due to his proximity in neighboring Cotuit. 

31 Parker Road came on the market at just the right time. The previous owners had outgrown their beloved Cape getaway, and the timing was right for both parties. The sellers  were looking to up-size, and Flynn was ready to enter the market. “The previous owners were meticulous when it came to maintenance on the home, and I have followed suit,” Flynn says about making the property truly turnkey. “So, to get the house ready for the upcoming season, all we had to do was decorate and stock it.” 

This summer will be the third season that Flynn has welcomed renters, who have become more like extended family, into his charming Cape cottage. “We have been lucky that a portion of our tenants have become repeat clients,” Flynn explains. “And they not only have deliberately chosen their preferred weeks, but in some cases, extended the duration of their booking.” For anyone who visits the property, that does not come as a surprise. The home, which is a short stroll to everything the village of Osterville has to offer, is that type of Cape Cod cottage that could show up on the silver screen. A picket fence with a cottage garden in full bloom greets visitors and passersby with a casual charm that encourages a stop for a whiff of roses and daylilies. White clapboard on the exterior is brought to life by an aqua painted front door crowned with a seaside wreath that whispers, “Come on in, and maybe stay awhile.” 

Inside, the cottage charm is evident by the freshly painted white, mid-century paneling and convenient built-ins throughout. Neat and tailored comfortable furniture, in coastal hues of blue and white, pull together a spacious seating area in the living room with a focus on a warm fireplace. This is not one of those typical summer rentals cobbled together with a collection of furnishing sourced from the attic and local second-hand shops. Instead, attention to detail with a focus on a cohesive and thoughtful design is apparent at every turn. Bedrooms are freshly made with crisp Boll and Branch linens, while wool needlepoint throw rugs provide comfort as they grace beautifully stained hardwood floors. The four bathrooms are modern and pristine and allow enough privacy for everyone in the four-bedroom house. But, the charming interior of a time gone by is not the only appeal of this getaway.

The backyard and outdoor spaces are simply unexpected in such an idyllic presentation. Outside, among a lush and maintenance-free landscape, a mesmerizing waterfall splashes into an in-ground pool, with a swim-up bar that offers an oasis for a fun-filled retreat. A fully functional outdoor kitchen services the bar that has seating both in the pool and out, allowing those that prefer to stay dry or wet for their summer vacation to indulge in either. A dining area is perched above the pool in the shade for family dinners. Additionally under cover, in the adjacent pool cabana, a comfortable sectional wraps around another bar capped by a large screen television. For those seeking a mega-dose of vitamin D and perhaps a golden-hue to their skin, sturdy and comfortable padded chaise loungers stand at the ready on the surrounding stone pool decking. A collection of comfortable seating surrounds a spacious fire pit, providing the perfect place to unwind and connect during the cool evenings.

Flynn has chosen Michelle Sylvia with Robert Paul Properties to represent and handle all of the business associated with his unique property. “If I could make any suggestion to anyone considering an investment property, it would be to use a realtor,” Flynn shares. “I was not in the real estate business when I took this on, so I can speak from both sides without bias. But to have a professional that is responsible for all aspects of this property means not only that I have peace of mind, but, I believe, that I am a better neighbor to the abutters and the village as well.” Flynn touches on an important point that is perhaps not considered as deeply for other investment homeowners. With a third party handling the responsibility of the myriad of considerations involved in the business of seasonal rental property, the headaches and reputation of the individual homeowner are far less at risk.

On that fateful ferry ride to the Vineyard, to connect with his college friend, Keenan Flynn might never have expected that his future would be instrumental in creating a space for memories and meaningful respite for complete strangers, but in fact, he is providing a home for those who are in search of just that.

This property can be found at or by contacting Michelle Sylvia at or Keenan Flynn directly at 

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