Together, Pretty Picky Properties Select Vacation Rentals and Monomoy Real Estate and Construction make up a locally based partnership focused on differentiating service, communication and trust

It’s no secret that the seasonality of this region is a difficult hurdle that visitors and homeowners alike must learn how to navigate. When the warm summer breeze gives way to breathtaking fall foliage and then to chilly winter frost, the iconic Cape cottages and breathtaking waterfront homes still stand. Throughout it all, from the days when children squealing along the beach is a never-ending yet welcome soundtrack, to the nights when the quiet patter of snowfall is the background to an evening spent warm in bed, it’s important to those of us that love this area, that love these homes and that love the people who keep the Cape and Islands running throughout year after year, that the lights stay on. For this reason, and many others, renting is an indescribable asset to the Cape community—one that ensures an influx of new faces to keep the region a vibrant destination spot as well as ensuring that longtime homeowners, many of whom have been a crucial asset to the region for generations, keep coming back. 

“For us, it’s all about providing a unique Cape Cod vacation,” says Blake Decker, CEO of Pretty Picky Properties. Pretty Picky is a multi-generational, family owned and operated business focused on providing both homeowners and guests to the Lower Cape with a high quality, hands-on rental experience. “We are very selective in the homes that we manage,” explains Decker. “Because of this, guests know that the quality and service level will be consistent.” As the name suggests, the “picky” aspect of Pretty Picky means that both homeowners and renters can have peace of mind that they are getting the best possible service and dealing with the best possible properties for their budget and unique specifications. 

Pretty Picky also provides rental management services unique in the market. For example, trained detailers execute an exclusive “Property Prep Punch List” on site each rental turnover day, checking everything from WiFi functionality to making sure there is adequate bath tissue in every bathroom. By partnering with and augmenting the cleaning service, Pretty Picky assures that each property is ideally prepared for arriving guests. For guests new to a property, Pretty Picky also offers an in-person greeting on site to orient them to the property and answer any questions about the home or the area. “The most important thing we do is communicate,” says Decker. “Communication with guests, owners and vendors is so important to creating a seamless vacation experience for everyone involved. In our business, we have the client who is the homeowner and the customer who is the guest, so we are constantly trying to optimize our communication to achieve great results for both.”

For homeowners, putting a space up for rent can be a daunting challenge. Besides the obvious concern about hosting strangers in a space that is likely very personal, there are other challenges involved to ensuring that a property is both attractive and fit for guests. Pretty Picky and Monomoy Real Estate & Construction have joined forces to put homeowners’ trepidations at ease and to ensure that renters have the absolute best experience possible. “Pretty Picky Properties is the rental extension of Monomoy just as Monomoy is the sales, custom home building and property management extension of Pretty Picky. The end result of these combined talents is a uniquely comprehensive service which affords our clients the ability to make purchase, renovation or rental decisions with a confidence that can only come from knowing that they have covered all bases,” says Justin Blair, managing partner for Monomoy. 

As Decker puts it, the partnership between these two companies creates a “one-stop shop.” “Justin Blair and I have been friends since we worked together at Chatham Bars Inn in college,” explains Decker about the genesis of their partnership. “When I moved into the rental world, his own business was starting to morph into a sales, brokerage and construction company, and we decided to join forces. The goal is to be able to do anything with real estate on the Cape other than insure homes,” says Decker with a laugh. 

Homeowners looking to jump into the rental business, or investors looking to acquire a rental property, can count on this unique partnership to remodel and outfit their home in a way that suits their goals and then to continue a communicative, trusting partnership throughout the rental process. “We work very closely with homeowners looking to renovate their homes in order to rent,” says Blair. “The process will ultimately result in a set of strategic improvements, which will enhance rental returns as well as the underlying asset value.  This takes the form of advising from general home layout, sleeping arrangements and amenities down to fit and finish, interior design and outfitting the house properly for rental guests.  The most successful renovations are the product of a trusting relationship with the homeowner and a shared set of goals for the property.  Not all rental properties are intended for 100 percent maximization of the fiscal return.  Some owners use rental income to pay for their costs to own the property so that their use is essentially free. Understanding the end game is essential for us to be truly effective as advisors.” And on top of all that, clients and renters can expect personalized attention and superior service and quality thanks to the selective nature of these two companies. It is truly the best of both worlds.

“This Chatham property is a shining example of everything we offer together with Monomoy,” explains Decker. After working with the owner to rent the property for years, he indicated his desire to sell, and Pretty Picky and Monomoy were able to find a buyer from their client base who then brought them on board to handle renovations and future rentals. “The project in Chatham was a dream,” says Blair. “In a wonderful collaboration with the new owners, we planned and executed a smart renovation project, which returned the home to its original glory—and then some.” “It was a classic balancing act of maintaining that classic Cape charm but bringing the home into the 21st century,” adds Decker. “Monomoy was able to make the character of the home shine while still being attractive to a modern audience. A lot of the homes we deal with are built specifically for an owner, but in this case the home was designed to appeal to a broad market since it was going to be a rental from the outset. Having that insight allowed us to be creative and come up with the ultimate vacation home for today’s market.” 

With this home, the Pretty Picky and Monomoy partnership resulted in a space with old-Cape charm, coastal flair and modern amenities. “The end product was a functional, photo-spread worthy home with a graceful combination of old and new woven together with a coastal interior,” says Blair. “We now serve as property managers for the happy homeowners and enjoy their company when they are in town to use it for themselves.” 

“We are all likely to agree that the seasonality of our regional economy is unique. This results in a dynamic ebb and flow amongst our business lines so we are never faced with an ‘off season,’” says Blair, “only a new season with a shift in focus.” With these two companies pairing extraordinary experiences with personalized assistance across the Lower Cape, clients are in good hands. As Blair puts it, “establishing a trusting relationship is the most important and enjoyable aspect of what we do. Those relationships have varied narratives. Some begin with a home search and end with the start of a multi-generational family legacy on Cape Cod. Others begin with the question of ‘should we renovate our bathroom if we hope to rent’ and develop into a thoughtful redesign aimed at maximizing both rental revenue and asset value. Regardless of the story, we cherish the opportunity to become partners with our clients along the way. Quality work or a successful, income-producing property does not have the same, lasting impact unless that feeling of partnership, born only from trust, is present.”

Staging provided by The Mayflower in Chatham. Interior design by Washashore Home.