For most New Yorkers, having any private outdoor space is close to winning the real estate lottery. But to turn the space into an oasis where you can unwind in style, no matter the season? That’s another proposition altogether.

One Tribeca couple has owned their top floor loft and 765-square foot rooftop space for about 20 years, furnishing the latter simply with pressure-treated lumber, a few planters and some old lounges and chairs. Seeking an upgrade from barebones functionality to a year-round sanctuary for relaxing and entertaining, they worked with an architect to create a weather-resistant retreat featuring an outdoor kitchen and private shower, as well as a customized pergola that allows them to use the roof in all seasons. The plans also call for custom planters and LED lights, as well as skylights to bring some much-desired light into the apartment’s interior.

Drawings in hand, the couple reached out to Bolster—a New York City company that has designed a transparent and enjoyable process for NYC homeowners doing major renovations—to find the right contractor. Bolster contractor Aaron Borenstein supplied the winning bid at $412,746, or $533 per square foot.  (Click here to view the detailed bid.)

The Bolster renovation team will begin work in late November, with an anticipated completion date in late March, as the homeowners want to be able to enjoy their revamped outdoor space by next spring. Read on to learn more about what renovating a rooftop through the winter entails—and how much each aspect of the project will cost.

Note: The following photos are from a previous Bolster rooftop renovation; read more about that project here




The logistics of renovating an outdoor space in the winter  

Rooftop projects can be logistically challenging, so they require thorough pre-construction planning, Borenstein explains.

“Because of the time of year, we have to carefully choreograph this,” he says. “It’s fun to figure out with the architect how we can formulate everything to make it buildable within the parameters of the project.”

Advance planning is also necessary given that all materials must be transported to the roof. Borenstein notes that thankfully, the building has an elevator that the construction team can use, but they will have to carry materials up two flights of stairs in order to reach the roof. “Wind and weather are really my only two concerns,” he says. Delays due to extreme winter weather are a possibility, but will only affect the project’s timeline, not its costs.

The largest line item on the budget is a customized, stainless steel pergola, which can be opened in the summer and completely closed in the winter, creating a weatherproof cabana. The pergola, which is pre-fabricated offsite, and its installation, which involves welding it onto the roof, will cost $45,500; the inclusion of its custom folding glass doors costs $3,000.

For a striking contrast with the stainless steel, part of the rooftop deck will include tiles made of custom ipa—a type of Brazilian wood—as well as pavers and bluestone steps ($24,937).

Beneath the pergola, the construction team will install kitchen cabinetry ($1,950), a grill station ($1,300), refrigerator ($1,200), and countertops ($1,200). Naturally, these materials and appliances will be weatherproof. Bolster co-founder Anna Karp says, “It’s a very good value for the money. An outdoor kitchen can be weather-resistant and look good without breaking the bank.”

Facilitating smooth transitions between indoor and outdoor spaces

The roof is reached via a bulkhead—the structure through which you take the stairs to the top—which will be reworked to create a more seamless transition from the indoors to the outdoors.

The Bolster team will start with a demolition of the bulkhead’s existing metal siding ($21,500), and later install windows and nana doors ($10,500)—that is, foldable glass doors—that will make it possible for the homeowners to enter the pergola directly from the bulkhead. The area can be completely sealed in the winter, and foam insulation and a water shield ($1,200) will keep them cozy as they enjoy all the rooftop’s features even during the coldest months.

In the warmer weather, the roof will become lush and vibrant. Custom ipa planters, large enough to hold trees, will be added along the entire perimeter ($13,200), along with a fence and trellis ($11,700), and a long bench with a hydraulic hinge for additional storage ($6,100). A key element of the terrace is a shower, which, with the help of the planters, will create a very private outdoor space for the couple to enjoy during the scorching summer months.

To care for the flora, an automatic watering system with drip irrigation will be installed, and the construction team will put in LED lights so that the landscaping work can be admired at night. The plumbing and electrical work will cost $21,950 total. As Borenstein explains, setting up the latter will be fairly simple, but “plumbing is a little more tricky—we’ll have to tap through the roof and into the master bathroom to access the plumbing supply.”

Brightening the interiors

A rooftop renovation can be an opportunity not only to revamp your outdoor space, but also to make some changes to interiors, as well. In this case, the homeowners have already converted what was once a rather industrial-looking loft into a cozy and welcoming space, but it could be further improved with more natural light. The addition of skylights—which will be strong enough to be walked on while people are on the roof—will brighten the inside of their home, and bring a little of the outside in.

The skylights are a custom, bespoke item, Karp explains, and their installation is complex. Borenstein’s team will have to build square curbs on the roof, and then remove two roof rafters. Once the skylights are delivered, they will create the openings and then install them on the same day. “This way, we won’t have to worry about temporary weather protections,” Borenstein says. “It’s untraditional, but it’s the best solution here.”

Furthermore, since only a small area will be affected by this phase of the project, the homeowners will not have to leave their home while the work is underway. The necessary framing and repair work for the roof as a whole will run about $31,475, while the installation of skylights will cost $34,000

Overall, Karp says, the renovation will result in a clean, elegant space for the homeowners to enjoy. “It’s a very well thought through, elegant use of indoor and outdoor space,” she says. “And it’s a good investment in terms of the appreciation of property. The homeowners really thought about what they wanted.”  

Every year, New Yorkers waste over $700M following the usual renovation process. Bolster is different, using a scientific approach to match you with the highest-quality professionals and financially guarantee your project is delivered beautifully for a fair price - all at no extra cost.

To start your major home renovation project, visit or call (929) BOLSTER.

More from Bolster:

More articles in The Winning Bid series

Why are high-end bathrooms so low-tech? 

Here's how long it takes to gut renovate a three-bedroom apartment in NYC

Should you hire an architect or a contractor first? 

How to find a great contractor in NYC

Alanna Schubach

Contributing writer

Contributing editor Alanna Schubach has over a decade of experience as a New York City-based freelance journalist.

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