AI Listing Platform Launches for NYC Rentals

A new rental hub debuting in New York City is picking up inventory from top firms and squaring off with New York City’s legacy listing models.
A team including Canvas Property Group’s Robert Morgenstern and former NorthStar CEO Al Tylis on Thursday announced the launch of Sidewalk, an AI-powered platform that allows prospective tenants to search for their target apartments conversationally, rather than selecting pre-set filters.
The platform currently has about 4,000 listings for rentals in the city, about 40 percent of the roughly 10,500 available on StreetEasy at the time of publication. Most of those are supplied through Sidewalk’s partnership with brokerages such as Compass, Living New York and Real New York. It also teamed up with RealPlus, which will allow it to display rental listings from other firms like Serhant and Douglas Elliman.
Similar to Zillow’s goals of building a housing super app, Sidewalk aims to expand services, allowing tenants to pre-verify their identities and incomes before filing applications, find a guarantor and secure renter’s insurance.
“There are six or seven different vendors currently needed for a renter or an owner-operator to rent an apartment,” Morgenstern said. “There are separate logins and separate portals. Ideally, we want them embedded and less expensive for all of those people involved.”
On the broker side, Sidewalk doesn’t charge agents to upload exclusive rental listings, instead relying, in part, on agents purchasing other services and features on the platform to generate revenue. For agents, that could make the platform a welcome alternative to the current leader, StreetEasy, where it costs between $7 and $22 a day to advertise a listing.
“We won’t need to have the meter running on a rental broker per day per listing,” Morgenstern said.
Though the StreetEasy comparison is the obvious one to make, Morgenstern insisted that with Sidewalk, it’s not exactly apples-to-apples.
“I don’t think we’re trying to build a better StreetEasy,” Morgenstern said. “It’s a different economic model.”
One of Morgenstern’s partners on the platform, Atul Ajoy, added that while Sidewalk does have “some competition” with StreetEasy, the ultimate vision is to build an “end-to-end real estate platform.” That will eventually include for-sale listings, not just rentals.
Sidewalk is launching at a critical time for real estate listing platforms. are in the midst of a fight with brokerage and multiple listing service leaders over where and when listings should be advertised and who gets to make those rules. That battle has largely centered on for-sale listings, but overlaps with some New York City agents’ frustrations with the cost of using the dominant platforms for both sales and rentals.
The platform also comes as the city’s rental market has become tighter and more expensive, driven by a housing shortage. Concerns over a lack of available apartments from both brokers and tenants mounted after the city adopted a ban on broker fees, which some say has pushed listings off the market as landlords refuse, or can’t afford, to hire and pay a fee to rental brokers themselves.
Morgenstern is the founder and CEO of Canvas Property Group and its associated firms, whose recent deals include the $113 million purchase of the 150-unit Azure tower in Downtown Brooklyn with partner Tokyu Land US in 2024. Two years prior, Morgenstern partnered with Apollo Global Management co-founder Josh Harris in a $1 billion multifamily buying spree.
Tylis, now the CEO of Apollo Sports Capital, is also a member of Canvas’ board of directors.
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