Long Island's South Shore Investor Market Runs on Numbers and Pricing Discipline

Written by:

Alejandra Rodriguez

Date:

17 Jun 2026

Share

Share via Facebook

Share via Linkedin

Share via X

Copy to clipboard

Property values that have climbed from $30,000 in the 1990s to between $325,000 and $480,000 today tell only part of the story on Long Island’s South Shore. For the investors and agents who work these markets daily, the real drivers are far more nuanced, and right now, they point to a market where pace is slowing, and pricing discipline matters more than it has in years.

Kerri Gottlieb, a licensed real estate professional with EXIT Realty All Pro, has spent 35 years working the South Shore communities of Suffolk County, including Bellport, Mastic Beach, Shirley, and Central Medford. With roughly 95% of her current business coming from investors, her perspective offers a ground-level read on a market that outside observers often misread.

The Tax Factor

Before price per square foot or rental yield, the first filter for any serious investor in this market is property taxes. On Long Island, that conversation is unavoidable.

Gottlieb says the sweet spot for an investor is $7,500 or less in annual taxes. What makes the tax picture especially complicated is its inconsistency. Two identical floor plans on the same block might carry tax bills of $6,200 and $11,000, respectively, a gap that defies easy explanation but directly affects investment returns.

That inconsistency has grown more pressing recently. Property taxes in the Town of Brookhaven rose 28% in a recent assessment cycle, a development Gottlieb believes will push more homeowners to list. Insurance costs are adding further pressure, with some carriers dropping coverage in the area altogether. “I think the economy is what’s going to force people to list their houses right now,” she says.

Who’s Buying and Why

The investor profile Gottlieb works with is relationship-driven and numbers-focused. She has maintained active working relationships with several investors for over two decades, and that familiarity shapes how deals get done.

“I know what they like, I know what they’ll buy, and I know the numbers they’ll pay,” she says. When the numbers work, buyers move. When they don’t, they wait.

That discipline has been on display recently in the process of contracting the sale of a 21-property rental portfolio from a retiring investor to another long-term client. The deal was structured as a package – all or nothing – and it closed. It’s the kind of transaction that only happens when both sides have a clear-eyed view of what the assets are worth.

For investors entering the market today, Gottlieb’s recommendation is specific: target tenant-occupied properties, particularly those with Section 8 voucher holders. These tenants tend to stay for years, rents can be increased over time, and income is guaranteed by the program, even if a tenant becomes temporarily unable to work. “It’s pretty much like an insurance policy,” she notes.

Out of ten properties she sells, roughly eight end up as rentals. The fix-and-flip strategy exists but plays a secondary role in this market.

Demand Persists, But the Pace Is Slowing

The competitive intensity that defined the post-COVID market hasn’t fully faded, but it’s moderating. A recent Bellport listing illustrated both the continued demand and the emerging complexity. The renovated property sat through an open house with little initial activity, then drew 12 offers – several over asking price – after a modest price reduction. It went under contract at $550,000.

Of the three cash offers submitted, none were straightforward. Gottlieb explains that buyers were either in contract on their own property and expected to have cash at closing, or they wanted to do subject-to financing. The seller passed on all three and accepted a financed offer from a buyer who already had a mortgage commitment. “To me, that’s as good as a cash offer,” she says.

That nuance matters. In a market where “cash offer” can mean several different things, understanding the actual strength of each bid is part of the job.

Approximately 70% of active buyers in these South Shore communities are coming from the five boroughs, primarily Brooklyn. Local buyers, people who grew up in the area, moved away, and are now looking to purchase, make up much of the remainder, with some coming from Nassau County as well.

What’s Sitting and What’s Moving

The gap between listings that sell quickly and those that stall has widened in recent weeks, and the explanation is straightforward. Inventory has been tight across Long Island, and these South Shore communities are no exception. New construction exists but isn’t substantial enough to meaningfully change the supply picture. What is starting to change is the pace of sales.

“Six months ago, you’d list something and have a line out the door with multiple offers,” Gottlieb observes. “I’ve seen a lot of price changes over the past month, and I’ve seen properties sit on the market.”

Her read on what separates listings that move from those that don’t comes down to one variable: price. “There’s no bad houses, just bad prices,” she says, a philosophy she applies regardless of location, condition, or functional issues.

Properties that linger tend to be overpriced, often because sellers are anchored to the multiple-offer environment of recent years. Gottlieb recently had to relist a property after a seller declined a full-price offer, believing the market would deliver more. It didn’t.

An Appraisal Problem May Be Coming

As prices climb and the market softens at the margins, appraisals may become a more common source of friction in financed deals. Most of Gottlieb’s current transactions are cash, which has insulated her business from this issue so far. But she expects appraisal gaps to become a more frequent deal-killer for buyers using conventional or FHA financing.

“I think we’re going to start having a problem with appraisals not coming in,” she says. For cash investors, this may represent an advantage: the ability to close without the contingency risk that financed buyers carry.

A Market That Rewards Discipline

What emerges from 35 years of working these communities is a market that has always rewarded discipline over speculation. Taxes, conditions, and pricing have always mattered here. What’s changed is the speed at which listings attract competitive offers, and that speed is clearly declining.

For investors who know their numbers and have built long-standing relationships with agents who understand the territory, the South Shore still offers viable opportunities. But the margin for error is narrowing. Sellers who price accurately and buyers who move decisively on sound numbers will continue to close deals. Those still operating on the assumptions of 2022 and 2023, expecting bidding wars and premium pricing regardless of fundamentals, are finding that the market no longer cooperates.

About the Expert: Kerri Gottlieb is a licensed real estate professional with EXIT Realty All Pro, with 35 years of experience serving the South Shore communities of Suffolk County on Long Island, including Bellport, Mastic Beach, Shirley, and Central Medford. Approximately 95% of her current business involves investor transactions.

This article is based on information provided by the expert source cited above. It is intended for general informational purposes only and does not constitute legal, financial, or real estate advice. Readers should conduct their own research and consult qualified professionals before making any real estate or financial decisions.