Grieve It or Leave It? Taxes, Insurance, and Today’s Buyers

Tax grievances, Real Estate Roundtable
Getty Images

With tax grievance season fast approaching in Nassau County and Suffolk County, how are property taxes, along with rising insurance costs, impacting deal momentum and buyer decision-making right now? Do you advise your clients to grieve their taxes if they are putting their home on the market? 

Ricardo Pena
THE AGENCY
SOUTH SHORE 

Homeowners often overemphasize aesthetic features and amenities when valuing their homes, neglecting the significant impact of property taxes and insurance costs on affordability. A home’s true value is tied to a buyer’s purchasing power, which is severely eroded by rising property taxes and insurance premiums, which in particular have increased over 50% since 2021. Unlike fixed interest rates, these costs are not fixed and rise annually, potentially decreasing a buyer’s purchasing power by 10-20% in high-tax areas. This pressure makes buyers highly analytical and apprehensive. I recently saw a property sitting on the market because of extremely high taxes. I connected my hesitant buyer with a tax grievance expert who projected a $10k tax reduction, giving the buyer the comfort to move forward, and we secured the sale. Sellers who are advised to investigate tax grievances can generate more interest and potentially achieve a better sales price. The grievance process is transferable, making it a worthwhile asset for both homeowners and potential buyers. 

Irene Rallis
DOUGLAS ELLIMAN
MANHASSET

Property taxes and rising insurance costs, particularly for waterfront properties, directly impact purchase price and overall affordability. Today’s buyers are highly payment-sensitive and evaluate taxes and insurance just as closely as interest rates. When carrying costs are elevated, buyers adjust their offer price accordingly or shift their search to homes with more favorable annual expenses. I consistently advise sellers to grieve their taxes each year. Even modest reductions strengthen a home’s competitive position and improve long-term marketability. If a homeowner has not grieved for several years, buyers often factor in the two- to five-year timeline it may take to achieve meaningful tax relief and price that delay into their offer. This frequently results in a requested credit or downward price adjustment to offset projected carrying costs. Proactively grieving taxes signals responsible ownership and eliminates a potential negotiation hurdle. In a market where buyers carefully analyze total monthly obligations, preparation, and transparency matter. Sellers who address taxes and insurance upfront protect their value, preserve leverage, and maintain deal momentum.

Molly Deegan
BRANCH REAL ESTATE GROUP
SEA CLIFF 

Tax grievance season always flips a little mental switch for Long Island buyers. Right now, I’m seeing people walk into showings loving the house, and then pull out their phone to do the math. Between property taxes and rising insurance premiums, the monthly carrying cost has become the conversation. It’s not killing deals, but it is slowing down decision-making. Buyers are more selective, and they’re comparing homes more carefully. Insurance has added another layer. Premiums are up, underwriting is tighter, and buyers want answers early—sometimes before they even make an offer. When a seller can say, “Here’s the tax history, here’s the insurance reality,” everything moves more smoothly. As for grieving before listing? In most cases, absolutely. A successful grievance is one of the cleanest ways to make a home more marketable. Lower taxes don’t just look good on a listing sheet—they expand the buyer pool and make the monthly numbers work. Even a pending grievance helps. It tells buyers this home has been thoughtfully managed. On Long Island, confidence drives momentum. Clear taxes and realistic insurance expectations keep deals moving. 

Ryan Springer
THE CORCORAN GROUP
CUTCHOGUE 

Property taxes and rising insurance costs are definitely part of the conversation right now, but I’m finding they impact psychology as much as pricing. Buyers are more payment-focused than ever – especially in the North Fork market – so higher monthly carrying costs can slow momentum or narrow the buyer pool if a property isn’t positioned correctly. Instead of seeing deals fall apart, I’m seeing buyers become more selective and analytical, comparing tax lines and insurance quotes closely before committing. From a listing standpoint, I don’t automatically advise sellers to grieve their taxes prior to going to market. A grievance can be beneficial long-term, but it doesn’t always translate into immediate value or faster negotiations, and timing can complicate disclosures or create unrealistic expectations. My approach is to educate both buyers and sellers on the full cost picture and price strategically within that reality. If a property’s taxes are significantly out of line with comparable homes, I’ll discuss the grievance process as part of a broader strategy — but it’s not a blanket recommendation. 

Catherine Davis
THE GOLD COAST TEAM
SERHANT.
NORTH SHORE 

While tax grievance season gets attention in Nassau and Suffolk Counties, I wouldn’t say the timing itself changes deal dynamics — these conversations happen year-round. Well-prepared buyers are discussing buying power with their lenders before touring homes, which allows them to stay within an appropriate tax range and avoid surprises later. Transparency around the full monthly payment (principal, interest, taxes, and insurance) is what keeps transactions steady. For buyers operating within tighter budgets, those numbers carry more weight upfront, whereas at higher price points, there is often more financial flexibility. If a property’s taxes are higher than average for the area, a seller initiating the grievance process in good faith can serve as an incentive, giving buyers visibility into potential savings as they evaluate long-term ownership costs and determine their offer strategy.