Most Expensive Places to Live on Long Island

Luxury oceanfront home near the beach in Southampton — A luxury oceanfront home near the beach in Southampton highlights the extraordinary value of real estate in the Hamptons. Limited waterfront land and sustained high-end demand have helped communities like this remain among the most expensive places to live on Long Island. Coastal access continues to be a major driver of premium home prices across the South Fork. File photo: LoveMetaverse, licensed.

Long Island has long been known for its high cost of living, but some communities stand far above the rest when it comes to home prices, property taxes, and the income typically associated with ownership in these markets.

Using a combination of housing market data, tax patterns, and broader cost-of-living estimates, LongIslandGuide.com reviewed some of the most expensive places to live across Nassau and Suffolk counties.

Because luxury real estate can move quickly, exact rankings and pricing can shift from season to season. The communities below are consistently among Long Island’s costliest residential markets.

1. Sagaponack (South Fork, Suffolk County)

Sunset over the vineyards at Wölffer Estate Vineyard in Sagaponack, one of the East End’s best-known wine destinations. The surrounding hamlet is defined by ocean access, large estates, and protected agricultural land that help keep housing supply limited. File photo: Cnicolestudio, licensed.

Recent market snapshot: Median home values often reach the mid-$6 million range or higher
Typical property taxes: Commonly $45,000+ annually on high-value homes
Estimated cost-of-living index: About 260 (U.S. average = 100)
Estimated income associated with comfortable ownership: Roughly $900,000/year

Sagaponack routinely ranks among the wealthiest ZIP codes in the country. Oceanfront estates, zoning constraints, farmland preservation, and very limited inventory keep prices exceptionally high.

2. Water Mill (Hamptons, Suffolk County)

The historic windmill in Water Mill stands as one of the East End’s most recognizable landmarks. It reflects the hamlet’s agricultural past, even as Water Mill has become one of the Hamptons’ most sought-after luxury residential markets. File photo: Little Vignettes Photo, licensed.

Recent market snapshot: Median home values often fall around $5.2 million
Typical property taxes: Frequently $40,000+ annually
Estimated cost-of-living index: About 250
Estimated income associated with comfortable ownership: Roughly $750,000/year

Known for sprawling estates and proximity to Southampton Village, Water Mill combines rural privacy, beach access, and easy reach to other South Fork destinations.

3. Old Westbury (North Shore, Nassau County)

The historic mansion at Old Westbury Gardens reflects the grandeur of Long Island’s Gold Coast era. Estates, large lots, and a long reputation for exclusivity continue to shape Old Westbury’s high-end housing market. File photo: Joe Trentacosti, licensed.

Recent market snapshot: Median home values often reach about $3.8 million
Typical property taxes: Commonly $60,000+ annually
Estimated cost-of-living index: About 240
Estimated income associated with comfortable ownership: Roughly $650,000/year

A historic Gold Coast community featuring grand homes on multi-acre properties, Old Westbury remains one of the most prestigious residential addresses on Long Island. Property taxes here are also among the region’s highest.

4. East Hampton Village (Suffolk County)

A sprawling estate near Main Beach in East Hampton showcases the luxury lifestyle associated with Long Island’s South Fork. Beach access, privacy, and limited supply help keep local real estate among the most valuable in New York State. File photo: AntonioCarlos, licensed.

Recent market snapshot: Median home values often reach about $3.2 million
Typical property taxes: Frequently $35,000+ annually
Estimated cost-of-living index: About 235
Estimated income associated with comfortable ownership: Roughly $600,000/year

East Hampton Village benefits from sustained demand, prestigious addresses, and close access to beaches, boutiques, restaurants, and cultural institutions. Pricing can vary widely between village properties and larger estate areas nearby.

5. Brookville (North Shore, Nassau County)

Coe Hall at Planting Fields Arboretum State Historic Park in Upper Brookville — Coe Hall at Planting Fields Arboretum State Historic Park in neighboring Upper Brookville reflects the broader Gold Coast character of the Brookville area. Large estates, private roads, and wooded properties help make Brookville and nearby villages some of Nassau County’s most exclusive addresses. File photo: Joe Trentacosti, licensed.

Recent market snapshot: Median home values often reach about $2.9 million
Typical property taxes: Commonly $55,000+ annually
Estimated cost-of-living index: About 230
Estimated income associated with comfortable ownership: Roughly $575,000/year

Home to large estates and private institutional campuses, Brookville offers seclusion on the North Shore while remaining within commuting distance of Manhattan and the rest of New York City.

6. Sands Point (Nassau County)

Execution Rocks Lighthouse off the coast of Sands Point — Execution Rocks Lighthouse stands in Long Island Sound off the coast of Sands Point on the North Shore. The village is known for waterfront estates, historic mansions, and a long-standing Gold Coast reputation. File photo: Joe Trentacosti, licensed.

Recent market snapshot: Median home values often reach about $2.7 million
Typical property taxes: Frequently $50,000+ annually
Estimated cost-of-living index: About 225
Estimated income associated with comfortable ownership: Roughly $540,000/year

Waterfront estates and historic mansions define this Gold Coast enclave. Desirable shoreline property and a limited number of large residential parcels help support premium prices.

Key Factors Driving High Costs

Several factors consistently push Long Island’s most expensive communities to the top of the market:

Limited land availability, especially near the water
Beach, bay, harbor, or Sound access
Proximity to New York City
Historic estate zoning and large-lot requirements
Strong school district reputations
Persistent demand from affluent regional, national, and international buyers

Why Long Island Remains One of America’s Costliest Regions

Even outside these ultra-premium enclaves, Long Island’s property taxes, insurance costs, and housing prices routinely rank among the highest in the country.

For many residents, the decision to live here reflects a trade-off between affordability and access to beaches, schools, downtown villages, cultural institutions, commuter rail service, and relative proximity to Manhattan.

Methodology

This ranking was compiled using recent housing market data, municipal tax patterns, and cost-of-living estimates across Nassau and Suffolk counties. Figures are approximate and meant to illustrate relative cost, not quote exact purchase or ownership costs for any single property. Real estate conditions, tax bills, and affordability benchmarks can change, so readers should check current local data before making housing decisions.

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