Most Expensive Places to Live

A luxury oceanfront home near the beach in Southampton highlights the extraordinary value of real estate in the Hamptons. Limited waterfront land and global demand have made communities like this among the most expensive places to live on Long Island. Coastal access continues to drive record-setting property 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 housing prices, property taxes, and the income required to maintain a comfortable lifestyle.

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

Below are the communities where living comes at the highest price.

1. Sagaponack (South Fork, Suffolk County)

Sunset over the vineyards at Wölffer Estate in Sagaponack
Sunset over the vineyards at Wölffer Estate in Sagaponack, one of Long Island’s most prestigious wine destinations. The Hamptons estate is known worldwide for producing premium rosé and estate-grown wines. Long Island’s North and South Fork vineyards have helped establish the region as a major force in American winemaking. File photo: Cnicolestudio, licensed.

Median Home Price: ~$6.5M
Typical Property Taxes: $45,000+ annually
Cost of Living Index: ~260 (U.S. average = 100)
Income Needed to Live Comfortably: ~$900,000/year

Sagaponack consistently ranks among the wealthiest ZIP codes in America. Oceanfront estates, agricultural land restrictions, and limited housing supply keep prices exceptionally high.

2. Water Mill (Hamptons, Suffolk County)

The historic windmill at Water Mill
The historic windmill at Water Mill stands as one of Long Island’s most recognizable East End landmarks. Dating back to the 19th century, the structure reflects the agricultural roots of the Hamptons before the rise of luxury estates. Today, it remains a symbol of the region’s heritage and scenic beauty. File photo: Little Vignettes Photo, licensed.

Median Home Price: ~$5.2M
Typical Property Taxes: $40,000+
Cost of Living Index: ~250
Income Needed: ~$750,000/year

Known for sprawling estates and proximity to Southampton Village, Water Mill offers luxury living with rural privacy.

3. Old Westbury (North Shore, Nassau County)

The historic mansion at Old Westbury Gardens
The historic mansion at Old Westbury Gardens reflects the grandeur of Long Island’s Gold Coast era. Built in the early 20th century, the estate showcases the immense wealth that once defined North Shore communities like Old Westbury. Today, it remains one of the region’s most iconic architectural and cultural landmarks. File photo: Joe Trentacosti, licensed.

Median Home Price: ~$3.8M
Typical Property Taxes: $60,000+
Cost of Living Index: ~240
Income Needed: ~$650,000/year

A historic Gold Coast community featuring grand estates on multi-acre properties. Property taxes here are among the highest on Long Island.

4. East Hampton Village (Suffolk County)

A sprawling estate near Main Beach in East Hampton
A sprawling estate near Main Beach in East Hampton showcases the luxury lifestyle of Long Island’s South Fork. Ocean proximity, privacy, and expansive grounds make properties here among the most valuable in New York State. East Hampton continues to attract high-profile buyers seeking exclusive coastal living. File photo: AntonioCarlos, licensed.

Median Home Price: ~$3.2M
Typical Property Taxes: $35,000+
Cost of Living Index: ~235
Income Needed: ~$600,000/year

Seasonal demand and international buyers continue to push prices upward.

5. Brookville (North Shore, Nassau County)

Coe Hall at Planting Fields Arboretum in Upper Brookville
Coe Hall at Planting Fields Arboretum in Upper Brookville reflects the grandeur of Long Island’s historic Gold Coast estates. Built during the early 20th century, the mansion symbolizes the immense wealth that shaped North Shore communities. Upper Brookville remains one of the most exclusive and expensive places to live on Long Island. File photo: Joe Trentacosti, licensed.

Median Home Price: ~$2.9M
Typical Property Taxes: $55,000+
Cost of Living Index: ~230
Income Needed: ~$575,000/year

Home to large estates and private campuses, Brookville combines exclusivity with proximity to Manhattan.

6. Sands Point (Nassau County)

Execution Rocks Lighthouse stands in Long Island Sound off the coast of Sands Point on the North Shore.
Execution Rocks Lighthouse stands in Long Island Sound off the coast of Sands Point on the North Shore. The historic beacon has guided ships through these waters since the 19th century and remains a striking regional landmark. Sands Point is known for its waterfront estates and ranks among Long Island’s most exclusive communities.

Median Home Price: ~$2.7M
Typical Property Taxes: $50,000+
Cost of Living Index: ~225
Income Needed: ~$540,000/year

Waterfront estates and historic mansions define this Gold Coast enclave.

Key Factors Driving High Costs

Several factors consistently drive Long Island’s most expensive communities:

  • Limited land availability
  • Waterfront access
  • Proximity to New York City
  • Historic estate zoning
  • High-performing school districts
  • Demand from international buyers

Why Long Island Remains One of America’s Costliest Regions

Even outside the ultra-luxury enclaves, Long Island’s property taxes and housing costs rank among the highest in the nation.

For many residents, the decision to live here reflects a trade-off between affordability and access to beaches, schools, culture, and proximity to Manhattan.

Methodology

This ranking was compiled using recent housing market data, municipal tax records, and cost-of-living estimates across Nassau and Suffolk counties. Figures represent approximate averages and may vary by property size and location.