About this home

Price Improvement! First time buyers, investors, renovators, and village-lifestyle seekers should all pay attention to 57 Jermain Avenue. Set on the corner of Jermain and Oakland in the Sag Harbor Village Historic District, this circa-1938 legal two-family offers a rare combination of walkability, flexibility, income potential, and future upside. The property includes three-plus bedrooms, three full baths, a den, two kitchens, two living rooms, off-street parking, and room for a pool. Use it as a true two-family, live in one side and rent the other, create guest quarters, or explore conversion into a larger single-family village home. The long Oakland frontage adds presence, access, and design flexibility. Moments from Main Street, Mashashimuet Park, tennis, pickleball, and Otter Pond, this is an affordable village manse with real upside in one of the Hamptons' most beloved historic communities.

Facts and features

Schools

• Pierson Middle High School

  middle · 6-12 · 0.4 mi

  8

• Sag Harbor Elementary School

  elementary · K-5 · 0.5 mi

  8

• HARBOR WALDORF SCHOOL

  elementary · PK-K · 0.5 mi

• Ross School

  elementary · K-12 · 3.0 mi

• Ross School

  elementary · PK-12 · 3.3 mi

Price history

• Sep 23, 2026 · Price Changed$1,939,000
• Aug 6, 2026 · Relisted$1,949,000
• Aug 2, 2026 · Listing Removed$1,949,000
• Jun 22, 2026 · Price Changed$1,949,000
• Nov 15, 2025 · Price Changed$1,995,000
• Sep 17, 2025 · Price Changed$2,100,000
• Aug 20, 2025 · Listed$2,350,000
• Nov 10, 1997 · Sold$190,000

Tax history

• 2024$2,156 tax · $776,500 assessed
• 2023$2,135 tax · $776,500 assessed
• 2022$2,108 tax · $776,500 assessed
• 2021$2,121 tax · $776,500 assessed
• 2018$4,396 tax · $765,200 assessed
• 2017$4,396 tax · $765,200 assessed
• 2016$4,572 tax · $765,200 assessed
• 2015$4,685 tax · $765,200 assessed

Home value

$1,920,000

• Collateral Analytics$1,920,000
• Quantarium$1,965,056
• Cotality$1,819,200

Where it is