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Listing broker remarks

Set along the scenic Skyline Trail, this fully renovated home offers refined finishes, abundant natural light, and a seamless open layout. A long, estate-style concrete approach creates a striking sense of arrival, leading into a thoughtfully updated interior featuring porcelain tile flooring, modern upgrades, and two fireplaces that add warmth and architectural character. A versatile finished bonus space off the main living area provides flexibility, ideal as a family room, studio, fitness area, or easily converted back to a two-car garage. A charming barn offers additional space for equestrian pursuits or curated hobby use without overpowering the setting. Included is a separate buildable lot, presenting exceptional opportunity for future development, guest accommodations, or long-term investment. Surrounded by mature rhododendrons and natural landscape, the home offers exceptional privacy, a peaceful setting, and a true retreat-like atmosphere.— First NationWide Realty Inc.

Key details

  • 2,244 sq ft
  • 7.63 acres
  • 4 beds
  • 2 baths
  • 1969 built
  • $257 / sq ft
  • $3,216 2025 taxes
MLS #
7⁠3⁠5⁠1⁠3⁠0⁠6⁠8⁠
Last updated
Address
506 Skyline Trl
Town
Chester, MA
ZIP
01011
Deed (Bk/Pg)
21931 / 417

Historic designations

MACRIS Inventory
Chester Agricultural District

What this means for buyers →

Map

Neighborhood: Chester

National Historic Landmark

Federally designated as nationally significant — the highest U.S. historic recognition. Section 106 review applies to federal undertakings affecting the property.

National Register

Listed on the National Register of Historic Places. Owners may qualify for the 20% federal Historic Rehabilitation Tax Credit on certified rehabilitation work.

State Register

Listed on the Massachusetts State Register of Historic Places.

Local Historic District

Inside a Local Historic District. Exterior changes visible from a public way require approval from the local historic district commission.

Local Landmark

Individually designated by the town as a local landmark. Exterior alterations require commission approval.

MACRIS Inventory

Documented in MACRIS, the state historic inventory. Informational only — no regulatory constraints.

Article 85 (Boston)

Subject to Boston Article 85 demolition-delay review, which can pause demolition of buildings 50+ years old for up to 90 days.