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Listing broker remarks

Tucked away at the end of a long private drive, 5 Winchester Road offers the rare combination of timeless Colonial living & a truly exceptional setting. Nestled on 1.7 acres of beautifully manicured grounds surrounded by mature trees, this property provides a sense of privacy and tranquility that is increasingly hard to find. Hardwood floors run throughout the entire home, complementing the classic Colonial floorplan designed for both comfortable living & entertaining. The first floor features a custom fieldstone fireplace in the family room, formal sitting room, formal dining room, and an eat-in kitchen with sliders leading to a deck overlooking the peaceful backyard. Upstairs are four bedrooms, including a spacious primary suite w/ private bath. The finished lower level adds valuable living space with a wet bar, dedicated home office, and room for recreation or gatherings. Offering the perfect balance of privacy, space, and nature-this is a place you'll love coming home to.— Berkshire Hathaway HomeServices Evolution Properties

Open Houses

Key details

  • 2,640 sq ft
  • 1.70 acres
  • 4 beds
  • 2.5 baths
  • 2003 built
  • $331 / sq ft
  • $10,232 2025 taxes
MLS #
7⁠3⁠5⁠3⁠6⁠5⁠0⁠7⁠
Last updated
Address
5 Winchester Rd
Town
Medway, MA
ZIP
02053
Deed (Bk/Pg)
20969 / 321

Map

Neighborhood: Medway

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.