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Listing broker remarks

This five-bedroom Medway home stands out for what so many buyers want, but rarely find: a comfortable, well-finished home paired with a backyard that lives like a private retreat. The outdoor space is the showpiece, with a saltwater in-ground pool, raised spillover spa, expansive travertine terrace, pergola lounge area, natural-stone fire pit, open lawn, dedicated sport court, mature landscaping, privacy fencing, and large storage shed. It is a backyard built for real use—pool days, games on the court, dinner under the pergola, coffee on the deck, and nights around the fire. What makes it work so well is how naturally it connects to the main living spaces, giving the home an indoor-outdoor feel that is hard to duplicate in Medway. Inside, the layout is warm, open, and easy to live in. The kitchen features a large center island with seating, generous cabinetry, and a beverage station with wine storage and a beverage/wine cooler. The dining area and sun-filled family room connect comfortably, with hardwood floors, a two-story foyer, and a gas fireplace adding polish and warmth.The upper level includes the primary suite with walk-in closet and spa-style bath with soaking tub, double vanity, and glass-enclosed tiled shower with dual showerheads, plus a guest ensuite, three additional bedrooms, and second-floor laundry. The main level adds a home office with French doors and a mudroom with built-ins, while the finished basement offers flexible space for work, guests, fitness, movies, or play. Recent updates include a newer roof with transferable warranty, updated HVAC, new pool liner, recently installed whole-house water filter, washer and dryer replaced in 2025, new upstairs carpeting and stair runner, newly epoxied garage floor, and freshly sealed driveway. A rare Medway offering where the home and backyard come together to create an everyday lifestyle that feels anything but ordinary. Buyers and Buyers agents to verify.— Jack Conway Cape Cod - Sandwich

Key details

  • 4,124 sq ft
  • 1.06 acres
  • 5 beds
  • 3.5 baths
  • 1997 built
  • $327 / sq ft
  • $13,580 2026 taxes
  • HOA yearly
MLS #
7⁠3⁠5⁠7⁠9⁠5⁠9⁠3⁠
Last updated
Address
5 Wildebrook Rd
Town
Medway, MA
ZIP
02053
Deed (Bk/Pg)
22567 / 121

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.

Ch. 91 Waterways License

An active MassDEP permit for a dock, pier, seawall, or other structure on or over a Massachusetts waterway. Many older licenses are not digitized; this record is provided for reference only.

Massachusetts Great Pond

A Great Pond under M.G.L. Ch. 91 — the Commonwealth retains public rights to fish and navigate these state-designated waters. Private docks and other waterfront structures require a Waterways License from MassDEP.

Likely Great Pond

The MLS listing describes this property as being on a Great Pond, which would be a state-designated water body under M.G.L. Ch. 91. GIS data did not independently confirm the pond name — verification needed.