5 Wildebrook Rd
Medway, MA, 02053 $ 1,349,000
Bedrooms5 Baths3.1 Sq 4,124 Monthly Estimate*
$ 8,518
for $1,349,000 with 5 bedrooms and 3 full baths, 1 half bath. This 4,124 square foot home was built in 1997 on a lot size of 1.06.
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.
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List ByAlison SteevesListing Agent
Jack Conway Cape Cod - SandwichBroker
Affordability Calculator
- Monthly Principal & Interest
- $8,518
- Monthly Property Taxes
- $1,132
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Medway, MA
Average List Price $873,495
Percent of Sale Price 35%
About Medway, MA 13,225 Population
6% Since 2002
$ 115,431 Median Income
43.95 Median Age
39% Households with Children
Trends Information provided by ATTOM Data Solutions.
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Pricing History| Date | Price | Price Change | Description |
|---|
| 9/23/2026 | $1,349,000 | | Listed Price |