MONROE COUNTY · MIDDLE SMITHFIELD TOWNSHIP · EAST STROUDSBURG
Winona Lakes is a private, non-gated residential community near East Stroudsburg, established around 1989, set mostly in Middle Smithfield Township, Monroe County, with a small section that extends into Lehman Township in Pike County. The setting is wooded, with lots that average a little under an acre and a half, and the community sits off Route 209 near Interstate 80 in the East Stroudsburg School District, which makes it as commuter-friendly as it is recreational. It is built around six private lakes used for swimming, fishing, and non-motorized boating such as canoeing, kayaking, and rowing. The amenity package is unusually broad for a community this size: an indoor pool open year-round and an outdoor pool in season, the community's own ski slope that runs when weather permits, a clubhouse that anchors year-round events, tennis courts, a basketball court, and three playgrounds. Its eastern-Pocono location also puts owners close to Shawnee Mountain, the Delaware Water Gap, and Bushkill Falls, with the wider Pocono recreation network an easy drive away.
✓ STR Allowed — Township Permit + Registration (verify by address)
Short-term rentals are permitted at Winona Lakes. Middle Smithfield Township allows short-term rentals by annual permit, and the association allows them with mandatory registration and a rental agreement filed for each stay, along with a yearly assessment on properties operated as short-term rentals. One important condition for investors: the community amenities, including the lakes, pools, and playgrounds, are reserved for owners and are not available to short-term rental guests. A small part of the community lies in Lehman Township, Pike County, which does not issue new short-term rental licenses, though existing licenses may be grandfathered, so buyers must confirm which township their specific property falls in. Verify the current rules with the association before purchasing.
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A wooded lake community near East Stroudsburg with six lakes, indoor and outdoor pools, and its own ski slope. Short-term rentals are permitted with conditions. Kerry can help you find the right home here.