Seeking Advice: Best Investment Markets Near Boston (<$1.5M, Lakefront Properties)

Location: Massachusetts (Greater Boston Area) Investment Strategy: Buy & Hold / Short-Term Rental Budget: Under $1.5M

Hey BP Community! 👋 I’m looking to expand my portfolio with a lakefront or lake-adjacent property within a 2-hour drive of Boston. Hoping to tap into the collective wisdom here for some market insights.   My Criteria: • Budget: Under $1.5M • Location: Within 2 hours driving distance of Boston • Property Type: Near/on a lake (considering both primary residence potential and rental income) • Strategy: Likely buy & hold, possibly exploring STR opportunities   What I’m Looking For: • Which lake communities have you found to be solid investments? • Any markets showing good appreciation trends vs. still undervalued? • Rental demand insights (both long-term and vacation rental markets)? • Towns/regions to avoid and why? • Seasonal vs. year-round rental considerations?   Areas I’m Already Considering: • Lake Winnipesaukee region (NH), Maine lake area • Berkshires lake communities (MA) • Southern Vermont lake areas • Connecticut lake towns   Questions for the Experts: 1. Are there any hidden gem markets I should be looking at? 2. How’s the vacation rental regulation landscape in these areas? 3. Any specific lakes/towns where you’ve seen strong ROI? 4. Winter rental demand - realistic or forget about it? Would love to hear from anyone who’s invested in lakefront properties in New England or has insights on these markets. Even if you haven’t invested but live in the area, local knowledge is super valuable! Thanks in advance for sharing your experiences! 🙏   Happy to return the favor with insights on Boston metro market if helpful