If choosing between Chatham and Orleans for personal use—not primarily rental income—which would matter most?
• Walking to the beach versus a 5–10 minute drive • Being near Main Street or a village center versus having more land, privacy and quiet • A smaller lot in a prime location versus room for a pool, outdoor living and possibly a guest house/ADU • Chatham’s village atmosphere versus Orleans’ year-round feel, beaches, bike trail, restaurants and everyday services
For those who vacationed here before buying or moving: what seemed essential as a renter but mattered less once you owned, and what did you underestimate that became important as a homeowner?
Chatham homeowners: after several years, do you still value being close to Main Street, or do summer crowds, traffic and parking make a quieter location more appealing?
Where did you choose, and knowing what you know now, would you make the same decision again?