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September in Massachusetts is one of my favorite times of year. 🍎🍂 Summer isn’t quite over, but fall starts sneaking in — cider donuts, football Sundays, fairs, apple picking, and the first hints of foliage. And there is SO much happening this month. I rounded up some of my favorite September happenings, restaurants worth trying, new spots to check out, weekend getaways, football-watching spots, and plenty of ideas to kick off your fall bucket list. Basically, consider this your shortcut for the next time the group chat asks, “What should we do this weekend?” 👀 Save this one for later + send it to your favorite person to explore Massachusetts with. 🍁 Comment FALL and I’ll send you my full 2026 Massachusetts Fall Guide packed with even more local favorites, day trips, events, and things to do this season. I’m @sellhomeswithjackie, a Massachusetts local and real estate agent sharing the best of life in Metrowest + Central MA (between school drop-offs, football/baseball fields, and helping people make moves 🏡). Follow along for more local recs! #massachusetts #massachusettsevents #massachusettslocal #massachusettsrealestate #massachusettsrealtor

Trying to decide between Greater Boston or Greater Worcester before you buy? 👀 Here’s the thing: there isn’t necessarily a “better” choice. There’s a better choice for YOU. When I’m helping Massachusetts buyers figure out where they should focus their home search, these are some of the biggest things we talk about: 🏙️ GREATER BOSTON You may be prioritizing: → A shorter commute into Boston → More access to public transportation → Walkability → Restaurants, shopping & entertainment nearby → Proximity to major employers → Being closer to the city But depending on the town and your budget, that can mean compromising on square footage, yard size, privacy, condition, or price. 🌳 GREATER WORCESTER / CENTRAL MA You may be prioritizing: → More house for your budget → Larger lots & more outdoor space → Quieter neighborhoods → Garages, home offices & bonus spaces → More options for move-up buyers → Access to major routes like the Mass Pike, 495, 290 & 146 The tradeoff? You may be farther from Boston. So instead of asking: “Where should I buy?” Start by asking: What do I want my everyday life to look like? How often do you actually commute? Would you rather have a 20-minute shorter commute or an extra bedroom? Would you trade walkability for a bigger backyard? Do you need to be near the city — or just need reasonable access to it? And how long do you see yourself staying in your next home? Once we answer those questions, the map usually starts getting a LOT smaller. 🙌 And sellers — this matters for you, too. Understanding what today’s Massachusetts buyers are prioritizing helps us figure out who your likely buyer is, what features of your home we should be highlighting, and how to position your property in the market. If you're thinking about buying OR selling in Massachusetts and aren't sure where you fit into today's market, send me a message. I'd love to talk it through with you! I'm @sellhomeswithjackie, a Massachusetts Realtor helping people buy and sell throughout Metrowest & Central Massachusetts. Follow along for Massachusetts real estate, local towns, homes and everything in betwee

CONTACT JACKIE CRAWFORD-ROSS