When is the best time to sell your home? Find out What Team Coyle Says

When is The Best Time to Sell Your Home?

Hindsight is Not 20/20

I know what you’re thinking – I should have sold my home last year when the market for residential real estate in Massachusetts was on fire.  A word to the wise – trying to time the market (i.e., when to buy or sell an asset) is a fool’s game. Even the legendary investor Warren Buffet would admit that he doesn’t have the faintest idea of how an asset will perform on a given day, week, month, or year.  Besides, if you are not ready to sell, then the notion of “should have” or “could have” is absurd.

Folks, selling your home is probably the largest and most important investment decision an individual/family will ever make in their lifetime.  So, take your time and carefully think it through before making a final decision. Also, don’t be a hero – seek professional advice.  Step one is to interview several notable real estate agents in your area and solicit their advice on how best to proceed.  Step two is you need to answer three basic questions.

1. Should You Stay or Should You Go?

Many homeowners have lived in their home/community for 10/15/20+ years. So, any decision that contemplates leaving all those memories behind is a difficult one at best. That’s why most people put off deciding until the last possible moment. The key here is to make an informed decision based on the facts so you can determine if it makes sense financially for you to “stay put” or to sell your home. Talk to a financial advisor or better yet – do it yourself.  No one knows your financial position better than you.

2. Where to Relocate?

If you decide it’s time to sell, the next question is where do you go? Remember the old adage – don’t quit your job until you have a new one. Well, the same rule applies for housing. Find a new home before you sell your old one. Start by making a list of features that you want your new home/community to have.  If you’re thinking about moving out-of-state, then ask one of the local real estate agents you interviewed in step one for advice or an agent referral. Compass real estate, for example, has a nationwide network of agents you can resource, and it’s doesn’t cost you a penny.

3. Should You Buy or Rent?

Now that you decided where you want to live, the next question is do you buy or rent? The answer, of course, is situation specific. Most of us understand the investment benefits of homeownership – the potential to build long-term equity (i.e., savings).  Renting, however, may be a more suitable option for you if affordability is an issue, or you just want to evaluate (test drive) living in a town/neighborhood before making a long-term financial commitment. Regardless of which option you choose, take your time, and make a decision that suits your needs. God-speed!

About TEAM COYLE

Team Coyle,  a professional group of real estate agents at Compass, has more than ten years of experience helping individuals and families buy and sell real estate in the Greater Boston Region of Massachusetts (primarily MetroWest).

Matt & Ying Coyle, Team Coyle — Compass agents in Wellesley

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Matt Coyle, REALTOR®
Address
161 Linden St, Suite 102
Wellesley, MA 02482

Methodology

TownRatings™ is a proprietary model developed by Team Coyle to provide homebuyers and sellers with a relative rating (assessment) of a town’s key characteristics, benchmarked against other Greater Boston towns. Ratings are based on publicly available data and Team Coyle’s on-the-ground expertise and are intended as a general guide only. Please consult a licensed real estate professional before making any real estate decisions. Ratings are current as of October 4, 2025.

RATING CATEGORIES

  • Quality of Schools: Based on Massachusetts Department of Elementary and Secondary Education (DESE) 2024 data, emphasizing Grade 10 MCAS English Language Arts and Mathematics proficiency rates and 4-year high school graduation rates. Together, these measures provide a snapshot of academic achievement and long-term outcomes.
    Scale: Above Average · Average · Below Average
  • Commute to Boston: Assesses commuting ease using travel time, distance, and in-town transit access. For towns with MBTA rail or subway service, commute times are measured to the line’s natural Boston endpoint (e.g., North Station, South Station, or Back Bay). For towns without in-town service, commute times are measured by car to Back Bay as the default reference point.
    Scale: Easy · Moderate · Challenging
  • Shopping & Dining: Reflects the density and variety of retail and restaurant options within a town or in adjacent hubs.
    Scale: Excellent · Good · Limited
  • Lifestyle: A general description a town's overall character (e.g., Upscale, Rural, Historic, Suburban, Urban/Vibrant).
  • Est. Annual Tax per $1M: The town’s residential property tax rate applied to $1,000,000 of value (as of the report date) for easy comparison.

HOW RATINGS ARE DERIVED

Ratings are determined using a blend of publicly reported data (e.g., DESE reports, MBTA schedules, municipal tax rates, business directories), mapping and transportation tools, and qualitative insights from Team Coyle agents active in these markets.

LIMITATIONS & DISCLAIMERS

  • Informational only; subject to change without notice.
  • No duty to update: Team Coyle and its agents are not obligated to refresh or revise ratings.
  • No warranties: Information is provided “as is” without warranties of any kind.
  • No liability: Team Coyle, its agents, and Compass are not liable for any losses, damages, or costs arising from use or reliance.
  • Not advice: not legal, tax, financial, educational, or transportation advice. Consult a licensed real estate professional/agent and other appropriate professionals.
  • Verify independently: Commute times vary (route/time/weather) — check MBTA schedules and test commutes. School offerings and performance change — confirm with districts and the MA Dept. of Elementary & Secondary Education. Amenities evolve — verify locally.
  • Third-party content not endorsed; accuracy not guaranteed. Trademarks belong to their owners.
  • Broker disclosure: Compass is a licensed real estate broker and abides by Equal Housing Opportunity laws.
  • Fair housing: Nothing here should be used to encourage or discourage housing decisions based on protected characteristics.