Every Monday, “06880” features 4 “Then & Now” homes: one that was torn down, and the home that replaced it.
There are many reasons why new owners opt for new construction. The house they bought may not fit their needs. It may be too small, architecturally outdated, or lacking modern amenities.
But there’s another reason: It was not maintained well.
For sellers who hope their home survives the wrecking ball, that’s one variable they can control.
Our friends at KMS Team at Compass know all about maintaining a home. They say:
Westport’s teardown issue isn’t just about developers. Deferred maintenance plays a role, too.
Plenty of buyers appreciate older homes, and see them as a more affordable way into town. But when years of deferred maintenance add up, renovating may no longer make financial sense, and the value shifts to the land.
Taking care of our older homes helps preserve the character of Westport, and gives the next buyer a reason to renovate rather than tear down.
Maintenance is preservation. Homeowners who consistently care for the fundamentals of an older home give future buyers the option to renovate and preserve it, rather than making the land itself the property’s greatest value. The goal is not to make an older home new. It is to keep it healthy.

This 1939 River Lane home has been expanded to 6 bedrooms. Its architectural details have been well maintained.
Maintaining a home does not mean constantly renovating it, or having the latest kitchen and bathrooms. It means taking care of the bones of the house — the roof, foundation, drainage, electrical, plumbing, heating and cooling systems, chimney, septic or sewer connection, and environmental and safety issues.
Cosmetic updates are relatively easy for a buyer to envision. What can become overwhelming is a house with years of deferred maintenance. An older kitchen can be charming; a failing roof, water intrusion, outdated electrical system and neglected mechanicals are much harder to overlook.
Buyers are much more willing to work with an older home when they believe the underlying house is sound.
We see buyers who genuinely appreciate Westport’s Capes, ranches and older colonials. They may be perfectly happy renovating a kitchen, opening up a floor plan or adding a primary suite. But when they start adding up a new roof, windows, HVAC, electrical, plumbing, drainage, mold remediation and structural work, the economics can quickly change.
At some point buyers stop asking, “How can I make this house my own?” and start asking, “Does it make more sense to start over?” That’s often how a perfectly appealing older home becomes viewed primarily for its land.
Owners should think of home maintenance as an ongoing program — not something to address right before selling.

This High Gate Road home looks fresh and appealing.
Start with the basics: Clean your gutters, keep water away from the house, address leaks immediately, service HVAC equipment, inspect the roof and chimney, maintain septic systems where applicable, watch for rot and insect damage, and periodically evaluate plumbing and electrical systems.
Keep trees and vegetation from damaging the house. Pay attention to basements and crawl spaces for moisture.
Save invoices, permits, warranties and information about major improvements. When it comes time to sell, being able to show buyers that a home has been consistently cared for creates confidence.
Fall is a good time to address maintenance issues. Focus on gutters and drainage, roof and chimney condition, heating system servicing, exterior wood and trim, tree limbs near the house, outdoor faucets and irrigation, and identifying any areas where water or ice could cause damage over the winter.
If you’re thinking about selling but have not done much maintenance, there are several steps to take. But putting money into cosmetic renovations before addressing deferred maintenance can be the wrong investment.
Don’t assume you need to renovate everything. First, look at the house the way a buyer and home inspector will. Identify significant structural, mechanical, environmental and safety issues first. Then prioritize the items most likely to frighten buyers, or make the cost of owning the house feel unpredictable.
A homeowner preparing to sell might be much better served spending money correcting water intrusion, repairing a roof, addressing electrical or plumbing concerns, servicing mechanical systems, removing mold or repairing exterior rot than installing a brand-new kitchen that the next owner may replace anyway.
Real estate agents can also help homeowners prioritize. The objective is to determine which improvements will give buyers confidence that the house is worth preserving.
(“06880” reports often on all aspects of Westport’s real estate market. If you enjoy our coverage — or anything else on our hyper-local blog — please click here, to support our work. Thank you!)












The app is in a soft launch phase. It teed off right here, at courses like Longshore and Rolling Hills Country Club.























