Battered Dwight Gem Ready For Rehab

Thomas Breen photosThe owner of an historic Dwight Street home that has sat empty and derelict for two years has teamed up with a local architectural designer and historian to restore the property to its architectural roots.

Scott Healy, the former executive director of the Town Green Special Services District, owns the four-family, two-story home at 189 Dwight St. on a residential block around the corner from Amistad Academy that is lined with mid-19th century and early-20th century houses.

A former chair of the Dwight Community Management Team and one of the co-founders of the New Haven Urban Design League, Healy bought the home in 1999. He lived on the second floor while renting out the building’s two ground floor rooms until he moved to Chicago for graduate school in 2008. He now splits his time between Chicago and New Haven, taking some of the money he makes as a management consultant and pouring it into repair and restoration projects in the Dwight Street home, he said.

In January 2016, right as Healy had gathered enough money to fund a new HVAC system and a comprehensive rehabilitation of the property’s roof, one of the pipes on the second floor burst and flooded the entire house. Healy was in Boston visiting his family, and had recently discontinued the rentals in anticipation of the major renovations he had planned for the roof and heating.

“It looked like someone dumped a waterfall into the house,” Healy said as he remembered rushing back to the house two years ago to find water still trickling from the front door into the street.

For the past two years, Healy said, he has been wrestling with his insurance company and slowly refilling his coffers to fund his planned restoration of the building. He said that he is reluctant to sell the home to one of the city’s major real estate developers out of fear that they would have little interest in preserving the building’s architectural history and design and connection to the rest of the neighborhood.

But his forbearance has meant that the house has been unoccupied for the past two years. The paint on the façade’s wooden shingles is peeling; rotten wood lines the building’s exterior. In September, the city’s anti-blight agency, the Livable City Initiative, cited Healy for the dilapidated exterior. In December it issued a $6,100 fine for not following through on required repairs.

“It breaks my heart how I’ve had to postpone work on this house simply because I couldn’t afford it,” Healy said.

He said now he has saved up enough money to truly begin the renovation and restoration process. Working with local architectural designer, historian and entrepreneur Colin Caplan, Healy has pulled an exploratory demolition permit on the site. He said that he and Caplan just have to pull the trigger on which contractor to go with to complete a structural analysis of the building before they can begin to map out and implement the rest of their restoration plans.

Healy said that he could be living in the home in as soon as a few weeks, depending on the results of the structural analysis. He said that the variable that’s more difficult to predict is just how much time and work and money will be required to restore the building to what Caplan described as its “historic glory.”

City land records identify 189 Dwight St. as being built in 1920, but Caplan concluded that the actual construction date is much earlier based on the building’s appearance on an 1859 map of New Haven.

Caplan said his research shows that the house was built in 1853 by George Baldwin Woodruff, a prominent joiner and pattern maker and the London sales representative for the Singer Sewing Machine Company. Caplan said Woodruff eventually sold the house to Oliver F. Winchester, who likely bought it as an investment.

During a recent tour of the building’s exterior and interior, Healy and Caplan pointed out the different structural elements that make 189 Dwight St. unique.

Caplan explained that the house was built in the Carpenter Gothic architectural style, which privileges ornamental, jig-sawn details like the wave-like wooden latticework that top the building’s façade.

He said that vertical board and batten siding likely comprise the building’s exterior, hidden just beneath the peeling wooden shingles which were applied in the 1920s.

“We want to explore whether it’s feasible to take out the 100-year-old shingles and get to the 150-year-old core,” Caplan said. He cited 33 Beers St., a property that he helped restore as a high school student working with Neighborhood Housing Services (NHS) in the mid-1990s, as a successful nearby example of a restored and revived Carpenter Gothic home.

“It was meant to be seen,” Caplan said about the ornamental details, some still visible, some hidden, on the building’s façade. “It was meant to be a showpiece. The faces of these buildings were the representations of their owners.”

Inside the building, he and Healy pointed out the myriad mid-19th century details peeking out beneath the sustained wreckage caused by the water pipe burst and subsequent demolition.

An octagonal bay on the northern edge of the home retained its heart pine hardwood floor and diamond-framed window panes.

Arched windows in the entryway still held a few glass panels that Caplan said were likely from the 1850s, based on the waves, bubbles and imperfections.

“This stairwell is one of the most unique stairwells I’ve ever seen in New Haven,” he said, pointing to a spiral wooden stairwell that spun 180 degrees as it climbed from the first to the second floor. “This would have been quite an elegant stairwell in a working-class neighborhood.”

On the second floor, Healy and Caplan pointed out where the water leak happened, but also the demarcation line in the home’s cruciform layout between the original 19th century building and a later addition.

“Every homeowner could take a lesson from Scott,” Caplan said in regards to Healy’s determination about how much to invest in historical restoration on top of the more immediate costs of making the home safe, stable and habitable. “That’s the passion versus the business sense,” he said.

“People always tell me to accept one of the offers to buy the house,” Healy said. “That the restoration work is a huge undertaking. It is. But I want this to be a house where people walk by and say, ‘Wow, this is what makes my neighborhood special.’”

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posted by: AverageTaxpayer on April 17, 2018  6:01pm

Hero? Or Slumlord?

The road to hell is paved with fine intentions.

How much money has Healy put back into that property over the past almost two decades? Versus how much money he has taken out?

Besides selling to larger concerns, Scott Healy could actually sell his decaying house to a responsible homeowner. One whole would live in the house and actively maintain it…

posted by: Scott Healy on April 17, 2018  6:35pm

I want to thank my neighbors on Dwight Street and beyond for being incredibly patient, understanding and vigilant. Through every cruel twist and turn of the last three years, the Dwight community has helped me in every way possible: giving me advice on how to restore a historic gem; keeping a watch on the building in brutal weather; connecting me with experts who understand the historic context of this home and how best to bring it back to life; and believing in me whenever I’ve doubted what’s possible to get done. After experiencing life outside of New Haven in the last few years, I’ve learned something important: New Haveners are completely unique in how they care for and protect the place they live. No city works harder to make itself stronger and better.

I can’t thank my community enough for instilling in me that same drive to uncover hidden strengths and new opportunities. I’m deeply proud of New Haven and the Dwight neighborhood that immediately embraced me when I became a homeowner in 1999, and I’m grateful that Colin and others have been so generous with their time and energy. Thank you for reminding me what “home” truly means.

posted by: NHVCyclist on April 17, 2018  8:35pm

This is awesome!  Glad to see others are as passionate/nerdy about historic property restoration as I am.
Didn’t realize Colin got involved in this stuff…I may contact him for some insight on a project I’m planning out.

But…really LCI?  Yet again in just a few days of NHI articles…what is the point of this city department?  Why do our too-high property taxes pay for this, not to mention fleecing small-time landlords for “license” fees?  They issues a huge fine for a little-guy homeowner who is in the process of gathering funds and negotiating with his insurance company, while corporate slumlords (we know who) put tenants’ health and safety at risk with no consequence?

posted by: Scott Healy on April 17, 2018  11:05pm

Hey AverageTaxpayer,

I understand your sentiment, but youch—“slumlord” is a tough moniker to read. Would you call me that if you weren’t using a pseudonym instead of your real name?

If you’d like to sit down with me and open my books, I’d be glad to show you what my rental income has looked like in the (almost) nineteen years I’ve occupied 189 Dwight Street. I’ll share with you what life looked like for me when I lived there full time and had two tenants downstairs, and I’ll share with you what life looked like when I decided it wasn’t right to rent any apartments while making noisy, inconvenient repairs to a beautiful historic building.

If you owned a house like this on Dwight Street, I’m sure you’d understand how easy it has become to sell to Pike or Mandy or a half dozen other fly-by-night developers interested in a prime rental property steps away from downtown. But that’s not what I’ve chosen to do. My dream is to (eventually) see a family live in and love my house, just like I did as a first-time homeowner. That means I have to be very careful as a steward of this historic site.

Instead of hurling insults from the safety of an anonymous profile name, I hope you instead reach out to me. I could use all the encouragement and support neighbors like you have to offer.

posted by: robn on April 18, 2018  6:58am


Rule number one is keep the water out. The metal roof (or faux replacement of it) is a distinctive feature of this house so I’d suck it up and redo it because it’s ready for it (don’t forget snow guards). I’d include a shallow sloped metal roof on the porch (which is awesome) because it’s also a defining feature and the flat roof makes the whole house vulnerable to water infiltration. You could go as low as 1/4” per door with standing seam but I’d be more aggressive (like 1/2” to 1” per foot) specifically to shed snow).

posted by: AverageTaxpayer on April 18, 2018  8:12am

A quick review of the New Haven land records shows that his mortgage holder twice began foreclosure proceedings against Healy in 2017.

Neighbors should then wonder where he is going to find the resources to enact his grand restoration plan. What bank is going to lend to him, given his past history of failing to pay his mortgage?

Also, LCI would not have been quick to fine and lien his property. That happened only after many attempts to contact and work with him to bring his blighted property back to life.

The best for everyone, - house, neighborhood, and Healy himself - would be if he found and sold to a new owner occupant. Heck, maybe Colin Caplan could work with the new person, (and their borrowing capability), to enact the substantial plans he is currently developing.

Here’s hoping Healy does the right thing. That house has been a disgrace for many, many years.

posted by: AverageTaxpayer on April 18, 2018  9:15am

@ Scott—Ask any small landlord how they do things successfully. Fact is that if, over the years, you had put any money towards the upkeep of your 3 or 4 family apartment building, it wouldn’t be in such a sorry, derelict state.

But hey, at this point that’s all water under the bridge. No need for finger-pointing or recriminations. Stuff happens in life. You are no better or worse than however many other well-meaning, (yet inept), landlords in New Haven. Frankly your 189 Dwight is now just a practical problem. What is best for you, the house, and your frustrated neighbors?

My question is whether you honestly have the means to set your property right? If not, please, please list it for sale, at a high price, then work a deal to sell it to an owner occupant of your choice,— i.e. someone with the means to do the historic renovation that I do believe you want to see happen.

This saga does not have to drag on, and on.

posted by: Scott Healy on April 18, 2018  9:51am

Hi again, AverageTaxpayer,

As much as I don’t agree with you, your passion and interest in my house is exactly what I love about New Haven. Thank you for your vigilance.

As a dedicated reader of the NH Independent and a big fan of SeeClickFix, I follow comment threads that include a lot of New Haveners, many of whom are my neighbors. And as a management consultant who focuses on how executives and managers communicate, I’ve learned to see distinct patters in syntax, word choice and grammar.

I don’t know why you’re hiding behind a screen name, but I have a good sense of who you are. And it makes me wonder why you don’t just reach out and give me a call or drop me an email. It seems oddly petty and unneighborly to air grievances in this forum.

As for the land records you cite, you’re right: the bank that eventually acquired my small home equity loan—not my mortgage—did, in fact, threaten me with foreclosure, but not for the reason you’ve assumed. Because of an error in the bank’s loan acquisition that impacted a whole lot of borrowers, the threat of foreclosure occurred in error, and the bank has rectified the oversight (my funds were held in escrow during the entire resolution process). It’s disappointing to me that New Haven now has so few lending institutions that are still firmly planted in our community (RIP, New Haven Savings), and sadly, many lenders put algorithms above human wisdom in how they operate. I was on the receiving end of that problem—a problem that might be a good place to channel your energy as a local advocate.

I’ve faced a lot of uphill battles in returning to my house on Dwight Street, including skeptics like you whose motivations are unclear to me. I’ve watched as people who have long wanted to acquire my property at a discount have used the LCI anti-blight process to lodge complaints. I’ve had people tell me to just walk away.

Luckily, my supportive neighbors outnumber the naysayers. I hope I’m able to win over folks like you.

posted by: Scott Healy on April 18, 2018  9:58am


The work has already started. If you’d like to be helpful, you might stop by with some coffee and doughnuts for the crew—that’d be thoughtful.

I’m sorry the house isn’t going on the market anytime soon. I hope that doesn’t thwart your own interests.

It disappoints me that you’re continuing to hide behind a screen name, since you’d be a much more effective advocate if you had the courage to confront fellow community members in a more honest, straightforward way. But I get it: it’s easier to launch barbs anonymously.

I’m sure I’ll see you around the neighborhood. Good luck with the work you’re doing these days.

posted by: AverageTaxpayer on April 18, 2018  10:20am

@ Healy—

So none of this is your fault? The condition of your house, the foreclosure proceedings, and the LCI action?  To hear you tell it, you’re the victim here, and not the blighted historic property, the bank, nor your long-suffering neighbors. (maybe they called LCI because an empty, derelict house affects their property values, insurance rates, and quality of life?)

Anyway, this is not a question of whether you are a good guy or a bad guy, or whether your intentions are sincere. Instead it boils down to the question, “Do you have the financial wherewithal to fix up your property? And will work commence this year?”

If you don’t have the means, the answer is pretty obvious. SELL to an owner-occupant!

posted by: Scott Healy on April 18, 2018  10:21am


One last thing, since you seem to have a narrative in your head that you can’t seem to shake.

When I left to attend graduate school, I hired Connecticut Bi-Glass to restore my windows—a painstaking process that salvages the original window frames but adds a layer of glass to make the windows energy efficient. This was incredibly costly—and most owners would have just replaced the windows. But almost all of my windows were original to the house, and a building’s fenestration is one of the most important contributors to its historic character. Have you taken the same care with your own historic windows? (I know the answer to that, so no need to respond.)

I also combined two units into one because when the local broker sold me my house (do you remember who she is? I think you do), the shoddy work that she had done on the property was not up to code. The units presented an obvious fire hazard, even though she SWORE at the time that all this mishegoss was grandfathered in. Imagine my dilemma: I got bad advice from someone with a vested interest in making a sale, and I was stuck addressing things that the broker should have been more honest about. Hmmm.

And then, when I started to address the soffits, fascia and roof, I realized something interesting: the cedar shakes—which the broker had arranged to sloppily paint to hide some clear problems—were covering over an elegant old building with vertical board and batten siding. The same kind of insensitive shingle treatment had been done to 33 Beers Street, one of the most visually striking homes in our neighborhood. I discovered this by accident, but it made me stop what I was doing and begin saving money to restore this home the right way.

Is paint peeling on my house? Yes, but the paint is on shakes that aren’t original and shouldn’t have been so poorly painted in the first place. Do the soffits need restoration? Yes, and the work has started. Maybe withhold your judgment until you see the results.

posted by: NHVCyclist on April 18, 2018  11:02am

Scott - Don’t be deterred by the negativity.  Also I find it unfortunate that people make assumptions about a person’s character and financial situation based on vague public records.  I’ve learned not to trust those.

The fact that those interested in the property leveraged LCI to try to force the owner’s hand is disgraceful, but even worse that LCI actually fell for it.  The house clearly needs help, but there are much worse looking homes that people actually LIVE in, right in that neighborhood.  Those are the houses that LCI should address - the ones that may be a threat to the occupants’ health and safety.

posted by: Scott Healy on April 18, 2018  11:40am


Again, I don’t understand your motivations here or why you’re airing a grievance that clearly stems from something else. I never said I was the victim—no reader of this article should take away the sense I’m a victim. I just want to be clear on what public records reflect so that people can make up their own minds here. I’m a small property owner who misses his home and has wanted to complete a restoration that, frankly, most developers and landlords wouldn’t touch. Do I have a blind spot when it comes to historic buildings in my neighborhood? Yep. But if more people in the Dwight neighborhood had the same blind spot, we’d have quite a few more healthy, restored blocks.

Through every turn of the last two years, I’ve kept my house safe. I’ve trimmed and mowed and picked up litter and monitored the lot—just like when I lived there from 1999 (remember when I bought it, and you directly benefited from the sale?) until I attended graduate school. And when I see how many of my neighbors are still renting properties that are much more “derelict” than mine, I scratch my head wondering why advocates like you are so selective in your advocacy. Where are the defenders of those historic homes that, just steps away, are in much worse shape than mine? Where’s your passion to get these other folks to sell?

I don’t see it. And it’s becoming more and more obvious why.

No, AverageTaxpayer, I’m not a victim. But I’m also not deterred by people like you. Thanks again for your vigilance in commenting here, no matter your motivation.

posted by: Kevin McCarthy on April 18, 2018  12:04pm

AT, there’s been a long debate in the NHI on the impact of the new developments on housing affordability. But I suspect most of the participants would agree that converting a four-family to a single family, as you suggest in your first comment, would not help.

posted by: Scott Healy on April 18, 2018  12:25pm

@Kevin, what AverageTaxpayer forgets—even thought I’ve reached out directly to share this—is that 189 Dwight should be a 2-family home. Jim Paley, who has done an incredible job creating affordable homeownership opportunities at NHS, has converted quite a few local properties into places where the rental income of a second unit helps defray the costs of a mortgage.

For many years at 189 Dwight, I lived in one of four units, but the one-bedroom apartments were never roomy enough for anyone except Yale students whose time in New Haven was always temporary. I’m working to change that and make this house a place where I can live on one floor (more than enough room for me) and rent out the other. In the long run, this conversion will make 189 Dwight the perfect place for any homeowner occupant, even if I die from the slings and arrows shot at me by people like AverageTaxpayer.

posted by: M Short on April 18, 2018  12:31pm

Congrats Scott! Two feet in or two feet out!

Great choice in Colin who played a key role when at NHS on redesigning the two odd vacant commercial spaces at the corner of Dwight and Edgewood into a nice two family house.

Wishing you luck and will be here to help!

posted by: Sven Martson on April 18, 2018  1:48pm

As Scott’s neighbor (and former landlord) I must confess to making complaints about the condition of his house on the See Click Fix website a year or two ago.  The dilapidated condition of this uniquely beautiful house was a painful sight for many of us on Dwight Street.  My understanding was that Scott had been in foreclosure and had abandoned the house.  I was obviously incorrect in that assumption and I now see that I may have caused Scott some unnecessary trouble.  I’d like to publicly apologize to Scott and express my great pleasure in seeing him commence the restoration of his lovely house.

posted by: AverageTaxpayer on April 18, 2018  1:50pm

@ Kevin — not sure how my suggested option of selling to an owner-occupant gets translated into “conversion to a single family.” The neighborhoods surrounding downtown are full of owner-occupied multi-family houses.

@ Scott — point in fact, you’ve been a not-so-good steward of a fantastic Dwight Street home. Over the years, it’s been painful to watch your property fall into such a state of disrepair.

If you are turning it around, and restoring 189 Dwight to a state of respectability, good luck and god bless. For everyone’s sake, (including yours), I genuinely wish you success.

posted by: Bill Saunders on April 18, 2018  2:06pm

Good Luck with the restoration, Scott—it’s a unique house.

Welcome back to the neighborhood!

posted by: Jonathan Hopkins on April 18, 2018  3:14pm

Good luck on the renovations!

posted by: Scott Healy on April 18, 2018  3:17pm

@Bill, your reassuring comment here means more to me than you could know. I’m pretty sure the first time we met was at 189 Dwight, and Lisa Yates—the architect who introduced me to this house’s unique history—is the person who inspired me to dig deeper instead of doing band-aid repairs.

I read the Independent religiously, and the more time that passes from my time at Town Green, the more I appreciate how you kept people like me accountable and focused on what makes New Haven a great place to live. Shamelessly, it’s people like you who make my neighborhood a place people want to find rentals. But more importantly, it’s people like you who keep the city I love vital. Thank you.

posted by: Kevin McCarthy on April 18, 2018  3:20pm

AT, fair enough - “homeowner” in your first post could be construed as “owner occupant.” But that is apparently what Scott plans to be.

posted by: Bill Saunders on April 18, 2018  4:38pm


I know Little Miss Mess-Up emerged from that apartment many times in her heyday, but I am not sure we officially ‘met’ until Ideat Village! 

Best of Luck with the house…
Looking forward to seeing it progress…

posted by: KenC on April 18, 2018  10:08pm

I think many of the people commenting are not being honest about the problems with this house. There are many stories like this in New Haven because maintaining a house is not easy and I understand the lack of funds—I’ve been there.  However, there is no excuse for a homeowner to allow this much water damage.  The homeowner obviously neglected this property for years—not just 3 or four years.  The house needs a roof right away—it should have a tarp over it right now to prevent more damage.  The porch, the roof facial boards and many of the clapboards also need to be replaced—and that is just the outside.  The problem is that these items are almost irreplaceable.  The roof on my home had to be changed because of water damage—the damage was much less than this one and it was still a very expensive endeavor.

posted by: 1644 on April 19, 2018  7:18pm

AT:  When selling a home, there is no practical way to control what people do with it after the sale, or whether the buyer will be an “owner-occupant.”  Most real estate agent contracts require acceptance of any qualified buyer within a price range.  Buyers often lie about what their intentions are, or, like Mr. Healy, are undercapitalized.