A life , Guided by thoughtful wealth management. well lived
You have built a remarkable life shaped by vision, perseverance, and thoughtful decisions. Your wealth should be guided with that same intention.
Doctors, Moguls, and Renaissance Men
Every issue of Milford City Lifestyle starts the same way: we look around this city and ask who deserves more attention than they're getting. This time, the answer pointed us toward some remarkable gentlemen.
When we built this issue, we were looking for men whose stories had real substance — people who have put down roots in Milford, built something meaningful, and contributed to this commu nity in ways that go beyond a title or a résumé. As it turns out, we had plenty to work with.
You'll meet Dr. Perry Opin, one of the oldest practicing orthodontists in the United States, who has spent decades doing precise, dedicated work caring for patients in this city. His story is a study in what a long career actually looks like, and what it takes to keep showing up for it.
Then there's Sylvester Poli, the theater mogul who stepped away from his business empire and built a stretch of Mediterranean-style homes along Milford's coastline in the Woodmont neighborhood, designed with his family in mind. We spoke with his descendants about what it means to carry that legacy forward and what Poli's vision still says about the place he chose to call home.
And you'll hear from Bill Doolittle, whom we're dubbing Milford's unofficial "Renaissance Man," and whose wide-ranging interests and pursuits make him one of the more genuinely interesting people in this city.
These are just a few of the men featured throughout these pages. Taken together, they paint a picture of Milford that we think is worth sitting with.
Thank you, as always, for reading.
Correction from May 2026 issue: Tyde photography credit: Jessica Iovino
June 2026
PUBLISHER
Mark Arnold | mark.arnold@citylifestyle.com
EDITOR
Chelsea Spata | chelsea.spata@citylifestyle.com
INTERNS
Gavin Conte, Harshitha Kothapalli, Kayla Markowitz, Fiorella Gargiulo, Isabella Mora, Dylan Robinson
CONTRIBUTING WRITERS
Gavin Conte, Harshitha Kothapalli, Kayla Marowitz, Chelsea Spata
CONTRIBUTING PHOTOGRAPHER
Mark Arnold
Corporate Team
CEO Steven Schowengerdt
President Matthew Perry
COO David Stetler
CRO Jamie Pentz
CoS Janeane Thompson
AD DESIGNER Rachel Chrisman
LAYOUT DESIGNER Lillian Gibbs
QUALITY CONTROL SPECIALIST Marina Campbell
The Optimization of Men’s Testosterone
Courtney Holmes, DNP, APRN, “The Alchemista”
Restoring energy, strength, and clarity through evidence-based testosterone care
ARE YOU BEING TOLD YOUR TESTOSTERONE IS “NORMAL”?
• Low energy or constant fatigue
• Loss of strength or muscle mass
• Increased body fat (especially midsection)
• Brain fog or reduced focus
• Low motivation or drive
• Decreased libido or performance
Millions of men are told their testosterone levels are “normal,” even while experiencing symptoms that impact their energy, performance, and quality of life. But “normal” is a wide range. And it’s not the same as optimal. If you don’t feel like yourself, “normal” isn’t enough. Many men fall into a gray zone where levels are technically within range, yet not high enough for how they want to feel and function. At Milford Med Spa, we don’t treat numbers alone, we treat the full picture. When symptoms and labs align, testosterone therapy can help restore energy, rebuild strength, improve focus, and support longterm health. This is personalized, medically guided optimization. Through structured, evidence-based care led by Courtney Holmes, DNP, APRN and a team of experienced nurse practitioners, we help men reclaim their edge with a plan tailored to their body and goals.
“Many men are told everything is ‘normal.’ But when we take a closer look, we often find an opportunity to optimize how they feel.”— Courtney Holmes, DNP, APRN
Founder, Owner, & Medical Director of Milford Med Spa & Wellness
Know your T level. Know your options. Schedule your testosterone evaluation.
99 Cherry Street
Milford, CT 06460
203-701-6161 (text or call)
Photography by Courtney Benanto
Starting at $167/month
Treatment based on symptoms, lab evaluation, and clinical assessment
SPRING AWAKENING BY THE RADIANCE MD
Spring is about fresh starts and your skin deserves one too. After months of coldweather, dryness, and stress, regenerative treatments like microneeding with exosomes help stimulate collagen, repair damage, and restore radiance form with in think of it as a deep clean for your skin cells-not just the surface.
Results you can see and feel. March specials & custom treatment plans available. Book your spring skin reset today.
Jennifer Dilungo, PA-C
Sherif Saleh, MD
Juliana Maria Arbelaez Linero, APRN
Jessica Sarkisian, APRN
Veronica Ahlgrim, NURSE INJECTOR
city scene
WHERE NEIGHBORS CAN SEE AND BE SEEN
1: Matt and Reggie 2: Duck Pond Pals 3: John Callagher, 2nd in command VA CT; Tom Jackson, Chairman, Veteran Committee and Parade Commission 4: Deadgrass at the MAC 5: Friends in the Studio 6: Typical morning 7: Jeannie Maestre, personal trainer and owner, Soul Fit 360
Ultimate Interiors Knows Your Floor
is Your Foundation
Ultimate Interiors has been a family-owned flooring business on River Street in Milford since 1959. The showroom carries a wide range of flooring options — hardwood, carpet, tile, laminate, bamboo, cork, and resilient — along with custom bath and shower installations. Staff assist customers through the full process, from product selection to installation. Free estimates are available, and the business serves communities throughout the Greater New Haven area. Showroom hours run Tuesday through Saturday.
Find Film, Frames, and More at Milford Photo
Located at 22 River Street, Milford Photo carries cameras, lenses, and photography accessories from major brands including Canon, Nikon, Sony, and Fujifilm, along with a selection of pre-owned gear. Beyond equipment, the store offers a wide range of services: film developing, photo printing, video transfers, passport photos, custom framing, scanning and archiving, and camera maintenance. Photography classes are also available through their Learning Center. Hours are Monday through Saturday, 10 a.m. to 5 p.m.
Hand Crafted Custom Furniture
Entire Home
Inner Circle Legal Planning Helps Families Prepare for What’s Next
Inner Circle Legal Planning is a Milfordbased estate planning law firm led by attorney Bryan M. Etter, licensed in Connecticut and New York. The firm handles wills, revocable and irrevocable trusts, probate, and business succession planning. Consultations are structured to walk clients through their options in plain language, and the firm operates on a flat-fee model. Initial consultations are free. The office is located at 151 Broad St.
Milford’s
Orthodontist Since 1968
Our focus is always on you and your smile
Dr. Gary Opin and Dr. Perry Opin understand that changing a person’s smile can change a person’s life. Throughout your entire orthodontic experience, they will be attentive to your comfort, will listen to and respect your treatment goals and concerns, and partner with you to achieve a lifetime of smiles. At Opin Wide Orthodontics, our doctors develop lasting relationships with our patients and their families, while providing a superior level of care to create healthy, engaging smiles. For over 55 years, we have been leveraging state-of-the-art treatments to provide our patients with highly individualized, effective care.
PLAY TO WIN
ARTICLE BY HARSHITHA KOTHAPALLI |
PHOTOGRAPHY BY MARK ARNOLD
VOCALIST, EXECUTIVE, PROJECT MANAGER, GOLFER, NEIGHBOR — BILL DOOLITTLE HAS LIVED MORE LIVES THAN MOST. AND HE'S NOT DONE YET.
If you ask Bill Doolittle where he’s from, he might answer with a question first. A bit of local trivia: he was born in the United States, but not in a state. Washington, DC – a fitting beginning for someone whose life has never followed a predictable path.
His father, a Woodmont native, met his mother at American University after World War II. By the mid-1950s, they had settled in Milford with what would become a bustling household of five children, their parents, and a grandfather under one roof. “A typical, large family of the 50s,” Doolittle recalls. “We made Milford home.”
His two sisters, Peggy and Patty, and two brothers, John and Richard, have led successful lives filled with teaching, serving, growing, and guiding. At the center of it all were his parents –especially his father, an educator who became principal of the Lenox Ave School in Devon and later served on the Milford Board of Education.
Following in his father’s footsteps, Bill taught fifth grade for seven years in Redding before he moved into the private sector helping lead companies like PHH, Kinko’s, Global Experience Specialists, and Bombardier through expansions and turnarounds. At Kinko’s, he built an 800-person commercial sales organization from scratch before it was acquired by FedEx for $2.3 billion. At his final company, he lead the design and fabrication of trade show exhibits for global events including the Vancouver and London Olympics and the Harry Potter World Tour. During his career, he and the family relocated thirteen times.
Despite numerous experiences that took them all over the globe, Bill and his wife, Pam, always considered Milford their foundation. “While we did leave in 1982 and return officially in
2013, Milford has always been home for my family – Katie and Nathan, Jimmy, Alexis, Gabriel and Sebastian,” he says.
Bill describes Pam as the rock of his family and his life. They met at the First Church of Christ, where both families have worshipped for generations. Years later, they were married there. Last year, they celebrated their 50th wedding anniversary.
Beyond business and service, Bill is a man of many talents and interests. He has been a vocalist with The Vocal Majority, a nationally recognized a cappella ensemble that has sung for Presidents and locations around the world, recorded with the Mormon Tabernacle Choir, opened a restored theater for Microsoft co-founder Paul Allen, and produced over 20 albums – now on display in Bill’s third-floor loft. He’s also an avid golfer, a trumpet player, and a man whose office doubles as a museum of a life well-traveled.
Amidst such a storied past, Bill often reflects on what it means to have started out and returned to Milford:
“Folks from Milford reminisce about their growing years, the influence Milford has had on their lives, and how they enjoy coming ‘home,’” he says. “It’s really a special place for that.”
Now, Doolittle remains in motion. He and Pam live on the beach at East Broadway, in a home built on a property her grandfather purchased after the Hurricane of 1938. He continues a more personal fight. “My passion right now is continuing the ‘stomp the monster’ health challenge I have been fighting since 2007,” he says, referring to his long battle with Parkinson’s and Stage III prostate cancer. He works out five days a week, visits Memorial Sloan Kettering regularly, and reaches out to others newly navigating similar diagnoses — offering the kind of encouragement only someone who has walked the road can give.
That commitment shows up in the work he continues to do. As a trustee of the First Church, he served as a project manager on the restoration of its 200-year-old Meeting House steeple — a $500,000 effort completed last summer. He managed it all, including many climbs up the scaffolding to the weathervane. “My fingerprints are still embedded in some of the steelwork,” he says.
To some, it might look like an impressive bucket list. But Bill frames it differently. “I believe it is more of an obligation rather than curiosity,” he says. “For all the city has provided for me and my extended family for so many years.”
Still, what surprises him most is not the breadth of his experiences, but the speed of them. “I’m frequently reminded not to let my 28-year-old brain get in the way of my 75-year-old body,” he jokes.
Bill’s life, layered with decades of movement, service, and memory, reads like a living archive of Milford itself. A “Renaissance Man” for the modern era, Bill is proof that a life fully lived leaves fingerprints everywhere – on steelwork, on stages, and on the people lucky enough to know him.
“A TYPICAL, LARGE FAMILY OF THE 50S...WE MADE MILFORD HOME.”
CUSTOM FENCING SOLUTIONS
THE SMILE MAKER
Dr. Perry Opin’s Six Decades of Orthodontic Excellence in Milford
ARTICLE BY CHELSEA SPATA
PHOTOGRAPHY BY MARK ARNOLD
When I ask Dr. Perry Opin to “start from the beginning,” his eyes widen and he reclines slightly in his chair. He looks at me with an ironic smile as he clasps his hands together in front of him.
“When I was twelve I knew I wanted to be an orthodontist.”
“When I was twelve I knew I wanted to be an orthodontist.”
We are sitting in his office at his Broad Street practice, which he shares with his son, Dr. Gary Opin. On all walls are floor-to-ceiling credentials that read like a career highlight reel: there are framed letters from the federal government, certifications no one else in Connecticut holds, and photographs of a young Dr. Opin surrounded by colleagues who, as he’ll tell you with a mix of pride and wistfulness, are mostly gone now. He gestures toward the photo almost every time a name comes up. “He passed. He passed.” A pause. “There are very few of us alive.”
After 60 years, Dr. Perry Opin is one of the oldest fulltime practicing orthodontists in the United States.
A CALLING, NOT A CAREER
Dr. Opin’s father was an ear, nose, and throat
specialist practicing out of the Bronx. His mother was an attorney who stopped practicing when she married. She had opinions about her son’s future: “She was fighting with me. She said, ‘I want you to be a physician like your father.’” Young Perry held firm: “I said no, I want to be an orthodontist.”
He attended college in three years, earned his degree, and was accepted to NYU Dental School, where he graduated in the top five of a class of 177. From there, a two-year military commitment took him to Fort Benning and thrust him, unexpectedly, into orthodontic practice before he’d even gone to graduate school.
The post’s orthodontists had just completed their service and left, and a colonel needed someone to fill the gap. “He called me into his office, and said, ‘You’re going to do orthodontics.’ I said, ‘I haven’t been to school yet.’ He said, ‘You’re going to be an orthodontist.’” Perry’s answer: “Yes, sir.”
He would go on to train under some of the most distinguished figures in the field, including Robert Strang – the first orthodontist in the state of Connecticut – who wrote several foundational texts and was, in Dr. Opin’s estimation, “very, very smart. Very, very old. Almost as old as I am.”
He had every intention of staying in the military. He loved the life. But when the Army wanted him in Vietnam before he could finish his schooling, he made his choice. “I said, it’s been a pleasure, it’s been my great life. I thank you.” And with that, Dr. Opin was on his way to Connecticut.
FINDING MILFORD
The story of how Dr. Opin landed in Milford is, like most of his stories, circuitous and told with pleasure. He was on the wrong highway and stopped to ask for directions in West Haven. He drove up the Post Road and took one look around at the activity, the Sound, the housing stock, and the families who had settled in town. “It was my kind of people,” he says simply. He called his wife and told her he had found his place. That was 1968.
The practice opened on Broad Street – not in its current building, but close enough that you can see the old one from the new. The current location has been home for more than 26 years, and was recently remodeled after an incident involving a runaway car that came through the waiting room. Fortunately, nobody was hurt, and the new waiting room – which sits inside a turret of the Victorianstyle building – is fresh, welcoming, and replete with natural light.
A PRACTICE BUILT ON PEOPLE
Seventeen thousand patients and counting. That is the number Dr. Opin offers when the topic turns
to the scope of his work. It is a staggering figure – the product of 60 years of treating families, children, and in many cases, second and third generations.
Karen Money, a Milford resident and elementary school teacher who has been coming to the practice for 50 years, stopped in during our interview for a routine appointment. She was in fourth grade when her mother first brought her into the original office across the street. Dr. Opin treated her three children – now 29, 25, and 20 – and she still comes back. “He’s the best,” she says, putting her arm around him. “I’d do anything for him.”
His staff reflects the same loyalty. Four of his seven full-time chairside employees have been with him for over 20 years. One has been there, by her own account, seven years in, seven off, and seven back. One of his staff makes him lunch every day. “She is amazing,” he says, with the sincerity of a man who means it. “Don’t tell her – she hates it when I tell her.”
THE STANDARD-BEARER
Dr. Opin has been awarded the American Association of Orthodontics highest honor, The Brophy Award. He has also received the College of Diplomates of the American Board of Orthodontics Foundation Award, a recognition given out only eight times in the organization’s 35-year history. And he was awarded the American Board of Orthodontics Shepard Award, one of their highest honors.
He holds a certification in craniofacial orthodontics, a credential he earned at the Cooper Clinic in Lancaster, Pennsylvania – the first craniofacial treatment clinic in the United States, founded in 1937. For years, he provided much of the orthodontic work for Yale’s Craniofacial Team, the only practitioner in the region with a formal degree in the specialty. A framed letter from the federal government hangs on the wall of his office; it dates to 1969 and represents his formal recognition in the field.
“I am humbled by the recognition given to me by my colleagues,” he says. “But I still have feet of clay.”
THE INNOVATOR
Ask Dr. Opin about technology and he lights up differently – not with nostalgia but with the forward-leaning energy of someone who is still, genuinely, excited about what’s next.
For decades, he has practiced using self-ligating braces – a system in which a small clip, rather than a tie, holds the wire in place. “You open the clip, put the wire in, close the clip, you’re done,” he explains, holding up a model so small you have to lean in to see it. The design is cleaner, faster, and allows for the colored bands that his younger patients love.
More recently, the practice adopted custom bracket formation – a three-dimensional approach in which the face of each bracket is designed to fit the specific surface of each individual patient’s tooth. The process begins with a digital scan of the patient’s mouth, which is sent to a laboratory; the lab returns a proposed bracket placement via digital rendering; Dr. Gary Opin reviews and adjusts those positions, and the finished product arrives in a custom tray that fits precisely over the teeth. “It’s much more accurate,” he says. “And sometimes it’s scary how fast it goes.” Cases that might ordinarily take 24 to 30 months can, in the right circumstances, finish significantly earlier.
LOOKING BACK, LOOKING FORWARD
When asked why he continues – why, after six decades, he hasn’t handed the practice off to Gary entirely and gone to restore more antique cars (one of his many hobbies outside the office) – Dr. Opin’s answer is the same one he has always given. “My son is the reason I’ve been able to work in orthodontics as long as I have. We share diagnostic and treatment plans for every patient. Patients love him and his soft demeanor. He is the perfect son.”
About the work itself, Dr. Opin is clear about its draw: “I love what I do for two major reasons.” He counts them off. “One, you get to meet people you would have never met. Two, when you get done, everybody loves you. And you didn’t cut them. They didn’t bleed. There’s no hurt involved.”
He pauses, looks around at the operatory, at the models on the shelves, at the photograph of Robert Strang and his young orthodontic classmates of who were, for a moment, all alive at once.
“I am glad to say I love it,” he says. “I’ve truly been so lucky.”
DR. PERRY OPIN
Dr. Perry Opin practices orthodontics alongside his son, Dr. Gary Opin, at their office, Opin Wide! Orthodontics, located at 266 S Broad Street. He has been serving the Milford community since 1968.
A man’s lasting imprint isn’t what he earns—it’s what he leaves behind for the people who rely on him. As a husband, a father, a protector, your Estate Plan should reflect that responsibility. At Inner Circle Legal Planning, we roll up our sleeves with you, to safeguard your family, preserve your assets, and ensure your wishes are honored. Protect what and who matters most. Lead your family with strength—today and for generations to come.
Reclaiming Vitality From the Inside
A Q&A WITH DR. SHERIF SALEH OF THE RADIANCE MD
ARTICLE BY KAYLA MARKOWITZ
PHOTOGRAPHY BY MARK ARNOLD
“YOU CAN'T UNDERSTAND SOMEONE'S HORMONAL HEALTH, THEIR ORTHOPEDIC PAIN, OR THEIR METABOLIC STRUGGLES
IN
A 15-MINUTE, INSURANCEMANDATED WINDOW.”
WHAT ARE SOME OF YOUR MOST POPULAR SERVICES RIGHT NOW, AND WHY DO YOU THINK THEY RESONATE WITH PATIENTS?
Right now, it’s all about Metabolic Synergy. Our medical weight loss programs — utilizing next-generation peptides like Retatrutide and Tirzepatide — are incredibly popular because we don’t just prescribe and pray. We pair them with Bioidentical Hormone Replacement (BHRT) to ensure that as patients lose fat, they are gaining bone density and muscle mass. People in Milford and Orange are savvy; they don’t want a quick fix that leaves them looking depleted. They want the radiance that comes from genuine metabolic health. Our patients aren’t just losing weight — they are reclaiming their 30s, 40s, and 50s.
WHAT SPECIFICALLY FELT MISSING FROM THE TRADITIONAL MODEL OF HEALTHCARE THAT INSPIRED YOU TO PURSUE A MORE PERSONALIZED, PATIENT-CENTERED APPROACH THROUGH THE RADIANCE MD?
The 15-minute appointment. That was the broken part for me. You can’t understand someone’s hormonal health, their orthopedic pain, or their metabolic struggles in a 15-minute, insurance-mandated window. I founded RadianceMD to provide slow medicine in a fast-paced world. We deep-dive into blood work, lifestyle, and cellular health. We aren’t just looking for normal ranges — we are looking for optimal ones. Traditional healthcare is a monologue; The Radiance MD is a dialogue.
WHAT INITIALLY DREW YOU TO PURSUE A CAREER IN MEDICINE, AND HOW DID THAT PATH EVENTUALLY LEAD YOU TO AESTHETIC AND WELLNESS CARE?
I went into medicine to save lives — the classic ER and hospitalist dream. But I realized early on that there is a massive difference between not being sick and being vital. In traditional medicine, we wait for things to break. My transition to wellness and aesthetics was born out of a desire to be proactive. Aesthetics isn’t about vanity; it’s about the psychology of confidence. When you look in the mirror and see a version
THE RADIANCE MD
The Radiance MD is a physician-led medical aesthetics and wellness center located in Orange, CT. The practice goes beyond a traditional med spa, offering a comprehensive range of services that address both appearance and overall health. Treatments span injectables, laser and skin care, body contouring, and facial procedures, alongside medical wellness services including bioidentical hormone replacement therapy, medical weight loss, and primary care concierge medicine. The team takes a personalized, whole-body approach — treating patients from the inside out. The office is open Monday through Saturday at 291 South Lambert Road in Orange.
of yourself that matches how energetic you feel on the inside, that’s where the magic happens. I moved into this space because I wanted to treat the person, not the pathology.
ARE THERE ANY NEW SERVICES OR INNOVATIONS
YOU’RE EXCITED TO BRING TO THE RADIANCE MD?
I am particularly excited about our Orthopedic Regenerative suite. We are moving beyond simple PRP, now combining HighConcentrate Platelet-Rich Plasma with specific healing peptides like BPC-157 and TB-500 to treat joint and soft tissue injuries. It’s essentially bio-hacking the healing process. Whether it’s a golfer at Great River with a stubborn elbow or someone who just wants to stay active with their grandkids, we are able to offer cellular-level repair that previously required surgery. It’s the future of longevity — keeping the machine running smoothly without downtime.
WHAT MAKES THE RADIANCE MD DIFFERENT FROM OTHER MED SPAS OR CLINICS?
It’s the intersection of a high-tech lab and a luxury sanctuary, right here in Orange. Most places treat wellness as a side hustle to Botox. For us, the wellness — the peptides, the BHRT, the regenerative medicine, the actual medicine — is the foundation. We are a physician-led center where every protocol is bespoke. We aren’t a franchise; we are partners and advocates for our patients and community. When you come here, you’re getting a partner in your aging process. We don’t just change how you look; we change your biological trajectory.
THE LIONS of Woodmont
SYLVESTER POLI AND THE LIVING LEGACY OF VILLA ROSA
ARTICLE BY GAVIN CONTE PHOTOGRAPHY BY MARK ARNOLD
The iron gates standing at the edge of Woodmont’s shoreline are not just a property boundary; they mark the threshold to an era when the Connecticut coast was the primary vacation location for entertainment royalty.
The story of Villa Rosa and the surrounding homes began with wax. Sylvester Poli arrived in America not as a businessman but as an artist.
“He came to America as a wax sculptor,” explains a descendant of Poli. “His name was Zepherino, middle name Sylvester–S.Z. Poli. When you came to America, you had to have an American name, so he picked Sylvester because he was born on St. Sylvester’s Day.”
The wax museums were the primary source of visual news for the public, often displaying notorious convicts and other notable figures. In fact, Poli’s wife and daughters would often assist in the craft, with family stories recalling how they would hand-inset individual hair follicles to ensure total authenticity. To draw crowds into these museums, Poli began placing song-and-dance acts on the street to grab attention.
“That eventually turned into vaudeville,” explains Charlie Nolan, a great-grandson of Poli, and a resident who owns one of the cottages next to Villa Rosa with his siblings. “He was one of the originators of vaudeville because of that work.”
Indeed, Poli was one of the true originators of the genre, eventually building a massive circuit of ornate theaters that stretched from Philadelphia, Pennsylvania, to Worcester, Massachusetts. At his peak, he owned nearly 40 theaters, including three in New Haven and two in Bridgeport. For those seeking to understand the “Poli Flair,” as Charlie describes it, one need only look at the Waterbury Palace Theater, a perfect representation of his style.
“Once you see the Waterbury Palace, you’ll see the intricate workings, the carvings, the marble,” he says. The theaters were nationally renowned palaces of marble and intricate details, using Italian artisans to create architecture that brought European influence to the American public.
“The estate was reminiscent of the mansions described in F. Scott Fitzgerald’s The Great Gatsby, and was a model for the opulence of the 1920s.”
However, life shifted dramatically for Poli in the 1920s when his son and intended heir, Edward, died of appendicitis.
This tragedy prompted Poli to sell his massive business to Loew’s Theaters. After the sale, he hunted for property along the Connecticut coast from Greenwich to New Haven until he found a specific point in Milford where he could build a family compound for his children and grandchildren. Poli’s vision for this compound was a Mediterranean-style sanctuary where his family could reside together.
To cultivate the space, he created a massive seawall as the foundation for what would become a private family community. Due to his immense wealth, he was one of the few individuals across the country who could afford the highest level of craftsmanship. In fact, he employed the same Italian stonemasons and artisans who were building the Gothic structures at Yale University, bringing Ivy League-level designs to the Milford shoreline.
The estate was reminiscent of the mansions described in F. Scott Fitzgerald’s The Great Gatsby, and was a model for the opulence of the 1920s. The main residence featured a boathouse for two boats that led directly into a private screening room. This room was a bridge between the era of Vaudeville and the birth of modern cinema, featuring projectors, lighting systems, and seating.
Long before home theaters, Poli held pre-screenings of movies in the basement. Family stories recall limousines lined up around the circular drive with movie stars waiting for premieres at the house.
“We have pictures of all the limousines lined up,” a descendant recalls. “And they’re really famous people…standing in line for the opening in the basement of that house.”
A massive patio on the side of the structure features columns that extend 40 feet toward the water and is
equipped with men’s and women’s changing rooms for guests. Guarding the structure are two massive lion sculptures, crafted by Edward Clark Potter – the same sculptor who designed the Patience and Fortitude lions outside the New York Public Library.
The estate became a social hub for the elite, hosting galas, parties, and events. Charlie explicitly recalled a family story surrounding a famous wedding in the 1930s of his Aunt Lily to an Italian Marchese. To celebrate the wedding, Aunt Lily was sent off in a seaplane that landed right on the water to take the newlyweds away to Newport, Rhode Island.
Today, the Poli heritage lives on through the fourth and fifth generations. While many original family homes were sold over the decades, the commitment to the land remains an important aspect for the extended family. 10 Villa Rosa Terrace is still owned by Charlie and his siblings – Laureen, Thomas Jr., Cathy, and Susie. They are all great grandchildren of Sylvester Poli.
“I’m fortunate enough to be the primary steward of my family home,” says Charlie. “I’m the guy cutting the hedges, raking the beach, and hosing the porch down… so when everybody comes in, they feel welcome.”
However, there is also a profound commitment to the family name. Many of the male descendants carry “Poli” as a middle name, a tradition intended to ensure that while last names like Nolan may take prominence, the family name remains on their birth certificates.
Even in death, the family remains close. At the St. Lawrence Cemetery in New Haven, the largest mausoleum serves as the final resting place for several generations of the family. It features an altar and eight burial spots, a place for the grandchildren to see their name carved in stone and memorialized for centuries.
Life at Villa Rosa is defined by deep traditions that have survived the changing landscape of Milford. The estate has weathered the storms of the Atlantic, with the family recalling the devastation of Hurricane Irene
and, more recently, Hurricane Sandy. These storms completely leveled the historic seawalls, but each time, the family has rebuilt.
The biggest event of the year for the family is the Fourth of July, when the whole place is “lit up,” and cousins from all over fight for parking spots to celebrate with the next generations and share in their family’s history. Every year, the family harvests steamer clams from the sandbars during the weekend.
“We all grew up with that tradition,” recalls Charlie.
The proximity of the property to what is currently Anchor Social reminds the family of the original Woodmont trolley station that previously stood in its place. The station was converted by Poli into a restaurant for his grandson and Charlie’s father, Thomas Poli Nolan, and was known for years as Tom’s Villa Rosa.
The future of the estate rests on the shoulders of the younger generations. The family is currently working to archive their history, acknowledging that the story is a “puzzle” with pieces and anecdotes scattered among various relatives. From the original wax molds stored in Charlie’s attic to the grainy photos of seaplanes on the Sound, the effort to archive their family story is about connecting fragments into a cohesive narrative. In fact, Charlie recalls that many
“We’re all engaged to keep it as a family home for generations to come for the historical legacy,”
of his siblings, cousins, and other descendants have cherished historical memories through photographs as well.
“We’re all engaged to keep it as a family home for generations to come for the historical legacy,” says Charlie.
There is a collective sentiment to ensure the legacy does not go to the wayside. Despite the grand and opulent history of the property, the descendants of Poli stay grounded, seeing themselves as lucky and fortunate to have this legacy to carry on.
As the fifth generation continues to fish off the same seawall their great-great-grandfather built, the rich history embedded in the Poli family remains unbroken by the passage of just over a century. The hope is that the city of Milford always remembers the man behind the gates.
ROSA POLI
Rosa Poli was born in Genoa, Italy, and came to America at age 10. She married Sylvester Poli at 16 and worked alongside him from the very beginning — helping build the wax museum displays that would eventually grow into a 30-theater empire across the Northeast. Beyond her role in the business, Rosa was a devoted philanthropist, raising funds for veterans and the disabled, efforts that earned her the Italian Cross of Honor from Queen Elena of Italy. She died in 1960.
The Prete Family has been flooring New Haven county since 1959. As the second generation owner of Ultimate Interiors, Buddy carries on the tradition of hands-on, high-quality workmanship that will last a lifetime. www.ultint.com
Christina Prete and Buddy also took a lifelong passion for charitable work and created an app that helps nonprofits accomplish their mission To honor the Rackiewicz and Prete family’s commitment to giving, the Shopping Away mobile application provides a convenient way to connect those who ask, “How can I help?” with those who say, “Here’s what we need.” Go to shoppinganyway.com to download the FREE App and Support a Cause
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o n f i d e n t l y d o n e ,
f r o m s t a r t t o f i n i s h .
AN EXCERPT FROM EPISODE 6 OF SHARE THE LIFESTYLE, A CITY LIFESTYLE PODCAST
Photographer: Brittany Dawn Short
Creative Director: Jen Birn
Stylist: Stephanie Coultress O’Neill
Location: Hotel Saint Cecilia, Austin, TX
MIKE JOHNSON HAS BUILT HIS LIFE AROUND ONE QUIETLY RADICAL IDEA: THE STANDARD YOU SET PRIVATELY IS THE ONLY ONE THAT MATTERS.
After eight years in the Air Force, a celebrated run on national television, and a health crisis abroad that sent him deep into supply chains and ingredient certifications most founders never touch, the result is Oshun — a luxury ritual brand built on provenance you can trace and integrity you can verify. In an exclusive conversation for the Share the Lifestyle podcast, Mike shares what it actually takes to build something worth putting your name on. Read the highlights below, then scan the QR code for the full episode.
Q: YOU BECAME A FAN FAVORITE ON THE BACHELORETTE AND THEN LEFT THE SPOTLIGHT. YOU MOVED TO MEXICO, LEARNED SPANISH, THEN COSTA RICA, AND BUILT A COMPANY. WHAT DID THAT EXPERIENCE TEACH YOU ABOUT HUMAN BEHAVIOR?
A: “If you’re a good person going in, that shows. If you’re not, that shows too. I also learned that people form this parasocial relationship with you — they assume things about you. When all actuality, different circumstances bring out different parts of who you are. I was on TV trying to find love. The kindness people were showing after felt a bit fake, because they wanted to be a part of something that isn’t who I am individually, but a part of what they saw on TV. And so I had to get away from everybody and everything and the noise.”
THE QUIET STANDARD:
MIKE JOHNSON
“Too many people have prayed for me. So I’ve got to get up and do the walking.”
— Mike Johnson
Q: YOU JOINED THE AIR FORCE RIGHT OUT OF COMMUNITY COLLEGE. WHAT WERE YOU ACTUALLY RUNNING TOWARD?
A: “There was something in me that was saying: I’m not living up to my full potential. I was being a follower. My uncle said, ‘What’s going to make you become an adult the fastest?’ I said, obviously, the military. The Air Force broadened my thought process more than anything. We’re so caught up in our own perception — when you learn to understand different people’s perspectives, it adds to you in so many ways.”
Q: WITH OSHUN, YOU OWN YOUR MANUFACTURING, YOU EMPLOY A CHEMIST, EVERY PRODUCT HAS A BATCH NUMBER TRACEABLE TO ITS ORIGIN DATE. WHY DID YOU DECIDE TO GO THAT DEEP WITH THE BRAND?
A: “The EU bans 1,100 ingredients in personal care products. The U.S. bans nine. That’s my starting point. Oftentimes, it might be the same ingredient, but it comes from a place where it doesn’t have the highest purity. And 60% of what we put on our skin is absorbed. Every product Oshun makes carries a batch number that goes back to the exact day it was created — I can show you every single supplier, the date, the origin. I own more than one part of the supply chain because that’s the only way I can stand behind what’s in the bottle.”
This conversation is just the beginning. Mike goes deeper into why he’s buying land up north, the family in the Philippines who prayed over his factory floor, and what he’d tell every person ready to stop performing and start building. Scan the QR code for the full, exclusive City Lifestyle interview on the Share the Lifestyle podcast.
MIKE JOHNSON
GIVE YOUR MAN HIS SPACE
A Look at The Man Cave
ARTICLE BY EMILY FOSTER INTERIORS
Ok ladies, for those of you that live with your man and are not too keen on his collection of deer heads or affinity for all things Chicago Blackhawks, then let me help you create his very own man cave, that you and he can be proud of.
COMFORTABLE SEATING
With how a man cave is usually done in mind, there are plenty of ways to make this hideaway both agreeable and full of style. I always start with what is most important to your man and 9 out of 10 times it is comfortable seating. So, with that in mind, I start with smart seating. Do we need a sectional? Can we get away with a cool reclining chair? Do we need Barstools? Comfortable, durable, and stylish seating is my jumping-off point.
CONTINUED >
THE RIGHT TELEVISION
Next, of course, there will need to be a TV for gaming and/or sports watching. Try and get him the size he wants, if it can work in space and not be too obnoxious (ladies, you’ll thank me later) because this is all men truly care about. He gets his big TV, then you have more of an opportunity to get what you want in the rest of the house. It’s a win-win.
EXPRESSIVE DECOR
Lastly, without getting too “theme-y,” I organize what he loves and treasures into a gallery wall. I recently did one wall of really cool wallpaper for a husband that was a huge Star Wars fan. It was a black and white Star Wars print that gave this aficionado a fun way to bring his subject matter and style together.
No matter who you are or what you like, I believe every person needs a space where he or she can relax, breathe and be joyful in. Man Caves are no exception.
Tax | Individual | Business
As we proudly celebrate our 25th year in Milford, we are honored to continue serving the individuals and businesses that define and elevate our community. In today’s increasingly intricate tax landscape, even seemingly straightforward returns demand careful attention. Constantly evolving regulations create opportunities—but also the risk of overlooking valuable deductions and credits. While software offers efficiency, it cannot replicate the discernment, strategy, and peace of mind provided by Robert Testo III and his experienced team at RJ Testo and Associates —trusted advisors committed to guiding you with precision, confidence, and care.
realty report
A SAMPLE OF RECENTLY SOLD PROPERTIES IN MILFORD.
Top residential transactions through 4/24/2026
Photo
events
A SELECTION OF UPCOMING LOCAL EVENTS
EVERY FRIDAY, JUNE THROUGH JULY
Fridays After Five
Fowler Field | 5:00 PM
Milford's beloved summer concert series returns to the waterfront pavilion at Fowler Field for another season of free, live music by the Sound. Running Friday evenings from late May through early July, the lineup rotates weekly through a range of acts and genres. Free and open to the public.
JUNE 6TH
Downtown Milford Farmers Market — Opening Day
Wasson Field | 8:30 AM
Milford's beloved weekly farmers market kicks off its 2026 season at Wasson Field. Featuring local produce, artisan goods, and community vendors, the market runs every Saturday morning through the season. Whether you're stocking up for the week or just looking for a reason to get outside, Opening Day is a Milford summer staple worth circling on your calendar.
JUNE 7TH
24th Annual Pirates Day
Downtown Milford | 9:00 AM
One of Milford's most spirited annual traditions, Pirates Day takes over downtown for a full day of swashbuckling fun. The day begins with Pancakes with the Pirates at Lisman Landing, followed by the arrival of Captain Kidd himself by boat in Milford Harbor. Expect a treasure hunt, kids' activities, live music, food trucks, and pop-up vendors throughout the day.
JUNE 13TH
11th Annual Charles Island SUP Cup
Walnut Beach | 9:00 AM
Now in its eleventh year, the Charles Island SUP Cup brings stand-up paddleboarders of all skill levels to Milford's Walnut Beach for a friendly race around the iconic Charles Island. The event draws competitors and spectators alike and doubles as a celebration of Milford's coastal identity. Pre-race yoga with Bend Yoga & Wellness is also available the same morning.
JUNE 15TH
Milford Concert Band — Season Opener
Gulf Beach | 7:00 PM
The Milford Concert Band opens its outdoor summer concert season at Gulf Beach, one of the city's most scenic venues. A longtime community tradition, these free performances draw families and music lovers from across the area for an evening of live band music by the water. Bring a blanket, bring a friend, and settle in for the season's first note.
JUNE 28TH
Milford Moves 5K
Downtown Milford | 8:00 AM
Now in its annual tradition, the Milford Moves 5K — presented by The Milford Bank — brings the community together to honor local veterans with a morning run through the city. The race is open to all ages and skill levels, with a free Kids Run for those 10 and under and complimentary registration for U.S. military members and veterans.
