Top 10 Best Places to Live in Connecticut 2026 for Families, Retirees & Young Professionals

Rank	Town	Median Price (Feb 2026)	Top School Rating (Niche)	Avg Commute to NYC	Best For
1	West Hartford	$485,000	A+	2 hrs 10 min	Families & Retirees
2	Glastonbury	$520,000	A+	2 hrs 25 min	Families
3	Westport	$1,050,000	A+	1 hr 15 min	Families
4	Stamford	$675,000	A	55 min	Young Professionals
5	Greenwich	$1,425,000	A+	45 min	Families & Retirees
6	Litchfield	$522,000	A	2 hrs 30 min	Families & Retirees
7	Danbury	$425,000	A-	1 hr 30 min	Young Professionals
8	Farmington	$460,000	A+	2 hrs 15 min	Retirees
9	Kent	$685,000	A	2 hrs 10 min	Young Professionals & Retirees
10	New Milford	$445,000	A-	1 hr 45 min	Families & Young Professionals

Section V: Deep Dive – Best Places for Retirees in Connecticut 2026

Here are the five towns that stand out most for retirees in 2026. These rankings focus on low maintenance living, healthcare access, walkability, low taxes, cultural amenities, and that hard-to-find sense of community and peace.

1. West Hartford

AARP’s #1 most livable town in Connecticut for retirees

West Hartford tops almost every senior-friendly list in 2026 for good reason. It offers a perfect mix of walkable downtown life, excellent healthcare, and strong community programs designed for older adults.

Key 2026 Stats

• Median home price: $485,000
• AARP Livability Score: Highest in CT
• Average commute to Hartford: 15 minutes
• Mill rate: 32.85

Pros

• Highly walkable Blue Back Square with shops, restaurants, and senior events
• Top-rated healthcare (close to Hartford Hospital and UConn Medical)
• Excellent senior centers, lifelong learning programs, and transportation services
• Safe, tree-lined neighborhoods with single-level homes readily available

Cons

• Higher property taxes than rural Litchfield towns
• More suburban density than true countryside living

Steve’s Note I’ve helped many clients downsize here from larger Fairfield County homes. They love the ability to walk to dinner, attend lectures at the library, and still feel part of a vibrant community without the isolation that can come with very rural areas.

2. Farmington

Peaceful, cultured, and built for aging in place

Farmington consistently ranks in AARP’s top 10 livable towns in Connecticut. It’s quiet, historic, and has outstanding medical access.

Key 2026 Stats

• Median home price: $460,000
• AARP Livability Ranking: Top 10 in CT
• Average commute to Hartford: 20 minutes
• Mill rate: 29.50 (very reasonable)

Pros

• World-class healthcare (UConn Health and John Dempsey Hospital right in town)
• Beautiful historic district with flat, walkable streets
• Excellent senior housing options and active adult communities
• Strong library system and cultural events

Cons

• Limited nightlife or entertainment compared to larger towns
• Some neighborhoods have older homes that may need updates

Steve’s Note This is the town I recommend most often to clients who want a true New England village feel with modern healthcare close by. Many of my retiring clients say it feels like stepping back in time — in the best possible way.

3. Washington & Kent Area (Litchfield Hills)

The low-tax, high-peace Berkshire escape

For retirees who want space, privacy, and stunning natural beauty without being completely isolated, the Washington–Kent corridor is hard to beat.

Key 2026 Stats

• Median home price: $795,000 (Washington) / $685,000 (Kent)
• Mill rate: 10.85 (Washington — one of the lowest in the entire state)
• Average commute to NYC: 2 hours 10 minutes
• AARP-friendly cultural scene

Pros

• Extremely low property taxes
• World-class cultural offerings (Mayflower Inn, music venues, galleries)
• Beautiful walking trails and preserved land
• Quiet, private estates with room for hobbies or gardening

Cons

• Fewer daily services than West Hartford or Farmington
• Hilly terrain can be challenging in winter

Steve’s Note Having lived in Litchfield County for 13 years, I can tell you this area is a retiree’s dream if you want beauty and tranquility. Many of my clients from New York and Fairfield County tell me the peace here is worth every penny.

4. Essex / Old Saybrook

Classic shoreline retirement with small-town charm

These neighboring shoreline towns offer the best of Connecticut’s coast for retirees who still want water views and a gentle pace.

Key 2026 Stats

• Median home price: $520,000–$650,000
• AARP mentions: Frequent top shoreline retiree picks
• Average commute to Hartford: 45 minutes | to NYC: 2 hours

Pros

• Beautiful Connecticut River and Long Island Sound access
• Walkable historic districts with excellent dining
• Active senior communities and boating culture
• Milder winters than inland towns

Cons

• Higher flood insurance costs in some areas
• Seasonal tourism can make summer busier

Steve’s Note Clients who want that classic New England coastal retirement lifestyle love Essex and Old Saybrook. The sunsets over the river never get old.

5. Litchfield Proper

Historic charm with walkable village life and low density

Litchfield offers retirees the iconic New England green, historic homes, and a slower pace at a more reasonable price than the shoreline.

Key 2026 Stats

• Median home price: $522,000
• Mill rate: 23.94
• Walk Score in village center: Very high

Pros

• Stunning historic district with year-round events
• Excellent small library and cultural programs
• Low density with easy access to nature
• Strong sense of history and community

Cons

• Fewer medical specialists than Farmington or West Hartford
• Limited public transportation

Steve’s Note This is my backyard, and I see more and more retirees choosing Litchfield because they get the beauty and charm of a classic New England town without the high costs or crowds of the shoreline.

Thinking of retiring to any of these towns? I’ll show you them personally — from a quiet morning walk on the Litchfield Green to touring active adult communities in West Hartford. Text or call me direct at 860-880-0597. I still answer my own phone.

Section VI: Deep Dive – Best Places for Young Professionals in Connecticut 2026

Here are the five towns that stand out most for young professionals in 2026. These rankings focus on job access, affordability, nightlife and culture, walkability, and future growth potential — the things that matter when you’re building a career and a life.

1. Stamford

The top choice for ambitious young professionals who want NYC energy without NYC prices

Stamford has exploded as a magnet for young professionals, with major corporations, a revitalized downtown, and the fastest train to Manhattan.

Key 2026 Stats

• Median home price: $675,000
• Average commute to NYC: 55 minutes (direct Metro-North)
• Walk Score in downtown: 85+
• Strong tech, finance, and healthcare job market

Pros

• Excellent job opportunities with companies like UBS, Deloitte, and ESPN
• Vibrant nightlife, restaurants, and the new Harbor Point development
• Young, diverse population with plenty of apartments and condos
• Direct train access makes weekend trips to the city easy

Cons

• Higher cost of living than more rural options
• Can feel corporate and busy during rush hours

Steve’s Note I’ve helped many young professionals move here from New York and Boston. They love that they can have a real career and still afford a nice condo or townhouse while keeping the city just an hour away.

2. Danbury

Best value for young professionals who want affordability + growth

Danbury offers the strongest combination of reasonable prices and job growth in western Connecticut right now.

Key 2026 Stats

• Median home price: $425,000
• Average commute to NYC: 1 hour 30 minutes
• Growing tech, healthcare, and manufacturing sectors

Pros

• Most affordable on this young-professional list
• Booming job market with new corporate campuses
• Vibrant downtown with breweries, restaurants, and events
• Easy access to both New York and Hartford

Cons

• Schools are good but not elite
• Some areas still feel more suburban than urban

Steve’s Note This is the town I recommend most often to young professionals who want to buy their first home and actually build equity fast. The value here in 2026 is outstanding.

3. Norwalk

Vibrant arts and culture scene with easy NYC access

Norwalk’s SoNo (South Norwalk) district has become one of the hottest young professional neighborhoods in the state.

Key 2026 Stats

• Median home price: $620,000
• Average commute to NYC: 1 hour 5 minutes
• Walk Score in SoNo: Very high

Pros

• Thriving arts scene, galleries, and live music venues
• Excellent restaurants and waterfront dining
• Growing tech and media jobs
• Direct train to Grand Central

Cons

• Traffic on I-95 can be heavy
• Higher prices near the water

Steve’s Note Clients in their 20s and 30s love the energy here. It feels like a real city neighborhood without the overwhelming size of New York or Boston.

4. New Haven

Culture, energy, and the Yale factor

New Haven offers a younger, more creative vibe than most Connecticut towns, thanks to Yale University and a strong arts/medical job market.

Key 2026 Stats

• Median home price: $380,000
• Average commute to NYC: 2 hours
• Extremely vibrant cultural and food scene

Pros

• Lowest median price on this list
• World-class arts, music, theater, and food scene
• Strong job market in healthcare, biotech, and education
• Young, diverse, and energetic population

Cons

• Some neighborhoods still have safety concerns
• Longer commute to NYC than Stamford or Norwalk

Steve’s Note If you want that big-city creative energy at a price that actually makes sense, New Haven is hard to beat in 2026.

5. Torrington / Winsted (Litchfield County)

Best affordable “hidden gem” for young professionals who want space and value

My backyard in Litchfield County offers the best bang-for-the-buck lifestyle for young professionals who want to own a home and still have money left over.

Key 2026 Stats

• Median home price: $355,000–$420,000
• Average commute to Hartford: 45 minutes | to NYC: 2 hours 15 minutes
• Revitalizing downtowns with new restaurants and breweries

Pros

• Lowest prices on this entire list
• Easy access to hiking, lakes, and outdoor activities
• Growing job market + remote-work friendly
• Strong rental demand if you want to buy and house-hack

Cons

• Fewer high-paying corporate jobs than Stamford
• Nightlife is quieter than bigger cities

Steve’s Note I live and work right here. Many young professionals I’ve helped in the last year tell me they get more house, more land, and a better quality of life for half the price they’d pay in Fairfield County. This is the smart move in 2026.

Thinking of moving as a young professional? I’ll show you these towns personally — from a downtown condo tour in Stamford to a Sunday drive through Torrington’s revitalizing neighborhoods. Text or call me direct at 860-880-0597. I still answer my own phone.

Section VII: Town Comparison Quick-Reference Table

Here is a clean, side-by-side comparison of the Top 10 towns for 2026. All data is current as of February 17, 2026 (Redfin, Zillow, Niche, and CT OPM mill rates).

This table makes it easy for readers to compare at a glance and quickly see which towns match their budget and lifestyle.

Thinking of moving to any of these towns? I’ll show you them personally — from a quick drive through West Hartford to touring affordable homes and larger lots in Thomaston or Litchfield. Text or call me direct at 860-880-0597. I still answer my own phone.

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Section VIII: Your Next Move with Steve Schappert

You’ve now read the most up-to-date, data-driven ranking of the best places to live in Connecticut for 2026.

Whether you’re a family looking for top schools and safe neighborhoods, a retiree seeking walkability and low maintenance, or a young professional wanting affordability with real career options — Connecticut has a town that fits your life perfectly right now.

Here’s your simple, no-fluff 2026 Moving Checklist so you can take action today:

Quick-Start 2026 Moving Checklist

• Decide your #1 priority (schools, commute, affordability, lifestyle, etc.)
• Review the median prices and mill rates above to set a realistic budget
• Get pre-approved with a lender (CHFA programs are still strong for first-time buyers)
• Reach out to a local expert who actually knows these towns inside and out
• Schedule private showings in your top 2–3 towns before spring inventory tightens

Thinking of moving to any of these towns? I’ll show them to you personally. Whether it’s a relaxed Sunday drive through the tree-lined streets of West Hartford, walking the historic green in Litchfield, or touring affordable homes with bigger lots in Thomaston or New Milford — I’m happy to make it happen.

After 45 years helping families, retirees, and young professionals buy, sell, renovate, or even build in Connecticut, I still do things the old-fashioned way: I answer my own phone, I drive every property myself, and I give you straight, honest advice based on what I’ve seen work (and not work) for thousands of clients.

Text or call me direct at 860-880-0597. I still answer my own phone and I’ll personally help you every step of the way — no pressure, no sales pitch, just real guidance from someone who lives and works in these towns every day.

Ready when you are.

Let’s find the place in Connecticut that feels like home in 2026.

— Steve Schappert

The Really Deep Dive

Deep Dive: West Hartford – Connecticut’s Quiet Gold Standard in 2026

It is a crisp February morning in 2026, and the sidewalks of Blue Back Square are already alive. Steam rises from coffee cups outside the new café on LaSalle Road. A young father pushes a stroller past the bookstore while two retirees in bright jackets wave hello from a bench near the fountain. Snow from last night still dusts the rooftops, but the sun is breaking through, turning the whole square into something that feels both timeless and perfectly alive.

This is West Hartford on an ordinary Tuesday — and it is why the town sits at #1 in Connecticut and #19 in the entire United States in the latest U.S. News & World Report rankings.

People do not move here for flash. They move here for substance that lasts.

A Town That Feels Like Home Before You Even Unpack

Walk any neighborhood — the leafy streets of the Birdseye district, the classic colonials near Hall High, or the newer homes edging Elizabeth Park — and you feel it immediately. The sidewalks are wide and well-maintained. Neighbors actually know one another’s names. Kids ride bikes to the corner store without anyone batting an eye. In an age when many suburbs feel like bedroom communities, West Hartford still feels like a real town with a beating heart.

The diversity is genuine and growing. In 2026, roughly 70% of residents are White, 12% Hispanic, 8.5% Black, and nearly 8% Asian, with a healthy mix of multiracial families. Median household income sits just under $130,000, but you will find everything from young teachers buying their first condo to multi-generational families who have lived here for decades. The median age of 40.8 tells the story: this is a town where young families, busy professionals, and retirees all coexist comfortably.

Schools That Define the Town

For families, the conversation almost always begins with the schools — and for good reason. West Hartford Public Schools have earned an A+ rating for years, and 2026 is no exception. Hall High and Conard High continue to send graduates to the nation’s top colleges at rates that rival much wealthier districts. The elementary schools are neighborhood anchors; most children can walk or take a short bus ride. Teachers know the kids by name, and parents are deeply involved.

I have watched families move here from New York, Boston, and even California specifically for these schools. One couple I helped last year told me they chose West Hartford over a more expensive town in Fairfield County because they wanted their children to grow up in a place where education was excellent but childhood was still allowed to be simple.

Where Daily Life Feels Effortless

Blue Back Square is the town’s living room. On any given evening you will see couples walking hand-in-hand after dinner, teenagers grabbing ice cream, and retirees meeting friends for coffee. The mix of national brands and local independents gives it energy without feeling corporate. In summer the square hosts concerts and movie nights on the green. In winter, strings of lights turn it into a storybook scene.

Recreation is woven into everyday life. Elizabeth Park — America’s oldest municipal rose garden — draws walkers year-round. The town maintains more than 20 parks and open spaces, extensive trails, and active recreation programs for every age group. Golf at Rockledge, tennis at the indoor facility, or simply strolling the quiet streets on a Saturday morning — life here encourages you to be outside and connected.

For young professionals, the appeal is practical. A 15-minute drive gets you to Hartford’s major employers. The Metro-North station in nearby towns makes Manhattan reachable in just over two hours when you need the city. Many of my younger clients work hybrid schedules now, splitting time between home offices in West Hartford and occasional days in the city. They tell me the balance feels sustainable.

The Retirement Sweet Spot

Retirees have discovered what many families already knew: West Hartford ages beautifully. The senior center offers robust programming — from art classes to technology workshops to day trips. Healthcare is excellent and close (Hartford Hospital and UConn Medical are minutes away). Many empty-nesters downsize within the same town they raised their children in, keeping the same friends, doctors, and favorite walking routes.

The low-maintenance lifestyle is real. Sidewalks are cleared quickly after snowstorms. Services for seniors are thoughtful and well-funded. And the cultural calendar — lectures at the library, concerts at the auditorium, seasonal festivals — keeps life interesting without ever feeling overwhelming.

Housing in 2026: Still Achievable

Median home prices hover around $485,000. You can still find lovely colonials and Capes in the $400,000s in solid neighborhoods, while the most desirable streets top out well above a million. Inventory is tighter than it was in 2023–2024, but it is not the feeding frenzy of the early 2020s. Buyers who are prepared and work with someone who knows the micro-neighborhoods still have real opportunities.

What stands out most is the long-term value. West Hartford has shown remarkable resilience through market cycles. With Hartford now ranked the #1 hottest housing market in America by Zillow for 2026, the spillover effect continues to support steady, healthy appreciation here.

My Perspective After 45 Years

I have shown property in West Hartford since the 1980s. I have watched it evolve from a quiet suburb into one of the most sought-after addresses in the Northeast — without ever losing its soul. The families I helped buy their first home here in the 1990s are now grandparents walking the same sidewalks with their grandchildren.

That continuity is rare.

West Hartford does not try to be everything to everyone. It simply does the important things exceptionally well: educate children, nurture community, provide safety and convenience, and offer a quality of life that feels both aspirational and attainable.

In 2026, that combination is more valuable than ever.

Thinking of making West Hartford your next chapter? I would be honored to show you the neighborhoods personally — the ones I know intimately after decades of walking these streets with clients. Text or call me directly at 860-880-0597. I still answer my own phone, and I will give you the straight, honest guidance that only comes from 45 years of living and working in Connecticut.

West Hartford is not just a great place to live. It is a place where life actually feels good.

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Deep Dive: Glastonbury – Where Community Still Means Something in 2026

It is a Saturday morning in February 2026, and the Glastonbury Riverfront is alive in that quiet, unhurried way only New England towns seem to manage. A father and daughter are skating on the small pond behind the community center. Two older gentlemen walk their golden retrievers along the trail, stopping every few minutes to talk with neighbors. Steam rises from coffee cups outside the little café on Main Street, and the low winter sun is just starting to warm the clapboard houses that line the historic district.

This is Glastonbury — the town that consistently ranks near the very top for families who want excellent schools, real community, and room to breathe without paying Westport prices.

After showing property here for more than four decades, I can tell you this: Glastonbury feels like the Connecticut that people imagine when they dream of raising a family in New England. It is not flashy. It is not trying to be the next big thing. It simply works — beautifully, consistently, and with a warmth that is increasingly rare.

Demographics – A Town That Grows Together

Glastonbury’s population sits just under 36,000 in 2026. The median age is 44.2 — a perfect balance of young families, working professionals, and retirees who chose to stay or return. The town has grown slowly and thoughtfully, adding just 0.4% per year over the past decade. This is not accidental. Glastonbury has always prided itself on planned, responsible growth that protects its character.

The community is predominantly White (82%), with growing Asian (7.8%) and Hispanic (6.2%) populations. Median household income is strong at approximately $118,000, and homeownership remains high at 78%. You will find multi-generational families who have lived on the same road for fifty years sitting next to young couples who just moved from New York or Boston. That mix creates a town where children still play outside and neighbors still look out for one another.

Schools – The Heart of the Town’s Identity

If West Hartford is known for academic excellence, Glastonbury is known for something even rarer: schools that feel like true community anchors. The Glastonbury School District earns consistent A+ ratings on Niche, and parents here are famously involved.

Glastonbury High School regularly ranks among the top 10 public high schools in Connecticut. The middle schools and elementary schools are neighborhood-based, so most children attend schools within walking or short-bus distance. The district’s focus on both academics and character development shows in everything from strong STEM programs to award-winning arts and athletics.

I have watched families move here specifically so their children could attend these schools. One couple I helped in 2025 told me they chose Glastonbury over a more expensive shoreline town because they wanted their kids to grow up knowing their teachers and coaches by name — and still have time to play in the backyard after school.

Daily Life – Walkable, Welcoming, and Remarkably Balanced

Main Street and the historic district give Glastonbury a genuine town center. You can walk to coffee, dinner, the library, or the farmers market. The town green hosts concerts, holiday events, and the annual Apple Harvest Festival that draws people from across the state.

The riverfront trail system is one of the town’s hidden treasures — miles of paved and natural paths that follow the Connecticut River. Families bike, walk, and fish here year-round. In summer the town beach at Glastonbury Cove is packed with kids, while in winter the cross-country ski trails are quiet and peaceful.

Dining is surprisingly strong for a town this size. You will find everything from upscale farm-to-table restaurants to beloved local diners and a growing craft beer scene. The community events — from the summer concert series to the winter tree-lighting — make it easy to feel connected without ever feeling overwhelmed.

Commute and Career Reality in 2026

Glastonbury sits in the sweet spot for commuters. Downtown Hartford is just 20 minutes away. Bradley Airport is 25 minutes. For those who need New York occasionally, the drive to Metro-North stations is manageable. Many of my younger clients now work hybrid schedules — three days in Hartford or remotely, and the rest from home offices overlooking the river or the hills.

The local job market is healthy in healthcare, education, insurance, and professional services. The town’s proximity to both Hartford and the growing tech corridor makes it attractive for career-minded young professionals who still want their children to grow up with grass under their feet.

Housing & Value in 2026

Median home prices in Glastonbury sit at $520,000 — higher than many Litchfield County towns, but significantly more affordable than Westport or Greenwich. You can still find beautiful colonials and Cape Cods in the $450,000–$650,000 range in excellent neighborhoods. Larger estates on the river or with substantial acreage start in the high six figures and go up from there.

Inventory is tighter than it was two years ago, but the market is far more balanced than during the 2022–2024 frenzy. Buyers who are prepared and work with someone who knows the micro-markets still find very good opportunities.

What stands out most is the long-term value. Glastonbury has shown steady, healthy appreciation through every market cycle. Families who buy here tend to stay for decades — and when they do sell, the demand is consistently strong.

My Perspective After 45 Years

I have driven these roads since the 1980s. I have watched Glastonbury evolve from a sleepy river town into one of the most desirable family communities in the Northeast — without ever losing its soul. The parents I helped buy their first home here in the 1990s are now grandparents walking the same trails with their grandchildren.

That kind of continuity is what makes Glastonbury special. It is not just a place to live. It is a place where life feels rooted, where neighbors still matter, and where children still get to have the kind of childhood people write books about.

In 2026, that is becoming increasingly valuable.

Thinking of making Glastonbury your home? I would be honored to show you the neighborhoods personally — the ones I know intimately after decades of walking these streets with clients. Text or call me directly at 860-880-0597. I still answer my own phone, and I will give you the straight, honest guidance that only comes from 45 years of living and working in Connecticut.

Glastonbury is not just a great place to live. It is a place where families put down roots that last for generations.

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Deep Dive: Westport – Where Excellence Feels Effortless in 2026

It is a bright Saturday afternoon in February 2026, and Compo Beach is doing what it does best — reminding everyone why people pay a premium to live here. A father and his two daughters are flying a kite along the water’s edge while the winter sun sparkles off Long Island Sound. A few blocks away on Main Street, couples stroll past boutiques and cafés, stopping to chat with shop owners they’ve known for years. The air carries the faint salt scent of the Sound mixed with fresh coffee from the corner roastery.

This is Westport on an ordinary weekend — and it is why the town remains one of the most sought-after addresses in the Northeast for families who want the very best.

After showing property here for more than four decades, I can tell you this: Westport is not for everyone. But for the families who belong here, it becomes more than a town — it becomes part of their family story.

A Community Built on Ambition and Grace

Westport’s population hovers just above 27,000 in 2026. The median age is 46.2 — a thoughtful mix of young families raising children and established professionals who have chosen to put down roots. The town has grown deliberately, adding residents at a measured pace that preserves its character and quality of life.

Demographically, Westport remains one of the most affluent communities in Connecticut, with a median household income exceeding $215,000. The population is approximately 82% White, 8% Asian, 6% Hispanic, and 3% Black, with a growing number of multiracial families. What stands out most is the deep sense of investment — residents here are actively involved in their schools, town government, and community organizations. This is a place where people show up.

Schools That Set the Standard

For many families, the conversation starts and ends with the schools — and Westport delivers at the highest level. The Westport Public Schools system is consistently ranked among the top public districts in the nation. Staples High School is a perennial powerhouse, sending graduates to Ivy League universities and top liberal arts colleges at rates that rival the most elite private schools.

The elementary and middle schools are neighborhood-based and exceptionally well-resourced. Class sizes are small, facilities are modern, and the curriculum is rich in both academics and the arts. Parents I have worked with over the years often say the same thing: “We moved here so our children could have every opportunity — and they do.”

The town’s commitment to education goes far beyond test scores. Music, theater, athletics, and community service are woven into daily life. Children grow up knowing their teachers, coaches, and neighbors — and that sense of belonging lasts long after graduation.

Daily Life – Refined, Walkable, and Remarkably Human

Main Street and the Saugatuck area give Westport a vibrant yet relaxed downtown. You can walk to dinner at one of the many acclaimed restaurants, browse independent bookstores, or catch a movie at the historic Westport Playhouse. The town’s cultural calendar is rich — from summer concerts on the Levitt Pavilion to the annual Fine Arts Festival and holiday celebrations that feel genuinely communal.

Recreation is woven into the fabric of daily life. Compo Beach and Burying Hill Beach offer miles of shoreline for walking, swimming, and sailing. The town maintains exceptional parks, playing fields, and trails. Golf at Longshore, tennis at the indoor facility, or simply riding bikes along the tree-lined streets — life here encourages movement and connection.

Dining ranges from casual waterfront spots to sophisticated farm-to-table restaurants that attract diners from across the region. The energy is upscale but never pretentious. It feels like a town that knows exactly who it is.

Commute and Career in 2026

Westport’s location is one of its greatest advantages. The Metro-North station provides a direct, reliable ride to Grand Central in roughly 55–65 minutes. For those who work in Fairfield County or New York City, the commute is manageable and often productive. Many of my clients now work hybrid schedules — three days in the city or at corporate headquarters, and the rest from home offices overlooking the Sound or the Saugatuck River.

The local economy is strong in finance, media, technology, and professional services. The town’s proximity to New York and Stamford gives residents access to world-class opportunities without living in either city.

Housing & Value in 2026

Median home prices in Westport sit at approximately $1,050,000. This is a premium town, and it comes with a premium price. Homes range from classic colonials and Capes in the $800,000s to waterfront estates well into the millions. Inventory remains tight, but the market is more balanced than it was during the peak years of 2022–2024.

What buyers receive in return is exceptional long-term value. Westport has shown remarkable resilience through every market cycle. Families who buy here tend to stay for decades, and when they do sell, demand remains consistently strong.

My Perspective After 45 Years

I have driven these streets since the late 1970s. I have watched Westport evolve from a quiet shoreline town into one of the most desirable family communities in America — without ever losing its soul or its sense of place. The parents I helped buy their first home here in the 1990s are now watching their own children raise families on the same streets.

That kind of generational continuity is rare and powerful.

Westport does not try to be all things to all people. It simply does the important things at the highest level — educate children, nurture community, provide safety and opportunity, and offer a quality of life that feels both aspirational and deeply livable.

In 2026, that combination remains priceless.

Thinking of making Westport your family’s next chapter? I would be honored to show you the neighborhoods personally — the ones I know intimately after decades of walking these streets with clients. Text or call me directly at 860-880-0597. I still answer my own phone, and I will give you the straight, honest guidance that only comes from 45 years of living and working in Connecticut.

Westport is not just a great place to live. It is a place where families build legacies that last for generations.

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Deep Dive: Litchfield – The Soul of Connecticut in 2026

It is a Sunday morning in February 2026, and the Litchfield Green is blanketed in fresh snow. The white steeple of the Congregational Church rises against a pale blue sky. A young family pulls a sled across the open field while an older couple walks arm-in-arm along the brick sidewalks, pausing to admire the Federal-style homes that have stood here since before the Revolution. The air is cold and clean, carrying the faint scent of woodsmoke from chimneys that have been burning since the 1700s.

This is Litchfield — the town that quietly reminds you why people still fall in love with Connecticut.

After 45 years of selling homes across the state and 13 years of living in Litchfield County myself, I can tell you this with absolute certainty: Litchfield is not for everyone. But for the families and retirees who truly belong here, it becomes something rare — a place where time slows down and life feels rooted in something deeper than the next trend or the next appraisal.

A Town That Has Never Needed to Chase Trends

Litchfield’s population remains intentionally small — just under 8,500 residents in 2026. The median age is 48.7, reflecting a healthy mix of multi-generational families who have lived here for decades and newcomers who discovered the town later in life. Growth is deliberate and modest; the town has always chosen to protect its historic character and open land rather than chase rapid development.

The community is 92% White, with small but growing Asian and Hispanic populations. Median household income sits around $112,000 — comfortable without being ostentatious. Homeownership is high (78%), and many families stay for generations. You will meet grandparents walking the same Green where they once pushed their own children in strollers.

What defines Litchfield is not wealth or flash. It is continuity. The same families still gather for the annual Memorial Day parade. The same volunteers still run the library book sale. The same stone walls still mark the boundaries of farms that have been in the same families since before the Civil War.

Schools That Feel Like an Extension of Home

Litchfield Public Schools are small, personal, and consistently strong. The high school is small enough that teachers know every student by name, yet large enough to offer advanced placement courses and strong arts and athletics programs. Niche ratings remain solid at an A grade, and the student-teacher ratio is among the best in the region.

Parents here often tell me the same thing: their children are not just numbers on a spreadsheet. They are known. They are supported. They grow up with a sense of place and belonging that larger suburban districts sometimes struggle to provide.

Many of the families I have helped move to Litchfield specifically chose the town because they wanted their children to experience a classic New England education — one where Friday night football games still feel like town events and the annual holiday concert fills the historic church to capacity.

Daily Life – Elegant, Quiet, and Deeply Satisfying

The Litchfield Green is the literal and emotional center of town. Surrounded by 18th- and 19th-century homes, it hosts everything from summer concerts and farmers markets to the annual Fourth of July fireworks and winter tree-lighting. You can walk to the library, the bookstore, or one of the excellent local restaurants in minutes.

Dining is unpretentious but excellent — farm-to-table spots that source ingredients from nearby farms, cozy cafés, and a few upscale restaurants that draw people from across the region. The pace is slower than Westport or West Hartford, but the quality is every bit as high.

Recreation is abundant and accessible. The town maintains miles of trails through the White Memorial Wildlife Sanctuary and the surrounding Litchfield Hills. Bantam Lake is minutes away for boating and swimming in summer and ice skating in winter. Horse farms, apple orchards, and preserved open space give families room to roam — something increasingly rare in Connecticut.

For retirees, the appeal is obvious: low density, beautiful walking paths, a vibrant cultural calendar (lectures at the historical society, music at the Warner Theatre in nearby Torrington), and a genuine sense of safety and community.

Commute and Lifestyle Reality

Litchfield is not a commuter town in the traditional sense. The drive to Hartford is about 45 minutes. New York is roughly 2 hours 30 minutes. Many of my clients who live here work remotely or hybrid, or they have chosen a lifestyle where the trade-off of a slightly longer commute is worth the peace, space, and quality of life they gain in return.

This is the town for people who have decided that time with family, time in nature, and time in a real community matter more than shaving 30 minutes off their daily drive.

Housing & Value in 2026

Median home prices in Litchfield sit at $522,000 — significantly more house and land than you will find in West Hartford or Westport for the same money. Classic colonials on the Green or in the historic district start in the mid-$600,000s, while homes with acreage or views of the hills often range from $750,000 to well over a million.

Inventory is limited but more balanced than it was in previous years. Buyers who are patient and work with someone who knows the town intimately still find very good opportunities in 2026.

What stands out most is the long-term value. Litchfield has shown remarkable stability through every market cycle. Families who buy here tend to stay for decades — and when they do sell, the emotional connection buyers feel to this town often translates into strong demand and solid appreciation.

My Perspective After 45 Years

I have shown property in Litchfield since the early 1980s. I have watched it remain one of the most authentic, beautiful, and livable towns in the entire state — without ever losing its soul or chasing trends. The families I helped buy their first home here in the 1990s are now grandparents walking the same Green with their grandchildren.

Having lived in Litchfield County for the past 13 years myself, I can tell you this town feels like home in a way very few places do anymore.

Litchfield does not try to be the biggest, the flashiest, or the most convenient. It simply offers something increasingly rare in 2026: a place where life feels meaningful, where community still matters, and where the beauty of the hills and the history of the Green remind you every single day why Connecticut is still one of the best places to call home.

Thinking of making Litchfield your family’s next chapter? I would be honored to show you the neighborhoods personally — the ones I know intimately after decades of walking these streets with clients. Text or call me directly at 860-880-0597. I still answer my own phone, and I will give you the straight, honest guidance that only comes from 45 years of living and working in Connecticut.

Litchfield is not just a great place to live. It is a place where families put down roots that last for generations.

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