SHORELINE TOWNS WITH BEACHES AND TRAIN STATION
Milford (I-95 exits 34-40)
Milford is a vibrant coastal town with a charming village,
a scenic harbor, and more than 17 miles of shoreline along Long Island Sound.
It offers a mix of beaches, parks, and recreational amenities including Silver
Sands State Park and Walnut Beach. The historic Milford Village Green hosts
events year-round, and the town center features boutique shopping, restaurants,
and cafés. Milford also benefits from a Metro-North train station, making it a
convenient spot for commuters and weekenders.
West Haven (I-95 exit 42-43)
West Haven is a diverse city with a mix of neighborhoods, a
strong sense of community, and a long stretch of publicly accessible beachfront
— the longest in Connecticut. The West Haven Boardwalk is a popular place for
walking, jogging, and enjoying seaside views. The city also offers parks,
playgrounds, and a growing number of local restaurants and cafés. It is home to
the University of New Haven and has a Metro-North station for convenient access
to New York City.
INLAND TOWNS - SHORT DISTANCE FROM BEACHES AND TRAIN STATION
Woodbridge (Merritt Parkway exit 59)
Woodbridge is a quiet, residential town known for its wooded landscapes, spacious properties, and top-rated public schools. It offers a peaceful, suburban environment with easy access to hiking trails, including those in the West Rock Ridge State Park. Woodbridge is popular with those seeking privacy and a country-like setting just minutes from New Haven.
Orange (I-95 exit 41, Merritt Parkways exit 56)
Orange combines small-town charm with suburban convenience. It has a strong community feel and a range of retail and dining options — particularly along the Boston Post Road. The town hosts seasonal events like the Orange Country Fair and has preserved open spaces, farms, and walking trails. With easy access to I-95 and Route 15, Orange is well-located for commuting while maintaining a relaxed, residential atmosphere.
For nearly twenty years, I've helped New York City and Boston renters stop waiting for "someday" and start owning a place of their own. As a former Manhattan renter myself (West 82nd Street), I know that buying a weekend retreat isn't just about escaping the city. It's often the first step toward building equity while continuing to enjoy the city life you love.
That's the idea behind Buy Your Second Home First. Sometimes the smartest first home is the one everyone else thinks should come second.