Nostalgia is an important concept in the study of heritage tourism, especially as a push factor, but less attention is devoted to how nostalgia influences place attachment and vice versa, especially in relation to both individual and collective community experiences. While place attachment has been discussed in the context of second homes, nostalgia has received little attention, with none directed specifically at historic second home communities or those which had recently experienced a disaster. Therefore, this paper presents an analysis of semi-structured interviews conducted among second homeowners in Ocean Beach, New York, which is a century-old second home community with a rich local heritage that was hit by Hurricane Sandy in 2012. The findings show that the respondents display different aspects of nostalgia, in particular endo- and meso- nostalgia. This work conceptualizes meso-nostalgia as an umbrella term for the previously discussed nostalgias which focus on the gray area between personal and collective memories. The findings also show the respondents’ deep connection to the second home landscape, but there was a marked difference between respondents with inherited second homes and those who had purchased them wherein inherited homeowners’ nostalgia was closer to those of permanent residents in previous studies.