Unique and historic seemed to top our favorite Dream Homes of 2025.

The act of choosing one home among the many offerings on the North Fork to be our weekly “Dream Home” is already a challenge—how to pick just one? Now, the task of choosing my favorite among those 52 for the year-end roundup is nothing short of arduous. (I know, first world real estate problems!)

Since I can’t pick just one, here are a few that captivated me this year. 

Everything was perfect about this classic Craftsman cottage in Greenport. I loved the approach to the front with its native-plant-lined flagstone path and inside, the intact architectural details stole my heart. I was already imagining the kitchen with period cabinetry and placing my furniture in the rooms. I stopped short of selling my own property to finance this one, but I did submit a serious inquiry to the agent. A girl can dream, yes?

It was hard not ignore this cove-hugging hideaway on Shelter Island—a home so complete with comfort and amenities, you’d never have to leave. The beautifully renovated kitchen itself makes me want to spend a year in there ala “Julie & Julia,” the blog in which the author undertakes a year of recipes in Julia Child’s iconic cookbook. But outside is just as marvelous, with tiered landscaping, a flower cutting garden and Menantic Creek views. 

Last week’s converted barn in Southold ranked high for its history, charm and potential. This property comes with a fun, typically North Fork history – it once belonged to a prominent crops farmer from the Fleet family who was also a horse breeder. The 1830s frame barn that once housed trotters has been cleaned up and restored to a seasonal indoor/outdoor entertaining space. With a full renovation, it has potential to be a spectacular space all year ‘round. 

I loved this quirky former barn with a historic water tower in Mattituck (are you sensing a theme here? The natural stone and wood interior gives the place a comfy lodge vibe, and there are lots of interesting spots for creative uses—studios, reading nooks, galleries. The grounds are just enough wild to be interesting, but also tamed by meandering redbrick paths. But that tower! Talk about untapped potential! Built in 1898, and one of only three left in the Southold township, it’s six stories of glorious possibilities.

This Orient retreat, loving renovated and customized over its 30 years of ownership by an artist was one of the more unusual listings of the year. Everything about the interior is bespoke—and not in a generic on-trend kind of way, but and full of personality. This has a neat mix of home colors and natural textures, some polished details like the Scandinavian-styled wood-burning stove. The agent said “This has human scale and is not a show-off kind of house,” and I couldn’t have described it better. 

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