That kind of front-porch culture is largely absent from modern subdivisions, where a person can enter his house through the garage, then exit into a fenced-in backyard without ever speaking to, or even seeing, a neighbor except through the dark tinted glass of an SUV.
An old neighborhood like Maple Street fosters a feeling of community, and that is one of its best attributes, he said.
Wood and Ken Goode have lived in the house at 402 S. Maple St. for 10 years, having moved to Winchester from California by way of Lexington.
The two men were living in an apartment downtown, where they had a restaurant, Cafe Collage, and were looking for an older house when a friend told them about the one at the corner of Maple and College. They looked at the house, thought it was just right, and made an offer.
"It just looked like the kind of house I could move into and start cleaning up and restoring," said Wood, who is something of a handy man.
It required a lot of work. They sanded all the floors, replaced windows, painted the whole place.
"We replaced seven layers of wallpaper and took it down to the original plaster, and patched cracks and re-drywalled the ceilings, and did the electrical and everything," Wood said.
But it was worth it.
"After living in a house like this, you go into new homes, and the ceilings aren't quite as tall, and you feel more closed in. It's great to have this kind of space. Big windows. Bigger rooms. You can escape from each other if you want to, and you won't even know."
Wood said he has always liked older houses and neighborhoods that are within walking distance of downtown.
The son of a Baptist minister, Paul grew up in a small town on a street with no fences.
"We'd play kick the can and start in one yard and end up four or five houses down," he said.
He wanted that kind of neighborhood again.
It's the kind of neighborhood Charles Hendricks also knew as a boy.
Hendricks, 58, grew up in the house at 437 S. Maple St., which he and his wife, Cheryl, are sharing with their daughter, Erin, her husband, Shane, and granddaughters Ella and Anabelle, because Erin's house was recently damaged in a fire.
There's more than enough room for all three generations.
In all, five generations of the family have lived in the big old house. Hendricks' mother moved there when her aunt died, and then in 1993, Charlie and Cheryl returned to it when his mother died.
One reason was the nostalgia he had for his boyhood home.
"Growing up here was almost like living in the country in the middle of town," he said.
One neighbor, Hub Spencer, had a cornfield nearby, and when it didn't have corn, it grew up in weeds. There was a little stream running through it where boys would catch small creatures.
In the summer, he said, "we would stop traffic, and we would sell puppy dog tails, snakes, crawdads."
(He explained that they didn't catch and cut puppies' tails, the owners cropped them.)
The children would also ride their bikes through backyards, and pick cherries and apples from the neighbors' trees to make pies. Nobody seemed to mind.
There were some magnificent trees, Hendricks remembers. Giant hemlocks and oaks, as well as fruit trees like pears, plums and paw paws. And the sidewalks were lined with maples, as befitted the street's name.
"There were treehouses everywhere, and forts," he said. "Every house had a garage, and we probably knew how to get into every garage, locked or not."
One family even had a barn where they kept a horse.
In the winter, children would rope off the top of the street and go sledding downhill.
It was a boy's paradise.
Everyone knew their neighbors. Each child knew which women would give them chocolate fudge, jellybeans and other treats.
But there was a down side to the closeness among neighbors. Several teachers lived on the street, and if a kid misbehaved in school, his parents would know about it when he got home.
Hendricks, who co-owns and manages Three Toads Farm, had expressed an interest in moving back to the old home place after his mother died, but his father tried to dissuade him.