A historic downtown, shopping corridors and family farms

Once a farming and manufacturing town, Shelton has grown into a small city with all the classic features of a Connecticut small town. The historic downtown is built along the Housatonic River, hosting small businesses, established warehouses and waterfront parks. “Mayor Lauretti has taken great care of the downtown area. It’s been redeveloped as a place where people can walk to local restaurants from their apartments,” says Paula Bachman, broker/owner at Property Choices Real Estate, who has lived in Shelton for 30 years. Commercial corridors offer convenient shopping options, and much of the neighborhood is made up of peaceful subdivisions. To the west, established family farms offer a steady supply of fresh produce, local parks encourage locals to go hiking or fishing, and the city’s active local government fosters community engagement with regular events, like weekly summer concerts.

Downtown condos and Colonial Revivals with large yards

Homebuyers in Shelton can choose between condos and historic multifamily properties on busier streets closer to downtown or quieter residential streets with more spacious yards. Condos in renovated brick buildings from the late 19th century cost between $200,000 and $300,000. Townhouses from the early 2000 cost between $400,000 and $550,000, while smaller single-family homes from the mid-to-late 20th century appear in ranch and Colonial Revival designs and are priced between $500,000 and $750,000. Freshly built New Traditional homes on larger lots cost between $900,000 and $1.3 million. Diverse housing options aren’t the only consideration that draws residents to the neighborhood. “Taxes are ridiculously low. Shelton’s is 17.4 mills; just for comparison, [nearby] Trumbull’s is double that — it’s about 35 mills,” Bachman says.

Parks along the Housatonic to walk or fish

Locals explore walking trails by the Housatonic River or enjoy a picnic while their kids run around the playground at Riverview Park. Southbank Park is another popular riverfront spot to go fishing, launch a boat or have a picnic by the Housatonic River. For longer walks, the paved Shelton Lakes Recreation Path weaves for 4 miles through the neighborhood and offers views of Hope Lake, Silent Waters and Pine Lake. Dog owners can chat with their neighbors as their pets run around the Shelton Dog Park, and the tennis courts and ball fields at East Village Park are a go-to for youth sports games. Golfers enjoy the 18-hole course at the Brownson Country Club.

Outdoor seating by the river at Pier131 Kitchen and Bar

The historic brick buildings downtown host popular local restaurants, while commercial corridors have chains and big box stores. Downtown, Pier131 Kitchen and Bar serves residents oysters and elevated American dishes on an outdoor patio with views of the Housatonic River, and Tacomida offers margaritas and tamales in a trendy, industrial-inspired environment. After dinner, locals can grab drinks and play pool at the Pub on Howe. Further away from downtown, there are family-owned restaurants like Wellington, an upscale American restaurant serving pasta and filet mignon. Shelton has a seasonal farmers market downtown, but residents can find farm-sourced meat and produce year-round at the Stone Gardens Farm Market, which Bachman says, “has the absolute best corn that’s grown locally.” Shelton also has widely recognized stores throughout the neighborhood, like a Stop and Shop at the Shelton Square Shopping Center, as well as TJ Maxx and Hawley Lane Shoes. “I always say that if they put in a Costco, I’d never leave town,” Bachman jokes.

Shelton Day has music, food and pony rides

Local farms in the western portion of Shelton host seasonal outdoor activities. The Jones Family Farm, which has been in business for 150 years, offers blueberry and strawberry picking in the summer and pumpkin picking in the fall. Locals can return to choose a fresh pine for the holidays or visit the Jones Winery year-round to sip a wine flight. The community gathers for Shelton Day every October, a citywide festival with food trucks, live music, a petting zoo and local vendors. Wednesday summer nights are spent on Huntington Green, for a concert series called Music Under the Stars. “Kids love the concerts, of course, because they get to run around and dance,” Bachman says. There are also smaller activities throughout the city, like Nights with Shakespeare at R.D. Scinto — “they hire a performer named Leo Schaff to teach us Shakespeare on Tuesday nights, which is very fun. Right now, we’re doing Romeo and Juliet,” Bachman says. The performance includes energetic readings of Shakespeare’s plays, modern translations and audience discussions.

Dual enrollment at Shelton High

Kids may begin at Long Hill Elementary, which serves grades prekindergarten through 4 and has a B-plus rating from Niche. Students can progress to B-rated Perry Hill School for grades 5 and 6 and then to B-plus-rated Shelton Intermediate School for grades 7 and 8. Older students continue learning at B-rated Shelton High, which offers dual-enrollment options for students to begin earning college credits for classes like video game design, entrepreneurship, accounting and more.

Commuter rails and state routes

Just across the Housatonic River is the Derby/Shelton train station, where commuters can catch the Waterbury line to reach Bridgeport in 20 minutes. The Bridgeport train station has routes operated by the Metro-North Railroad that go southwest to New York City or northeast to Boston. Most of the neighborhood is car-dependent, and residents can merge onto state routes to travel south and link with Interstate 95.

A vibrant core to Connecticut's largest city

Downtown Bridgeport may not be the booming core of a thriving industrial city anymore, but its bright murals, local restaurants and theaters offer glimpses of the creativity shaping its future. “Downtown was thriving when I was younger, but a lot of businesses left by the 70s and 80s,” says John Hackett, broker of the John Hackett Team at William Raveis Real Estate, who was born and raised in Bridgeport. “There are efforts to rebound now,” he adds. Bridgeport Downtown Special Services District supports local businesses and sparks artistic efforts. As residents walk to a restaurant or brewery downtown, they’ll notice geometric, rainbow-colored murals and art installations sprinkled among the historic churches and high-rises. Though decommissioned power plants still make up part of the city’s skyline, event spaces have replaced some of the older warehouses, creating a trendy, industrial atmosphere.

Italian fare from Ralph 'n' Rich's 

Downtown has newly added dining spots and long-time community favorites. “Ralph 'n' Rich's has been a landmark for years,” Hackett says. The Italian restaurant, which was founded by Ralph Silano and Rich Ndini in 1990, is popular for its authentic pasta dishes and oyster raw bar. EAT Noddle and Rice serves pho in a trendy, warm-toned environment, while Joseph’s Steakhouse offers lobster and steak for an elevated night out. Brewport Brewing Co. is a laidback taproom where locals can grab a beer and a slice of pizza in an industrial-style setting. Stores like An’s Jewelry and Kindred Thoughts Bookstore offer unique shopping options, but locals must leave the neighborhood to go grocery shopping. The nearest supermarket is Save A Lot, which is a mile northwest of Downtown Bridgeport.

Musicals, comedy shows and concerts downtown

Large arenas and venues are popping up where industrial plants used to sit — the Hartford HealthCare Amphitheater and the Total Mortgage Arena are two popular recent additions to Downtown Bridgeport. “There is a slew of bands that have played at the amphitheater, and events and festivals come to the indoor arena,” says Paula Bachman, broker/owner at Property Choices Real Estate, who has served the area for 16 years. “I saw Earth, Wind & Fire there last year,” Bachman adds. Locals can catch musicals and concerts at the Downtown Cabaret Theatre or laugh along to stand-up performances at Vinnie Brand's Stress Factory Comedy Club. The city hosts community events at McLevy Green, like the annual holiday tree lighting and downtown farmers market, where locals can shop for fresh produce every Thursday from July to October. “There’s also a ferry that goes out to Port Jefferson on Long Island. You can take your car on it and go explore all the restaurants and shops around there for a day,” Bachman says.

Brick condos and high-rise apartments

Nearly all residents rent apartments, as there are few houses downtown. Occasionally, homebuyers can find condos in 20th-century brick buildings. Condos usually cost between $180,000 and $230,000.

Benches and walkways at city parks

Pocket parks offer small stretches of green space in the urban environment. Kids can play baseball at Riverfront Park, which is positioned by the Pequonnock River. Residents can enjoy the landscaped walkways and benches at McLevy Green, which hosts the downtown farmers market and summer concerts. City Hall Park also offers a green lawn with benches to enjoy a peaceful moment in the heart of the city. If they want to take a coastal walk or enjoy the sand beach, residents can travel to Seaside Park.

Trains route to Boston and New York City

Locals can walk to restaurants and shops throughout downtown, but they can also catch a bus operated by Greater Bridgeport Transit to get around the city. There are the regular trains serviced by Metro-North Railroad. “The downtown station has a train that goes down to New York City in about an hour and a half for commuters,” Bachman says. “There are also trains that go to Boston and D.C., so it’s very convenient.” State routes run through the western edge of the neighborhood and link with Interstate 95, making connecting with major roadways simple for those who opt to drive. Downtown Bridgeport has an overall CAP Index Crime Score of 9 out of 10, compared to the national average of 4.

Art installations at Housatonic Community College

Kids can begin at Roosevelt School, which serves students in grades kindergarten through 8 and has a C-minus rating from Niche. Older students progress to Bassick High, which has a D-plus rating. There is currently a new building for Bassick High in development, which will introduce career preparation programs. The school is set to be ready for the 2025-2026 school year. The Housatonic Community College is also downtown, and residents can explore the college’s art museum, which has a sculpture garden and visual exhibits.

Fairfield County, CT, is known for its diverse communities and proximity to both urban and suburban amenities. The region offers a variety of housing options, from historic homes to modern developments, catering to different lifestyles and needs. With strong transportation links to New York City and a reputation for excellent schools, Fairfield County is a desirable location for families and professionals alike.

New Haven County, located in south-central Connecticut, offers a diverse range of communities, from urban settings to suburban neighborhoods. With a rich history and a variety of cultural attractions, including museums, theaters, and parks, the region provides residents with ample recreational and educational opportunities. The county is also home to several higher education institutions, including Yale University, enhancing its reputation as an area rich in academic resources.