Middletown

First established as a port on the Connecticut River in the early eighteenth century, Middle Haddam takes pride in maintaining its historical status. Listed on the National Register of Historic Places in 1984, there are 58 historic buildings in the district, a majority predating 1835 including the library and post office. Surrounded by parks and lakes, Middle Haddam residents can enjoy outdoor recreation, such as the Air Line State Park Trail. “These old railroad lines have been turned into trails,” says Todd Hatfield, a realtor with Executive Real Estate and resident of Middle Haddam for 30 years. “Because the trains couldn’t go uphill, the trails are nice and level.” Many of the buildings in Middle Haddam were constructed in the Federal style between 1790 and 1835, but this style of home only goes on the market occasionally. A refurbished home from the 1800s could sell for around $525,000. “Historic houses used to take longer to sell because of the maintenance,” says Hatfield. “But everything is selling faster because of low inventory.” However, there is new construction happening outside of the historic district in a small development on Long Hill Road. These Colonial and Cape Cod homes range from $480,000 for 2 bedrooms to $600,000 for 5 bedrooms. Houses built in the 90s and 00s can also be found in that price range, they tend to be more spaced out and sit on partially wooded lots. Hurd state park sits to the south of Middle Haddam and is the neighborhood's primary place for public outdoor activities. Comprised of 991 acres of dense forest, the park provides hikers and mountain bikers with a vast trail network. It's also common to see park visitors go on guided and independent horse rides under the shady canopy. Hurd Park is also on the east bank of the Connecticut River, making it a hotspot kayakers, boater and fishers. In the winter, the park becomes the premier destination for activities like cross-country skiing. Pizzeria DaVinci has been serving slices and grinders on West High Street for over 10 years. Grocery Shopping can be done at the Stop & Shop by Lake Pocotoppaug in East Hampton, 3.2 miles up West High Street. This area is also home to several chain and local dining spots like the Lakeside Bar and Grill in East Hampton. The establishments offer weekday specials and live music on the weekends. The lake’s clear waters are visible from the outdoor seating section. Fire Ring Farm on is a local community funded agribusiness that helps support Middle Hadam and other nearby communities with locally grown produce and event spaces. Some of hosted events include summer camps and herbalist classes. The farm's Summer Camp Program is provided by the Everyone Outside Children's Program and can included nature tours, harvesting and herb mixing classes, nature journalling and even frog catching. Elementary-aged students can attend Center School off of Summit Street, which gets a B rating on Niche. In 2023, it opened a grant-funded greenhouse to provide fresh food and learning opportunities for its students. East Hampton Middle on Childs Road scores a B-minus on Niche. The school's theater department hosts student performed productions like Beauty and the Beaston the weekends. East Hampton High is off of North Maple Street and gets a B-grade from Niche. Middle Haddam is almost completely car dependent, with little to know sidewalks, large spaces between amenities and only two bus stops for the entire area. Middle Haddam Road and West High Street are the neighborhood's two main throughfares and all other local roads sprout from them. The few minor roads that exist are narrow and winding and typically don't get regular replacements due to low traffic. With Middle Haddam Road and Portland-Cobalt Road turning into highways 151 and 66, a trip to nearby Portland and Middletown are only 5.6 miles away. Given that Middle Haddam is registered as a historic region, the Middle Haddam Historic District Commission governs the area's zoning. Folks looking to build homes or facilities in the Historic District are likely to face a number of restrictions and regulation meant to preserve the area's physical culture. Property owners must apply for a certificate of appropriateness when making exterior changes that can be viewed publicly.

Flanking Interstate 91’s west side in south-central Connecticut, the Highland neighborhood consists of a series of small subdivisions set within foliage in Middletown. Residential housing began to take root in the past half century or so, superseding the farms that primarily occupied it before. Despite its seeming remoteness, locals are less than 10 miles from Cromwell and Middletown and have access to annual events, which range from Pride celebrations to holiday parades. “Highland is within the city of Middletown,” says Siobhan McLaughlin, a senior sales associate and team leader for the Siobhan McLaughlin Team. “It has a very New England country and rural feel, yet you are part of a small city, which is great because you have all the convenience and activities you would find in a bustling, small city.” Despite few prominent local businesses and diners in or alongside the neighborhood, the total number of which could be counted on one hand, Highland’s balance comes in the form of its proximity to the larger cities paired with its rural environment. “You feel like you’re in the country, but within a 5-to-10-minute drive, you have everything you need,” McLaughlin, who grew up in the area, says. Interstate 91’s breadth runs northward from Connecticut to the Canadian border, and as such Highland residents aren’t far from taking a trip north to Hartford, Springfield or beyond. “It’s a bucolic country retreat,” McLaughlin says. “There’s historic homes, horse farms and it’s a beautiful area to walk, with some nice vistas. It’s a very beautiful area of town.” Colonial-style homes are the most common form of architecture in the Highland neighborhood, along with some Cape Cods and ranch-style homes mixed into the landscape. “That part of town runs the gamut,” McLaughlin says. “You have newer constructions, rather large homes that could be over or around $1 million, or mid-century, smaller homes that may be closer to $300,000.” Some properties can even date to the 1700s. “It still has that nice, country feel,” McLaughlin says. “There’s a lot of historic homes.” The area also has a CAP crime score of 1 out of 10, significantly lower than the national rate of 4. Homes in Highland are spread out, adding to the rural atmosphere, and larger lots are common. “It has a quaintness and New England feel, yet you are smack in the middle of the state and just minutes from every convenience,” McLaughlin says. “It kind of gives you the best of both worlds. It’s a great little area.” Prices usually range between $300,000 and $700,000. “There’s definitely some closer, more densely populated little cul-de-sac developments that were built in the 1980s with the sidewalks,” McLaughlin says, “or you could have a mid-century house that has an acre with a little barn in the back.” The Red Fox Restaurant sits just off of the east side of Interstate 91, serving as the closest restaurant to Highland’s residential areas. Its menu ranges from seafood and pasta to steaks and a buffet setup, and the establishment also offers catering. Residents often head into Middletown or Cromwell for more options. “Any restaurant you could ever want is along Main Street there,” says Matthew Egan, a broker associate with Regency Real Estate. “There are some really cool tapas places and a really nice vegan restaurant, which is called It’s Only Natural. There’s always awesome dining.” Less than 3 miles north, the Cromwell Diner has stood for more than 30 years and serves classic American fare. Near the diner, Café Fiore offers Italian food to customers. Shoppers also have to head beyond Highland’s borders. “In Highland proper itself, there’s really no businesses other than the McInerny Flower Shop,” McLaughlin says. “It’s literally the only business in Highland.” The family-owned florist storefront is a local staple. For general needs, there is a Walmart less than 2 miles north in Cromwell, while grocery shoppers head to about five miles east to Market 32 in Middletown. “Growing up here, we tended to do our grocery shopping in the Cromwell area,” McLaughlin says. “The closest grocery shopping is in Cromwell. Cromwell, Berlin and Meriden are very close by. There are a lot of different areas to experience, so it is convenient to all of those as well. In Cromwell, there’s a lot of shopping.” Lamentation Mountain rises less than 1,000 feet on the west side of Highland, but it is the site of the Alice Fern Bruce Preserve, which spans almost 50 acres and offers trails for visitors. “There’s a lot of activities close by,” McLaughlin says. “The Blue-Blazed Trail goes through part of Highland, so there’s a lot of hiking opportunities.” Doctor Francis Giuffrida Park is less than 5 miles southwest, spanning almost 600 acres and encompassing multiple trails, lookouts at the surrounding landscape and more. “Lamentation Mountain and Giuffrida Park are the closest recreational areas,” McLaughlin says, “because a lot of Highland is privately-owned.” Hikers can also take to the Highland Pond Preserve, while golfers hit the links at Miner Hills Golf Course across Interstate 91 to the east. Other conservation areas and preserves sit in the surrounding area. Even in the farthest reaches of Highland, from the subdivisions set within the rural landscape, residents are less than 3 miles from accessing Interstate 91. “That’s the nice thing about it,” McLaughlin says. “Even though you feel like you’re in the country, you can get on major highways.” Via the interstate, New Haven is less than 25 miles south, while Hartford is under 20 miles north. Drivers can reach the Berlin Turnpike, which runs through Hartford and New Haven counties, in less than 5 miles north. “They call it the Berlin Parkway because it goes from New Haven to Hartford, and there’s all sorts of restaurants, shopping and events along that road,” McLaughlin says. A number of locations in Highland are on the National Register of Historic Places, thanks to their cornerstones dating to several centuries ago. Though Highland doesn’t have many events itself, being a part of Middletown means residents aren’t far from annual gatherings. “Middletown has a ton of events,” McLaughlin says. “Downtown Middletown is a happening place. There’s always something going on and there are tons of festivals.” Middletown PrideFEST takes place in the early summer each year and is hailed as the biggest Pride celebration in the entire state. “People come from all over,” McLaughlin says. “There’s always so much going on in Downtown Middletown. There are always art shows, craft shows and everything.” Other gatherings include seasonal celebrations and car shows. “They have a holiday stroll every weekend during the holiday time,” McLaughlin says, “and car shows, which totally shut down Main Street." Residents are close to other area events as well, including holiday celebrations in Westfield to the east. “Westfield has their own Memorial Day parade, and it’s amazing,” McLaughlin says, adding that local scout troops, the fire department and other organizations take part. “Everyone gathers at the fire department afterward to have hot dogs and beer. It’s a very small, community event – it’s very quaint.” Though there aren’t any schools within the neighborhood itself, Moody Elementary School is located across Interstate 91 to the southeast and serves as a starting point for students in the area. It scores a B-plus with Niche, while Beman Middle School, formerly Woodrow Wilson Middle School, receives a C-plus rating. Middletown High School gets a B from Niche, offering a student-to-teacher ratio of 11 to 1 and campus publications like a yearbook, newspaper and creative arts magazine.

With some farmland now being used for more houses and businesses, Westfield is a growing neighborhood in Middletown, Connecticut. "It’s always been a little bit more city," says Linda O'Hara, a real estate agent with William Raveis Real Estate and Middletown resident, "It's a hop, skip and a jump from the Berlin Turnpike, which gives access to New Haven." Despite its proximity to the city, Westfield still maintains plenty of forest land. Rabbits, owls and snakes are just some of the wildlife inhabiting the woods. The balance of metropolitan and agriculture makes this neighborhood popular with families and commuters. Homes in Westfield may sit on large lots, often in cul-de-sacs that are surrounded by large trees blocking the view of the house next door. Nearer to the highway, houses are closer together in subdivisions where colonials and ranch styles are common. Housing prices tend to be less expensive than in surrounding areas. Fixer-uppers can go for as low as $150,000 while newer builds tend to sell for around $470,000. Condos sell from around $125,000 to $225,000 with amenities like tennis courts and an outdoor pool.