Milford

Downtown Milford is a boater’s paradise. Its location on the Long Island Sound and its many docks along the Milford Harbor, which runs vertically through the middle of the neighborhood, makes it easy to spend an afternoon on the water. However, there is so much more to this coastal community than boating. "It's an old New England town with a town center, so it has that authentic feel, especially being on the water," says Wojtek Borowski, a Realtor with Pearce Real Estate and a New Haven resident for over 30 years. Residents get easy access to Silver Sands Park, popular in the summer for its beaches, boardwalk, and Long Island Sound. The park also offers fishing, and it's common to find anglers pulling striped bass and summer flounder out of the water. For exercise, locals head to Wilcox Park, where area kids play ball on the multiple baseball fields, and friends challenge each other to a match on the tennis courts. And while not a traditional park, the Milford Green is a popular green space featuring a gazebo and benches for relaxing, tall shady trees and open space for kids to run and play. Homes closer to the water, especially along Trumbull Avenue, tend to be extensive, expensive and coveted for their views of the Long Island Sound. Most are impressive storybook cottages with expansive front porches and many windows facing the water. Further north, houses are just slightly smaller but still impressive; large Colonial Revivals, Cape Cods and contemporary builds sit on verdant lawns surrounded by tall trees. Closest to Interstate 95, homes run smaller; cozy ranch-style houses and bungalows sit close on narrow lots along sidewalk-lined streets. Prices range from $105,000 for 780 square feet to $2.3 million for 3,700 square feet. Condos and townhouses are also available throughout the neighborhood, ranging from $205,000 for 840 square feet to $899,000 for 2,400 square feet, offering amenities including walkability to shops and restaurants and beautiful views for units close to the water. The spring and summer are busy with multiple annual events. Among them is the Easter Eggstravaganza, which happens each April at The Milford Green. Businesses host an Easter Egg hunt in their stores, and kids take pictures with the Easter Bunny. Also popular is the farmers market, which runs on Saturdays from June to October at Wasson Field and features produce and goods from throughout the state. Downtown Milford has several national chain grocery stores in the neighborhood, like Aldi, Big Y and Shop Rite, where residents pick up food and essentials, and just a few miles northeast down Route 1 are more retailers like Target, Walmart, Whole Foods and Costco. For dining out, residents have many locally owned restaurants to choose from, many of which sit along Milford Harbor. Locals love Stonebridge for its seafood classics like lobster rolls, fish tacos, Mediterranean calamari and outdoor patio, where patrons can watch the sunset while they enjoy their dinner. Another neighborhood favorite is SBC Restaurant and Beer Bar, which offers craft beer, hearty pub food and a cozy atmosphere. Downtown Milford's youngest residents often start their education at Mathewson Elementary School, which serves kindergarten through fifth grade. They continue to Harborside Middle School and Joseph A. Foran High School. All three schools are a part of the Milford School District and have high ratings on Niche; Harborside Middle and Foran High have an A-minus, and Mathewson Elementary has a B-plus. Foran High serves about 790 students and has a student-teacher ratio of 12-to-1. They offer many clubs and organizations, including Fencing Club, Robotics Club and Crochet Club. Families interested in sending their kids to private school have multiple options, including Academy of Our Lady of Mercy Lauralton Hall, established in 1905 and boasts an A-plus on Niche. Interstate 95 runs along the neighborhood’s northern side and offers access to West Haven to the northeast and the New York state line to the southwest. Milford has a Metropolitan Transportation Authority (MTA) train station located off Railroad Avenue, and the Metro North line runs into Manhattan.

Those of a certain vintage will no doubt remember the “Choose Your Own Adventure” series of books. Young readers would get to the bottom of a page and decide which of a selection of next steps they wished to take, and would hurriedly turn to the page that corresponded to their choice, wondering what the result of their decision would be. In a sense, life in Milford mirrors that same concept. “Milford is popular because you can pick your lifestyle,” says Gianni Viscuso, a lifelong resident of Milford and Realtor with RE/MAX Right Choice. “You can live on the beach or on rural farmland. And no matter where you are, you’re never more than a few miles from downtown.” In the Parkway/Wheelers Farm Road neighborhood in the city’s northwestern section, residents live in the more rural area of town. Residents here are an active group, and easy access to the Housatonic is one of the primary draws of life in Parkway/Wheelers Farm Road. A public boat ramp at the Moses Wheeler Bridge allows for easy launching of trailed boats – and the on-site parking lot has spaces designed for vehicles with attached trailers – or the Valley Yacht Club offers slips for members who prefer to keep their boats in the water when not in use. Bluefish, stripers and other saltwater species are often caught in the brackish river water, as are freshwater bass, pike and trout. Where the river meets Long Island Sound and only accessible by boat is the Charles E. Wheeler Wildlife Management Area, a prime spot for birdwatchers looking to catch a glimpse of migratory birds. The area also offers superb fishing and waterfowl hunting opportunities. For those who prefer to stay on dry land, Solomon Woods covers approximately 100 acres and features multiple trails that wind their way through the park. Eisenhower Park is popular with families here, who love the park’s multiple trails, courts for tennis and pickleball, splash pad, soccer fields and picnic areas. But the real highlight of Eisenhower Park is Bodie’s Place Playground, named in honor of a young Milford resident named John Vaccino, whose family calls him Bodie. John has cerebral palsy, and he wanted to create a playground for children of all ability levels. The accessible playground at Eisenhower Park is the realization of that goal. And park-goers with four-legged family members can take the trail from Eisenhower Park to the Eisenhower Dog Park, an enclosed park with plenty of open space for playing and a creek for cooling off. Golfers can tee-off at Great River Golf Club, which offers members a challenging 18-hole course that is consistently ranked as one of the best courses in the state. Of course, this is Connecticut, so winter’s temperatures can send people inside. Fortunately for Parkway/Wheelers Farm Road residents, the Milford Ice Pavilion is located in the neighborhood, so they can ice skate or play hockey to stay active until things begin to warm up again. When they’re not busy with any of those activities, residents can often be found engaging in another of the neighborhood’s favorite pastimes: celebrating. Milford’s downtown sector is definitely a hotspot for events throughout the year. “That’s where the big events are,” says Viscuso. “We have the Oyster Fest with big name bands, Summer Lobster Bake and a tree lighting at Christmas, and the parade for St. Patrick’s Day is huge.” Another feature of Parkway/Wheelers Farm Road that attracts residents is the lower price points for homes in the neighborhood; the median price here is $510,000, and buyers pay an average of $295 per square foot. While those amounts are higher than the state as a whole, they are significantly lower than what one would expect to pay in Fairfield, less than 15 miles away, where the median price exceeds $1 million. Most of the area comprises single-family homes ranging in price from $270,000 for a four-bedroom/two-bathroom Cape Cod to $950,000 for a five-bedroom/three-bathroom colonial-style home. Homebuyers can also find two-bedroom condos in the low to mid-$400,000s at Caswell Cove Marina, a “dockominium” where residents can access the complex’s private marina and boat slips. Milford School District receives an overall rating of A from Niche. John F. Kennedy Elementary earns a B-plus, and both Harborside Middle and Jonathan Law High School earn an A-minus. Students at Jonathan Law High School can participate with over 30 different school-sponsored clubs, and they have the opportunity to play more than 80 varsity-level sports. There are also several excellent private schools in the area, including nearby Choate Rosemary Hall, rated the best private school in Connecticut by Niche, which gives it an A-plus. For fresh produce, River Crest Farm is a family-run organic farm focus on sustainability. They offer fresh produce and flowers, as well as vegetable plants and Christmas trees. For more comprehensive grocery shopping, Big Y World Class Market and ALDI are just across I-95, and Whole Foods Market, Trader Joe’s and Costco are located a few miles away on Boston Post Road. For home necessities and other shopping, Walmart – along with a host of other retailers – is also located up Boston Post Road. For those nights when cooking at home just won’t cut it, Monty’s River Grille, located in the Great River Golf Club, is a popular destination. The restaurant is open to members and non-members of the club alike, and offers a menu featuring influences from around the globe. For more casual fare, the pizza at Colony Grill Pizza is a crowd favorite in these parts because, as Viscuso says, "This is New Haven County, after all!" While not quite the bedroom community of commuters as towns found further south along the Connecticut coast, Parkway/Wheelers Farm Road does have its fair share of folks who make the daily trip to Manhattan by train. “Milford is a nice transportation hub with a train station. You can be at Grand Central Station in 90 minutes,” says Viscuso. The neighborhood offers easy access to surrounding amenities, health care and services thanks to its proximity to I-95 and major freeways.

Located in the southwest Connecticut city of Milford, Post Road North is home to a sprawling shopping district that offers the ultimate in modern convenience. Away from the stores stretched along the Interstate 95 and U.S. Route 1 corridors, residents enjoy an almost rural landscape populated by homes on spacious lots. “What’s so great about North Milford is that feels like you’re living in the woods, but you’re just minutes from shopping and restaurants; it’s the best of both worlds,” says Maura Cannon of Cannon Real Estate Services, who has lived in Milford for most of her life and has been selling homes there for 35 years. “Milford is just a great place to live. It’s got parks, beaches and a really nice historic downtown. It’s also a very convenient location with access to the interstate and Merritt Parkway, which takes you all the way into New York.” A collection of major retailers in Post Road North carries everything from groceries to home goods, pet supplies, clothing and more. Residents can choose between Walmart, Stop & Shop, Whole Foods and Costco when they need groceries. For a fun afternoon out, they often head to Connecticut Post Mall to shop at stores like Macy’s and Dick’s Sporting Goods, eat at popular chain restaurants like Buffalo Wild Wings or catch the latest movie at the theater. Other shopping centers across the neighborhood offer stores like Old Navy, Barnes & Noble, Michael’s and Sephora. While they’re out, locals can stop at MoMo Sushi, a popular local spot serving Japanese fusion among Post Road North’s many chain restaurants. Downtown Milford offers more unique dining options just 2 miles away, including Founders House Pub & Patio and Trattoria 'A Vucchella. The city’s commuter rail station is located in Downtown Milford. “From North Milford, you’re about four to six minutes away,” Cannon says. “The train can take you right into New York City.” Interstate 95 and U.S. Route 1, which both run through the neighborhood, provide easy access to nearby points of interest. Route 1 is especially convenient for travel throughout the area, while I-95 connects directly to Downtown New Haven, home of Yale University, only 10 miles to the north. State Route 15, also known as the Merritt Parkway, is located just west of the neighborhood. Designated as a National Scenic Byway, it’s one of the oldest parkways in the country. In addition to smaller neighborhood gatherings, residents are never far from events held in Milford itself, such as a summer concert series where locals listen to live music at Fowler Field just 2 miles from the neighborhood. Just to the west of the neighborhood, recreational opportunities abound at Eisenhower Park. “The park has been around for a long time, and it’s beautiful,” Cannon says. Children enjoy its waterpark and playground, tennis and pickleball courts provide space for friendly competition and trails offer the chance to explore the woods on foot or via bike. There’s even a dog park. For those who like to get their hands dirty, the nearby City of Milford Community Gardens is a favorite spot. “If you live in a condo, you can take one of the spaces and have your very own garden,” Cannon says. Golfers hone their game at the 9-hole course next to the park. Milford Green downtown is the second-oldest town green in New England, with a history that stretches back to the middle of the 17th century. The picturesque space is flush with flowers and dotted by historic monuments. Communitywide events and celebrations are held there year-round. Waterfront recreation is available only a few miles away, as Long Island Sound is a popular destination for beachgoers. Post Road North’s sidewalk-lined and tree-dotted streets feature large ranch-style homes with attached garages and split-levels with similar features sitting alongside Cape Cods with charming dormers and a variety of colonial-style homes, including Colonial Revivals. “Homes in North Milford have larger lots and are a little more expensive than other areas of the city,” Cannon says. “There’s something for everybody.” Prices typically range from $300,000 to $800,000. Condominiums starting at $200,000 and manufactured homes starting at $80,000 offer alternative options. With low inventory, though, competition for homes has been up. “Right now, we only have 56 homes, that’s homes and condos, for sale in Milford,” Cannon says. “Typically, we have 250, so it’s really down.” Children can attend Orange Avenue Elementary, which as a B-plus on Niche, Harborside Middle School, which has an A-minus, and Joseph A. Foran High School. With an A-minus, students at Foran High can participate in extracurriculars like fencing, American Sign Language and robotics clubs. Alternatively, The Foundation High School is a private institution that serves older students with special needs. A campus dedicated to younger students is in neighboring Orange.

It’s often been said that buying a home means buying a neighborhood. The Woodmont neighborhood takes it one step further, though. Buying a home in Woodmont means buying a way of life. “Woodmont is a lifestyle,” says Realtor and Connecticut native Robin Jossen. “There’s very much a beach vibe in the neighborhood. It’s very laid-back and casual. I know a lot of people who are downsizing from their homes in Westport to move to that area because they want that slower pace of life and more casual lifestyle.” That lifestyle – which Jossen describes as “coastal sophistication with a casual twist” – comes about as a result of the neighborhood’s location on Long Island Sound. That proximity to the water is, according to Jossen, the primary draw that brings people to Woodmont. “It’s people who love the beach,” she says. “It’s people who want that coastal lifestyle.” The coastal lifestyle of Woodmont focuses on the miles of pristine beaches that serve as the neighborhood’s eastern border. Whether it’s on Woodmont Beach, Spencer Street Beach, Morningside Beach or any of the other spots along the sound, residents here never have to look far to find a stretch of sand where they can relax and unwind. Adjacent to Woodmont Beach, residents will find a community park with a playground, a basketball court and a large open field for working off extra energy. The park is also the site of Woodmont Day, an annual celebration to welcome the summer season. The event kicks off with 5K run around the borough, and the fun continues with a parade and a full schedule of games, food and music. Woodmont residents mark the date every year on their calendars, as they look forward to getting together with friends and neighbors to sit in lawn chairs, eat burgers and fries and enjoy live music, as well as each other's company. Pickleball players can get in the kitchen on the courts at Howard Park, which also offers access to a playground. Tennis players need not feel left out, as the neighborhood has four courts available for public use at the Anderson Avenue Tennis Courts. Golfers will have to travel a little further, but only about 5 miles to Orchards Golf Course, a nine-hole course complete with a pro shop. Homes in Woodmont tend to reflect the sense of coastal sophistication that Jossen references. The neighborhood offers a quintessential New England vista, with a variety of architectural styles that include Cape Cods, cottages and farmhouse-style homes, along with more contemporary builds. One element that is uniform throughout the neighborhood is the care residents show in landscaping. Short, well-maintained grass is the norm, and many residents decorate their front yards with colorful shrubbery and crisp hedgerows. The median home price here is around $505,000, and buyers should expect to pay an average of $349 per square foot. Buyers can choose from condominiums that range in price from $150,000 for a one-bedroom/one-bathroom unit to $600,000 for a two-bedroom/two-bathroom penthouse unit with ocean views. Single-family home prices start at $250,000 for a two-bedroom/one-bathroom ranch-style and go up to $2 million for a four-bedroom/four-bathroom new construction home that looks out on Long Island Sound. “It’s a very family-friendly neighborhood that is a very tight-knit community,” says Jossen. “At the same time, empty-nesters love it, too, because it’s a peaceful area that’s close to the beach. And it’s more affordable than a lot of other towns along the coast.” Those interested in buying in Woodmont need to be aware that it is a borough of Milford, meaning the neighborhood provides municipal services for residents beyond what the city offers. As a result, there is an additional yearly tax assessment that residents must pay in addition to those paid to the city. Milford Public Schools earns an overall rating of A from Niche. Calf Pen Meadow School serves children through the fifth grade and earns a B-plus rating. East Shore Middle earns a B rating and Joseph A. Foran High School earns an A-minus. Students at Joseph A. Foran High School can join over 30 school-sponsored clubs, and they have the opportunity to play 25 different varsity-level sports. There are also multiple highly rated private schools in the area, including Hopkins School, which earns an A-plus grade from Niche. Stop & Shop, Target and Walmart are all located nearby, just across Interstate 95 from the neighborhood, so residents don’t have to travel far for groceries or other household necessities. In the same area is the Connecticut Post Mall for those times when the need for shopping requires attention. With retailers from Macy’s and Boscov’s to Rue21 and Zumiez, the Connecticut Post Mall has shoppers covered. The mall also features a Cinemark theater with 14 movie screens, Big Red’s Amusements for lovers of video games and even a lounge with couches, a big-screen TV and free Wi-Fi. When it’s time to dine out, Bonfire Grill is a casual, beachfront restaurant that serves a variety of sandwiches, burgers and seafood, and diners can choose to eat inside or on the outdoor patio. Locals swear by the lobster roll, with hand-picked lobster meat simmered in butter served on a New England roll. When the occasion calls for something a little more upscale, Village Bistro serves an eclectic assortment of European-inspired dishes and tapas, as well as a cocktail list that includes specialty drinks and an extensive wine list.