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Published by Contour Mortgage on August 03 2020

The Best Neighborhoods To Live In New Haven, CT

The charm of a small New England town combines with the cosmopolitan feel of a modern city in New Haven, CT. A seaside metropolitan area, the highly livable city features centuries-old architecture adorning houses, galleries, concert halls, and shops—all making New Haven the cultural capital of Connecticut. 

Of course, you can’t talk about New Haven without mentioning Yale University, the critical Ivy League institution that has attracted innovators, politicians, artists, and celebrities since it was founded in 1701. The university’s mere existence in New Haven means residents in and around the city have easy access to art, theater, college sports, and a diverse array of cuisine. 

In terms of walkable city centers, New Haven easily competes with Boston and New York City—and this is precisely why living in one of the nearby neighborhoods can be so strategic. You get all the benefits of the city, with the idyllic peace and quiet of suburbia. 

Here are the top 10 New Haven neighborhoods for families, based on research by Niche.com’s 

The Best Places To Live In New Haven.” We’ve also included local food tips to get a taste of what each town offers. But no matter where you live, be sure to trek over to one of the country’s very first burger joints, Louie’s Lunch, along with the area’s most famous pizzeria, Frank Pepe Pizzeria Napoletana, both in New Haven. 


1. Woodbridge

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Woodbridge School District $471,400 $1,220 $142,188 Alice Newton Memorial Park, Woodbridge Green Historic District About 18 minutes or around five miles

Incorporated in 1784, Woodbridge is an old fashioned town located in New Haven County. One of the top reasons to live here is the neighborhood’s location. Besides being only about 5 miles from New Haven, Woodbridge is approximately 80 miles east of New York City, 40 miles south of Hartford, and 130 miles southwest of Boston. The town is intersected by several major highways, and is also served by numerous transportation options including bus services and Amtrak and Metro-North, which both provide passenger rail services. Transportation and the proximity to major cities belies Woodbridge’s true charm, its quaint, small-town vibe and rolling green countryside. There’s an extensive network of hiking trails, along with safe neighborhoods, great schools, and lots of shopping, dining, and recreation to choose from. 

Local Food Tip: When it comes to local eats, three spots remain popular with residents: Woodbridge Social, Westville Seafood Drive In, and Thai Stories Restaurant



2. Chesire

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Chesire Public Schools $332,600 $1,242 $112,945 Quinnipiac Recreation Area, Cheshire Park, Cheshire Historic District About 25 minutes or around 13 miles

Called “the bedding plant capital of Connecticut,” Cheshire is definitely a garden-lover’s dream. Settled in 1694 as part of Wallingford, Cheshire boasts an estimated 400 million plants in 300 different varieties grown in town by about 30 farmers. In addition to its agricultural sector, the town has thousands of acres of open space and parks. This includes Quinnipiac Recreation Area, Mixville Recreation Area, and Lock 12 Historical Park. The former canal lock includes a gatekeeper's house, an arched railroad bridge and a blacksmith shop from the early 1800s. Despite economic growth over the last 40 years, Cheshire has maintained its rural character, thanks mainly to local preservation efforts. Commuters also have access to major hubs like New Haven and Hartford via an express bus and the Connecticut Transit New Haven line. 

Local Food Tip: Locals love two spots in particular for New Haven-style pizza and more: Viron Rondo Osteria and Cheshire Pizza & Ale.


3. Orange

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Orange Public Schools $389,800 $1,658 $117,215 Orange Historic District, Housatonic Overlook, Racebrook Tract About 18 minutes or less than 6 miles

Orange is one of the more historically minded towns in all of Connecticut. Incorporated in 1822, there are several locations within Orange that are on the National Register of Historic Places. The rural roots of this town are celebrated at the annual Orange County Fair and at the Orange Volunteer Fireman’s Carnival, both of which are held at the fairgrounds at High Plains Community Center near the center of town. What’s more, one town farm known as Field View Farm has been operated by the same family since 1639. Along with a rich history, Orange is also well learned. The town’s good public school district and large population of college-educated adults provide an environment conducive to academic values.

Local Food Tip: Searching for a great place to eat in and around Orange will likely lead you to the Bonfire Grill in Milford and local Orange restaurant Hook & Reel Cajun Seafood & Bar.


4. Guilford

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Guilford Public Schools $393,700 $1,424 $110,000 Bittner Park, Lake Quonnipaug, Westwoods Trails, Bishops Orchards About 20 minutes or about 12 milesWoodbridge

First settled by Europeans in 1639, Guilford has the third largest collection of historic homes in New England, with important buildings from the 17th, 18th, and 19th centuries. Life in Guilford seems to center around the Guilford Green, where events including the Guildford Craft Fair are held throughout the year. Specialty shops dot the town and combine with the residential neighborhoods to elevate the small-town vibe of the greater Guilford area. Located along the Route 95 Corridor, there is easy access to Route 91 toward Hartford, as well as the Merritt Parkway toward Fairfield County and New York. As for the railroad, there’s also the Shoreline East Station in Guilford. 

Local Food Tip: Locals love the comforting warmth of Guilford Bistro & Grille Cafe, as well as the always fresh Guilford Lobster Pound, where the dockside view is unmatched. 


5. Middlebury

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Pomperaug Regional School District $344,800 $874 $108,977 Hop Brook Lake, Meadowview Park, Middlebury Recreation Area About 45 minutes or more than 18 miles

Incorporated in 1807, Middlebury is one of the less populous towns on this list of places to live near New Haven. The town’s history began with small industries such as blacksmithing, which laid the groundwork for Middlebury’s economic base, and was followed by textile mills and small factories. Small town values abound in Middlebury, as its relatively low population gives it the sleepy feeling that can be of great importance for homeowners of a certain mind. Middlebury maintains its rural mindset, but it also boasts access to major throughways for commuters who want to rest in the suburbs, but work in the city. 

Local Food Tip: Popular places include comfort food go-to Uncommon Grill in nearby Watertown, as well as the highly rated Mexican restaurant Señor Panchos in Middlebury.


6. Madison

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Madison Public Schools $423,300 $1,389 $104,754 Rockland Preserve Singletrack, Hammonasset Beach State Park, Surf Club Beach, East Wharf, West Wharf About 25 minutes or about 17 miles

Tucked away on the southeastern corner of New Haven County, Madison occupies a central location on Connecticut’s Long Island Sound shoreline. Presently named after the fourth president of the United States, Madison was first settled in 1641. The beach is a major draw in Madison, where locals love Hammonasset Beach State Park, the state’s longest public beach, as well as Surf Club Beach for its picnic area and kayak racks. Madison's center of town is the main area for businesses and the location of the town library, Madison Green Historic District, along with many boutiques and eateries. The Madison train station is served by the Shore Line East commuter railroad, with service to New Haven's Union Station to the west, facilitating connections to the MTA's Metro-North Railroad and to Amtrak's Northeast Regional and Acela Express services. 

Local Food Tip: For burgers, seafood, and ice cream, hit up the seaside M&J Beach Grille.

7. Westville

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Westville Public Schools $242,740 $1,500 $84,673 Edgewood Park, Upper Westville Community Park About 10 minutes or less than 3 miles

Westville’s sheer proximity to downtown New Haven keeps it on or near the top of the best places to live in the area. The town is the westernmost area of New Haven, about 2 miles west of the main Yale campus. As it’s somewhat a college town, there’s plenty of parks for hiking, running, and biking, as well as Yale athletic matches. Westville is anchored by Westville Village, the local shopping district with boutiques, dining, and a burgeoning artistic community. The area is served mainly by CT Transit buses, which make commuting a breeze. 

Local Food Tip: There’s no shortage of great eats in and around Westville, Kool Breeze Jamerican Cuisine, Westville Seafood Drive In, and Cilantro Fresh Mexican Grill


8. Dwight

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Hartford School District $119,681 $1,086 $30,648 West Rock Ridge State Park, Rainbow Park, Dwight Street Historic District About 6 minutes or less than 1 mile

Dwight is perhaps best known for the many young professionals that call the neighborhood home while working in downtown New Haven. Just beyond Yale’s central campus. Dwight is mainly residential and includes single and multi-family homes along with smaller scale apartment buildings. The town’s Howe Street is locally popular for its many dining destinations. Meanwhile, the Dwight Street Historic District is New Haven’s main historic district and includes most of Dwight as well as the northeast corner of the West River neighborhood. The district, built just after the War of 1812, began mainly as farmland, and includes many historically significant buildings. 

Local Food Tip: Dwight’s proximity to New Haven means there’s plenty to dine on, including Marco Polo Pizzeria & Italian Restaurant, Miya’s Sushi, and House of Naan Indian Kitchen and Bar


9. Woodmont

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Milford School District $348,300 $1,398 $92,344 Trubee Doolittle Park, Orchards Golf Course, Mountain Meadow, Woodmont Beach About 19 minutes or less than 7 miles

First created in 1893, Woodmont is a borough in the city of Milford in New Haven County. Situated on the south coast of Connecticut along the Long Island Sound, Woodmont is among the most picturesque places in the state. Woodmont Beach, which is technically in Milford, is quiet and clean with little in the way of luxury amenities, but plenty of opportunities for tranquility and breathtaking views. The Milford Transit District handles the majority of transportation in and around Woodmont, and the proximity to New Haven makes this seaside community a great place to retreat to after a day of work in the city. 

Local Food Tip: Most dining options in Woodmont come with a side of ocean view, including Dive Bar & Restaurant, Stowe’s Seafood, and Ola Restaurant


10. Milford

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Milford School District $307,300 $1,574 $89,778 Silver Sands State Park, Eisenhower Park, Milford Cultural Center About 17 minutes or about 9 miles

Milford is a coastal Connecticut city in New Haven County, situated between Bridgeport and downtown New Haven. The city was one of the earliest settlements in south central Connecticut, giving rise to several other towns that broke off and incorporated separately, including Woodbridge and Orange. The seaside location makes the ocean a valuable asset to the community and this is most evident during the annual Milford Oyster Festival. The more than 14 miles of shoreline facing the Long Island Sound gives Milford lots of leisure time by the seaside. As for transportation, I-95 and U.S. Route 1 passes through the southern part of the city, while the Milford Transit District provides in-town services to local attractions. 

Local Food Tip: Local favorites for Milford residents include Founders House Pub and Patio, along with Bar 3 Thirty Three, and Bin 100 Restaurant.

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