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Published by Contour Mortgage on December 16 2022

The Best Neighborhoods To Live In New Haven, Connecticut

Editor’s Note: This blog was originally published in August 2020 and has been revised to reflect industry statistics, trends, and updates.

The charm of a small New England town combined with the cosmopolitan feel of a modern city could best describe New Haven, Connecticut. A seaside metropolitan area, the state’s second-largest city features centuries-old architecture adorning houses, galleries, concert halls, and shops—all contributing to New Haven’s nickname “The Cultural Capital of Connecticut.” 

Of course, you can’t discuss New Haven without mentioning Yale University, the Ivy League institution graduating innovators, politicians, artists, and celebrities since its founding in 1701. The university’s New Haven location provides residents in and around the city easy access to art, theater, college sports, and a legacy of renowned academics. 

New Haven boasts a walkable city center easily comparable with Boston and New York City—and this is why living in one of the nearby neighborhoods can be so strategic. You get to experience all the perks of city living, along with the peace and quiet of suburbia! 

New Haven is also dubbed “The Elm City” because it was the first American city to incorporate a public elm tree planting program.

Here are the top 10 New Haven neighborhoods, based on research by Niche.com’s  “The Best Places To Live In New Haven.” We’ve also included local food tips for a taste of what each town offers. But regardless of where you reside, visit one of the country’s very first burger joints, Louie’s Lunch, along with the area’s most famous pizzeria, Frank Pepe Pizzeria Napoletana

Learn more about the top 10 places to live in New Haven, and each area’s best features and benefits.


1. Woodbridge

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Woodbridge School District $464,400 $1,375 $157,610 Savino Vineyards, Shepherd Farm About 18 minutes or Around Five Miles

Incorporated in 1784, Woodbridge is an old-fashioned, centrally located town in New Haven County. Just five miles from downtown 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 also served by bus and passenger rail services.

Transportation and proximity to major cities belie  Woodbridge’s true charm—its quaint, small-town vibe and rolling, green countryside. There’s an extensive hiking trail network, along with safe neighborhoods, great schools, and abundant shopping, dining, and recreation. 

Local Food Tips: Paolo Ristorante features local Italian flavor and signature cocktails. Visit Solun Tapas Restaurant Bar for small plates and traditional Mediterranean entrees. 


2. Cheshire

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Cheshire Public Schools $338,800 $1,336 $122,477 Mixville Recreation Area, Lock 12 Historical Park, Cheshire Historic District About 25 Minutes, or Around 13 Miles

Dubbed “The Bedding Plant Capital of Connecticut,” Cheshire is a garden-lover’s dream. Settled in 1694 as part of Wallingford, Cheshire boasts an estimated 400 million plants in 300 different varieties grown by about 30 local farmers. The town also has thousands of acres of open space and parks, including Quinnipiac Recreation Area, Mixville Recreation Area, and Lock 12 Historical Park. The former canal lock includes a gatekeeper's house, arched railroad bridge, and early 1800s blacksmith shop. 

Despite economic growth throughout the past 40 years, Cheshire has maintained its rural character thanks to local preservation efforts. Commuters also have access to New Haven and Hartford via an express bus and the Connecticut Transit New Haven line. 

Local Food Tips: As one of Connecticut's oldest Mexican family restaurants, Señor Pancho’s also boasts the state’s best burrito! 


3. Orange

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Orange Public Schools $391,500 $1,543 $129,489 Orange Historic District, PEZ Visitor Center About 18 Minutes, or Less Than Six Miles

Orange is one of the more historic towns throughout Connecticut. Incorporated in 1822, there are several locations designated on the National Register of Historic Places. Its rural roots are celebrated at the annual Orange County Fair and Orange Volunteer Fireman’s Carnival—both held near town center at High Plains Community Center Fairgrounds. 

Field View Farm has been operated by the same family since 1639! Orange is also home to several academic institutions, such as the University of New Haven Graduate School campus and Yale School of Nursing.

Local Food Tips: Searching for a great place to eat in and around Orange will likely lead you to Ola Restaurant for authentic Latin cuisine or Asian-inspired bistro Mai Thai.


4. Madison

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Madison Public Schools $424,000 $1,360 $119,777 Rockland Preserve Singletrack, Hammonasset Beach State Park, Meigs Point Nature Center 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. Named after the fourth president of the United States, Madison was first settled in 1641. Outdoor activities are a major draw, 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 town center contains many businesses, the public library, its Green Historic District, and plenty of 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 Amtrak's Northeast Regional and Acela Express services. 

Local Food Tips: Visit Bar Bouchée for a cozy, French-style bistro dinner. If you’re craving local comfort foods, check out Friends & Company for homemade soups, meatloaf, and mashed potatoes.


5. Guilford

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Guilford Public Schools $398,400 $1,523 $108,243 Bittner Park, Lake Quonnipaug, Westwoods Trails, Bishops Orchards, Hyland House About 20 minutes, or About 12 miles

First settled by Europeans in 1639, Guilford has the third-largest collection of historic New England homes from the 17th, 18th, and 19th centuries. Life here often centers around the Guilford Green, a beautiful open space where events including the Guildford Craft Fair are held year-round. Specialty shops dot the streets and combine with the residential neighborhoods to amplify its small-town vibe.

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. Train service includes Shoreline East Station in Guilford. 

Local Food Tips: Customers love the comforting warmth of Guilford Bistro & Grille Cafe. For locally sourced produce and seafood, check out South Lane Bistro in Guilford’s historic center.


6. Middlebury

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Pomperaug Regional School District $361,400 $1,000 $120,480 Hop Brook Lake, Quassy Amusement & Waterpark, Middlebury Recreation Area About 45 Minutes, or More Than 18 Miles

Incorporated in 1807, Middlebury is one of the least populous neighborhoods on this list. Its commercial history began with small industries such as blacksmithing, laying the groundwork for Middlebury’s economic base, and was followed by textile mills and small factories. Small-town values abound in Middlebury, and its relatively tiny population boasts a so-called “sleepy” vibe of great importance to particular homeowners. Middlebury maintains its rural mindset, but also features access to major throughways for commuters who want to live in the suburbs but work in the city. 

Local Food Tips: Take a trip to Vyne Restaurant & Bar for traditional American cuisine with Mediterranean flavors. If a local breakfast or brunch spot is more your speed, check out Kitchen 64


7. Downtown

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features
New Haven Public Schools $241,133 $1,527 $63,894 Lighthouse Point Park, Yale University, East Rock Park

Situated around the lush, 16-acre parkland of New Haven Green, Downtown New Haven boasts diverse eateries, renowned institutions of higher learning, museums, galleries, and other cultural attractions. With many restaurants, bars, and clubs throughout Chapel Street, the area also includes Yale University’s main campus and numerous art galleries. Downtown exists along streets throughout standalone sections within New Haven Green, such as Chapel Street, Broadway, Ninth Square, and Whitney Avenue.

New Haven’s housing expansion and population of more than 7,000 residents have brought additional revenue to local businesses. 

Local Food Tips: Across from the New Haven Green, Zinc offers a modern twist on classic dishes such as salmon, pork chops, and New York strip steak. For tapas and drinks, check out the rustic Barcelona Wine Bar.


8. Woodmont

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Milford Public Schools $379,200 $1,629 $87,361 Woodmont Beach, Robert Treat Farm About 21 Minutes, or 10 Miles

Founded in 1875 as a popular New England summer destination Woodmont is designated a borough within the City of Milford, and its seaside charm has dazzled generations of vacationers, inspiring many to remain year-round.

Woodmont Beach in nearby Milford is the only public spot to swim, kayak, and fish. It’s also a popular site to walk or jog while admiring historic homes perched above the shoreline. 

The borough’s stop along the Metro-North New Haven Line has commuters into New York City within 90 minutes. 

Robert Treat Farm holds a weekly farmer’s market during the spring and summer. One of the area’s main attractions is Woodmont Day held every July with a theme parade, 5K run, and other family-friendly activities.

Local Food Tips: Experience authentic Italian cuisine at Strega Milford, or visit Stonebridge Restaurant for local New England fare with a view of the Wepawaug River.


9. Milford

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
Milford School District $321,800 $1,608 $95,627 Silver Sands State Park, Eisenhower Park, Milford Cultural Center About 17 Minutes or About Nine Miles

Situated between Bridgeport and downtown New Haven, Milford is a coastal Connecticut city in New Haven County. It's also one of the earliest settlements in south- central Connecticut, giving rise to several other towns that incorporated separately, including Woodbridge and Orange. Its seaside location makes the ocean a valuable community asset, which is most evident during the annual Milford Oyster Festival. 

The more than 14 miles of shoreline on Long Island Sound creates many prime leisure spots for residents. As for transportation, I-95 and U.S. Route 1 pass through the southern part of the city, while the Milford Transit District provides in-town services to local attractions. 

Local Food Tips: Local favorites for Milford residents include The Corner Restaurant, Bistro Basque, and GG’s Wood Fired Pizza.


10. Westville

School District Median Home Value Median Rent Median Household Income Nearby Parks & Features Proximity to Downtown
New Haven Public Schools $278,251 $1,802 $97,064 Edgewood Park, Yale Peabody Museum About 13 Minutes or About Two Miles

Named for its proximity just west of downtown New Haven, Westville’s rich history and firm roots designated it a Historic District on the National Register of Historic Places in 2002. While this mixed-use hamlet is known for slightly above-average costs of living, Westville residents enjoy several benefits, including an above-average school system, easy downtown shopping district access, and seasonal activities.

With public art a community mainstay, its downtown area boasts several galleries and restaurants. It’s also known for happening brunch spots on weekends for locals and out-of-towners.  

One of the area’s biggest attractions is the Westville Village Renaissance Alliance, hosting several special events, such as the Halloween Puppet Parade, summer concert series, and holiday season activities. 

Local Food Tips: Featuring various local spots boasting diverse cuisines, we’ve narrowed it down to Rawa for Mediterranean fusion delights, and House of Chao for Pan-Asian specialties.


The Takeaway

If you’re considering a move to New Haven, it’s best to weigh all options, such as median home value, affordability, school districts, transportation, restaurants, and leisure activities. When working with loan officers at our Waterford, Connecticut branch, you’ll receive professional guidance on choosing the best financing for your dream home. 

Contact Contour Mortgage in Waterford, Connecticut to learn how we can help with loan financing requirements, qualifications, and questions. 

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