Since it’s about 40 miles, or an hour-long train ride, from New York City, Stamford tends to attract buyers looking for easy access to the city, though the scenic, coastal atmosphere is appealing too. “One of the cool things about Stamford is you can live in an area with a city vibe, a beach vibe or a bucolic, woodsy vibe with total privacy,” says Jonathan Makovsky, a Realtor with JMX Realty Group who’s lived in Stamford for decades.
Stamford is Connecticut’s largest city by area and second-most populous city, behind Bridgeport, with 137,500 residents. While commuters often head southwest to New York, Stamford has its own industry and employment opportunities. Dubbed “Wall Street North,” a large part of its economy stems from the finance and banking industries. The city is home to eight Fortune 500 companies, making it the largest financial district in the New York metro region outside NYC. Companies include Phillip Morris International, Pitney Bowes, Deloitte and Synchrony Financial. In addition to Fortune 500 companies, Vineyard Vines, Indeed.com, the World Wrestling Federation, and NBC Sports Group have also planted roots in Stamford.
Stamford’s thriving tech startup community fuels another part of its economy, and the city made significant strides in innovation in 2021 and 2022. The University of Connecticut-Stamford opened a Technology Incubation Program, Tip Digital, which has grown to 23 data science startups; GE Appliances announced a multimillion-dollar initiative, CoCREATE Stamford, to return small appliance manufacturing to the city; and Digital Currency Group, a leading cryptocurrency investor, relocated from NYC to Stamford in 2022. The city also boasts seven co-working and incubator spaces, and technology research giant Gartner is one of Stamford’s largest private-sector employers.
Residents enjoy walking along the Harbor Point Board Walk in Harbor Point.
Stamford is home to the WWE's production hub, a major employer in the community.
Pickleball America, located inside the Stamford Town Center, is a popular recreational spot.
Stamford is a vibrant Connecticut city filled with economic opportunities.
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Hiking, fishing, sailing and swimming in Stamford
Niche ranked Stamford the No. 11 best city for outdoor activities in the country. It's a hub of recreation, much of which centers around the dense forests in northern Stamford or the Atlantic coast. With 19 miles of pristine shoreline, scenic trails, and a variety of hot spots for fishing, boating and crabbing, Stamford’s coastal culture is rich and deep.
Connected by the Cummings Marina, Cummings Park and West Beach stretch 106 acres and have two sandy beaches around the Long Island Sound, complete with beach volleyball and ballfields. Cove Island Park is a popular 83-acre site with beaches, bluffs, nature paths and a wildlife sanctuary. Besides Cummings and Cove parks, the city has more than 35 other parks and recreational areas. The Mianus River Park is a nature reserve along the Greenwich/Stamford border with 390 acres of forest lands, pools and miles of trails. Boaters sail around Harbor Point, which is emerging as a top destination in the city for waterfront activities, restaurants and entertainment. The area is home to four marinas, each offering different amenities; residents can sail the Long Island Sound, take a free water taxi ride or join the Stamford Yacht Club or Freedom Boat Club. Kayaks and paddle boards are available for rent at the marinas.
During Connecticut’s cold, gray winters, residents depend on indoor spaces. The Chelsea Piers Athletic Club is a sprawling sports complex where members can use indoor hockey rinks, pools, soccer fields and basketball courts. Pickleball America, the largest pickleball facility in the country, opened its headquarters in Stamford in 2023.
Cummings Park in The Cove has a beautiful sandy beach.
Cove Island in Stamford offers scenic trails and stunning views of Long Island Sound.
Shippan locals can sail out of the many nearby marinas alongside the bustling city of Stamford.
Play ice hockey or pickleball at the massive Chelsea Piers complex in East Side Stamford.
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Entertainment and eclectic eats abound in Downtown Stamford
Downtown is Stamford’s vibrant core, where residents will find the city’s best restaurants, nightlife, locally owned shops and activities. While Stamford’s diverse cuisine spans from Italian to no-frills BBQ joints to fine dining seafood spots on the water, it's becoming a destination for pizza: There are more than 50 pizzerias across the city.
Stamford Center for the Arts, which houses Palace Theatre, opened in 1927 as a vaudeville house and now hosts world-renowned performers, off-Broadway musicals and the Connecticut Ballet. And movie lovers catch films at Avon Theatre, a historic landmark since 1939 known for showcasing the best in indie and art nouveau films.
Creativity shines downtown, from murals bringing life to city buildings to the annual outdoor sculpture exhibit featuring over 40 pieces from various artists. While Stamford Arts Center keeps the scene flourishing, residents can also enjoy New England art at Stamford Museum and Nature Center. The museum features a collection by Gutzon Borglum, sculptor of Mount Rushmore, along with a 10-acre working farm and outdoor sculptures by artists from all over the world. The 91-acre Bartlett Arboretum and Gardens provides a scenic educational experience with stunning botanical gardens and 850 plant species from around the world.
“Alive At Five,” an annual summer concert series in Columbus Park, is one of the city's most popular events and hosts some of the music industry’s biggest acts. The city’s Thanksgiving Day Parade boasts one of the largest helium balloon parades in the country and attracts over 100,000 people annually.
Summer Street in Downtown Stamford offers a great variety of restaurants for every occasion.
Check out the Palace Theater in Downtown Stamford for an amazing line-up of shows.
Serenity is found all around the Stamford Nature Center near Turn of the River.
A dance company, the Stamford Police, and Elmo and his fishy were the climax of the parade.
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From coastal Cape Cods to high-rise condos
Stamford’s commutable location made it especially popular with New Yorkers relocating in 2020. “Just before Covid, we were seeing some millennials who were ‘never moving to the suburbs’ start to move here from apartments in New York City,” Makovsky says. “But then, in March 2020, the market was just absolutely on fire.” He says that the average price for a single-family home in early 2020 was about $575,000, and it’s $855,000 in October 2024, which is a 49% increase. The market has calmed down, with houses lasting an average of 42 days on the market, but inventory is still fairly low.
Downtown Stamford offers mostly upscale high-rise condos with a median sale price of $465,000, but condos can go for up to $2 million. Here, residents are steps away from nightlife, trendy restaurants and major employers. Neighborhoods like Springdale and Glenbrook are a couple of miles from downtown but have more of a suburban vibe, where Cape Cods and Colonial Revivals sit on tree-lined streets and cost around $500,000. Shippan is a coastal neighborhood where sand beaches line both sides of the peninsula, creating Shippan Point. Shingled waterfront homes and Capes often have access to private beaches via associations and usually cost at least $1 million. Despite the vast range of artistic, cultural and recreational experiences that Stamford offers, the proximity to New York plays a major role in housing prices. “If people are moving into a house in Stamford, at least one person in the household needs to get to New York for at least some of the week,” Makovsky says. "You can get much cheaper houses a little further north in Connecticut if you don’t need to consider commute times."
Glenbrook’s Cape Cods blend history with modern comfort.
Harbor Point combines high-rises with public green space.
Cambridge Court provides quiet seclusion with walkability to Downtown Stamford.
Shippan homes benefit from larger lots and brick walkways.
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Top-ranked public schools and higher ed
Stamford School District has 21 public schools, serves over 16,000 students, and has an overall B rating from Niche. The city also offers several private school options. Students wanting to stay close to home can attend Norwalk Community College or the University of Connecticut-Stamford in Downtown Stamford. Earning an overall B on Niche, UConn Stamford is ranked the No. 3 best-value college in the state.
Students at Dolan Middle School in Stamford benefit from diverse programs and activities.
Families in East Side Stamford benefit from strong school options, including Stamford High.
East Side Stamford offers access to Rogers International School, a B-rated charter option.
Study at the University of Connecticut, one of the top schools in the nation.
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A top transportation hub commutable to New York
Residents have convenient access to major highways Interstate 95, Merritt Parkway and Routes 1 and 137 to get around the city. I-95 gets residents to NYC in 40 miles, Newark in 50 miles and New Haven in 40 miles. Stamford is also a major hub along the Amtrak route, providing high-speed train service between Boston and Washington, D.C. The Stamford Transportation Center travels on Metro-North Railroad’s New Haven Line and is the second-busiest station after Grand Central Terminal. Commuter trains arrive in Stamford from all points between New London and New York, with the average commute being 47 minutes.
The closest airport is Westchester County Airport, an 8-mile drive from the city center. “It’s one of my favorite airports, because you just cruise in and out, and there are flights to a surprising number of destinations,” Makovksy says. LaGuardia Airport is the nearest international airport, located 26 miles away. CT Transit provides bus services to residents running along major arterial roads, and residents can hop on the Harbor Point Trolley to get around town or commute to work. A free service with 14 stops, the trolley makes a 30-minute loop around the city and stops at major destinations like UCONN Stamford and the Ferguson Library, the largest library in the state.
Decreasing crime levels and flood mitigation techniques
Violent crime in the area has been declining since 2016. According to the Stamford Police Department, violent crimes were down 1.5% in 2022 from the prior year, when 268 crimes were reported. Property crimes were also down in 2022, with a 9% decrease from the previous year. While both property and violent crimes were down for the city overall, both violent and property crimes were higher than the state for the same year. Violent crime was 43% higher than Connecticut’s in 2022, and property crimes were 7% higher.
Some waterside areas in Stamford are at risk of flooding, though many houses on the coast sit high enough up from the water that they’re out of the flood zone. Stamford Harbor has a hurricane barrier that mitigates the effects of flooding from extreme coastal storms.
Developments coming to Stamford
Stamford has focused on funding and creating initiatives in three major areas for the near future: technology, transportation and business development. Being a key transit hub for the Northwest Corridor, the nation's most densely populated region, Stamford has plans for its future in rail service. The city rolled out a master plan for the Stamford Transportation Center in 2022, aiming to make the busy complex a best-in-class facility. Part of that includes a new $82 million parking garage and other improvements to Station Place. Receiving $2.5 million in 2023 from the Connecticut Department of Transportation, the city also plans to develop an on-demand transportation service similar to ridesharing apps like Uber. The program is expected to increase access to public transit for 64,000 residents in lower-income neighborhoods and in communities farther away from public transportation.
Stamford has also rolled out the “Vision Zero Program,” a citywide effort to eliminate fatal and serious traffic crashes by 2032. In 2023, the city announced that part of this plan included a $1.23 million restoration to citywide traffic signals, $1.5 million for roadway design and reconstruction and $1 million toward bicycle and pedestrian infrastructure projects.
In 2023, the city broke ground on a new planetarium and astronomy center. The former Stamford Observatory & Museum, which included a historic 22-inch telescope, was torn down to pave the way for a new 11,000 square-foot, $12.5 million science destination slated to open in late 2024. The new facility will include a planetarium, lunar and solar telescopes and state-of-the-art technology.
Kevin E. O'Brien is the founder and broker of OBrien Premier Properties, LLC, a full-service residential and commercial brokerage in Fairfield County, Connecticut.
Kevin’s real estate experience began as a surveyor in 1977, where he spent over 20 years working with builders and developers. In 2000, Kevin started O’Brien Design a Land Use Planning and Design Company specializing in house plans, permits, zoning boards of appeals, inland wetlands, and planning and zoning work. Kevin joined Wilton Country Homes in 2004 as a real estate agent.
As a 40-year Wilton, CT resident and father of three sons (Sean, Casey, and Glenn), Kevin is an active member of the community, coaching his children in soccer, football, basketball, and baseball. Kevin is a former board member and past president of both the Wilton Little League and the Wilton Baseball & Softball Association.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
