Stamford

Late 19th-century Italianate-style storefronts mix with 21st-century high-rises in Downtown Stamford, the vibrant core of Connecticut’s second most populous city. “It’s the perfect mix of small-town and big city,” says Todd Auslander, a co-founder of The Auslander Kasindorf Team at Keller Williams Realty, who has sold several properties in the area. “There’s something to do every day of the week, whether you want to see live music at a bar or hang out at one of the little pocket parks.” Outdoor dining spaces block off parking spots along Bedford Street’s small strip of cozy bars and swanky Italian restaurants. Recently built condo complexes and century-old churches tower over the same streets. A neon red-and-blue sign glows atop the 1939 Avon Theatre, one of the neighborhood's many longstanding entertainment centers. The half-mile-long Greenway North Path connects Mill River Park, home of the Alive at Five summer concert series, with 48-acre Scalzi Park, the city’s largest green space. Locals also easily access the Stamford Amtrak Station and Interstate 95, also known as the Connecticut Turnpike, in Downtown Stamford’s southern edge. “There are restaurants and bars on almost every street in Downtown Stamford, but Bedford Street is probably the busiest because people can eat outside and walk somewhere else to get drinks,” Auslander says. Lime-green umbrellas shade bistro tables in front of Capriccio Café, a contemporary Italian spot known for thin-crust pizzas and Saturday-morning brunch. Next door, a stone fireplace crackles inside Tigín Irish Pub, where locals have gathered to watch soccer games, sip pints of Guinness and listen to live music since 1997. Bumper stickers, beer signs and dart boards cover the mahogany walls of Brick House, another late-night locale with different drink deals every night and weekend karaoke. Escalators and marble elevators connect Stamford Town Center’s four floors of shopping, home to retailers like Macy’s and Barnes & Noble. Though many stores closed post-COVID, the mall’s former Saks Fifth Avenue converted into the 27-court Pickleball America complex in 2023, slowly ushering in new restaurants and indoor playgrounds. Locals can grab groceries from Target on Broad Street. Downtown Stamford is also home to several large companies, like Deloitte and Henkel, as well as a more colorful corporate citizen. On Washington Boulevard, a 7-foot-tall concrete world championship belt sits outside the 13-story headquarters for World Wrestling Entertainment, which employs over 700 people. Young American elm trees, vintage lampposts, and condo and townhouse complexes fill Downtown Stamford’s sidewalk-lined streets. Renovated red-brick buildings from the 1920s have one-bedroom units selling between $250,000 and $400,000. Two-bedroom New Traditional townhouses built during the ’80s are priced between $500,000 and $600,000. Stamford’s tallest building, the 36-story Park Tower, was built in 2009, featuring floor-to-ceiling windows with Long Island Sound views. One-bedroom units can start at $700,000, and three-bedroom options may go for over $1.5 million. As the neighborhood is 80% renters, there are also several apartment complexes, like Atlantic Station, a mirrored, tri-tower building where rent costs between $2,800 and $4,000 per month. Light-pink cherry trees and black metal benches line the gray stone sidewalks of Mill River Park, a green space at the Rippowam River’s shallow, southernmost end. “This is a park that everyone in the city comes to,” Auslander says. “Kids will run around the water fountain in the summer, and then it becomes an ice-skating rink in the winter, so there’s stuff to do year-round.” Hand-carved horses, rabbits and frogs spin around a carousel, located under a curved wood pavilion. Dogs jump through tire obstacles at the gravel terrain Bark Park. Bright yellow marsh marigolds and purple New England asters are just a few native plants near the river’s rocky shore. Whittingham Discovery Center is a contemporary-style glass and stainless-steel building with exhibits on the history of the Mill River and Connecticut wildlife. For three Thursdays at the end of the summer, a stage at the park hosts the Alive at Five concert series, welcoming local beer tents, food trucks and live music from performers like Lil Jon and The All-American Rejects. Locals can follow the Greenway North Path to Scalzi Park, which brims with tennis, basketball, and sand volleyball courts. A spray park is next to the playground, where the equipment includes plastic rock-climbing walls and twisty slides. The crack of a bat and cheers from the crowd fill the air at the softball fields and Cubeta Stadium, the flagship facility for the Babe Ruth Baseball youth league. The closest Long Island Sound beach is 2 miles east at Cove Island Park. With pocket parks, historic churches and a handful of theaters, Downtown Stamford has numerous community hubs. An American flag waves over the grass and concrete Veterans Park, where the Downtown Stamford Farmers Market happens on Saturday mornings from June through October. Yellow, red and orange picnic tables dot Latham Park, a half-acre green space that hosts chess tournaments every Saturday morning. Both on Atlantic Avenue, The Palace is a renovated 1920s vaudeville theater for comedy shows, musicals and ballets, while Stamford Studios is an NBC-owned production center where programs like "Jerry Springer" and "Maury" used to film and where shows like “Karamo” and “Someone They Knew With Tamron Hall” now produce episodes. Movie buffs can catch indie flicks at the Greek Revival-style Avon Theatre or watch a blockbuster at one of the two AMC theaters. Built in 1868, the Basilica of Saint John the Evangelist is a Catholic, Romanesque Revival-style church on Atlantic Street, offering English, French, Latin and Creole services every Sunday. On Bedford Street, 56 bells chime atop First Presbyterian Church, nicknamed “Fish Church” for its circa-1954 wooden structure that resembles a fish. Children can attend Davenport Ridge Elementary School, rated a B-minus by Niche, and then Rippowam Middle School, which earns a C-plus. Students may continue to B-graded Stamford High School, where dual-enrollment classes with the University of Connecticut include environmental science, European history and microeconomics. The UConn Stamford Campus is an all-glass, 225,000-square-foot building in Downtown Stamford, where students can choose between 15 bachelor's degree programs, like financial management and political science. “People walk to work in Downtown Stamford, but there are a ton of New York City commuters too because it’s obviously a lot cheaper to live here,” Auslander says. The Stamford Amtrak Station on Washington Boulevard follows the Metro-North Railroad, carrying passengers to New York City in about an hour. The Connecticut Turnpike makes New York City a 40-mile drive south, and New Haven is equidistant to the north. Numerous Connecticut Transit bus stops are in the area. Stamford Hospital is about a mile west, and the Westchester County Airport is 13 miles northeast.

The East Side of Stamford combines quiet residential streets with small industrial pockets and walkability to the Long Island Sound shore. A wooden bridge stretches across nearby Cove Island Park's eastern and western regions, connecting its two beaches. “Walkability to this beach is a huge selling point,” says Meera Banta, a Realtor with Better Homes and Gardens Real Estate, who has sold several homes in the area. “You’re just minutes away from the water without paying for a waterfront house.” Ice hockey games and pickleball matches happen at the Chelsea Piers, a 465,000-square-foot dark blue recreation complex on Blachley Road that also has a fitness center. Car repair shops and Latin restaurants line Main Street, the neighborhood’s core road adjacent to the Connecticut Turnpike. Storage facilities and warehouses stretch alongside Metro-North Railroad tracks in East Side’s western region. Residents can also reach big-box retailers and Italianate-style restaurants in downtown Stamford, only 2 miles away. Single-family houses on East Side’s sidewalk-lined streets were developed between the 1920s and ‘60s. Gravel driveways stretch alongside two-bedroom bungalows. Stone walls surround Dutch Colonial Revivals on grassy 10,000-square-foot lots. Ornamental shrubs and red maple trees sit in front of three-bedroom Minimal Traditional cottages. “More and more renovated houses are hitting the market in East Side,” says Banta. “People are starting to invest in these properties because of how close they are to the beach.” Though the neighborhood is 60% renters, homes typically cost between $250,000 to $650,000, a range lower than a Stamford home’s average $700,000 selling price. Condo complexes are typically red-brick buildings from the 1970s and ‘80s. The Kingswood complex has two-bedroom units starting at $200,000, while the Glenbrook complex has New Traditional options selling for $400,000. Cove Island Park is less than a mile from East Side. In the park’s western region on the mainland, great egrets fly over the Cove Island Wildlife Sanctuary, where pink milkweed plants attract monarch butterflies, and Stamford’s only sand dunes overlook the Long Island Sound. Rollerbladers and bike riders glide across the sidewalk system, offering views of the center console and fishing boats parked at Cove Island Marina’s wooden docks. Umbrellas and foldable chairs dot the sandy shoreline in the eastern section of Cove Island Park. Rocky shoreline surrounds the SoudWaters Coastal Education Center, an aquarium and kayak rental hub. Costing $27 per car, a season pass is required to enter any Stamford beach. Children can attend Julia A. Stark Elementary, which has a B-minus grade from Niche, and Dolan Middle School, earning a C-plus. They may continue to B-rated Stamford High School, where dual credit classes with the University of Connecticut include computer science, German and oceanography. Rogers International Baccalaureate School on Blachley Road is a kindergarten through eighth grade charter option with a B grade. Opened in 2014, Chelsea Piers Athletic Club offers personal training and facilities for over 20 sports. Single membership is $185 per month, while family membership is $350. “Most kids in Stamford will play at least one sport here. It’s the nicest recreation center in town,” Banta says. Locals learn to swim in the Olympic-sized swimming pool, which also hosts competitive swim meets. Curtains separate courts in the basketball complex during youth games, while the turf soccer fields host adult leagues. Kids balance on high beams in the gymnastics studio, scale the plastic rock-climbing wall and bounce in the trampoline park. NBC Sports Group employs over 700 people in its 180,000-square-foot, all-glass office building next to the recreation center. On Courtland Avenue, wooden fencing encloses Stamford Dog Park, split into two sections for large and small dogs. Rope climbing structures, modern seesaws and a swing set sit atop beige rubber terrain at neighboring Stamford Playground. Tropical plants and brightly colored woven baskets decorate Brasitas, a Pueblo Revival-style restaurant known for Latin-fusion fare and handcrafted citrus cocktails. Across the street, Daddy’s Peruvian Deli is a counter-service spot that serves chicken, beef and pork straight off a fire-roasted spit. Numerous Mexican grocery stores are in the area, but ShopRite on Shippan Avenue is the closest big-box option. One of Stamford’s largest employers, World Wrestling Entertainment, has a beige TV Production warehouse on Hamilton Avenue. Young oak trees, pocket parks and black vintage lamp posts line nearby downtown Stamford, where residents will find more locally-owned restaurants, like Fish, a contemporary seafood spot with a greenery-covered patio. Stamford Town Center is an indoor mall also in the downtown area, anchored by stores like Macy’s and Barnes & Noble. Though residents can walk to the beach, East Side is a car-dependent community. The Connecticut Turnpike bisects the neighborhood, making New York City a 40-mile drive south and New Haven equidistant to the south. Stamford’s commuter rail station is barely a mile away, offering stops across Connecticut and New York. Numerous Connecticut Transit bus stops are in the area. The Stamford Hospital 3 miles south, and the Westchester County Airport is about 19 miles northwest of East Side.

Development in Glenbrook first began when the railroad from Stamford to New Canaan built the first station on the line in the neighborhood, and the area’s convenient train station continues to be a popular asset. “It’s a very convenient residential area that’s close to everything: downtown, beaches, and the Metro-North line at the Glenbrook station,” says Todd Auslander, partner at the Auslander Kasindorf Team at Keller Williams Prestige Properties who has served the area for 23 years. Glenbrook’s active neighborhood association encourages connection, while a wide array of restaurants and parks are close by in the diverse southeastern Stamford neighborhood. A mixture of condos and single-family homes sit close together on quiet residential streets. “Single-family homes are in the $500 to $600,000 range, which is affordable for Stamford. In most places around here, you can’t get into a single-family for under a high $400,000, and that’s for a home that will need some work,” Auslander says. He adds that the area’s would-be starter homes aren’t going on the market, as buyers who secured low interest rates aren’t selling, resulting in low housing inventory. He adds, “Any time I put a listing on the market, pretty much the first thing I’ll hear from buyers’ agents is ‘When are the best and final offers due?’ since we all know there’s going to be multiple bids.” Condos, which were built between 1960 and 1985, run the gamut from brick high-rises to colonial townhouse styles. Prices start at around $240,000 and rise to around $400,000. Colonial Revivals and Cape Cods were built in the early to mid 1900s and cost between $700,000 and $950,000, while smaller single-family homes were built in the mid-to-late 1900s. These ranches and bi-level properties are usually priced between $500,000 and $600,000. The Glenbrook Neighborhood Association, which has an annual fee of $10 per resident, organizes community events. Neighbors meet to discuss improvement plans at the association’s quarterly meetings, which are held at the Grace Evangelical Free Church. Residents come together to freshen up their homes and community at the spring and fall cleanups, which include unwanted clothing recycling, food drives, a swap meet and street cleanups. The community also meets for more festive celebrations, like the annual holiday tree lighting in early December at Hope Street Park. Kids enter a toy raffle and take pictures with Santa as locals sip free hot chocolate topped with marshmallows. The Ukrainian Museum and Library of Stamford, which is housed in the St. Basil Seminary, has special programs and displays of Ukrainian art and literature to peruse. Though downtown is the most popular area to eat, Glenbrook has a convenient commercial corridor. “Hope Street runs right through Glenbrook, which is where you find restaurants, stores and gas stations,” Auslander says. Mornings can start with donuts and coffee from Donut Delight or fresh bagels with flavored cream cheese from Village Bagels. Cosechas is a Colombian restaurant popular for its empanadas, and residents can grab a late-night slice from Nick’s Pizza. The family-owned restaurant has been serving thin-crust pizza since 1969; the pizzeria also has an adjoining bar called Bacco, where locals sip beer and cocktails. There are a couple of grab-and-go convenience stores throughout Glenbrook, and the Grade A Market of Hope Street is a small market that stocks groceries and household essentials. To shop at a larger supermarket, residents can drive about a mile and a half west to Stop and Shop. Downtown’s shopping area, called Stamford Town Center, is also about a mile and a half southwest. Residents walk around the mall, which has popular retailers like Macy's and Barnes and Noble, or pop over to big box stores like Target and Burlington. A couple of pocket parks add green space to the city streets. Northrop Park has a small playground where younger kids can run around while older children can play catch on the baseball diamond or a pickup game on the basketball court. Hope Street Park and Daskam Park both are tiny green spaces positioned between converging streets, where residents can sit on shaded park benches. For a longer forested walk, residents can travel about 2 miles northeast to the Woodland Park Nature Preserve in Darien. The park’s shaded nature trails wind by streams and connect hikers to ponds where they can observe wildlife. Locals can also drive about 2 miles southeast to go to one of the most popular parks in Stamford; Cove Island has a paved loop for bike rides and plenty of sandy beaches to swim. Beachgoers must pay for a seasonal parking pass, but there are discounts for Stamford residents and steeper discounts for residents whose cars are registered in the city. Commuters headed toward New York City benefit from the neighborhood’s train station, which is within walking distance for many but also has a parking lot. The New Haven line on the Metro-North Railroad takes residents to Grand Central Station in about an hour and 15 minutes. To travel throughout Stamford, locals can walk to bus stops operated by CTtransit; Route 334 takes residents downtown in about 15 minutes. Popular thoroughfares like Interstate 95 and nearby Washington Boulevard provide easier commute options for drivers. The Stamford Hospital is just over 2 miles away from the neighborhood, offering residents quick access to medical care. Kids may begin at Julia A. Stark Elementary School, which has a B-minus rating from Niche, and progress to C-rated Dolan Middle School. Older students can attend Stamford High, which has a B rating. The high school offers a comprehensive English Language Learning program, which enrolls nearly 200 students who speak more than 20 languages. Students can also graduate with the Seal of Biliteracy on their diplomas by proving literacy in a language other than English on a language assessment.

Harbor Point is a distinct waterfront neighborhood in Stamford, Connecticut with an identity separate from the rest of the city. “One of the most unique aspects of Harbor Point is the contrast between summer and winter. We turn into a ‘windy city’ in the winter, but in the warmer months, the cold gusts become a pleasant summer breeze,” says Dario Torregiani, a Stamford local and leasing consultant for Building and Land Technology (BLT) in Harbor Point. Formerly an industrial area, its revitalization into a vibrant neighborhood inspires some to jest that it is New York’s sixth borough. Alongside ample local amenities, public transportation via trolley, and one of the most popular options, via train, makes for a quick commute into the rest of the city. The residential landscape is evolving, featuring luxury living spaces and retail areas, all with waterfront views. “Even though there are over 2,000 apartment units here and a million things going on, it is a very homey place,” Torregiani says. “Everyone gets to know each other here, and we have building-specific events that bring neighbors together into a tight-knit community.” Harbor Point’s parks are a key piece of the neighborhood’s identity and provide lively communal spaces. Kosciuszko Park sprawls over 18 acres along the waterfront, where locals can walk on trails or picnic at a pavilion, and children can play on the playgrounds. Commons Park is situated amidst the newly developed areas of shops and residential buildings and offers a green oasis amid urban surroundings. Harbor Point Boardwalk stretches over 2 miles along the water. Whether locals are enjoying a leisurely walk at sunset or going for a morning run, the Long Island Sound offers a striking backdrop. The boardwalk is also a popular spot for events and attractions, such as free yoga, swing sets and restaurants with outdoor waterfront seating. Slips are also available to dock boats at the Harbor Point Marinas. Harbor Point offers a diverse array of shopping and dining options that cater to a variety of tastes and preferences. Stamford Town Center, located within a mile of the neighborhood, offers popular retail options, such as Macy’s and Target, but Harbor Point also has its own unique shopping destinations. Harbor Point Organic Market is situated off Washington Boulevard for a curated selection of fresh produce, and other specialty markets are available within the neighborhood. Additionally, Whole Foods is about 5 miles away and ShopRite is down the road about 1 mile. Popular restaurants include The Wheel on the eastern side of the neighborhood, known for its brunch and dinner options with a waterfront view. Along the boardwalk, dining options range from casual cafes to authentic eateries. Sign of the Whale stands out as a gastropub with a rooftop patio, recognized for its craft cocktails and pub fare. MEXiCUE serves Mexican barbecue with an American Southern twist and seasonal cocktails. Harbor Point hosts a multitude of activities and events. Torregiani mentions building-specific events, where locals can partake in events right at home, such as wine and tea tastings and hot chocolate gatherings. Larger events, such as 5K runs and festive Christmas celebrations, also foster the close community atmosphere. During the warmer months, the neighborhood comes alive with farmers markets and the Harbor Point Art Festival. Other activities events include yoga classes and evening movie showings at Commons Park. With only about 15% of the population opting to own property, the majority of residents choose to rent, drawn by the convenience and amenities offered by the neighborhood’s apartment complexes. Nearly half of the housing market consists of apartments, with monthly studio rent typically ranging from $2,000 to $4,000, though luxury units command prices upwards of $8,000. Complexes often feature gyms, pools and community spaces for events, sitting by a firepit or shooting some pool. One-to-two-bedroom spaces in condominium units, typically in colonial or traditional architecture, can start around $200,000 and escalate over $1 million, influenced largely by location and proximity to the water. Students in Harbor Point attend schools outside of the neighborhood in Stamford Public Schools. Springdale Elementary is about 5 miles away and scores a B-minus on Niche. Students can then head 3 miles to Dolan Middle, which has a C-plus grade. Stamford High, about 2 miles away, earns a B and has been recognized as the No. 2 Standout High School in Connecticut by Niche. Stamford High sports teams have also won over 40 state championships, from football to basketball. For families looking for private schools, faith-based education is available, and Waterside is a primary option off Pacific Street. Though Harbor Point has seclusion from the rest of Stamford, there are convenient transportation options for those who work or venture out of the neighborhood. The train station is a sidewalk commute away, providing easy access to New York City and other nearby destinations. The neighborhood’s trolley system operates throughout the day, completing a 15-minute loop to the train station and downtown area. Torregiani says rush hour traffic, although present on nearby Interstate 95, does not significantly affect Harbor Point due to its strategic location and commuting patterns. Additionally, the neighborhood’s proximity to the water allows for unique transportation experiences, such as water taxis during the summer months. For air travel, the Westchester County Airport is about 16 miles away, though I-95 expedites travel time to about 20 minutes.

North Stamford is a popular option for homebuyers seeking a large lot of land in a calm area. The neighborhood includes proximity to Stamford Downtown’s sector of Connecticut’s Gold Coast about 7 miles away, and New York City is a little over 1 hour south. “If you crave peace and quiet, you will love North Stamford,” says Realtor Barbara Hickey with William Pitt Sotheby’s International Realty, with 22 years of experience in the area. Hickey mentions that zoning regulations prohibit large events, and retail and restaurants are limited in order to keep North Stamford as private as a “tranquil countryside.” Potential homebuyers often choose the area for its 1-out-of-10 CAP Index, making it one of the safest neighborhoods in the country. Its mix of green space, nearby schools and shopping and dining along Merritt Parkway/Route 15 provide residents with convenience in an area that is relatively secluded from busier urban spots. Home prices are on a wide spectrum, with most falling in the $800,000 to $1.5 million range. “The overwhelming majority of North Stamford is a minimum 1-acre zone, with some pockets being 2- and 3-acre minimums,” Hickey says. Two-bedroom homes on smaller lots are available, though, starting around $400,000, typically closer to Merritt Parkway. Four-to-five-bedrooms with generous acreages are most common, with prices that range anywhere from $600,000 to over $8 million. Modern farmhouses and colonials are common in the area, though other classic styles with a contemporary twist are popular, as well. With little-to-no sidewalks on the streets, residents typically get around the neighborhood and into the city by car. Trails and parks are aplenty, though, so locals have ample opportunity to walk and hike nearby. North Stamford is home to plenty of open space to stay active. “North Stamford has many beautiful, abundant parks. There’s a Little League baseball field, other parks have playgrounds and picnic areas, and others have hiking trails. There’s something for everyone,” Hickey says. One popular attraction is Bartlett Arboretum and Gardens, which also features an education center and library. Next door to the arboretum sits Stamford Museum & Nature Center, which has different animals, such as otters, nature trails and rotating exhibitions. Hiking trails are available at various areas and nature preserves, including Mianus River State Park Scenic Reserve, Newton Mills Park, Colhoun and Birch Meadow. For those who enjoy fishing, North Stamford Reservoir is a popular spot to cast a line. Golfing is also available by membership nearby at Rockrimmon Country Club, The Stanwich Club and Pound Ridge Golf Club. Locals can head toward Merritt Parkway for everyday necessities and dining options, such as Trader Joes, ACME Markets and fast and casual spots, like Starbucks and Panera Bread. Due to zoning regulations, Hickey says, “North Stamford has just a sprinkling of restaurants.” Farmhouse at the Crossroads is an exception, as a community staple that was built in 1875. This popular restaurant is known for its fine dining, including dishes like arancini, branzino and crispy pork belly. LaRocca’s Country Market is another classic establishment, built in the early 1920s. The market has local items, prepared foods, fresh meat, produce and everyday grocery items. LaRocca also supports the community by donating to local causes and by catering events. Many families in North Stamford send their children to King School, which is a private institution for prekindergarten through Grade 12 that scores an impressive A-plus grade on Niche. King is about 5 to 6 miles from most residences. Public options are also available through Stamford Public Schools, beginning at Northeast Elementary. This primary school scores a B-minus rating and emphasizes college and career readiness at a young age, with organization and study skills classes beginning in Grade 3. Students can then head to Turn of River Middle, which scores a C-plus. Westhill High earns a B-plus and offers over 50 clubs and activities. Westhill also has a strong athletic program, and the boys tennis team won the Fairfield County Interscholastic Conference (FCIAC) for the first time since 1978 during their previous season. Though North Stamford consists primarily of residential streets and open outdoor space, amenities are still available close by. For example, places of worship, including churches of various denominations and a synagogue, sit within the neighborhood. Health care is also available at urgent care clinics and Optimus Health Care general hospital, about 6 miles away. Hickey summarizes transportation in the neighborhood by saying, “Many North Stamford roads are windy, where traffic has a tendency to move a bit slower. An Uber can be had throughout the area, but the municipal transit only has a few stops here.” For air travel, Westchester County Airport is about 12 miles away via Merritt Parkway.

Shippan is a peninsula in Stamford where residents enjoy access to private beaches and waterfront properties. A nearby industrial area with the city’s water treatment plant keeps home prices lower than nearby Greenwich or Darien, but the nearby grittiness isn’t an issue for residents. “Shippan has sand on all sides of the peninsula, which is rare. It’s very nautical—people love sailing and water sports,” says Charles Vinci, a Realtor with Compass Connecticut who operates an informational YouTube channel about real estate in southern Fairfield County. The community has an active neighborhood association, and most properties belong to full-time residents, though some seasonal homeowners are in the mix. With sand beaches on all sides of the peninsula, there are plenty of options for coastal recreation. “One of the coolest things about Shippan is that there are all these associations with private beaches, so you want to be on the lookout when searching for homes,” Vinci says. “The house might not have direct beach access, but it shares a little chunk of beach with 20 or 30 other houses.” If residents aren’t zoned to a private beach, they can head to the public West Beach, a small sand swimming beach with a playground. West Beach Park has soccer fields and baseball diamonds, and a mile east, Cummings Park has tennis and basketball courts and softball fields. Cummings Park also has a swimming beach where locals play beach volleyball and a fishing pier that extends into Westcott Cove. There are numerous marinas throughout the peninsula; boaters can dock at the Stamford Yacht Club, Harbor House Marina or the Safe Harbor Yacht Haven after sailing on the Long Island Sound. Residents can pay to join the Woodway Beach Club for a private beach, clubhouse and tennis courts; the club is associated with the Woodway Country Club in Darien, which has an 18-hole championship golf course. The Shippan Point Association, which is funded by annual dues of $30 per household, organizes seasonal events. The neighborhood welcomes spring with an Easter Bunny meet-and-greet and small kids’ parade. There’s also a Fourth of July parade, where children decked in their red, white and blue attire bike through the streets, anticipating the Independence Day ice cream social. The neighborhood’s largest event is Celebrate Shippan, which is held at Woodway Beach Club in October. Locals eat burgers and participate in contests and games, while bakers come with their best sweet treats to compete in the Great Shippan Bake-Off. A Thanksgiving Day turkey trot loops the peninsula, and neighbors usher in the holiday season with a tree and menorah lighting in December. Classic New England properties line the peninsula’s gridded streets, and some large waterfront properties are along Shippan’s perimeter. A few condo buildings from the 1980s are near the coast in the northwestern section of the neighborhood; these usually cost between $500,000 and $700,000. Smaller Colonial Revivals and Capes from the mid-20th century are priced between $630,000 and $750,000, but larger Colonial Revivals cost between $1 million and $2 million. Sprawling coastal colonials with garden landscaping cost anywhere between $2.3 million and $5.6 million. Shippan’s few restaurants sit mostly along the waterfront. Brennan's by the Beach is a laidback coastal eatery near West Beach that serves burgers, lobster rolls and cocktails. The Beer Garden at Shippan Landing is on the peninsula's western side. Locals head to the outdoor patio for evenings filled with craft beer, live music, cornhole games and food trucks. There are more dining options a mile north on Shippan Avenue, like Cafe Silvium, which serves pasta and other Italian dishes. The closest supermarket, ShopRite, sits along Shippan Avenue 2 miles north of the neighborhood. Residents can drive north to downtown Stamford for more dining options or to go retail shopping at stores like Target and Burlington. Children may begin at Toquam Magnet Elementary School and progress to Rippowam Middle School; both schools have C-plus ratings from Niche. Stamford High School, which has a B rating, serves older students. The high school offers a career and technical education program where students enroll in a family and consumer science pathway or a business program. The CTtransit bus stops along Shippan Avenue; residents can board Route 326 to link with Route 327 and be downtown in about 30 minutes. The Stamford train station is about 2 miles northwest. Commuters who work in New York City board Metro North’s New Haven line to Grand Central station; the journey takes about an hour and a half. Interstate 95 runs parallel to the train tracks near the Stamford train station, so residents can merge onto the highway to drive the 43 miles southwest to New York City. Traveling 43 miles northeast on the interstate takes drivers to New Haven. Vinci says that flooding and storm surges are always notable considerations for buyers looking at waterfront property, but Shippan’s coastal homes are distinct. “A lot of houses sit so high they’re usually out of the flood zone, even though they’re on the coast,” Vinci says. “There’s not an Armageddon that’s going to bring an issue to those ones.” As a result, most of Shippan’s homes have a minimal risk of flooding according to Risk Factor, though there are some homes that are closer to the water in the southern section of the neighborhood. According to Risk Factor, these can still have an extreme risk of flooding.