$2,357,216Average Value$756Average Price per Sq Ft22Homes For Sale
A high-end suburb with an involved community in Westport
Staples shares a name with Westport’s well-ranked public high school, which is one of the area's major draws. Niche gives both the high school and the district an A-plus grade, ranking it as the second-best district in the state. Staples High sits near the middle of the neighborhood, among peaceful streets filled with luxurious colonial-style homes. While much of life can revolve around students, the community extends beyond younger residents. “After their kids leave the school system, people will stay for their empty nesting years. They have longtime friends here, so it’s just a fabulous place to be an empty nester, too,” says Leslie Clarke, a Realtor with Compass Connecticut and established Westport resident. Staples is also centrally located in Westport, putting locals within 4 miles of the shopping in Westport Village and the recreation along the coast.
Large Colonial Revivals with neat landscaping
Peaceful, residential streets weave through the trees in Staples, often ending in cul-de-sacs. Homes sit on landscaped lawns encircled by stone retaining walls and short wooden fences. Older homes, like ranch-style houses and smaller Colonial Revivals from the early-to-mid 1900s, cost between $600,000 and $1 million. Large Colonial Revivals built within the last 20 years usually cost between $1.5 million and $3.5 million, but new, sprawling colonial-inspired estates can cost as much as $4.5 million.
Older houses in Staples cost between $600,000 and $1 million.
Ranch-style homes are a common type of houses in Staples.
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Staples High School is the best in Connecticut
All three of the schools that Staples students are zoned for are in the neighborhood. Kids can begin at Long Lots Elementary School, which has an A-plus rating from Niche. They may progress to Bedford Middle School, which earns an A grade. Staples High School, which Niche ranks as the best high school in the state, earns an A-plus. Students can apply to technical or magnet high schools in nearby cities, like the J.M. Wright Technical High School in Stamford or the Center for Global Studies in Norwalk, to enroll in specific career preparatory programs. Staples High School also offers courses in culinary arts, photography and graphic design.
Bedford Middle School in Westport is also highly rated, scoring an A from Niche.
Staples High School serves students in grades 9th through 12th and earns an A-plus from Niche.
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Ball fields, country clubs and nearby beaches
Little league and softball teams practice at the Town Farm Ball Complex, a public park with ball fields and pickleball courts. “A big draw to Westport is that all the children’s sports and recreational activities are town-wide,” Clarke says. “Even if they go to different elementary or middle schools, by the time they enter Staples, the kids know each other.” The neighborhood also has the Fairfield Country Hunt Club, a social and equestrian club with riding stables and experienced trainers. It frequently hosts horse shows, and members meet for matches on the tennis courts and lounge by the swimming pools. Along the coast, there’s the Westport Longshore Club, which has a public golf course, marina, swimming pool and tennis courts. Compo Beach and Sherwood Island State Park are both popular places to go swimming or explore the Long Island Sound's coast.
Youth sports teams practice at the Town Farm Ball Complex in Staples.
The equestrian Fairfield Country Hunt Club in Staples has riding stables and tennis courts.
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Local eateries on Post Road and retail stores close by
Post Road is lined with restaurants and businesses. In the morning, locals can grab breakfast from PopUp Bagels, which offers rotating flavors of different schmears. American classics, like omelets, pancakes and cheeseburgers, are served at Sherwood Diner, a comfortable, old-fashioned eatery. At Pizza Lyfe, diners order New York-style pies and Italian sandwiches. For groceries, Post Road has supermarkets like Trader Joe’s and Big Y Supermarket. The neighborhood is 2 miles from Westport’s walkable shopping district, which is built along the Saugatuck River. Residents peruse shops like Anthropologie, Lululemon, Gap, Vineyard Vines and J. Crew or head to the historic Westport Country Playhouse to attend plays or concerts.
Staples residents pick up groceries from Big Y Supermarket.
PopUp Bagel offers rotating flavors of different schmears in Staples.
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Events at the local high school and community gatherings downtown
The community often congregates at Staples High School, cheering on the Wreckers at football games or appreciating the high school band at the December candlelight concert. Westport Village, the neighborhood just east of Staples that hosts the shopping district, is a destination for larger town events. In the summer, free outdoor concerts are held at the riverside Levitt Pavilion. Holiday parades march down Main Street for Memorial Day and Halloween.
Cheering on the Wreckers at Staples High School football games is a popular activity in Staples.
Free outdoor concerts are held at the riverside Levitt Pavilion west of Staples in Westport Village.
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Major interstates, bus routes and train lines are nearby
Sidewalks don’t line the neighborhood’s residential streets, so most people drive to run errands. U.S. Route 1, which is lined with stores and restaurants, anchors Staples to downtown Westport and nearby towns. This is also where residents find bus stops operated by the Greater Bridgeport Transit Authority, which has lines that go between Norwalk and Bridgeport. Commuters who work in New York City can connect with Interstate 95 to travel 55 miles to Manhattan. More commonly, they park at the Westport train station, about 4 miles from Staples, and board the Metro-North Railroad’s New Haven line. The train takes about 70 to 90 minutes to arrive at Grand Central Terminal. Staples also has a CAP Index crime score of 2 out of 10, which is lower than the national average of 4.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Post Rd. East & Opposite Sherwood Island Connector
Reviews
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Crime and Safety
1 - Low Crime, 10 - High Crime
Staples
US
Homicide
1
4
Sexual Assault
1
4
Assault with Weapon
1
4
Robbery
1
4
Burglary
3
4
Motor Vehicle Theft
2
4
Larceny
1
4
Crime Score
1
4
Source: WhatIsMyCrimeRisk.com
Staples Demographics and Home Trends
On average, homes in Staples, Westport sell after 73 days on the market compared to the national average of 58 days. The median sale price for homes in Staples, Westport over the last 12 months is $2,121,000, down 2% from the median home sale price over the previous 12 months.
Tucked at the end of one of Westport's most coveted cul-de-sacs, this 5-bedroom contemporary offers 6,310 sq ft of finished living space on just over a private acre, with a backyard path leading directly to Bedford Middle and Staples High School. From the foyer, a dramatic vaulted living room with skylights, built-ins and a floor-to-ceiling stone fireplace sets the tone. The glass-wrapped sunroom
Timeless design meets modern sustainability in this stunning shingle-style home, set on 1.5 private in-town acres. Sunlight fills every room through oversized Kolbe windows, showcasing park-like grounds and mature plantings. The kitchen impresses with custom cabinetry, a handcrafted zinc island, and top-tier Wolf and Sub-Zero appliances. Step outside to a spectacular bluestone patio with an
Tucked away towards the end of a quiet cul-de-sac in a prime central Westport location, this beautifully updated home offers the perfect blend of privacy, convenience, and lifestyle. Set on 1.05 acres and just moments from town, close to schools, shopping, and commuting options, this five-bedroom residence is designed for both everyday living and effortless entertaining. The heart of the home is
Set in Westport's sought-after Hunt Club neighborhood, this European-inspired Colonial offers over 6,300 square feet across three finished levels, including expansive recreation spaces and a dedicated home theater. A dramatic two-story entry introduces refined formal and informal rooms, including a fireplaced living room, formal dining room, private office, and an expansive eat-in kitchen with
Introducing 1 Coastal Court, a rare opportunity to own in Westport's only gated community, an exclusive four-lot enclave envisioned and built by Joe Feinleib, founder of Coastal Luxury Homes and one of Fairfield County's most respected builders.This private neighborhood blends timeless architecture with modern luxury. Each custom residence, ranging from 5,000 to 7,500 square feet, plus generous
Beautifully updated with main level primary suite and abundant additional living space for family and guests in this move-in ready townhouse. You will love the soaring ceilings, the open and very flexible floor plan and natural light that fills this home throughout the day. Enjoy coffee or dinner al fresco on your dedicated private patio - so rarely found in a condominium community. Almost fully
New construction by renowned Red Coat Homes, ideally set on a quiet cul-de-sac in a premier Westport neighborhood. Designed by architect Judith Larson, this exceptional home offers over 7,000 sq ft of refined living space on more than one acre, complete with a resort-style pool. Timeless architecture and sophisticated finishes create spaces ideal for entertaining, work, and everyday living, with
Tucked away in a storybook setting on over an acre of land, this beautifully rebuilt 3-bedroom home offers effortless one-level living surrounded by nature. A charming brook and picturesque wooden footbridges create a peaceful, private retreat unlike any other. Designed with an open floor plan and soaring vaulted ceilings, the sun-filled interior feels both spacious and inviting. The primary
New Construction by Westport Family Homes - Elevator, July Completion. Privately set at the end of a quiet cul-de-sac in the coveted Long Lots neighborhood, this 2.3-acre, flat, tree-lined property offers a rare combination of privacy and endless possibilities for creating a luxury compound. Introducing a truly exceptional estate by award-winning Builder, Westport Family Homes. The residence
We've saved the best for last! Of the 4 homes built at the end of this quiet and centrally located Westport cul-de-sac, this is the most expansive, and it's loaded with top-tier amenities. Entertain or hang out in style in gracious rooms curated by Susan Tracy Designs featuring a warm color palate, and not often found finishes like Venetian plaster and built-in hallway millwork. The open
RARE OPPORTUNITY TO CUSTOMIZE NEW CONSTRUCTION BY COASTAL LUXURY HOMES. PLANS APPROVED & PERMITS IN PLACE. CONSTRUCTION CAN BEGIN IMMEDIATELY, SAVE 6+ MOS ON NEW BUILD TIMELINE. This ultra luxury modern cul-de-sac residence features stucco exterior, DaVinci Boral roof, and expansive windows up to 10ft high. Main level includes luxe chef's kitchen w/ breakfast room opening to the great room with
Incredibly located moments from downtown, Winslow Park, commuting routes, schools, beaches & more, this grand home on an acre of landscaped property with a stunning gunite pool is ready to exceed your expectations. This sun-splashed home blends the best of a traditional Colonial with modern flair, including high ceilings, tall windows, generous room scale and features for maximum comfort
In-Town Living at its Finest! Tucked away at the end of a quiet cul-de-sac, this private 5-bedroom residence offers the perfect blend of space, comfort, and convenience on 1.5+ of beautifully landscaped acres. A sun-filled, custom eat-in kitchen serves as the heart of the home, featuring stainless steel appliances, a center island, and abundant natural light. The flexible floor plan is enhanced
Welcome future Ezra resident! Your carefree modern lifestyle awaits. Elegantly designed and finished high-tech Smart-Townhomes offer the best of every world! These stylish condominium-level finishes boast quartz kitchen islands and upgraded stainless steel appliance packages. Plenty of natural light shines through floor-to-ceiling windows. State-of-the-art Smarthome technology includes full
Spacious, furnished 5 Bedroom 3 full/ 2 half bath colonial located on a tranquil lot on a highly desirable Long Lots cul-de-sac. Generously sized rooms including gourmet kitchen and light filled sunroom with great flow provide the perfect place to spread out for work, learning, entertaining, relaxation, and play. The finished walk out lower level is complete with a walk in wine cellar, and
Suburban comfort mixed with urban convenience. Ideally located north of the Long Island Sound and one hour away from New York, our studio and one-bedroom homes are the perfect place to live and thrive. These Westport, CT, apartments are ready to satisfy all your needs through a wide range of amenities and services. Flexible lease terms are also available!Modern and airy – our residences recreate
Light-filled ranch style contemporary nestled at the end of one of Westport's most sought-after cul-de-sacs, close to schools, beaches and shopping. The main floor boasts open, airy rooms with niche spaces, all thoughtfully designed on one level. The kitchen has been tastefully renovated, complete with ample cabinetry, granite counters, a center island, and stainless steel appliances. The kitchen
All utilities included! Thoughtfully updated and full of character, this inviting Westport home perfectly balances charm, comfort, and convenience. This beautifully updated 2-bedroom home with an additional loft-style bedroom is filled with natural light and architectural appeal. Soaring vaulted ceilings create an open, airy atmosphere, while the renovated kitchen and bathrooms blend style and
Welcome home to Sue Terrace. This completely renovated and freshly painted colonial boasts 4BR/3FB and is being offered as a yearly, unfurnished rental. This family home is centrally located in Westport and walking distance to shopping (Fresh Market, Free People, CVS, Trader Joes, CAVA) Winslow Park and restaurants such as Terrain and Sakura. Prefer to entertain at home? 16 Sue Terrace has an
Beautifully remodeled 2 bedroom, 2 bath modular home in a prime Westport location available for a one or two year lease. Nestled within a well-maintained community just minutes to shopping, dining, beaches, and train access, this home offers convenience and easy living. Bright open floor plan featuring luxury vinyl plank flooring, updated kitchen with stainless steel appliances, and in-unit
Linda AlmonteBerkshire Hathaway NE Prop.
$25,000 per month
4 Beds
7 Baths
4,000 Sq Ft
Welcome to your Westport retreat, tucked away on a private street with a peaceful brook flowing just outside. This light filled home features an open Layout designed for comfort and ease. Just 2 miles from Compo Beach, you're close to the shoreline while still enjoying a quiet, secluded setting. Local Restaurants, cafes, and grocery stores are nearby without compromising privacy. A perfect place
This Westport residence is a meticulously executed Passive House retrofit of a modernist concrete home originally built in 1938. Few properties achieve this level of energy efficiency while also prioritizing non-toxic, health-conscious building materials. As you pass through the home's front entry gate and hear the gentle rhythm of tires over gravel, a striking and handsome facade comes into
Enjoy easy living in this charming 2-bedroom, 1-bath apartment located in a sought-after Westport neighborhood. Filled with natural light, the home features a spacious living room that opens to a modern kitchen with stainless steel appliances, a gas cooktop, and a wine refrigerator. Both bedrooms offer comfortable space, and hardwood floors run throughout the apartment, adding timeless appeal.
Welcome to 11 Twin Circle Drive, tucked within one of Westport's most quietly connected neighborhoods. Set on a private association of just two cul-de-sacs, the setting has the kind of easy, unhurried energy that's increasingly hard to find. A place where the street itself feels like an amenity, all just minutes from town, schools, trains, beaches, and everyday conveniences. The home balances
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
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