5 Best Neighborhoods to Live in Westport

Tucked along the shoreline of Long Island Sound, Westport remains one of the most coveted residential destinations in Fairfield County—and, indeed, the entire Northeast. With its classic coastal New England aesthetic, a thriving cultural scene, and proximity to Manhattan, Westport effortlessly blends luxury, community, and sophistication.

While known for its iconic downtown village, picturesque beaches, and storied artistic legacy, Westport neighborhoods define the town's lifestyle. From expansive estates in wooded enclaves to coveted waterfront retreats with sweeping views of Long Island Sound, each community offers a unique take on luxury living.

Below, we spotlight five of the most desirable neighborhoods in Westport for 2025.

Occupying the town's northernmost corner, Coleytown is arguably Westport's most sought-after residential area. Characterized by its considerable acreage, quiet roads, and mature landscapes, this neighborhood offers exceptional privacy and room to build or expand. Estate properties here often sit on two or more acres and range from classic Colonials to custom new builds. Top-tier schools and a close drive to downtown via Easton Road further enhance the area's pastoral charm.

Bordering Coleytown to the west and north of Merritt Parkway, Poplar Plains mirrors its neighbor's bucolic, New England charm. For many years considered the western half of Coleytown, this enclave of tucked away residences and large private lots developed its own distinct vibe with a variety of architecture, including stately Colonials, riverfront hideaways, European-influenced manors, and historic Cape Cods and farmhouses. While the neighborhood feels rural, its location is surprisingly central, providing convenient access to major routes—Merritt Parkway forms the community's southern boundary—and Westport amenities.

Coleytown is home to the 39-acre Newman-Poses Preserve, a serene natural area and public memorial to the late Paul Newman, who lived near the property. Meandering from Merritt Parkway to Calvary Road, Red Coat Road represents Poplar Plain's most sought-after luxury corridor. Quiet, exclusive, and architecturally refined—including the 1795-built Samuel Finch House—Red Coat Road is a distinctive avenue for those seeking residential distinction.

As Westport's oldest and perhaps most historically significant neighborhood, Greens Farms pairs timeless elegance and privacy with modern convenience and accessibility. Stretching from the town's eastern boundary with Southport to Hillspoint Road and the shores of Sherwood Millond, the area boasts private lanes, stone-wall-fronted estates, and historic charm dating back to the1600s. The most prestigious addresses lie along Beachside Avenue, with sweeping views of Long Island Sound and direct access to private beaches. 

Residents enjoy easy access to the Metro-North station, excellent schools, including private Greens Farm Academy and public Greens Farm Elementary School, and natural escapes like the Smith Richardson Preserve. Despite I-95 cutting through its southern half and the commercial corridor that is Post Road serving as its northern boundary, the neighborhood feels tucked away—a perfect combination of accessibility and exclusivity.

Considering Greens Farm is Westport's first official neighborhood, what better place to find Connecticut's first state park? Bounded by water on all sides, Sherwood Island State Park is a 235-acre oasis that brings together beach, coastal forest, and wetland habitats in spectacular fashion. Established in 1914 and expanded over the next 40 years, the park includes a nature center, pavilion, walking and nature trails, and a Living 9/11 Memorial.

Westport's coastal crown jewel, Compo Beach, is synonymous with relaxed seaside luxury. Nestled along the Saugatuck River's eastern shores as it meets Long Island Sound, this neighborhood Longshore Club Park, the Longshore Golf Course, and a casual, year-round vacation vibe. Compo's unique location also makes it a favorite among residents, with Interstate 95 forming its northern boundary and Westport's two train stations—Westport and Greens Farm—strategically located 2 miles to the west and 3 miles to the east.

Waterfront homes along Soundview Drive, Hillspoint Road, and Appletree Trail offer premium access to the shore. Historic residences in the Compo-Owenoke District add architectural depth to this sun-splashed enclave, which remains one of the most in-demand locales in town.

Often overlooked and all the more coveted for it, Manitou Road is a hidden gem east of the Saugatuck River, just off Ferry Lane. The private enclave features fewer than 40 homes—traditional estates and modern builds among them—many with direct river access, golf course views, or expansive wooded lots. Manitou's understated elegance makes it one of the most refined micro-neighborhoods in Westport.

Once a bustling industrial hub, Saugatuck and its neighboring peninsula to the south, Saugatuck Shores, have evolved into one of Westport's most dynamic neighborhoods. The inland Saugatuck is centered around its namesake river, stretching along its western banks from Westport Village to south of Interstate 95. Its northern edge features a walkable, village-like atmosphere with riverfront dining, boutique shopping, both Saugatuck and Kings Highway Elementary schools, and Birchwood Country Club. Saugatuck's southern region includes the Westport Train Station, Bridgebrook Marina, waterfront dining, and a seaside village atmosphere along Riverside Avenue.

Occupying a hook-shaped peninsula that extends just south of Saugatuck Avenue, Saugatuck Shores represents Westport's premier address for boating enthusiasts and a nautical lifestyle. Most homes have water views or frontage, including private docks with direct access to Long Island Sound. Further enhancing the waterfront theme is the presence of the Saugatuck Harbor Yacht Club and the Cedar Point Yacht Club.

In terms of waterfront living, Saugatuck and Saugatuck Shores are a showcase for neighborhoods featuring homes overlooking Westport's two primary waterfronts. The most celebrated properties are found in Burritt's Landing and Stony Point, both of which overlook the Saugatuck River, and Westport's southernmost community, Saugatuck Island, which is surrounded on three sides by Long Island Sound.

Old Hill blends historic character with a true sense of community. It provides residents with a captivating suburban lifestyle and proximity to downtown Westport and major thoroughfares while maintaining quiet tranquility. Old Hill's allure lies in its neighborly feel—elegant homes on one- to three-acre lots—many outfitted with tennis courts, pools, and grand entertaining spaces.

Spanning roughly 2.5 square miles, the neighborhood offers leafy streets, charming architecture, and easy access to many restaurants and boutiques--walkability is a key asset here. So, too, is the nearby Earthplace Nature Center, a 62-acre nature and wildlife sanctuary, as well as the prestigious Pierrepont School, the top-ranked private school in Connecticut.

One of the town's earliest settled areas, Old Hill is home to preserved Colonial and Federal-style homes, including those in the Kings Highway North Historic District. This exquisite neighborhood covers approximately 53 acres and includes 32 historic residences, half built between the early 1700s and the mid-1800s.

Westport's real estate market continues to evolve, but its best neighborhoods remain a reflection of what makes this Gold Coast enclave so enduringly attractive: character-rich homes, serene landscapes, vibrant culture, and easy access to both nature and New York City.

If you're ready to start the search for your Westport luxury dream home, contact Cindy Raney & Team today for the best combination of experience and expertise to help you confidently navigate the buying process and make your dream a reality.