---
canonical: "https://caiolafinehomes.com/towns/westport"
tenant: "fairfield"
brand: "Matt Caiola Luxury Properties"
town: "Westport"
slug: "westport"
region: "Fairfield County"
state: "CT"
lat: 41.1415
lng: -73.3579
seo_title: "Westport CT Real Estate | Luxury Homes & Arts Culture"
seo_description: "Explore Westport, Connecticut homes from waterfront estates to village neighborhoods. Schools, commute times, and market data. Contact Matt Caiola today."
generated_at: "2026-07-27T06:38:28.897Z"
last_modified: "2026-03-05T03:58:13Z"
---

# Westport Real Estate Overview

> Westport straddles the Saugatuck River along Connecticut's Gold Coast, balancing a nationally recognized arts scene anchored by the Westport Country Playhouse with nearly 20 square miles of waterfront, nature preserves, and residential neighborhoods. The downtown along Main Street and Post Road draws comparisons to the best small-town commercial districts in the Northeast.

## Summary
Westport straddles the Saugatuck River along Connecticut's Gold Coast, balancing a nationally recognized arts scene anchored by the Westport Country Playhouse with nearly 20 square miles of waterfront, nature preserves, and residential neighborhoods. The downtown along Main Street and Post Road draws comparisons to the best small-town commercial districts in the Northeast.

## About
The Saugatuck River splits Westport roughly in half, and that divide shapes much of the town's geography and character. West of the river, Old Hill preserves Revolutionary- and Victorian-era homes on wooded lots. East of it, the Compo Beach and Greens Farms neighborhoods stretch toward Long Island Sound, where Sherwood Island State Park - Connecticut's first state park, designated in 1914 - anchors more than 230 acres of shoreline, wetlands, and walking trails. Two Metro-North stations serve the town: Westport station in Saugatuck and Greens Farms station to the south. Express trains reach Grand Central Terminal in roughly 70 minutes; local service runs about 80.

Downtown Westport clusters where Main Street meets the Post Road and the Saugatuck River. The commercial stretch mixes independent boutiques - Bungalow, named the most beautiful store in Connecticut by Architectural Digest - with national brands like Theory and Lululemon. Anthropologie occupies the restored 1924 Bedford Mansion in Bedford Square. Playhouse Square, adjacent to the Westport Country Playhouse, adds another node of retail and dining. Across the river, Terrain's greenhouse cafe on the Post Road serves a seasonally driven menu inside a garden retail space that has become a destination in itself.

Westport's cultural identity runs deeper than most Fairfield County towns. The Westport Country Playhouse, founded in 1931 and renovated into a state-of-the-art facility in 2005, stages a professional season that draws audiences from across the region. MoCA Westport provides visual and performing arts programming. The Levitt Pavilion on Jesup Road hosts one of the longest-running free outdoor concert series in the country, with music, dance, theater, and its signature RiverSwing evenings throughout the summer. Paul Newman lived here from 1960 until his death in 2008, and the town's creative legacy continues to attract writers, artists, and media professionals.

Schools are a primary driver of residential demand. Westport Public Schools rank as the second-best district in Connecticut, and Staples High School earns consistent top-five placement statewide with a GreatSchools rating of 10 out of 10. Bedford Middle School carries an A+ Niche grade. On the private side, Greens Farms Academy serves K-12 with an 8:1 student-to-teacher ratio and strong STEM rankings. School quality is a factor in nearly every purchase decision here.

Seven neighborhoods give Westport its range. Compo Beach offers direct Sound access and the iconic Minuteman statue marking the 1777 British landing. Coleytown borders Weston with colonial homes and the Newman-Poses Preserve. Greens Farms, the oldest section of town, has its own train station and Burying Hill Beach. Long Lots stretches north from the Post Road with properties that still include working farmland, the Fairfield County Hunt Club, and Westport's oldest house, dating to 1690. Saugatuck, the original commercial heart of Westport, has reinvented itself around waterfront dining at spots like The Whelk and Rive Bistro. The variety means nearly every buyer profile - from young families to downsizers - can find a foothold.

## Lifestyle
Two Metro-North stations - Westport and Greens Farms - put the town on the New Haven Line with express service to Grand Central in about 70 minutes and locals running closer to 80. Both stations have dedicated parking, and most commuters are at a platform within ten minutes of home. I-95 and the Merritt Parkway provide highway access north toward Hartford and south toward Stamford and New York.

The dining scene has matured well beyond country-club fare. The Whelk, Bill Taibe's seafood-driven restaurant in Saugatuck, set a new standard when it opened and still anchors the waterfront strip. Rive Bistro serves French bistro cooking along the Saugatuck River. OKO brings omakase-level Japanese to the Post Road. Terrain's greenhouse cafe is as much an experience as a meal. The Westport Farmers' Market runs year-round - outdoors on Imperial Avenue in warmer months, indoors across the river through winter and spring.

Weekends revolve around the water and the arts. Compo Beach has a sandy shoreline, basketball courts, a skate park, and pickleball. Longshore Club Park operates more like a resort than a municipal facility, with an 18-hole golf course, tennis courts, a pool, a sailing school, and a marina. Sherwood Island State Park draws birdwatchers and kayakers. In the evenings, the Levitt Pavilion's free summer concert series fills the lawn, and the Westport Country Playhouse runs a professional theater season from spring through fall.

## Market Notes
Westport's median sale price crossed $2 million in 2025, and the average single-family home sold for approximately $2.75 million - up from $2.48 million the prior year. Luxury inventory concentrates above $4 million, with multiple active listings north of $10 million in waterfront and estate sections. Condominiums and townhomes remain scarce; new projects like The Gables of Westport bring limited supply at premium price points.

Among the four top Gold Coast markets - Greenwich, Westport, Darien, and New Canaan - Westport showed the most measured pace in 2025. Homes averaged about 37 days on market before going under contract, and pricing alignment mattered more than in recent years. Buyers had time to evaluate condition and value, which made accurate pricing essential for sellers. Overpriced listings lingered while well-positioned homes traded cleanly.

Entry points exist but require strategy. Condos and smaller homes near the Post Road or in Saugatuck offer the most accessible path in, though inventory is tight. For buyers targeting the $1.5 million to $3 million range, preparation and speed still matter - that segment draws the most competition from relocating families prioritizing Staples High School and the Westport school district. Above $5 million, the market rewards patience and selectivity.

## Highlights
- Two Metro-North stations on the New Haven Line with express service to Grand Central Terminal in approximately 70 minutes
- Westport Country Playhouse, founded in 1931, stages a professional theater season recognized across the region
- Sherwood Island State Park preserves over 230 acres of beachfront, wetlands, and trails - Connecticut's first state park
- Staples High School ranks in the top five Connecticut public high schools with a perfect 10/10 GreatSchools rating
- Longshore Club Park provides public access to an 18-hole golf course, tennis courts, pool, sailing school, and marina
- Downtown Main Street and Bedford Square mix independent boutiques with national brands in a walkable riverside setting
- Levitt Pavilion hosts one of the nation's longest-running free outdoor performing arts series each summer

## At a Glance
- **Population:** 27,141
- **Median age:** 45.3
- **Median household income:** $250,000+
- **Per-capita income:** $132,680
- **Owner-occupied homes:** 87.7%
- **Median year built:** 1960
- **Median home value:** Near top-code
- **Land area:** 20.0 sq mi
- **Population density:** 1,357 per sq mi (MODERATE)

_Source: U.S. Census Bureau American Community Survey (ACS) (as of 2024-12)._

## Walk, Bike, and Transit Scores
- **Walk Score:** 71 — Very Walkable
- **Bike Score:** 41 — Somewhat Bikeable

_Source: Walk Score._

## Points of Interest

### coffee
- [Terrain Cafe](http://www.shopterrain.com/westport-restaurant/)
- [Starbucks Coffee Company](https://www.starbucks.com/store-locator/store/1016243)
- [GG & Joe](https://www.ggandjoe.com/)
- [Kneads](http://www.kneadsbakerycafe.com/)
- [fatto a mano bakery](http://www.fattoamanobreads.com/)

### restaurants
- [bartaco](https://bartaco.com/location/westport/)
- [Terrain Cafe](http://www.shopterrain.com/westport-restaurant/)
- [Nômade Westport](https://nomadewestport.com/)
- [Romanacci Westport Train Station](https://www.romanacci.com/)
- [CAVA](http://cava.com/)

### parksTrails
- [Sherwood Island State Park](http://www.ct.gov/deep/sherwoodisland)
- [Earthplace](https://earthplace.org/)
- Winslow Park
- [Westport Longshore Club Park](https://www.westportct.gov/Home/Components/FacilityDirectory/FacilityDirectory/2/)

### fitness
- [[solidcore] Westport](https://solidcore.co/studios/westport?siteId=471005&locationId=1&utm_source=google&utm_medium=search&utm_content=local-listing&utm_campaign=gmb-listing)
- [Saugatuck Rowing and Fitness Club](https://www.saugatuckrowing.com/)
- [Body Fit Training Westport](https://www.bodyfittraining.com/location/westport)

_Source: Google Places._

## Schools
**District:** [Westport Public Schools](https://www.westportps.org)

### Elementary Schools
- **Coleytown Elementary School** — Grades K-5, 65 N Compo Rd, Westport, CT 06880
- **Greens Farms Elementary School** — Grades K-5, 17 Morningside Dr S, Westport, CT 06880
- **Kings Highway Elementary School** — Grades K-5, 125 Post Rd W, Westport, CT 06880
- **Long Lots Elementary School** — Grades K-5, 13 Hyde Ln, Westport, CT 06880
- **Saugatuck Elementary School** — Grades K-5, 170 Riverside Ave, Westport, CT 06880

### Middle Schools
- **Bedford Middle School** — Grades 6-8, 88 N Ave, Westport, CT 06880
- **Coleytown Middle School** — Grades 6-8, 255 N Ave, Westport, CT 06880

### High Schools
- **Staples High School** — Grades 9-12, 70 N Ave, Westport, CT 06880

_Source: Connecticut State Department of Education (as of 2024-2025)._

## Property Taxes
- **Mill rate:** 18.62
- **Assessment ratio:** 70%
- **Fiscal year:** 2024-2025
- **Assessor:** https://www.westportct.gov/government/departments-a-z/assessor-s-office

_Source: Connecticut Office of Policy and Management (OPM). Mill rates are set annually by each municipality. Property taxes are calculated as: (Assessed Value × Mill Rate) / 1000. Assessed value in CT is typically 70% of fair market value._

## Listings
Browse active listings: https://caiolafinehomes.com/home-search?town=westport

## Neighborhoods
- [Coleytown](https://caiolafinehomes.com/towns/westport/coleytown) — Coleytown occupies the northern reach of Westport, bordering the Weston town line along North Avenue and Newtown Turnpike. Named for the Coley family, who farmed this land for over two hundred years, the neighborhood retains a rural scale that the rest of Westport has largely outgrown. The 39-acre Newman-Poses Preserve and the trails of the Aspetuck Land Trust define its open spaces.
- [Compo Beach](https://caiolafinehomes.com/towns/westport/compo-beach) — Compo Beach is Westport's coastal anchor, a neighborhood defined by the 29-acre town beach on Long Island Sound and the 169-acre Longshore Club Park just up Compo Road South. The Saugatuck River borders its eastern edge, and Sherwood Mill Pond sits to the west. Streets like Bluewater Hill and Minute Man Hill hold some of the highest land values in Fairfield County.
- [Downtown Westport](https://caiolafinehomes.com/towns/westport/downtown) — Downtown Westport lines both banks of the Saugatuck River where Main Street meets the Post Road, concentrating the town's best restaurants, retail, and cultural institutions within a compact walkable grid. The Westport Country Playhouse has staged productions here since 1931. Bedford Square anchors the newer commercial core with Anthropologie, Spotted Horse Tavern, and a roster of independent boutiques. This is the civic and commercial heart of one of Connecticut's wealthiest towns.
- [Greens Farms](https://caiolafinehomes.com/towns/westport/greens-farms) — Greens Farms is Westport's estate district, stretching south from the Post Road to the Long Island Sound between Hillspoint Road and Sasco Creek. Sherwood Island State Park occupies 235 acres along its western boundary. Greens Farms Academy, a PreK-through-12 independent school housed in a former Vanderbilt estate on Beachside Avenue, has educated Fairfield County students since 1925.
- [Long Lots](https://caiolafinehomes.com/towns/westport/long-lots) — Named for the narrow colonial-era land parcels drawn for farmers in the 1600s, Long Lots stretches across Westport's residential interior. The 40-acre Fairfield County Hunt Club anchors the neighborhood, and Staples High School - ranked among the top public high schools in Connecticut - sits on North Avenue at its eastern edge. Between the Post Road and Cross Highway, the streets here are wide, the lots generous, and the pace distinctly unhurried.
- [Old Hill](https://caiolafinehomes.com/towns/westport/old-hill) — A 58-acre district on the west bank of the Saugatuck River, Old Hill preserves Westport's most historically significant residential enclave - where the c. 1730 Lt. John Taylor House still stands at the corner of Old Hill Road and Kings Highway North. The Kings Highway North Historic District, listed on the National Register of Historic Places since 1998, preserves an unbroken streetscape of wood-frame homes dating from the colonial era through the early twentieth century. Downtown Westport's Main Street shops and restaurants are a short walk across the river.
- [Saugatuck](https://caiolafinehomes.com/towns/westport/saugatuck) — Saugatuck is where Westport meets the water and the rail line. The neighborhood wraps around the Saugatuck River and the Westport Metro-North station, with Riverside Avenue running north past The Whelk, Black Duck Cafe, and Tarantino into a residential district of colonials, capes, and newer waterfront construction. The name itself is a Native American word meaning mouth of the river - and the river still defines everything here, from the yacht clubs to the dining to the commute.

## Frequently Asked Questions

### How long is the train commute from Westport to New York City?

Metro-North express trains from Westport station reach Grand Central Terminal in approximately 70 minutes. Local service takes closer to 80 minutes. The town also has a second station at Greens Farms, which adds roughly 5 to 10 minutes to the trip depending on the schedule. Both stations offer commuter parking with free access evenings and weekends.

### What are the main neighborhoods in Westport, CT?

Westport has seven primary neighborhoods: Compo Beach (waterfront with direct Sound access), Coleytown (wooded colonials bordering Weston), Downtown Westport (Main Street shops and restaurants along the Saugatuck River), Greens Farms (the oldest section with its own train station and Burying Hill Beach), Long Lots (larger properties stretching north toward Fairfield), Old Hill (historic homes west of the river), and Saugatuck (the original commercial center, now a dining and waterfront destination).

### What are home prices in Westport, Connecticut?

The median sale price in Westport is approximately $2 million, and the average single-family home sells for around $2.75 million. Condominiums and townhomes offer more accessible entry points but are limited in supply. Waterfront estates and properties in premium locations regularly list above $5 million, with some exceeding $10 million. Pricing varies significantly by neighborhood and proximity to the water.

### How are Westport public schools ranked?

Westport Public Schools rank as the second-best school district in Connecticut. Staples High School places in the top five statewide and holds a 10 out of 10 GreatSchools rating along with an A+ Niche grade. Bedford Middle School also carries an A+ overall grade. The private option, Greens Farms Academy, serves K through 12 with an 8:1 student-to-teacher ratio and strong STEM programs.

### What cultural attractions distinguish Westport from other Fairfield County towns?

Westport has one of the strongest arts scenes on the Gold Coast. The Westport Country Playhouse, founded in 1931, produces a professional theater season. MoCA Westport offers visual and performing arts year-round. The Levitt Pavilion stages one of the longest-running free outdoor concert series in the country each summer, with music, dance, and theater. The town's creative legacy traces back decades - Paul Newman was a longtime resident and driving force behind the Playhouse.

## Citation
- Canonical page: https://caiolafinehomes.com/towns/westport
- Tenant: Matt Caiola Luxury Properties