Connecticut's Gold Coast
Coleytown
Coleytown occupies the northern reach of Westport, bordering the Weston town line along North Avenue and Newtown Turnpike.
About 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.
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Country Living in Coleytown
Coleytown is the part of Westport that surprises people. Drive north on Weston Road or Easton Road past the commercial core, past the subdivisions, and the landscape opens. Stone walls line the roads. Lots stretch to an acre, two acres, sometimes more. The canopy thickens. It does not look like a town with a median home price above $2 million, but it is.
The Coley family settled here in the 1700s and farmed the area for generations. That agricultural heritage left behind large parcels that were never subdivided to the density seen in southern Westport. Today the lots accommodate substantial homes set back from the road, screened by mature hardwoods and evergreens. Many of the original colonial structures survive, their post-and-beam bones still visible alongside modern additions. New construction tends toward contemporary colonials and transitional designs that respect the wooded setting rather than competing with it.
Newman-Poses Preserve is the neighborhood's signature green space. The 39-acre sanctuary, assembled from a donation by Paul Newman and adjacent parcels sold by the Kafka family, threads through meadows, upland woods, and a stretch of the Aspetuck River. The one-mile loop trail off Bayberry Lane draws hikers and birders year-round. Nearby, the Aspetuck Valley Country Club and the Patterson Club provide private recreational options. Coleytown is not isolated from amenities; it simply keeps them at a measured distance.
Coleytown Elementary School, an A-plus-rated K through 5 school with a 12-to-1 student-teacher ratio, anchors the neighborhood's identity. Students feed into Coleytown Middle School and then Staples High School. The school names are not coincidental; this is a community whose institutions carry the same family name as the land, a continuity that few Fairfield County neighborhoods can claim.
What Draws Buyers to Coleytown
- •Newman-Poses Preserve offers 39 acres of meadow, woodland, and Aspetuck River frontage with a one-mile loop trail
- •Coleytown Elementary School holds an A-plus rating with a 12-to-1 student-teacher ratio and 83% reading proficiency
- •Lot sizes typically range from one to three acres, among the largest residential parcels in Westport proper
- •Stone-wall-lined roads and mature hardwood canopy create a rural landscape within a top-ranked suburban school district
- •Aspetuck Valley Country Club and Patterson Club provide private golf, tennis, and swimming nearby
Housing in Coleytown
Coleytown's housing stock reflects its agricultural past and its present-day premium positioning. Original colonial farmhouses dating to the 1800s still stand on several properties, often expanded with sympathetic additions that preserve their historic character. Mid-century colonials and Cape Cods from the 1950s and 1960s fill many of the interior streets, while newer construction from the 2000s and 2010s introduces contemporary colonial and transitional designs on cleared lots. Lot sizes are the defining feature. Most properties sit on one to two acres, with some exceeding three acres near the Weston border. This scale accommodates long driveways, detached garages, pools, and significant privacy screening. The average sale price in Coleytown hovers around $2.3 million, with newer or fully renovated homes on larger parcels pushing above $3 million. Split-level and ranch-style homes from the mid-century represent the neighborhood's lower price tier, typically trading between $1.3 million and $1.8 million.
Real Estate in Coleytown
Coleytown appeals to buyers who want acreage and privacy without leaving Westport's school district. That combination is increasingly rare in lower Fairfield County, where most towns have been subdivided to half-acre or quarter-acre density. Inventory turns over slowly here because homeowners have the space to renovate and expand rather than sell. Buyers relocating from New York City or from denser Westport neighborhoods south of the Post Road often discover Coleytown late in their search and wish they had started here. The tradeoff is distance: downtown Westport's shops and the train station are a ten-to-twelve-minute drive. For families whose priority is land, trees, and a top elementary school, that tradeoff rarely matters.
Market Snapshot
Coleytown Market Snapshot
Residential real estate trends for Coleytown, Westport, Connecticut.
Active Listings
9
7 under contract
Median List Price
$3.55M
9 active listings
Median Closed Price
$2.42M
40 sales
Median Days on Market
76
9 active listings
Median $ / Sq Ft
$574
9 active listings
Sale-to-List Ratio
99.8%
40 sales
Based on 9 active listings and 40 closed sales (trailing 12 months). Source: SmartMLS · As of July 27, 2026.
+46.6%
Pricing Posture
current asking median vs trailing 12-month closed median in Coleytown
40
Sales Activity
closed sales in Coleytown over the trailing 12 months (-4.8% vs prior 12 mo)
6,611 sq ft
Typical Home Size
median size across the Coleytown active sample
Homes for Sale in Coleytown, Westport
0 listings available
Listing information is supplied by SmartMLS, Inc.and other licensed IDX sources for consumers' personal, non-commercial use. Data is deemed reliable but is not guaranteed and should be independently verified.
© 2026 Smart MLS, Inc. All rights reserved.
Getting Around Coleytown
Coleytown is the farthest Westport neighborhood from the coastline and the train stations, positioned roughly four miles north of downtown. The Westport Metro-North station on Saugatuck Avenue is a ten-to-twelve-minute drive south, with express trains reaching Grand Central Terminal in approximately 60 minutes. I-95 is accessible via Exit 17, also about ten minutes south via Weston Road or Route 57. The Merritt Parkway (Route 15) runs closer, with the Westport interchange roughly five minutes from Coleytown's center, providing a scenic alternative route toward Stamford or New Haven. Downtown Westport's Main Street restaurants and Bedford Square shops are a ten-minute drive. The Weston town center and its farm stands are equally close heading north. Coleytown rewards drivers but is not practical as a walk-to-town neighborhood.
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Frequently Asked Questions About Coleytown
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