5 bedroom homes for sale in Westport, CT

50 minutes on Rocket

$3,400,000

5 beds • 5 baths • 8,639 sqft

249 Sturges Hwy, Westport, CT 06880

#24099840, Lainie Floyd, Listing Office: William Pitt Sotheby's Int'l

4 days on Rocket

$2,895,000

5 beds • 4.5 baths • 5,424 sqft

20 Crawford Rd, Westport, CT 06880

#24098607, Lisa Tortora, Listing Office: Coldwell Banker Realty

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6 days on Rocket

$3,750,000

5 beds • 5.5 baths • 6,637 sqft

22 Woody Ln, Westport, CT 06880

#24096060, Douglas Bross, Listing Office: Coldwell Banker Realty

7 days on Rocket

$10,000 Closing Credit¹

$1,599,000

5 beds • 3 baths • 3,374 sqft

11 Valley Rd, Westport, CT 06880

#24097637, Cyd Hamer, Listing Office: William Pitt Sotheby's Int'l

$10,000 Closing Credit¹

$2,199,000

5 beds • 3.5 baths • 3,975 sqft

4 Plumtree Ln, Westport, CT 06880

#24097596, Debra Shaughnessy, Listing Office: Coldwell Banker Realty

$2,750,000

5 beds • 5.5 baths • 5,766 sqft

127 Easton Rd, Westport, CT 06880

#24090486, Polly Sykes, Listing Office: Compass Connecticut, LLC

Tour

$7,390,000

5 beds • 4.5 baths • 4,791 sqft

22 Apple Tree Trl, Westport, CT 06880

#24096214, Deborah Aulfinger, Listing Office: Goldan Home Realty, LLC.

Room to negotiate?

Median Sold Price

$1.9M

Avg. Sale Time

206 Days

Based on our April 2025 Market Report.

$4,999,000

5 beds • 3.5 baths • 6,172 sqft

21 Oak Ridge Park, Westport, CT 06880

#24096112, Tanya Sprague, Listing Office: William Raveis Real Estate

$3,125,000

5 beds • 4.5 baths • 5,780 sqft

54 N Ave, Westport, CT 06880

#24094099, Leslie Clarke, Listing Office: Compass Connecticut, LLC

$3,895,000

5 beds • 6.5 baths • 7,970 sqft

6 Florian Ct, Westport, CT 06880

#24081415, Lori Popkin, Listing Office: Coldwell Banker Realty

$2,697,000

5 beds • 4 baths • 4,549 sqft

26 Hitchcock Rd, Westport, CT 06880

#24093563, Mar Jennings, Listing Office: Higgins Group Bedford Square

$2,799,000

5 beds • 4.5 baths • 4,672 sqft

9 Forest Dr, Westport, CT 06880

#24091885, Alexander Chingas, Listing Office: Coldwell Banker Realty

$10,000 Closing Credit¹

$2,299,000

5 beds • 4.5 baths • 3,585 sqft

75 Old Hill Rd, Westport, CT 06880

#24089282, Regi Kendig, Listing Office: William Raveis Real Estate

Tour

$10,000 Closing Credit¹

$899,000

5 beds • 3 baths • 2,600 sqft

4 Robert Ln, Westport, CT 06880

#24091847, Inna Agujen, Listing Office: Coldwell Banker Realty

$2,999,000

5 beds • 6.5 baths • 4,854 sqft

12 Bauer Pl, Westport, CT 06880

#24087392, Brett Lieberman, Listing Office: The Riverside Realty Group

$3,955,000

5 beds • 4.5 baths • 5,056 sqft

16 Burr School Rd, Westport, CT 06880

#24091626, Danna Rogers, Listing Office: Higgins Group Bedford Square

$10,000 Closing Credit¹

$2,499,000

5 beds • 4.5 baths • 4,035 sqft

33 Pequot Trl, Westport, CT 06880

#24089634, Elaine Gibbons, Listing Office: Boost Real Estate Group

$3,250,000

5 beds • 5 baths • 6,027 sqft

99 Hillspoint Rd, Westport, CT 06880

#24091976, Susan Lieberman, Listing Office: The Riverside Realty Group

$3,675,000

5 beds • 5 baths • 4,668 sqft

91 Turkey Hill Rd S, Westport, CT 06880

#24026135, Robert Appell, Listing Office: Coldwell Banker Realty

Backup offers

$10,000 Closing Credit¹

$1,850,000

5 beds • 3.5 baths • 4,368 sqft

41 Hermit Ln, Westport, CT 06880

#24089500, Alexander Chingas, Listing Office: Coldwell Banker Realty

$3,599,999

5 beds • 5.5 baths • 5,887 sqft

5 Elwil Dr, Westport, CT 06880

#24090134, Tanya Sprague, Listing Office: William Raveis Real Estate

$3,375,000

5 beds • 4 baths • 3,700 sqft

3 Nassau Rd, Westport, CT 06880

#24072658, Douglas Bross, Listing Office: Coldwell Banker Realty

Backup offers

$10,000 Closing Credit¹

$1,925,000

5 beds • 4.5 baths • 3,378 sqft

14 Reimer Rd, Westport, CT 06880

#24083541, Brittany Strouse, Listing Office: Coldwell Banker Realty

$5,199,000

5 beds • 6.5 baths • 7,000 sqft

36 Maple Ave S, Westport, CT 06880

#24066794, Kelly Loucas, Listing Office: Compass Connecticut, LLC

$5,995,880

5 beds • 7 baths • 7,020 sqft

86 Maple Ave S, Westport, CT 06880

#24082092, Jaclyn Picarillo, Listing Office: Higgins Group Bedford Square

$6,205,176

5 beds • 7 baths • 6,302 sqft

24 Edgemarth Hill Rd, Westport, CT 06880

#24079968, Jaclyn Picarillo, Listing Office: Higgins Group Bedford Square

$11,800,000

5 beds • 6.5 baths • 10,800 sqft

260 Hillspoint Rd, Westport, CT 06880

#24075734, Elizabeth Steffen, Listing Office: Higgins Group Bedford Square

$3,500,000

5 beds • 4.5 baths • 4,669 sqft

216 Hillspoint Rd, Westport, CT 06880

#24071002, Robert Appell, Listing Office: Coldwell Banker Realty

$3,400,000

5 beds • 7 baths • 8,639 sqft

249 Sturges Hwy, Westport, CT 06880

#24069402, Lainie Floyd, Listing Office: William Pitt Sotheby's Int'l

$15,000,000

5 beds • 6 baths • 3,955 sqft

50 Compo Mill Cv, Westport, CT 06880

#24068879, Robert Perriello, Listing Office: Century 21 AllPoints Realty

Tour

$25,000,000

5 beds • 5.5 baths • 11,450 sqft

122 Beachside Ave, Westport, CT 06880

#24066972, Leslie Clarke, Listing Office: Compass Connecticut, LLC

$4,500,000

5 beds • 7 baths • 9,819 sqft

1 Flower Farm Ln, Westport, CT 06880

#24038760, Heather Fitzgerald, Listing Office: YellowBrick Real Estate LLC

Westport, CT Real Estate Market Overview

There are 32 5-bedroom homes for sale in Westport, CT. The following market insights reflect all property types in the Westport, CT real estate market. The number of homes for sale in Westport, CT increased by 34.6% between March 2025 and April 2025. In April 2025 median list price was $1,946,846 and the average listing age was 206 days. Westport, CT housing market in April 2025 saw over 10 listings sold above listed price, more than 2 sold at listed price and over 14 sold below.

From Rocket Homes Real Estate and based on county public records data

What is it like to live in Westport, CT

Overview

Westport is located in Fairfield County, Connecticut. There are roughly 26,719 residents, living in 9,677 households. The average temperature for Westport this time of the year is low of 49F and high of 69F. On average, Westport gets about 4.59 inches of precipitation in May. Most residents are home owners (84%), have a post secondary degree (62%) and are married, with kids (36%).

Data provided by Home Junction

Housing types

Westport's housing market is characterized by a diverse array of options, with a significant emphasis on single-family homes that exhibit a blend of colonial, contemporary, and Cape Cod architectural styles. The area also offers a selection of condominiums and townhouses, providing alternatives to the traditional detached home. The majority of Westport's residential buildings were constructed during a period of growth in the mid-20th century, with many homes featuring waterfront views and spacious lots.

Advantages

Westport is celebrated for its coastal charm and artistic heritage, with a community that prides itself on a rich cultural scene. The town's character is further enhanced by its vibrant arts community, numerous galleries, and the annual Westport Fine Arts Festival, which showcases local and national artists. The presence of the Westport Country Playhouse adds to the town's reputation as a hub for the performing arts.

Convenience

The community benefits from a robust educational system, including several public schools known for their academic excellence, as well as private institutions that cater to a range of educational needs. Westport's healthcare services are comprehensive, with facilities offering a variety of medical specialties. The town also features a public library system that serves as a resource and gathering place for residents. Retail and dining options in Westport reflect the local culture, with a mix of boutique shops and restaurants that range from casual eateries to upscale dining experiences.

Transportation

Westport's transportation infrastructure includes a well-connected network of roads, with easy access to major highways that facilitate travel to nearby cities. The town also has a train station that provides regular commuter service to New York City and other destinations. Public transportation options are available, with bus services connecting Westport to surrounding areas. The town is also bike-friendly, with several paths and lanes designated for cyclists, and it features walkable neighborhoods, particularly in the downtown area.

Schools near Westport, CT

Elementary Schools

Saugatuck Elementary School
170 Riverside Ave
Public District KG-5
Coleytown Elementary School
65 Easton Rd
Public District KG-5
Long Lots Elementary School
13 Hyde Ln
Public District KG-5

Middle Schools

Coleytown Middle School
Public District 6-8
Bedford Middle School
88 North Ave
Public District 6-8

High Schools

Staples High School
70 North Ave
Public District 9-12

Data provided by Great Schools

5 bedroom homes for sale in Westport, CT

Westport, CT Real Estate Market Overview

What is it like to live in Westport, CT

Overview

Housing types

Advantages

Convenience

Transportation

Schools near Westport, CT

Housing market reports in Fairfield County

Homes for sale near Westport, CT

Top real estate cities in Connecticut