Westport Homes for Sale & Real Estate Listings

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About Westport, Connecticut

Westport beckons those seeking an idyllic blend of history and contemporary living. Living in Westport means embracing a lifestyle deeply rooted in its storied past while enjoying the comforts of a vibrant, thriving community. Let's explore the real estate trends, lifestyle, and the rich history that make Westport a truly unique place to call home.

Historical Charm Meets Modern Convenience: Westport boasts a rich history dating back to its founding in 1835. This history is beautifully preserved in its picturesque downtown, lined with charming boutiques and historic architecture. Beyond the town's timeless charm, Westport embraces modern living with a strong focus on sustainability. Real estate trends in Westport reflect a growing interest in eco-friendly homes, with many properties featuring cutting-edge green technologies. Residents enjoy access to award-winning schools, a robust arts scene, and a deep connection to the Long Island Sound.

The Westport Lifestyle: Westport's lifestyle is a testament to the town's enduring appeal. It's a place where art enthusiasts, nature lovers, and families can all find their niche. The town offers a rich cultural scene, including the Westport Country Playhouse and vibrant art galleries. With its pristine beaches and picturesque parks, outdoor enthusiasts can explore the wonders of nature year-round. Westport's commitment to preserving open spaces and fostering a strong sense of community creates an environment where residents can truly thrive.

Experience Westport: Living in Westport is a celebration of the past, present, and future. Its real estate trends mirror the town's commitment to sustainability, while its lifestyle offers a harmonious blend of cultural richness and natural beauty. Discover the timeless allure of Westport, where history and modernity coexist seamlessly in a coastal paradise.



What is the housing market like in Westport today?
The Westport housing market is somewhat competitive. The median sale price of a home in Westport was $2.4M last month, up 27.9% since last year. The median sale price per square foot in Westport is $494, up 8.0% since last year.

How hot is the Westport housing market?
Westport is somewhat competitive. Homes sell in 36.5 days.

Westport Real Estate Updates

Read the latest news, tips, and insights for the Westport real estate market.

Understanding Real Estate Market Cycles

John Schiaroli  |  June 4, 2024

Navigating real estate cycles to maximize returns and minimize risks.

The Effect of Fairfield, CT, Interest Rates on the Real Estate Market

John Schiaroli  |  May 17, 2024

Navigating affordability, demand, and investment opportunities.

Understanding New Canaan Housing Inventory: Supply and Demand

John Schiaroli  |  April 29, 2024

Analyzing real estate dynamics.

How to Maximize Your Home's Real Estate Market Potential

John Schiaroli  |  April 3, 2024

Elevating your property’s value to new heights.

5 Benefits of a Pre-Listing Home Inspection for Sellers

John Schiaroli  |  February 28, 2024

A guide to this important step.

Westport, CT, Real Estate Market Prices, Trends, and Forecast 2024

John Schiaroli  |  February 28, 2024

Exploring Westport’s dynamic real estate landscape.

6 Advanced Improvement Projects To Add Value To Your House

John Schiaroli  |  January 29, 2024

Focus on these luxury upgrades for maximum impact.

4 Tips for Handling Multiple Offers on Different Homes

John Schiaroli  |  January 29, 2024

Mastering the art of making multiple offers.

The Next Chapter: Renovation Tips for Empty Nesters

John Schiaroli  |  January 4, 2024

Transforming your home in this new phase of life.

The Impact of Seasonality on the Real Estate Market

John Schiaroli  |  January 4, 2024

A guide to getting the timing right.

The Legal Aspects of Home Selling in Westport, CT

John Schiaroli  |  November 28, 2023

Get ready for a successful sale with this guide.

Best Options for Home Warranty Plans For Sellers

John Schiaroli  |  November 28, 2023

A comprehensive guide.

The Ultimate Westport, CT, Home Seller's Guide

John Schiaroli  |  October 17, 2023

Create a top-notch strategy for selling your home with this comprehensive guide.

How to Market Your Home to Out-of-State Buyers

John Schiaroli  |  September 6, 2023

Learn how to improve your outreach to long-distance buyers.

13 Home Pricing Strategies: Expert Tips and Recommendations

John Schiaroli  |  September 6, 2023

Follow this expert guide to achieve a winning sale!

Preparing Your Home for Sale: Staging and Curb Appeal Tips

John Schiaroli  |  September 1, 2023

Read on to create a truly alluring space, both indoors and out.

5 Crucial Things You Shouldn’t Lie About When Applying for a Mortgage

John Schiaroli  |  April 4, 2023

When it comes to applying for a mortgage, remember that there's no such thing as a little “white lie.”

Make It Fab! 7 Things You Can Add to Your Yard This Spring if You’re Looking to Update Your Outdoor Space

John Schiaroli  |  April 18, 2023

Your backyard is an extension of your home and with the right additions.

What is a Listing Agreement? A Basic Guide for Home Sellers

John Schiaroli  |  April 25, 2023

Signing any contract can be nerve-wracking and intimidating.


The real estate market in Westport is characterized by strong demand and high property values, reflecting the town's desirability as a prime living destination in Fairfield County. This market strength is driven by Westport's excellent schools, proximity to New York City, and appealing coastal lifestyle. There's a trend toward spacious homes that offer privacy and luxury amenities, catering to affluent buyers and families seeking quality living. Waterfront properties, particularly along the Long Island Sound and Saugatuck River, are especially sought after for their views and exclusivity. The market has seen significant activity, with homes often selling at or above asking price, indicating a competitive environment for buyers.

Compared to other areas in Connecticut, Westport's housing market stands out for its higher price points and luxury property offerings. The town is one of the most affluent in the state, attracting a high-end market segment looking for upscale living experiences. Westport’s homes are renowned for their diverse architectural styles, from charming New England colonials to modern waterfront estates. The community's focus on arts, culture, and high-quality public amenities, along with its scenic coastal setting, contributes to higher property values and demand compared to many other Connecticut towns.

Westport offers a diverse range of homes to fit various lifestyles and preferences. Buyers can find everything from historic homes with traditional New England charm to contemporary estates featuring the latest in design and technology. The town is known for its spacious properties with sizable yards, offering a blend of suburban space and privacy. Waterfront homes, often featuring private docks and stunning views, represent the pinnacle of luxury in Westport. Additionally, there are a number of new developments and renovated homes that provide modern conveniences and energy-efficient living.

Investing in a home in Westport can be a sound financial decision, especially for those looking for long-term value and a high quality of life. The town's consistent demand, driven by its excellent schools, proximity to New York City, and strong community amenities, supports stable property appreciation. Westport’s real estate market has historically shown resilience, maintaining its value even during broader market downturns. However, as with any investment, buyers should consider the local market conditions, property location, and long-term trends when making a decision.

Potential buyers in Westport should consider several key factors. Location within the town is important, especially in terms of proximity to schools, downtown amenities, and waterfront areas. Assessing the size, condition, and style of the home, as well as the property’s landscaping and outdoor space, is crucial. Buyers should also be mindful of the community's zoning regulations and any potential for future development in the area. Considering the local real estate market trends and future growth potential of Westport is also advisable. Additionally, understanding the tax implications and assessing the overall lifestyle that a property in Westport offers can help ensure a fulfilling and sound investment.

Work With Us

Knowing that a real estate transaction is more than just a “transaction” is what John prides himself in understanding. His natural ability to forge long-term working relationships that almost always become friendships is what John loves about his work.

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