Downtown North Real Estate

Welcome to Downtown North, a vibrant and charming neighborhood nestled in the heart of Westport, Connecticut. Known for its picturesque streets and a delightful blend of historic charm and modern convenience, Downtown North is a community that captures the essence of coastal living while offering an array of amenities that cater to all lifestyles.

As you stroll through Downtown North, you'll be greeted by a unique mix of boutique shops, trendy cafes, and gourmet restaurants, each contributing to the neighborhood's lively atmosphere. The local farmers' market, held weekly, showcases fresh produce and artisanal goods, making it a favorite spot for residents to gather and connect. Art enthusiasts will appreciate the proximity to galleries and cultural venues that celebrate local talent and creativity.

Nature lovers will find themselves enchanted by the nearby parks and waterfront areas, where scenic trails and serene views invite leisurely walks and outdoor activities. The Saugatuck River, which winds through the area, offers opportunities for kayaking, fishing, and simply enjoying the tranquility of nature.

Families will appreciate the top-rated schools and community programs that foster a strong sense of belonging and support for children of all ages. With a rich history dating back to the 17th century, Downtown North is not just a place to live; it’s a place to thrive.

Whether you're seeking a cozy café for your morning coffee, a vibrant community event, or a peaceful park to unwind, Downtown North has it all. Experience the best of Westport living in this charming neighborhood that perfectly balances urban conveniences with a warm, welcoming community spirit.

Newest Listings in Downtown North

$2,650,000

5 Beds ⋅ 6 Baths ⋅ 24079819 MLS

Incredibly located moments from town and convenient to schools, shopping, commuting options and more, this sparkling home showcases pride of ownership. A new 2026 driveway leads to the landscaped setting, where this gracious home with an in-ground Wagner pool is set amid .74+/- acre. The two-story foyer introduces crisp, timeless spaces, and a home that has been impeccably maintained. The living rm w/ the first of 3 fireplaces and a beautiful dining rm w/lit tray ceiling are ready for entertaining. The large gourmet kitchen w/ marble counters, La Cornue range plus wall ovens, Sub Zero, island & pantry has a sun-filled breakfast rm that leads to the lrg fam rm w/ custom built-ins, stone fpl w/ gas log set & two sets of doors to the newer deck. The mudrm has a casual entrance, door to pool, half bath & access to the 3-car garage. Upstairs, a hall w/ window seats leads to the primary suite w/ fpl, dual walk-in clsts & luxe bth. Each remaining BR is spacious & well-appointed. A flexible area w/ the 5th BR & study/play rm could become an in-law suite. The finished 3rd flr is a wonderful space for a play rm or hobbies. The vast lower level includes a great rm, a den/lib w/ custom built-ins & a full bath. The usable backyard leads to a fenced-in Wagner gunite pool w/ a "pool house." This entire home and property is in outstanding, mint condition. There is nothing for you to do but move in and enjoy this fine luxury residence.

53 Clinton Ave, Westport

$1,250,000

24158331 MLS

Nestled on a charming historic street in one of Westport's most desirable neighborhoods, 15 Gorham Avenue offers a rare opportunity to build your dream home just moments from the heart of town. This exceptional property allows for the construction of a approximately 2,500+/- square foot residence, perfectly suited for today's lifestyle while blending beautifully with the character of the surrounding historic homes. The lot features a lovely, private backyard-ideal for outdoor entertaining, gardens, or peaceful relaxation. Enjoy the convenience of a true walk-to-town location with easy access to Westport's vibrant downtown, restaurants, shops, parks, and train. Whether you envision a classic New England colonial or a thoughtfully designed modern home, this property provides the perfect setting to create something special in a highly sought-after Westport neighborhood.

15 Gorham Ave, Westport

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.