Downtown North Real Estate

Welcome to Downtown North, a vibrant and charming neighborhood nestled in the heart of Westport, Connecticut. Known for its rich history and picturesque streets, Downtown North offers a unique blend of small-town charm and modern conveniences, making it an ideal place to call home.

As you stroll through the tree-lined avenues, you’ll discover a delightful array of boutique shops, art galleries, and cozy cafes that reflect the creative spirit of the community. The area is also home to a thriving dining scene, where you can savor everything from gourmet cuisine to casual fare, all within walking distance. Whether you're grabbing a morning coffee or enjoying an evening out, Downtown North has something to satisfy every palate.

Families will appreciate the top-rated schools and numerous parks that dot the neighborhood, providing ample opportunities for outdoor activities and play. The community is known for its strong sense of belonging, with regular events and gatherings that bring residents together, fostering connections and friendships.

For those who enjoy the arts, Downtown North is a cultural hub, featuring local theaters and galleries that showcase the talents of both established and emerging artists. The nearby Long Island Sound offers stunning waterfront views and recreational opportunities, making it easy to enjoy the beauty of nature right at your doorstep.

With its perfect blend of convenience, culture, and community spirit, Downtown North is not just a place to live—it's a lifestyle. Come and experience the warmth and charm of this enchanting neighborhood, where every corner tells a story and every resident feels at home.

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

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