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

$3,395,000

4 Beds ⋅ 5 Baths ⋅ 24217119 MLS

92 Compo Road N. pairs classic architecture, meticulous craftsmanship, private 1 acre property, pool and spa with an enviable near town location. Moments from Main Street's shops and restaurants, ball fields, tennis/pickleball courts, and 3 miles to Compo Beach, this custom Colonial offers a vibrant lifestyle and strong feeling of "Home Sweet Home". Approximately 5,500SF, this residence is finished on 4 floors and showcases light and bright gathering spaces, exceptional millwork, and bespoke cabinetry. It is complemented by thoughtfully redesigned and upgraded interiors, and substantial investments in exterior improvements and mechanical systems. Beautifully landscaped grounds are alive with color and texture and incorporate stone walls and fencing. The large entertaining patio and deck create an irresistible setting for entertaining and everyday living. 4 bedrooms occupy the second floor, including a spacious primary suite with dual walk-in closets, and a luxurious bath featuring double vanity, soaking tub, radiant-heated floors, and a heated towel rack. A third-floor bonus room offers built-in desks, lounge, attic storage, and rough plumbing in place for a future bathroom. The walkout lower level includes a gym, wine room with refrigeration, and recreation room with full bath (space could serve as a 5th bedroom). A distinctive opportunity to enjoy private outdoor living and exceptional convenience in one compelling Westport address.

92 Compo Rd N, Westport

$4,050,000

5 Beds ⋅ 8 Baths ⋅ 24215100 MLS

NEW CONSTRUCTION BY RENOWNED WESTPORT LUXURY BUILDER WALTER MATTERA IN THE CHERISHED FLOWER ESTATES NEIGHBORHOOD! An exceptional opportunity to own a brand-new 5-bedroom, 6-full and 2-half-bath luxury residence by Mattera Construction, one of Westport's premier luxury homebuilders, celebrated for timeless architecture, exceptional craftsmanship, and meticulous attention to detail. Set on a beautiful .40-acre property in Westport's desirable Downtown North neighborhood, 22 Fillow Street offers the rare combination of luxury new construction and the warmth and character of an established in-town community. Flower Estates is one of Westport's most cherished neighborhoods, where tree-lined streets, a welcoming atmosphere, and a genuine sense of community create an increasingly sought-after lifestyle. Just minutes from downtown Westport's shops and restaurants, approximately 10 minutes from the Westport train station and Compo Beach, and close to Coleytown Elementary School, the location offers convenience without sacrificing neighborhood charm. Walter Mattera brings his signature commitment to quality, architectural integrity, and thoughtful design to this exciting new residence. With construction just underway, this is a rare opportunity to own a beautifully crafted luxury home by one of Westport's most respected builders in a neighborhood where new construction opportunities are increasingly limited. Timeless craftsmanship. Exceptional location. The best of Westport living.

22 Fillow St, Westport

$2,499,000

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. Agent/Owner

53 Clinton Ave, Westport

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Downtown North Real Estate

Newest Listings in Downtown North

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