In-Town Homes for Sale

Welcome to In-Town Westport, a charming neighborhood nestled in the heart of Fairfield County, Connecticut. Known for its picturesque streets and vibrant community spirit, In-Town offers an ideal blend of suburban tranquility and urban convenience. Just a stone’s throw away from the stunning shores of Long Island Sound, residents enjoy easy access to beautiful beaches, scenic parks, and a plethora of outdoor activities.

In-Town is renowned for its rich cultural scene, featuring boutique shops, delightful cafes, and award-winning restaurants that cater to every palate. The neighborhood is also home to a variety of art galleries and theaters, making it a hub for creativity and expression. Families will appreciate the top-rated schools and community programs that foster a nurturing environment for children to thrive.

When it comes to homes for sale in In-Town Westport, buyers are met with a diverse array of options that cater to various tastes and lifestyles. From charming historic homes that exude character to modern constructions boasting contemporary amenities, there’s something for everyone. Many properties feature spacious yards, perfect for entertaining or relaxing in the sun, while others offer stunning views of the surrounding landscape.

With its prime location, rich community life, and a wide selection of homes, In-Town Westport is not just a place to live; it’s a place to call home. Explore the available listings today and discover the perfect property that suits your needs and dreams in this enchanting neighborhood!

Newest In-Town Homes for Sale

$1,248,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24215287 MLS

Ideally located within walking distance of downtown Westport, 310 Main Street offers a unique opportunity to enjoy the convenience of in-town living while creating a home that suits your lifestyle. The main level features a living room with a wood-burning fireplace, an open kitchen with granite countertops and dining area, and French doors leading to a private stone patio. A primary suite with en-suite bath and two additional bedrooms complete the main level. The finished lower level offers additional flexibility, with two potential bedrooms and a full bath, providing options for guests, recreation, or multigenerational living. A two-car garage and private outdoor space add to the appeal. An especially compelling feature is the existing town-approved home occupation setup, with a separate entrance, two offices, and a waiting room-ideal for a professional practice or home-based business (subject to applicable approvals). Whether you envision updating the existing home to reflect your personal style or exploring the possibility of expanding upon the existing home, 310 Main Street offers versatility, opportunity, and an exceptional location close to Westport's shops, restaurants, and amenities.

310 Main St, Westport

$1,199,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24211260 MLS

Ideally situated in a highly walkable in-town location, this charming 1928 home offers a rare opportunity to create something truly special in the heart of Westport. Set on a lovely private lot, the property combines classic character with a wonderfully convenient setting close to shops, restaurants, schools, and all that downtown Westport has to offer. Owned and cherished by the same family for approximately 40 years, the home retains the warmth and architectural details that give an older house its distinctive appeal. Oak floors, gracious proportions, and timeless character provide a wonderful foundation for its next chapter. A first-floor in-law/primary bedroom suite, thoughtfully added in the 1960s, offers convenient one-level living and adds flexibility to the original floor plan. Upstairs, two roomy bedrooms share a generously sized bathroom that presents an exciting renovation opportunity: the space could be reconfigured to create two en-suite bathrooms, one for each bedroom, adding modern functionality while preserving the home's charm and character. While the house is in need of renovation, its established setting, private grounds, classic details, and highly desirable in-town location make it an exceptional opportunity for those looking to restore, renovate, and make the home their own. For buyers seeking in-town convenience, privacy, and authentic Westport character, this is a special property with tremendous potential.

280 Main St, Westport

$4,250,000

6 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 24165540 MLS

Exceptional new construction by AR Luxury Homes with 7,500+/- square feet of thoughtfully designed living space across four finished levels in a prime Westport location. This 6-bedroom, 6 full and 3 half bath residence blends refined craftsmanship with modern functionality, featuring an open-concept layout ideal for both everyday living and entertaining. The heart of the home is a custom-designed kitchen equipped with premium appliances including Wolf and Sub-Zero, expansive island, and seamless flow to the family room with fireplace. Three fireplaces throughout the home add warmth and architectural interest. White oak flooring, custom millwork, and high-end finishes elevate every space. The upper levels offer a luxurious primary suite with spa-like bath and custom closet, along with well-appointed secondary bedrooms. A fully finished lower level with walkout access provides flexible space for recreation, fitness, or additional living. Set on a level .50-acre property, the outdoor experience is complete with a 15' x 30' heated gunite pool, bluestone patio, and professionally planned landscaping-perfect for enjoyment and relaxation. Additional features include city water and sewer, propane gas, 400-amp electrical service, 24 KW generator, and wiring for audio, security, and smart home systems. A rare opportunity to own a new construction home with exceptional scale, quality, and amenities. Still time to customize finishes.

6 Janson Dr, Westport

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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.

In-Town Homes for Sale

Newest In-Town Homes for Sale

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