In-Town Real Estate

Welcome to In-Town Westport, a vibrant neighborhood nestled in the heart of one of Connecticut's most desirable towns. With its picturesque streets, charming boutiques, and a rich sense of community, In-Town offers a unique blend of suburban tranquility and urban convenience.

As you stroll through the tree-lined avenues, you'll discover an array of local shops, cafés, and restaurants that reflect the town's artistic spirit and culinary diversity. Whether you're in the mood for a cozy coffee shop or a fine dining experience, In-Town has something to satisfy every palate. The neighborhood is also home to the Westport Country Playhouse and various art galleries, making it a cultural hub for residents and visitors alike.

Families will appreciate the top-rated schools in the area, which are renowned for their commitment to academic excellence and extracurricular activities. The neighborhood's parks and recreational facilities provide ample opportunities for outdoor fun, whether it's a leisurely walk along the Saugatuck River or a day of play at one of the local playgrounds.

In-Town Westport is not just a place to live; it's a lifestyle. With easy access to the Metro-North train station, commuting to New York City is a breeze, making it an ideal location for professionals seeking the perfect work-life balance. The community is friendly and welcoming, fostering connections among neighbors, making it easy to feel right at home.

Discover the charm of In-Town Westport, where every corner exudes character and every street tells a story. Your dream home awaits in this enchanting neighborhood!

Newest Listings in In-Town

$1,100,000

ACTIVE Status ⋅ 24217449 MLS

3 Bedroom Cape in the heart of Westport set on a picturesque level .41 acre. Flat, pretty property with city water and sewer connected. Ideally located just a short walk to the heart of Westport, Main Street's high-end shops, amazing restaurants, the Saugatuck River, Winslow Park, the Westport Country Playhouse, the Westport Farmers' Market, The Levitt Pavilion, the Westport Library & more! Minutes to Compo Beach, Longshore Park and Golf Course, Ned Dimes Marina. Home is being sold "as-is". Amazing opportunity for a builder, designer, investor, buyer who understands the great potential in this most sought-after neighborhood.

61 Washington Ave, Westport

$1,100,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24216682 MLS

61 Washington Ave, Westport

$925,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24217459 MLS ⋅ Whitney Glen BLDG.

Move right into this gut renovated townhouse condo in Whitney Glen, a sought after community in Westport. Thoughtfully updated throughout, this sun filled home features a renovated kitchen, brand new bathrooms, and new flooring. The bright, open living room boasts soaring ceilings, a wood burning fireplace, and sliding glass doors leading to a private, covered deck, perfect for relaxing or entertaining. The main level also offers a spacious bedroom with sliders to another private deck and a beautifully renovated full bath. Upstairs, the primary suite features its own outdoor deck, a dressing room, and a brand new bathroom. An additional loft provides flexible space for a home office, reading nook, or overnight guests. A convenient laundry room is complemented by an extra large walk in closet for exceptional storage. The fully finished lower level offers even more versatility, ideal for a recreation room, home office, hobby space, or additional storage. Enjoy one assigned parking space, ample visitor parking, and easy access to the complex's heated saltwater pool. Experience comfortable, low maintenance living in a desirable Westport location where you can stroll to shopping, downtown restaurants and Westport town park. One resident must be 62 years of age or older.

39 Whitney Glen, Unit 39, Westport

$1,799,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24216042 MLS ⋅ The Mill BLDG.

Experience the pinnacle of sophisticated, carefree living in this stunning luxury condominium at Westport's historic and reimagined landmark, The Mill. Seamlessly combining chic modern aesthetics with resort-style amenities, Unit 311 offers a turnkey lifestyle of comfort and elegance. Step inside to an expansive, light-filled open floor plan featuring soaring floor-to-ceiling windows, pristine light wood floors, and a striking gas linear fireplace. The gourmet kitchen is a culinary masterpiece outfitted with Poliform cabinetry, Sub-Zero, Wolf, and Miele appliances, sleek custom cabinetry, and an open layout perfect for seamless entertaining. The primary suite serves as a private sanctuary complete with a generous dressing area and a spa-inspired en-suite bath boasting heated floors and a glass walk-in shower. The den/2nd bedroom is a flexible space that can accommodate a home office. A private heated garage and a locking storage room add to the ease of living. White-glove convenience is anchored by a front desk concierge to assist with your day-to-day needs. Residents also enjoy a state-of-the-art health and wellness center/gym, a sparkling pool, hot tub, outdoor grilling patio, common rooftop terrace, guest suite and an elegant residents' great room and cafe. Perfectly situated in-town close to Westport's finest dining, shopping, and scenic surroundings.

41 Richmondville Ave Unit 311, Westport

$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

$1,799,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24211506 MLS ⋅ The Mill Westport BLDG.

Welcome to The Mill offering a sophisticated, effortless approach to Westport living, pairing a distinctive setting with thoughtful amenities and the convenience of a condominium. Designed for those who appreciate style, The Mill combines modern architecture with an exceptional trove of luxuries and well-appointed spaces. This delightful, sun-lit unit provides luxurious features complementing the residence's refined aesthetic. New high-end appliances, large center island and ample storage in both kitchen and bedrooms include 2 walk-in closets in the primary suite. Residents enjoy a resort-like outdoor setting with pool, lounge area and grilling stations-perfect for a quiet afternoon or entertaining. The rooftop terrace adds an inviting place to gather. Inside, an elegant resident lounge and generous coffee station provides a comfortable setting for the daily ritual. A dedicated on-site concierge adds an additional level of service and convenience. The Mill provides a beautifully designed setting close to Westport's restaurants, shops, arts, culture and all transportation.

41 Richmondville Ave Unit 303, Westport

$1,949,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24209251 MLS ⋅ The Mill Westport BLDG.

Historic character meets refined modern design in this beautifully appointed one-bedroom plus den, two-bath residence at The Mill Westport. A gracious foyer provides a proper sense of arrival before opening into expansive living and entertaining spaces, where European white oak floors, historic replica windows, exposed brick, elegant lighting, and custom electric shades create a sophisticated backdrop. The open kitchen is outfitted with a suite of high-end appliances and an oversized island with generous seating, while a gas fireplace anchors the living room. Thoughtfully designed to live like a true two-bedroom, a custom sliding glass wall creates a private second sleeping area complete with a deep closet and direct access to a full bath. The spacious primary suite is tucked away on the opposite side of the residence and features a pair of closets outfitted by Poliform and a luxurious five-fixture bath with a freestanding soaking tub, walk-in rain shower, and heated floors. A full-size washer and dryer, parking, and storage are all included. Originally a historic candlewick mill dating to the 1800s, The Mill Westport has been thoughtfully reimagined as just 31 distinctive residences. Amenities include a pool and hot tub, fitness center, landscaped outdoor spaces, outdoor kitchen, residents' lounge, guest suite available for rent, and concierge services.

41 Richmondville Ave Unit 105, Westport

$220,000

ACTIVE Status ⋅ 24205902 MLS

A Rare Opportunity to Bring Your Culinary Vision to Life Step into a charming, intimate Italian restaurant with the kind of atmosphere you can't manufacture - cozy, welcoming, and full of character. This is the perfect canvas for a chef-owner or passionate foodie who dreams of creating unforgettable meals in a place that truly feels their own. The restaurant is fully equipped, thoughtfully laid out, and designed for comfort and connection. It's the kind of dining room where regulars get to know your name, where families celebrate milestones, and where great food is paired with genuine hospitality. Whether your dream is rustic Mediterranian comfort cuisine, regionally inspired specials, or a chef-driven tasting menu, this space is ready for your imagination - and your recipes. Instead of spending years building from scratch, you can step into an established setting and start cooking the food you love, for people who will truly appreciate it. If you've ever said, "One day I want my own place," - this could be that day.

Post Rd Rd, Westport

$2,650,000

ACTIVE Status ⋅ 24196614 MLS

Rare opportunity to build a custom residence on 1.2 acres in Westport. The previous home has been demolished, and the property is offered with approved architectural plans. Bring your preferred builder and collaborate with the project architect to tailor the design to your vision. Also listed as a to-be-built single-family residence.

4 Lantern Hill Rd, 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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In-Town Real Estate

Newest Listings in In-Town

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