In-Town Real Estate

Welcome to In-Town Westport, a vibrant neighborhood nestled in the heart of one of Connecticut’s most desirable towns. Known for its charming atmosphere and community spirit, In-Town offers a unique blend of suburban tranquility and urban convenience.

Imagine waking up to the sound of birds chirping and the gentle rustle of leaves as you step outside to explore your picturesque surroundings. In-Town is characterized by its tree-lined streets, historic architecture, and an eclectic mix of shops and eateries that cater to all tastes. From artisanal coffee shops to gourmet restaurants, the culinary scene here is a delightful adventure waiting to be discovered.

Families will appreciate the top-rated schools that Westport is renowned for, providing an exceptional education for children of all ages. The neighborhood is also home to numerous parks and recreational facilities, perfect for outdoor enthusiasts who enjoy jogging, biking, or simply soaking up the sun.

In-Town Westport boasts a strong sense of community, with frequent local events that bring residents together. Farmers' markets, art shows, and seasonal festivals create a lively atmosphere, making it easy to connect with neighbors and forge lasting friendships.

With its prime location just minutes from the stunning Connecticut coastline, residents can enjoy beach outings and water activities, all while being conveniently close to the hustle and bustle of downtown Westport.

In-Town is more than just a neighborhood; it’s a lifestyle. Whether you’re looking for a cozy family home or a chic urban retreat, In-Town Westport offers the perfect backdrop for your next chapter. Come and experience the charm of this delightful community!

Newest Listings in In-Town

$1,799,000

2 Beds ⋅ 2 Baths ⋅ 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 ⋅ 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 ⋅ 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 ⋅ 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

1 Beds ⋅ 2 Baths ⋅ 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

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

$819,000

3 Beds ⋅ 2 Baths ⋅ 24199434 MLS

Great opportunity for Investors, Builders or First Time Home Buyers to renovate or Tear Down and Build a New House in Westport. 3-4 Bedrooms & 2 Bath Cape in need of Rehab. House has Spacious Living Room, Kitchen, Dining area Full bath on the first Floor, Master Bedroom, Full bath & Family Room on 2nd floor. Family Room can be converted into 4th Bedroom. House is Close to Downtown, Shopping, Dining, Recreation and Bus Line. Sold AS IS. Cash Offers and Quick Closing Preferred. Agent/Partner

383 Main St, Westport

$2,650,000

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

$4,850,000

5 Beds ⋅ 5 Baths ⋅ 24172211 MLS

Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate where classic Arts & Crafts architecture meets the tranquility of a private countryside retreat. Set on over 2.5+ sprawling acres of pristine grounds, this exceptional 5 Bed, 5 Bath residence offers more than 5,100 sqft of refined living, surrounded by natural beauty & complete privacy. From the moment you arrive down the private, meandering drive framed by mature landscaping; The Winslow Manor evokes a sense of warmth, character, and enduring craftsmanship. Rich architectural details, beamed ceilings, inviting living spaces, & thoughtfully designed interiors create a home that feels both grand and deeply welcoming- as if stepping into a piece of cozy history, carefully preserved and elevated for modern living. Designed for both relaxation & recreation, the estate unfolds into an extraordinary outdoor experience. A sparkling Gunite pool, multiple terraces, Pergolas, & dedicated home gym create the ultimate summer retreat, while the surrounding pond and protected wetlands attract an abundance of wildlife, offering peaceful views and a connection to nature rarely found so close town.

22 Evergreen Ave, Westport

$4,250,000

6 Beds ⋅ 9 Baths ⋅ 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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