In-Town Homes for Sale

Welcome to In-Town Westport, a charming neighborhood nestled in the heart of Fairfield County, Connecticut. Known for its vibrant community spirit and picturesque surroundings, In-Town offers a delightful blend of suburban tranquility and urban convenience. Just a stone’s throw away from the beautiful shores of Long Island Sound, this neighborhood is perfect for those who crave a lifestyle filled with both relaxation and recreation.

In-Town is characterized by tree-lined streets, historic homes, and a warm sense of community. Residents enjoy easy access to a variety of local boutiques, gourmet restaurants, and cultural attractions, making it a hub for entertainment and leisure. The Westport Public Library and the Westport Country Playhouse are just a few highlights that showcase the area’s rich cultural heritage. Additionally, the nearby parks and beaches provide ample opportunities for outdoor activities, from picnicking to kayaking.

For those seeking a new home, In-Town Westport presents an array of stunning properties for sale. From charming colonial-style houses to modern, sleek designs, there is something to suit every taste and lifestyle. Many homes feature spacious yards, updated interiors, and proximity to top-rated schools, making it an ideal choice for families. With a thriving real estate market, now is the perfect time to explore the opportunities that await you in this desirable neighborhood.

Discover the magic of In-Town Westport, where community, convenience, and character come together to create a truly exceptional living experience. Your dream home is waiting for you in this enchanting corner of Connecticut!

Newest In-Town Homes for Sale

$2,999,000

6 Beds ⋅ 6 Baths ⋅ 24192039 MLS

Nestled in the heart of Westport, Connecticut, this stunning new construction residence redefines elegant suburban living with unparalleled sophistication, timeless grace and is complete and ready for immediate occupancy. Boasting six generous bedrooms and six luxurious bathrooms, the home features soaring nine-foot ceilings that bathe its expansive interiors in natural light and create an atmosphere of airy grandeur. Thoughtfully designed with premium finishes, custom millwork, and state-of-the-art systems. From the chef's kitchen with Thermador Appliances and a commanding kitchen island to the serene primary suite with a warming fireplace and a walk in closet fit for royalty; every detail invites effortless entertaining and refined daily living. Spanning three floors, this home offers exceptional versatility with a peaceful third floor sanctuary housing a private office and media room for entertainment or productivity. The finished lower lever further elevates the lifestyle with a spacious additional family room and an exercise studio, creating inviting spaces for relaxation, recreation, and personal wellness. Set against Westport's coveted landscape, located across from Winslow Park and upscale shopping, this exceptional property offers a rare opportunity to embrace modern luxury within one of Fairfield County's most distinguished communities.

36 E Main St, Westport

$2,895,000

5 Beds ⋅ 4 Baths ⋅ 24182424 MLS

Saint John Place is the street people who know Westport quietly hope opens up. It almost never does. Reimagined in 2007 by Renato Gasparian Associates and refreshed in 2022, this house has all the right moves. Inside, the main level opens up the way you hope it will. The great room stretches nearly thirty-four feet and flows into the dining area and a kitchen built around a center island, with a custom walk-in pantry right behind it. A sun room pulls in the morning light. There's a separate family room, plus a real office with a door that closes. Upstairs, five bedrooms give everyone somewhere to land. The primary suite has a spa bath with a soaking tub, a separate shower, and two walk-in closets (because who likes to share?). The laundry is up here too, in its own room. The outdoor spaces close the deal. A bluestone patio wraps around a good portion of the house with a stone fireplace. The deep flat lot is screened by mature plantings and gives you the privacy people leave town to find. You're in the heart of Westport's in-town neighborhood, which means the car can stay in the driveway. Walk to a different cuisine every night, the shops, the Library, the Westport Country Playhouse, summer nights at the Levitt Pavilion. The Saugatuck River is right there, and a celebrated omakase counter is a few minutes on foot. When you do want the car, the beach is a short drive away. Beautiful house, easy life, almost everything a walk from the door. Tour online @ 30saintjohn.com

30 Saint Johns Pl, 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

$2,395,000

6 Beds ⋅ 6 Baths ⋅ 24164783 MLS

Built in 2022, 40 Richmondville Avenue offers generous scale, a thoughtful layout, and true move-in-ready ease. Bright, open-concept main level connects kitchen, dining, and living spaces, with high ceilings and oversized windows throughout. The kitchen features a full Thermador appliance suite, large island with integrated outlets, extensive cabinetry, walk-in pantry, and mudroom with built-ins. Upstairs includes a spacious primary suite with walk-in closet and spa-like bath with heated floors, soaking tub, and oversized shower. Two bedrooms are connected by a Jack and Jill bath, each with lofted spaces for added flexibility. Additional bedrooms offer options for guests, office, or evolving needs. Third floor provides a private, multi-purpose level, while the finished lower level includes polished concrete floors and a bar/kitchenette area for casual entertaining. Six bedrooms, five-and-a-half baths, and four finished levels offer exceptional flexibility. Located just minutes from downtown Westport, with easy access to shopping, dining, and beaches, in an area experiencing continued growth.

40 Richmondville Ave, Westport

$1,329,000

3 Beds ⋅ 3 Baths ⋅ 24158630 MLS

Spacious sophistication in the heart of Downtown Westport. Perfectly positioned just moments from shopping, dining & recreation, this lovely in-town home offers a rare blend of comfort, flexibility, and location. The inviting living room with wood-burning fireplace sets the tone for relaxed gatherings and quiet evenings alike. The open-concept kitchen features granite countertops and flows seamlessly into the dining area, with French doors leading to a private stone patio - ideal for morning coffee or alfresco entertaining. The main level includes a spacious primary suite with en-suite bath, along with two additional BRs. Downstairs, the finished lower level offers additional space with two more bedrooms and a full bath, offering flexible space for guests, rec/playroom, or multi-generational living. For those seeking a professional setup, the town-approved home occupation designation allows for a separate entrance, two offices, and a waiting room - a turnkey solution for small business owners or remote professionals. With quick access to the Westport Library, Levitt Pavilion, and the town's vibrant dining & shopping scene, this property delivers both lifestyle and convenience. Nearby commuting options include the Metro North Railroad to NYC, Merritt Parkway, I-95. A rare opportunity to live and work in one of Fairfield County's most sought-after communities, or to find a home that offers private space for visitors or extended family. AVAILABLE FOR RENT AT $6,700/mo.

310 Main St, Westport

$999,000

4 Beds ⋅ 2 Baths ⋅ 24158900 MLS

Set on a picturesque 0.30-acre lot, this ranch-style home is full of potential and waiting for your creative vision. While the home is being sold as-is the possibilities are endless. Whether you're an investor, a builder, or a homeowner with a vision, this property offers the perfect canvas to bring your ideas to life. Situated in a sought-after neighborhood with close proximity to downtown, shopping, beaches and parks, this property pairs endless possibilities with an unbeatable location. In this private road residence has access to a dock on the on the picturesque Saugatuck River where neighbors can go kayaking tubing or simply soak in the serene views

20 Woods Grove Rd, Westport

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