Westport Real Estate

Welcome to Westport, Connecticut – a picturesque coastal town nestled in the heart of Fairfield County. Known for its stunning landscapes, vibrant culture, and rich history, Westport offers a unique blend of suburban charm and urban sophistication. With its prime location along the Long Island Sound, residents enjoy breathtaking waterfront views, sandy beaches, and a plethora of outdoor activities.

Westport boasts a thriving arts scene, with numerous galleries, theaters, and music venues that celebrate both local talent and renowned artists. The town is home to the Westport Country Playhouse, a historic theater that has been entertaining audiences since 1931. Additionally, the vibrant downtown area is filled with boutique shops, gourmet restaurants, and cozy cafes, making it a perfect spot for leisurely strolls and social gatherings.

For families, Westport is known for its exceptional school system, which consistently ranks among the best in Connecticut. The community is dedicated to education, providing students with a wealth of resources and opportunities to thrive. Parks and recreational facilities abound, offering everything from sports fields to serene walking trails, ensuring that residents of all ages can stay active and engaged.

Westport’s rich history is evident in its charming colonial architecture and historic landmarks, which tell the story of a town that has evolved while preserving its heritage. Whether you're looking for a peaceful retreat or a vibrant community, Westport is a place where you can truly feel at home. Come discover the magic of Westport – where coastal beauty meets a lively community spirit!

Newest Listings in Westport

$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

$3,950,000

6 Beds ⋅ 7 Baths ⋅ 24186096 MLS

Some homes are simply unforgettable. Set high above the street on 1.19 lush acres in coveted Old Hill, this extraordinary new residence blends striking architecture and sophisticated design. A gracious front porch overlooks a courtyard-like driveway. Created by Sam Development LLC.,CMS Architects, and Interior Designer Mary Beth Woods, this distinctive home offers approximately 6,000 SF across four levels, with 5 bedrooms, 5 baths, 2 half baths, 9' ceilings on the first and second floors, 6" white oak flooring, and exceptional details. The spectacular kitchen features high-end appliances, oversized island and walk-in pantry, opening to the family room with gas fireplace and breakfast area. Glass sliders lead to a granite patio and landscaped grounds. An elegant dining room with built-in buffet and bar and a glass doored living room/study complete the main level. The vaulted, beamed primary suite features a spa-like bath and two walk-in closets. Three additional bedrooms, spacious laundry, finished third- floor space with half bath, and a lower level with family room, bedroom,full bath, gym, and storage offer versatility. The detached 1,050 SF ADU is ideal for in-laws, guests, office/studio, or future pool house. Three-car garage with bonus room, spray-foam insulation, approximately 100 recessed lights. 22-KW Generac generator, 400-amp electrical services, and EV outlet. Come experience this exceptional Old Hill property and discover a home that stands apart.

217 Wilton Rd, Westport

$3,450,000

4 Beds ⋅ 4 Baths ⋅ 24216789 MLS

Welcome to 17 Greenbrier Rd- an irreplaceable masterpiece that perfectly balances elite, high-end refinement with effortless daily livability. Nestled high in a vibrant New England landscape with expansive treetop views, this 2023 frame-in restoration by Wimmer & Wimmer Design has been taken to the next level by the current owner. A striking, organically dark facade introduces its classically modern roots. Inside, the minimalist-luxe interiors are anchored by 6-inch rift-sawn hardwoods, TruStyle doors, and architectural trim under brilliant Lutron controlled smart LED lighting. The gourmet kitchen by NuKitchens is a chef's dream, meticulously styled with Sub-Zero, Wolf, and Caesarstone. Spa-level bathrooms showcase custom Porcelanosa tile, curbless glass showers, floating vanities and new Toto Neorest bidet toilets. The primary suite is a wellness escape complete with a 70-inch almond soaking tub. Outfitted with the absolute best-Marvin windows, Dornbracht, Villeroy & Boch, Robern, Rocky Mountain hardware, and Clopay doors-no expense was spared. The private resort-style grounds feature a newly resurfaced gunite swimming pool with spa and waterfall, expansive stone patios, and a refurbished clay tennis court. Experience the enchanting vibe and unique community of Greenbrier. Turn-key ready: This home can be purchased fully furnished, including the curated pieces of art and decor.

17 Greenbrier Rd, Westport

$5,500,000

4 Beds ⋅ 4 Baths ⋅ 24216438 MLS

One spectacular property-endless possibilities. Boasting 175 feet of direct Westport waterfront with a private community beach, this 1.23-acre Saugatuck harborside estate awaits your vision. Enjoy expansive views overlooking the vibrant harbor and a parade of yachts. The property currently features a classic 4,000 sq. ft. Colonial set high on the land, offering a charming canvas ready for a custom renovation. For buyers looking to build anew, this premier waterfront location comes with fully approved plans and permits in hand to construct a bespoke dream home. Whichever path you choose, the outcome is unparalleled: an incredible opportunity to live your waterfront dream adjacent to the coveted Saugatuck Yacht Club. Enjoy the very best of Westport living, with Saugatuck Village's top restaurants and the train station just moments away. Come take a look for yourself and let's chat!

14 Great Marsh Rd, Westport

$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

$1,300,000

2 Beds ⋅ 3 Baths ⋅ 24215497 MLS ⋅ Harvest Commons BLDG.

Warm and welcoming from the moment you enter - this light and bright new condominium offering will make you feel at home. Vaulted ceilings, gleaming hardwood floors throughout the main level and numerous updates elevate this gem of an opportunity. The private entry patio includes a thoughtfully curated Zen garden, with plenty of space for outdoor entertaining and easy flow from both the living room and kitchen. A most desirable floor plan with main level primary suite and fully renovated bath with step in shower. Generous rooms throughout, including the living room with fireplace and brick accent wall, a dedicated formal dining room that opens to a second outdoor patio plus a powder room for guests. The spacious kitchen includes newer stainless appliances, granite counters as well as an informal dining area. The first floor also boasts the laundry room and mudroom plus interior access to the attached two car garage. Everything you need on one level plus a fully finished upper level including an open loft/office/studio space, a massive additional bedroom for family or guests and the second full bath. Superior cul-de-sac location in this highly desirable, well managed community. Harvest Commons offers country club amenities including a pool, pool house and two Har-Tru tennis courts. Enjoy worry free living and easy access to shopping and dining, the beaches, highways and the railroad in a most convenient Westport location.

313 Harvest Commons Unit 313, Westport

$4,450,000

6 Beds ⋅ 8 Baths ⋅ 24215185 MLS

YES - we have the CO!! :) The home you've been waiting for is ready for sale and yes; you can close and move in in time to host Thanksgiving!! How much would you love a home with two acres on the Aspetuck River? Located only a mile from the Coleytown schools, next to a cul de sac? And yes, of course, it's not just the river; there's also a 20x40 salt water gunite pool. CCO Habitats presents; a new construction home with over 8300 sf of finished space on 3 floors. Wider homes are better than taller homes. It just makes sense. No one wants to walk all the way up to a finished third floor; the 2nd floor should be private - without people walking past or on top of your bedrooms. This is a floorplan you will love, with not only 2 designated offices, but with a private first floor bedroom as well. Organic modern, warm & inviting, with a calming palette sure to blend with & enhance your personal taste. An open starfish floorplan for togetherness as well as privacy. 10 foot ceilings on the first floor. Luxurious European oversized doors and tilting windows provide amazing natural light. Custom cabinetry throughout. 6 bedrooms, 6/2 bathrooms. All of the bedrooms are ensuite with walk in closets. The wine room - where it belongs - in the dining room. An amazing gym that will tempt even the people least prone to exercise into movement. A walk-out lower level that doubles as a pool house, complete with a second laundry, full bath, wet bar and entertaining space. Come home.

159 Easton Rd, 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

$7,900,000

6 Beds ⋅ 7 Baths ⋅ 24211051 MLS

Exceptional architecture, refined craftsmanship, and a country/coastal lifestyle. This spectacular Westport estate, to be built by Soundmark Luxury Homes, offers a rare expression of timeless elegance and modern luxury. Set on 2 pristine acres, framed by mature trees and expansive sky views, this special property exudes a sense of place, beauty, and permanence. With over 9,000 square feet of exquisitely designed living space, this remarkable residence blends sophisticated interiors with effortless comfort. Every detail has been thoughtfully considered, from dramatic windows and graciously proportioned rooms, to custom millwork, sophisticated lighting, and carefully curated finishes. An elegant floor plan offers inviting gathering spaces, a stunning chef's kitchen, and first and second floor luxurious Primary Bedroom Suite options. Outdoors, a heated gunite pool anchors a spectacular resort-like setting, complemented by a beautifully appointed Pool House featuring a kitchen, full bath, and sauna. Perfect for intimate gatherings or grand-scale entertaining, the residence offers a seamless connection between indoor and outdoor living. Nestled in Greens Farms, Westport's most coveted enclave, and just moments from beautiful beaches, Longshore Club and Golf, downtown shopping and dining, and convenient train service to NYC. A unique offering where design, generous proportions, and resort-inspired amenities create a lifestyle of understated luxury.

61 Clapboard Hill Rd, 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

$1,649,000

2 Beds ⋅ 3 Baths ⋅ 24214379 MLS ⋅ Terra Nova At Westport BLDG.

Move right in to this pristine townhome in Westport's exclusive Terra Nova condominium association. Located in one of the most desirable areas within the Terra Nova complex, the spacious home features an open floor plan, expansive rooms and tall ceilings. Highlights include a private elevator to all three levels of the home, two gas fireplaces, five-inch white-oak hardwood floors, SubZero, Bosch and Thermador kitchen appliances and private outdoor space with a natural gas barbecue connection. The fully finished walk-out lower level is great flexible-use space, suitable for entertaining, office, home gym, playroom, family and guests. The townhomes all encircle a beautifully landscaped swimming pool. Terra Nova is located moments from shopping, restaurants, Westport Library, Levitt Pavillion, Westport Country Playhouse, Compo Beach, excellent schools and Metro-North Railroad.

58 Terra Nova Cir Unit 58, Westport

$4,999,999

24215220 MLS

The property consists of 17 waterfront acres including a 7 acre upland section.

2-A Owenoke Park, Westport

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Westport Real Estate

Newest Listings in Westport

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