Westport Real Estate

Welcome to Westport, Connecticut – a picturesque coastal town that perfectly blends charming New England character with modern sophistication. Nestled in Fairfield County, Westport is renowned for its stunning waterfront views along the Long Island Sound, offering residents a serene escape from the hustle and bustle of city life while still being conveniently located just an hour from New York City.

Rich in history and culture, Westport boasts a vibrant arts scene, with galleries, theaters, and music festivals that attract visitors and locals alike. The town's historic downtown area is lined with boutique shops, gourmet restaurants, and cozy cafes, making it a delightful place to spend a leisurely afternoon. For those who appreciate the outdoors, Westport is a paradise, featuring beautiful parks, nature trails, and beaches where families can enjoy picnics, swimming, and water sports.

Families will appreciate the town's top-rated school system, which is consistently recognized for its commitment to academic excellence and holistic development. Westport's community is welcoming and diverse, fostering a sense of belonging that makes it easy to call this town home.

Whether you’re looking to buy a charming colonial, a modern waterfront property, or a spacious family home, Westport's real estate market has something for everyone. With its combination of natural beauty, cultural richness, and a strong sense of community, Westport is not just a place to live – it’s a lifestyle waiting to be embraced. Discover the magic of Westport, where your dream home awaits amidst the enchanting backdrop of coastal Connecticut.

Newest Listings in Westport

$6,789,000

ACTIVE Status ⋅ 24217714 MLS

Don't miss the best waterfront value in Fairfield Cty with over 200' of PRIVATE Beach and water views from every room! New Survey and potential dock site. Set on one acre of waterfront property, One Driftwood Point holds views from every room of the Long Island Sound and Saugatuck Harbor on three sides and a perfect overlook of the tennis court to complete this property as of one of the most unique and stunning spots in Westport! Stretched out into the harbor, the modern contemporary style home is designed to feel immersed in the sparkle of water and sea breeze from each deck, every room, and all levels of open living space. The layout opens with a double height entry and leads upstairs to the massive living spaces that maximize the gorgeous light and waterfront surroundings - with a front to back living room set with multiple conversation areas and easy deck flow, the space is mirrored with a matching family room holding a lounge area, billiard room and 3 fireplaces in the house. An office and half bath finish off the top floor. On the main level, the dining room & kitchen enjoy the view of boats in the harbor. The primary bedroom suite with 2 bathrooms, and a walk-in closet/dressing room steps out to the main level deck overlooking the front yard & water beyond. The 2 main level bedrooms share a full bath. Driftwood Point lives like a full retreat, while it's actually moments from Saugatuck dining, shopping & train station conveniences and all Westport amenities

1 Driftwood Point Rd, Westport

$925,000

2 Beds ⋅ 2 Baths ⋅ COMING SOON 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

$1,350,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24216570 MLS

A storybook Cape Cod on a quiet cul-de-sac, a beautiful, level half-acre property, and an unbeatable Westport location-3 Allen Lane is a rare opportunity to make a home your own! Brimming with classic New England charm and possibilities, this inviting home offers the flexibility to move right in, thoughtfully update over time, or expand to suit your vision. One of its standout features is a desirable floor plan with all three bedrooms together on the second floor, an uncommon and welcome feature in a traditional Cape Cod. Two full bathrooms, a half bath, and a finished lower level, perfect for a playroom, recreation room, home office, or gym, add to the home's versatility. The expansive, level .54-acre property offers exciting potential for future expansion, including the possibility of adding a first-floor primary suite, subject to town approvals. Public water and sewer are additional advantages. And the location is exceptional! Tucked away in a peaceful neighborhood setting yet just minutes to downtown Westport, both the Westport and Greens Farms Metro-North train stations, schools, shopping, restaurants, and Compo Beach, everything that makes Westport such a desirable place to call home is close at hand. Whether you choose to embrace its timeless charm or transform it into the home you've always envisioned, 3 Allen Lane offers an increasingly hard-to-find combination of location, land, character, and potential. An opportunity not to be missed!

3 Allen Ln, Westport

$3,395,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ 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

$1,300,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 for the holidays!! 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 ⋅ 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

$7,900,000

6 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 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

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Westport Real Estate

Newest Listings in Westport

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