Westport Real Estate

Welcome to Westport, Connecticut – a picturesque coastal town nestled in the heart of Fairfield County. Known for its stunning waterfront views and vibrant community, Westport boasts a unique blend of small-town charm and modern sophistication. With a rich history dating back to the 17th century, this charming town has evolved into a sought-after destination for families, professionals, and artists alike.

Westport's scenic beauty is matched only by its cultural offerings. The town is home to an array of galleries, theaters, and music venues, providing residents with a vibrant arts scene. The renowned Westport Country Playhouse and the Westport Arts Center host a variety of performances and exhibitions throughout the year, ensuring there’s always something to see and do.

For outdoor enthusiasts, Westport offers an abundance of recreational opportunities. The town's pristine beaches, such as Compo Beach and Burying Hill Beach, invite residents to soak up the sun, enjoy water sports, or take leisurely strolls along the shoreline. The extensive network of parks and trails, including the scenic Saugatuck River, provides perfect settings for hiking, biking, and picnicking.

Education is a cornerstone of the Westport community, with highly-rated schools that prioritize student success and well-rounded development. Families are drawn to the town not only for its educational excellence but also for its strong sense of community and welcoming atmosphere.

With its charming downtown filled with boutique shops and gourmet restaurants, Westport is a place where you can enjoy the best of both worlds – a tranquil suburban lifestyle with easy access to the bustling metropolitan areas of New York City. Discover the allure of Westport, where your dream home awaits amidst a vibrant community and breathtaking natural beauty.

Newest Listings in 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

$1,525,000

4 Beds ⋅ 3 Baths ⋅ 24214592 MLS

This is the address Westport commuters wait for. Beyond the welcoming foyer, the main level unfolds across gleaming hardwood floors: a sunny living room, a dining room crowned by a crystal chandelier, and a white kitchen with glass-front cabinetry, stone counters, a peninsula for casual meals and stainless appliances. The showstopper is the vaulted great room, where a beamed beadboard ceiling soars above a floor-to-ceiling stone fireplace and a wall of windows with a built-in window seat. Step out to the screened porch and dining deck, overlooking a level, partially fenced yard framed by mature trees. Three bedrooms and 2 baths complete the main floor. The finished lower level adds a family room with a second fireplace, a fourth bedroom or home office with a walk-in closet, a full bath, laundry and an attached two-car garage. Walk to the train and skip the parking permit. King's Highway Elementary is under a mile away, the home is served by Coleytown Middle and Staples High, and Saugatuck's restaurants, downtown Westport and Compo Beach are minutes away. Homes this close to the train, with this much heart, rarely come to market.

3 Jonathan Ln, Westport

$2,999,999

5 Beds ⋅ 6 Baths ⋅ 24213615 MLS

Classic Colonial 5 Bedroom 5 - 1/2 Bath set on over 1 acre with a Gunite Swimming Pool on Westport's longest and perhaps, most sought after Cul-De-Sac! Almost 4700 sq ft on 1st & 2nd floors (hardwood flooring throughout), Plus 1400 sq ft in the fully finished, daylight, walk-out lower level. On the Main level the Gracious Living Room with Fireplace & Box Bay Window, is so large it easily accommodates the grand piano. Stroll through the Cocktail Lounge with built-ins, wet-bar & wine fridge to the delightful sunny, oversized Dining Room with dozens of windows & French Doors that lead to the rear deck. Circle back to the large Eat-In Kitchen with Island that seats four and a dedicated Dining Area by the Bay Window, this all seamlessly flows into the Family Room with Fireplace, Built-In Bookshelves and French Doors opening to the rear deck with views of the pool below. Rounding out the first floor are a Home Office, Ensuite Guest Bedroom with a Full Bath and Walk-In Closet, Half Bath in hall. The 2nd floor has an Enormous Primary Suite with Spa Bath, 3 Walk-In closets & Office or Dressing Room attached to the suite. The 2nd level has 3 more spacious family bedrooms, including one with an ensuite bath and walk-in closet and two more that have ample closet space and share a hall bath. The daylight, walkout lower level has a full bath, tv/media room, gym/playroom with sink, d/w, and fridge and a bonus storage room. Generac Generator! Walls freshly painted! Newer -Roof, HVAC, Septic!

14 High Point Rd, Westport

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Westport Real Estate

Newest Listings in Westport

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