Westport Homes for Sale

Welcome to Westport, Connecticut – a picturesque coastal town nestled in Fairfield County that beautifully blends suburban charm with vibrant cultural experiences. Known for its stunning waterfront views along the Long Island Sound, Westport is a haven for those seeking a serene lifestyle without sacrificing access to urban conveniences. With a rich history dating back to the 17th century, this town boasts a unique character, showcased through its historic buildings, artisanal shops, and thriving arts scene.

Westport is not just a visual delight; it also offers a plethora of outdoor activities. Residents can enjoy sun-soaked days at Compo Beach, explore the scenic trails of the Aspetuck Land Trust, or indulge in the local farmers’ market, celebrating the best of Connecticut’s produce. The town’s commitment to education is evident in its highly rated public schools, making it an ideal location for families.

For those considering a move, Westport's real estate market offers an array of homes for sale that cater to various tastes and budgets. From charming colonial-style houses to modern waterfront properties, there’s something for everyone. Each neighborhood reflects the town’s unique character, whether you prefer the bustling atmosphere of downtown or the tranquility of a quiet, tree-lined street.

With its idyllic setting, rich community spirit, and diverse housing options, Westport is more than just a place to live; it’s a lifestyle. Explore the homes for sale in this enchanting town and discover the perfect backdrop for your next chapter. Your dream home awaits in Westport, where every day feels like a vacation!

Newest Westport Homes for Sale

$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

$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

$1,525,000

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

$4,250,000

4 Beds ⋅ 4 Baths ⋅ 24213343 MLS

Tucked along a tranquil lane, mere steps from the soft sands of Westport's coveted Compo Beach, 19 Roosevelt Road is coastal living at its most refined. This picture-perfect residence of four bedrooms and three and a half baths pairs timeless elegance with effortless comfort. It was reimagined from the studs up in 2019 and is fully FEMA-compliant, with two light-filled levels and every modern convenience. On the main level, a gracious living room sets the tone, framed by custom built-in bookcases and warmed by a gas fireplace. The chef's kitchen is the heart of the home. It has a generous center island, a Sub-Zero refrigerator, a Wolf gas range and a dedicated wine refrigerator. Beyond it, a sun-drenched dining area flows into a step-down family room wrapped in windows, opening directly to the patio for seamless indoor-outdoor living. A private den or home office and an elegant powder room complete the floor. Upstairs are four bedrooms. The serene primary suite has its own balcony overlooking the professionally designed grounds. Three additional bedrooms of generous proportion share two beautifully appointed baths. Outside, lush gardens unfold around two stone patios, an enchanting setting for alfresco dining and summer entertaining. The home also includes a whole-house generator, a security system and irrigation. A new roof (2019), natural gas, city water and sewer complete the picture. An exceptional offering moments from the shore, ready to be enjoyed in every season.

19 Roosevelt Rd, Westport

$2,000,000

3 Beds ⋅ 3 Baths ⋅ 24213937 MLS

Tucked away at the end of a quiet cul-de-sac in Westport's desirable Charcoal Hill neighborhood, this beautiful one-level ranch offers the perfect blend of comfort, privacy, and easy living. Situated on 2.03 acres bordering a 7-acre land trust preserve, the home provides a peaceful setting with plenty of room to enjoy the outdoors. Thoughtfully updated throughout, the home features 3 bedrooms, 3 full bathrooms, and 2 additional flexible rooms. The bright, open layout includes a beautifully appointed kitchen with Bertazzoni appliances, Marvin windows, Kohler fixtures, and two wood-burning fireplaces. The primary suite opens to a private deck overlooking the property, while a covered deck offers a wonderful space for relaxing or entertaining. The spacious finished walk-out lower level provides additional living space, a full bathroom, and versatile rooms perfect for guests, home offices, or recreation. Additional features include a 2-car garage, high-efficiency HVAC, and smart-home technology. Conveniently located just half a mile from Coleytown schools, with easy access to the Merritt Parkway and downtown Westport. A wonderful opportunity to enjoy comfortable, move-in-ready living in a private and convenient Westport location.

2 Charcoal Ln, Westport

$2,795,000

5 Beds ⋅ 4 Baths ⋅ 24213304 MLS

Lovingly cherished by the same family for over 50 years, this 1965 five bedroom home presents a wonderful opportunity to create something truly special in one of Westport's most desirable neighborhoods. Ideally situated within walking distance to the water and train, the location offers the perfect blend of coastal charm, convenience, and community. Recent updates, including fresh interior paint, refinished or new hardwood flooring, provide a refreshed starting point, while the home's abundant potential invites you to bring your vision to life. Whether you choose to thoughtfully renovate, reimagine, or create your dream home, this is a rare chance to invest in a property with a special history and an exceptional setting on a quiet street near Longshore Club Park. This treasured property is ready for its next chapter, just moments from everything that makes Westport living so special.

4 Surrey Ln, Westport

$2,950,000

5 Beds ⋅ 6 Baths ⋅ 24212624 MLS

A rare opportunity to own an exceptional woodland estate, where space, serenity, and natural beauty converge. Set beyond a long, gracefully winding driveway, this expansive residence is surrounded by mature trees, creating a remarkable sense of arrival and seclusion. Thoughtfully suited for multigenerational living, the home features a separate wing offering flexibility for extended family, an in-law suite, or long-term guests, allowing for both privacy and connection under one roof. Generous living spaces provide an ideal setting for sophisticated entertaining and relaxed everyday living, while tranquil woodland views create a peaceful backdrop throughout the seasons. Outdoors, a stunning natural gunite pool offers a private, resort-like oasis, beautifully integrated into the wooded landscape and perfect for summer entertaining and relaxation. Combining versatile living arrangements, exceptional space, and a truly serene setting, this distinctive property offers a rare opportunity to experience the best of private estate living. Pre-inspection items have been completed and repaired, providing added peace of mind for the next owner.

142 Easton Rd, Westport

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Westport Homes for Sale

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