Westport Real Estate

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

$2,195,000
4 Beds ⋅ 3 Baths ⋅ 24205784 MLS
Experience modern coastal luxury in this custom-built, down-to-the-studs NEW CONSTRUCTION just minutes from Compo Beach and downtown Westport. Blending the scale and sophistication of a true custom home with effortless single-level living, this exceptional property showcases designer finishes and impeccable craftsmanship throughout. The sun-filled open floor plan features soaring cathedral ceilings, white oak floors, custom millwork, Marvin windows, and a striking porcelain fireplace. The chef's kitchen features custom cabinetry, premium Calacatta porcelain countertops, full-height backsplash, oversized island, and matching wet bar, complete with a dual-zone wine refrigerator, beverage cooler, and ice maker. Top-of-the-line Bosch appliances complete this exceptional space, designed for both everyday living and entertaining. Expansive tri-fold doors open to a spacious deck overlooking private, fully fenced backyard with professional landscaping. The main-level primary suite offers heated bathroom floors, automated blinds, and spa-inspired finishes. The finished lower level includes a gym or recreation room, five-person infrared sauna, wine room, full bath, laundry room with GE appliances, and abundant storage. Additional highlights include smart home technology, integrated sound, a Tesla Universal EV charger, and an epoxy-finished garage. This is not just an extraordinary home, it's a spectacular lifestyle offering every amenity imaginable in a coveted location.

2 Drumlin Rd, Westport
$539,000
1 Beds ⋅ 1 Baths ⋅ 24205418 MLS ⋅ Westport Village BLDG.
Welcome to this charming condominium featuring a bright, open concept layout designed for comfortable living and effortless entertaining. The spacious living and dining area flows seamlessly into the kitchen, creating an inviting atmosphere filled with natural light.The generously sized bedroom offers a peaceful retreat, while the well appointed bathroom provides both style and functionality. Step outside to your private patio, perfect for enjoying your morning coffee, relaxing with a book, or dining al fresco. Whether you are a first time buyer, looking to downsize, or searching for a low maintenance home, this condominium offers the perfect blend of comfort, convenience, and modern living in a great location in Westport.

12 Cross Hwy Unit B, Westport
$999,000
3 Beds ⋅ 3 Baths ⋅ 24196339 MLS
An incredible opportunity has become available in a prime Westport, CT location. Set off the road on a quiet turnoff at the corner of the Overlook cul-de-sac, this expanded Cape on 0.52+/- acre of enchanting property is ready for your creative vision. This is the only 3 bedroom, 3 full bathroom home available in Westport below $1,649,000 - making this a spectacular chance to add value by updating, remodeling, expanding, or building new construction within moments of downtown, train, the Merritt Parkway, I-95, the Y, & schools. This quintessential New England Cape Cod-style home begins with a larger than expected foyer/center hall. The large living room has the first fireplace, built-ins, and French doors leading to the distinctive family room with a custom-patterned hardwood floor, stone fireplace and bookshelves. Formal dining room for entertaining. The kitchen was remodeled w/quality cabinetry and beautiful granite counters, top appliances including Sub Zero, and leads to the vltd ceiling breakfast room with skylights & glass doors facing both front & back. Private office/bonus room/playroom lined with built-ins. The first of the 3 BRs is on the main level, with built-ins and an adjacent full bath. Upstairs, the 2nd BR has its own full bath and the primary suite is an incredible surprise, with king-size BR, oversized lux-scale bathroom & walk-in clst. Partially fin LL. Patios & charming garden paths add to the character. This home requires work and is being sold-as is.

183 Wilton Rd, Westport
$220,000
24205902 MLS
A Rare Opportunity to Bring Your Culinary Vision to Life Step into a charming, intimate Italian restaurant with the kind of atmosphere you can't manufacture - cozy, welcoming, and full of character. This is the perfect canvas for a chef-owner or passionate foodie who dreams of creating unforgettable meals in a place that truly feels their own. The restaurant is fully equipped, thoughtfully laid out, and designed for comfort and connection. It's the kind of dining room where regulars get to know your name, where families celebrate milestones, and where great food is paired with genuine hospitality. Whether your dream is rustic Mediterranian comfort cuisine, regionally inspired specials, or a chef-driven tasting menu, this space is ready for your imagination - and your recipes. Instead of spending years building from scratch, you can step into an established setting and start cooking the food you love, for people who will truly appreciate it. If you've ever said, "One day I want my own place," - this could be that day.

Post Rd Rd, Westport
$1,890,000
4 Beds ⋅ 4 Baths ⋅ 24205323 MLS
Welcome to Northfield Drive, a street in a highly sought after neighborhood, with walking paths to both the elementary and middle schools. This spacious and inviting home is set on a stunning park-like, flat, dry acre. Approx. 3,174 square feet of living space across three levels, plus a full basement, this 11-room home features 4/5 bedrooms and 4 full baths. Kitchen has been updated with quartz counters, Wolf stove and a Sub-Zero refrigerator. Designed for both comfortable everyday living and effortless entertaining, the home features an open floor plan, hardwood floors throughout the first and second levels, vaulted ceilings and walls of windows that fill the interiors with natural light and bring the beauty of the outdoors in. A true highlight is the spectacular family room, with its soaring vaulted ceiling, abundant windows and custom built-ins...an inviting space to enjoy throughout the seasons. The primary suite offers a spa-like retreat with a steam shower, Jacuzzi tub, double sinks and high-end fixtures. The full basement provides wonderful bonus space for a home gym, game room, recreation area or additional storage, while a walk-up attic offers even more versatility. Spacious garage w/EV charger. With generous living spaces, wonderful natural light and an exceptional one-acre setting, this Coleytown home offers the space and flexibility to live, work and entertain with ease-all in one of Westport's most sought-after neighborhoods.

5 Northfield Dr, Westport
$4,750,000
5 Beds ⋅ 7 Baths ⋅ 24204438 MLS
A fresh take on Modern Luxury awaits at this new construction home set on stunning property in the Old Hill area of Westport. Now complete and ready for immediate enjoyment, this dynamic residence is perfectly located for convenience to commuting, the train station, schools, shopping and more. Exhilarating architecture will awaken your senses as you approach this customquality home. Walls of glass blend the natural setting with stunning interiors, and bring sunlight deep into the spectacular rooms. The chef's kitchen is a showpiece, featuring bespoke oak cabinetry, premium finishes, and a substantial walkin pantry. Dual mainlevel offices support today's lifestyle. 5 spacious bedrooms and 7 refined baths create a harmonious balance of comfort and sophistication. The primary suite is a serene retreat with three fitted closets and a spalevel ambiance. Additional bedrooms offer generous scale and thoughtful design. A sunlit upstairs lounge and a finished thirdfloor space provide flexible areas for work, play, or creativity. The finished lower level offers exceptional spaces for fitness, media, or entertaining. Outside, an expansive patio overlooks 1.68 acres of private grounds, ideal for gatherings or quiet reflection. A 3car garage (with a separate bay for a trophy vehicle or storage) and sleek modern detailing complete this remarkable offering. An inspired blend of architecture, setting, and convenience await in a prime location. Pool permit in place.

1 Twin Oaks Ln, Westport
$2,650,000
3 Beds ⋅ 3 Baths ⋅ 24203635 MLS
Impeccable, effortlessly sophisticated house with lovely water views nestled on private road in idyllic Saugatuck Shores steps to Long Island Sound and Bermuda Lagoon. Designed by top architect VITA Design, the house combines relaxed coastal luxury with an elevated contemporary aesthetic for easy living, enjoyable year round. Features warm beach-inspired woods, high-end finishes, high ceilings, light wood floors, oversized windows and abundant natural light. On the main level the sleek chefs kitchen w/ center island flows seamlessly into the dining area and great room w/ wood-burning fireplace framed by floor-to-ceiling windows. Office/bedroom and full bath complete the main level. Second floor features serene primary suite with water view, custom built-ins and luxurious bath. Two additional bedrooms, full bath, laundry, and stylish reading nook complete this level. The front to back top floor bonus room with water views on both sides, leads out to spectacular roof deck terrace with view of Long Island Sound --a wonderful outdoor living space perfect for entertaining or quiet enjoyment to take in glorious sunsets, sunrises and Fourth of July fireworks over the Sound. The lower level offers additional versatile rec room, mudroom, attached garage. Private back yard. House is FEMA compliant. Lovely neighborhood for walking, biking, boating, kayaking. Close golf/tennis. Quick drive to the train station, Saugatuck shops and dining, and all Westport has to offer.

14 Promised Rd, Westport
$1,599,000
3 Beds ⋅ 3 Baths ⋅ 24204054 MLS
In-town living at its best! Step into a little piece of history with this charming three-bedroom, 2 1/2-bath home, beautifully renovated and situated in Evergreen's historic district just moments from Main Street. Light and airy throughout, this home offers an inviting open floor plan with a warm comfortable feel. The newer kitchen opens seamlessly to a spacious great room with relaxed living and dining areas, anchored by a cozy fireplace; an ideal setting for everyday living and entertaining. Enjoy generous outdoor spaces, including a large deck and stone patio. The private yard provides a wonderful spot to garden, unwind, or savor a cup of coffee. A true condo alternative without giving up privacy, outdoor space, or the appeal of a single-family home. This property is so conveniently located near Westport's Main Street shopping, Compo Beach, Metro-North, and major highways. Part of Westport's history, this timeless home is ready for you to begin its next chapter! Not to be missed!!

2 Evergreen Ave, Westport
$1,325,000
2 Beds ⋅ 4 Baths ⋅ 24204033 MLS ⋅ Harvest Commons BLDG.
Nestled in a prime location within a beautifully maintained complex, this exceptional home offers access to premier community amenities-including a pool and tennis courts-alongside the luxury of your own completely private patio. Harvest Commons is ideally situated just moments from fine dining, local shopping, and the Greens Farms train station. Inside, the elegant formal living room features soaring vaulted ceilings, large windows, a cozy wood-burning fireplace, and sliding glass doors that open seamlessly to the outdoors. The main level also boasts a full formal dining room-a rare feature not found in all models-and an exceptionally spacious kitchen and family room combination with a impressive wall of glass and convenient direct access to the attached two-car garage. Upstairs, the expansive primary suite serves as a peaceful retreat, complete with vaulted ceilings, two generous walk-in closets, and an en-suite bath with both a soaking tub and separate shower. A second well-appointed bedroom, a separate full bath, and a dedicated second-floor laundry room complete the upper level. The finished lower level provides versatile additional living space ideal for a recreation room, home office, or guest quarters, along with a rare third full bathroom. Seller would like a January closing.

124 Harvest Commons Unit 124, Westport
$9,860,000
6 Beds ⋅ 9 Baths ⋅ 24205443 MLS
Newly completed, this exceptional modern estate offers approximately 9,200 square feet on 2.1 private acres just minutes from downtown Westport, Compo Beach, and Metro-North. Thoughtfully designed with European craftsmanship, premium finishes, and sophisticated smart-home technology, the home blends timeless design with exceptional functionality. A dramatic floating staircase anchors four finished levels featuring soaring ceilings, custom millwork, and engineered white oak flooring. The chef's kitchen showcases dual quartzite waterfall islands, custom rift white oak cabinetry, a walk-in pantry, and a professional appliance suite. The primary suite offers cathedral ceilings, a fireplace, private balcony, dual dressing rooms, and a spa-inspired bath with heated floors and a soaking tub. Designed for seamless indoor-outdoor living, the nearly 950-square-foot covered terrace features granite flooring, a wood-burning fireplace, outdoor kitchen, heated 20' 40' saltwater pool, 10-person spa, and room for a future tennis or pickleball court. The walk-out lower level includes a family room, wet bar, fitness studio, guest suite, and flexible space for a theater, golf simulator, or media lounge. Prepare to fall in love.

9 Over Rock Ln, Westport
$5,495,000
6 Beds ⋅ 9 Baths ⋅ 24203359 MLS
Located within the highly desirable Stony Point Association, this exceptional home offers a rare combination of privacy and convenience just moments from the train, local restaurants, and everyday amenities. This particular home enjoys private dock membership, providing summer boat access just steps from your door. Completely transformed and expanded in 2016, the home features over 6,500sf of thoughtfully designed living space, including 6 bedrooms and 9 baths. Expansive panoramic windows capture seasonal water views and fill the home with natural light. A dramatic two-story entry foyer and soaring ceilings create an impressive sense of space. The open-concept kitchen/living room is a true centerpiece, featuring a massive 12-foot island with seating for 6, high-end appliances, dual dishwashers, a wine fridge, an ice maker - ideal for both everyday living and entertaining. Designed for effortless indoor-outdoor living, the home seamlessly connects its interior to exceptional outdoor entertaining areas. The spacious family room features sliders that open directly to the expansive covered patio with retractable screens, an outdoor kitchen, and a relaxing pool and spa. The 3rd floor great room has amazing water views, and features a 1/2 bath and wet bar. Additional highlights include a private office, whole house generator, 2 laundry rooms, sauna, mudroom, and a charming 'hidden' playroom. A truly turnkey offering.

3 Stony Point W, Westport
$675,000
2 Beds ⋅ 3 Baths ⋅ 24203810 MLS ⋅ Strathmore Lane BLDG.
Move right in to this newly-fully-updated-in-2025 end-unit townhouse offering a fresh, stylish interior and an exceptional location. A brand-NEW kitchen anchors the open-concept main level, creating an inviting flow for everyday living and entertaining. The home features 2 1/2 NEW updated baths, all-NEW HVAC systems and NEW hot water heater, new paint throughout, and two fireplaces that add warmth and character. As an end unit, the home enjoys added privacy: step outside to a pretty, private patio overlooking mature trees and greenery, a peaceful setting for morning coffee, outdoor dining or simply relaxing. $7,000 investment made in new Hunter Douglas blinds throughout. Westport's train station is just a short walk away, along with the restaurants, cafes and the vibrant atmosphere of Westport's Saugatuck neighborhood. The property has a Westport address while enjoying Norwalk amenities. Beautifully updated, exceptionally convenient and ready to enjoy, this is easy living at its best.

12 Strathmore Ln Unit 12, Westport
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