Westport Homes for Sale

Welcome to Westport, Connecticut – a charming coastal town nestled in the heart of Fairfield County. Known for its picturesque landscapes and vibrant community, Westport offers a unique blend of suburban tranquility and urban amenities. With its stunning waterfront views along Long Island Sound, residents can enjoy an array of outdoor activities, from sailing and kayaking to leisurely strolls on the beach. The town is also rich in culture, boasting a thriving arts scene, top-rated schools, and an array of dining and shopping options.

For those considering a move to this idyllic locale, Westport's real estate market is brimming with opportunity. Homes for sale in Westport range from charming historic properties to modern masterpieces, catering to a variety of tastes and lifestyles. Whether you're seeking a cozy cottage near the water or a spacious family home with expansive gardens, Westport has something to suit everyone.

The community is known for its friendly atmosphere and strong sense of belonging, making it an ideal place for families, professionals, and retirees alike. With excellent public transportation options, including easy access to Metro-North trains, commuting to New York City is a breeze, allowing residents to enjoy the best of both worlds – serene suburban living and the vibrant energy of the city.

Explore our listings today and discover your dream home in Westport, where charming neighborhoods, beautiful parks, and a welcoming community await you. Embrace the Westport lifestyle – where every day feels like a vacation!

Newest Westport Homes for Sale

$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

$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

$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

$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

$1,649,000

4 Beds ⋅ 3 Baths ⋅ 24201214 MLS

Set on a private flat half acre and thoughtfully expanded and beautifully maintained, this move-in-ready 4 bedroom home offers a flexible floor plan designed for today's lifestyle, with exceptional space for work, entertaining, and relaxation. Enter to a wonderful sun filled living room with fireplace, a new renovated kitchen with large island and stainless steel appliances and separate dining area. Adjacent to the kitchen is a sun filled great room with vaulted ceilings that opens to a generous stone patio-perfect for endless entertaining inside and out. Finished across four levels, the home offers a wonderful blend of comfort and privacy. The spacious primary suite occupies its own private floor and features vaulted ceilings, a walk-in closet, and a luxurious bath. An adjacent oversized room provides the perfect retreat for a home office, gym, or additional living space. 3 additional bedrooms share another large bath. The finished lower level offers even more versatility, with a separate entrance, mudroom/laundry room, full bath, and a flexible playroom, family room, or second home office. Outside, the level, fully fenced yard provides plenty of room for play, pets, gardening, and entertaining. With its exceptional location, thoughtfully designed spaces, and inviting indoor-outdoor living, 104 Old Road is a wonderful opportunity to enjoy all that Westport has to offer-close to town, schools, shopping, & just minutes from the Greens Farms train station.

104 Old Rd, Westport

$899,000

2 Beds ⋅ 2 Baths ⋅ 24204656 MLS

Welcome to 1 Maplewood Avenue-Your Opportunity to Call Westport Home! Charming, stylish, and filled with possibilities, this inviting **2-3 bedroom Westport home** offers an exceptional opportunity to enjoy one of Fairfield County's most desirable communities and its **highly regarded school system**. Step inside to discover **beautifully refinished hardwood floors** and a bright, comfortable floor plan designed for today's lifestyle. The **updated kitchen features stainless steel appliances**, while refreshed **tile bathrooms** add a clean, modern touch. Need more room? You'll love the versatility of the **finished walk-up attic**, perfect for a home office, creative studio, guest space, or additional retreat. A separate **playroom** provides even more flexibility for recreation, entertaining, or everyday living. Situated on a corner lot with generous parking, the property offers space, convenience, and plenty of potential to make it your own. Whether you're purchasing your **first home, downsizing, or looking for an exciting opportunity to enter the Westport market**, 1 Maplewood Avenue delivers the perfect combination of charm, updates, flexible living space, and location. Westport living may be more attainable than you think-come discover the possibilities at 1 Maplewood Avenue!

1 Maplewood Ave, Westport

$4,600,000

6 Beds ⋅ 8 Baths ⋅ 24204809 MLS

Resort-style living meets modern luxury at 2 Windy Hill Road. Set on a private landscaped acre, this newly completed 8,100+ SF estate by HOBI Award-winning builder Cypress Development was thoughtfully designed for the way today's luxury buyer lives, entertains, and unwinds. A dramatic two-story foyer introduces light-filled interiors highlighted by soaring ceilings, white oak flooring, natural stone finishes, and walls of European windows and doors. At the heart of the home, the chef's kitchen features marble countertops and backsplash, Sub-Zero and Wolf appliances, custom oak cabinetry, dual dishwashers, and a stunning waterfall island that seamlessly connects to the home's gathering spaces. The primary suite serves as a private retreat with vaulted oak-beamed ceilings, fireplace, sitting area, private balcony overlooking the pool, custom dressing room, and spa-like bath with heated floors and dual showers. Designed for both entertaining and wellness, the lower level includes a glass-enclosed gym, custom marble-topped bar, recreation space, guest suite, and a dedicated area ready for a golf simulator or theater. Outside, enjoy a gunite pool with automatic cover, covered outdoor living area, expansive granite patios, outdoor kitchen provisions, and a large flat lawn surrounded by mature landscaping, stone walls, and privacy plantings. A rare offering that delivers the comfort of everyday living with the amenities of a private resort.

2 Windy Hill Rd, Westport

$3,400,000

5 Beds ⋅ 5 Baths ⋅ 24204780 MLS

This beautifully renovated Ward French custom home offers elegant formal spaces, a chef's kitchen, flexible guest and office accommodations, a luxury primary suite, fitness studio and sitting room with balcony. The home's 2,442 square foot lower level offers tremendous untapped potential, providing an opportunity to create customized luxury amenities such as a home theater, golf simulator, wine cellar, wellness spa, or guest retreat. Outdoors a spectacular 20' x 40' pool and spa, multiple entertaining patios, and lush private landscaping create a true retreat. Moments from schools and town amenities, this exceptional Westport residence perfectly balances luxury and everyday living.

27 Woody Ln, Westport

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.