Refine Search
Map
Sort by
238 Hillspoint Rd, Westport
$4,995,000
3 Beds ⋅ 4 Baths ⋅ 24194201 MLS
The dream of waterfront living is officially taking shape-construction is underway by renowned builder The O'Dell Group. This is your chance to secure a front-row seat to the Long Island Sound on one of Westport's most prestigious stretches of coastline. This exceptional property offers direct water frontage + sweeping, uninterrupted views of the Sound + the iconic Old Mill Beach. Imagine waking up to the soft glow of a sunrise over the water, spending your afternoons enjoying the refreshing salt air, or relaxing to the rhythm of the tide. Every detail of this build is designed to maximize the connection to the sea, offering a lifestyle defined by beauty + tranquility. Nestled in a welcoming and picturesque community, you'll enjoy access to top-ranked schools + Westport's vibrant downtown, known for its exceptional dining, shopping, and cultural experiences. Plus, the location is ideal for commuters, with close proximity to Metro-North for a seamless trip to Grand Central Station in NYC. As the last available parcel of its kind for development in this coveted location, this project represents a rare opportunity to own a brand-new architectural masterpiece in an idyllic setting. With The O'Dell Group's signature craftsmanship now in motion, the vision for this ultimate beach house is becoming a reality. Seize the opportunity to claim this piece of paradise and personalize your finishing touches while there is still time. Reach out today to make this coastal sanctuary your own.

238 Hillspoint Rd, Westport
1 Coastal Ct, Westport
$4,995,000
5 Beds ⋅ 7 Baths ⋅ 24126503 MLS
Introducing 1 Coastal Court, a rare opportunity to own in Westport's only gated community, an exclusive four-lot enclave envisioned and built by Joe Feinleib, founder of Coastal Luxury Homes and one of Fairfield County's most respected builders.This private neighborhood blends timeless architecture with modern luxury. Each custom residence, ranging from 5,000 to 7,500 square feet, plus generous garages, balconies, patios and covered porches, will be designed in collaboration with the homeowner - ensuring every detail reflects your vision. Expansive layouts, pool sites, and inviting outdoor living spaces create the perfect setting for today's lifestyle, balancing sophistication with everyday comforts. Working with Coastal Luxury Homes is a dynamic, collaborative and easeful process with every detail curated to suit the homeowners' vision of the perfect home. Whether you dream of having your own golf simulator, outdoor chef's kitchen, sauna or elevator...everything is possible. Ideally located just moments from Westport's award-winning schools, vibrant downtown, the train, and Compo Beach, this unique neighborhood offers a rare combination of privacy and convenience. Mature landscaping and thoughtful design create a serene retreat, while the best of dining, shopping, and recreation are just minutes away. This is more than a new home - it's the chance to create your dream residence with an award-winning builder in a community unlike any other in Westport.

1 Coastal Ct, Westport
22 Evergreen Ave, Westport
$4,850,000
5 Beds ⋅ 5 Baths ⋅ 24172211 MLS
Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate where classic Arts & Crafts architecture meets the tranquility of a private countryside retreat. Set on over 2.5+ sprawling acres of pristine grounds, this exceptional 5 Bed, 5 Bath residence offers more than 5,100 sqft of refined living, surrounded by natural beauty & complete privacy. From the moment you arrive down the private, meandering drive framed by mature landscaping; The Winslow Manor evokes a sense of warmth, character, and enduring craftsmanship. Rich architectural details, beamed ceilings, inviting living spaces, & thoughtfully designed interiors create a home that feels both grand and deeply welcoming- as if stepping into a piece of cozy history, carefully preserved and elevated for modern living. Designed for both relaxation & recreation, the estate unfolds into an extraordinary outdoor experience. A sparkling Gunite pool, multiple terraces, Pergolas, & dedicated home gym create the ultimate summer retreat, while the surrounding pond and protected wetlands attract an abundance of wildlife, offering peaceful views and a connection to nature rarely found so close town.

22 Evergreen Ave, Westport
2 Windy Hill Rd, 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
1 Twin Oaks Ln, Westport
$4,550,000
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
159 Easton Rd, Westport
$4,450,000
6 Beds ⋅ 8 Baths ⋅ 24145772 MLS
Are you dreaming of an estate property? Something a bit more than the generic flat acre on a cul de sac? How do two acres on the Aspetuck River sound to you? With views from your bedroom? The sounds of a waterfall next door lulling you to sleep? Having sunnies tickle your toes in the summertime? Maybe a bit of fly fishing for trout? Or perhaps some paddleboarding? Yes, of course, there's a 20x40 salt water pool, but . . the river - wow! Welcome to the latest offering from CCO Habitats - a new construction home with over 8300 sf of finished space on 3 floors. A floorplan you will love, with not only 2 designated offices, but a private first floor bedroom as well. Organic, modern, warm and inviting, with a calming palette sure to blend with and 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 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. It's all here; only a mile from the award-winning Coleytown schools. This is the one you've been waiting for. Unique. Special. Just like you. :)

159 Easton Rd, Westport
191 Bayberry Ln, Westport
$4,299,000
5 Beds ⋅ 5 Baths ⋅ 24212297 MLS
Welcome to BAYBERRY FARMS- a refined oasis of style, comfort and custom amenities begins to unfold upon arrival at this property in an area known for fine estates. A gated drive welcomes you home, first to an ample motor court and then you will pass through carefully landscaped gardens. Inside, the creative and energetic spirit of this home begins to reveal the array of quality features that define it. Sensitively blending the character of a country retreat w/bold modern vision, this 5-BR residence was completely reimagined in 2025. The large living room w/built-ins, bay window & fpl is ideal for grand entertaining. The large sunroom/office is lined w/windows & glass doors. The gourmet kitchen has custom exotic wood cabinetry, Viking appliances & a breakfast area with a folding glass wall that leads to the pool terrace. The DR has a wall of glass, unique corner fpl & original built-ins. The family rm has a modern fpl feature wall & large-scale space for any gathering. Flexible layout w/2nd sunny office. A bonus area over the garage has an incredible game room & gym. The primary ste is an incredible retreat- you will not find another like it. This five-star space has an amazing glass-lined bedroom, two custom walk-in dressing rms w/full glass-fronted built-ins, & a stunning bath w/massive glass shower, soaking tub & more. The rear property rivals boutique hotels w/very large stone terrace, full summer kitchen w/pizza oven, gunite pool w/auto cover, hot tub, porch, garden

191 Bayberry Ln, Westport
19 Roosevelt 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
6 Janson Dr, Westport
$4,250,000
6 Beds ⋅ 9 Baths ⋅ 24165540 MLS
Exceptional new construction by AR Luxury Homes with 7,500+/- square feet of thoughtfully designed living space across four finished levels in a prime Westport location. This 6-bedroom, 6 full and 3 half bath residence blends refined craftsmanship with modern functionality, featuring an open-concept layout ideal for both everyday living and entertaining. The heart of the home is a custom-designed kitchen equipped with premium appliances including Wolf and Sub-Zero, expansive island, and seamless flow to the family room with fireplace. Three fireplaces throughout the home add warmth and architectural interest. White oak flooring, custom millwork, and high-end finishes elevate every space. The upper levels offer a luxurious primary suite with spa-like bath and custom closet, along with well-appointed secondary bedrooms. A fully finished lower level with walkout access provides flexible space for recreation, fitness, or additional living. Set on a level .50-acre property, the outdoor experience is complete with a 15' x 30' heated gunite pool, bluestone patio, and professionally planned landscaping-perfect for enjoyment and relaxation. Additional features include city water and sewer, propane gas, 400-amp electrical service, 24 KW generator, and wiring for audio, security, and smart home systems. A rare opportunity to own a new construction home with exceptional scale, quality, and amenities. Still time to customize finishes.

6 Janson Dr, Westport
11 Woodside Ln, Westport
$4,050,000
5 Beds ⋅ 6 Baths ⋅ 24211806 MLS
Privately set in Westport's coveted Old Hill neighborhood, this like-new sophisticated residence designed by famed architect Peter Wormser pairs striking architecture with timeless, understated elegance. Soaring ceilings, beautifully curated spaces and abundant natural light define the stylish interiors, creating a home that is at once impressive and inviting. 4 finished levels provide exceptional space for everyday living, entertaining, work and guests. The primary suite stuns with its 20-foot ceilings, fireplace, 2 walk-in closets and spa bath. 4 additional bedrooms each feature walk-in closets, while 2 private offices offer dedicated work-from-home space. A 3rd-floor recreation room with full bath adds more flexibility, while the beautifully finished lower level has a home theater, gym, space for play, plus storage. Outdoors, the magical setting unfolds through multiple entertaining spaces, from inviting covered porches to an expansive stone patio with a fully-equipped outdoor kitchen, built-in grill and Big Green Egg, offering an exceptional backdrop for gatherings large and small. Lush, established landscaping creates a remarkable sense of privacy, yet the home is just over a mile to Westport's vibrant downtown. Whole-house generator, solar and level 2 EV charger! The NYC-bound train is just 9 minutes away. Distinctive, sophisticated and effortlessly livable, this exceptional Old Hill residence is a rare offering of inspired architecture, privacy and a prime location.

11 Woodside Ln, Westport
61 Clapboard Hill Rd, Westport
$3,698,000
4 Beds ⋅ 4 Baths ⋅ 24205877 MLS
Located in prestigious Greens Farms, this European-inspired Colonial offers a rare opportunity to enjoy immediate charm while planning for the future. Set behind private gates on expansive, picturesque grounds, the property is surrounded by multimillion-dollar estates-making it an exceptional canvas for new construction or a significant estate expansion. The existing home is beautifully renovated, offering flexibility with gracious living and dining rooms, a sun-filled sunroom, cozy family room, and a curated Chef's kitchen with Calacatta marble, bespoke cabinetry, and top-tier appliances. A serene Primary Suite and additional bedrooms upstairs, the home functions perfectly as-is-or as a future guest house or accessory residence with thoughtful modifications. The sweeping land provides ample room for a new main residence set further back on the property, while altering the current home for extended family, guests, staff, or as a pool house. Outdoor living is equally compelling, with an expansive covered stone terrace, fire pit, and open meadow-like grounds offering endless possibilities for a pool, tennis court, barn, or gardens. Whether you choose to embrace the home's timeless appeal or create a legacy estate tailored to your vision, this is a unique chance to live comfortably now while building for tomorrow-all in one of Westport's most coveted locations, just minutes to Westport's vibrant downtown with award winning restaurants, premium shopping, beaches, and train.

61 Clapboard Hill Rd, Westport
9 Berkeley Rd, Westport
$3,695,000
5 Beds ⋅ 5 Baths ⋅ 24209539 MLS
Exceptional new construction, 9 Berkeley Road presents a sophisticated interpretation of modern Westport living, blending timeless architecture with beautifully considered spaces and an exceptional floor plan. Gracious proportions, abundant natural light and 9-foot ceilings create an immediate sense of understated luxury throughout the main level. At the heart of the home, an expansive chef's kitchen with separate scullery and breakfast area opens seamlessly to a stunning family room accented by oak ceiling beams. Formal living and dining rooms provide elegant settings for entertaining, while a private home office offers a quiet retreat. A beautifully designed first-floor guest suite with full bath and walk-in closet provides privacy and flexibility for family and guests. Expansive doors extend the living spaces outdoors to a generous rear deck, complemented by a bluestone-covered porch for effortless indoor-outdoor entertaining. Upstairs, the luxurious primary suite is a private sanctuary featuring a spacious bedroom, dressing area, walk-in closet and beautifully proportioned bath. Three additional bedrooms, multiple baths, generous closets, a dedicated laundry room and loft complete the second level. Sophisticated yet inviting, and an exceptional opportunity to own a thoughtfully designed new residence where elevated style, modern luxury and effortless livability come together in one of Westport's most desirable settings. *REPRESENTAIVE IMAGES* Agent/owner

9 Berkeley Rd, Westport
9 N Ridge Rd, Westport
$3,400,000
6 Beds ⋅ 7 Baths ⋅ 24208426 MLS
In today's world, there is nothing more important than having a place to gather. This private retreat with a stunning residence and amazing recreational facilities can become your own private sanctuary with a tennis court, heated Gunite pool and separate pool house set among lush, meticulously curated grounds on almost 2.4 acres. This 6,700-square-foot shingle-style residence offers refined luxury across three expansive levels, combining architectural sophistication with a warm sense of livable comfort. The main level flows beautifully and showcases dramatic interiors with large gathering spaces, gourmet kitchen facilities and incredible entertaining capabilities. The main floor primary suite serves as a luxurious private retreat with his and her bathrooms and separate sitting room/office. Upstairs, three additional bedrooms continue the home's commitment to comfort and privacy. The finished lower level extends the home's appeal with numerous recreational spaces and a full bath. Beyond the impressive interiors, the grounds are truly breathtaking. A rhythm of blooming flowers and mature landscaping creates a sense of beauty throughout all four seasons, thoughtfully designed to offer year-round color and serenity. Located on a private cul-de-sac, this home is a true compound-balanced, gracious, and masterfully executed, offering unparalleled living inside and out. Once you have arrived, it will be hard to leave!

9 N Ridge Rd, Westport
4 Turkey Hill Ln, Westport
$3,295,000
5 Beds ⋅ 5 Baths ⋅ 24212748 MLS
Turnkey 2013 Contemporary Oasis | 5 Beds | Pool | Prime Westport Flawless execution meets ultimate convenience at 4 Turkey Hill Lane. Built in 2013 and meticulously maintained, this 5,318sqft. contemporary offers the ultimate turnkey experience in Westport's highly sought-after Long Lots neighborhood. The Interiors: An open-concept, light-filled layout designed for modern living. The centerpiece is a spectacular 2-story great room with a floor-to-ceiling stone fireplace. The seamless flow leads right into a high-end chef's kitchen featuring Sub-Zero appliances, double wall ovens, a wine chiller, and a massive walk-in pantry. Upstairs, the primary suite delivers with dual walk-in closets, a luxe en-suite, and a private balcony. Three additional upper-level bedrooms feature smart Jack-and-Jill setups, while a massive third-floor rec room handles everything from billiards to a home gym. The Grounds: 1.07 level acres of unparalleled outdoor living. Highlights include a heated gunite pool & spa, custom stone patio with pergola, and an outdoor stone fireplace. Beyond the pool, the expansive flat lawn rolls gently down to a private brook. Solar, a 3-car attached garage, and city utilities ensure effortless homeownership. Enjoy privacy without sacrificing convenience-you are just minutes from Westport's downtown dining, high-end retail, beaches, and the Metro-North station. Note: Listing Agent is related to a principal/member of the selling entity.

4 Turkey Hill Ln, Westport
14 High Point Rd, 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
142 Easton Rd, 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
79 Riverside Ave, Westport
$2,895,000
3 Beds ⋅ 4 Baths ⋅ 24211839 MLS
A masterclass in modern coastal architecture, this four-level waterfront retreat delivers a seamless connection to the Saugatuck River. Floor-to-ceiling glass anchors the open-concept main floor, filling it with natural light and showcasing broad river views. Recent high-end infrastructure and tech upgrades make the home as smart as it is stylish--featuring custom Lutron automated window shades throughout, a fully integrated audio/video system, custom window and retractable door screens, and EV charger pre-wiring. Outdoors, enjoy an automatic irrigation system, a conservation-approved custom wire and rail fence, and dock approvals nearing completion, clearing the path to launch your boat into Long Island Sound. An adjacent park further preserves the home's scenic setting and surrounding privacy. Spanning 1,841 intelligently planned square feet, the layout offers ideal space separation and turn-key, lock-and-go convenience: a private second-floor primary suite with walk-in closet and en suite bathroom with tub and steam shower, a third-floor guest suite with a private balcony, and a lower-level family room next to a third bedroom with ensuite bathroom and walk-in closet. Just outside, a water's edge terrace offers effortless riverfront entertaining--all in a prime Westport setting moments from downtown, offering immediate access to local dining, shops and parks.

79 Riverside Ave, Westport
4 Bradley St, Westport
$2,885,000
5 Beds ⋅ 4 Baths ⋅ 24209324 MLS
Just 383 steps from the sands of Compo Beach, this storied 1920s residence claims one of Westport's most sought-after addresses. Approximately 3,255 square feet hold five bedrooms and four baths. An open, updated kitchen with top-tier appliances flows into the living and gathering areas. The primary suite is a generous retreat with vaulted ceilings, a spa bath, and a walk-in closet. Four additional bedrooms are ample in scale - one en-suite, with a Jack-and-Jill bath connecting two others - while a full bath and a dedicated office complete the first level. Outdoors, an expansive terrace invites al fresco dining and entertaining above a manicured, secluded yard set on a coveted corner lot. Beyond the door: sunrise strolls to the water, sunsets over the boardwalk, Longshore Club, downtown shops, dining, and the library, plus a straightforward Manhattan commute via Saugatuck Metro-North. Homes in this enclave seldom surface.

4 Bradley St, Westport
4 Surrey 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
6 Canal Rd, Westport
$2,795,000
4 Beds ⋅ 3 Baths ⋅ 24206418 MLS
Rarely does a home offer such an extraordinary combination of setting, style, and convenience, while being FEMA compliant. Perched along Long Island Sound in the heart of Saugatuck, this beautifully renovated residence captures sweeping 270-degree waterfront views, with sailboats, paddleboarders, and the ever-changing rhythm of the Sound providing a captivating backdrop from morning through evening. Inside, sophisticated design meets relaxed coastal living. The home was thoughtfully reimagined by its talented local photographer owner, whose discerning eye is evident throughout. A striking new kitchen, beautifully renovated bathrooms, and hardwood floors create a refined yet welcoming interior. The waterfront experience continues outdoors with a private, low-maintenance yard and patio designed for effortless entertaining and quiet enjoyment. A private dock accommodates a small boat or kayak, putting the Sound just steps away and making boating and time on the water an integral part of daily life. Beyond its remarkable waterfront setting, the property offers exceptional accessibility, with the train station only minutes away for a convenient commute to New York City. A truly special Saugatuck offering where design, nature, and an enviable waterfront lifestyle come together.

6 Canal Rd, Westport
4 Lantern Hill Rd, Westport
$2,650,000
24196614 MLS
Rare opportunity to build a custom residence on 1.2 acres in Westport. The previous home has been demolished, and the property is offered with approved architectural plans. Bring your preferred builder and collaborate with the project architect to tailor the design to your vision. Also listed as a to-be-built single-family residence.

4 Lantern Hill Rd, Westport
4 Crawford Rd, Westport
$2,595,000
5 Beds ⋅ 4 Baths ⋅ 24203288 MLS
Privately nestled in Westport's coveted Old Hill neighborhood, this distinctive five-bedroom New England residence blends timeless character with thoughtful modern updates. Sun-filled interiors, beautifully scaled rooms, and original architectural details create warmth and authenticity throughout. The chef's kitchen is designed for both everyday living and entertaining, while the stunning, light-filled family room with fireplace offers a welcoming gathering space overlooking the beautifully landscaped grounds. A true standout is the inviting pub room with its original wood bar - an exceptional setting for entertaining, celebrations, or relaxed evenings at home. The versatile third level offers endless possibilities as a private guest retreat, second primary suite, home office or gym. Outside, mature specimen trees, flowering gardens, rolling lawns, and elegant stone terraces create a private retreat that evolves beautifully with the seasons. A charming barn with electricity, water, cable, and convenient parking adds exceptional flexibility as a studio, workshop, recreation space, or future vision. Just minutes from downtown Westport, award-winning schools, beaches, shopping, dining, and the train, 4 Crawford Road offers a rare opportunity to own a home with genuine character, exceptional privacy, and a wonderful sense of place. A truly special Westport residence that brings together character, comfort, and an exceptional setting.

4 Crawford Rd, Westport
53 Clinton Ave, Westport
$2,499,000
5 Beds ⋅ 6 Baths ⋅ 24079819 MLS
Incredibly located moments from town and convenient to schools, shopping, commuting options and more, this sparkling home showcases pride of ownership. A new 2026 driveway leads to the landscaped setting, where this gracious home with an in-ground Wagner pool is set amid .74+/- acre. The two-story foyer introduces crisp, timeless spaces, and a home that has been impeccably maintained. The living rm w/ the first of 3 fireplaces and a beautiful dining rm w/lit tray ceiling are ready for entertaining. The large gourmet kitchen w/ marble counters, La Cornue range plus wall ovens, Sub Zero, island & pantry has a sun-filled breakfast rm that leads to the lrg fam rm w/ custom built-ins, stone fpl w/ gas log set & two sets of doors to the newer deck. The mudrm has a casual entrance, door to pool, half bath & access to the 3-car garage. Upstairs, a hall w/ window seats leads to the primary suite w/ fpl, dual walk-in clsts & luxe bth. Each remaining BR is spacious & well-appointed. A flexible area w/ the 5th BR & study/play rm could become an in-law suite. The finished 3rd flr is a wonderful space for a play rm or hobbies. The vast lower level includes a great rm, a den/lib w/ custom built-ins & a full bath. The usable backyard leads to a fenced-in Wagner gunite pool w/ a "pool house." This entire home and property is in outstanding, mint condition. There is nothing for you to do but move in and enjoy this fine luxury residence. Agent/Owner

53 Clinton Ave, Westport
7 Marsh Rd, Westport
$2,049,000
3 Beds ⋅ 3 Baths ⋅ 24212313 MLS
Welcome to Saugatuck Shores, where you're not simply purchasing a home, you're embracing a lifestyle. This exceptional beach house offers an inviting floor plan, luxurious modern finishes, custom millwork, incredible water views, and a spacious private backyard. Enjoy your favorite wine al fresco from the charming screened-in front porch, expansive rear deck, or your private balcony off the primary suite. Step inside to a spacious living room anchored by a beautiful stone fireplace, an elegant formal dining room, and a stunning kitchen featuring custom white cabinetry, professional-grade stainless steel appliances, a large center island, and Carrara marble countertops. Coffered ceilings and custom millwork add character throughout the main level, which is completed by a beautiful full bath with an elegant glass-enclosed shower. Upstairs, the impressive primary suite boasts panoramic water views, a luxurious en-suite bath, walk-in closet, and access to its own private balcony. Two additional generously sized bedrooms feature beautiful wood beams that add warmth and distinctive character, while a full hallway bath is finished with marble tile and a tub/shower combination. Perfectly positioned to enjoy everything this sought-after waterfront community has to offer, while remaining just minutes from exceptional restaurants, shopping, nightlife, major highways, and the train. A rare opportunity to enjoy coastal living in one of Saugatuck's most desirable settings.

7 Marsh Rd, Westport
2 Charcoal Ln, 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
33 Bridge St, Westport
$1,999,999
2 Beds ⋅ 2 Baths ⋅ 24209600 MLS
TO BE SOLD AS-IS AND ONLY WITH #29 BRIDGE STREET together for $1,999,999....Rare opportunity to own two parcels including a 2 br cottage on the rear lot and a 6br 2-family on the front lot for investment, owner-occupant, renovation, or potential subdivision possibilities. Buyer to do own due dilligience.

33 Bridge St, Westport
29-33 Bridge St, Westport
$1,999,999
6 Beds ⋅ 3 Baths ⋅ 24209590 MLS
TO BE SOLD AS-IS AND ONLY AS A PACKAGE WITH #33 BRIDGE STREET for a total price of $1,999,999 which includes is the single family on rear lot....Rare opportunity to own two parcels including a 6br 2-family and single family for investment, owner-occupant, renovation, or subdivision possibilities. Buyer to do own due dilligience. Properties being sold in as-is condition.

29-33 Bridge St, Westport
11 Turkey Hill Cir, Westport
$1,990,000
7 Beds ⋅ 5 Baths ⋅ 24197538 MLS
Tucked away in Westport's coveted Greens Farms neighborhood, this beautifully updated home is set on over 2 acres and offers the perfect balance of comfort, flexibility, and modern living. Beloved by its owners for many years, it has been the setting for countless family gatherings, celebrations, and cherished memories and is now ready for its next chapter. The renovated kitchen features an induction cooktop, abundant pantry space, and a bright eat-in area with sliders to a newly built deck, creating an effortless connection to the beautifully landscaped backyard. The adjoining family room, with its soaring cathedral ceiling and inviting fireplace, is the perfect place to gather. The spacious primary suite offers a renovated ensuite bath, while four additional bedrooms, including one ideal for a home office, provide ample space for family and guests. A renovated hall bath features a double vanity. A private wing with its own full kitchen and separate entrance provides flexibility for an in-law or au pair suite. The walk-out lower level adds a bedroom, full bath, and generous storage for guests, recreation, or extended living. Major improvements include the roof, replacement windows and doors, exterior repainting, high-efficiency furnace, hot water heater, and oil tank. Lovingly cared for and thoughtfully updated, this special home offers space, privacy, and versatility. Just minutes from schools, beaches, train, shopping, and all that Westport has to offer

11 Turkey Hill Cir, Westport
41 Richmondville Ave Unit 105, Westport
$1,949,000
1 Beds ⋅ 2 Baths ⋅ 24209251 MLS ⋅ The Mill Westport BLDG.
Historic character meets refined modern design in this beautifully appointed one-bedroom plus den, two-bath residence at The Mill Westport. A gracious foyer provides a proper sense of arrival before opening into expansive living and entertaining spaces, where European white oak floors, historic replica windows, exposed brick, elegant lighting, and custom electric shades create a sophisticated backdrop. The open kitchen is outfitted with a suite of high-end appliances and an oversized island with generous seating, while a gas fireplace anchors the living room. Thoughtfully designed to live like a true two-bedroom, a custom sliding glass wall creates a private second sleeping area complete with a deep closet and direct access to a full bath. The spacious primary suite is tucked away on the opposite side of the residence and features a pair of closets outfitted by Poliform and a luxurious five-fixture bath with a freestanding soaking tub, walk-in rain shower, and heated floors. A full-size washer and dryer, parking, and storage are all included. Originally a historic candlewick mill dating to the 1800s, The Mill Westport has been thoughtfully reimagined as just 31 distinctive residences. Amenities include a pool and hot tub, fitness center, landscaped outdoor spaces, outdoor kitchen, residents' lounge, guest suite available for rent, and concierge services.

41 Richmondville Ave Unit 105, Westport
36 Lyons Plain Rd, Westport
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 24177591 MLS
Lovely 2.36 acres of river front land in Westport, with 300 ft. frontage on the Aspetuck River. Total tranquility! This home offers four large bedrooms including Primary bedroom with fireplace and full bath. Nice large kitchen, and a Great Room with a fireplace that opens to the deck with beautiful views of the river. Lots of privacy, and a beautiful setting! A wonderful opportunity for a renovation as is, or new build. Great location. Town appraisal is $1,898,400.00.

36 Lyons Plain Rd, Westport

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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.