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$2,795,000
6 Beds ⋅ 7 Baths ⋅ 24183141 MLS
Experience timeless elegance in this extraordinary Colonial estate nestled in Westport's coveted Red Coat neighborhood. Offering more than 7,000sf of beautiful living space, plus an additional 2,400sf in the finished lower level, this exceptional residence combines luxury, comfort, and functionality. Featuring 6 spacious bedrooms and 5.2 baths, the home is thoughtfully designed for both everyday living and sophisticated entertaining. The chef's kitchen is equipped with premium Wolf appliances and opens to expansive gathering spaces, while a formal dining room, private office, and game room with a dry bar provide endless opportunities to entertain. The spectacular lower level is a destination of its own, complete with a home theater, recreation room, and an impressive wine cellar for the discerning collector. The luxurious primary suite serves as a private retreat with its own fireplace, spa inspired bath with jacuzzi, private balcony, and elegant finishes. 3 additional en suite bedrooms, separate nanny quarters, and a flexible bonus room offer exceptional versatility. Recently refreshed with new interior and exterior paint, all new heating and cooling systems, and stunning hardwood floors throughout, this home is truly move in ready. A welcoming covered front porch adds classic New England charm, while the private backyard is designed for outdoor enjoyment with a built in grill, spacious patio, and integrated sound system. 3 car garage and an unbeatable location.

25 Hermit Ln, Westport
$4,795,000
6 Beds ⋅ 8 Baths ⋅ 24182984 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
$9,860,000
6 Beds ⋅ 8 Baths ⋅ 24181904 MLS
An exceptional modern residence by Compo Luxury Homes, designed by renowned architect Tanner White, set on over two private acres just minutes from downtown Westport, Compo Beach, and the train-approximately one hour from NYC. This 6-bedroom home spans approximately 9,200 square feet and showcases custom European windows and doors, sophisticated interiors, and seamless indoor-outdoor living. At the heart of the home is a spectacular chef's kitchen featuring double islands with waterfall stone countertops, designed for both everyday living and effortless entertaining. The luxurious primary suite serves as a private retreat, complete with a spa-inspired bath, expansive dressing areas, and a private balcony overlooking the property. A finished third floor offers additional flexible living space, including a sitting room and private office. The thoughtfully designed lower level provides exceptional recreational space with a gym, bonus room, bedroom, and full bath, along with opportunities to customize additional areas for a theater, golf simulator, wine cellar, or other lifestyle amenities. Outdoor living is equally compelling, featuring a heated gunite pool, covered porch with outdoor fireplace and kitchen, and expansive landscaped grounds. There is also room for a future tennis or pickleball court, allowing owners to further personalize the property to suit their lifestyle. Ready for 2026 School Year!

9 Over Rock Ln, Westport
$3,685,000
4 Beds ⋅ 6 Baths ⋅ 24180388 MLS
Welcome to this new construction project which is currently underway, with an expected completion date in the Summer of 2026. Discover the epitome of elegance and sophistication on a quiet street, in a coveted area in Westport! Stunning new luxury construction designed by renowned Coastal Luxury Homes. Known for their architectural brilliance & unparalleled craftsmanship, Coastal Luxury Homes are a testament to innovative design & meticulous attention to detail. The rich architecture features flowing lines, glass elements, & harmonious blend of natural materials, create a stunning visual impact. The interior showcases an open-concept layout that is as functional as it is beautiful. Every corner will showcase high-end finishes, from cabinetry to the designer fixtures. The rich hardwood floors guide you into the Living Room. Adjacent to the living area, the gourmet Kitchen awaits, boasting ample storage & a generous island that invites culinary creativity. The Kitchen is a chef's paradise, equipped with top-of-the-line appliances & designed for both entertaining & everyday living. The four Bedrooms with en-suite Bathrooms provide both privacy and comfort for family and guests. This home, offers not only luxury but also the convenience of nearby beaches, dining, and shopping. Don't miss the opportunity to own this architectural masterpiece presented by Coastal Luxury Homes

3 Laurel Ln, Westport
$6,795,000
7 Beds ⋅ 7 Baths ⋅ 24180715 MLS
A rare offering in Westport's coveted Compo Beach neighborhood, this extraordinary estate sits on a prized double lot just moments from Compo Beach, Longshore Club, train & vibrant downtown. Featured in Westport Magazine, the property masterfully blends the charm of a beautifully preserved historic residence from 1928 w/ a remarkable 6,000 sq ft addition completed in 2008. The result is a seamless fusion of timeless New England architecture, modern luxury and exceptional craftsmanship. Spanning 9,000 square feet across 4 finished levels, the home offers 7 bedrooms, 6 full & one half baths, 6 fireplaces, soaring 10-foot ceilings, plus a 1st floor in-law/au pair suite. Sunlight pours through an abundance of windows, enhancing the home's gracious proportions & creating a bright, welcoming atmosphere throughout. A dramatic limestone & marble foyer w/ spiral staircase introduces elegant and inviting living spaces enhanced by custom hand-carved moldings and millwork, including a gracious living room with floor-to-ceiling arched windows, library, music room & private offices. The spectacular 900-square-foot chef's kitchen and great room, anchored by a reclaimed limestone fireplace from Burgundy, France, is the heart of the home-an extraordinary gathering place where family & friends come together effortlessly for intimate evenings & grand-scale entertaining.

21 Compo Pkwy, Westport
$2,650,000
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.

53 Clinton Ave, Westport
$14,900,000
5 Beds ⋅ 9 Baths ⋅ 24179641 MLS
Panoramic views of Long Island Sound extend from this gated, resort-like estate. Designed to maximize its spectacular waterfront setting, the east-facing main house takes in the coastal views from walls of windows, glass French doors, and private balconies. Effortless indoor-outdoor flow defines the main level, where a charming screened-in porch and awning-covered veranda overlook a Gunite pool with spa. First floor rooms facing the water include the living room and office, both with fireplaces, the formal dining room and the open kitchen/family room. This floor also has a billiard/media room, full bar, refrigerated wine room, two powder rooms and laundry. Idyllic second floor primary suite features waterfront balcony and sitting room, 3 walk-in closets and marble bathroom. Three additional en-suite bedrooms, each with balconies, complete this level. Perched on the third floor is a home gym with waterfront balcony, full bath and sauna. Newly added wing above attached two-car garage with one-bedroom guest suite. Perfect for summer entertaining, the backyard terrace offers a bar with built-in barbecue and a sitting area with firepit by the pool. Beyond the manicured lawns, the 168-ft seawall leads to an 80-ft pier and 20-ft private dock. Side yard with secluded outdoor shower, exterior-access powder room and kayak storage rack. Spacious two-bedroom guest cottage with 1.5 baths, kitchen, laundry and attached one-car garage. Commercial-sized generator powers main house & cottage.

279 Saugatuck Ave, Westport
$5,750,000
5 Beds ⋅ 8 Baths ⋅ 24178699 MLS
Tucked behind a gated entry in Old Hill, this stunning 5 bedroom, 6.2 bath home offers a rare blend of elegance, privacy and natural beauty. The property has multiple serene water features-a heated saltwater gunite pool with hot tub, a tranquil private pond with fountain and picturesque Stony Brook. The stately stone and wood exterior blends seamlessly with the lush surroundings, while inside, an expansive, light-filled layout is ideal both for grand entertaining and quiet retreat. A dramatic wall of windows captures sweeping views of the brook, creating a seamless connection between indoor comfort and the surrounding landscape. The ground floor consists of a gourmet kitchen, large family room with fireplace, dining room with wet bar, living room with fireplace + lounge area with water views, a large entry foyer with stone floors and two powder rooms. Upstairs, a primary bedroom suite with two balconies overlooking the pond and brook, two walk in closets & beautifully appointed bathroom, 4 additional bedrooms each with its own bathroom, a large home office/6th bedroom with fireplace and brook & pond views, a large playroom with full bathroom, windowed home gym, and another family room on the 3rd floor, offering multiple options for relaxation and entertainment. Fully fenced for privacy with automated driveway gates, it has a heated 3 car garage, Crestron lighting system, full house generator, mature landscaping, and a gas grill seamlessly built into the stonework by the pool.

31 Stonybrook Rd, Westport
$7,926,000
6 Beds ⋅ 7 Baths ⋅ 24177287 MLS
Set within Westport's most prestigious private estate enclave, surrounded by grand coastal estates and quintessential antique treasures, this exceptional Greens Farms 2+ acre* new construction offering is poised to become one of Fairfield County's most coveted addresses. Perfectly positioned, moments from beaches, downtown boutiques, vibrant dining scene, and just an express train to Manhattan, the property offers a rare blend of privacy, convenience, and timeless sophistication. Fully customizable and designed to fit your lifestyle and desired scale, this masterfully built residence will feature bespoke craftsmanship, rich stone, curated designer finishes, advanced smart home technology, and world-class amenities tailored entirely to your vision. Expansive grounds offer tranquil space for a private resort-style setting with endless possibilities for outdoor living and recreation. Walk the property with us and the Coastal Luxury Homes team and begin designing your dream estate.

Clapboard Hill Rd Unit (New Build), 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
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 24177591 MLS
Rarely does an opportunity like this become available in Westport. Set on 2.36 private acres with approximately 300 feet along the scenic Aspetuck River, this exceptional property offers a remarkable setting to renovate, expand, or create the custom estate you've always envisioned. The existing four-bedroom residence features a spacious primary suite with fireplace, an expansive kitchen, and a great room with fireplace opening to a deck overlooking the river. Whether you choose to preserve and enhance the current home or design an entirely new legacy property, the possibilities are extraordinary. Just minutes to downtown Westport, beaches, shopping, dining, and top-rated schools, this is a rare offering in one of Fairfield County's most desirable communities.

36 Lyons Plain Rd, Westport
$1,600,000
5 Beds ⋅ 3 Baths ⋅ 24170442 MLS
Tucked away down a private drive on two serene wooded acres, this exceptional mid-century modern deck house offers the perfect blend of architectural character, privacy, and natural beauty. Bathed in tremendous natural light, the home showcases the signature design elements that make deck houses so timeless and sought after, with expansive windows, soaring ceilings, and seamless indoor-outdoor living. The four-bedroom, two-and-a-half-bath layout provides comfortable and flexible living spaces designed to embrace the surrounding landscape. 2 car detached garage to hold all of your extra and outdo0r items! Warm wood tones, open gathering areas, and walls of glass create an inviting atmosphere throughout the home. A spacious deck overlooks the peaceful property, offering the ideal setting for entertaining or quiet relaxation immersed in nature. It feels worlds away while still being conveniently located near all that Westport has to offer. Sold As Is

4 Baywood Ln, Westport
$10,500,000
4 Beds ⋅ 6 Baths ⋅ 24177056 MLS
Designed by renowned architect and builder Frazier Forman Peters, this stone estate is set on nearly 3.5 private, meticulously landscaped acres in Westport. Crafted over more than two decades, the residence reflects exceptional artistry, scale, and craftsmanship. A gated entry and winding stone drive arrive at a stately porte-cochere and attached two-car garage, establishing a grand sense of arrival. Spanning over 10,500 square feet, the home offers four bedrooms, five full baths, one half bath, and living spaces defined by soaring ceilings, natural light, and timeless materials. The formal living room serves as a centerpiece with oak herringbone floors, Venetian plaster walls and ceilings, oversized windows, and a fireplace. Nearby, a double-height dining room with vaulted ceilings and imported Jerusalem stone creates a striking setting for entertaining. The chef's kitchen features professional-grade appliances, custom cabinetry, a large center island, and adjoining sitting area. A lofted library and study wrapped in handcrafted Honduran mahogany sits beneath skylights, while additional gathering spaces include a den, sunroom, wet bar, billiards lounge, and media room. A dedicated wellness wing offers an indoor lap pool, fitness center, sauna, and primary suite with dressing gallery, spa bath, studio, and private retreat. Grounds include an outdoor pool, tennis court, greenhouse, gazebo, pool house, and separate groundskeeper's residence.

47 Charcoal Hill Rd, Westport
$4,995,700
4 Beds ⋅ 5 Baths ⋅ 24176377 MLS
Come walk this stunning 1.5 acre lot with me - totally private, tucked at the end of a cul de sac in Long Lots. Peace, quiet, and the highest quality custom home spec'd to your wishlist by Coastal Luxury Homes is yours at 22 Dawn Drive. Go bigger/smaller, add an in-law suite or extra bedroom, an art studio, include a pool/spa, pickle court... let's discuss all the possibilities. Square footage and specs can vary, but the standard of excellence does not. Coastal Luxury Homes is the premier Fairfield County bespoke builder.

22 Dawn Dr, Westport
$4,100,000
6 Beds ⋅ 6 Baths ⋅ 24164137 MLS
A rare opportunity to own new construction in Westport's coveted Old Hill neighborhood, offering refined design, a swimming pool, and a walkable lifestyle near Post Road and downtown. Tucked within one of Westport's most sought-after enclaves, this newly constructed 6-bedroom, 5.5-bath home blends architectural sophistication with modern livability. Natural light, clean lines, and well-proportioned spaces create an environment that feels both elevated and effortlessly comfortable. At the center of the home, a beautifully designed kitchen opens to expansive living and dining areas, creating a seamless flow for both everyday living and entertaining. The layout flows easily with ample room for work-from-home, multi-generational living, and evolving lifestyle needs. A main-level suite with a full bath provides privacy and versatility-ideal for guests, a dedicated office, or an extended family. Every detail accentuates comfort, function, and understated luxury. A back yard patio with pool abutting a nature preserve offers privacy with open space and the ease of in-town living. Positioned near Nash Pond and close to local nature trails and amenities, the home also offers exceptional convenience-walkable to the Post Road and just minutes to downtown Westport, shopping, dining, and Metro-North train service to New York City. Luxury new construction in Old Hill, Westport, CT-where location, design, and lifestyle align in one of the town's most desirable settings.

48 Woodside Ave, 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
$4,050,000
6 Beds ⋅ 9 Baths ⋅ 24174753 MLS
Set in one of Westport's most prestigious estate enclaves, this exceptional shingle-style residence defines luxury living with a rare emphasis on multi-generational comfort, timeless architecture, and impeccable craftsmanship. Designed and built by a renowned architect and builder for a Fortune 500 CEO, the home reflects uncompromising quality, enduring design, and gracious curb appeal that impresses. Seamless indoor-outdoor living defines the home, with sun-filled interiors, soaring 10-foot ceilings, and an expansive walkout lower level with fireplace, all opening to a resort-style pool, stone patios, fire pit, and covered porch with fireplace, providing an effortless setting for entertaining. Extensive bespoke millwork, six fireplaces, and refined architectural finishes enrich every space. The expansive, level, and private grounds, framed by mature landscaping and abutting the 39-acre Newman Preserve, offer serenity with rare walkability to top-rated schools and 8 minutes to Westport's lively downtown. A spectacular chef's kitchen features Thermador and Wolf appliances, dual islands, 2 dishwashers, walk-in pantry, and a fully equipped butler's pantry with wet bar. The primary suite offers a turreted sitting room, fireplace, and 2 walk-in closets. 6 ensuite bedrooms and a private suite over the garage provide flexibility for guests. Space for elevator! New cedar roof, new boiler, new wine cellar, and other upgrades complete this rare offering in a premier Westport location.

278 North Ave, Westport
$5,000,000
6 Beds ⋅ 7 Baths ⋅ 24168601 MLS
Nestled on a quiet cul-de-sac in one of Westport's most convenient locations, 6 Twin Circle Drive offers luxury living with exceptional indoor and outdoor spaces. Just moments to Bedford Middle School, Staples High School, downtown Westport, trains, shopping, restaurants, Longshore, and Compo Beach, this property combines privacy, recreation, and convenience. The resort-style backyard features a pool with spa, expansive lounging areas, full outdoor kitchen, and a rare post-tension concrete tennis court - the premier surface used at elite clubs and college facilities. A truly extraordinary amenity rarely found in residential homes. The home offers an open floor plan filled with natural light and thoughtfully designed spaces. The gourmet chef's kitchen features high-end appliances, abundant workspace, and two dishwashers. Main-level highlights include elegant entertaining spaces, a private meditation room, and seamless indoor-outdoor flow. The primary suite is a retreat with a spa-inspired bath, steam shower, and dressing room with abundant closets. Upstairs, an incredible playroom with six built-in beds creates the perfect sleepover space or playroom. The walk-out lower level offers versatility with a media room, gym, office, and guest suite ideal for extended family, au pair, or guests. Rarely does a Westport luxury home offer resort-style amenities, premier tennis facilities, flexible living space, and walk-to-school convenience in such a private setting.

6 Twin Circle Dr, Westport
$5,650,000
7 Beds ⋅ 9 Baths ⋅ 24172635 MLS
Experience modern luxury in this new SIR SIGNATURE Home by SIR Development, Westport's premier builder. Set on 1.02 private acres on a coveted cul de sac, this home offers a striking approach, 3car garage, and rare backyard privacy, all within walking distance to Bedford Middle, Staples High, Wakeman Fields, and Town Farm. A fresh contemporary aesthetic features a dramatic two story foyer, 10ft ceilings, custom paneling, character grade oak floors, refined millwork, and expansive windows. Sun-filled living and dining rooms complement the great room with a sleek 60inch fireplace and reclaimed beams. The chef's kitchen includes full size SubZero refrigerator and freezer, Wolf cooktop and double ovens, quartzite waterfall island, custom cabinetry, and walk-in pantry. A private office with built ins enhances work from home convenience. Outdoor living shines with a covered porch, granite patio, outdoor kitchen, and direct access to the 20x40 saltwater pool. The luxurious primary suite offers vaulted ceilings with antique beams, oversized walk ins, and a spa bath with custom vanities and textured tile. All five second floor bedrooms are ensuite. The finished third floor adds a full bath, office/craft room, and playroom. The walkout lower level includes a bedroom and bath, gym, wet bar, media room with raised platform, and large recreation area. **Images with exterior are AI Altered. House is complete inside. Exteriors complete 6/15/26.** **See Addendum**

8 Pleasant Valley Ln, Westport
$5,500,000
5 Beds ⋅ 6 Baths ⋅ 24171432 MLS
Discover exceptional modern living in this stunning new construction home set on 1.68 acres of private, serene property in Westport, CT. Designed with both luxury and functionality in mind, this residence offers 5 spacious bedrooms and 7 beautifully appointed bathrooms. The primary suite is a true sanctuary, featuring three generous closets and a spa-inspired feel. Each additional bedroom is thoughtfully designed with ample space and comfort. Upstairs, a bright and inviting sitting area creates the perfect retreat, while a fully finished attic provides an ideal space for a playroom or creative zone. The heart of the home is a chef's kitchen, showcasing elegant oak cabinetry, high-end finishes, and a large walk-in pantry-perfect for everyday living and entertaining alike. A dedicated home office on the main level adds convenience for today's lifestyle. The fully finished basement offers incredible versatility, ideal for a home gym, bar, or entertainment space. Step outside to a beautiful, expansive patio overlooking the private grounds-perfect for gatherings or quiet relaxation. Completing this remarkable home is a 3-car garage and a sleek, modern design throughout. This is a rare opportunity to own a truly special property that combines sophistication, space, and privacy in one of Westport's most desirable locations.

1 Twin Oaks Ln, Westport
$2,400,000
5 Beds ⋅ 5 Baths ⋅ 24168651 MLS
Beautifully renovated 1799 antique Colonial offering timeless charm, modern luxury, flat pool-worthy property, and exceptional convenience, just one light to the Greens Farms train. This special home captures the soul of historic Westport while delivering the comfort of today's lifestyle. Thoughtfully renovated, it blends original character, architectural detail, warmth, and six fireplaces with the amenities today's buyers expect. Set on a flat property with room for a potential pool, the home offers inviting indoor and outdoor spaces ideal for entertaining and everyday living. At the center is a chef's kitchen with a Sub-Zero refrigerator, a Wolf range, custom cabinetry, and generous prep space, opening to a sun-filled family room. Formal rooms, antique details, and multiple fireplaces create a space that feels both elegant and welcoming. The primary suite offers an oversized dressing room with abundant closet space, and a spa-like bath with a soaking tub and steam shower. The finished lower level includes a game room, wine cellar, and flexible recreation space. Outside, the expansive lawn offers space for sports, gatherings, gardens, or a future pool. Ideally located with one light to Greens Farms train, and minutes to Long Lots Elementary, Post Road shopping, and Main Street dining. A rare blend of antique charm and modern living.

28 Bulkley Ave N, Westport
$3,795,000
4 Beds ⋅ 4 Baths ⋅ 24171986 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 maintaining 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
$1,599,876
5 Beds ⋅ 4 Baths ⋅ 24170706 MLS
Coveted Old Hill neighborhood! This stone and shingle 10 room colonial is detailed with custom millwork, recessed lighting and beautiful hardwood floors throughout. The front to back living room with marble fireplace offers peaceful views through expansive windows. The formal dining room with picture window is adjacent to a generous country kitchen featuring a bay window, granite countertops, a gas cooktop and double ovens. The oversized family room boasts a vaulted ceiling and access to main level laundry area. The rear of the house features a 58 ft long deck overlooking private acreage. The home contains 5 bedrooms and 4 full bathrooms. The primary suite includes a full bathroom, dressing area, linen closet and a walk in closet with built-in armoire. This home has fabulous closet space with each bedroom offering a minimum of 2 closets. The walk out lower level hosts a private den / office with wet bar and sliders to a stone patio. There is an additional laundry area and storage space that leads to an oversized 2 bay garage. Central air conditioning will keep you comfortable during summer months while five zone heating, Thermopane windows and extra insulation keep this home energy efficient all year long. Westport's luxury shops, fine restaurants, relaxing beaches and award winning school system combine to make this an irresistible value!

30 Pequot Trl, Westport
$949,000
4 Beds ⋅ 3 Baths ⋅ 24170020 MLS
Nestled in one of Westport's most sought-after in-town neighborhoods, 7 Lincoln Street offers a rare opportunity to own a home that has been lovingly maintained and quietly cherished for more than five decades. Just moments from the Saugatuck River, vibrant Main Street, Saugatuck Village, train to NYC, Compo Beach. Easy access to local schools without a car or bus. This property delivers a lifestyle defined by convenience, connectivity, & coastal charm. The home showcases enduring pride of ownership, w/beautiful landscaping that creates a sense of calm and welcome from the moment you arrive. Inside with natural light filled windows, wood floors, exposed brick, stainless appliances. A finished loft 3rd floor with large skylights opening to fresh air and view of the sparkling river. One car garage, driveway with space for two cars. Inviting natural wood front porch and a fenced in yard with private spaces for entertaining and relaxing under a gazebo for casual living. A versatile floor plan supports today's living needs as a single family home with the opportunity of a top two-floor legal accessory apartment - perfect for extended living, guests, or income-producing potential. Whether you envision moving right in, updating to make it your own, creating something entirely new, or just investing, the possibilities here are undeniable. Opportunities like this - a valuable combination of charm, ideal location, well cared for, with multiple use potential- rarely come to market.

7 Lincoln St, 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
$3,450,000
5 Beds ⋅ 5 Baths ⋅ 24169922 MLS
A rare offering indeed! Welcome to 4 Charcoal Lane, an unrivaled multi-generational estate mere minutes from top-rated schools, shopping, restaurants and all that Westport has to offer. Sited on 2 private acres, this extraordinary property offers panoramic views of a 7-acre nature preserve, affording permanent tranquility. The meticulous renovations center around a gracious farmhouse-style Colonial with stunning features and superior craftsmanship, plus a spectacular post-and-beam Party Barn. A gourmet chef's Kitchen is the heart of the main residence, featuring a 14-foot Calacatta marble island and a suite of professional-grade appliances with dual Family Room fireplaces nearby. The Living Room's unique tray ceiling was specially designed for a superior piano experience. Upstairs, the Primary Suite is highlighted by a gorgeous spa bath. The property's exceptional appeal is anchored by the Country Carpenters barn, connected by a breezeway w/barn doors that create an inviting welcome to backyard entertaining. This luxury 1BR barn features 20-foot ceilings, heated floors, a full kitchen, and hinge-free retractable doors to seamlessly blend indoor/outdoor living. Resort-style amenities await outdoors with a Pebble Tec pool, waterfall hot tub & blue granite patio that remains cool underfoot on hot summer days. The entertainment porch features built-in heaters, see-thru fireplace and outdoor television. This is more than just a home, it's a legacy waiting to be claimed!

4 Charcoal Ln, Westport
$4,799,000
5 Beds ⋅ 6 Baths ⋅ 24167814 MLS
Just completed and ready for immediate occupancy, this beautifully crafted new construction home is set on a quiet cul-de-sac in the desirable Greens Farms area. Situated on a level one-acre property with a pool, the home is filled with abundant natural light and offers a thoughtful, well-balanced layout designed for both everyday living and entertaining. The stunning kitchen opens to a dramatic double-height family room, creating an inviting central gathering space. With five-plus bedrooms, including a first-floor primary suite featuring a spacious walk-in closet and a well-appointed bath, the home provides flexibility to suit a variety of living arrangements. Two laundry rooms add convenience, while high-end finishes and attention to detail are evident throughout. A fully finished lower level offers additional living space with a gym, recreation area, and more. Ideally located for commuting, with easy access to town, beaches, shopping, and transportation.

11 Wake Robin Rd, Westport
$2,790,000
5 Beds ⋅ 3 Baths ⋅ 24161256 MLS
A rare opportunity to own one of Charcoal Hill's signature properties, this exceptional Frazier Peters stone home pairs historic craftsmanship with a level of care and refinement that is increasingly hard to find. Set atop 2.3 +/- gated acres and introduced through a stunning circular drive, the residence showcases Peters' hallmark use of native stone, warm wood tones, and artisan detail, creating a home that feels both enduring and deeply inviting. More recent expansion and remodeling have sensitively enhanced the home. Sunfilled rooms with vaulted ceilings and handhewn finishes offer a balance of scale, with multiple living spaces that transition seamlessly to the outdoors. The grounds unfold in a series of thoughtfully designed moments including lush perennial gardens, winding paths, quiet terraces, and vibrant seasonal color. At the center is a sparkling, oversized pool with a waterfall spa and a fully outfitted stone pool house, which is an ideal retreat for summer living. A heated 4car stone garage with a finished upper level provides flexible space for a studio, office, or possible guest space. Every corner of the property reveals another place to gather, from sunny patios to shaded areas beneath large awnings, all wrapped in exceptional privacy yet minutes to the energy and amenities of downtown Westport. A home where history, beauty, and modern comfort come together with uncommon harmony.

56 Charcoal Hill Rd, Westport
$11,995,000
5 Beds ⋅ 7 Baths ⋅ 24167794 MLS
Summer starts here. Set on prestigious Owenoke Park steps from Compo Beach, this brand-new 6,050 sqft coastal masterpiece delivers the ultimate Westport lifestyle - pool and spa, Gray's Creek waterfront access, Long Island Sound views throughout, and a rare 3-car garage. Five ensuite bedrooms, double-island kitchen with scullery, elevator, primary suite sauna, and a lower-level loggia built for entertaining. New construction. Never lived in. Move in this weekend. Bluewater Home Builders

14 Owenoke Park, Westport
$5,895,000
4 Beds ⋅ 6 Baths ⋅ 24166955 MLS
Set within Compo Mill Cove, a rare private association where homes are accessed only by footbridge and no cars are permitted, this Brooke Girty-designed shingle-style residence offers 5,567 SF of true coastal sanctuary. The footbridge approach immediately separates the home from daily life, delivering a level of seclusion few coastal properties can match. Interiors are warm, considered, and serene: reclaimed French oak floors, a sculptural three-story spiral staircase, and walls of windows framing sweeping Long Island Sound views. The screened porch invites long mornings; the hot tub, slow evenings; the private beach with kayak launch, full days spent entirely on the water. Direct gated access to Sherwood Island State Park extends the sense of refuge across acres of protected shoreline, woodland, and walking trails. Just over an hour from NYC, yet feels worlds removed. A home defined by privacy, quiet, and escape rather than spectacle - an everyday retreat in every season.

46 Compo Mill Cv, Westport

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