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$5,650,000
7 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 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.

8 Pleasant Valley Ln, Westport
$3,795,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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
$4,250,000
6 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 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
$2,670,000
5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 24166955 MLS
Everything stays on the other side. That is what people here say about the footbridge. You cross it, and whatever you were carrying does not come with you. Compo Mill Cove is a gated private peninsula of nineteen homes on Long Island Sound, and no car has come out here since 1903. It is the reason the loudest thing you hear most mornings is the tide turning under the bridge. Everyone in this town is trying to buy quiet. Out here it is structural. This is the one with the water in every room: 5,567 SF of Brooke Girty-designed shingle style, built in 2008 and laid out so the Sound is never more than a glance away. Century-old reclaimed French oak floors. A three-story Nautilus stair through the center of the house. Five fireplaces. A Viking and SubZero kitchen. A primary suite with its own fireplace, dual walk-ins and a balcony above the water. Four bedrooms, generously scaled, plus a full third floor for guests, a studio or an office. Then the part you actually live in. A screened porch for the mornings. A Brazilian hardwood deck and hot tub for the evenings. Your own sandy beach with a kayak pulled up on it, held by a Race Coastal-engineered bulkhead. A private gate opening into the protected shoreline and woodland of Sherwood Island State Park. Green's Farms station minutes away, Manhattan about an hour. Nineteen homes. There will not be a twentieth. Your car is 150 feet away. You will not want it.

46 Compo Mill Cv, Westport
$6,375,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24165538 MLS
Boater's Paradise-Live the Ultimate Saugatuck Shores Waterfront Lifestyle. Experience unparalleled, direct waterfront access from this striking contemporary perched directly on the shores of Long Island Sound. Featuring its own rare private dock, this property is a true boater's/water lover's paradise. Enjoy all that Saugatuck Shores has to offer-boating, jet-skiing, paddle boarding, or kayaking from your own backyard. Dramatic walls of glass bathe the interior with natural light throughout effortlessly blending modern architectural lines with unparalleled, panoramic views of Bermuda Lagoon, Peck Ledge Lighthouse and boating channels which can be seen from almost every room. The open-concept main level transitions seamlessly to a massive sundeck, setting the ultimate stage for indoor-outdoor entertaining. Spend summers relaxing by your private waterfront gunite pool and spa, rinse off in your outdoor shower or unwind in the custom indoor sauna. Positioned within the coveted, private Covlee Beach Association, residents enjoy access to a private sandy beach with additional dock slips, kayak and paddleboard storage, a playground, picnic area, and fire pit just steps away, blending complete privacy with an active coastal community. From the Great Room with its dramatic fireplace and vaulted ceiling, to the custom Kitchen with fireplace, to the cozy Family Room and Study, there are so many spaces to delight. All bedrooms, including primary suite, have decks overlooking the Sound.

21 Covlee Dr, Westport
$1,329,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24158630 MLS
Spacious sophistication in the heart of Downtown Westport. Perfectly positioned just moments from shopping, dining & recreation, this lovely in-town home offers a rare blend of comfort, flexibility, and location. The inviting living room with wood-burning fireplace sets the tone for relaxed gatherings and quiet evenings alike. The open-concept kitchen features granite countertops and flows seamlessly into the dining area, with French doors leading to a private stone patio - ideal for morning coffee or alfresco entertaining. The main level includes a spacious primary suite with en-suite bath, along with two additional BRs. Downstairs, the finished lower level offers additional space with two more bedrooms and a full bath, offering flexible space for guests, rec/playroom, or multi-generational living. For those seeking a professional setup, the town-approved home occupation designation allows for a separate entrance, two offices, and a waiting room - a turnkey solution for small business owners or remote professionals. With quick access to the Westport Library, Levitt Pavilion, and the town's vibrant dining & shopping scene, this property delivers both lifestyle and convenience. Nearby commuting options include the Metro North Railroad to NYC, Merritt Parkway, I-95. A rare opportunity to live and work in one of Fairfield County's most sought-after communities, or to find a home that offers private space for visitors or extended family. AVAILABLE FOR RENT AT $6,700/mo.

310 Main St, Westport
$10,500,000
7 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24160355 MLS
Hidden along a private lane in Westport's Greens Farms neighborhood, this extraordinary 20-acre waterfront estate unfolds as one of the most remarkable shoreline settings ever offered. For more than 65 years, it has been held and enjoyed by the same family as a place to gather, unwind, and take in the ever-changing views across Sherwood Island Park and Long Island Sound. Surrounded by protected open space with no immediate neighbors, the property offers a rare sense of peace and privacy-reminiscent of the Lowcountry, the Hamptons, or Nantucket, a scale and atmosphere seldom found in Westport. Beautiful in every season, the setting also offers extraordinary birdlife and nature watching. Yet it remains moments to the Post Road, train, and town centers, and just one hour from Manhattan. A collection of residences and outbuildings is thoughtfully positioned across the land, including two circa 1940s three-bedroom guesthouses with sweeping water views, creating a true family compound where generations can come together while maintaining a sense of independence. Other structures offer flexibility for staff or future use. The grounds invite a lifestyle centered around the outdoors, with a tennis court, indoor pool, pool house, and formal gardens set within expansive lawns that stretch toward the water. Whether preserved, enhanced, or reimagined, this is a once-in-a-generation opportunity to shape a legacy estate-one that will be experienced and remembered for years to come.

4 Sherwood Island Ln, Westport
$6,595,000
6 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 24156057 MLS
Introducing an exceptional new build from Simple Plan Home Builders, multiple HOBI Award winners known for iconic Westport homes. Just a short stroll to Compo Beach, this striking modern coastal retreat is privately set on a coveted cul-de-sac, blending luxury, light, and effortless living. Spanning four levels, this six-bedroom home features an airy layout with refined finishes throughout. The open-concept kitchen flows seamlessly into the main living spaces, highlighted by a statement fireplace. A glass-enclosed office offers privacy, while additional living and dining areas, a stylish scullery, and an oversized mudroom add everyday functionality. A dramatic pivot door opens to a gallery-style entry. Upstairs, the primary suite is a serene retreat with its own fireplace, dual walk-in closets, a dressing area, and a spa-like bath. Four en-suite bedrooms and a laundry room complete the second floor, while the top level offers a private sixth suite, office, and flexible open spaces. The walk-out lower level expands the home with walls of glass, a terrace, gym, bar, wine cellar, media/playroom, and additional office. Outside, a 16'x32' pool, multiple terraces, and a grilling area create effortless summer living, complemented by a three-car garage with EV charging.

8 Loretta Ct, Westport
$5,990,000
6 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24147970 MLS
New construction by renowned Red Coat Homes, ideally set on a quiet cul-de-sac in a premier Westport neighborhood. Designed by architect Judith Larson, this exceptional home offers over 7,000 sq ft of refined living space on more than one acre, complete with a resort-style pool. Timeless architecture and sophisticated finishes create spaces ideal for entertaining, work, and everyday living, with generous room sizes, flexible living areas, and seamless indoor-outdoor flow. Additional highlights include a three-car garage and thoughtful design throughout. Conveniently located close to Westport schools, train, beaches, and town amenities, this is a rare opportunity to own a custom home in a coveted setting.

10 Mary Jane Ln, Westport
$22,825,000
8 Beds ⋅ 10 Baths ⋅ ACTIVE Status ⋅ 24159193 MLS
Direct Waterfront | Greens Farms An extraordinary new waterfront estate by award-winning Coastal Luxury Homes is coming to one of the most coveted stretches of the Connecticut shoreline. Set in the heart of Greens Farms, this spectacular 12,948 square foot modern residence will span four levels and capture sweeping, unobstructed views across Sherwood Island, Burying Hill Beach, and Long Island Sound through dramatic walls of glass designed to flood the interiors with natural light. The home will feature 8 bedrooms, 8 full baths, and 2 half baths, with expansive living and entertaining spaces that seamlessly connect indoors and out. The architecture embraces a clean contemporary design that maximizes the stunning waterfront setting while creating an atmosphere of warmth, elegance, and effortless coastal living. Resort-inspired amenities include two pools, a cold plunge, spa, infrared sauna, and a fully equipped fitness center, offering a private retreat for wellness and relaxation. For the automotive enthusiast or collector, the property also includes garage space for up to 10 cars, a rare feature for a waterfront estate. Ideally located walking distance to the Greens Farms train station and Greens Farms Academy, and just minutes to the town centers of Westport, Fairfield, and Southport. Just 55 miles to Manhattan. Completion anticipated mid-2027, with the opportunity to collaborate with the builder to customize finishes and create a home that reflects your personal lifestyle

11 Beachside Cmn, Westport
$10,650,000
6 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24148523 MLS
Another extraordinary masterpiece by Coastal Luxury Homes, ideally situated in one of Westport's premier neighborhoods. Spanning over 9000 square feet of living space this 6 bedroom estate is defined by bold architectural lines, chic designer interiors, expansive balconies and seamless indoor-outdoor living. A resort caliber pool, fully equipped outdoor kitchen, and lush manicured grounds complete this rare offering, along with a coveted 4 car garage. Schedule an appointment to meet with the premier team in luxury building to customize this home. Let us help you make your dreams come true!

11 Dogwood Ln, Westport
$4,995,000
5 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 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

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