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379 Ocean Dr W, Stamford
$14,500,000
6 Beds ⋅ 8 Baths ⋅ 24184829 MLS
Completed in 2023 and designed by Michael Smith Architects, this extraordinary six bedroom waterfront residence offers more than 8,700 square feet of luxury living along one of Stamford's most coveted stretches of Ocean Drive West. Built two feet above FEMA flood elevation requirements and featuring sweeping views of Long Island Sound from every principal room, the home combines timeless coastal architecture, exceptional craftsmanship, and modern construction. Thoughtfully designed for both grand entertaining and everyday living, the residence balances expansive gathering spaces with private retreats, all oriented toward the water. A cedar shake exterior, stone detailing, and sunrise to sunset exposure define the home's striking waterfront presence. Across three levels, terraces, balconies, and principal living spaces are carefully positioned to capture panoramic views of Long Island Sound, creating a seamless connection between the interior and the surrounding landscape. The result is a residence equally suited for weekend escapes, year round living, and large scale entertaining. (One of the owners is a licensed real estate agent.)

379 Ocean Dr W, Stamford
57 Rowayton Ave, Norwalk
$10,995,000
3 Beds ⋅ 4 Baths ⋅ 24198387 MLS
Welcome to 57 Rowayton Ave., where refined luxury meets effortless coastal living in the heart of Rowayton. Designed by Beinfield Architecture, this exceptional waterfront home offers sophisticated design, timeless craftsmanship, and an unparalleled location on the Five Mile River. Ideally situated beside the town dock and steps from Rowayton Seafood, this 3-bedroom, 5-bath home combines water views, a private 38-foot dock, and the convenience of village living. Inspired by the elegance of a luxury yacht, the home features rich mahogany throughout, from the custom kitchen countertops to the dramatic family room with its soaring arched ceiling. Walls of glass and expansive accordion doors open to a stunning waterfront terrace, creating a seamless connection between indoor and outdoor living. The open-concept floor plan is filled with natural light and designed for everyday living and entertaining. An elevator services every level, while a temperature-controlled wine cellar adds another thoughtful luxury. The chef's kitchen by Kitchens by Deane features custom cabinetry, premium appliances, and exceptional finishes. The primary suite offers sweeping river views, dual spa-inspired baths, and 2 walk-in closets. 2 additional bedrooms and a spacious 2-car garage complete the home. Offering exceptional architecture, deep-water access to LIS, and one of the most desirable waterfront locations, 57 Rowayton Ave. is a rare opportunity to experience the best of coastal living.

57 Rowayton Ave, Norwalk
11 Manitou Ct, Westport
$8,995,000
7 Beds ⋅ 9 Baths ⋅ 24068543 MLS
Perched gracefully atop a bluff on a premier private cul de sac overlooking Longshore and the shimmering expanse of Long Island Sound, this exquisite coastal residence embodies a harmonious synthesis of timeless Hamptons style and contemporary modern chic. This estate offers a lifestyle of unparalleled sophistication, effortless elegance, cutting edge innovation, and tranquil opulence. Imagine days on your sun-drenched terraces, reading under the covered porches, a swim in your oversized infinity edge pool with spa, walks to the beach as the backdrop to your everyday life. Inside, discover luxurious living spaces designed for both intimate gatherings and grand entertaining; soaring ceilings; walls of windows; generous stone embellishments; a swoon worthy kitchen with scullery; 6/7 bedrooms which includes the primary bedroom suite with fireplace and generous balcony deck; 8/1 baths; elevator; recreation and wellness retreat with infrared sauna, steam shower, cold plunge, golf simulator, wet bar, and more in the lower level. Artful in architecture and design, indulgent in amenities and appointments, every detail in this home is a testament to the Builder's exceptional craftsmanship and his unwavering dedication to delivering the highest quality construction. The new definition of a Coastal Luxury Masterpiece is HERE... "Manitou Bluff", Westport CT

11 Manitou Ct, Westport
11 Harbor Bluff Ln Unit 11, Norwalk
$8,475,000
5 Beds ⋅ 7 Baths ⋅ 24180499 MLS ⋅ Harbor Bluff BLDG.
Commanding panoramic views of Long Island Sound, this extraordinary coastal retreat offers a front-row seat to the dramatic interplay of sea, sky & light. Thoughtfully designed by Louise Brooks of Brooks & Falotico, the residence blends timeless elegance w/ exceptional craftsmanship and over 9,000 sqft of refined living space across 4 elevator-serviced levels. Designed for both relaxed living & sophisticated entertaining, the home features a stunning chef's kitchen w/ professional-grade appliances, fireplace & imported French heated stone floors. Sun-filled living & dining rooms offer French doors that lead to a private terrace overlooking Tavern Island, Rowayton Harbor, & the sparkling Sound. 5 beautifully appointed en-suite bedrooms provide comfort & privacy, including a luxurious primary suite w/ a recently renovated spa bath, steam shower, soaking tub, custom vanities & walk-in closets. A spacious private office with built-ins offers a serene work-from-home setting, and guests can enjoy a charming 3rd fl. bedroom w/bath. A spectacular top-floor entertainment space w/ kitchenette opens to a deck with sweeping waterviews for gatherings & sunsets. The lower level is dedicated to wellness & recreation, featuring a gym, sauna, wineroom, & abundant storage. Nestled within Harbor Bluff, an exclusive enclave of just 12 custom homes, residents enjoy a lock-and-leave lifestyle w/ the privacy of a Single-family residence. Coastal Connecticut living at its finest.

11 Harbor Bluff Ln Unit 11, Norwalk
4a Compo Pkwy, Westport
$7,990,000
6 Beds ⋅ 8 Baths ⋅ 24194541 MLS
Build your coastal dream home on a rare, full acre* property along one of Compo Beach's most coveted cul-de-sacs, where opportunities of this caliber seldom become available. Ideally positioned just across from Longshore and moments from the shoreline, this extraordinary setting places Westport's most treasured amenities at your fingertips: golf, tennis, swimming, boating, beaches, playgrounds, fine dining, and more. To be custom built by Coastal Luxury Homes, Fairfield County's foremost luxury builder, this distinguished residence will offer three beautifully finished levels defined by unrivaled quality and meticulous craftsmanship. Expansive walls of glass will bathe the interiors in natural light, showcase the magnificent grounds, and create a seamless connection to the outdoors. Exquisite millwork, natural stone, refined finishes, a curated selection of top-tier appliances, and generous allowances will elevate every space, while the sumptuous primary suite will serve as a private, resort-inspired retreat. Thoughtfully tailored to your every wish with room for a pool, this remarkable home will reflect your personal style and vision for sophisticated coastal living.

4a Compo Pkwy, Westport
16 E Trail, Darien
$7,950,000
9 Beds ⋅ 10 Baths ⋅ 24168537 MLS
Set within the coveted Tokeneke Association, 16 East Trail is a rare legacy property where architectural pedigree meets modern luxury. Originally built in 1908 as one of the enclave's earliest residences, the home reflects the timeless elegance of McKim, Mead & White and Delano & Aldrich-thoughtfully reimagined for today's living. A masterful renovation by architect Peter Pennoyer preserves the home's historic integrity while introducing refined, livable spaces. Interiors by acclaimed designer Katie Ridder bring a fresh yet classic sensibility, blending color, texture, and bespoke detail throughout. The main residence offers 7 bedrooms and 6 full baths, anchored by five fireplaces that add warmth and character across its gracious living spaces. A classic carriage house offers a fully equipped 2-bedroom, 1-bath guest residence with its own kitchen, providing exceptional flexibility-ideal for extended stays, in-law living, or a private home office retreat. The grounds, designed by renowned landscape architect Janice Parker, are a true highlight-lush, structured, and beautifully layered for year-round interest. An in-ground saltwater pool completes the estate-like setting, creating a private retreat perfect for both entertaining and quiet enjoyment. Rich in history and elevated by a world-class design team, 16 East Trail offers a rare opportunity to own a piece of Darien's architectural legacy-seamlessly tailored for modern living.

16 E Trail, Darien
94 Porchuck Rd, Greenwich
$7,500,000
6 Beds ⋅ 9 Baths ⋅ 24148128 MLS
2026 NEW CONSTRUCTION - CAN FULLY CUSTOMIZE AT THIS STAGE. Set back on a quiet private drive in a coveted central Greenwich location, this 12,000+/- sq ft modern masterpiece sits on 5.59 serene acres with exceptional landscaping and privacy. Designed for today's lifestyle, it offers 6 ensuite bedrooms, 7 full and 2 half baths, and four levels of refined living. Expansive windows, soaring ceilings, and custom finishes fill the home with light and sophistication. A chef's kitchen with professional-grade appliances anchors the living spaces. Outside, enjoy a heated Gunite pool and spa, stone fireplace, and beautiful grounds. Additional highlights include a 3-car garage, advanced systems, and elevator-ready space. Minutes to town, schools, transportation, NYC, and airports. One of two new homes being built along with 96 Porchuck Road. Still time to fully customize. Buyer did not perform so house is fully available.

94 Porchuck Rd, Greenwich
96 Porchuck Rd, Greenwich
$7,500,000
6 Beds ⋅ 10 Baths ⋅ 24132023 MLS
2026 NEW CONSTRUCTION - CAN FULLY CUSTOMIZE AT THIS STAGE - Set on 4.35 private and quiet acres in backcountry Greenwich, this modern farmhouse offers over 10,000 sq ft of refined living. Designed for today's lifestyle, the home blends classic architecture with modern accents -steep gables, expansive windows, and natural stone accents. Light-filled interiors feature 6 en-suite bedrooms, 8 full and 2 half baths, soaring ceilings, and custom finishes. The chef's kitchen with professional-grade appliances opens to multiple living and dining spaces. Outside, a heated Gunite pool, spa, and outdoor fireplace create an effortless indoor-outdoor flow. Every detail reflects modern luxury and timeless design, minutes to Greenwich town and schools as well as easy proximity to Westchester and NYC.

96 Porchuck Rd, Greenwich
69 Beachside Ave, Westport
$7,350,000
6 Beds ⋅ 7 Baths ⋅ 24152219 MLS
Set behind gates on over four exquisitely landscaped acres in Westport's coveted Beachside enclave, 69 Beachside Avenue is a private coastal estate offering a rare blend of scale, privacy, and resort-style living just moments from the shoreline. A long, gracious approach leads to a timeless residence defined by exceptional craftsmanship and sun-filled interiors. Expansive living spaces feature soaring ceilings, seamless flow, and walls of glass that frame the estate's serene, park-like setting-ideal for both grand entertaining and everyday living. At the center of the home, a chef's kitchen opens to elegant formal and informal spaces, creating an effortless environment for hosting. Each room is thoughtfully appointed with high-end finishes, bespoke details, and a refined sense of understated luxury, now fully realized with a newly completed primary bath designed as a private, spa-like retreat. Outdoors, the property transforms into a true resort experience, with a stunning pool and spa, spacious terraces, and a full Har-Tru tennis court set amid rolling lawns and mature plantings, offering exceptional privacy and tranquility. Perfectly positioned near Westport's beaches, Longshore Club, and vibrant downtown, this property also offers the rare advantage of direct access to Greens Farms Academy, a feature shared by only a select few homes. This property is where luxury, land, and lifestyle come together in one of Westport's most prestigious addresses.

69 Beachside Ave, Westport
41 Rowayton Ave, Norwalk
$7,000,000
4 Beds ⋅ 5 Baths ⋅ 24154329 MLS
There are waterfront homes, and then there are properties that truly define waterfront living. 41 Rowayton Avenue is one of those rare offerings, bringing together the features buyers search for but almost never find in a single property: direct waterfront, a private dock, sandy beach, waterside pool, and coveted Rowayton Beach Association membership. Sunlight pours through the home's inviting interior, creating a warm and welcoming space for effortless entertaining, boating adventures, afternoons by the pool, and evenings enjoying breathtaking sunsets over the water. Just moments from Rowayton Village and approximately one hour from Manhattan, this is an exceptional opportunity to experience one of Connecticut's most complete waterfront lifestyles.

41 Rowayton Ave, Norwalk
1 Loch Ln, Greenwich
$6,950,000
5 Beds ⋅ 8 Baths ⋅ 24209049 MLS
Privately positioned on 3.5 acres at the end of a quiet mid-country Greenwich cul-de-sac, this distinguished stone and brick estate offers an exceptional blend of timeless architecture, refined interiors and resort-style living. Designed with both grand entertaining and everyday comfort in mind, the residence unfolds across three beautifully appointed levels, all connected by a wood-paneled elevator. Elegant formal rooms give way to a chef's kitchen, coffered-ceiling family room and private office, while multiple doors invite effortless indoor-outdoor living. Five ensuite bedrooms provide luxurious accommodations, complemented by a versatile bonus room. The walk-out lower level is a destination unto itself, featuring a fireside game room, full bar, wine cellar, private theater and sauna. Outside, sweeping lawns, mature landscaping and lush gardens surround the pool, pergola, summer kitchen and covered terrace, creating a serene and exceptionally private setting. A gated entrance and four-car garage complete this impressive Greenwich estate.

1 Loch Ln, Greenwich
124 Hillandale Rd, Westport
$6,500,000
6 Beds ⋅ 10 Baths ⋅ 24184011 MLS
An exceptional home in coveted Greens Farms, 124 Hillandale Road captures the essence of classic Connecticut living. Timeless, elegant, and impeccably maintained, this beautiful estate is surrounded by mature landscaping and a peaceful, private setting, while remaining just minutes from everything Westport has to offer. Spanning four finished levels connected by an elevator, the home seamlessly blends classic architecture with modern comfort. Sun-filled living spaces, beautiful millwork, and thoughtfully designed interiors create an atmosphere that is both sophisticated and welcoming. Whether hosting family and friends or enjoying a quiet evening at home, the layout is designed to accommodate every stage of life with ease. Every detail has been carefully considered, from the state-of-the-art movie theater and golf simulator to the fitness and recreation spaces that make everyday living feel a little more special. Outside, beautifully landscaped grounds and picture perfect pool with auto-cover provide the perfect backdrop for relaxing, entertaining, and making lasting memories, with an outdoor fireplace and multiple gathering spaces to enjoy throughout the seasons. Effortlessly elegant, 124 Hillandale Road embodies the very best of Greens Farms living-a home where timeless design and modern amenities come together to create something truly special.

124 Hillandale Rd, Westport
298 Harbor Rd, Fairfield
$5,995,000
5 Beds ⋅ 7 Baths ⋅ 24200591 MLS
What began as the restoration of sea captain Ward Bulkley 1834 home became something far more extraordinary. The years-long transformation of 298 Harbor Road, recently featured in Architectural Digest, brought together architect JP Franzen and Moore House Design to carefully preserve and reimagine nearly two centuries of history. No detail was too small and no opportunity to honor the original home overlooked. The result preserves the character and craftsmanship of another era while creating a home that, for all its beauty and pedigree, is remarkably comfortable, inviting and meant to be lived in. Generations of additions were reconsidered and unified; original pine floors preserved; millwork expanded; and Venetian plaster, reclaimed stone and artisan finishes introduced with extraordinary attention to craft. A spectacular vaulted kitchen centered around an 11-foot island exemplifies how seamlessly historic architecture and modern living were brought together. Behind the wood-paneled staircase, a hidden speakeasy offers an unexpected nod to another era-one of the many details that makes this home so intriguing. The home offers 5 bedrooms, 5 full and 2 half baths, with the rare flexibility of a first- or second-floor primary suite. Set on .8 acres with seasonal water views, a pool and spa, and outdoor sauna, 298 Harbor Road achieves something exceedingly rare: a remarkable convergence of history, exceptional design and modern luxury in the heart of Southport Village.

298 Harbor Rd, Fairfield
25 Ellery Ln, Westport
$5,926,000
7 Beds ⋅ 9 Baths ⋅ 24100505 MLS
Work is underway at 25 Ellery! Have you been quietly creating a wishlist of EVERYTHING you want in your next home? This new mini-estate on a preferred Greens Farms cul-de-sac is YOUR EVERYTHING! There will be no reason to leave home - 25 Ellery offers it all including a pool with spa and auto cover. The flow of this house is divine. Rooms are spacious, comfortable, and well-thought out for today's lifestyle. Windows are exquisitely oversized offering private views of the 1 acre property. Expect nothing but the best luxury amenities, finishes, allowances, and expert craftsmanship in true Coastal Luxury Homes' fashion. Entertaining deck off the amazing kitchen and family room. Designed with 7 total bedrooms (5 bdrms on flr 2, 1 bdrm on flr 3, 1 bdrm in LL) - the Primary suite with fireplace also has a balcony facing morning sunshine. Work from home options on every level. Workout at home in your state-of-the-art home gym located in the walkout lower level. Media/playroom/rec room to be customized to your whims. I can't wait to share the plans with you. This one is REALLY good.

25 Ellery Ln, Westport
46 Compo Mill Cv, Westport
$5,895,000
4 Beds ⋅ 6 Baths ⋅ 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
9 Sturges Hwy, Westport
$5,474,945
7 Beds ⋅ 8 Baths ⋅ 24073111 MLS
Design Your Dream Home with an Award-Winning Builder. Step into a world of elegance and sophistication with a soon-to-be-built 6,660 sq. ft. masterpiece by Coastal Luxury Homes. Known for their innovative designs, sleek modern lines, and unparalleled craftsmanship, Coastal Luxury Homes has earned a reputation for creating some of the most sought-after residences. With a focus on prime location, architectural brilliance, meticulous site design, and quality construction, their homes redefine luxury living. This stunning estate is situated on over 6 acres of rare, coveted land in Westport's prestigious Hunt Club neighborhood-a location that hasn't been available for purchase in over fifty years. Coastal Luxury Homes has carefully secured and subdivided this private property into three custom estates, each offering a unique blend of privacy, tranquility and opulence. Blending cutting-edge architecture and state-of-the-art amenities, this home will be a true sanctuary. From the spa-inspired master suite to the open-concept living areas and seamless indoor-outdoor flow, every inch of this home will be designed for those who appreciate the finest in modern living.

9 Sturges Hwy, Westport
34 Nearwater Rd, Norwalk
$5,295,000
4 Beds ⋅ 6 Baths ⋅ 24196747 MLS
Welcome to 34 Nearwater Road, an exquisite home in the coveted Pine Point Assoc., just steps from Crescent Beach. This turnkey gem offers year-round water views & a seamless blend of luxury and comfort. The light-filled interior boasts soaring ceilings & an open floor plan that feels both elegant and inviting. The living room, anchored by a wood-burning fireplace, exudes charm, while the formal dining room shines w/ sophisticated coffered ceilings. At the heart of the home is a chef's kitchen featuring state-of-the-art appliances - including 2 refrigerators and dishwashers, perfect for culinary adventures. Adjacent spaces include a bright office & a chic bar area, making entertaining effortless. A refined powder room completes the main level. Upstairs, the primary suite is a true retreat with a cozy gas fireplace, 2 walk-in closets, and a spa-like bath with a tub. Three additional ensuite bedrooms ensure privacy for family & guests, while the laundry room adds convenience. The 3rd floor, w/ breathtaking water views of LIS & Farm Creek, features a full bathroom & versatile space ideal for work, fitness, or play. On the lower level, a large mudroom features ample storage & the large, extra-deep two-car garage provides easy access. Outside, the oversized front patio w/ stunning Long Island Sound water views, is perfect for morning coffee or evening gatherings around the gas fire pit. Enjoy coastal living within walking distance of the beach, town, & Rowayton's vibrant amenities.

34 Nearwater Rd, Norwalk
6 Berry Ln, Darien
$5,025,000
6 Beds ⋅ 3 Baths ⋅ 24213301 MLS
There is a rare kind of magic when classic architecture meets a modern, artistic eye. Privately tucked at the end of a quiet cul-de-sac in Tokeneke School District. This stunning six-bedroom center-hall Colonial is surrounded by extraordinary grounds reminiscent of a private botanical garden. Mature specimen trees, sculpted greenery, flowering perennials and winding bluestone pathways create a breathtaking landscape in every season. Inside, sophisticated interiors blend timeless elegance with modern style. Sun-filled rooms, oversized windows, bespoke finishes and designer outdoor lighting frame spectacular garden views throughout. A beautifully remodeled eat-in kitchen serves as the heart of the home, flowing effortlessly into gracious living and entertaining spaces. Outdoors, an infinity-edge gunite pool and spa take center stage, surrounded by expansive bluestone terraces for dining, lounging and entertaining. A dedicated fire pit gathering area adds another enchanting dimension to this remarkable setting. Lush, mature landscaping provides exceptional privacy, creating a true resort-like retreat. Steps from Five Mile River, Rowayton and coastal Darien, this extraordinary property offers the perfect marriage of classic architecture, sophisticated design and unforgettable indoor-outdoor living. An exceptional property with the added luxury of flexibility, offering generous possibilities for future expansion.

6 Berry Ln, Darien
9 Flicker Ln, Norwalk
$5,000,000
5 Beds ⋅ 8 Baths ⋅ 24153974 MLS
Tucked along one of Rowayton's sweetest and most peaceful streets, 9 Flicker Lane is a brand-new home designed for real life. Step inside through the front door or slip in through the mudroom off the two-car garage, where daily comings and goings feel effortless. The main level balances refinement with comfort. A proper dining room and living room for when the occasion calls, alongside an easygoing family room that spills into the breakfast area and kitchen, complete with an oversized island and generous pantry. A private study and two powder rooms round out the floor. Upstairs, the primary suite feels like its own retreat, with a sitting area, dual walk-in closets, and a spacious bath designed to unwind in. Three additional bedrooms each enjoy their own en suite. The third floor offers a tucked-away bedroom/bath and play space, while the lower level is thoughtfully laid out to accommodate two separate rooms, ideal for a gym and media room, or whatever suits your needs. Outside, a newly built pool, wide patio with outdoor fireplace, and ample yard create a setting made for summer afternoons and evening gatherings. A rare find in Rowayton - a beautifully built home with real space to live, a pool to enjoy, and outdoor space to match.

9 Flicker Ln, Norwalk
19 Orchard Ln, New Canaan
$4,999,999
6 Beds ⋅ 8 Baths ⋅ 24206656 MLS
THIS IS THE ONE YOU'VE BEEN WAITING FOR! Under construction only 4 weeks from completion date. Brand new construction opportunity by highly regarded luxury builder Lecher Development. Prime in town location on a very quiet cul-de-sac. This exceptional home offers 6800 SF of high quality finishes, light-filled, living space across four finished levels. Highlights include: Gourmet Kitchen: A state-of-the-art kitchen featuring a large center island, premium stainless steel appliances, and an open layout that flows seamlessly into the family room with a fireplace and French doors leading to a covered porch. Flexible Main-Level Living: The first floor includes a private main floor space that can serve as a home office or sixth bedroom, complete with a full bath. Finished Third Floor: Ideal for a second office, playroom, guest suite, or au pair quarters. Spacious Lower Level: Featuring 10-foot ceilings, bath, plenty of options to create the perfect gym, media room, playroom, or additional recreation space. Generous Ceiling Heights: 9-foot ceilings on the main and second floors enhance the home's open, airy feel. Additional amenities include a 24-KW generator, zoned heating and cooling, town water and natural gas. Set on a level property with a designated pool site, this home combines luxury, comfort, and customization in an unbeatable location. Don't miss the opportunity to make this exceptional property your dream home

19 Orchard Ln, New Canaan
3 Canfield Xing, Norwalk
$4,950,000
6 Beds ⋅ 7 Baths ⋅ 24173339 MLS
Hidden behind Shorehaven Country Club in a gated waterfront enclave, 3 Canfield Crossing offers the rare opportunity to enjoy WATERFRONT LIVING in a NATURALLY PROTECTED WATERFRONT SETTING. Thoughtfully reimagined and extensively updated, the property combines timeless coastal design with the peace of mind of significant recent improvements, including a BRAND NEW CEDAR ROOF, new windows, several new mechanical systems, a new pool heater, and an entirely new chef's kitchen with custom cabinetry and premium appliances. Designed to embrace its waterfront setting, nearly every room captures views of the ever-changing tides. A NanaWall opens the newly renovated kitchen and living areas directly to the expansive waterfront terrace and infinity-edge pool, creating an effortless connection between indoors and out. With four finished levels connected by elevator, six ensuite bedrooms, including two separate guest or au pair opportunities, the home offers exceptional flexibility for everyday living and entertaining. Kayak or paddle board directly from your backyard, spend an afternoon at nearby Shorehaven Country Club, or enjoy the restaurants and amenities of Westport, Rowayton, and South Norwalk just minutes away. Private, protected, extensively updated, and directly on the water, 3 Canfield Crossing delivers a distinctive Fairfield County waterfront lifestyle without sacrificing the comfort, space, and convenience of a substantial year-round residence.

3 Canfield Xing, Norwalk
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
19 Mortar Rock Rd, Westport
$4,699,000
6 Beds ⋅ 8 Baths ⋅ 24174833 MLS
Stunning modern transitional home built by Compo Luxury Homes in 2024 and ideally located just minutes to downtown Westport, Compo Beach, and the train. Set on .65 acres with city water, sewer, and natural gas, this beautifully designed residence offers over 8,000 square feet across four finished levels with 6 bedrooms, 6 full and 2 half baths. The open floor plan features a chef's kitchen with high-end appliances, spacious living and entertaining areas, and a luxurious primary suite. The walk-out lower level includes a full gym with natural light and additional flexible space for recreation or guests, while the finished third floor offers ideal space for an office( or guest room), bonus room and full bath. Outdoor living includes a covered porch, stone patio, an outdoor shower, and a 16' x 32' heated gunite pool with automatic cover. Additional highlights include wide-plank floors, custom millwork, a whole-house generator, EV chargers, and a three-car garage, all in the sought-after Westport school district.

19 Mortar Rock Rd, Westport
1421 Oenoke Rdg, New Canaan
$4,595,000
7 Beds ⋅ 10 Baths ⋅ 24163175 MLS
Beyond a private gated entrance and sweeping circular drive lies a 2.5-acre sanctuary that redefines New Canaan luxury. Originally envisioned by Douglas Carter Architects and recently reimagined by its designer-owner, this estate seamlessly merges architectural pedigree with contemporary soul. The residence spans four finished levels, where soaring ceilings and walls of glass invite the lush landscape inside. At the heart of the home, a newly updated gourmet kitchen serves as a culinary showpiece. The primary suite is a true retreat, offering a private balcony, fireplace, and the rare luxury of dual bathrooms. Each of the six bedrooms in the main house features an ensuite bath, ensuring absolute privacy for family and guests alike. The amenities rival the world's finest resorts: a walk-out lower level equipped with a theater and wine room, and a 30x50 lagoon-style pool. The 2020-built pool house (700+ sq. ft.) provides a full guest experience with its own kitchen, bath, and flexible sleeping quarters-all just five minutes from the boutiques and bistros of New Canaan's vibrant village center.

1421 Oenoke Rdg, New Canaan
Stamford
$4,500,000
10 Beds ⋅ 10 Baths ⋅ 24026683 MLS
Enter a world of opulent privacy on nearly twenty-five acres of pristine countryside, boasting five acres of serene lakes, elegant stone bridge, and expansive manicured lawns that cradle an entire valley just 45 miles from NYC! Discover a lavish retreat comprising of four distinct residences: a magnificent five-bedroom, four-bathroom main estate, a charming two-bedroom, two-bathroom guest cottage, a sophisticated two-bedroom, one-bathroom carriage house complete with a heated three-car garage, and a stylish one-bedroom, one-bathroom log cabin pool house overlooking a 20x50 heated saltwater pool. Additionally, luxuriate in a cozy "writers cabin," with a majestic fireplace. The compound also has a versatile storage barn with separate private driveway access, and a dog kennel. The property is artfully situated amidst majestic oak trees and vibrant flowering shrubs, adorned with professionally landscaped stone terraces, walls, and scenic viewpoints, featuring multiple rose and mixed flower gardens, an organic vegetable garden, and a host of other exquisite amenities. Stroll through this picturesque sanctuary of unmatched serenity - a truly enchanting haven of natural beauty and modern comforts.

Stamford
897 Sport Hill Rd, Easton
$4,500,000
170626307 MLS
Large estate piece, gentleman's farm or amazing opportunity to create a signature subdivision. A truly beautiful property in the heart of bucolic Easton. Feels like you're in Litchfield County but easily accessible to downtown Westport, Southport and Fairfield amenities. Currently being taxed as a farm.

897 Sport Hill Rd, Easton
24 Oak Grove Pl, New Canaan
$4,395,000
6 Beds ⋅ 8 Baths ⋅ 24207918 MLS
Enjoy the best of New Canaan living from this stunning new construction home, tucked along a quiet private lane yet just a short walk to schools, town, train and park. Set on a beautifully landscaped .57-acre property, the expansive, flat backyard-with pool and spa-is a true rarity this close to town. Designed for effortless everyday living and entertaining, the main level centers around a chef's kitchen with quartzite countertops, Thermador appliances, an oversized island and light-filled breakfast area, flowing into the family room and out to covered outdoor living, granite patio and summer kitchen. A butler's pantry/bar serves the formal dining room and living spaces, making entertaining easy. More than 6,700 square feet across four levels offers room for everyone, including a flexible office/guest suite, primary retreat with radiant-heated spa bath, three en-suite bedrooms, third-floor bedroom and lounge with full bath, and lower level with space for fitness, play, sauna and a guest or au-pair suite. Walk to town, spend summer days by the pool and enjoy exceptional space and privacy-all with the ease of in-town living. Ready for move-in by mid-October!

24 Oak Grove Pl, New Canaan
16 Orchard Ln, New Canaan
$4,395,000
5 Beds ⋅ 6 Baths ⋅ 24205057 MLS
Custom construction meets effortless in-town living at 16 Orchard Lane, a 2019 HOBI Award winner for Best In-Town Custom Home. Built by acclaimed New Canaan builder RR Builders, the residence reflects a level of craftsmanship and consideration evident throughout, from the architectural detailing and carefully selected materials to the integrated systems and sophisticated mechanicals. A gracious entry introduces interiors defined by soaring ceilings, oversized windows and abundant natural light. Wide-plank white oak floors, custom cabinetry and substantial architectural detailing bring warmth and character, while generously scaled rooms and an easy, connected flow allow the home to feel both substantial and comfortable. At the heart of the home, the chef's kitchen features custom cabinetry, premium appliances and an oversized gathering island, opening naturally to the family room, dining area and rear porch. A generous pantry, functional back hall and extensive built-in storage bring organization and purpose to everyday living. Four finished levels provide exceptional flexibility. The primary suite features a dramatic vaulted ceiling and three exposures, complemented by a generous walk-in closet and bath with radiant heat, steam shower and soaking tub. The finished third floor offers additional airy, flexible space, while oversized windows bring unexpected natural light to the lower level, with recreation space and a dedicated gym.

16 Orchard Ln, New Canaan
5 Franklin Ave, Westport
$4,299,000
5 Beds ⋅ 6 Baths ⋅ 24115906 MLS
Nestled in one of Westport's most desirable walk-to-town neighborhoods, this exceptional new construction home combines timeless charm with modern luxury. Designed by acclaimed architect Judith Larson and crafted by trusted builder Redcoat Homes, this residence offers the perfect balance of style and functionality. Located on a level third-acre on a quiet cul-de-sac, the property is beautifully landscaped with a gunite pool. With 5 bedrooms, 6 full bathrooms, and four finished levels, the home is ideal for both family living and entertaining. An expansive, open floor plan is accentuated by Redcoat Homes' signature oversized windows and doors, flooding the space with natural light. The high-end finishes throughout elevate the home's sophisticated yet welcoming ambiance. A stunning chef's kitchen, a spacious home office, 1 fireplace, and generous living and dining areas make this home perfect for modern living. The lush backyard is an entertainer's dream, featuring a large bluestone patio with a built-in grill ideal for year-round gatherings. Enjoy the convenience of being moments away from Westport's renowned schools, Compo Beach, and the town's vibrant shops and restaurants. This home offers both exceptional luxury and a prime location for an unmatched lifestyle.

5 Franklin Ave, Westport
5 Hunter St, Greenwich
$4,195,000
6 Beds ⋅ 7 Baths ⋅ 24207811 MLS
Introducing a newly constructed Contemporary Colonial, by Alfieri Enterprises, that captures the essence of Old Greenwich living offering a seamless blend of classic architecture and modern design on a quiet cul-de-sac near schools, shops and the train. Defined by extraordinary craftsmanship, custom details and curated finishes in a stunning 6,000 sq. ft. home. Great for entertaining in open plan chef's kitchen, breakfast room with doors to expansive deck, family room and main level en-suite bedroom/office. Upstairs boasts an enviable primary suite retreat with spa bath, custom walk-in closets, an additional en-suite bedroom and two bedrooms connected by Jack/Jill bath. Top floor media/rec room and a guest en-suite bedroom, and the lower level offers a flex space for gym/gaming, half bath and storage complete this offering. With possible pool site.

5 Hunter St, Greenwich

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