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119 Proprietors Xing, New Canaan
$6,550,000
6 Beds ⋅ 10 Baths ⋅ 24156735 MLS
119 Proprietors Crossing is an entertainer's dream, featuring stunning architecture by James E. Gearity. Nestled on four private acres, this six-bedroom estate blends timeless elegance with modern luxury. A private drive leads to an elegant fountain, setting an unforgettable tone. Inside, a soaring foyer showcases a dramatic Baccarat chandelier and seven fireplaces, enhancing the warm atmosphere. Spacious entertaining areas flow seamlessly to a tranquil terrace. The heart of the home includes a chef's kitchen that opens to a Great Room with a remarkable 35.5 foot vaulted ceiling, centered around a large quartz island with integrated audio. A formal dining room beneath another Baccarat chandelier sets the stage for memorable gatherings. The West wing hosts the primary suite, featuring a cozy retreat and a study with a hidden staircase leading to a gym and an 800-square-foot dressing room. An adjacent Junior Primary Suite has its own entrance and living area. Upstairs, four additional bedrooms include two ensuite and two with a jack-and-jill bath. The finished lower level boasts a media room, fitness center, and wine cellar. Outdoors, curated grounds offer a dining pavilion, outdoor kitchen, and a newly constructed pool and spa, with space for a tennis/pickle-ball court. Engineered for efficiency, the estate features commercial-grade systems, radiant heat, and a rare Welsh slate roof. A four-car garage and an elevator service complete this exceptional offering.

119 Proprietors Xing, New Canaan

28 Old Farm Rd, Darien
$6,510,000
5 Beds ⋅ 8 Baths ⋅ 24162725 MLS
Set on a beautifully landscaped and expansive property, 28 Old Farm Road offers a rare blend of refined elegance and modern comfort. Thoughtfully designed with impeccable attention to detail, the residence features five spacious bedrooms, each with its own en suite bathroom. An exceptional primary suite was designed as a private retreat. This serene space includes a separate lounge area, an oversized walk-in closet, and a spa-inspired bathroom with views of a manicured, sprawling lawn and a beautifully designed pool complete with a safety cover, ideal for both relaxation and entertaining. Every outdoor element has been carefully curated to enhance the sense of luxury and privacy. Inside, the home has been recently reimagined by renowned designer Naomi Stroh, whose sophisticated vision brings a fresh, elevated aesthetic to every room. The finished lower level offers versatile space perfect for recreation, a home gym, or additional living, all complemented by ample storage. The interiors seamlessly blend timeless style with contemporary finishes, resulting in a warm yet striking living environment. This is a rare opportunity to own a move-in-ready, design-forward home in one of Darien's most desirable locations in the private Tokeneke Association.

28 Old Farm Rd, Darien

10 Cross Rd, Darien
$6,500,000
6 Beds ⋅ 8 Baths ⋅ 24153454 MLS
10 Cross Road is custom built and thoughtfully designed by Louise Brooks & Artisan Builders. No expense has been spared...extensive millwork and moldings, soaring 10-foot and cathedral ceilings! In the heart of the private Tokeneke Assoc. on a hilltop with southern exposure, multiple French doors create a seamless indoor-outdoor lifestyle. Enjoy a custom pool, spa, & waterfall beautifully integrated into lush gardens and refined hardscaping. Meticulously maintained, this private backyard offers a true oasis - you won't want to leave! A chef's kitchen appointed with Wolf and Sub-Zero appliances, a dble. island and a cozy dining area with expansive windows and fireplace is open to a grand family room. Formal living and dining room with entertaining butlers parlor and mature office complete the main floor. Upstairs, the spacious primary suite offers a sitting area, walk-in closets and serene bathroom. 3 ensuite bedrooms provide luxurious accommodations. The 3rd floor offers a large playroom space with 2 adjacent bedrooms sharing a jack-and-jill bathroom. Additional amenities include a 3-car heated garage, theater, gym, sauna and partial heated driveway. Many recent improvements - including a new cedar roof, newly paved driveway, full exterior painting, new front stone wall, and pool enhancements - further elevate the home's turnkey appeal. Come experience the beauty, history, and prestige of Tokeneke at its finest, a private coastal community just a short distance from town.

10 Cross Rd, Darien

7 Hearthstone Dr, Greenwich
$6,302,500
5 Beds ⋅ 6 Baths ⋅ 24183996 MLS
Exceptional HOBI Award-winning shingle-style home by Argus Development on one of Riverside's most coveted streets. Thoughtfully designed for everyday living and entertaining, this home features a chef's kitchen with oversized island and banquette, family room with custom built-ins and fireplace, private study, mudroom, luxurious primary suite, and en-suite baths for every bedroom. French doors open to a covered bluestone patio overlooking a private backyard retreat with pool and spa. Renovated in 2022, the finished lower level offers a bedroom suite, full bath, kitchenette, laundry, two fireplaces, hardwood floors, and cedar closet. Minutes from schools, train, Old Greenwich Village and Tod's Point. Riverside is a lifestyle.

7 Hearthstone Dr, Greenwich

211 Oenoke Rdg, New Canaan
$6,250,000
5 Beds ⋅ 7 Baths ⋅ 24174226 MLS
Located on prestigious Oenoke Ridge in the heart of New Canaan, this spectacular modern farmhouse represents the pinnacle of luxury living, offering exceptional craftsmanship, designer finishes, and every high-end amenity imaginable. Perfectly positioned just moments from the New Canaan Nature Center, scenic walking trails, and a short stroll via sidewalks to the Village's renowned restaurants, boutiques, and theater, the location is truly unparalleled. Meticulously maintained and beautifully appointed, the home is defined by airy, light-filled interiors and an exceptional open-concept floor plan designed for both sophisticated entertaining and comfortable everyday living. A gracious wraparound porch welcomes you into elegant interiors featuring a stunning foyer, expansive living room with gas fireplace, and a state-of-the-art chef's kitchen with oversized center island, premium appliances, butler's pantry, and custom bar area. The adjoining family room, anchored by a second fireplace, opens through French doors to the resort-style grounds beyond. Designed for seamless indoor-outdoor living, the private backyard is a true sanctuary, featuring a spectacular Gunite pool and spa surrounded by lush professional landscaping. A spacious stone terrace offers multiple seating and lounging areas, while the fully equipped outdoor kitchen creates the ideal setting for alfresco dining and entertaining. The luxurious primary suite is a serene retreat with vaulted ceilings, a spa-inspired

211 Oenoke Rdg, New Canaan

386 North St, Greenwich
$6,250,000
5 Beds ⋅ 9 Baths ⋅ 24156530 MLS
This magnificent 9,974 sq ft estate seamlessly blends grand scale, craftsmanship, and modern luxury. Set on 2.3 parklike acres in coveted Mid-Country Greenwich, just minutes from town, the home makes an immediate impression with a soaring two-story foyer introducing exquisitely appointed interiors defined by custom details and rich materials. Updated in 2026, the show stopping kitchen features top-of-the-line appliances, bespoke cabinetry, and a dramatic quartzite center island, opening to a vaulted great room with fireplace and effortless access to the pool terrace. Six spacious ensuite bedrooms include a luxurious primary retreat with sitting room, 2 private offices, fireplace, spa-like marble bath with steam shower and soaking tub, and expansive walk-in closets. A private in-law or nanny suite provides flexible living options. The finished lower level features a 2,000-bottle temperature-controlled wine cellar with tasting bar, recreation space with putting green, sauna, fitness area and ample storage. Outdoors, enjoy a 55-foot pool, spa, 3,000 sq ft sun deck, BBQ island, and sweeping lawns. Additional enhancements include a redesigned laundry room, upgraded lighting throughout, refinished floors, freshly painted interiors, smart home and automation upgrades, state-of-the art security system, new HVAC systems and a modernized garage. An iconic residence where grandeur meets exceptional craftsmanship and refined living.

386 North St, Greenwich

38 Three Wells Ln, Darien
$6,100,000
5 Beds ⋅ 7 Baths ⋅ 24173379 MLS
Set on two private acres in coveted northern Darien, this exceptional Colonial offers refined living, timeless design, and superior craftsmanship throughout. A gracious living room with fireplace provides a warm and sophisticated gathering space, while the formal dining room is perfectly complemented by an adjacent butler's pantry, ideal for seamless entertaining. A richly appointed study/library with its own fireplace offers a quiet and distinguished retreat.At the heart of the home, the expansive kitchen and family room open effortlessly to the spectacular outdoor living areas, creating the perfect setting for both everyday living and large-scale entertaining. Outside, the grounds have been transformed into a true private retreat featuring a pool, renovated pool house, outdoor kitchen, BBQ pit, pergola and fire pit - offering an exceptional backdrop for entertaining and year-round enjoyment. The fully remodeled lower level is thoughtfully designed for recreation and relaxation, featuring a custom theater room, walk-in wine cellar, and luxurious sauna. This remarkable property seamlessly combines luxury, comfort, and modern functionality in one of Darien's most desirable locations.

38 Three Wells Ln, Darien

28 Ferry Ln E, Westport
$6,100,000
5 Beds ⋅ 9 Baths ⋅ 24175264 MLS
Looking for a sensational home just a short walk to the beach, Longshore, train, and restaurants in trendy Saugatuck? This exceptional home by Walter Mattera is a masterclass in blending traditional design with contemporary style. Expansive interiors feature grand gathering spaces that flow naturally into intimate retreats, creating a home equally suited for entertaining and everyday living. Thoughtfully designed across 4 floors, the home offers 5 bedrooms, 6 full/3 half baths. A gracious foyer opens to large scale living spaces, including an oversized kitchen with breakfast nook that connects seamlessly to the family room with a striking stone fireplace. Formal dining with butlers pantry, private office, and multiple indoor outdoor connections create a dynamic and inviting environment. The second level is highlighted by the luxurious primary suite featuring a fireplace, spa inspired bath, and boutique caliber closet designed as a calming retreat. Four additional en suite bedrooms, laundry, and bonus room complete the level. Third floor and walk out lower level recreation spaces reflect a modern approach to luxury where work, wellness, and entertainment coexist effortlessly. Outside, the chic and ethereal setting continues with a pool, spa, covered patio, fireplace, and expansive bluestone terrace that seamlessly integrate indoor and outdoor living. Every detail has been carefully considered to deliver comfort, sophistication, privacy, and connection to the best of Westport.

28 Ferry Ln E, Westport

304 Brookside Rd, Darien
$6,095,000
6 Beds ⋅ 8 Baths ⋅ 24158797 MLS
Architecturally stunning six-bedroom Colonial graces 2.29 level acres designed for resort-style living with pool, pool house, outdoor shower, stone terrace with kitchen & garden masterfully built in 2014. Beautifully appointed 6,117 sq ft interior brimming with exquisite details including high coffered ceilings, transom topped doorways & box molding. Striking double height foyer introduces ideal floor plan, perfect for everyday living & entertaining, anchored by chef's marble-clad kitchen which opens to large family room with fireplace flanked by doors to magnificent screened porch with industrial grade heaters & fireplace. Elegant dining room with fully equipped butler's pantry, stylish living room & office both with fireplaces, mudroom & two powder rooms round out this level. Sumptuous primary suite with fireplace, his/her walk-in closets, deluxe bath with radiant heated floors; two en-suite bedrooms, two bedrooms with Jack/Jill bath, homework area, laundry room comprise 2nd floor. Generous lower-level boasts media room with projector, game room, wine room with wine refrigerator, bedroom, full bath & generator. Unfinished top floor features ample storage & unlimited potential. Outdoor Kalamazoo gourmet kitchen is fitted with grill, pizza oven, smoker & kegerators. Incredible pool house (add'l 860 sq ft) includes custom kitchenette, half bath with outdoor shower & loft. Ideally located on professionally landscaped, private lot with fenced-in yard near all Darien offers.

304 Brookside Rd, Darien

59 Sail Harbour Dr, New Fairfield
$6,050,000
6 Beds ⋅ 9 Baths ⋅ 24166572 MLS
An Exceptional Renovated Waterfront Retreat, set majestically on 5.19 private acs. offers 400' of frontage on Candlewood Lake complete w/private dock & sand beach. Enticing outdoor spaces include the heated, in-ground pool w/paving stone patio overlooking the lake, An expansive 20 X 40 deck on main level & a walk-out, lower level to a stone patio w/fire pit; ideal for summer entertaining! Approach the entry through glass doors to the 2 story foyer w/turn stair & modern lighting. French doors on the left, open to the formal dining room w/built ins, custom light fixtures & moldings. An expansive 38 ft great room w/marble fireplace, surrounded by windows exudes a warm, comfortable ambiance. A second stone fireplace warms the family room, ideal for TV viewing, reading or just relaxing. Custom millwork, built-ins, hardwood floors & a plethora of windows, showcase the views from every angle. The Chef's kitchen boasts Wolf appliances, marble countertops, wet bar & stunning center island plus a designer range hood! The enticing primary suite hosts his/her bathrooms, WIC, built-ins & loft w/ views. Three other designer bedrooms offer a Jack & Jill bath & an en-suite. An expansive lower level boasts 15 ft. ceilings, recreation space with stone fireplace, half bath, wet bar, bunk room w/full bath & a 5th en suite bedroom w/full bath. An additional full bath for future movie theater, 3 laundries, 3 car gar. plus SHC amenities:tennis, community beach, clubhouse. A one of a kind lake find!

59 Sail Harbour Dr, New Fairfield

250 Davenport Dr, Stamford
$6,014,250
2 Beds ⋅ 3 Baths ⋅ 24174434 MLS
Set on 1.68 extraordinary acres at the end of Davenport Drive, this waterfront peninsula property offers a rare chance to reimagine and transform an existing residence into a custom coastal estate. Offered for the first time in 76 years, the home is surrounded by water on three sides, providing sweeping 180-degree eastern, southern, and western exposures that fill the interiors with natural light and frame panoramic views from sunrise through sunset. The current residence offers a blank canvas for the next owner to bring their vision to life. Whether through a comprehensive restoration or a complete reconfiguration, the opportunity exists to create a home that fully realizes the potential of this remarkable setting. With a completed survey and feasibility study already in place, much of the initial groundwork has been done. The property also offers the best of both worlds - privacy and seclusion at the end of a quiet road in the Southfield Association and extreme proximity to downtown Stamford and Old Greenwich - granting easy access to restaurants, shopping, beaches, and train service. It's a rare opportunity to reimagine a home that is placed on one of the most special pieces of property in Fairfield County.

250 Davenport Dr, Stamford

22 Apple Tree Trl, Westport
$5,995,000
5 Beds ⋅ 5 Baths ⋅ 24158799 MLS
Located on a quiet private lane just two blocks from Compo Beach, this newly built coastal residence at 22 Appletree Trail offers a rare combination of modern craftsmanship, thoughtful design, and effortless beach living in the heart of Westport. Spanning approximately 4,791 sq ft of living space, the home blends timeless architectural elements with refined contemporary finishes. White oak floors, soaring ceilings, and custom Italian cabinetry create a warm and sophisticated interior. The chef's kitchen features L'Ottocento cabinetry, Thermador appliances, and Compac Quartz surfaces, complemented by a fully equipped butler's pantry with a second dishwasher and wine refrigeration. An open-concept family room with a sleek linear gas fireplace flows seamlessly to the covered outdoor terrace overlooking the heated pool and landscaped grounds-perfect for both quiet evenings and entertaining. Upstairs, vaulted bedrooms include fully furnished custom closets. A sun-filled lounge opens to a private rooftop deck with a gas fireplace and seasonal views of Long Island Sound. The primary suite offers a private terrace, dual walk-in closets with custom Italian millwork, and a spa-inspired bath designed for relaxation. Set moments from the shoreline while offering easy access to Manhattan via train, this newly completed residence presents a rare opportunity to enjoy modern coastal living in one of Westport's most desirable neighborhoods.

22 Apple Tree Trl, Westport

164 Stanwich Rd, Greenwich
$5,950,000
5 Beds ⋅ 6 Baths ⋅ 24159056 MLS
Welcome to this exquisitely updated Colonial on 1.16 landscaped acres near Greenwich Country Club and minutes from town. A grand foyer with gleaming hardwood floors and sweeping staircase introduces the elegant interior. The main level includes a formal living room, dining room, two studies, and a gourmet kitchen with Wolf appliances, Palissandro marble, Thermador coffee station, a custom wet bar and a 425-bottle wine cellar. The kitchen opens to a family room with fireplace and French doors. Upstairs, the primary suite offers a sitting room, luxurious bath, office, and fireplace. Four additional bedrooms complete the level. Enjoy 3,000+ sq ft of terrace, heated saltwater pool, Viking grill, and a pavilion with sound system. The Heated and air conditioned 4-car garage adds storage and versatility.

164 Stanwich Rd, Greenwich

143 Oenoke Rdg, New Canaan
$5,900,000
5 Beds ⋅ 8 Baths ⋅ 24135729 MLS
Experience the pinnacle of sophisticated living in this extraordinary estate by renowned builder Kaali-Nagy, perfectly situated within walking distance to the village, train, and nature center. The residence showcases impeccable craftsmanship throughout, defined by extensive custom moldings, intricate wainscoting, and an effortless flow designed for both grand entertaining and intimate daily life. At the heart of the home, a gourmet chef's kitchen features a sun-drenched breakfast room and a butler's pantry, with French doors opening to one of three private terraces for seamless indoor-outdoor transitions. Designed to elevate everyday living, the home also boasts a fully equipped private home gym, an inviting billiards room and media area, perfect for relaxed gatherings.The private property is equally impressive, boasting a spectacular 20 x 40 heated gunite pool surrounded by professionally designed, mature landscaping that creates a serene and secluded outdoor retreat-ideal for summer entertaining or peaceful relaxation. This thoughtfully designed floor plan includes five spacious ensuite bedrooms, each boasting its own walk-in closet, ensuring unparalleled comfort for family and guests alike. Complete with the modern convenience of a private elevator serving the home's multiple levels, this property offers a rare blend of timeless architectural detail, exceptional amenities, and a premier "walk-to-everything" location.

143 Oenoke Rdg, New Canaan

1 Bramble Ln, Greenwich
$5,900,000
5 Beds ⋅ 7 Baths ⋅ 24157206 MLS
Exceptional custom built 5 bedroom stone and shingle home in a sought-after Riverside location. Across from Riverside school/playground and one block to Eastern Middle School, this beautifully designed and professionally decorated home showcases a two-story foyer, well proportioned and light-filled living spaces, high ceilings, exceptional finishes and craftsmanship. Spacious chef's kitchen has stainless steel appliances and opens to a lovely family room w/fireplace. Seamless access to the stone patio and outside kitchen overlooks the new Shoreline pool and level private yard. Elegant primary suite plus 4 generous sized bedrooms upstairs. The expansive lower level has a large recreation area, gym and bonus room with bath. Extras: 6 fireplaces, 3 car garage, covered front porch. Turnkey!

1 Bramble Ln, Greenwich

140 Stoneleigh Rd, New Canaan
$5,800,000
6 Beds ⋅ 10 Baths ⋅ 24167662 MLS
Discover the epitome of timeless luxury in this magnificent Colonial Chateau-style residence. Perfectly situated on two flat, meticulously landscaped acres in a coveted walking neighborhood, this home offers unparalleled privacy while remaining just moments from town and top-rated schools. This quiet, no-cut-through street is a haven for outdoor enthusiasts, offering exceptional bike riding and walking routes right from your door. The active neighborhood association fosters a true sense of community-think spirited trick-or-treating, seasonal gatherings, and friendly faces at every turn. Enjoy the best of both worlds: peaceful residential living with convenient access to prime roadways for an easy commute. The interior is a masterful blend of elegance and comfort, featuring six spacious en suite bedrooms and an astounding eight indoor fireplaces that create warmth and ambiance throughout. Designed for grand entertaining and modern family living, the home boasts multiple family rooms, ensuring ample space for every occasion. Indulge your passions in the dedicated wine cellar and the custom-designed sports den. The sophisticated primary level flows seamlessly to the breathtaking exterior amenities, which include a built-in pool for summer relaxation and a beautiful outdoor fireplace for year-round enjoyment. Completing this exceptional estate are four spacious garage bays, providing abundant storage and convenience.

140 Stoneleigh Rd, New Canaan

9 Pond Edge Rd, Westport
$5,775,000
6 Beds ⋅ 7 Baths ⋅ 24143533 MLS
Experience the pinnacle of Compo Beach living at 9 Pond Edge Road, a rare coastal sanctuary offering immediate beach access with the peace of mind of an elevated, flood-safe setting. Spanning 6,100 square feet across four impeccably finished levels, this 6-bedroom home is designed for effortless entertaining and everyday relaxation. Sunlight fills the open great room (with WBF) and dining area, where a wall of French doors opens to a private backyard oasis featuring a heated gunite pool, stone patio, and built-in BBQ, all surrounded by mature landscaping. A cozy living room with a gas fireplace provides the perfect setting for intimate gatherings or quiet evenings at home. At the heart of the home is the eat-in Chef's Kitchen, complete with luxury appliances, two dishwashers, three ovens, and an oversized center island. A flexible main-level suite offers ideal space for an executive office or guest accommodations. The second floor showcases a serene primary suite with a gas fireplace, dual dressing rooms, and a spa-inspired bath, along with three additional en-suite bedrooms and a laundry room. The third level features a secluded guest suite with private balcony and a skylight-filled bath. The lower level is a destination of its own, offering a home theater, dedicated gym, recreation room, and full bath with direct access to the pool. Complete with a whole-home generator and attached garage, this turn-key property delivers laid-back luxury just moments from the sand.

9 Pond Edge Rd, Westport

6 Twin Circle Dr, Westport
$5,700,000
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

757 Oenoke Rdg, New Canaan
$5,700,000
7 Beds ⋅ 8 Baths ⋅ 24147831 MLS
The "Legacy Estate" An Oenoke Ridge Masterpiece: The main brick residence captures the essence of Gilded Age elegance with 10-12 ft ceilings, eight fireplaces, a classic wrap-around-porch, and a porte-cochere. Spanning four finished levels, the main residence seamlessly blends original character with a significant three-story addition completed in 2012. The newer wing features a spacious Smallbone gourmet kitchen, sun-drenched breakfast room, large working pantry, 2-sided fireplace, large center island fit for a master chef and an adjacent family room all designed for casual living and effortless entertaining. The main residence includes a luxurious owner suite with fireplace, balcony, marble bath and 2 walk-in-closets. There are six additional bedrooms on the upper levels. The home is rich with architectural character throughout. The property also includes: - Three Historic Barns: Versatile spaces for collectors, animal lovers, gardeners or car enthusiasts. Grounds: Set high on the ridge, 4 pastoral acres with an identified pool site, multiple gardens, and rolling lawns. Own a piece of New Canaan history on Oenoke Ridge.

757 Oenoke Rdg, New Canaan

316 Mansfield Ave, Darien
$5,625,000
5 Beds ⋅ 7 Baths ⋅ 24167771 MLS
Just in time for summer-this exceptional property offers the ultimate in luxury living and outdoor enjoyment. Imagine relaxing poolside by your new heated pool and spa, surrounded by beautifully landscaped grounds and sweeping views of the golf course. Inside, the home is equally impressive. The expansive primary suite is a true retreat, featuring a private sitting room that opens onto a deck overlooking the pool-perfect for morning coffee or evening unwinding. The suite also boasts a beautifully updated bath and two spacious walk-in closets. The second level is thoughtfully designed with four additional en-suite bedrooms and a versatile playroom, offering comfort and privacy for family and guests alike. At the heart of the home is a stunning new gourmet kitchen, outfitted with top-of-the-line appliances including a Wolf range, two Sub-Zero refrigerators, a separate freezer, and three dishwashers-an entertainer's dream. The lower level is equally striking, featuring an elite gym, a playroom, and abundant open space for recreation and play-perfect for entertaining, relaxing, or staying active without ever leaving home. This remarkable colonial seamlessly blends elegance, comfort, and modern convenience-perfect for making unforgettable summer memories and beyond.

316 Mansfield Ave, Darien

13 Edgehill Dr, Darien
$5,500,000
5 Beds ⋅ 5 Baths ⋅ 24171365 MLS
This Dockside home is a short paddle away from Five Mile River. Quietly iconic. Effortlessly cool. Live large without living complicated. This is the rare waterfront home that offers the lifestyle of a grand estate with the ease of a true lock-and-leave retreat. Set on just over an acre in the private Tokeneke Association it's designed for living well not maintaining endlessly. There are four private bedrooms in the main house and several places to kick back. Escape whenever you choose a weekend, a week, or all the days in between. Paddle over to Rowayton for lunch, entertain under the stars by the fire, or spend an afternoon with a great book by the pool. A private guest cottage with multiple sleep configurations offers family and friends their own retreat while preserving yours. Waterfront homes that live this effortlessly are incredibly rare. A manageable home, beautiful grounds, a dock, freeform pool, an abundant vegetable garden and even a chicken coop, all within the security of Tokeneke including optional home check-ins while you're away. Make coming and going completely carefree, an easy house, an extraordinary life.

13 Edgehill Dr, Darien

10 Debra Ln, Westport
$5,500,000
6 Beds ⋅ 9 Baths ⋅ 24131564 MLS
Stunning 6 Bedroom 9600SF (including all 4 levels) Colonial in the heart of Westport. Built by Bluewater Home Builders, this stunning custom residence is situated on a private cul-de-sac in the central Hunt Club area. The traditional design boasts exceptional interior details, including soaring ceilings, beamed and coffered accents, shiplap paneling, and sleek millwork throughout all finished levels. The state-of-the-art gourmet Kitchen flows seamlessly into the grand Family Room, both opening to a covered bluestone patio featuring a fireplace, remote-controlled phantom screens, and a built-in outdoor kitchen-perfect for entertaining.The 1st floor office also opens to the peaceful yard and Patio. A 20'x45' saltwater Pool with automatic cover and sun ledge add a resort-like touch, complemented by mature landscaping, a koi pond, multiple gathering areas and a fire pit. Luxurious Primary Suite offers a soaring 11' ceilings, a fireplace, dressing/sitting room, and a marble spa bath. Five additional en-suite Bedrooms provide ample space for family and guests. The finished Lower Level includes a Game Room, Media Room with stadium seating, Gym, Wine Center and an 6th Bedroom. Finished 3rd floor offers bunk beds for sleep overs, a stage, an art area, lounge,cedar closet & abundant storage. Modern amenities include a generator and Lutron lighting system throughout. Located on a perfect acre, this home combines elegance, comfort, and convenience-just moments from all Westport amenity.

10 Debra Ln, Westport

32 Burnham Hl, Westport
$5,450,000
6 Beds ⋅ 7 Baths ⋅ 24168754 MLS
Experience refined coastal living in this exceptional hilltop residence, just a short walk to Compo Beach. Built by celebrated Bluewater Home Builders, this stunning Nantucket-style home set on a rare & secluded .92-acre property on a quiet cul-de-sac is ideally positioned on one of the area's most prestigious & sought-after streets, offering an unparalleled blend of privacy & lifestyle. This home is surrounded by beautiful landscaped grounds and features a gunite pool, spa & water views of Mill Pond. Spanning 4 finished levels, the home offers 6 bedrooms, 7 baths, including 2 home offices-perfect for today's lifestyle. The grand foyer leads to the Dining Room with Butler's Pantry and the Living Room with fireplace. At the heart of the home is the Gourmet Kitchen with upscale appliances and an open floor plan to the Family Room. There is a screened in 3 season porch off the kitchen. On the second floor the luxurious Primary Suite features its own private office and a 2nd floor balcony with water views. 3 additional bedrooms are ensuite. A private third floor offers a bedroom, full bath and balcony ideal for guests, family or a secluded work space. The finished above ground walk-out lower level to the pool/patio is designed for both relaxation and fun, complete with a Playroom, Exercise Room, Bedroom, Full Bath, Wine Cellar, second laundry area and extensive storage. There is a full house generator. NO flood insurance is needed. Minutes to train station. Vacation year round.

32 Burnham Hl, Westport

1657 Fairfield Beach Rd Unit 1657, Fairfield
$5,410,000
4 Beds ⋅ 6 Baths ⋅ 24185816 MLS
Exceptional, one of a kind property, with direct beach frontage, panoramic views, inground pool, elevator, and a magnificent 2-story elliptical staircase to resemble a seashell. Best of all this home is better than new & FEMA compliant. The elevator extends from the garage to 3 floors more. The residence has 7 outdoor decks to enjoy breathtaking sunrises, sunsets, LI ferry and Penfield Lighthouse. Take long walks, enjoy the sandy beach, or sit and listen to the sound of the waves. The inground pool has a magnificent limestone decking. Highest quality craftmanship and woodworking throughout. The quartzite kitchen is exceptionally spacious to accommodate large gatherings with Subzero and Wolf double oven. A second galley kitchen has an extra DW, dbl sink, fridge/freezer, and custom cabinetry that includes a banquet with direct water dining views. The covered porch overlooks the pool and beach and has a glass fence surround. The 1st floor has an office/study. The 2nd floor features 3 BRs, 2 ensuite plus the primary w/ his and hers baths and sliders to lg viewing deck. 3rd floor adds 2000+ sq ft of addtl living space (not on field card) & replicates a ship potential for another BR. Your own private beach club has high ceilings, top quality construction and custom windows, and flexible living space for every occasion. Exceptional parking for up to 10 cars! This magnificent seaside home is like a private beach club in summer and a retreat oasis for all seasons. Opportunity awaits!

1657 Fairfield Beach Rd Unit 1657, Fairfield

9 Greenbrier Rd, Westport
$5,375,000
7 Beds ⋅ 9 Baths ⋅ 24112473 MLS
A RARE SECOND CHANCE. This estate drew multiple offers within days, then sellers pressed pause. With plans now finalized, it's back on the market. Charming. Unique. Soulful. These are the words the current owner uses to describe this exceptional estate-and from the moment you arrive, you'll understand why. Poised on 2.85 private acres, this exceptional estate seamlessly weaves timeless heritage with modern luxury. At its core: a preserved 1930 Frazier Peters stone cottage-now a 2-bed, 2-bath guest house. At its heart: a 2007 custom-built main residence by Coastal Construction, echoing Peters' signature stonework with scale and sophistication. Step inside and you'll understand why guests so often say, "Every room tells a story." A just-completed interior redesign has curated every finish, light fixture, and wall covering to create warmth and quiet elegance. The flow between rooms is not just open-it's meaningful, revealing itself gradually like a favorite novel. The barrel-ceilinged primary suite, sunlit kitchen, cozy living room, hidden reading nooks, and versatile third-floor retreat all invite you to live more slowly, more beautifully. A gym, media room, and music studio offer space to move, create, and unwind. Outside, a pool/spa, pool house, and terrace with fireplace and outdoor kitchen extend the experience. Offered fully furnished at an additional cost if desired. Where every detail invites you to live with intention, comfort and quiet luxury.

9 Greenbrier Rd, Westport

43 Rowayton Ave, Norwalk
$5,350,000
4 Beds ⋅ 3 Baths ⋅ 24162208 MLS
Set along the picturesque Five Mile River with its own private beach and dock, this exceptional waterfront home captures sweeping views of the Long Island Sound and unforgettable sunsets from multiple outdoor living spaces, including a terrace with a gas fireplace and two expansive decks. Located in the heart of the sought-after Rowayton Beach Association, the residence offers a bright, open floor plan with water views from nearly every room. Featuring four bedrooms and two-and-a-half baths, including a convenient first-floor primary suite, the home is in wonderful condition. Ideal for those looking to downsize without compromise, with the flexibility to expand for a larger lifestyle-all just a short walk to downtown Rowayton and its charming amenities.

43 Rowayton Ave, Norwalk

15 Roosevelt Rd, Westport
$5,300,000
4 Beds ⋅ 5 Baths ⋅ 24174513 MLS
An impeccable home in an incredible location! Just a stone's throw to Compo Beach, Ned Dimes Marina and Longshore Club Park, this gorgeous 4 bedroom, 4.5 bath modern Colonial with a pool is beach neighborhood perfection. The main floor is beautifully arranged, the family, dining area and kitchen span the back of the house creating a great room - with French doors to the patio and pool just beyond. The gorgeous kitchen is down in white oak, with a massive island, top appliances and smart storage. Gorgeous custom details throughout include built ins, dramatic modern millwork, sleek fireplaces and high end stone surfaces plus an elevator. Upstairs, the primary suite is a dream - a bright and airy bedroom, two walk in closets, and an oversized bath with soaking tub, steam shower and radient flooring. There are two additional bedrooms on the second floor, plus an office and laundry room. The third floor holds a bedroom and full bath. Tucked on a quiet side street steps to the water and all the Compo/Longshore area amenities like beach, boating, golf and tennis, while also being just a quick ride into town or to the train!

15 Roosevelt Rd, Westport

114 Adams Ln, New Canaan
$5,300,000
6 Beds ⋅ 10 Baths ⋅ 24169455 MLS
Experience timeless elegance and resort-style living in this extraordinary stone estate on 2+ spectacular acres overlooking a serene spring-fed pond with direct water access. Designed by architect Malcolm Robertson with interiors inspired by Rick Livingston Period Design, this home offers 9,369 SF of masterfully crafted living space blending architectural sophistication with modern luxury. Built in 2004, the home showcases Venetian plaster walls, cerused oak details, radiant heated stone floors, soaring ceilings, extensive custom millwork, and dramatic walls of glass framing breathtaking views of the pool, grounds, and pond. At the center of the home is a showstopping 3 story gourmet kitchen-a true culinary masterpiece-seamlessly blending architectural drama with top-tier functionality with limestone counters, oversized gathering island, and premium Miele, Wolf, Viking, and SubZero appliances. Designed for both grand entertaining and comfortable everyday living, the residence features 6 en-suite bedrooms, 8 full and 2 half baths, with spectacular first-floor primary suite with dressing rm and spa bath. Amenities incl media rm, billiard rm, sun rm, gym, professional office suite, Control4 smart home technology, surround sound, heated pool w/automatic cover, separate spa, Har-Tru tennis court, extensive landscape lighting, and beautifully manicured grounds. Rarely does a property of this caliber, privacy, and design become available just moments from town in a coveted location

114 Adams Ln, New Canaan

27 Hillsley Rd, Darien
$5,200,000
6 Beds ⋅ 6 Baths ⋅ 24175837 MLS
Exquisitely renovated center hall colonial set on two perfectly manicured acres at end of quiet, private cul-de-sac, offering exceptional space & timeless appeal for both everyday living & entertaining. Renovated in 2023 by ERI Building & Design, this stunning six-bedroom home with private office, four full & two half baths showcases impeccable craftsmanship & sophisticated design throughout. Dramatic open-concept kitchen features two oversized islands, walk-in pantry, Sub-Zero refrigerator & freezer, & an inviting breakfast area flowing seamlessly into soaring great room overlooking expansive rear lawn & tennis court with room for pool - perfect setting for gathering with family & friends. Light-filled sunroom provides ideal spot for relaxing with morning coffee while enjoying peaceful views of property. Designed for elegant entertaining, the home features gracious formal living room with fireplace, stunning bar & lounge area, wine pantry, & formal dining room with butler's pantry. Luxurious first-floor suite provides exceptional comfort & privacy for visitors. Upstairs luxurious primary suite with fireplace & spa-like ambiance, creates peaceful retreat. Four additional generously sized bedrooms feature beautifully appointed jack-jill baths. Private office just across hall creates ultimate work-from-home setting. Thoughtfully designed lower level provides flexible, ample space for gym or playroom. This truly exceptional home offering elegance & an unparalleled lifestyle.

27 Hillsley Rd, Darien

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