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276 Greenley Rd, New Canaan
$5,600,000
6 Beds ⋅ 7 Baths ⋅ 24141707 MLS
Nestled in one of Connecticut's most sought-after estate neighborhoods and just minutes from town, this spectacular 1939 Classic Colonial blends timeless elegance with every modern amenity. Set on nearly 5 bucolic acres of rolling lawns, perennial gardens, and mature trees, this pristine property offers unmatched privacy and beauty. The grand approach includes a stately driveway with a central fountain leading to an inviting paneled foyer. Inside, the gracious living room with fireplace and built-ins opens to a formal dining room that overlooks the magnificent grounds. The chef's kitchen, complete with eat-in area, is perfect for both everyday living and entertaining. Unique lifestyle features abound: a spacious game room with cigar ventilation ideal for cards or gatherings, a cozy wood-paneled office with extensive built-ins, and a secondary office featuring a charming circular window with a view of the sprawling front lawn. The luxurious primary suite offers a fireplace, dual walk-in closets, and a spa-inspired bath. Four additional bedrooms provide comfortable accommodations for family and guests. A modern gym and a bonus bunk room with sleeping quarters for up to eight make this home as functional as it is elegant. Outdoors, enjoy an expansive patio perfect for entertaining, a swimming pool, and a tennis/pickle ball/sport court-all surrounded by meticulously manicured landscaping that recalls a bygone era of quiet sophistication. A true Connecticut gem,

276 Greenley Rd, New Canaan
250 Carter St, New Canaan
$5,600,000
6 Beds ⋅ 9 Baths ⋅ 24116737 MLS
Convenience & sophisticated style is what you get with this ultra-chic 6 bedroom, 8.5 bathroom masterpiece perfectly sited on a picturesque 2 flat acres with 20x40 pool and private gate entry. Built with the best finishes In mind, you'll enjoy 10ft ceilings, flexible open floor plan, private office with French doors, formal rooms that flow seamlessly from one to another, and the ultimate dream kitchen featuring a gorgeous island with 2" countertop/ waterfall edge, chefs appliances, two dishwashers, custom walk-in pantry, wet bar, dramatic windowed breakfast area that opens to the family room overlooking the fabulous terrace and pool with spa. Exquisite millwork, wide plank floors, custom staircases, and cubie built-ins shows meticulous attention to detail. Absolutely spectacular primary bedroom with fireplace, vaulted ceilings, huge dual closets and spa inspired bathroom that will take your breath away featuring a 8ft x 4ft curbless walk-in shower, soaking tub, 10ft floating vanity, and heated floors. (All bedrooms have en-suite bathrooms). Gorgeous mudroom with 2nd laundry and elevator that travels from bedroom level to the finished basement. This home has all the features for today's discerning buyer including Smart Home technology, Crestron lighting system, state of the art mechanical room, full house generator and setting the new standard in energy efficiency. Just Minutes to New Canaan's shopping and dining, Train Station, schools, fields, and Merritt Pkwy.

250 Carter St, New Canaan
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
15 Lexington Ave, Greenwich
$5,500,000
4 Beds ⋅ 6 Baths ⋅ 24147078 MLS
Town and Country. Enjoy the best of both worlds in a sun-drenched custom built single family home one block from Greenwich Avenue and all of its shops, restaurants and amenities. Thoughtfully designed with generously scaled rooms throughout, this 4 bed, 5.1 bath 4,000+ sf home features an open floor plan on the main living level, exposures in every direction, a variety of spaces to gather, and elevator to all floors. The kitchen includes top of the line appliances, a butler's pantry, and eat-in breakfast area. Upstairs, the peaceful primary suite features a separate sitting area, large bathroom, walk-in closet, and french doors to a Juliet balcony. Additional outdoor spaces include a rear yard with stone terrace and fireplace, covered front porch, and third floor rooftop deck with outdoor kitchen and fireplace. Attached 2-car garage. Low maintenance, easy, and convenient to literally everything. In-town living and utmost comfort.

15 Lexington Ave, Greenwich
354 South Ave, New Canaan
$5,500,000
5 Beds ⋅ 8 Baths ⋅ 24108366 MLS
Experience extraordinary living in this sophisticated, estate-style majestic brick townhouse with slate roof - a truly unique custom-built home showcasing timeless elegance & impeccable architectural detail across 4 expansive levels. A gracious gated entrance opens to a charming cobblestone courtyard, setting the stage for an unmatched living experience. Inside, you'll find beautifully appointed formal living and dining rooms, both featuring elegant fireplaces & rich millwork. The heart of the home is the open-concept chef's kitchen, with a spacious breakfast area & inviting family room with coffered ceiling & fireplace. Walk out to the professionally landscaped brick patio, where you'll enjoy a built-in BBQ, outdoor fireplace, & covered seating areas-perfect for year-round entertaining. The luxurious primary suite is a private retreat, offering a cozy sitting area, fireplace, dual dressing rooms, & 2 spa-inspired ensuite bathrooms. 4 additional bedrooms-each with their own ensuite bath & walk-in closet-ensure ultimate comfort & privacy for family & guests. The home also features 3 dedicated home offices, ideal for today's flexible lifestyle, & an elevator. The impressive lower level is designed for entertaining & relaxation, featuring a fireplace, coffered ceiling, bar, wine cellar, billiards, & well-appointed exercise room. Professionally landscaped with mature trees & perennial gardens, offers exceptional privacy & natural beauty. An architectural masterpiece.

354 South Ave, New Canaan
Greenwich
$5,500,000
6 Beds ⋅ 10 Baths ⋅ 24077550 MLS
Grand Greenwich Estate | Luxurious Living on 4.3 Acres Nestled at the end of a quiet cul-de-sac, 27 Stiles Lane is a magnificent brick manor set on 4.3 private acres of lush, manicured grounds. Offering 7,438 square feet of refined living space, this exceptional estate is designed for those who appreciate elegance, comfort, and unparalleled amenities. Inside, the grandeur unfolds with six ensuite bedrooms, ensuring ultimate privacy and convenience. The heart of the home features two fireplaces, creating warm and inviting spaces for relaxation. A gorgeous library with custom millwork is a sanctuary for book lovers or an ideal work-from-home retreat. Step outside to discover your resort-style backyard, where an oversized pool, tennis court, and sprawling stone patio set the stage for effortless entertaining. Gather around the fire pit under the stars or enjoy peaceful moments in this secluded oasis. A bonus room offers endless possibilities-fitness studio, media lounge, or playroom-while a three-car garage provides ample storage. This is more than a home-it's a private Greenwich retreat where every detail is designed for luxury living.

Greenwich
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
11 Tierney Ln, Westport
$5,499,000
6 Beds ⋅ 9 Baths ⋅ 24086785 MLS
Combining classic design with modern detailing, this masterfully crafted home by an established local builder of premier residences is sure to delight even the most discerning buyer. Impressively positioned at the end of a private lane in the heart of the Greens Farms, this one of 2 exceptional custom homes. The main level exudes luxury, showcasing the expert millwork that flows throughout the beautifully proportioned Living Room, Dining Room and Study into the stunning Chef-inspired Kitchen that adjoins the sunny Family Room with fireplace and access to a large deck. The second level includes an elegant Primary Suite with built-in custom cabinetry, a fireplace and a spa-like bathroom, 4 additional ensuite Bedrooms, a Family Room/Lounge and a Sitting Room or Office. The third level has a Flex Space/Playroom. The handsomely appointed walk-out Garden Level features a 6th Bedroom, Full Bath, a Family Room, with a stylish well-equipped Bar, a Gym with mirrored walls and rubber floor, a tiered level Home Theater with pre-installed wiring, a Sauna and a room for a Wine Cellar. Graciously situated on 2 sunny picturesque acres with a Salt Water Swimming Pool, surrounded by a large Granite patio and a site for a Pool House. This exceptional home has just been completed and is available for immediate occupancy.

11 Tierney 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
19 Joann Cir, Westport
$5,396,000
6 Beds ⋅ 9 Baths ⋅ 170618303 MLS
Elegant new construction home by Mattera Construction sits in the middle of one of the most centrally located neighborhoods in Westport. Dramatic 6 Bedroom home, features an inground Gunite Pool, while offering 6 full baths and 3 half baths on 4 finished levels. An oversized custom Kitchen with Breakfast area, Family Room, Office, Living Room , Dining Room, Mudroom and 2 half baths complete the main level. On the 2nd level the oversized Primary Suite features 2 large walk in closets and a private bath. 4 more en-suite Bedrooms and Baths plus a Laundry Room are also on the 2nd floor. The Lower Level boasts an additional Family Room, Gym and a Bedroom with Full Bath. The finished 3rd level offers an additional Playroom or Office plus a half bath. Custom details and finishes throughout!

19 Joann Cir, Westport
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
26 Pequot Ln, New Canaan
$5,250,000
6 Beds ⋅ 8 Baths ⋅ 170473214 MLS
THIS MAGNIFICENT ESTATE HAS BEEN FEATURED IN THE N.Y. TIMES MAGAZINE FOR ITS EXTRAORDINARY ENTRY AND CONSTRUCTION. BE IT THE OVERSIZED POOL, RARE CUSTOM ELEVATOR, SPORTS TENNIS COURT, MEDIA ROOM, HIS & HER SEPARATE BATHS, ALSO INCLUDED ARE SEVERAL PRACTICAL AND FUN AMENITIES THAT GRACE THIS ONE OF A KIND HOME. WITH PRIVACY ON ALL FOUR SIDES THIS HOME PRESENTS ONE OF THE BEST LOTS, SCHOOL SYSTEMS IN CT. STONE WALLS & SPECIMEN PLANTINGS ABOUND AND ONLY 1.8 MILES FROM POUND RIDGE N.Y. AND 4 MILES FROM THE TOWN OF NEW CANAAN CT. NEW CANAAN IS ONE OF THE SAFEST COMMUNITIES IN THE TRI STATE AREA, A MUST SEE IN THESE TIMES. THE REPLACEMENT COST OF THIS HOME IS ESTIMATED AT OVER 10 M, SO AT THIS ASKING PRICE IT IS CLEARLY A GREAT DEAL. IT CAN BE SOLD FURNISHED IF DESIRED. IN ADDITION A POOL TABLE, EXERCISE EQUIPMENT, DESK, A MAGNIFICENT CHANDELIER ARE INCLUDED. CUSTOM BUILT BY THE ONLY OWNER IT IS A MUST SEE. YOU WILL NOT BE DISAPPOINTED. ITS BEAUTIFUL MOLDINGS, VERANDA AND CLASSIC DESIGNS ARE RARE IN TODAYS BUILDING COMMUNITY. WITH THE HIGHEST QUALITY CONSTRUCTION & APPLIANCES IT WILL SERVE THE NEW OWNERS WELL.

26 Pequot 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
7 Buttonwood Ln, Darien
$5,200,000
5 Beds ⋅ 8 Baths ⋅ 24156548 MLS
Spectacular quintessential New England home in Darien has it all! Step into a world of refined elegance with this stately 8,000+SF Colonial masterpiece. Set back on nearly two acres of manicured grounds, boasting a custom 2021 Gunite pool, outdoor kitchen, new patio, huge backyard and firepit, this treasured residence is the ultimate venue for indoor & outdoor living and entertaining. The main level features a soaring 2-story foyer that transitions into a formal living room w/fireplace & stunning formal dining room w/ butlers pantry, wet bar, wine fridge & food pantry. Step into the chef's kitchen w/ 16ft marble island, Miele range, dual Sub-zeros & sun-drenched breakfast area. The kitchen flows into a massive family room w/ stone fireplace & adjoining sunroom w/ 25ft stone fireplace w/French doors to backyard & pool. There's a large, office w/ custom paneling & coffered ceiling, a mudroom w/built-ins, plus a full bath, a powder room and back staircase to upper level rooms. The 2nd floor primary suite is a private sanctuary, defined by 11-foot barrel vaulted ceilings, a fireplace, 2 walk-in closets and a spa-inspired marble bath w/double sink, soaking tub & steam shower. There are 4 additional en-suite bedrooms, a laundry room & open space for study/gaming. The 3rd floor has over 2,400sqft of storage/ potential living space!

7 Buttonwood Ln, Darien
25 Dialstone Ln, Greenwich
$5,200,000
6 Beds ⋅ 8 Baths ⋅ 24131024 MLS
Experience exceptional craftsmanship in this new construction 6-bedroom, 6.2-bath home on a desirable Riverside cul-de-sac. Spanning over 6,500 sq. ft. across four levels, this thoughtfully designed residence blends luxury, comfort, and convenience. The main level features 10-foot ceilings, white oak floors, and a dramatic double-height family room with a gas fireplace. The show-stopping eat-in kitchen anchors the home, complemented by a formal dining room with wet bar, living room with fireplace, and private office. Upstairs, the primary suite impresses with vaulted ceilings, dual walk-in closets, a fireplace and a spa-like bath. Four additional bedrooms each with a walk-in closet-and three bathrooms complete the upper floors. The finished lower level offers a family room with fireplace, wet bar, gym, and en suite bedroom. Outside, enjoy a private oasis with a fire pit, motorized pergola, and room for a pool. Only minutes from schools, train, parks, and Old Greenwich village.

25 Dialstone Ln, Greenwich
36 Maple Ave S, Westport
$5,199,000
6 Beds ⋅ 7 Baths ⋅ 24165045 MLS
Beautiful Georgian Colonial style home in desired Greens Farms neighborhood design by renowned architect Judith Larson. A fabulous Redcoat design team make this home a must, perfect for todays's lifestyle with a classic feel. This 6 bedroom residence is set on a flat, level.70 acre property embodying a perfect synergy of architectural excellence and an enviable location. Crafted for modern living with a Westport nostalgic feel. This 7,000+ square-foot home showcases unparalleled design and meticulous construction across two main levels that optimize light and space. Redcoat homes construction is several grades above spec builders, attention to detail , light, and space that work for today's living are imperative in his homes. The main level features a designer kitchen, formal dining room, family room, office, and living room. An additional laundry and changing room are on the first floor. Enhanced by Redcoat's signature oversized windows, doors, and 10-foot ceilings. The second level boasts 4 bedrooms, including a luxurious primary suite, along with the main laundry area. The third floor includes an additional family space and an office. The lower level includes a sixth bedroom, gym, and playroom. Additional amenities comprise: a three-car garage, an approved pool site.

36 Maple Ave S, Westport
6 Carpenters Brook Rd, Greenwich
$5,075,000
4 Beds ⋅ 4 Baths ⋅ 24163258 MLS
Set behind gates and approached by a striking cherry blossom-lined drive, this fully reimagined storybook countryside estate represents a rare convergence of architectural character and modern, custom-built luxury. Rebuilt to the studs in 2022, the residence showcases uncompromising construction quality, bespoke finishes, and a level of design typically reserved for newly constructed estates without sacrificing the charm and scale of a classic French Normandy. Spanning 4.24 acres, the grounds are nothing short of extraordinary formal gardens, stone walls, a natural brook, and mature plantings create a private, estate-like setting with complete seclusion. The interiors are anchored by a statement gourmet kitchen expansive, refined, and outfitted with top-tier appliances and custom detailing seamlessly flowing into beautifully scaled living and entertaining spaces. The property offers 4 bedrooms and 3.5 baths, along with both attached and detached two-car garages, offering versatility for collectors or creative use. A separate cottage enhances the estate's livability, ideal for guests, staff, or extended stays. A turnkey, design-driven estate for the buyer who demands privacy, presence, and precision in every detail.

6 Carpenters Brook Rd, Greenwich
5 W Branch Rd, Westport
$5,050,000
6 Beds ⋅ 9 Baths ⋅ 24178890 MLS
Carefully crafted Connecticut modern farmhouse by award-winning Heine Development, this exceptional 6-bedroom residence blends timeless architecture with refined contemporary living amongst 4 finished levels on 2 private, level acres in one of Westport's most convenient luxury locations. Designed with perfection in symmetry, detail, and craftsmanship, the home pairs classic farmhouse inspiration with sophisticated modern finishes, including wide-plank white oak floors, curated lighting, and elegant interiors by renowned House of Clement. The stunning chef's kitchen features Sub-Zero and Wolf appliances, seamlessly connecting to beautifully scaled living and entertaining spaces filled with natural light with Southern exposure and beautiful sunsets. Outdoors, enjoy a resort-style ozone maintained 20'x 50'pool with automatic safety cover, sun shelf, and expansive flat lawns enhanced by organic vegetable beds. The extraordinary lower level offers the ultimate lifestyle experience with a gym, sauna, full bath and a custom treehouse, playroom, and second laundry room, creating flexible spaces for wellness, recreation, and everyday convenience. Additional highlights include natural gas heat, a generator, and exceptional indoor-outdoor flow designed for effortless living and entertaining. A rare offering that combines privacy, luxury, and modern farmhouse elegance just moments from town, train, beaches, and all that Westport has to offer.

5 W Branch Rd, Westport
125 Old Rd, Westport
$5,036,000
6 Beds ⋅ 9 Baths ⋅ 24148223 MLS
Experience the elevated ease of modern luxury in this brand new SIGNATURE Home by SIR Development, Westport's most respected ground-up RE developer with 30+ years & 300+ completed homes. Set on a scenic park-like acre w/ gunite pool & circular drive, conveniently located within walking distance of Long Lots School & shops, just 1.7 mi to train. Experience the grandeur of the soaring two story foyer, the generous artisan millwork, decorative accents & remarkable scale of 10 ceilings w/ character grade oak floors on main level. LR has unique modern built-ins & DR has a wall of glass. Grand in scale, the Great Room has a distinctive modern fpl, reclaimed antique wood beams that give organic authenticity, walls of glass & an open flow to breakfast rm into the kitchen, which was designed w/upgrades: full-size Sub Zero refrigerator & freezer, fully integrated Wolf cooktop & wall ovens, stunning waterfall island, cabinetry & pantry. Tucked away, arts & crafts workshop or office has a private entry & built-ins. The mudroom leads to 3-car garage & pool. Grand primary suite w/ incredible closets & lux bath. All en-suite BRs on 2nd flr. Finished 3rd floor w/ 2nd office, bonus rm & bath. The walk-out LL has 6th BR, full bath, gym, media, playroom. Quality construction, cohesive design & functional layouts are hallmarks of SIR SIGNATURE Homes.

125 Old Rd, Westport
24 Compo Pkwy, Westport
$5,035,000
5 Beds ⋅ 6 Baths ⋅ 24146922 MLS
Rare opportunity to live on one of Westport's most desirable Compo Beach cul-de-sacs. Beautifully restored and reimagined for today's lifestyle, this character filled 1925 Colonial features beamed ceilings, exposed stone, four fireplaces and more. Grand entertaining spaces include an expansive Dining Rm/Living Rm with 10' ceilings and two FPLS, a bright modern Kitchen and Family Rm w/FPL, a relaxing Sunroom and an inspired glass-enclosed Office for working from home. Five Bedrooms on the second floor include Primary Suite and second BR, each with vaulted ceiling, three add'l spacious BRs, a laundry rm plus a Second Office/Study Rm. Fin LL has Playroom/Gym. Set on over half an acre with old stone walls, mature trees and gardens, the home's outdoor amenities include an 18'x 38' Gunite Pool with Spa and Safety Cover, an award-winning Pool House with bath, changing rm and outdoor shower, patio w/pergola and built-in BBQ, a wood-burning fire pit and a fenced vegetable/cutting garden. Walking distance on sidewalks to the beach, train and restaurants at Saugatuck, Compo Pkwy is a quiet cul-de-sac just across the street from Westport's Longshore Club, with 18-hole golf course, tennis, pickle, sailing school and ice skating rink in the Winter months. At the beach, yet with privacy and property, this home offers the best of both worlds -beach and country living- in a premium Westport location.

24 Compo Pkwy, Westport
473 Hollow Tree Ridge Rd, Darien
$5,000,000
5 Beds ⋅ 8 Baths ⋅ 24157029 MLS
Welcome to 473 Hollow Tree Ridge Road in Darien - a custom built, stone and shingle Colonial set on 1.3 professionally landscaped acres offering exceptional indoor and outdoor living. This 5-bedroom smart home blends timeless architecture with extensive upgrades and modern technology throughout. The resort-style backyard features a pool with spa, pool house with nano doors, outdoor shower, custom outdoor bar, Lynx grill, fireplace, and covered patio. A slate roof, horseshoe driveway, whole-house 25kW Generac generator, and oversized 3-car garage with heated epoxy floors, built-ins, and wainscoting provide both convenience and peace of mind. The fully remodeled kitchen includes a Wolf range, additional wall oven, Sub-Zero double refrigerator/freezer, double islands with prep sink and second dishwasher, Negresco granite and quartz countertops, island seating, and a wet bar with glass dishwasher and ice maker. A paneled office, homework stations, guest/au pair suite with private access, oversized mudroom, laundry, and two powder rooms complete the main level. Upstairs, the primary suite features a renovated spa bath with heated floors, freestanding tub, oversized shower with rain head, and custom walk-in closets. Two additional ensuite bedrooms, a fourth bedroom with hall bath, game room with full wet bar, media room, and office/workstations provide flexible living.

473 Hollow Tree Ridge Rd, Darien
89 Pastures Ln, New Canaan
$5,000,000
5 Beds ⋅ 7 Baths ⋅ 24135730 MLS
Your Private Five-Star Resort in New Canaan: Experience the pinnacle of luxury at this 2-acre custom estate, where "vacationing at home" is your daily reality. Tucked behind commanding stone columns near the vibrant town center, this park-like sanctuary is framed by gorgeous stone walls and lush, professional landscaping and sited on a quiet cul-de-sac. The sun filled open-concept interior boasts 9'+ and vaulted ceilings, extensive millwork and gleaming hardwood floors, anchored by four fireplaces that radiate warmth and sophistication. At the heart of the home lies a breathtaking chef's kitchen featuring a legendary island with enough room for a large gathering and a dreamy walk-in pantry. The formal living room with gas fireplace and formal dining room with butler's pantry offer an easy flow for entertaining. With 5 bedrooms, 6.5 baths, a stately library and two additional offices, there is unparalleled space for both high-stakes productivity and total relaxation. The lifestyle continues outdoors with a sparkling pool and a private sports/tennis/pickleball court designed for endless summer afternoons. Whether hosting a grand gala or retreating to your private oasis, this property offers a seamless blend of modern elegance with New England charm.

89 Pastures Ln, New Canaan
10 Surf Rd, Westport
$5,000,000
4 Beds ⋅ 4 Baths ⋅ 24138082 MLS
Custom-built waterfront retreat on Bermuda Lagoon is an extraordinary find. Lovingly maintained and never flooded, 100 feet of private beach, a deepwater dock, and breathtaking views of Long Island Sound and Bermuda Lagoon. Designed for year-round enjoyment, the home's soaring ceilings and expansive windows perfectly frame the stunning water vistas. Imagine savoring sunsets from the wraparound deck or cozying up by the fire as snow gently falls. Two dedicated offices, one on the main floor with a full bath, and a second in the primary suite with a private deck and panoramic Sound views provide ideal work-from-home solutions. The gourmet kitchen, complete with an industrial stove, is a chef's dream. The primary suite, a true haven, features a private deck, generous walk-in closets, and a spa-like bath. Three additional bedrooms, two with charming lofts, offer ample space for family and guests. The lower level, an entertainer's paradise with a fireplace warmed family room and a wellness oasis, recently upgraded 42-foot indoor pool, sauna, steam room, and gym. This rare waterfront sanctuary, complete with a full-house generator, offers a unique blend of natural beauty, luxurious living, and enduring tranquility.

10 Surf Rd, Westport
11 Beachside Cmn, Westport
$5,000,000
5 Beds ⋅ 8 Baths ⋅ 24113390 MLS
A true Westport icon, 11 Beachside Common is one of the most architecturally distinctive homes on the Connecticut coast-known to anyone who's ever strolled Burying Hill Beach. Set on 2.6 waterfront acres, the property offers sweeping southern views over Sherwood Island and Long Island Sound, with sunsets that rival the Low Country and birdlife that fills the surrounding marsh with movement and sound. With water access for kayaking and paddle boarding, it's a nature lover's paradise wrapped in high design.Originally built in 1971, the home underwent a $13M transformation under acclaimed architect James Biber of Pentagram. The goal: not to create rooms, but to dissolve them. Nearly 9,000 sq ft of open, gallery-like living space is unified by a 150-ft handmade tile path that runs the length of the main level. A soaring central room with exposed aluminum column is flanked by playful architectural elements -domes, portholes, skylight tubes, and a floating staircase.A 3-story "tower," designed as the intellectual center of the home, offers 360-degree panoramic views and quiet workspace. This is a home where design, art, and imagination intersect-and where brilliant minds have found inspiration. From Academy Award winners to world-renowned scientists and adventurers, this home has drawn extraordinary lives. If genius gravitates toward whimsy, perhaps it's because whimsy makes room for wonder-and for those bold enough to see differently.

11 Beachside Cmn, Westport
16 Annjim Dr, Greenwich
$4,950,000
5 Beds ⋅ 6 Baths ⋅ 24191535 MLS
An exceptional opportunity to own a thoughtfully crafted 2015 Colonial in one of Greenwich's most desirable in-town neighborhoods. Set on level grounds at the end of a quiet cul-de-sac, this home offers four finished levels of natural light, high ceilings and refined finishes throughout. The heart of the home is an expansive kitchen with a large center island that flows effortlessly into the family room and opens through French doors to a private terrace and backyard. Five en-suite bedrooms, including a flexible lower-level guest suite, provide comfort and privacy for family and visitors alike. Spaces for work, fitness and recreation, with premium features including a whole-house generator, HEPA air filtration and water filtration systems make this home as functional as it is beautiful.

16 Annjim Dr, Greenwich
114 Ferris Hill Rd, New Canaan
$4,925,000
6 Beds ⋅ 9 Baths ⋅ 24132650 MLS
The beloved 1925 Elmstone Estate situated on over 4 acres in the heart of Ferris Hill has been lovingly restored w/ high-end finishes that blend original charm and modern-day luxury. A gated drive leads to a spectacular iconic stone home anchored by a breathtaking historic elm tree. A welcoming Dutch door leads to the expansive foyer. A second staircase leads to the masterfully designed custom kitchen w/ a generous butler's pantry and scullery. The family room with fireplace offers views of the large stone terrace and expansive gardens. The first level also includes four-season sunroom, elegant dining and living rooms each with a fireplace. A paneled library with picturesque privacy, built-ins and wet bar is the ultimate home office. Storage abounds throughout the home, including a large primary suite with an oversized marble bath, walk-in closet, fireplace, and Juliet balcony. A wide, gracious hallway, leads to four more bedrooms and one with its own oversized private balcony. Basement level is complete with a home gym, wine cellar/tasting room, sauna, fp, and large utility space. This scenic property includes a breathtaking two-story multi-use modern barn and professional garages with eight-car parking, entertaining, and living spaces. Beautifully landscaped pool w/ pool house has a full bath and outdoor kitchen. The tennis court is a private gem bordered by stone walkway & pergola. Your own private club and oasis, this is a generational country estate not to be missed!

114 Ferris Hill Rd, New Canaan
42 Hillcrest Rd, New Canaan
$4,855,000
5 Beds ⋅ 8 Baths ⋅ 24134781 MLS
A masterpiece of modern luxury, this 8,400 sq ft estate by Arena Development has been meticulously crafted to elevate everyday living. Thoughtfully designed and majestically sited with a dynamic, light-filled layout, the home unfolds across four exquisitely finished levels, anchored by a spectacular chef's kitchen and expansive family room that form the true heart of the residence. Five beautifully appointed en suite bedrooms offer refined comfort, while the home's position on the coveted West Side places you just minutes from the transportation and village. Every detail speaks to sophistication and craftsmanship-soaring ceilings, four elegant fireplaces, graceful transitions between living spaces, and a stunning walkout lower level designed for recreation and relaxation. Outdoors, a brand-new pool and spa transform the property into a private resort, complemented by a three-car garage and serene, manicured grounds. Built to the highest standards of performance, the residence combines luxury with efficiency. Energy Star construction, a 7-zone dual-fuel heating system, and a suite of advanced smart-home technologies ensure effortless comfort in every season. High-performance insulation, intuitive smart thermostats, and integrated whole-home automation complete this exceptional offering. Refined, innovative, and beautifully executed-this is modern living at its most luxurious

42 Hillcrest Rd, New Canaan

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