luxury houses for sale Pound Ridge, United States

119 Proprietors Crossing is a breathtaking estate by architect James E. Gearity. Set on four acres, this fully restored six-bedroom home blends timeless elegance with modern function.nnA private drive and grand fountain lead you in to a soaring foyer with a sweeping staircase beneath a dramatic Baccarat chandelier. The parlor, with one of seven fireplaces, flows to a serene terrace. The Blue Room offers a refined retreat, while the study, with a coffered ceiling and secret staircase, connects to the primary suite.nnThe formal dining room glows under another Baccarat chandelier. Adjacent is the chefs kitchen, now complemented by the extended family kitchen in the Great Room featuring an enormous leathered quartz island. This room, with a 35.5-ft vaulted ceiling, boasts integrated high-end speakers as part of a whole-home audio system.nnThe primary suite showcases an 800 sq. ft. dressing room and a gorgeous two level bathroom with freestanding tub. The lower level of the home offers a media room, gym and wine grotto. The outdoor space includes a dining pavilion, outdoor kitchen, and a brand-new pool with spa.nnBuilt for luxury and efficiency, the home has commercial-grade systems, SIP walls, a Welsh slate roof, radiant heat, and 14 temperature zones for your comfort. Additional features include a four car garage and an elevator accessing all levels of the home. This newly restored gem incorporates enhanced functionality for todays buyers, built to last for generations.

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.

Updated to perfection, this classic 5-bedroom Connecticut Colonial offers over 5,500 square feet of curated living space, harmoniously positioned on a private, sought-after cul-de-sac within an enclave of 4+ acre estates. The residence unfolds with a sun-drenched brand new chef's kitchen featuring custom cabinetry, premium quartz countertops, and high-end appliances, all flowing through floor-to-ceiling glass sliders to an expansive deck and a grand family room anchored by a stately fireplace. A sophisticated main level offers a formal dining room, elegant living room, and a bespoke private office with picturesque views of the park-like grounds. Upstairs, the primary suite serves as a sanctuary with a dedicated sitting room and new spa-inspired bath, while a separate private-entry in-law suite provides a secluded fifth bedroom and sitting area for ultimate versatility. The newly finished 1,700-square-foot walk-out lower level elevates entertaining with a massive media/playroom, an additional family room, and potential for a custom wine cellar-all just minutes from the vibrant New Canaan town center, top-tier schools, and the Metro-North train.

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.

Enter a world of opulent privacy on nearly twenty-five acres of pristine countryside, boasting five acres of serene lakes, an 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.

Private 6.2-Acre Lukes Wood Oasis: Bespoke Luxury - Car Lovers Dream! Tucked away on 6.2 lush, private acres in prestigious New Canaan, this custom-built Lukes Wood estate underwent a spectacular full renovation by Award-winning RR Builders in 2014, expanding the sophisticated main residence to over 8,500 square feet of turnkey luxury. The expansive floor plan boasts six generously appointed bedrooms-each featuring its own en-suite bath and walk-in closet-alongside elegant formal living and dining rooms, a private library, a wine cellar, a butler's pantry, and a finished walk-out lower level with a bath. At the heart of the home, a massive chef's kitchen with a double island and professional-grade appliances flows into a sun-drenched breakfast room and a magnificent great room, which showcases a floor-to-ceiling stone fireplace, cathedral ceilings, and rustic beams. French doors transition seamlessly to an outdoor sanctuary featuring a 45'x22' gunite pool, an expansive terrace, a pavilion with a firepit, private walking trails, and an 8-car garage configuration including a separate barn-delivering an unparalleled, ultra-private retreat close to New Canaan's top-tier schools and vibrant community.

Hillandale is a once-in-a-lifetime offering—an extraordinary opportunity to own one of the most iconic and expansive estates in the region. Encompassing approximately 268.2 sylvan acres, this landmark property gracefully spans the New York/Connecticut border, offering stunning views over formal gardens, a private lake, and rolling woodlands. Total privacy, historic pedigree, and timeless elegance define every aspect of this extraordinary estate. At its heart stands a majestic European-style stone manor, originally constructed in 1900 and once owned by the Sulzberger family, publishers of The New York Times. The residence has since been expanded and masterfully restored by the current owners, now offering more than 15,000 square feet of refined living space. Exquisite materials—imported antique marble, limestone, onyx, mosaic tile, and stained glass—adorn the interiors, where craftsmanship of a bygone era meets the comforts of modern luxury. The stately manor features eight bedrooms and ten full and four half bathrooms, anchored by grand formal living and dining rooms with intricately carved wood paneling and elegant fireplaces. A gracious library, conservatory, cloakroom, and breakfast room add to the home’s refined flow and character. At the center of the home’s leisure offerings is a spectacular indoor Olympic-sized pool, clad in Italian mosaics, complemented by a second outdoor pool and adjacent pool house—ideal for warm-weather entertaining. The grounds are as captivating as the interiors, with private lakes, formal gardens, wooded trails, and a whimsical hedge maze designed for children. More than five miles of private roads wind through the estate, offering serene views and access to a variety of outdoor amenities, including a tennis court, greenhouse, two horse barns, and four additional guest or staff residences. With its clay-tiled roof, enduring stone construction, and unparalleled sense of scale and privacy, Hillandale is more than an estate—it is a generational legacy. Whether envisioned as a private retreat, equestrian compound, or world-class residence for entertaining on a grand scale, Hillandale stands as a rare jewel in the heart of the tri-state countryside.

'In a Garden'bordered by the East Branch of the Mianus River is situated in North Stamford near the Long Ridge Historic District. Updated & beautifully designed, it offers an ideal downsize or weekend retreat with sweeping gardens, mature plantings, & river frontage. A luxurious first-floor primary suite has 2 baths, and opens to a terrace overlooking the water. Upstairs are guest rooms and an office option. A bright kitchen, formal living & dining rooms, & a reading room all overlook the river and waterfall. A detached studio, two-car garage, whole-house generator, fencing, and gated Belgian-block drive complete this two-acre hideaway. Please see full narrative on ''In A Garden'' in documents

A rare offering where extraordinary craftsmanship, uncompromising luxury, and complete privacy converge to create a residence without equal. Hidden behind a gated entrance and framed by magnificent stone walls in prestigious Bedford, this exceptional estate makes an unforgettable first impression long before you arrive at the front door. Step inside and discover a world designed to elevate everyday living-where soaring ceilings, dramatic open spaces, and walls of glass create a breathtaking interplay of natural light and architectural beauty. Every inch of this remarkable home has been masterfully crafted with an unwavering commitment to quality, seamlessly blending timeless sophistication with modern comfort. The main level is designed for both grand-scale entertaining and effortless daily living, featuring expansive gathering spaces, a beautifully renovated chef's kitchen, and a private guest or in-law suite offering comfort and flexibility for extended stays. Outside, a resort-caliber setting awaits. A spectacular covered terrace is anchored by a grand outdoor fireplace on one end and a built-in grilling station on the other, with generous spaces in between for elegant entertaining or quiet evenings under the stars. Beyond, an extraordinary custom stone infinity-edge pool, separate stone spa, and sweeping terraces create a private sanctuary that feels more like a five-star resort than a private residence. Return indoors to enjoy the private steam sauna and Finnish spa on the main level-bringing a true wellness experience into your daily life. The second floor is dedicated to luxurious private living, highlighted by an exquisite primary suite designed as a personal sanctuary, along with three additional en-suite bedrooms that offer exceptional comfort and privacy for guests. The lower level redefines home entertainment with an experience rivaling premier private clubs-featuring a custom-designed full bar, a state-of-the-art home theater, fitness studio, and expansive recreation spaces ideal for billiards, celebrations, or unforgettable gatherings. For the automobile enthusiast, the heated garage comfortably accommodates six vehicles. Perfectly positioned in Bedford, New York-renowned for its historic charm, estate properties, and timeless appeal-this extraordinary residence offers the ultimate escape from the demands of everyday life while remaining close to exceptional dining, boutique shopping, and equestrian pursuits. This is more than a home-it is a destination, a retreat, and a once-in-a-lifetime opportunity for buyers seeking nothing less than perfection.

Welcome to your own private sanctuary—a meticulously maintained and thoughtfully updated home. Featuring a 1,620-square-foot retreat where nature meets elegance at every turn. Built in 1946 and lovingly cared for, this exceptional South Salem property offers the rare combination of tranquil seclusion and premier location in the sought-after Katonah-Lewisboro school district. A fabulous setting awaits as you step outside to discover the professional landscaping, quiet, private deck, and mature specimen planting. The expansive deck is perfect for morning coffee, afternoon tea, or evening entertaining. A paved driveway with Belgian block edging and a detached one-car garage complete the welcoming arrival experience. Every season reveals new beauty in this thoughtfully designed landscape. Exceptional Interior Living… Enjoy the updated eat-in kitchen with granite countertops, custom cabinets, and a coffee bar. Full first-floor bathroom, first-floor den/bedroom, dining room, plus a lovely living room with sliders to the deck and a fireplace for a cozy evening inside. Featuring 3 bedrooms, 2 full baths plus a lower level. Hardwood floors throughout. Nice natural light. The Perfect Location… Enjoy the best of both worlds: a peaceful, private setting in top-rated Katonah-Lewisboro schools, minutes from restaurants, shopping, and Metro-North train service. Whether it's winter snow, spring blooms, summer entertaining, or fall foliage—this home shines in every season. This exceptional property is fully prepared for its next chapter. With every detail attended to and the home in pristine, move-in condition, all that's missing is your personal touch. Simply arrive, unpack, and start living the lifestyle you've been looking for.

Set on a beautifully scenic 2.35-acre lot on a tranquil circle near Laurel Reservoir, this exceptional property stands as the pinnacle of curb appeal, with a picturesque pond (and private island accessed by a footbridge) leading to the home's grand facade. Completely reimagined and remodeled in 1998 by distinguished architect, Carol Kurth, and renowned builder, Joseph Sisca, the home was awarded the Society of American Registered Architects' Design Award of Merit for superior achievement and professional design excellence. The gracious two-story foyer welcomes visitors into the open concept living and dining rooms. The spacious chef's kitchen, featuring an eat-in breakfast nook with panoramic windows, adjoins an inviting family room with fireplace. Privately positioned on the main level, the primary suite includes a fireplace, private deck, and large bathroom with radiant floor heating. The upper level provides four additional bedrooms; two with ensuite baths and private balconies. The expansive finished lower level adds a rec room with wet bar, gym, workshop, and wine cellar. Beautifully integrated with its natural surroundings, the property offers exceptional privacy, scenic views, and inviting indoor-outdoor living throughout the seasons. The garage is equipped with a Tesla charging station.

Clark House, a legacy property with extraordinary provenance, was re-imagined by design legends Delphine and Reed Krakoff, adding their imprimatur of spare modern elegance. Reminiscent of a French hunting lodge and built like a fortress from steel and concrete in 1937, the property was purchased as a country residence by copper heiress Huguette Clark, and remained unoccupied and untouched until a 2014 transformation. The volume of the rooms, soaring ceilings, proportion of the windows and quality of light create a sense of serenity and openness. Stately yet modern, this is a house that can be lived in with comfort and ease. Adjacent to the dining room gallery is a walled garden with a custom pavilion for entertaining. The 52 acres were transformed in collaboration with noted landscape architect Perry Guillot into a private park with a dramatic meandering approach, a great lawn, and woodland trails amongst streams and waterfalls. A 60 x 22 pool and tennis court were also added. At the discrete entrance to the property are twin cottages; a caretaker residence and a gym. Privacy and proximity to NYC and airports along with this caliber of property make this a world class offering and a rarity by any standards.

A Sprawling 2.68 Acre Haven with Majestic Rock Gardens! Discover this beautiful, private Ranch-style home nestled on 2.68 tranquil acres. This property offers a perfect blend of peaceful seclusion and versatile living spaces, all surrounded by stunning, mature landscaping. Exquisite Outdoor Sanctuary. The expansive, professionally landscaped grounds feature mature plantings, majestic rock gardens, stunning stone wall settings, a relaxing exterior patio, and a cozy fire pit area. Enjoy seamless indoor/outdoor living with a charming covered front porch and a screened porch—perfect for enjoying private views or escaping hot, buggy nights. The home offers peace of mind and has been nicely maintained with a thoughtful Interior Layout. Step inside this classic Ranch home to find a well-maintained layout showcasing sun-drenched rooms and hardwood floors throughout. The Living Room is anchored by a fireplace creating a warm ambiance. The Eat-in Kitchen features a large window with tranquil views of the backyard setting. Versatile Living. With a total of nine rooms, there is ample space for family gatherings and private retreats. The home offers 3 bedrooms plus a den, 2 full and 1 half bathrooms, including a Primary Suite with bath. The layout includes a spacious Family Room, which functions as an accessory apartment complete with French doors that open directly to the beautiful back yard. Additional space is found in the walk-out lower level with windows, offering even more flexibility. This peaceful, private setting on 2.68 acres offers something unique in every season, and is conveniently located close to local restaurants, shopping, schools, and commuter trains.

Your first impression! A long dramatic driveway welcomes you to an entrance framed by professionally designed landscaping. The peaceful and impressive setting, with an expanded driveway area, provides abundant parking for family and guests. Originally enhanced with thoughtful additions, the home now features a spacious layout, designed for modern living. A bright first-floor office provides ideal work-from-home flexibility, while the enlarged kitchen offers improved flow and functionality for everyday living. Above the garage, a stunning primary suite addition creates a private retreat. This spacious sanctuary includes a beautiful bathroom, generous sleeping area and exceptional closet space-delivering the comfort and style today's buyers seek. Throughout the home, an abundance of skylight fills the interior with natural light, creating a bright and airy atmosphere rarely found in colonial-style homes. The current owners chose to use the original living room as their dining room, but others could easily restore the layout. The finished lower level increases the home's living potential with two additional large rooms each with storage space, a full bath, laundry room, large pantry/storage area and a large cedar closet. The home reflects consistent pride of ownership. Major updates include: Exterior recently (July 2025) stripped to bare wood, sanded, and professionally painted. Updated roofing, exterior shingle and windows. Multiple interior renovations (in docs).

Perched on a scenic ridge overlooking the bucolic waters of Oriental Lodge Pond, this exceptional contemporary home is a sanctuary for those who crave a connection to the outdoors. Situated on 1.48 acres of verdant private land, the property offers a rare blend of architectural drama and serenity. A spectacular open floor plan on the main level is the signature feature of the home. Stepping inside the home you are greeted by a dramatic sky-lit, 2-story entrance with soaring vaulted ceilings. Large windows throughout the home keep the home bathed in natural light. The living room, dining room, and family room all have cozy wood-burning fireplaces. A stylish kitchen, with a smart -tech double oven, and a sunnybreakfast nook are the hub of the home. The home has 5 bedrooms including one on the main floor with an adjacent bathroom, ideal for a guest or home office. There are 4 bedrooms upstairs, highlighted by the fire-lit primary bedroom, en suite. The lower level offers a special opportunity to finish addition space with over 1,000 square feet of space, including a fireplace, eager for your finishing touches. If you enjoy kayaking or ice skating, the property has direct access to the water and even owns a little slice of the island within the pond. Whether you're hosting a boisterous gathering or enjoying a quiet morning watching the mist rise off the pond, this home offers an unparalleled North Stamford lifestyle. Welcome home.

Welcome to a truly exceptional New Canaan architectural masterpiece built in 2004, nestled on a majestic private lane occupied by only 6 estates, enveloped by serene forests and 48 acres of reservoir conservancy. This picturesque estate offers a tranquil escape and sense of openness with intricate millwork and wainscoting adorning every corner, 9 to 12-foot ceilings on every level and sun-drenched spaces throughout. Spanning over 11,000 square feet(+4000 SF LL) with 6 bedrooms, 7.2 baths on 4.7 acres with room to add a custom pool, go inside to discover a seamless blend of ultimate privacy and modern luxuries throughout 4 finished levels. Immerse yourself in the serenity just 5 minutes to downtown New Canaan and an hour to NYC, where luxury and tranquility converge in perfect harmony MICHIGAN ROAD TO SUMMERSWEET LANE

Welcome to a truly exceptional New Canaan architectural masterpiece built in 2004, nestled on a majestic private lane occupied by only 6 estates, enveloped by serene forests and 48 acres of reservoir conservancy. This picturesque estate offers a tranquil escape and sense of openness with intricate millwork and wainscoting adorning every corner, 9 to 12-foot ceilings on every level and sun-drenched spaces throughout. Spanning over 11,000 square feet, with an additional 4,000SF+ lower level, with 6 bedrooms, 7.2 baths on 4.7 acres with room to add a custom pool, step inside to discover a seamless blend of ultimate privacy and modern luxuries throughout 4 finished levels. Immerse yourself in the serenity just 5 minutes to downtown New Canaan and an hour to NYC, where luxury and tranquility converge in perfect harmony. MICHIGAN ROAD TO SUMMERSWEET LANE

Enchanting country estate located on a rare private lane. Sophistication Grace and Style are the hallmarks of the residence. Entire house has been exquisitely renovated - designer kitchen with bespoke cabinetry, deluxe appliances, stunning new Primary suite bath, newly transformed lower level Garden Room Salon. And as a bonus - a world class barn offering additional 3 car parking; entire 2nd floor entertainment/exercise room; and 2 workrooms for your Vintage or Contemporary cars. All of this sited on 4+ acres of rolling lawns, perennial gardens, pool, pergola, PERFECTION! All located in the charming New England town of New Canaan with outstanding shopping, delightful restaurant choices, beautiful parks, numerous recreational facilities, highly-rated schools, and convenient access to the Metro-North Railroad.

Lifetime opportunity to create your own private dream estate on 13 magnificent waterfront acres with gorgeous views. Property includes a variety of flat, wooded and open land with stone walls. A rare country setting on a very large property with close access to lovely New Canaan town and NYC commute. Property combines listings for 469, 531 and 533 North Wilton Road. The Assessment and Taxes are approximate for 3 combined lots.

THE SELLERS ARE ASKING FOR HIGHEST AND BEST BY 10AM ON TUESDAY 4/28. A commuter's dream! Located on a peaceful cul-de-sac street directly on the NY/South Salem border for easy access to the Katonah train, New Canaan, Stamford, etc., and it's just minutes to downtown Ridgefield! Fully updated in 2017 by Sturges Bros., this home has hardwood floors, freshly painted walls inside, a stunning white kitchen with an island. An open floor plan on the main level is great for entertaining! Step outside onto the deck and enjoy a huge yard with beautiful plantings, trees, and plenty of space for activities and more gardening. The three bedrooms are well-sized and share a spacious bathroom with tub. Downstairs, the family room has a bathroom with a shower, laundry, and offers room to work out, watch TV, play games - the possibilities are endless! The immaculate garage offers lots of extra storage and plenty of room to park your cars. Come and enjoy easy living in this fantastic home! It won't last!

Beautiful flat waterfront acreage - never developed, with magnificent reservoir views. Access to property provided by right of way from 469 North Wilton Road, access road is unpaved but roughed in and visible.