luxury houses for sale Ridgefield, United States

61 High Ridge Ave is an extraordinary estate in the heart of Ridgefield's Historic District, set atop one of the town's highest elevations with sweeping skies, radiant sunsets, and far-reaching views beyond the Hudson River. Custom built in 1997, this distinguished Stone Manor blends timeless elegance with exceptional craftsmanship. Encompassing more than 8,000 square feet across three levels, the residence showcases a stone facade, slate shingle roof, five generously sized bedrooms, and 6.1 baths. A dramatic two-story foyer opens to refined formal rooms and a handsome library, enriched by mahogany windows and doors, hardwood floors, and exquisite millwork. The expansive eat-in kitchen flows seamlessly into the inviting family room with fireplace, creating an effortless setting for everyday living and gracious entertaining. Upstairs, the serene primary suite offers two walk-in closets, a fireplace, and a private balcony, while additional ensuite bedrooms provide comfort and privacy. A finished third floor adds versatile space for wellness, work, or leisure. Beyond the main house, a separate studio cottage with full bath and fireplace offers elegant guest or flexible accommodations. Set on 2.61 landscaped acres, the estate is further enhanced by a pool, tennis court, and four garage bays, completing this rare and luxurious retreat.

Welcome to Brooke Hollow, a private and refined country estate set on over 8.7 acres along one of Pound Ridges most desirable roads. Tucked behind a gated entrance, the property unfolds into a quiet, beautifully composed landscape of rolling lawns, mature plantings, three serene ponds, and wooded walking paths that create a true sense of privacy and permanence.nnThe grounds are thoughtfully designed to enhance both beauty and livability. The three ponds are supported by aerator systems that maintain water quality, circulation, and ecological balance, allowing them to remain vibrant and visually striking year-round. A wireless deer fence system, along with perimeter fencing, helps preserve the integrity of the landscape and plantings, ensuring the setting remains peaceful, natural, and undisturbed. The result is an environment that feels both curated and effortless, offering a true sense of calm and connection to nature.nnOutdoor living is elevated with an infinity-edge saltwater pool and spa positioned to overlook the property, a full tennis court, and multiple outdoor spaces designed for both entertaining and quiet relaxation.nnThe residence, a meticulously maintained stone and shingle Country House, offers over 5,500 square feet of light-filled living space. A two-story entrance hall introduces the home, leading into a series of elegant yet comfortable interiors defined by high ceilings, custom millwork, and walls of windows that bring the outdoors in.nnAt the center of the home, a dramatic great room with a soaring ceiling and fireplace anchors the main living level, flowing seamlessly into a chefs kitchen with a large center island and adjoining breakfast area. Formal living and dining rooms provide a more classic setting, while the overall layout remains open and adaptable for modern living.nnThe home offers four bedrooms, including a first-floor primary suite designed as a true private retreat. The suite features a double-sided fireplace, a spa-like en-suite bath, and custom walk-in closets, along with direct access to the grounds, creating a seamless connection between indoor comfort and the surrounding landscape. Additional spaces include a large playroom, multiple offices, and flexible bonus rooms suited for todays lifestyle.nnA screened porch and expansive rear terrace extend the living spaces outdoors, creating a natural flow for entertaining or quiet evenings overlooking the property.nComplete with a three-car garage and surrounded by preserved land and natural beauty, this is a home that offers both substance and ease.nJust minutes to Katonah, Bedford Village, Ridgefield CT and Metro-North, yet entirely removed, this is Pound Ridge at its best: understated, private, and enduring.

Classic New England charm meets modern luxury in this beautifully updated 1921 Colonial. Perfectly situated just minutes from the quaint Georgetown boutique shops , restaurants, and Route 7. Set on nearly half an acre lot, this home offers effortless living and entertaining inside and out. The heart of the home features a renovated eat-in kitchen with timeless marble countertops, a 4 seated island, and newer stainless-steel appliances. Entertain with ease in the formal dining room, unwind by the gas fireplace in the living room, or settle into the versatile sunroom - equally suited as a home office. Upstairs, the primary suite is a true sanctuary, complete with gas fireplace, a spacious walk-in closet and renovated spa-inspired bathroom with soaking tub. Two additional bedrooms and a well-appointed hall bath round out the second floor. The third level offers a wonderfully flexible carpeted family room - ideal as a playroom, media space, or guest retreat. Step outside to a stunning country backyard oasis with a fresh 1,200 square foot bluestone patio equipped with a built in DCS grill and cozy fire pit nook. With its flat, usable property, timeless architectural character, and every major update already done, this home is a rare find in one of Redding's most convenient locations.

Located moments from Wilton Town Center, this fully reimagined 6-bedroom, 5.2-bath residence blends timeless character with modern luxury. Set on more than two pristine acres with a designated pool site and overlooking the Silvermine River, the home has been extensively renovated, showcasing exceptional craftsmanship and thoughtful design throughout. The interior features 9-foot ceilings, Brazilian cherry floors on the main level, red oak upstairs, and custom millwork. Designer finishes, modern lighting, and integrated smart-home technology complement a spacious layout ideal for entertaining and everyday living. The lower level offers two large rooms, each with walk-out access, a fireplace, a full bath, and an additional room that could serve as a bedroom, providing flexible space for nanny or in-law use, guest quarters, recreation, or a private home office. Bespoke cabinetry, premium fixtures, and top-tier appliances elevate each room. Additional highlights include commercial-grade mechanical systems, a Kohler true full-house 48 KW generator, advanced home technology and security, and a lifetime shingle roof with warranty and copper flashing. Outdoors, refreshed landscaping, new plantings, a mahogany deck and porch, and upgraded hardscaping create a private, inviting setting for gatherings or quiet enjoyment.

Nestled on a picturesque country road in the heart of Redding, this National Register of Historic Places landmark offers a rare blend of 18th-century soul and modern New England estate living. The home's historic integrity is preserved through twin stone chimneys, original wide-plank flooring, and exquisite period woodwork. Sun-filled living spaces flow seamlessly from the warm central hall to a spacious kitchen and inviting dining areas-ideal for both everyday comfort and sophisticated entertaining. The layout provides exceptional flexibility, featuring generous bedrooms and additional rooms perfectly suited for a home office, den, or guest wing. Set on two serene acres of curated gardens and mature trees, the exterior offers a peaceful retreat for outdoor gatherings or quiet mornings in nature. While seemingly worlds away in its rural tranquility, 313 Umpawaug Road in prestigious West Redding is located just minutes from top-rated schools, hiking trails, and the charming town center. Once the residence of Continental Army soldier Aaron Barlow, this 1723 Georgian gem served as a strategic hub for General Israel Putnam and a literary sanctuary where the famed Joel Barlow penned The Vision of Columbus in 1787. A rare opportunity to own a living piece of history, meticulously maintained for the modern steward.

Set across 53 gated acres in Northern Fairfield County, this exceptional estate offers a rare combination of privacy, scale, and natural beauty, just minutes from Ridgefield, approximately ten minutes from Danbury Airport, and within practical reach of New York City. Originally conceived as a country retreat, the property blends historic character with modern comfort in a setting that feels private and serene, yet fully suited to year-round living. Beyond the gates, the grounds unfold across woodland trails, a stone bridge, pond, brook, orchards, gardens, and approximately two miles of groomed paths through the estate's own natural preserve. The landscape has been carefully maintained and offers both beauty and utility, with room for recreation, agriculture, and future enhancements. The residence is rich in character and thoughtfully updated, with six fireplaces, a double-sided chef's kitchen, wine cellar, and a 1,055 SF primary suite with dual baths, dressing room, walk-in closet, private sitting room, and sunroom. Outdoor living is centered around a heated gunite pool, outdoor kitchen, pergola, and gazebo, all positioned to take in sweeping views of the surrounding landscape. A detached barn, detached garage, and expansive acreage create unusual flexibility for equestrian pursuits, agriculture, a guest house, tennis or paddle court, and other future improvements, subject to local approvals.

Discover your ultimate hideaway: a private, gated custom rebuilt 10,000 square foot Colonial nestled on over five majestic acres in Pound Ridge. While the impressive amenities are abundant, it is the serene setting that will truly capture your attention and your heart. Tucked behind a mature landscape, the property offers a retreat filled with quiet, tranquil spots. The grounds are thoughtfully designed for both relaxation and recreation, featuring a pool set off the side of the house and a secluded tennis court in the back. Inside, light floods the glass sunroom off the kitchen, and private decks extend from multiple rooms, including the luxurious primary suite. The heart of the home is the family room, boasting a dramatic, soaring ceiling height and anchored by one of three cozy wood-burning fireplaces. Welcome home!

Welcome to 158 Mead Street — offered for the first time, this custom-designed sanctuary is nestled in the heart of Waccabuc and lives like four bedrooms (4 bedroom septic). Privately sited on over four park-like acres, this elegant residence is surrounded by mature trees, creating a serene retreat just minutes from town, train, and everyday conveniences. Inside, the home seamlessly blends rustic elegance with sophisticated comfort. The dramatic living room is anchored by vaulted ceilings, authentic rustic beams, and a wood-burning fireplace, creating a warm yet refined gathering space. For today's remote lifestyle, a handsome den/home office with custom paneling and built-ins offers the perfect work-from-home setting. At the heart of the home is the expansive kitchen, uniquely warmed by a double-sided wood-burning fireplace. Entertain effortlessly in the character-filled formal dining room or unwind in the sun-drenched sunroom, which opens directly to the sprawling rear patio and picturesque grounds beyond. A rare and highly sought-after feature, the luxurious first-floor primary suite offers exceptional convenience and privacy, complete with two oversized walk-in closets and a spa-like bath. The second level provides incredible flexibility with two additional bedrooms, two full bathrooms, a dedicated second office, and an expansive playroom or media/recreation space. Experience the quiet luxury of Northern Westchester living in a home that truly has it all.

This one-of-a-kind 5 bedroom, 5 full bathroom rustic California inspired residence on one of the toniest roads in Pound Ridge sits on 6.5 private acres, complete with a pool, tennis court and treehouse. Situated in a resort like setting, the home's exquisite indoor-outdoor flow and abundant natural materials, you'll feel worlds away, but is just 3 minutes from town and an hour from NYC. Once owned by Ted Sorenson, JFK's speechwriter, the unique estate is ideal as a year-round home, weekend retreat or secluded hideaway with Belgian block and chestnut floors, stone columns (the stone of which was excavated from the site), tongue-in-groove cedar walls, soaring beamed ceilings, 22 skylights and custom windows. Custom stair railings designed by renowned rustic artist, Daniel Mack. Enjoy lavish entertaining in impressive living spaces with floor-to-ceiling fireplace and windows. The rustic dining room seats 16, the masterful kitchen with original copper bar counter, accommodates gatherings of any size. Upper-level primary suite, main-floor two-bedroom suite, home gym, media room, sauna and office with custom desk made of one solid piece of hundreds of years old Baobab tree. The lower level en suite bunk room provides ample accommodations, with private entrance. Resort-like grounds and a bucolic location make this an exceptional country estate. Custom, high level properties like this don't come up very often.

Nestled in the sought-after Dann Farm community, this home offers the perfect blend of graciousness and functionality. The dining room and living room flank the bright front hall with double-height ceilings that capture the natural light and energy of the house. The large eat-in kitchen seamlessly flows into a generously sized family room, complete with a fireplace. The main level also features a fabulous study, multiple outdoor patios, a mudroom, laundry room, powder room, all with amazing views and access to the surrounding property. The second floor features a beautiful primary suite with a sitting room, two large walk-in closets, and an en-suite bath. Rounding out the second floor are two bedrooms serviced by a hall bath and one bedroom with an en-suite bath. Outside, a brand-new 20 x 40 heated pool awaits, perfect for summer days. The unfinished basement with walk-out access is ready for your personal touch. Discover relaxed living of Dann Farm conveniently located close to Scotts Corners and New Canaan Ct!

Welcome to 3 Old Shop Road, a beautifully updated farmhouse that perfectly captures the essence of relaxed country living in a highly coveted Cross River address. Set on a picturesque, park-like parcel with sweeping lawns and mature trees, this five-bedroom, five-bath residence offers a seamless blend of historic character, modern comfort, and premium amenities. Designed for both effortless entertaining and comfortable daily living, the property features three distinct bluestone patios providing multiple vignettes for outdoor relaxation. The fully fenced backyard includes a completely separate, secure enclosure for the sparkling in-ground gunite pool, creating an ideal and private backdrop for summer enjoyment. Inside, the home retains its timeless farmhouse warmth while embracing contemporary conveniences. The inviting kitchen features custom cabinetry, a functional layout, and ample space for casual dining. The current living room is anchored by a handsome fireplace and flooded with natural light, creating an inviting atmosphere throughout the seasons. Steeped in history, the first-floor guest suite served as the farmhouse's original living room. Today, it offers a peaceful main-level retreat, boasting its own cozy fireplace and elegant French doors that open directly to a private bluestone patio and the beautifully landscaped grounds. Located in one of Westchester County's most desirable communities, 3 Old Shop Road offers the very best of country living with room to relax, entertain, and enjoy.

Private New Canaan Oasis: Bespoke Luxury can be found in this modern version of a traditional centerhall colonial in prestigious New Canaan's West School district. This custom-built Lukes Wood estate underwent a spectacular renovation by Award-winning RR Builders, updating the sophisticated main residence to over 7,000 square feet of turnkey luxury. The expansive floor plan boasts 6 generously appointed bedrooms - each featuring an ensuite bath and walk-in closet alongside elegant formal living and dining rooms, a private office, a wine cellar, a butler's pantry, and a finished walk-out lower level with a full bath. At the heart of the home, a fully appointed 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' x 22' heated gunite pool, an expansive terrace, a pavilion with a firepit, private walking trails, plus a custom-built barn that offers additional space for cars, equipment, a gym, art studio, or large office space delivering an unparalleled, ultra-private retreat close to New Canaan's top-tier schools and vibrant community.

A rare offering distinguished by architectural clarity, complete privacy, and a deeply personal design vision, set within one of Fairfield County's most sought-after locations. Jay Manuel, internationally recognized creative director and fashion icon, brings a distinctly refined point of view to his architecturally significant modern residence in Connecticut. Acquired in 2011, the home was thoughtfully completed and refined under his direction into a highly considered lifestyle environment, where design, performance, and atmosphere exist in complete alignment. Set on 2.75 acres of exceptional privacy, the sunlit European modern unfolds as a discreet compound, surrounded by mature landscape and a protected nature preserve. Designed for both intimate living and large-scale entertaining, the property features a heated saltwater pool and spa, multiple terraces, an outdoor kitchen, fire pit, and a tranquil Zen garden. The residence reflects a disciplined approach to modern living, integrating passive solar principles, advanced HVAC, and whole-property connectivity, all seamlessly embedded within its clean architectural language. Interiors are defined by soaring ceilings, walls of glass, and a Poliform kitchen with Miele appliances. A private primary suite with balcony, a dramatic glass mosaic wine cellar, and a separate 800 sf skylit studio for fitness or flexible use further articulates the home's sense of intention and versatility. Rare. Private. Architectural.

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.

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