luxury houses with pool for sale Millbrook, United States

Experience sophisticated country living at this completely reimagined, modernized Cape Cod in Salt Point, NY. Nestled on a quiet, scenic road within a landscape of manicured equestrian estates and bucolic farms, this 5-acre sanctuary offers absolute privacy with no immediate neighbors—only the peaceful sound of birds chirping in the meadow. Every detail has been meticulously curated, ensuring that all the heavy lifting has been expertly completed for the next owner to simply unpack and enjoy. The home features brand-new Hardie Board siding and all-new mechanical systems, including an upgraded water system and enhanced electrical with a whole-house generator for peace of mind. Outside, your private oasis awaits: a heated saltwater pool, a relaxing hot tub, a newly built detached two-car garage, and a versatile storage shed perfect for a clubhouse. A pristine Airstream is also available for purchase, offering a unique opportunity for guest accommodation or creative space. While offering total seclusion, this retreat is incredibly well-connected. You are just 90 minutes from New York City and a short 15-minute drive to the vibrant dining and culture of Rhinebeck. With easy access to Amtrak in Rhinecliff and Poughkeepsie, and Metro-North in Wassaic, you can enjoy the best of both worlds: the tranquility of the Hudson Valley and the convenience of city accessibility.

Tucked gracefully in a private, tree-lined setting, this timeless New England-inspired residence offers the rare combination of classic architecture, exceptional craftsmanship, and effortless everyday living. Sunlight pours in through expansive windows, framing views of mature trees and a rolling lawn in every season. Every detail reflects quality—from the substantial millwork and rich materials to the thoughtful balance of formal and casual spaces. The expansive living room is both inviting and refined. At the heart of the home, the spacious kitchen is designed for both everyday living and effortless entertaining. A generous center island provides abundant workspace, complemented by ample cabinetry and a well-appointed layout. Three generously proportioned bedrooms provide peaceful retreats, each filled with natural light and tranquil views of the surrounding landscape. Outdoors, the property transforms into a private retreat. A freeform pool anchors the backyard, surrounded by natural stone terraces and layered gardens that blend seamlessly into the landscape. Whether gathering around the fire pit or spending quiet afternoons poolside, the setting feels peaceful and secluded. Beautifully maintained and thoughtfully designed, this is a home that lives as well as it looks: elegant without feeling formal, spacious without excess, and timeless in every sense.

"The Falls." Prominent Modernist Architect, Charles Gwathmey of Guggenheim Museum renovation fame, designed this masterpiece in one of the most beautiful locations, offering dramatic views, cascading waterfall, nestled on 40+ acres of beautifully landscaped grounds with serene stream and extensive stonework. The property boasts a breathtaking western view of the Litchfield Hills. Just minutes to Kent Center with Swyft, Wilson's and great shopping, this exceptional offering provides tranquil escape while remaining close to vibrant shops and renowned award winning restaurants and just 90 minutes from NYC. Step inside and discover a light filled haven with soaring ceilings and curved walls and a stunning view of the waterfall from the Living room, which opens on to a picturesque stone terrace overlooking the babbling brook. A Michael Arad-designed addition of a full bedroom suite complete with office and captivating vistas. A tennis court, gorgeously designed pool and spa, acres of meadows and rolling landscape make this the perfect estate. A natural planted roof, and Deborah Nevins-designed park, gardens, perennial paths. The Stephen Sills designed interior spaces complement the curved walls, glass-covered corridor, The primary suite is a luxurious retreat with a spacious en-suite bath featuring both a soaking tub and shower. Two additional bedrooms with built ins each have their own baths, ensuring comfortable accommodations for family or guests. A family sunroom gathering room with a beamed ceiling adds to the home's functional living space. A separate hallway leads to a private guest suite complete with a large walk-in shower, a custom-designed closet, office, sitting room and it's own private entry area bathed in natural light thanks to expansive windows showcasing the stunning views. Additionally, there are (2) 1000 gal propane tanks, 2 laundries, sound system inside and out and a heated utility barn with it's own driveway. All of this, creates one of the most gorgeous estates in Litchfield County.

Built in 1830 and set on 3.5 private acres abutting hundreds of acres of Connecticut State land, this five-bedroom Colonial is a rare find, a property where history, privacy, and natural beauty converge. Jaw-dropping sunset views set the tone from the moment you arrive. Inside, a recently updated kitchen anchors the main level, opening to a well-proportioned dining room made for long dinners with friends. The spacious living room, centered on a fireplace, is the kind of place you'll want to spend a winter evening. A main-level primary suite offers a private deck, a generous walk-in closet, and a spa-style bath, a true retreat within the home. Upstairs, four additional bedrooms share a full bath, with room for family, guests, or a dedicated workspace. The finished lower level adds a media room, home office, and laundry, keeping daily life organized and out of the way. Outside, the property comes alive. A side deck off the living room is perfect for morning coffee. The pool area, anchored by an impressive millstone table, is ready for summer entertaining. The perfect country retreat only two hours from NYC.

A Kent Landmark, Reimagined - This historic converted dairy barn offers 3,600 sq ft of flexible living space on over 14 private acres, with direct Housatonic River frontage and protected land trust borders. Hand-hewn beams, cathedral ceilings, and skylights carry the property's history throughout; while a converted silo houses a home office, art studio and gym. The sunny modern kitchen, renovated for large gatherings and generous entertaining, features an oversized island with seating, a commercial range, premium appliances, double sinks and dishwashers, and a wine cellar. The spacious dining area and lounge open to a landscaped patio overlooking a heated in-ground pool and cabana. Grounds include perennial gardens, several outdoor seating areas, and private manicured trails leading to a stream with waterfalls and the river frontage. The home includes private guest quarters and a primary suite with an elegant en suite bath featuring a radiant heated floor, sitting room, office and two walk-in closets. It features 3 additional updated bathrooms, a formal living room, pellet stoves, generous parking and EV charging. In-home garage with a workbench and space for a games table, plus old-style out-buildings complete the property.

Modern Pawling Farmhouse - This beautifully renovated Colonial home near Scenic Quaker Hill offers a perfect blend of charm and modern amenities. The spacious kitchen, complete with a center island with seating, flows seamlessly into an open dining and living area, where a cozy fireplace awaits. A separate light-filled den provides a peaceful retreat for relaxation. The main floor features a luxurious primary suite with a private bath, including both a shower and a soaking tub, and walk-in closet. Upstairs, three additional bedrooms share a full bath, making it ideal for family or guests. Outside, discover your private oasis with a heated gunite pool and spa, a basketball hoop for fun, and a delightful patio with a fire pit, perfect for evening gatherings. Conveniently located less than two hours from NYC and just minutes from Metro-North, this is the ultimate country retreat!

This contemporary cedar and stone construction home occupies one of Sherman's most spectacular settings. Set on 102.2 acres, the property provides complete privacy, panoramic mountain views, rolling open meadows, a tennis court, and a recently refinished gunite pool. The home features five bedrooms, five and a half bathrooms, and three levels of living space. Double teak entry doors open to a two-story foyer and an expansive, open-concept main level. At its center is a sunken living room with a floor-to-ceiling fieldstone fireplace and dramatic walls of windows. The adjoining dining room and kitchen both provide direct access to the wraparound deck. Also on the main level are a heated three-car garage, powder room, and spacious en-suite bedroom. Upstairs, a second primary suite offers exceptional flexibility and includes a generously sized bathroom, office area, dressing room with two walk-in closets and a sink, sauna, and sliding glass doors opening to a private deck overlooking the rolling hills. Two additional bedrooms and a Jack-and-Jill bathroom complete the upper floor. Designed for both entertaining and relaxation, the lower level includes a large family room, reading nook, gym area, laundry room, two bedrooms, and two full bathrooms. Sliding glass doors open to a pathway leading directly to the freeform pool, which was fully restored this summer to be enjoyed for years to come. The tennis and basketball court is surrounded by picturesque meadows and stone walls. A nearby two-story barn provides abundant additional storage. The 102.2-acre property comprises four building lots, with the residence situated on a 94.83-acre parcel and the remaining acreage divided among three smaller parcels. The property may also offer potential for further subdivision, subject to land-use approvals. Despite its remarkable privacy, the estate is just minutes from Metro-North rail service and less than 90 minutes from New York City.

Something very special awaits! This well kept contemporary home is privately set in a park-like 8 acre setting surrounded by woods, a meadow and low maintenance plantings. You enter through a lovely mudroom, stepping into the modern kitchen with a pantry and laundry and access to a pergola covered patio, or the living room with its vaulted ceiling and fireplace with dramatic floor-to-ceiling stonework. The house is bathed in light, having direct western exposure off the rear deck accessible from the living room and kitchen. Enter a window lined hall to access the main floor Primary Suite, a luxurious and light filled ensuite 19'x24' retreat added as an addition in 2013, complete with walk in closet, a private deck overlooking your own meadow and a dreamy primary bath. From the living room step out to the level patio and your gunite pool. Or go upstairs to the two upper levels. Level two has a full bath, a bedroom and another room currently set up as a den with its own private deck and fireplace that could easily become a bedroom. There's another bedroom ensuite with a private deck on the third level. There are two septics, one serving the original part of the house and one serving the addition. The oversized detached garage can house four cars. There is also a pond on the property near the driveway and the garage. There is a spectacular western view beyond the trees; bring your arborist to open it up! 18 minutes to the Metro North train, close to Kent, New Milford, Washington and all that Litchfield County has to offer - Great restaurants, galleries, hiking and arts.

Set along a quiet country road, this exquisitely renovated Nantucket-shingle-style home offers a serene sanctuary framed by lawns, vibrant wildflower meadows, and sweeping views of the surrounding hills. Fragrant flowers line the stone steps leading to the front door where a gracious foyer awaits. This fairy-tale-esque entrance opens into a spacious kitchen with high-end appliances and wide-plank wood floors. Beyond the kitchen peninsula is a dining room that spills into the living room with a fireplace and cathedral ceiling. The main level features a refined primary suite with large windows and lovely sitting room, while the upper level hosts a sun-drenched bedroom with vaulted ceiling. Also upstairs is a lovely flex room with bookshelves and access to a private deck - ideal for use as guest space, office, den or gym. Additional workspace/sitting area is located at the top of the stairs. Outdoor living is central to the property, highlighted by a large screened porch with French doors off the kitchen that overlooks a crescent-shaped pool, perennial and pollinator gardens, and lush surroundings. A private path meanders through the fields connecting the main house to a modern 1 BDR guest cabin, creating an ideal haven for visitors seeking quiet elegance and natural beauty. Close to many area attractions: Sharon Audubon, Sharon Playhouse, and Lime Rock Park. Easy access to area private schools: Indian Mountain, Hotchkiss, Berkshire, Kent and Millbrook School. 2 hours to NYC.

Welcome to your private rural sanctuary in scenic Warren. Tucked away on expansive acreage with its own serene pond and gorgeous grounds, this unique, single-level ranch offers the ultimate blend of privacy, natural beauty, and incredible potential. Being sold entirely as-is, this estate is ready for its next steward to bring their creative vision and make it truly shine. The primary residence features a comfortable two-bedroom layout designed for easy, single-level living, which flows effortlessly out to an in-ground pool and dedicated pool house-perfect for summer entertaining or quiet afternoons soaking in the pastoral views. Adding immense value and versatility is a fully self-contained, two-bedroom in-law apartment complete with its own private kitchen, full bathroom, and independent laundry. Embrace the very best of Litchfield County living; you are minutes from pristine lakes, hiking trails, and endless outdoor recreation, all while enjoying close proximity to the historic charm, fine dining, and boutique shopping of nearby Kent, Litchfield, and Washington Depot. Opportunities to own significant acreage with these multi-generational amenities in a prime, low-tax Warren location are rare. Bring your imagination and your updates, and claim this countryside haven as your own. All this just 2 hours from Manhattan. Bedroom count includes legal in-law unit.

Set on an extraordinary 12.81-acre parcel, this one-of-a-kind estate offers a rare blend of privacy, luxury, and architectural distinction. Fully renovated from top to bottom, the home showcases exceptional craftsmanship with high-end, custom finishes and a design unlike anything you've seen before. Step inside to the main level where soaring ceilings, exposed beams, and walls of glass fill the great room with natural light, anchored by a striking fireplace. The stunning custom kitchen is both functional and beautiful, seamlessly connecting to the dining area-perfect for everyday living or entertaining. A unique lofted office space overlooks the main living area, adding character and versatility. The main level also features a thoughtfully designed full bathroom complete with a built-in sauna for a spa-like experience. The lower level offers a private retreat with a spectacular primary suite featuring a luxurious full bath, walk-in shower, and custom closet. A second bedroom includes charming built-in bunk beds, while the mudroom/laundry room is equipped with custom built-ins and a convenient bench. Step outside and enjoy resort-style living with direct access to an in-ground pool and spa, as well as an expansive deck ideal for entertaining or relaxing while taking in breathtaking long-distance views.

Welcome to Cloud Walk Estate, a once-in-a-lifetime opportunity to own the entire summit of a private mountain in East Fishkill, NY. Encompassing nearly 120 acres across three parcels, this extraordinary estate offers panoramic views stretching close to 150 miles a setting that simply cannot be replicated.nPerfectly positioned just 90 minutes from NYC, this legacy property features five distinct structures, miles of paved driveways, and extensive ATV trails making it ideal as a family compound, luxury retreat, or creative enclave. Whether you're seeking a private oasis, an income-producing property, or a future generational estate, Cloud Walk is a canvas ready for your vision.nnMain House The Historic Stone Housen Originally built in 1929 and once owned by Dr. Rushmore, personal physician to President Franklin D. Roosevelt, the Stone House blends timeless craftsmanship with notable provenance. Featuring 4 bedrooms, 3 full baths, 2 half baths, and over 2,600 sq ft of living space, the home is wrapped in stunning stonework and filled with historic character. Inside, you'll find 3 gas fireplaces and 2 wood-burning hearths, two staircases, and a sun-drenched stone patio with some of the most breathtaking views in the Hudson Valley. A large unfinished basement and attic invite further customization and expansion.nnThe Guest House Modern Luxury Meets Naturen A newly constructed (2022) 816 sq ft one-bedroom residence complete with a sleek full kitchen, office/den, radiant floor heat, modern lighting, laundry, and a one-car garage with an EV charger. Ideal for hosting guests or offering complete privacy for creative endeavors or extended stays.nnThe Country House A Charming Renovated Escapen Located at 7 Looking Rock Lane, this fully renovated 3-bedroom, 2.5-bath home is filled with rustic charm. Soaring wood beams, a beverage center, full kitchen, laundry, and your very own private pond with a fountain make it the ultimate getaway. A separate driveway and unique Hobbit Hole feature add to its storybook appeal.nnThe Historic Barn Endless Possibilitiesn Formerly a horse barn, this structure is ready for restoration or reinvention. With strong bones, original stalls, and electricity already in place, it could become a dream event space, studio, or guest quarters. A generator is also hooked up for added peace of mind.nnOversized 3-Car Garage with Loftn A car lovers dream, this 3-bay garage includes an electric car charger, two carports, and a vaulted loft perfect for a gym, guest suite, or creative studio. A separate electric meter provides independence and flexibility.nnThe Groundsn The estate boasts nearly 1.5 miles of private, paved roads, ideal for ATVs, bikes, or scenic strolls. A massive heated 18x38 in-ground pool with a diving board awaits you, framed by serene forest and never-ending sky. With multiple build sites and subdivision potential, the property offers both luxury and legacy.nnAdditional Features:n Backup 22kW Generator (Stone House, Guest House, Barn)n Low Taxes for Acreage of This Scale (~$37,000 annually)n Two Driveways for Optimal Accessn Zoned for Maximum FlexibilitynThis is not just a property its a mountain-top kingdom with a presidential legacy. Whether you're looking to build a multi-generational compound, develop a creative or spiritual retreat, or simply own one of the Hudson Valley's most breathtaking private holdings, The Cloud Walk Compound is ready to welcome you. *Bedroom, Bathrooms, and Sqft Only reflect the Main & Guest House*