luxury real estate for sale Millbrook, United States

Experience unparalleled privacy and luxury as you follow a driveway lined with beautiful fruit trees leading to this stunning A-Frame home. Expanded in 2009 & 2024, this residence is nestled on 6.1 acres, bordered by expansive neighboring properties, offering breathtaking views and total seclusion on the Taconic Ridge. The property features a beautifully designed swimming pond, with natural filtration. Surrounded by mature plantings, seating areas, a fire pit and a spacious blue stone patio, the pond area is perfect for relaxing or entertaining. Gardening enthusiasts will love the 12-bed raised garden, complete with a shed, potting area, water and power. The expansive grounds are filled with abundant native flora, enriched by lush edible plantings and 30 fruit trees. Inside, the home offers two primary suites: an upstairs suite featuring luxurious bath amenities, custom Andy Warhol wallpaper and amazing light. The walk-out basement suite includes a steam shower, heated floors, a stone fireplace in the adjacent living space and a wine cellar for your collection. The main floor features two additional bedrooms, a media room with a sleeping loft ideal for cozy movie nights with the 12ft projector, a chef’s kitchen equipped with high-end appliances, including a Wolf range, Miele steam oven, custom cabinetry and a quartz waterfall island. The 2024 addition adds a versatile space with in-law suite potential, two offices and future expansion options. The over-sized three-car garage is fully equipped with heating, ample storage and is ready for an electric vehicle charging station. The Trentlage Pond House is an exceptional home distinguished by its stunning surroundings, sleek interiors and complete tranquility—just 80 minutes from NYC and under 20 minutes to trains.

Country Lodge with hilltop views. Privately situated on 144 acres off a quiet country road midway between Millbrook and Rhinebeck. Brick and glass custom home built to the highest standards with attached walled garden. Approximately 13,000 sq ft of living space. Spacious rooms with high ceilings full of light and sunshine. Features include 6 ( possible 8) bedrooms. 8 full and 3 half bathrooms. The lower level includes wine cellar, gymnasium and a home theatre. There are 5 woodburning fireplaces. 2 staircases and an elevator that services all 4 levels. 20 x 40 indoor swimming pool. Attached 3 car garage. Wooded and open land with pond.

Welcome to your dream home, where contemporary design meets serene country living. Nestled on 8 picturesque acres, this exceptional 4 bedroom, 2.5 bath residence offers a seamless blend of modern elegance and tranquil seclusion. Step into a sunlit great room featuring high ceilings and seamless flow between the living, dining, and kitchen areas. Expansive glass doors open wide, effortlessly blending indoor and outdoor spaces. In addition to the main house, a separate building awaits, ready to serve as a studio, workshop, or guest suite—whichever fits your lifestyle needs.

A bucolic country road leads you to 69 Yellow City. The approach up a long, winding driveway is lined with maple and pine trees. A dark facade opens to light filled interiors, sunlight dances through the house. Spanning three floors, a careful and considered design-focused renovation was completed in 2024 with minimalism, luxury, and comfortable living in mind. The kitchen has been transformed with limestone floors, beautiful green custom cabinetry, floating shelving and marble countertops. A central island grounds the space alongside a wood burning fireplace, and you’ll find a built in loveseat in the breakfast nook. The attached sunroom makes for an excellent dining room or gathering place, or a quiet spot to read a book while taking in the peaceful views of the surrounding woods and countryside. The sunken living room features wide board wood floors and a massive fieldstone fireplace, a perfect place to settle in. Upstairs there are three bedrooms, the master is ensuite with a wood burning fireplace while two guest rooms share a beautiful bath off of the hall. All of the bathrooms have been fitted with swoon-worthy Italian fixtures and stone basins. On the lower level you’ll find polished concrete floors, an additional bedroom and bathroom, and a living room/gym and kitchenette. Sliding glass doors line the back wall and lead out to a heated, saltwater pool. Walkable to the house is Troutbeck— an incredible c1920 hotel with sprawling grounds and a fabulous bar/restaurant, locals can become members with access to tennis, the spa, and the pool. Under 10m east lies the rolling hills of Litchfield County, CT where you’ll find destination shops and restaurants in Sharon and Salisbury, and just 10m from the house is the Wassaic train station which takes you & your guests into the city in under 2h. An incredible opportunity for weekend or full time use.

West Wind Hill, a bespoke country estate on 389 acres sits on the crest of a plateau overlooking panoramic protected views. Classic stone and shingle manor house with formal courtyard sited perfectly to experience spectacular sunsets and fairytale mists combined with the upmost in privacy. Access is via a private gated road that winds through trees, past old stone walls with glimpses of open meadow, and serene pond. Spacious rooms perfect for entertaining include a great room with a soaring peaked ceiling and a 20' stone fireplace, sun-filled formal dining room with three exposures, huge Chef's kitchen with a massive stone fireplace and adjoining catering kitchen. Beautiful reclaimed chestnut floors, exquisite detailing and banks of windows and French doors. The paneled library, office and primary bedroom suite are located on the first floor in a private wing of the house. Billiard room, complete with mini-kitchen, full bath and adjoining guest bedroom. Second-floor primary guest room with soaking tub and deck with views. Two bedroom suites with en-suite bathrooms, charming bedroom and an office complete this floor. Lower level with a media room, half-bath, wine tasting room and wine cellar with adjoining prep kitchen. Laundry room, craft room and gym. Beautiful stone steps lead to a stunning pool and pool house with full kitchen and tennis court. Two building maintenance court contains a pumping system for irrigating the lawns and gardens.

Reimagined New England Farmhouse built with a genuine attention to detail in a storybook setting. The home features a handsome post-and-beam frame constructed from old growth Douglas Fir, quarter sawn white oak floors, an open floor plan, and deep covered porches. The home's main level features a handy mudroom, a newly updated eat-in kitchen with quartz countertops, lovely sunroom that opens to the screened porch, formal dining room, and a spacious living room anchored by a free standing two-story fireplace constructed from fieldstone from the property. The light-filled master bedroom suite with private bath and dressing room is located upstairs along with two additional bedrooms that share a well-appointed full bath. The walk-out lower level of the house is partially finished as rec space with potential for private a guest suite. In addition, there's a large detached barn with full HVAC and ample room above ready to be finished for a home office or studio. Set on 8.38 acres with a cleared pool site and surrounded by 3,500 contiguous acres of protected land with an extensive network of beautiful hiking trails. A true country getaway only two hours from NYC, minutes to Metro-North & the Village of Kent. Automatic Generator.

Hitting the market for the very first time, this charming 1960's brick ranch, crafted by its original owner, is ready to begin its second chapter. 126 Roosevelt Road is privately sited in a peaceful development and offers an unparalleled connection to nature, as it's backyard borders the picturesque 181-acre Eleanor Roosevelt National Historic Site, Val-Kill. Slightly over a half-acre, this lot offers a secluded oasis, with a large sloping front yard adding to the home's curb appeal and a stone patio that's ready for summer barbecues and quiet evenings under the stars. The centerpiece of the home is a massive fireplace, offering warmth and a welcoming ambiance in the heart of the living space. This solidly built ranch is a blank canvas, ready for you to bring your design dreams to life. Whether you're drawn to its mid-century charm or excited by the possibilities of modern updates, this property is a rare find in an extraordinary location.

Stunning estate property consisting of 3 parcels to total 55.83 acres with multiple building sites. Perfect for a family compound. Gently rolling hills with two plateaus offering stone walls and sweeping 330 degree forest and mountain views facing East and West. Access roads cleared and ready for you and your architect to imagine the many possibilities for this pristine property. Multiple trails for hiking, snow-shoeing, horseback riding and just enjoying nature. Just 1 mile from Macedonia Brook Connecticut State Park. Skiff Mountain Conservancy Nature Preserve, Wildwoods Nature Preserve and entry to Appalachian Trailheads nearby. 6 miles from either Wassaic or Tenmile River Metro-North Train Stations. 3 miles to Marvelwood School, 6 miles from The Kent School. Close to the charming NE towns of the Litchfield Hills. Close to NY border. Pristine and very private.

Welcome to Red Wing Pond, your private nature retreat just minutes from the Village of Rhinebeck. Originally a part of the 1870s William Dinsmore estate, this parcel has been transformed into a premium, BOH-approved, ready-to-build site of nearly 7 acres. With frontage on both sides of Indian Creek and a private spring-fed pond, this property provides a serene landscape and offers many opportunities for outdoor exploration and quiet meditation. Owned by an accomplished local builder who thoughtfully configured the home site between dramatic rock cliffs and historic stone walls, this secluded gem with spring fed pond, mature hardwood trees and proximity to amenities checks off every box. This fully engineered lot is ready for your imagination and comes with a survey and BOH approval for a 3-bedroom home, underground electric on-site and a roughed-in driveway. Builders and architects will undoubtedly be impressed with the preparation and potential of this parcel. Whether you're looking to build your dream home or searching for a wise investment, this property promises a blend of tranquility, beauty and convenience. Unlock the opportunity to craft your own retreat in Dutchess County, perfectly positioned less than 2 miles from the Hudson River, Dinsmore Golf Course, and Mills-Norrie State Park with its scenic marina. Just 90 minutes from NYC and a quick 5-minute drive to the vibrant village of Rhinebeck—filled with charming shops, restaurants, and the Amtrak station at Rhinecliff—you’ll also enjoy easy access to Metro-North in Poughkeepsie, only 15 minutes away. Embrace this chance to turn your dreams of building a country home upstate into reality with the ultimate combination of convenience and rural bliss with an unbeatable location and unrivaled natural beauty.

Welcome to 114 Sharon Valley Road, a charmingly renovated ranch set on a serene, park-like lot with mature trees and a spacious backyard that gently slopes down to a creek. This home has been thoughtfully updated in a modern farmhouse/colonial style, featuring fresh exterior paint, brand-new flooring in the master suite, a remodeled bathroom, custom blinds, and new lighting fixtures, and a whole-house water filtration system. Located just 10 minutes from Wassaic Train Station, offering a direct line to NYC, this property provides both tranquility and convenience. Inside, the home boasts stunning hardwood floors throughout, with bright, airy dining and living rooms that include a stylish dry bar perfect for entertaining. A versatile bonus room off the living room can be used as an office or den. The spacious primary suite features sliding doors leading to the back deck. Additional highlights include a cozy wood-burning fireplace, an eat-in kitchen and a charming electrified barn with a loft ideal for storage or creative use. The property also features an oversized septic system for added convenience and efficiency. Perfectly situated in the heart of the Litchfield Hills, just minutes from the village of Sharon Center and neighboring villages like Lakeville, Salisbury, Millerton, and West Cornwall. Whether you're looking for a full-time residence or a weekend getaway, this property offers the ideal balance of peaceful living and easy access to local amenities.

Ready to Build Your New Home in the Hudson Valley? How About a Captivating Mountain and Hudson River View Parcel with an Approved Septic Site? Nestled high above the Hudson River in the hamlet of Staatsburg, this 5.39-acre partially wooded lot offers a unique chance to build your dream home in a picturesque setting that boasts panoramic views of the Catskills and the Hudson River below. With BOH approval already in place, your vision for a tranquil retreat is closer to reality than ever before. Minutes to charming towns and villages, like Rhinebeck, Red Hook, Milan, and Hyde Park, renowned vineyards, Staatsburgh State Historic Site and other cultural destinations, and the vibrant pulse of the Hudson Valley. Whether you intend to build your forever home or create a weekend retreat, this property presents an excellent investment opportunity in a region known for its enduring desirability.

Capture the history and grandeur of Great Elm, the unparalleled 19th century Georgian colonial estate that was once the childhood home of author and influential political commentator, William F. Buckley Jr. Nestled in the heart of Sharon, CT, this prestigious property is a rare opportunity to acquire a residence steeped in historical significance and architectural elegance. Great Elm boasts 8,072 sqft of luxurious living space, crafted with impeccable design choices throughout. From the art deco bathrooms to the William Morris wallpaper, every room exudes sophistication and meticulous care. William Buckley Sr. purchased the original 1812 house in 1923, expanding it over time to accommodate his growing family. The main level primary bedroom suite and gracious sitting rooms, each with gorgeous detail and wood burning fireplaces, open to the dramatic three-story Atrium, a year-round haven reminiscent of New Orleans. Upstairs are 7 beautifully appointed ensuite bedrooms, one of which is used as a gym; another as an office. This property is the anchor of a community of homes joined by an Association that manages the 50 magnificent, park-like acres and amenities, including a heated, Gunite pool, pool house, tennis and paddle/pickle courts. This spectacular property in the beautiful Litchfield Hills is more than just a residence; it's a chance to own a piece of U.S. history. Close to Hotchkiss, Salisbury, Indian Mountain and Millbrook Schools. Only 2 hours to New York City.

Capture the history and grandeur of Great Elm, the unparalleled 19th century Georgian colonial estate that was once the childhood home of author and influential political commentator, William F. Buckley Jr. Nestled in the heart of Sharon, CT, this prestigious property is a rare opportunity to acquire a residence steeped in historical significance and architectural elegance. Great Elm boasts 8,072 sqft of luxurious living space, crafted with impeccable design choices throughout. From the art deco bathrooms to the William Morris wallpaper, every room exudes sophistication and meticulous care. William Buckley Sr. purchased the original 1812 house in 1923, expanding it over time to accommodate his growing family. The main level primary bedroom suite and gracious sitting rooms, each with gorgeous detail and wood burning fireplaces, open to the dramatic three-story Atrium, a year-round haven reminiscent of New Orleans. Upstairs are 7 beautifully appointed ensuite bedrooms, one of which is used as a gym; another as an office. This property is the anchor of a community of homes joined by an Association that manages the 50 magnificent, park-like acres and amenities, including a heated, Gunite pool, pool house, tennis and paddle/pickle courts. This spectacular property in the beautiful Litchfield Hills is more than just a residence; it's a chance to own a piece of U.S. history. Close to Hotchkiss, Salisbury, Indian Mountain and Millbrook Schools. Only 2 hours to New York City.

Nestled on 8 private acres off a secluded road, this 5,800 square foot stone and stucco Tudor with a distinctive turret and charming diamond-paned windows stands as a testament to timeless elegance in the picturesque town of Kent, CT. Greeted by a whimsical gargoyle at the entrance, this property is a storybook embodiment of architectural splendor. The residence boasts 10 meticulously designed rooms including 4 sumptuous bedrooms and 3 full baths and 2 half baths. The grandeur of the home is anchored by 3 majestic stone fireplaces that provide warmth and ambiance to the living room, kitchen and primary bedroom. A bibliophile's paradise awaits within the walls of a 3-story library, where custom-built mahogany shelves rise to meet a stunning stained glass skylight. Lantern sconces cast a gentle glow over the tufted banquette, inviting hours of literary indulgence. The home's screened porch is a serene retreat, while the open deck on the upper level presents a tranquil space to enjoy the natural beauty of the estate's surroundings. This property is a rare find for those who appreciate the grandeur of a bygone era, seamlessly integrated with the comforts of modern living. A true Kent treasure, this estate is waiting to become the backdrop for your family's cherished memories. Kent has a variety of great eateries, galleries, library, private schools, hiking trails, and Metro North just a few miles away.

Welcome to Sharon Green Condos - Comfort and Convenience in a Coveted Locale. Discover this 2 bedroom 2 full bath second-level unit presenting a blend of comfort, convenience, and easy living. As you step inside, you're greeted by a warm and inviting living room, complete with a cozy fireplace and sliders to a private balcony that sets the tone for relaxed evenings and intimate gatherings. Features an ensuite primary bedroom, dining room, and large pantry with laundry. Included is a one-car garage, adding to the ease of this turnkey lifestyle. Situated close to the village, residents have the convenience of nearby shopping, dining, outdoor activities, and cultural events. The condo's proximity to private schools and the Metro-North train station makes it an ideal choice for those seeking a blend of suburban tranquility and commuter accessibility. Property being sold AS IS. HOA= $305/mo Building acct =$195/mo.

Call it grand, call it groovy, this one-of-a-kind 8,000+ SF estate encompasses a meticulous 1810 Federal manor with whimsical 70s-style wing that's true entertainment nirvana. Infinite space for a compound, guests, work from home or perhaps reconceived as a luxury inn----and all with a breathtaking gentleman's farm attached. 147 acres of rolling lawns, mature trees, ponds, pastures, pool and greenhouse with multiple potential building sites. Did we mention the stunning Catskill views? Imagine kicking off your gatherings by the textured gold fireplace in the spacious sunken living room in the Modern wing before mounting a few steps to the cavernous indoor pool with lounge and then on to the conservatory deck for sunset (or sunrise) cocktails. Nearby is a free-standing staircase (with original Corning glass blocks) up to 1500 SF primary suite with spa bathroom with dual sinks and dual dressing rooms. Back on the ground floor, an open plan multi-colored kitchen with exposed beams, frosted glass counters and sycamore cabinetry spills into a dining area and wetbar. A stunning rear breezeway with exposed beams and wall of windows serves not only as informal dining room but as connector to a comfy media room and the Federal-era part of the home. The finely-appointed Federal wing, a traditional center hall Colonial, is a favorite for guests, with 4 cozy bedrooms, ensuite bathrooms, and charming sitting and dining areas. A beautiful blue stone terrace leads to the pool and poolhouse with wood burning fireplace that can easily be reimagined as an apartment, office or party barn. Nearby is a 5-bay garage for a serious car collection. So much land, so much potential! With multiple parcels and prospective building lots, there's also agricultural options: Currently there are grazing pastures for Black Angus cattle and five acres of a black currant crop. When a meditation workshop beckons, head to the world-renowned Omega Institute in nearby Rhinebeck, also famous for farm-to-table restaurants. Craving culture? Architect Frank Gehry's celebrated Fisher Center at Bard only 15 minutes away. 2-hour drive to Manhattan. Bring your architect to Red Hook Farmstead and custom-design this into your dream house!