Millbrook NY Real Estate & Homes for Sale

Welcome to your dream farm retreat nestled in the picturesque foothills of the Berkshire mountains! This sprawling property spans just under 175-acres with a rich history, once serving as a prominent dairy farm and now flourishing as a horse farm. Here, you will find a stunning array of farm buildings, lush pastures, paddocks, a sprawling pond and acres of wooded mountainside. The main residence, a classic center hall colonial, offers grandness and comfort with its 5-bedrooms and 4.5-bathrooms. The charming interior is adorned with 4 fireplaces, wide plank pine flooring and a spacious layout perfect for entertaining. Admire the beauty of the landscape from the inviting wrap-around porch or take a dip in the refreshing in-ground pool. Adjacent to the main house, a large carriage house provides additional living space for possible tenants with a first floor 4-bedroom apartment and a second floor 1-bedroom apartment, accompanied by an attached 2-car garage. A quaint one-bedroom cottage tucked away on the property offers even more accommodation options. The farm itself features a vast array of well maintained barns adorned with multiple cupolas. The main barn includes ten 12'x14' horse stalls, private office space and an extensive second floor area with multiple options for its use. Outside, you'll find three paddocks, a round pen, four silos and several large and small storage sheds ensuring ample space for all your farming needs.

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 master 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 master guest room with soaking tub and deck with views. Two bedroom suites with ensuite bathrooms, charming children's 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 & pool house with full kitchen & tennis court. Two building maintenance court contains a pumping system for irrigating the lawns and gardens.

A truly rare opportunity to own "Dragonfly Farm", one of the most unique estates in New England which has been featured in House & Garden and many architectural books. The estate compound began in the 1700s with the construction of the mill and the millkeeper's house (which now serves as the guest house). The Federal style stone house was added to the property in the early 19th century. In the 20th century, this main house was expanded by owner and architect Heathcote Woolsey. It was then owned by the Hammerstein family (of Rogers & Hammerstein fame). The current compound includes the 5 bedroom residence, 2 bedroom guest house, antique barn, office/gym/game room complex above the 4+ car garage, caretaker's house and a stone cabana. Unique features of the main house include a gracious foyer w/ curving staircase, dining room w/ opposing fireplaces, vaulted kitchen w/ stone walls/opposing fireplaces/hand hewn beams & a stunning solarium/family room. Leisure time will find you enjoying tennis, soccer, basketball, golf chipping, archery & the gunite heated pool.

Two lots being sold together- included in the sale of 59 Fuller Mt. is 61 Fuller Mt with an additional .92 acres and additional taxes of $1489.00. Build your dream house, just 5 minutes from Macedonia State Park for hiking, biking , fishing ,etc. Minutes from Kent town center.

Sharon Cottage on 10+ acres - A spectacular parcel of land with building potential and a well-kept 2-bedroom, 1-bath cottage greeting the 10 prestigious Sharon, CT acres. The upper building site was approved in 2011 and awaits the vision of its next land steward. An existing Cottage on the property offers immediate use and enjoyment of the homestead. Views from the upper lot, privacy for both the Cottage and potential building site, and only minutes to town. This property offers the ultimate country retreat and a blank canvas for those who dream of creating a homestead that echos their lifestyle. Minutes to: Sharon Town Beach, Mohawk Ski Area, Sharon Audubon, Millerton, NY, Salisbury, CT, Metro North's Wassaic Station.

Step into tranquility with this fully renovated Mid-Century gem tucked away on a private drive. Nestled on 5 acres of wooded bliss, this home offers the perfect blend of privacy and nature. Enjoy the serene surroundings from your brand new deck and porch, where every sunset feels like a moment of pure magic. With a finished basement offering additional space for entertainment or relaxation, this home is a true sanctuary for those seeking tranquility and style. Welcome home to your peaceful retreat.

Classic Kent Colonial in the heart of the Village. Custom built in 2010 by a master craftsman, this 3886 sf home has traditional taste, style and quality with modern day living sensibilities. Purposefully designed boasting the grand living room with wood beams gracing the cathedral ceilings. A generous fireplace, French doors, custom oversized windows with transoms this room can host a party or make an intimate fireside retreat. The kitchen is both top of the line and also a gathering spot of its own. The Wolfe range is a chef's delight. Eat at the island bar or enjoy the breakfast nook. Detailed in cherry wood and designed by Hunt Country the kitchen is amazing. The main floor entails a formal dining room, half bath room and a large screened porch. There is a main floor primary ensuite that adjoins a study that was designed for in-law habitation. The second floor offers three bedrooms one which is an additional primary suite. The bathroom is both spacious and sumptuously pampering. All this wrapped in solid New England building ethos. Additional space include a full height third floor presently storage space but is ready made for conversion if desired. The same applies to the basement that has 9 foot clearance. But wait...the guesthouse offers a one bedroom suite retreat with a small kitchenette for friends, pj parties, additional office or she shed! The grounds are simply amazing with professional landscaping from Kent Green House. Gardens are resplendent in

New Home proposed to be custom built to the wants and needs of the contract purchaser on this beautiful lot in St. John's Peak. Pricing is based on a 2 story 3300 square foot house size. Final price, house plan and specifications to be agreed upon between buyer and builder. Home to be built by Multi Award Winning Litchfield county builders Ground Breakers. Builder has built several homes in the subdivision as well as many other homes in CT. Lot has been cleared and all engineering data has been updated to move forward as soon as plans and specs are finalized. Financing if necessary to be a construction to perm mortgage. Photos are an example of homes built by Ground Breakers and are not necessarily what is proposed in this home listing. Taxes based on land only.

Welcome to 333 Kent Rd. This is a beautiful opportunity to own a mixed-use property in Kent featuring two fully rented units and a 120-seat restaurant with an updated kitchen and full bar on the main level. The possibilities are endless. Bring your imagination. This property has been wonderfully maintained by the current owner. Located across the street from Bulls Bridge, a well-known covered bridge, as well the Appalachian Trail. Hiking, biking, and nature are just across the street! Located in the picturesque town of Kent Ct, just south of the center of town, boasting high-end stores, restaurants, and boutiques. Let your imagination run wild with all the possibilities!

Totally Private Top of the World Setting with Monster Catskill Views. 10-Min to the Center of Millerton NY/Sharon CT & 15-Min to Metro North Train. Graciously Scaled Rooms Throughout. 4 Fireplaces. The Ultimate Swimming Pool & Pool Area Complete with: Hot Tub; Outdoor Kitchen; Fireplace & Large Stone Terrace. Tennis Court. 3-Car+ Attached Garaging. 6 Paddocks with Run-In Sheds + Riding Ring & Barn. BIG Value for the Dollar!

Originally constructed in 1739, this delightful Antique is nestled in Kent's picturesque Flanders Historic District, right along scenic Cobble Road. Steeped in history, the home boasts many original features, from its wide board floors to the central chimney that serves two fireplaces in the living and dining rooms, not to mention the charming hand-hewn beams overhead. Meticulously maintained, the original house has undergone a thoughtful expansion, creating a generous open-concept space that seamlessly blends a modern kitchen with high-end stainless steel appliances and butcher block counters, flowing into a sun-drenched dining area and seating area adorned with custom built-in bookcases. Venture upstairs to discover the primary bedroom with its luxurious en suite bathroom, flanked by two additional bedrooms sharing a bath. The walk-out lower level offers a versatile large room that could easily serve as an overflow bedroom, accompanied by a full bath. The property also features a grand party barn and a separate studio, adding an extra living space ideal for a home office or a future guest home. Outside, the 2.4-acre property borders Cobble Brook and showcases a serene pond, enchanting vegetable and flower gardens, a charming grape arbor, and a fruitful orchard, creating an absolutely idyllic setting.

A remarkable opportunity to own and renovate a home across from Sharon Hospital in the Village of Sharon, Ct. This home is in the center of Sharon and all that offers, such as the restaurants, library, hospital and all the associated doctor's offices. This home is served with both Town water and sewer and is minutes away from the train station to NYC.

Charming Cape in Ideal Location - This lovely Cape Cod home located on an amazing lot in idyllic Sharon CT is now available for sale. Cross the threshold of the extra deep wrap-around porch and enter the home with hardwood floors and generous proportions. The light-filled kitchen has a dining area with a large bay of bowed windows overlooking the side yard. A laundry room/mudroom is adjacent. The living room features an extra large double-height stone fireplace that has doors to a heated sunroom with wrap-around windows and access to the back patio with gorgeous views. The main floor primary bedroom has its own stone fireplace, a private sunroom, an en-suite bath, and ample closet space. Ascend to the second floor to discover two guest bedrooms and a full bath, providing comfortable accommodations for family or visitors. A detached two-car garage with loft storage space accompanies the property, featuring an attached room housing an exercise pool, perfect for relaxation and fitness. Enjoy the peaceful ambiance of country living, with convenient proximity to local amenities including in-town shopping, the Sharon Playhouse, Indian Mountain School, Hotchkiss School, and easy access to NYC train transportation. Don't miss the opportunity to make this tranquil retreat your own.

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 8,872 sq ft 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 fireplace, 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 8,872 sq ft 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 fireplace, 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.

107 Main Street is located in the heart of Sharon's Historic District - a tucked away convenient village setting. Originally the carriage barn to a neighboring home, it was reimagined by a previous architect owner. Brimming with character and charm, this 4 bedroom, 2 and a half bath home offers a spacious & historic layout. The ground floor has 2 entrances: a main entrance foyer, and a sun-lit mudroom with slate tiles which opens to a large kitchen with a central island and new appliances. Next to it, a separate formal dining room with a secondary staircase that leads to the upstairs bedrooms. The cozy family room has custom built-in cherry cabinets and bookshelves, a large double-flue fireplace and french doors that open to an expansive, peaceful cedar deck and a bluestone patio, providing ample outdoor gathering space. Impress your guests with the full-height great room ceilings from the main entrance, two large skylights and a second fireplace. Entertain in the sunny living room that overlooks an established perennial garden. Continuing upstairs by way of a wide formal staircase, you'll find a lofted second level with exposed wooden beams throughout. Off the loft is the primary bedroom with a Palladian window, high ceilings, and a walk-in closet. Through the opposite side of the loft, are 3 additional, and generously sized bedrooms with another full bath, newly renovated. This rich in character historic home off the Sharon Green is not to be missed.

Very Special & Architecturally Significant Home just off Cobble Road in Kent and featured in the NY Times: 4 bedrooms, 4.5 baths, room to spread out, and full of natural light. With just over 2 acres and open views, this wonderfully maintained Frank Lloyd Wright-inspired home sits on Cobble Heights Road about 5 minutes from downtown Kent. Built for entertaining and a floor plan that creates privacy and separation within the home. Terrific location, with convenience to NYC via Metro North (20 minutes to Harlem Valley Wingdale). If hiking is your thing, trails abound including Kent Falls State Park, and the town of Kent is one of the more sought-after in Litchfield County, with many highly rated restaurants and shopping options. Less than two hours to NYC but a world away in bucolic Litchfield County.

Chic In Town Period Home Set on Prominent Upper Main St. 4 Bedrooms, 3.5 Updated Baths. Central A/C. Welcoming Public Spaces Loaded with Charm. Large Living Room with Fireplace & Floor-to Ceiling Windows. Inviting Family Room with Wood Stove & Doors to Private Stone Terrace. Formal Dining Room with Built-Ins. Screened Porch. Open Eat-in Kitchen with Butler Pantry & Back Staircase. 2 Primary en-suite Bedrooms + 2 Additional Bedrooms. Coveted Historic District Gem!

Beautiful contemporary on 3.33 private acres surrounded on three sides by 0pen Space, providing exceptional privacy and views of pastures and hills. The great room ( living room/dining room) has a 16' cathedral ceiling, and floor-to-ceiling, two-story windows looking out onto gardens and protected land. Large country kitchen with Sub Zero, Miele, and Wolf appliances and a large butcher block central island. There is a working wood stove in the kitchen. The back kitchen wall is also floor-to-ceiling glass, with a wrap-around deck connecting the kitchen and dining room. This home offers three large light-filled bedrooms, and 3 full and one half fully renovated baths, with two of the bathrooms having heated floors. The primary bath offers an immense shower, a deep soaking tub, and a heated Toto bidet. Metal roof, a brand new state-of-the-art geothermal system, and new front and back decks. Long granite-lined gravel driveway with a center island. Large open yard with professional landscaping, and an Enchanted Forest, complete with a mini castle, log cabin, medieval size fire pit, swings, climbing ropes, and magical trails through the woods. This home is warm and welcoming, light-filled and comfortable, move-in ready.

Welcome to 1 Jackson Hill Road. With its refinished wood floors and rustic ceiling beams this home blends modern comfort with historic details. The spacious living room with its cozy fireplace, flows naturally into the well-appointed kitchen and formal dining room. Natural light pours into this delightful cottage from the dining room bay window and the sky lights in the renovated bathrooms. Set off the main living area is the first floor primary en suite with ample closet space and soaring ceiling height. Upstairs the second bedroom boasts sturdy built-ins. The enchanting curb appeal is created by mature landscaping and flourishing perennials. A detached garage provides additional storage.

Privately set, on a near 2 acre lot, with inground pool, spa & cabana, in Sherman's premier golf community, this grand 6500+ SF plan showcases 9 ft & vaulted ceilings, Mahogany floors throughout, 4 fireplaces & more! A grand foyer with circular stair, herringbone mahogany floors & dramatic lighting creates an impressive entry. Framed by a classic formal dining room & living room with mantled fireplaces, built ins & quality trim exudes elegance. Gather in the Chef's kitchen with marble counters, center island plus a breakfast bar & a spacious dining area leading to the Trex deck & an enticing IG Pool with slide and cabana! The kitchen is open to the vaulted family room, with floor to ceiling stone fireplace, the same gorgeous hardwood floors & French doors to the Trex deck and lushly landscaped yard. Views of the pool & private yard are also seen from the main level owner's suite, with spa bath, double sinks, jetted tub & marble tile. An exciting upper level with wrap balcony showcases 3 spacious bedrooms with full baths, ceiling fans & lots of closet space plus a cozy loft for reading or relaxation & an adjacent private office. A spacious bonus room over the 3 car garage is ideal for game room, bunk room or extended guest stays. Manicured grounds, gunite pool, stone patio, cabana w/full bath & outdoor shower, 3 car gar & more The Club at River Oaks offers golf & social memberships (optional),clubhouse, pool, gym, restaurant, bar & pro shop! Not to be missed!

Craft your dream home from the ground up with this rare built-to-suit offering set on a sprawling 5.46 acre lot on Long River Road in River Oaks Country Club, a private gated golf course community in Sherman, CT. This 4 bd / 4.5 bath / 3,759 sq.ft. open-concept residence with main level master seamlessly connects a chef's kitchen (w/ pantry) to an elegant dining area and a living room w/ cozy fireplace. Elevate outdoor gatherings on the sun-drenched patio with sweeping long views (optional POOL can be added). Club River Oaks features an 18-hole, par-70 golf course that blends with the natural terrain of the Berkshire foothills. Enjoy amenities like tennis courts, heated swimming pool, fitness facilities, fine or casual dining, Golf Pro for private lessons and summer golf camp for kids. Various membership options are available. Situated just 60 miles from NYC, 45 miles from WHITE PLAINS, this prime location allows easy commuting. The charming town center, 5 min away, offers community amenities: a library, parks, pavilion, sandy beach, and town boat slips on Candlewood Lake. Nearby catch & release trout fishing, acres of hiking & biking trails + skiing at Mohawk Mountain. Sherman is known for low taxes and excellent PK-8 school, making this location a rare gem. Pictures are for reference, home is TO BE BUILT and FULLY CUSTOMIZABLE. Don't miss the chance to customize an exceptional property where every detail mirrors your unique taste and individuality. Land only MLS 170615535

Welcome to 34 Jackson Hill Road, a recently remodeled retreat just a mile from the quintessential Sharon center. This ultra-chic haven is surrounded by apple trees and boasts captivating views of the CT/NY mountain range. Nestled into the rolling hillside, the black/white facade home features 3 full bedrooms, offering the sleeping capacity of 4. This residence is designed for sophisticated living, with an array of inviting spaces spread across both floors. Each floor presents real wood-burning fireplaces, access to balconies or patios, and full baths. The renovation includes new doors, trim, floors, plumbing, electrical, heating, and cooling systems. The main level seamlessly integrates the living, kitchen, and dining areas into an open floor plan. The kitchen is a culinary delight with white shaker cabinets adorned with brush gold hardware, stainless steel appliances, and a substantial 7-foot island. Recent upgrades encompass brand new hardwood floors with a rich dark chestnut stain, slate foyer tile, a new garage door, front walkway, and an architectural shingle roof. Conveniently situated just minutes away from shopping, restaurants, Route 4, and the metro north station, this property is accessible and commuter friendly. With its unparalleled combination of modern elegance and thoughtful updates, 34 Jackson Hill Road stands out as a distinctive and unmatched home in the current market. Welcome home to 34 Jackson Hill Road, where luxury meets tranquility.

Surrounded by breathtaking panoramic views, this newley home offers the ultimate retreat for golf enthusiasts. This single-level residence in the prestigious community of Club River Oaks boasts a variety of amenities tailored to enhance your experience. The generous gourmet kitchen provides the perfect setting for post-game gatherings. Unwind in the open-concept, spacious living areas, where a cozy fireplace and gorgeous views offer the ideal backdrop for relaxation and camaraderie. The main level primary bedroom is designed for comfort with two walk-in closets and a generous bathroom, complete with standing soaking tub. The sprawling deck enhances the allure of this home with lush views of the gently rolling fairway. With direct access to the golf course, every day is an opportunity to hone your skills and indulge in the sport you love. Club River Oaks features an 18-hole, par-70 golf course and amenities include tennis courts, a heated swimming pool, fitness facilities, and dining options ranging from fine to casual. The club also provides access to a Golf Pro for private lessons and hosts a summer golf camp for kids. With various membership options available, there's something for everyone. This is an unparalleled location. Enjoy boating on nearby Candlewood Lake, fly fishing on the Housatonic, and hiking on the Appalachian Trail, all just minutes away from your piece of paradise. This residence offers the perfect blend of tranquility and convenience at your doorstep

This colonial home, built in 1824, exudes timeless elegance with its wide-board wood flooring, classic paneling, and not one but two charming fireplaces. The expansive walk-up attic adds to its allure, offering ample space for storage or potential expansion. And with a picturesque 1.25-acre setting featuring a meandering brook in the backyard, this property truly offers a serene escape from the bustle of everyday life. With a bit of attention and care, this house has the potential to be transformed into a stunning showpiece. Whether it's restoring the original features to their former glory or introducing modern updates while preserving its historic charm, there are endless possibilities to make this house truly shine. It's a delightful blend of historical character and natural beauty, offering a unique opportunity for anyone looking to create their dream home.