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luxury houses for sale Bennington, United States

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Contract pending
49

House Bennington (United States)

Coveted Three Seminary Lane , Old Bennington Originally established in 1829 as Mount Anthony Seminary, this remarkable property first served as a boys' boarding school. In 1897, it transitioned to become the clubhouse of the Mount Anthony Country Club, a role it maintained well into the early 20th century. Now situated on 2.5 acres, this charming Colonial-style home exudes character and grace, featuring a stunning staircase, intricate millwork, 10-foot ceilings, and expansive, light-filled rooms. The generously sized 45' x 22' living room offers floor-to-ceiling bookcases and a handsome marble-surround fireplace, creating an inviting space for relaxation or gatherings. The first-floor office offers privacy. The eat-in kitchen, complete with a spacious pantry and lovely built-in china cabinets, flows seamlessly into the formal dining room. With five bedrooms, ample closet space, and three and a half baths, this home offers both comfort and practicality. The side stone terrace, accessible from both the living and dining rooms, is perfect for outdoor entertaining, making this home ideal for hosting guests. Located in the charming and historic village of Old Bennington, this is truly a must-see property.

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$610,000
5bedrooms
4bathrooms

By Four Seasons Sotheby's International Realty

45
Video

House Bennington (United States)

Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining pantry, formal dining and living rooms. The private estate includes a three car garage, four bedroom caretakers cottage, artist studio and gunite heated in-ground pool. Set on the outskirts of the historic town of Bennington offering shopping, live theatre, restaurants, horseback riding and proximity to mountain and cross-country skiing. This is a rare opportunity to own an exquisite estate property with a myriad of possibilities as a family compound or country retreat. Only 45 minutes to Albany International Airport and approximately three hours to Manhattan and Boston. All measurements approximate.

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$2,225,000
9bedrooms
7bathrooms

By Four Seasons Sotheby's International Realty

21 listings near Bennington

Nearby
19

House Shaftsbury (United States)

Come see this Charming Cape in Serene Rural Setting - nestled among rolling meadows with mountain views. This picturesque home offers the perfect blend of rural charm and modern comfort. Step inside to discover a warm and inviting country kitchen, complete with a large island, perfect for casual meals or entertaining guests. The adjacent dining area is perfect for lazy family dinners. The large living room with fireplace and built-ins offer the perfect room to curl up with a good book or jig saw puzzle while watching the snow come down. Work in your private office or unwind in the out of the way den (a versatile space that can be tailored to your needs). The spacious primary bedroom offers a peaceful retreat, while an additional bedroom provides comfort for family or guests. With two full baths, mornings are a breeze. Outside, the expansive property invites you to explore the surrounding nature, whether it???s a morning walk on this bucolic rural road greeting the early birds, expanding on the beautiful gardens or an evening spent under the stars at the fire pit toasting marshmallows. This home is more than just a place to live; it's a lifestyle waiting for you to come and put on your personal touches. Being sold As Is. All measurements are approximate.

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$499,000
2bedrooms
2bathrooms

By Four Seasons Sotheby's International Realty

Nearby
Contract pending
45
Video

House with garden Eagle Bridge (United States)

Introducing Auchincloss Farm, a distinguished gentleman's estate with a rich heritage dating back to 1865. Nestled on nearly 100 acres, this exceptional property offers unmatched privacy and sweeping panoramic views of the Green Mountains. With ties to both the iconic Jackie Kennedy and the Rockefeller families, Auchincloss Farm seamlessly blends history and breathtaking panoramic views into a truly unparalleled offering, where natural beauty, serenity, and comfort converge. The historic main house exudes timeless charm, featuring original details throughout, including a cozy wood-burning hearth, Vermont soapstone countertops, and a gourmet kitchen designed for modern culinary pursuits. Wraparound porches provide the perfect spot to take in the stunning mountain vistas, creating a peaceful retreat in every season. A fully furnished guest house adds to the property's allure, offering three additional heated garage spaces, an indoor exercise pool, two bedrooms, a full kitchen, and bath. This guest house opens up opportunities for visitors, extended family, or additional income potential. The estate is also well-equipped for versatile country living, with a well preserved historic barn and a newer, larger metal pole barn, offering abundant storage for equipment, vehicles, or farming needs. Two spring-fed ponds, apple orchards, rolling pastures, and tranquil wooded areas enhance the property's natural beauty, providing endless possibilities for recreation, agriculture, or equestrian pursuits. Perfectly positioned just three hours from Manhattan's Upper West Side, less than an hour from Albany International Airport, and minutes from the Vermont border, Auchincloss Farm offers both convenience and seclusion. Surrounded by organic farm stands and orchards, some within walking distance, this estate presents an ideal opportunity for those seeking a healthy retreat or a full-time refuge.

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$950,000
5bedrooms
3bathrooms
land 39.3ha

By Four Seasons Sotheby's International Realty

Nearby
50
3D visit

House Williamstown (United States)

Tucked in the Berkshires of Western Massachusetts, this Williamstown contemporary boasts over 7,000 sq. ft. of undeniable form and function mixed with the highest degree of finishes. It's been said that homes can be duplicated anywhere, but a setting with unique and rare attributes cannot. Gently Sited amidst a spectacular 34-acre backdrop bordering 8,000 +/- acres of protected land is incredibly rare. Architecturally designed to contour with the natural topography of the site greatly reduced disturbance when built. This multi-tiered footprint affords picturesque sunset views of the village below and Berkshire hills beyond. Watch a soccer game at Cole field from your Gunite pool, walk to the village for dinner or go hiking on Chestnut/Pine Cobble Trails right off your property...

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$1,995,000
4bedrooms
6bathrooms
land 13.8ha

By William Pitt Sotheby's International Realty

Nearby
48

House Clarksburg (United States)

Berkshires Country Estate with impeccable views! Engineered Strength and Thermal Superiority topped off with the todays technology. 78+/- acres of varied topography with meadows, timber tracts and streams complimented by some of the most dynamic views available in the area. Enjoy the warmth of the floor to ceiling wood burning stone fireplace in the great room and a wall of glass bringing the outdoors in. Open concept with gourmet country kitchen offering granite and stainless leading to the entertaining areas. Main level master suite with two bedrooms and a full bath upstairs. Geothermal technology coupled with Structural Insulated wall and roof panels make this home incredibly efficient. Just minutes to everything one could want or need in the Berkshires. RSVP open house October 19th.

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$1,275,000
3bedrooms
3bathrooms
land 31.6ha

By William Pitt Sotheby's International Realty

Nearby
25

House Arlington (United States)

Abundance of acreage at private location in Arlington, Vermont with additional Buildable Lots. Wonderful home offering a luxurious primary or secondary residence nestled in a tranquil mountain setting. With 3 bedrooms and 3 baths, the home boasts an open floor plan. The main floor offers custom mudroom/entry/laundry and a half bath. The large kitchen with breakfast bar and open flow to the dining room and deck access to expansive outdoor space for grilling and gathering in the Green Mountains. Primary bedroom with private ensuite full bath is wonderful for main floor living. Upstairs are 2 generous sized bedrooms with loads of closet space and a full bath. The attention to detail is evident throughout, from the custom-built design to the meticulously maintained interior, with wood flooring on main level added summer of 2024. The full basement offers potential for additional living space, making this home as versatile as it is beautiful. The oversized multi bay garage, complete with an automotive lift and ample storage, adds to the home's appeal, while the private drive ensures a serene and secluded lifestyle. A new driveway is currently being built for direct access off Route 7a. The total acreage is comprised of 3 lots with wastewater permits for the 2 additional buildable lots. Please see documents for additional lot and wastewater permit information. This home and land listing offers a tremendous opportunity and potential for expansion or privacy.

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$669,000
3bedrooms
3bathrooms

By Four Seasons Sotheby's International Realty

Nearby
Contract pending
28
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House Arlington (United States)

Discover this beautiful property featuring breathtaking mountain views and a bright, modern kitchen complete with marble and granite finishes. Enjoy the cozy living room, which boasts a fireplace and custom floor-to-ceiling bookcases, perfect for relaxation or entertaining. The primary suite offers a luxurious master bath and a customized walk-in closet for all your storage needs. Conveniently located on the second floor, the washer and dryer make laundry a breeze. The spacious basement provides extensive usable space, ideal for a workshop or dry storage. Nestled in a private location, you'll have easy access to Manchester, the mountains, and Bennington. Set on 13 acres of a delightful mix of open land and woods, you can enjoy nature and wildlife right from your home. The expansive 34-foot deck offers the perfect spot to take in the stunning views, while the private yard adds to the charm of country living. Additional features include a generator hookup and central vacuum system for added convenience. Don't miss out on this remarkable opportunity!

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$580,000
3bedrooms
3bathrooms

By Four Seasons Sotheby's International Realty

Nearby
16

Property North Adams (United States)

Welcome to historic North Adams, where culture, charm, and character meet! Nestled just a stone's throw away from the renowned MASS MoCA art Museum, this 3-bedroom, 3-bathroom includes a primary suite with its own private bath, and sun porch. This must-see property includes new electric and plumbing throughout, you can enjoy peace of mind knowing that this historic beauty has been carefully updated for modern living. Original hardwood floors grace the spacious living areas, creating an inviting ambiance that's perfect for both relaxing evenings and lively gatherings.

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$340,000
3bedrooms
3bathrooms
land 526

By William Pitt Sotheby's International Realty

Nearby
34

House Arlington (United States)

Discover the ideal blend of privacy and convenience in this stunning four bedroom single family home at the end of a cul-de-sac in scenic Arlington, Vermont! Recently updated, this home offers modern comfort with classic charm. Step into the open concept kitchen and living room, featuring a striking black marble fireplace perfect for cozying up on chilly days. A formal dining room sets the stage for formal gatherings, while a bright sunroom provides the perfect spot to relax all year round. The first floor also offers a bedroom suite, laundry and mud rooms. Upstairs you will find a spacious primary suite with plenty of room to unwind. Down the hall are two guest bedrooms and a study offering flexibility for work or play. Relax on the covered front porch or take in the sun on the back deck, there's ample garden space as well as a shed for extra storage. The two car attached garage boasts an EV charger. This house is a must see for anyone seeking a private oasis with easy access to all Vermont has to offer.

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$840,000
4bedrooms
4bathrooms

By Four Seasons Sotheby's International Realty

Nearby
Contract pending
31

Property North Adams (United States)

Embrace the perfect blend of comfort and charm with this enchanting Colonial home, meticulously updated and ready to welcome you. Bask in the serenity of mountain vistas and the natural beauty that surrounds, visible from every window of this delightful residence. Fresh, inviting interiors and a newly renovated kitchen set the stage for a home that's both stylish and practical. The first-floor bathroom has been thoughtfully updated, enhancing the home's appeal. Experience the ease of maintenance with luxury vinyl flooring on the ground level, complemented by timeless hardwood floors on the second story. Modern living is a breeze with a newer on-demand hot water heater, robust 200 amp electric service, updated windows and doors, and a smooth asphalt driveway. Step outside to an expansive front porch, an idyllic spot for soaking up the breathtaking mountain views, or indulge in relaxation in the privacy of your backyard hot tub. Additional conveniences include a spacious shed, providing ample storage for all your needs. This home is not just a residence; it's a sanctuary that has everything you desire and more. Nestled in an idyllic location that offers tranquility without sacrificing accessibility, this home is the retreat you've been searching for. Close enough to amenities yet far removed from the daily hustle, it's a rare find that's sure to capture your heart. Don't let this gem slip away!

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$229,000
3bedrooms
1bathroom
land 2,064

By William Pitt Sotheby's International Realty

Nearby
Contract pending
40

Property with garden Cambridge (United States)

100 East Main Street, Cambridge, NY 12816

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$378,000
3bedrooms
2bathrooms
land 1,578

By Four Seasons Sotheby's International Realty

Nearby
25

Property Cambridge (United States)

Gracious Queen Anne Victorian and carriage house with two updated apartments for rental, guest cottage or studio. ( Both units currently rented for great offset for costs) The classic home has original woodwork, wood floors, leaded & stained glass windows, original built ins, remodeled bath with radiant floor heat, a sunny kitchen with pantry space, stool counter, granite counter, farm sink. Fantastic attic space, gas fireplace, and new propane furnace. There are two large porches, a porte-cochere, established gardens and plantings. This property is beautifully maintained and updated. The property is located on a lovely side street in the quaint village of Cambridge. Main house has also been used as an airbnb.

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$415,000
3bedrooms
2bathrooms
land 1,093

By Four Seasons Sotheby's International Realty

Nearby
Contract pending
39

House Arlington (United States)

Discover the perfect blend of homeownership and financial freedom with this incredible opportunity. This rare property comes with an income-generating apartment, allowing you to offset your mortgage, boost monthly cash flow and enhance your investment portfolio all while living in your dream home! Perched on the crest of Sunrise Lane, this beautiful residence offers a perfect blend of timeless charm and modern comfort. The heart of the home features a thoughtfully updated kitchen with sleek granite countertops, stainless steel appliances, and plenty of cabinet space???perfect for both everyday meals and gourmet cooking. Embrace the Vermont winters with a pellet stove that not only adds warmth but also enhances the cozy atmosphere of the living space.The second-floor primary suite is a sanctuary within a sanctuary, offering privacy and peaceful escape with modern amenities like an updated ensuite bathroom and generous closet space. Enjoy the convenience of a second-floor laundry room???another thoughtful update that makes daily life a little easier. The partially finished basement adds valuable living space to the home, offering rooms that can be used as a media room, home gym, office, or playroom. Gather with friends and family around the fire pit creating memories or wander through beautifully established gardens, bursting with perennial blooms and mature trees. Two barns and a shed offer plenty of extra space for equipment and hobbies.

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$595,000
4bedrooms
4bathrooms

By Four Seasons Sotheby's International Realty

Nearby
13

House Florida (United States)

Recent New Build- log home offering 2 bedrooms with bonus loft and 1 full bathroom near North Adams and all the Berkshire attractions yet steps from your outdoor playground with hiking, fishing, white water activities on the Deerfield River and downhill / X-Country skiing and snow shoeing for the winter months all along the iconic Mohawk Trail for your year-round enjoyment. Walkout basement with washer and dryer with expandable space. Call today.

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$360,000
2bedrooms
1bathroom
land 6,111

By William Pitt Sotheby's International Realty

Nearby
Contract pending
20

House Wilmington (United States)

Here is your opportunity to put finishing touches on an almost completed interior Southland log home. Soaring ceilings and natural create inviting spaces. Open floor plan leads to creative layout for furniture placement. Location has VAST access as well as bring across from Haystack Golf for fabulous year round fun and dining at the Stack! Just Minutes to the entrance to the Hermitage Club and Mount Snow as well as downtown Wilmington for quaint shopping days. Sale is subject to seller installing water and sewer in the Spring so projecting a Fall Delivery.

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$665,000
3bedrooms
3bathrooms

By Four Seasons Sotheby's International Realty

Nearby
46

House Dover (United States)

Located in between Mount Snow Ski Resort and The Hermitage Club, this stunning farmhouse built in 2016 offers mountain living with a blend of modern amenities and rustic charm. 5 bedrooms and 5 baths, this ski home features an attached garage with epoxy floors,electric car charger, along with a rear door for direct access to VAST trails for the snowmobile enthusiasts. Above the garage, discover a heated and air-conditioned art studio, perfect for creative endeavors. Reclaimed brick floors grace the mudroom, powder room, laundry, and pantry, while warm white oak floors flow throughout the home. The chef's kitchen is equipped with Sub-Zero and Wolf appliances, ideal for culinary enthusiasts. A combined living and dining room showcases a stone wood-burning masonry fireplace, providing both warmth and ambiance. Step outside to the expansive outdoor deck overlooking the wooded landscape. The home has direct access to the hiking, biking, and snowmobile trails adjacent to the property. The primary suite on the first floor boasts cathedral ceilings and ample natural light, along with a luxurious primary bath featuring a steam shower and soaking tub. Upstairs, three additional bedrooms, two baths, an office/study await. The finished lower level offers an additional en suite bedroom and a large playroom, with access to the backyard & hot tub. Brand new detached car storage barn for your special car collection or boat for Lake Whitingham. Could be converted to indoor pickle ball.

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$2,997,000
5bedrooms
5bathrooms

By Four Seasons Sotheby's International Realty

Nearby
Contract pending
44

House Williamstown (United States)

Historic Elegance Meets Modern Luxury at the Gracious Holiday House Nestled in the heart of the Berkshires, Holiday House is a testament to the timeless allure of Williamstown, MA. This magnificent estate, dating back to circa 1790, is perched on over 90 acres of serene, bucolic landscapes, offering fabled views that sweep across the countryside. As you approach the residence, you are greeted by a property that has been meticulously cared for, updated and thoughtfully renovated and expanded, preserving its historic charm while embracing the comforts of modern living. The home boasts five well-appointed bedrooms and four full bathrooms, each space crafted with an eye for detail and a reverence for its storied past. The gourmet kitchen is a chef's delight and the heart of the home, featuring top-of-the-line appliances and an open layout that leads to a comfortable living/dining area as well as a spacious family/media room with a wood burning fireplace, all framed by breathtaking views. The original cape section of the home exudes elegance with its formal dining room, whimsical bar at the entrance, and a cozy den/office with a wood-burning fireplace. The formal living room is a showcase of antique grandeur, complete with a stunning fireplace and a brick bread oven is a nod to the home's rich heritage. The first floor also features a private first floor bedroom suite with a full bath which adds to the gracious feel of the property. Two separate staircases lead to the private sanctuaries of the second level. The primary suite is a retreat within itself, featuring two sitting areas, a romantic fireplace, and an ensuite bathroom. The additional bedrooms offer versatility, with one ensuite and two others sharing a full bathroom. Holiday House is as much about its enchanting custom interiors as it is about the splendor of its breathtaking grounds. A three-car garage, a charming four season out building perfect for artistic or literary pursuits, and a gracious patio set the stage for unforgettable moments, whether it's hosting lively gatherings or enjoying quiet evenings under the stars. Located just 10 minutes from Jiminy Peak ski resort, Williams College, the Clark Art Institute, and 25 minutes from MASS MoCA, this property is not just a home it's a lifestyle. A fine level of living awaits at Holiday House, where history is honored, and luxury is lived.

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$1,389,000
5bedrooms
4bathrooms
land 36.8ha

By William Pitt Sotheby's International Realty

Nearby
41
Video

House Dover (United States)

Located in the Snow Vidda Condominium Complex, this stunning 4-bedroom, 3-bath townhouse offers the perfect blend of comfort, style, and convenience. Located adjacent to the renowned Mount Snow Ski Resort, this home is a skier's dream, providing easy access to world-class slopes and year-round mountain adventures. Step inside this unique townhouse and be greeted by a custom-designed mudroom, tailored to meet all your gear storage needs after a day on the mountain. The interior is tastefully appointed, offering a seamless blend of modern amenities and cozy mountain charm. With a spacious, open-concept living area, a gourmet kitchen, and thoughtfully designed bedrooms, this property is truly turn-key. The finished lower level hosts the lower level bedroom and bath along with a playroom with 4 extra bunk beds for the kids and their friend to gather. Whether you're looking for a serene retreat or a lively gathering place, this townhouse caters to all your needs. Relax by the fireplace after a day of skiing, entertain guests in the expansive living space. Don???t miss this rare opportunity to own a piece of paradise in the sought-after Snow Vidda community, just steps away from the best skiing and outdoor recreation Mount Snow has to offer. Just a short drive to The Hermitage Club, area golf and historic downtown Wilmington.

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$999,998
4bedrooms
3bathrooms

By Four Seasons Sotheby's International Realty

Nearby
27

House Wilmington (United States)

Escape to your Vermont with this charming 5-bedroom, 3-bathroom farmhouse on 47.7 acres, just a short drive from Mount Snow Ski Resort and The Hermitage Club. This beautifully preserved home seamlessly blends historic charm with modern updates, offering a warm and inviting ambiance perfect for year-round living or a seasonal retreat. Step inside to discover a well-appointed kitchen featuring quartz countertops, modern appliances, and an island that invites gatherings after a day on the slopes or or a day on the lake. The spacious dining room boasts rich wood accents, creating the ideal setting for hosting family dinners or entertaining guests. The home???s layout includes cozy yet spacious living areas, complemented by a wood stove to warm you during Vermont's crisp winters. Upstairs, the five bedrooms provide ample space for family and guests. Outside, the farmhouses' porch offers a perfect spot to savor morning coffee or evening sunsets. The property???s expansive acreage features a mix of open fields, wooded trails,over 100 apple trees and rolling terrain, perfect for snowshoeing, hiking, or enjoying nature. A ski enthusiast's dream, this home is situated near top-tier skiing, making it the perfect basecamp for winter adventures. Whether you're seeking tranquility or adventure, this Vermont farmhouse is a rare find that invites you to make memories in every season. Lake Whitingham and Lake Raponda are just a short drive away for summer fun.

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$749,000
5bedrooms
3bathrooms

By Four Seasons Sotheby's International Realty

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