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luxury houses for sale Canaan, United States

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Farmhouse Canaan (United States)

Originally built in the year 1800 on one the areas most historically significant roads lies this delightful antique farmhouse brimming with original details and charm. Perched above the road with its wrap around porch you are immediately transported to a simpler time where quality and beauty mattered. Further selling the vision, the periphery of your view is flanked with mature trees and one of two large barns providing a nostalgic aesthetic and endless opportunities. The barn closer to the home contains a garage for sheltered parking and the ability to create a guest house, work studio, private gym or anything you can dream up. In fact, there's room for all of those options within the same structure. A serene hilltop view in the distance beckons you to walk through the more than five and half acres of lawn, meadow and fruit trees to the second barn structure to continue dreaming up the possibilities. Currently this space is absolutely perfect to host outdoor dinner parties and gatherings with a bucolic view. The interior experience begins in the entry parlor, anchored by a traditional wood-burning stove. Original wide plank painted floors flow seamlessly into a spacious dining area bathed in natural light. Adjacent to this space, the modernized kitchen offers optimized storage solutions and updated appliances. The main level extends toward the rear of the residence, where the family room features stunning beamed ceilings that evoke a historical atmosphere. Completing this floor is a versatile adjoining room, ideally suited for guest accommodations or a home office and also conveniently hosts the laundry room. Up the wooden stairwell from the entry parlor three bedrooms and a bathroom surround the landing which has enough room to be its own library/reading space. The bedrooms are quite large for the era continuing this property's themes of charm, beauty and modern comfort. Just minutes away from Queechy Lake, where residents can enjoy access via an annual pass, its prime location offers easy reach to Chatham, Ghent, and Hudson on the New York side, while Great Barrington, West Stockbridge, and the Berkshires are equally accessible. Whether you are looking for a full-time residence or a perfect weekend retreat from NYC or Boston, this home serves as an ideal destination.

… 
$825,000
3bedrooms
2bathrooms
land 2.3ha

By Four Seasons Sotheby's International Realty

21

House Canaan (United States)

Welcome to 13149 NY 22, Canaan, NY 12029—a beautifully updated 3-bedroom, 1.5-bath ranch set on two open, usable acres. This home has been thoughtfully refreshed from top to bottom, offering true ease of living in a peaceful countryside setting. Step inside to find gleaming wood floors throughout, freshly painted interiors, and renovated bathrooms with crisp, modern finishes. The efficient single-level layout provides comfortable flow between the bright living spaces and the three well-sized bedrooms. Recent improvements include a brand-new roof, ensuring years of worry-free ownership. An attached two-car garage adds convenience and storage, while the expansive yard gives you plenty of room to garden, relax, or simply enjoy the quiet surroundings. Whether you're downsizing, seeking a weekend retreat, or looking for a low-maintenance full-time home, this ranch delivers a perfect blend of comfort, style, and practicality.

… 
$399,000
3bedrooms
2bathrooms
land 8,094

By William Pitt Sotheby's International Realty

58 listings near Canaan

Nearby
Contract pending
34
3D visit

Property with garden Richmond (United States)

Welcome home! This magnificent 13.3-acre estate is rich in history and brimming with enchanting features. Nestled in a county setting, this property offers a connection with the outdoors for nature lovers and recreational activities. A low-maintenance wild garden of perennial flowers and shrubs produces a kaleidoscope of colors during the spring and summer seasons. A large, private office area with high-speed internet provides a productive ''work from home'' environment. The first floor features an eat-in country kitchen with an antique Glenwood stove. The formal living room, with its wood-burning fireplace, is ideal for cozy evenings. The sitting room, complete with built-in bookshelves, is perfect for a home library or study. A large addition boasts vaulted ceilings, adding grandeur and space to the home with versatility for a home office, first-floor primary bedroom, family room or guest quarters. The formal dining room, featuring built-in cabinetry, is perfect for hosting dinner parties. The sunroom, featuring a fountain pond, is bathed in natural light and offers a serene setting. Additionally, the first floor includes a laundry room and a full bathroom, as well as an enclosed four-season porch. The second floor includes four bedrooms, offering peaceful retreats for family members or guests. A full bathroom serves the upstairs bedrooms, and a hobby room provides an ideal space for crafts, projects, or as an additional study area. The large barn is perfect for storage, farming, hobbies, or even transforming into a creative space. The two-car detached garage includes a finished space above, providing a perfect spot for a potential home office, studio, or guest accommodations. Further enhancing the property is a brand-new heating system, new septic and a whole-house generator. Steeped in history and surrounded by beautiful gardens and pastoral views, this property is more than just a home--it's a lifestyle.

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$685,000
4bedrooms
2bathrooms
land 5.4ha

By William Pitt Sotheby's International Realty

Nearby
23

House Austerlitz (United States)

Experience idyllic country life and the best this area has to offer in this charming wood shingled house. Situated on two acres, this three-bedroom cape has an updated kitchen with stone counters which opens into the dining room. The spacious living room has a brick fireplace, built-in shelves and lovely French doors that open into a four-season heated sunroom with a vaulted ceiling and large windows that look out onto the property. Glass doors open onto a small porch that leads to the backyard. Enjoy days and evenings relaxing or entertaining outdoors with the fire pit, stone patio and the clawfoot tub converted into an outdoor shower. Upstairs are three bedrooms and a full bath. The large primary bedroom has double closets. Additional finished space adjacent to one bedroom could be used as an office, playroom or studio space. Finished space in the basement contains a cozy den, an exercise area, the laundry with a utility sink and a separate storage room. Two car garage opens directly into the kitchen and a convenient first floor half bath. EV/RV chargers. Just minutes to Beebe and Harvey Mountain State Forests with thousands of acres for hiking, many local ski options, Tanglewood, Berkshires cultural offerings and Chatham Village restaurants, shops and movie theater. A short drive to Hudson and Amtrak. Come visit this charming home in an ideal location!

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$499,000
3bedrooms
2bathrooms
land 8,094

By William Pitt Sotheby's International Realty

Nearby
Contract pending
47
3D visit

House Richmond (United States)

Just around the corner from world-renowned Tanglewood, this exceptional Richmond property offers a truly prime Berkshires location-- where music, culture, and natural beauty meet. Set on just over five picturesque acres with shared ownership in a charming small pond, the setting is as special as the home itself. Beautiful open landscaping creates an inviting approach, with sweeping lawns and thoughtfully maintained grounds that enhance the sense of privacy and serenity. The home itself is bright and airy, filled with natural light and designed for both comfortable everyday living and gracious entertaining. The kitchen is the heart of the home, seamlessly open to a sunny breakfast nook and a sun-filled family room-- perfect for gathering with friends and family. A large pantry provides exceptional storage and functionality. For more formal occasions, enjoy a separate dining room, elegant sitting room, and formal living room. A heated sunroom offers year-round enjoyment, while a dedicated first-floor office/library provides ideal work-from-home flexibility. Upstairs, you'll find four spacious bedrooms and two full bathrooms, offering ample room for family and guests alike. Practicality meets versatility on the main level with a convenient laundry/mudroom and half bath located just off the garage. Above the garage, a finished bonus space with its own full bathroom presents endless possibilities-- whether as a private studio, guest suite, bedroom, or additional family room. In a highly desirable Richmond location near Lenox and all that the Berkshires have to offer, this property combines space, light, and flexibility with an unbeatable address close to Tanglewood. A rare opportunity to enjoy quintessential Berkshires living.

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$1,050,000
4bedrooms
4bathrooms
land 2.1ha

By William Pitt Sotheby's International Realty

Nearby
30

House Austerlitz (United States)

Welcome to Chicory Hill House, a unique designer home set at the end of a long private driveway on 20 beautiful acres located in Columbia County, prime Hudson Valley. The property features pastoral views, a year-round creek, and a small waterfall woven into the landscape.Following an extensive high-end renovation and infrastructure overhaul, the original 1985 contemporary has been transformed with remarkable artistry, craftsmanship, and thoughtfully integrated modern systems. Triple-paned Austrian-engineered windows and sliding doors flood the interiors with natural light while providing outstanding insulation and quiet, and looking out onto your own private field.Major upgrades include new James Hardie concrete siding, a new roof, updated electrical and plumbing systems, new water pump infrastructure, all new split-unit heating and cooling systems, and solar panels, creating a home that is both highly energy efficient and deeply considered.The main living spaces blend warmth, texture, and refined modern design. Wide plank white oak flooring runs throughout the upper levels, while the living room centers around a dramatic floor-to-ceiling fluted marble wood-burning fireplace. The adjacent dining area includes a built-in entertaining station with an ice maker and wine fridge, ideal for hosting gatherings large and small. Walls of glass open directly onto a generous new cedar deck designed for seamless indoor-outdoor living. Complete with a hot tub, outdoor shower, grilling area, and sunny lounging spaces, the private deck overlooks rolling pastoral fields, creating a private outdoor setting equally suited for entertaining, quiet mornings, or evenings spent soaking under the stars.The kitchen pairs clean contemporary lines with stone countertops, custom cabinetry, a walk-in pantry, handcrafted emerald green Zellige tile, and Fisher & Paykel appliances. Bathrooms continue the same elevated approach, featuring marble finishes, Zellige tilework, and spa-like details including heated floors and a heated towel rack. The primary en suite bedroom is a true retreat, complete with a lofted living space overlooking the main open floor plan living area, a double walk-in closet, and tranquil woodland outlooks.The walk-out on grade lower level offers substantial additional living space ready for customization, with architectural plans available for future completion. Anchored by a wood-burning stove, the space could easily accommodate additional bedrooms alongside media, guest, spa, or studio space.Outside, mature trees and wooded landscape, and the year-round creek create a peaceful and immersive setting. A garage with space for three vehicles adds practicality to the property's thoughtful design. Only five minutes from the village of Chatham, the property offers rare privacy and natural beauty without sacrificing access to the region's most beloved towns, restaurants, and cultural destinations. Hudson's celebrated Warren Street, with its restaurants, galleries, boutiques, and Amtrak station, is under twenty minutes away, while the Berkshires' cultural and outdoor destinations, including Great Barrington, Lenox, and Tanglewood, are all within easy reach. New York City is reachable in just over two hours by car or train. Chicory Hill House delivers sophisticated country living with privacy, design, and a high level of finish at every turn.

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$2,140,500
2,908
3bedrooms
2bathrooms

By Annonceur International

Nearby
32
Video

Property Old Chatham (United States)

Escape the hustle of city life and discover Bellavista Country Estate, a grand 12,000-square-foot Georgian brick residence set on over 25 private acres in the foothills of the Berkshires, ideally situated between the Hudson River Valley and the Berkshires. Offering 6 to 9 beautifully appointed bedrooms, including three full suites, five bathrooms, multiple fireplaces, and both a fully stocked eat-in kitchen and a formal dining room, the estate blends elegance and comfort with ease. Recreation and relaxation abound, with a spacious in-ground pool, a serene pond, and direct access to miles of hiking and snowshoeing trails, including those of the Old Chatham Hunt Club. Indoors, guests enjoy a full gym, a game and entertainment room with arcade favorites, a home theater, a library of hundreds of books, and a finished attic, while a 4,500-square-foot barn with foosball, ping pong, and bar space provides additional room for gatherings and events. Perfect for weddings, anniversaries, family celebrations, and private retreats, Bellavista also offers access to private chefs, caterers, and event planning support, with every detail—from fiber-optic internet and full-house generators to weekly pool and grounds maintenance—thoughtfully attended to. Since 2011, the estate has been a successful luxury rental for vacations and retreats, equally suited to private full- or part-time residence, a hybrid work-from-home escape, or an unforgettable destination getaway. Just minutes from Chatham, Hudson, and Kinderhook, and a short drive to Lenox, Stockbridge, and Great Barrington, the estate is surrounded by farm-to-table dining, art galleries, organic markets, and the renowned Crandell Theater, with easy access via the Taconic Parkway or I-87 from New York City, I-90 from Boston, Amtrak to Penn Station, or Albany International Airport.

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$3,595,000
6bedrooms
5bathrooms
land 10.2ha

By William Pitt Sotheby's International Realty

Nearby
50

House with pool Pittsfield (United States)

Experience the perfect balance of grand-scale architecture and tranquil nature in this stunning 6,000+ sq. ft. modern Colonial. Nestled on 3.42 manageable acres within a private enclave near Onota Lake, this 5-bedroom, 5.5-bath estate offers sweeping meadow views just minutes from the world-class arts of Tanglewood and The Clark. The entry is marked by dramatic dry-laid stonework, leading into an interior defined by soaring heights. The heart of the home is a two-story living room featuring vaulted ceilings and a floor-to-ceiling stone fireplace. The expansive living space of the great room flows effortlessly into a gourmet chef's kitchen equipped for high-end entertaining with dual refrigerators, double wall ovens, and a center island cooktop with a built-in griddle. High-top island seating allows for social cooking and a sizable breakfast area flanked by a wall-to-wall credenza—ideal for buffet-style hosting. The home's floor plan thoughtfully blends communal areas with distinct privacy across three levels. The main level is designed for complete convenience and the primary suite is a true sanctuary. It features a private egress to the pool and a hidden back staircase leading to a secluded loft—perfect for a library or reading nook overlooking the suite. The upper level offers a sweeping gallery balcony overlooking the great room, leading to four spacious bedrooms. This includes two private ensuites and two additional bedrooms serviced by a full bath and a dedicated laundry room. The lower level is an entertainment hub featuring a home theater, gaming space, gym, full bath, and a secondary egress for easy garage access. The fully-fenced backyard makes for a resort-style oasis. Host movie nights on the expansive deck, or relax by the heated inground pool and custom-finished patio. The designer firepit is anchored by a unique stone compass inlay, and a poolside full bathroom ensures guests never need to track water through the main house. For the automotive hobbyist or enthusiast, a high-end, three-bay attached garage is professionally finished with epoxy floors, industrial-style metal cabinets, and an EV charger. You will also find a massive, 50x40 detached shop with four bays and oversized doors. Whether for housing a car collection, an RV, or a professional art studio, the possibilities of this space are endless. Embrace the Berkshire landscape in a home where every detail has been considered. Whether you are heading out for fine dining or staying in to enjoy your private oasis, Blythewood Estates offers a lifestyle of unparalleled peace and sophistication.

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$1,199,900
5bedrooms
6bathrooms
land 1.4ha

By William Pitt Sotheby's International Realty

Nearby
Contract pending
44

Farmhouse with pool Austerlitz (United States)

A Classic Modern Farmhouse with Incredible Views - This home has been thoughtfully updated to provide a seamless blend of style and comfort. The property features a resplendent in-ground pool, a spacious swim pond, and a three-car garage with an inviting guest suite above.The main residence welcomes you with a charming wrap-around porch and an enchanting screened porch, both perfect for enjoying the dynamic and ever-changing views. The interior is bright and lively, with each space thoughtfully designed to capture the natural beauty of the surroundings.The gourmet kitchen, a convivial hub with a grand stone fireplace, offers direct access to the screened porch and serves as the perfect backdrop for culinary exploration and social gatherings. The first floor also includes a welcoming foyer, a serene bedroom suite, and an elegant formal living room.Upstairs, the master suite is a haven of sophistication, complete with a stone fireplace and ample space for relaxation. Two additional guest bedrooms share a Jack and Jill bathroom, providing comfort and privacy for friends.The finished lower level is dedicated to leisure and repose, crafted with the ultimate goal of relaxation in mind. Here, in this tranquil setting, you'll find the peace and privacy you desire, all within a home that exudes charm and character.

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$2,790,000
4bedrooms
5bathrooms
land 12.7ha

By William Pitt Sotheby's International Realty

Nearby
50

House Pittsfield (United States)

Set just off the shoreline of Onota Lake and accessed by a private bridge, this approximately 1.25-acre island offers a kind of ownership that is seldom available in the Berkshires. Surrounded by water, the property creates a natural sense of separation and calm, with broad lake views and a level of privacy that is difficult to replicate without sacrificing accessibility. Here, the experience is distinctly your own, yet the mainland is always within easy reach. The existing residence is positioned to take full advantage of the setting. A vaulted living space with a loft above, two fireplaces, and expansive windows and sliders bring in light and water views throughout the day. A covered porch extends directly toward the lake, offering a simple, immediate connection to the outdoors. Nearly every room engages the water in some way, reinforcing the feeling of being fully immersed in the landscape. For many, the true value here lies in the land itself. An island of this scale, with direct access and generous shoreline, presents a rare opportunity to shape a long-term vision in a setting that stands apart from more typical waterfront properties. Centrally positioned within the Berkshires and convenient to the region's cultural and outdoor destinations, the property offers a balance of seclusion and accessibility that is rarely achieved.

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$1,999,000
3bedrooms
3bathrooms
land 5,059

By William Pitt Sotheby's International Realty

Nearby
41

House Pittsfield (United States)

Immaculate, adorable, expansive, well-maintained 2500 sq ft ranch. 4 bedrooms 3 bathrooms, open living room, and dining area with fireplace. Bright eat-in kitchen, a sunny 3-season porch with a newer deck. This home sits on a 1/2-acre lot in a quiet, tucked away neighborhood. There's a full walkout lower level with family room, fireplace, bar, full bathroom, and dining area which leads to a back patio and a nice, open backyard area. Home has lots of storage. New chimney, garage door, and side deck are just some of the upgrades. Close to shopping, downtown, theaters, Lake Onota and schools.

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$469,000
4bedrooms
3bathrooms
land 2,145

By William Pitt Sotheby's International Realty

Nearby
50
Video

Property Lenox (United States)

Just 3 miles from Tanglewood and moments from the heart of Lenox, this 36+ acre estate offers rare scale, privacy, and flexibility in one of the Berkshires' most sought-after settings. A long, tree-lined driveway creates a strong sense of arrival, unfolding into two separate residences surrounded by woods, open land, and long-range possibility. The acreage offers both seclusion and the ability to selectively open views toward October Mountain State Forest. The main residence is thoughtfully configured for multi-generational living. The first floor centers around a large living and dining room anchored by an oversized stone fireplace, an eat-in kitchen with oak cabinetry and granite counters, and multiple access points to the outdoors. A heated sunroom and screened porch extend the living experience across seasons. The primary suite includes an en-suite bath, and this level is further enhanced by a second kitchen and laundry hookups, creating true independence within the home. The second floor functions as its own private level, featuring three bedrooms and two full baths. The guest house feels like a second home entirely. With two bedrooms, two full baths, a dramatic stone fireplace, and a kitchen finished with Caesarstone quartz, it offers independence without compromise. Mini-split systems provide year-round comfort, while a private laundry and generous scale make it equally suited for extended stays or full-time living. Both residences feature claw-foot tubs and roofs replaced within the past three years. A two-car garage at both houses, potting shed, fire pit ring, and expansive grounds complete the offering. This is a property defined by flexibility and scale--where multiple generations can live together while maintaining independence, and where land, light, and structure align to create lasting possibility.

… 
$1,650,000
7bedrooms
7bathrooms
land 14.7ha

By William Pitt Sotheby's International Realty

Nearby
37

Property with garden Lenox (United States)

The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental. The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a strong performer for weddings, corporate retreats, and multi-generational stays. The grounds feature open lawns, established gardens, and west-facing views. Fully ADA compliant and walkable to Lenox's restaurants, shops, and cultural venues. A rare opportunity to own a large-scale, income-producing property in one of the Berkshires' most established locations.

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$4,690,000
13bedrooms
14bathrooms
land 1.2ha

By William Pitt Sotheby's International Realty

Nearby
Contract pending
45

Property with pool Pittsfield (United States)

Charming, move-in ready side hall Colonial, a true ''dollhouse!'' Welcome home to this absolutely stunning, meticulously maintained side hall Colonial nestled in a super quiet, peaceful neighborhood. Combining classic charm with a long list of modern, high-ticket upgrades, this home is the definition of a turnkey property and is ready for its next chapter. Step inside to find a warm and inviting living space featuring a cozy wood-burning fireplace, perfect for chilly evenings. Classic hardwood floors run throughout the home, currently protected by brand new, plush carpeting that offers a fresh feel while preserving the beautiful wood underneath. The beautifully updated kitchen and dining area flow seamlessly together, creating an entertainer's dream space that is sure to please your guests. Through the sliding glass doors off the dining area, you will discover your own private outdoor oasis. The brand new deck overlooks a quiet, beautifully landscaped backyard that offers a peaceful escape from the daily grind. It is the ultimate setup for summer BBQs, morning coffee, and refreshing afternoon dips in the sparkling above-ground pool. The screened porch is another magnificent amenity to cozy up and read in the afternoon or sip cocktails in the evening. Beyond its picture-perfect aesthetic, this home offers incredible peace of mind with major mechanical upgrades designed to last for years to come. The property boasts a durable new metal roof, a high-efficiency wall-hung furnace, and a brand new hot water heater, saving you from any hidden, immediate expenses. From its exceptional curb appeal to its pristine, thoughtful interior, this home is simply a dollhouse that you have to see to believe. Properties this well-maintained do not stay on the market long, so schedule your private tour today before this gem is gone!

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$294,900
3bedrooms
1bathroom
land 567

By William Pitt Sotheby's International Realty

Nearby
50

House with terrace Pittsfield (United States)

Pride of ownership resonates through this distinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut Street near the esteemed Pittsfield Country Club and Upstreet Cultural District, and just minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character, boasting five bedrooms and two and a half baths, thoughtfully improved over the long term owners' commitment to preservation and restoration. This prominent manor style home may be coupled with the neighboring guest house which features 3 bedrooms and 1 bath plus a first floor in-law bedroom suite and a 2 car garage, if one so chooses to accommodate extended family, friends, or caregivers.

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$799,900
5bedrooms
3bathrooms
land 1,335

By William Pitt Sotheby's International Realty

Nearby
Contract pending
42

House Lenox (United States)

Tucked away on 4 acres of wooded and partially cleared land, this lovingly maintained 1960 cape-style home offers the perfect blend of privacy, character, and opportunity. Set back from the road by a long driveway, the property creates a peaceful retreat just minutes from the heart of Lenox and outdoor destinations like October Mountain State Forest and Kennedy Park. Inside, the home is ready for its next chapter with spacious and inviting living areas including a formal living room, dining room, kitchen, and a cozy family room with gas fireplace and slider access to the private backyard. A sunroom off the kitchen is perfect for seasonal enjoyment. The first-floor primary bedroom features a connected full bath with convenient hall access, while upstairs offers two additional bedrooms, an office space, and another full bathroom. A two-car garage located under the home provides direct access to the basement and additional storage or workshop potential. Full of warmth and well cared for through the years, this property is ready for its next owners to reimagine and make it their own.

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$550,000
3bedrooms
2bathrooms
land 1.6ha

By William Pitt Sotheby's International Realty

Nearby
Contract pending
12

House Pittsfield (United States)

Completely renovated in 2021, this thoughtfully updated 2-bedroom, 1-bath home offers easy, low-maintenance living with a fresh, modern feel throughout. With 747 square feet of efficiently designed space, every inch has been maximized for comfort and functionality. The interior features updated finishes, an inviting layout, and abundant natural light, creating a warm and welcoming atmosphere. The kitchen and living areas flow seamlessly, making the home feel open yet cozy--perfect for everyday living or entertaining. Ideally located just minutes from downtown Pittsfield and the vibrant Cultural District, you'll enjoy convenient access to local dining, shopping, arts, and entertainment. Whether you're looking for a primary residence or an investment opportunity, this property offers value and accessibility in a central location.

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$169,900
2bedrooms
1bathroom
land 283

By William Pitt Sotheby's International Realty

Nearby
Contract pending
23

House North Chatham (United States)

Experience the perfect blend of historic settlement and pastoral tranquility, enhanced by the abounding Valatie Kill on the property in the coveted hamlet of North Chatham. This is a rare opportunity to own a home in a nationally recognized Historic District, where 18th-century charm meets the modern desire for space and serenity. This very sweet 3200 square foot 4 bedroom 2.5 bathroom home comes to the market for the first time in nearly 50 years and preserves its colloquial charm throughout. Featuring an eat in kitchen and gracious dining room, it is a wonderful gathering spot. A downstairs primary en suite bedroom is coupled with a living room with fireplace and a seasonal sunroom with a herringbone patterned red brick floor, creating a heart and hearth with plenty of rooms to congregate. Add to the main house a two story barn and a one car garage making this offering a workable home for many folks. North Chatham NY is a close knit community and a collection of perfectly charming 18th and 19th century residences of architectural significance surrounded entirely by equestrian estates and arcadian farmland. Once a trolley stop on the Albany-Hudson line developed in 1795 and conveniently situated between the villages of Kinderhook and Chatham NY and 2.5 hours from NYC, this offering inhabits the essential Upstate farm to table lifestyle with fabulous restaurants and shops nearby. This community is a haven for those seeking a slower pace without sacrificing connectivity.

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$795,000
4bedrooms
3bathrooms
land 6,880

By Four Seasons Sotheby's International Realty

Nearby
Contract pending
12

House Hillsdale (United States)

Rare waterfront opportunity on the Roeliff Jansen Kill / Green River! This prime .58-acre parcel in Hillsdale is the ultimate head-start for your dream home or weekend escape. Save thousands in development, the essential infrastructure is already completely in place, including an existing septic system, well, electric hookup, and a cleared house foundation ready for your vision. Imagine stepping out of your future back door right onto the water's edge. The property also features a detached one-car garage perfect for vehicle parking or secure storage, perennials throughout, and a charming, well-maintained gazebo for relaxing by the river. Located just minutes from Catamount Mountain Resort, Great Barrington, and the heart of Hillsdale, you get the perfect blend of tranquil waterfront living and Berkshire/Hudson Valley convenience.

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$75,000
land 2,347

By William Pitt Sotheby's International Realty

Nearby
23

House Stockbridge (United States)

Light-filled contemporary Cape built in 2020, this Stockbridge home features an open floor plan anchored by a great room with a gourmet kitchen, dining area, and living room. Two spacious first-floor bedrooms share a full bath, while the expansive second-floor primary suite offers a luxurious spa bathroom and a balcony overlooking the living area. The four-season sunroom (heated and cooled for year-round use) opens to the level backyard. Lovely front entrance with Bluestone steps into an ample mudroom. Enjoy year-round comfort with zone-controlled mini-splits. Close to vibrant Great Barrington, Stockbridge, and Lenox. A quick drive to Tanglewood, cultural venues, and abundant outdoor recreation including hiking and lakes, this modern retreat blends style, comfort, and an exceptional Berkshires location.

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$699,000
3bedrooms
2bathrooms
land 4,087

By William Pitt Sotheby's International Realty

Nearby
40

Farmhouse Pittsfield (United States)

Set on an oversized corner lot at the end of a quiet dead-end street, this bright renovated 3-bedroom, 2-bath home offers an impressive amount of outdoor space in a neighborhood setting. The expansive yard is the standout feature, with established gardens, mature trees, a firepit area, open lawn space, and a fenced section for pets. Inside, the home has been thoughtfully updated throughout. The bright eat-in kitchen features new appliances, stylish finishes, and a generous pantry. The main level also includes a living room, first-floor bedroom, full bath, and a three-season porch. Upstairs you'll find two additional bedrooms, a home office, a renovated full bath, and a covered porch overlooking the neighborhood. The lower level provides laundry and storage space, while the detached garage offers additional room for tools, equipment, and seasonal items. The established gardens, firepit, and oversized yard are what make this property special, creating a home that feels welcoming and well-loved.

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$269,900
3bedrooms
2bathrooms
land 1,862

By William Pitt Sotheby's International Realty

Nearby
27

Property Pittsfield (United States)

Located in Southeast Pittsfield, this well-maintained Colonial offers timeless charm, thoughtful updates, and a floor plan that feels just as functional today as it did when it was built. Hardwood floors run throughout the home, and the inviting living room is anchored by a wood-burning fireplace with a bright sunroom just beyond--perfect for a home office, reading nook, or additional living space. The kitchen features granite countertops, cherry cabinetry, stainless steel appliances, and plenty of workspace, while the formal dining room provides the ideal setting for everyday meals or entertaining. Just off the kitchen, a mudroom and full bath create a convenient everyday entrance with direct access to the backyard. Upstairs, you'll find three bedrooms, including a spacious primary bedroom, along with a full bathroom. Step outside to enjoy a deck and patio overlooking the fully fenced backyard, offering a private space to relax, garden, or entertain. Two storage sheds provide plenty of room for tools and outdoor equipment, while the detached two-car garage is a standout feature with epoxy floors and a recently updated driveway. From the beautifully maintained interior to the meticulous outdoor spaces, this is a home where pride of ownership is evident throughout. Move right in and enjoy everything this Southeast Pittsfield neighborhood has to offer.

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$435,000
3bedrooms
2bathrooms
land 567

By William Pitt Sotheby's International Realty

Nearby
50
3D visit

House with pool Lee (United States)

Set on just under an acre along one of Lee's most desirable roads, this beautifully maintained home combines timeless design, quality craftsmanship, and exceptional outdoor living. Overlooking peaceful meadows with stunning sunset views, the setting offers the perfect balance of privacy and natural beauty. Designed for both entertaining and everyday living, the backyard is truly the centerpiece of the property. A tiered bluestone patio creates multiple spaces to gather and relax, featuring a built-in outdoor kitchen, gas fire pit, and a heated saltwater plunge pool by Soake Pools. Mature landscaping, professionally designed landscape lighting, and a charming storage building complete the outdoor space, creating a backyard that feels like your own private retreat. Inside, the home is warm, inviting, and thoughtfully designed. The eat-in kitchen is the heart of the home with a large center island, custom cabinetry, premium JennAir appliances, and direct access to the patio for seamless indoor-outdoor living. Just off the kitchen, the family room offers a comfortable place to unwind, while the formal living and dining rooms provide the perfect setting for holidays and entertaining. A powder room and first-floor laundry add convenience to the main level. Upstairs, the spacious primary suite offers a walk-in closet and a beautifully appointed en-suite bathroom featuring a soaking tub and walk-in shower. Two additional bedrooms share a full bath, while the oversized bonus room provides incredible flexibility. Filled with natural light from a dramatic picture window overlooking the backyard and rolling meadows with distant mountain views, it's the perfect space for a media room, playroom, home office, or fourth bedroom/guest suite. A second staircase offers easy access and enhances the home's thoughtful layout. Additional features include a new roof in 2022, an attached two-car garage and a full basement with radiant heat, providing ample storage and endless potential for future finishing. From the quality craftsmanship and thoughtfully designed floor plan to the incredible outdoor spaces and picturesque setting, this is a home that has been exceptionally cared for and is ready to be enjoyed for years to come.

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$995,000
4bedrooms
3bathrooms
land 3,723

By William Pitt Sotheby's International Realty

Nearby
Contract pending
30

Farmhouse Lenox (United States)

Set just moments from downtown Lenox, this charming New England farmhouse blends classic character with thoughtful modern updates. From the moment you arrive, the home's inviting presence and timeless appeal set the tone for what's inside. The recently renovated kitchen serves as the centerpiece of the home, beautifully designed with quartz countertops and all new appliances--perfectly opened to the dining area to create a seamless and functional space for everyday living and entertaining. A cozy living room is adjacent to the dining room. On the other side of the kitchen, a thoughtfully-designed mudroom and bonus space offers the ideal work-from-home office, complete with a half bathroom, laundry, and direct access to the backyard and patio. Upstairs, you'll find three comfortable bedrooms along with a full bathroom, offering a practical and well-balanced layout. Outside, the fully fenced yard provides a private retreat, enhanced by a newly-installed patio--perfect for gatherings or quiet evenings. A standout feature is the custom treehouse, complete with electricity, creating a truly special space for play or creativity. Additional highlights include a one-car detached garage and close proximity to Lenox's vibrant downtown, known for its shops, dining, and cultural attractions. A rare opportunity to own a move-in ready home that effortlessly combines charm, convenience, and modern living in one of the Berkshires' most desirable locations.

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$495,000
3bedrooms
2bathrooms
land 486

By William Pitt Sotheby's International Realty

Nearby
Contract pending
26

House Pittsfield (United States)

Set on a corner lot in a well-established neighborhood, this home offers a practical layout, thoughtful updates, and plenty of outdoor space. This 2-bedroom, 1.5 bath split-level home features hardwood floors throughout the main living spaces and bedrooms, creating a warm and cohesive feel. The kitchen opens directly into the dining room, offering an easy flow while overlooking the spacious backyard with a laundry and half bathroom right off the side entrance for convenience. The lower level offers excellent potential for partial finishing--ideal for additional living space, a home office, gym, or recreation area. Outside, the large backyard provides ample room for entertaining, gardening, or play, and the detached one-car garage adds convenience and storage. Well-maintained and full of opportunity, this home combines comfort, charm, and future potential in a desirable setting.

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$295,000
2bedrooms
2bathrooms
land 1,174

By William Pitt Sotheby's International Realty

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