luxury houses for sale Monterey, United States

Discover this beautifully maintained home with a long driveway that meanders over the scenic Clam River. The main level boasts an inviting open floor plan, highlighted by a kitchen featuring a full-length window that offers breathtaking views of the treetops. The dining and living areas are enhanced by soaring cathedral ceilings, a striking window wall, and a cozy gas fireplace, creating an ideal space for entertaining and relaxation. This level also includes a convenient half bath, a spacious foyer, and a dedicated office space. Venturing to the lower level, you'll find high ceilings and an abundance of natural light. This space includes a luxurious primary suite with an en suite bathroom, two additional bedrooms, a full bath, a recreational room, and a laundry area, perfect for comfortable living. Step outside to enjoy two decks ideal for outdoor gatherings. The oversized attached two-car garage offers ample attic storage, while a nearby shed provides extra storage solutions. The meticulously landscaped grounds feature impressive rock formations, charming rock walls and paths, vibrant perennial gardens, and a firepit creating a serene outdoor retreat. Enjoy modern conveniences with underground power and fiber optic internet. A mere 20 minutes to downtown Great Barrington known for its fine dining and shopping. Centrally located to all the cultural and natural attractions the Berkshires is noted for. Don't miss the opportunity to make this stunning property your new home!

Nestled in a peaceful corner of the South Berkshires, between Sandisfield and Otis, lies a 4,645 sq ft home with 16 beautiful acres. This 5-bedroom, 4 ½-bath property isn't about opulence; it's about creating a welcoming space for gatherings. Built by the sellers with the intention of hosting frequent guests, this home has been lovingly maintained & thoughtfully designed. Inside, you'll find a range of inviting living spaces. The 4-season sunroom lets you enjoy the changing scenery all year round. The great room, with its high ceilings adjoins the huge eat-in kitchen, the heart of the home, ideal for cooking and sharing meals. The family room, game room, and wet bar provide plenty of options for relaxation and entertainment. Radiant heated floors throughout the home! The property abuts the historic Knox Trail, adding a touch of history to your surroundings. It's incredibly quiet here, offering a serene retreat from the busy world. Living in the Berkshires means embracing a lifestyle rich in natural beauty and cultural experiences. With its rolling hills, scenic trails, and pristine lakes, the region is a haven for outdoor enthusiasts. The Berkshires also boast a vibrant arts scene, with renowned music, theater, and dance performances. The area is dotted with charming towns offering world-class dining, unique shopping experiences, and a strong sense of community. This home is perfect for those who cherish quality time with loved ones and appreciate a well-cared-for space. If you value peaceful surroundings, love hosting gatherings, and are looking for a place where you can build lasting memories, this property could be your ideal home in a serene corner of the of the Berkshires, close to lakes, state forest, the Appalachian Trail and skiing.

This comfortable contemporary four bedroom, two bath home offers privacy yet it is convenient to local restaurants, a town center, and a small winter skiing area. The relatively open floor plan features a sunroom, living room and two screened porch areas. A nice wrap around deck is another treat to be enjoyed along with a fairly spacious back yard. The to be installed four bedroom new septic system will be provided as part of the Closing process. The 1.27 acre lot falls within the towns of Sandisfield and Otis.

For the first time in over a century, this cherished New England farmhouse, lovingly maintained by the same family, is now available. Steeped in history, the home retains many original features that evoke a timeless charm and offer a warm, inviting atmosphere. The spacious living room flows effortlessly onto a serene rear deck, perfect for relaxation. Just beyond the backyard's brush lies the tranquil Hayden Pond, ideal for kayaking and canoeing. Nestled only minutes from downtown Otis, this property is conveniently close to local dining, shopping, Otis Ski Ridge, Jacobs Pillow, and all the best the Berkshires have to offer.

Tyringham is arguably the most beautiful place in the Berkshires. The majestic east-west valley has retained its historic character, with antique homes nestled among rolling farm fields and gently sloping hills. Just off Main Rd, on a quiet lane known as Church Road, sits the NorthRUP/ROP-Wilson House. Built in the late 1700s in the Georgian-Federal period, the home underwent a Greek Revival update in the 1830s, giving it a grander, yet timeless appeal. Having had few owners, the home has fortunately retained its original detail and character. Nestled in the middle of the valley, with views of the old school house and hillside cemetery, time seems to stand still here. Imagine the stories told around the grand fireplace, the family dinners, and the generations that have called this place home. A short stroll out the front door is wonderful Tyringham Cobble, miles of hiking trails and views. The first floor features a spacious eat-in kitchen that opens to a stone patio perfect for outdoor lounging and firefly spotting. Gather in the formal dining room for dinner with friends, below a vintage metal chandelier. A wide central hall with powder room separates the kitchen and dining areas from two additional living spaces. The Green Room offers stunning views of Church Rd, while the Yellow Room boasts a grand fireplace. Upstairs, one finds four more bedrooms - two with picturesque valley views - and a full bathroom. Pass through the Yellow Room to another grand room with a fireplace, an adjoining back room, and an upstairs area with two more rooms perfect for extra space during the summer or perhaps an artist studio. This home is truly for the antique lover - preserve the home's original charm or elevate it to new heights. The house is in good mechanical and structural condition. The rear of the home would require updated HVAC and electric to become four-season living space. Only 5 minutes to grocery shopping, 7-14 min to the great eating scenes in Lenox and Lee, and less than 20 min to downtown Great Barrington.

1790 Colonial restored for 2024 living. Located on the well loved Konkapot River and on a quiet country road this home has been completely revamped to today's standards. Large recently expanded living room with fireplace, plus large windows to views of Beartown Mountain. First floor primary suite with private sitting room with fireplace. Gracious formal dining room with adjacent Butler's Pantry. Spacious eat-in kitchen. Library also on the main floor. The second floor has four bedrooms, two baths plus spaces for additional offices. The property includes a fenced pool, patio and garage. As an extra bonus there is an additional lot at Lake Buel with a storage Garage and access to a private entry to the lake.

4-Bedroom Becket House on 2 Acres with Stunning Private Views and Sunrises. Discover your dream home in Berkshires Becket! This beautiful 4-bedroom house is set on 2 acres of land, offering breathtaking private views and awe-inspiring sunrises. The main floor features a brand new bathroom, a convenient laundry room, and a spacious bedroom. The kitchen is open to the great room and is equipped with a dishwasher, perfect for easy meal prep and clean-up. The highlight of the main floor is the huge great room with cathedral ceilings, creating a sense of grandeur and space with glass doors leading out to the deck and views. Upstairs, the primary bedroom offers a full bath, a cedar closet, and a balcony overlooking the great room. This serene retreat is perfect for relaxation and privacy. The lower level has two more bedrooms and a large utility room with extra space for storage. Stay comfortable year-round with the new HVAC system on both the main floor and lower level.

On the crest of Woodruff Mountain, moments from The Southfield Store, York Lake, and area amenities, a classic country estate awaits. Its centerpiece is a stately 5BR, 5000sf, c. 1798, Georgian-Federal home, set on a 232-acre property encompassing a 3,550sf historic barn, smaller barns & run-ins, gardens & green house, Gunite pool & pool house, tennis court, fields, pastures, stream, mile-long trail abutting Sandisfield State Forest, and 5-acre spring-fed pond, all arranged for maximum livability and delight. You'll be pleased with the elevator, generator, & other mod cons, and charmed by historic details, stunning vistas, & untrammeled view of the star-studded night sky. Not enough? A 6,000sf guest house with four apartments suggests myriad uses for guests or income. Perfectly beautiful. The origins of East Hill Farm date to the 1740s, when New Marlborough was first settled, and Thomas Shepard came from Cambridge, Massachusetts, to establishe a home in Southfield. In 1798, he built a grander residence signifying his prosperity and stature in the community. Shepard's new home boasted a facade and interior details in the latest neoclassical style, eight rooms including four bedrooms, five fireplaces, and expansive views across pasture and fields to the south. Now on the market for the first time in 55 years, East Hill Farm awaits a new steward to write a new chapter in its rich history. Throughout its 226-years, the now 232-acre property has been enhanced and adapted to meet the needs and wishes of many generations. The property's new owner will benefit from a classic vision of what a gracious country home should be, with tennis court, Gunite swimming pool, pool house, green house, spring-fed pond and streams, historic three-story barn, two smaller barns, woodlands and trails, perennial gardens, pastures, run-in sheds, and an expansive guest house with four apartments and totaling nine bedrooms. A three-bedroom caretaker's house, set on five acres, though not part of this listing, is being offered separately to the buyer of East Hill Farm. Classic, too, is the landscape design: gardens near the house lead the eye to pasture, hedgerow, and pond, and, beyond that, to a distant west view. Sight lines are punctuated by towering sugar maples, stone walls. The property abuts both Sandisfield State Forest and New Marlborough Land Trust acreage, connecting the two. About 2.5 hours drive from New York and Boston and 60 minutes from Bradley International Airport, East Hill Farm offers privacy as well as unparalleled access to culinary, recreational, and cultural amenities, including Sandisfield State Forest, York Lake, 1,000-acre Pond, Southfield Store, Old Inn on the Green, Butternut ski resort, and Great Barrington's shops, restaurants, and performance venues. Tanglewood, five Equity theaters, Jacob's Pillow Dance Festival, and amenities in northwest Connecticut are within easy reach. New Marlborough is a low-tax town of artists, writers, craftspeople, and second-home owners, attracted by its laid-back, sophisticated rural atmosphere. Its meeting house is the venue for the Music & More series and exhibits by painters, sculptors, ceramicists, and photographers, while its village green is the setting for a vibrant Saturday morning farmers' market. The Thomas Shepard House Listed in the National Register of Historic Places, the Thomas Shepard House was built by Connecticut housewright John Collar who did many homes in the southern Berkshires; one of his design trademarks was the creation of passages and closets next to the chimneys between rooms. In 1798, the Georgian architectural style was transitioning into the lighter, brighter Federal fashion; for instance, the home's fireplace surrounds feature both Georgian bolection moldings and Federal mantels. One unique detail is its enclosed staircase, which is thought to be original and reflect an early use of the house as a meeting place for a progressive Christian community. Subsequent owners have honored the home's original features: millwork and chair rails, chimney cupboards, hardware, wide-board flooring with original T-nails, the dining room's cooking fireplace with oversized beehive oven, and 12-over-12 window sash crafted of dense, durable first-growth wood, containing hand-blown 18th-century glass, and fitted with storms for maximum R-value. Subsequent owners have also added features for comfortable modern living. In the 1930s, a rear ell was added. The sellers enlarged this, bringing the home's size to an estimated 5,000sf and allowing for radiant heat, modernized kitchen, five bathrooms, large mudroom with laundry, family room with kitchenette and full bath, four-car garage, plus a second-floor sunroom, library, and additional bedroom. An elevator connects the library to the family room, a generator keeps things running whatever the weather, and the basement incorporates a wine cellar. The home's cedar shake roof was put on in 2021, there is high-speed Internet, a security system, a drilled well, and the heating fuel is oil. The National Register report is available upon request. Lifestyle Amenities On the north side of East Hill Road, the current owners created a tennis court, 20'x40' Gunite swimming pool, pool house, greenhouse, and 1,960sf barn. Behind it, a mile-long woodland loop road connects the main compound with the guest house to the east and pond to the west. Just west of the home's roofed flagstone patio and ancient apple tree, parterre gardens brim with perennials, annuals, and herbs, blueberry bushes, irises, peonies, and heritage roses. A picturesque 280sf garden shed provides a sweet focal point there, while a broad, mowed path leads to a stone wall and rustic gate, pasture, large spring-fed pond, estimated to be five acres in size for boating, fishing, and swimming. On the road's south side are pastures and woodlands, a stream with charming footbridge, and two barns. The current owners brought in a three-story, 3,550sf, 18th-century barn, dismantled in Vermont and reconstructed on site; this contains a number of large bays and two work rooms. They also built a smaller barn near the stream. Each of the pastures has a water source. In addition, there are two run-in sheds with electricity and running water, and three utility sheds. A portion of the property is in Massachusetts Chapter 61A, which provides for reduced taxes on agricultural properties. The Guest House The guest house is a 6,000sf structure, built in the 1930s as a barn for Arabian horses. Reimagined circa 1990, it contains four duplex apartments, each with radiant heat, independent exterior entrance, living/dining room with fireplace and cathedral ceiling, workable kitchen, first- and second-floor baths, generous closet space, and garage and storage space. It has a new oil/wood furnace, a fire security system, and a shared laundry room off the hallway that connects the apartments to the garage. Apartment 1: Spacious first-floor living/dining room with fireplace and French doors opening to a large, private terrace, den with built-ins, full bath; kitchen, and gracious good-morning staircase leading to the upper floor, which has three bedrooms with one en suite and one shared bath. Apartment 2: Spacious first-floor living/dining room with fireplace and doors onto a large, private terrace, den with built-ins, half bath, and kitchen, and staircase leading to two bedrooms with shared bath. Apartment 3: Spacious first-floor living/dining room with fireplace and French doors to the lawn, den with built-ins, kitchen, half bath, and staircase leading to the two bedrooms and shared bath on the second floor. Apartment 4: Spacious first-floor living/dining room with fireplace and built-ins, den with built in shelving, full bath with claw-foot tub, kitchen, and staircase to two bedrooms and shared bath on the second floor.

Discover waterfront living in this stunning contemporary residence, boasting an idyllic setting with direct lake access. Step inside to find an open-concept main level, where the kitchen, dining room and family room converge into an entertainer's dream. There is an additional family room with a wood burning fireplace on the main level. Transition effortlessly to the outdoors where the expansive lake view deck awaits. A hot tub offers a private oasis to unwind under the stars, framed by the tranquil sounds of the water's edge. Ascend to the second level where the primary bedroom serves as a personal retreat, complete with an ensuite bath designed for pampering. Two additional bedrooms offer comfort for family and guests, while a versatile bonus room provides space for your lifestyle needs.

Discover your dream home in the desirable Becket Woods community! This stunning, recently renovated property offers three spacious levels of living, featuring abundant natural light from skylights and impressive vaulted ceilings. Enjoy cozy evenings by the fireplace in the living room or unwind in the generous first-floor primary suite with ensuite bathroom and soaking tub. With over 3,700 square feet of stylish contemporary design, the open layout seamlessly connects the living, kitchen, & dining areas. Lots of sleeping spaces with 4 bedrooms plus bonus rooms that include a loft and 3.5 bathrooms, enough space for everyone. The finished lower level adds an extra 821 square feet perfect for family fun and currently furnished with a cozy sectional, television and ping pong table. Step outside to your private oasis on over 5 acres, with an inviting inground swimming pool and a deck outfitted with a hot tub. Sit around your Adirondack chairs with friends and roast a marshmallow on your solo stove. Enjoy amenities that include tennis courts, pickleball courts, a basketball court, a swimming pond, and hiking trails within the community: all this just 15 minutes from downtown Lee and 24 minutes from Lenox. This house is offered fully furnished. Don't miss this ideal vacation getaway!

Discover the perfect blend of contemporary style and natural beauty in this newly renovated riverfront home. With 1,600 square feet of living space, this residence features three bedrooms and two brand-new bathrooms. The hip, newly renovated kitchen is a true design statement and now opens to the great room, with its high ceilings and large windows that fill the space with natural light. The kitchen's Classic Retro appliances, including a 24'' gas range with convection oven and an energy-efficient refrigerator with LED lighting, add a touch of iconic nostalgia with modern functionality. White quartz countertops complete the sleek look. This riverfront retreat reimagines modern living with style and serenity. The great room's wood-burning fireplace, and the home's new high-efficiency hot water hydronic heating system ensures cozy winters, while mini-split air source heat pumps keep things cool in summer. The newly finished lower level offers a versatile walk-out family room, and an additional living area. The new baths include a walk-in shower on the first floor and a soaking tub on the second. Outside, the property features 136 feet of Clam River frontage, with the option to expand to 500 feet with the purchase of additional land. The 1.26-acre lot includes open lawn, a deck for outdoor relaxation or entertaining, and direct river access for summer fun. Located in peaceful Sandisfield, MA, this home is near cultural amenities like Jacob's Pillow and Tanglewood, offering both tranquility and convenience. An abundance of hiking trails, state forests, lakes and rivers are throughout Sandisfield and its neighboring towns.

This quintessential country property is what everyone wants. Located in the Southern Berkshires close to the towns of Great Barrington, New Marlborough and Southfield and Norfolk, CT. This sleek historic and beautifully restored home is conveniently located for skiing, hiking, arts and culture, restaurants and all other Berkshire offerings. This home is beautifully restored and includes a stunning 'party ' barn, and separate garage/storage shed. The house glows, filled with light and sun. A large living room with fireplace and several seating areas has views to fields and flowers. A cook's kitchen with a counter-height fireplace looks out onto a stone patio with fire pit. The library, tv/ media room and powder room complete the 1st floor. Four.bedrooms, 2.5 baths. Restored barn.

Welcome to the highly sought-after Leisure Lee community, where the idyllic beauty of nature meets the comforts of modern living. Situated amidst the serene landscapes of the Berkshires, this community offers an unparalleled lifestyle enriched by the pristine waters of Goose Pond. Residents of Leisure Lee enjoy exclusive access to a private beach on Goose Pond, a 225-acre mountain lake divided in two, lower and upper Goose Pond, renowned for its refreshing cool waters and stunning clarity. Boating enthusiasts will delight in the opportunity to explore one of the finest lakes in the Berkshires, perfect for sailing, kayaking, or simply soaking up the sun on the tranquil waters. This contemporary ranch-style home comes fully furnished and offers three bedrooms and two full bathrooms, providing ample space for relaxation and entertaining. The open floor plan seamlessly integrates the kitchen, living, and dining areas, creating a warm and inviting atmosphere for gatherings with friends. A wood fireplace adds a touch of coziness, perfect for enjoying intimate winter evenings by the fire. The main bedroom boasts its own full bathroom, while two additional bedrooms share a bath, ensuring comfort and convenience for residents and guests alike. Outside, a spacious wrap-around deck offers the perfect spot for al fresco dining or simply taking in the beauty of the surrounding landscape. With just a short stroll to the lake or tennis courts, residents can easily embrace the recreational opportunities offered within this private community. Leisure Lee comprises 85 homes spread across 265 acres of picturesque hills and mature pines, providing a tranquil retreat from the hustle and bustle of everyday life. Conveniently located close to the center of Lee and just a 12-minute drive to the town of Lenox and Tanglewwod, this property offers both seclusion and accessibility to nearby amenities and attractions. Owning a property in Leisure Lee presents a rare opportunity to experience the quintessential Berkshires lifestyle, combining natural beauty, recreational amenities, and modern comforts in a serene and welcoming community setting.

Custom built salt box home situated at the end of town dirt road on 32 acres. Bear Town State forest abuts the property. Heated Inground pool, stunning views of Monument Mountain, established landscaping including apple orchard. Main house with living room, library, dining room eat in kitchen, laundry, powder room, screen porch, access to oversized two car garage. Second floor with 4 bedrooms, 2 baths, large primary bedroom with views, third floor with two additional bedrooms and full bath. Lower level is finished with space for gym, screening room, pool table.. New oil-fired boiler and HWH. Free standing 3 bedroom caretakers house with additional 2 bedroom apartment. A little piece of heaven! Minutes to Great Barrington and Stockbridge. If you seek privacy .....we have it here!

Breathtaking Views from this Stylish and Pristine Home! A home can be a sanctuary, a retreat, and even a source of inspiration. Such is the case at 20 Brewer Hill. Perched atop a small knoll in beloved New Marlborough, with sweeping southerly views into Connecticut, 20 Brewer Hill exudes positivity and warmth. Sitting on the front porch, one can track the ever-changing horizon as the sun moves from dawn to dusk. Morning mist, rainbows, and pink skies are not uncommon. The grounds extend over three acres, with show-stopping perennial gardens, a meandering paved driveway, and a mix of lawn and meadow. The views continue as you step inside, from the updated eat-in kitchen, dining room, light-filled office, and spacious primary suite with renovated en-suite bathroom. Enjoy winter coziness by the living room's gas stove, and summer evenings from the pretty stone patio. Three guest bedrooms and a full bath offer ample guest quarters. This home is in truly pristine condition. Thoughtfully remodeled and meticulously kept, with major improvements made inside and out by the current owners over the past seven years. Amenities include a laundry room, pantry, attached two car garage, mudroom, full basement with storage space, whole house generator, and solar panels that provide a low energy bill and transferable power credits. Located only 2.25 hours from NYC, 2.5 hours from Boston, and 20 minutes from bustling Great Barrington, 20 Brewer Hill is ideally situated in beautiful emerald-green New Marlborough. Just far enough from the busier thoroughfares and crowds, but short drives to the area's many natural and cultural attractions.

Escape to the serene countryside, where this stunning New England farmhouse beckons with its picturesque setting on 10 acres. This property boasts a pool, pool house, garage and barn, offering endless possibilities for enjoyment and relaxation. Step inside this beautifully renovated home (2017), where modern amenities blend seamlessly with classic charm. The 4 bedrooms and 3.5 baths provide ample space for comfortable living. This home is sure to impress with its impeccable design and attention to detail. Outdoor living is a true delight at this property, with plenty of space to roam and explore. The in-ground pool is a refreshing spot to cool off, while the pool house provides a convenient place to relax and unwind. Garage and barn offer storage space for all of your outdoor essentials

Discover the charm of yesteryear with this enchanting 6-bedroom, 2-bathroom antique home nestled in the vibrant town of Lee. Accompanied by a large two-story stone barn, this residence offers a blend of historical elegance and modern potential. Original features such as wood floors, Dutch door, and classic stairway railing are complemented by a dining room with beamed ceilings, built-in china cabinets, and bay window with marble seat. Stained glass windows and pocket doors add to the home's unique character, while a marble fireplace graces the front parlor. The sizeable retro kitchen, complete with Geneva cabinets, awaits your personal touch. Set on a corner lot with mature plantings, the property boasts a private, quiet backyard. The property acts as a warm welcome to the picturesque and culturally vibrant Berkshires region. Call today for your private showing!

Stunning lakefront retreat on serene Center Pond. With an open floor plan, soaring cathedral ceilings, and rich hardwood floors, this home exudes warmth and charm. The living area features a cozy wood-burning fireplace and breathtaking lake views. Enjoy two main-level bedrooms and a full bath, plus a luxurious primary suite on the 2nd floor with landing and water vistas. The finished lower level offers additional living space, perfect for a game room or hangout space. A wrap-around deck and screened porch provide cozy spots to unwind. Just a 30-second walk to the association beach and town lifeguard-staffed beach. It borders town land that can't be built on, ensuring privacy. The best of lakeside living-your own sanctuary close to Jacob's Pillow, Tanglewood and Berkshire attractions. A must see!