luxury real estate for sale Chester, United States

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!

This fully furnished private contemporary home is beautifully maintained and is being sold with an additional 4.14-acre adjacent lot. It's nestled in Becket Estates and features three bedrooms, two bathrooms, and an open-concept design, making it perfect for year-round living or a peaceful retreat. The large wrap-around deck is ideal for entertaining, while the finished 3-season porch offers a serene spot for quiet relaxation. The home boasts ample natural light and beautiful views from its large windows. Additionally, residents can enjoy nature by taking a stroll around the private community ponds. The property is conveniently located only a mile from Jacobs Pillow Performing Arts and just 30 minutes from Tanglewood, with easy access to Rte 20, 8, or 90. Private cul-de-sac!

Discover this exceptional opportunity to own a piece of buildable land nestled amidst breathtaking vistas. This exquisite parcel of over 9 acres of land captivates with its awe-inspiring and panoramic views in every direction offering an unrivaled canvas for creating your dream home, investment property, or architectural masterpiece. This extraordinary canvas presents the perfect platform for your vision to unfold embracing a lifestyle of serenity and elegance.Close to all the Berkshire attractions yet peaceful. Architectural plans have been created, or design your own home. Already has a good perc, approved septic designs, electric, and telephone service available, so embark on a journey of boundless inspiration and create an exquisite haven on this captivating parcel of land.

Country Elegance Meets Historic Charm on 69 Acres! This meticulously reconstructed antique residence, designed by a local architect, blends rustic sophistication with historic allure. The home features a chef's kitchen with granite countertops, Wolf appliances, and a Sub-Zero refrigerator. Original wide pine floors in the historic section seamlessly match the new additions. Equestrian enthusiasts will love the USDF regulation dressage arena, grazing pastures, and a thoughtfully designed horse barn with a heated wash stall, tack room, and a hay loft for over 800 bales. Additional amenities include a detached equipment workshop. Located moments from Route 9, this property offers access to the Berkshires' cultural attractions to the west and Northampton's academic hub to the east.

Welcome to the opportunity of owning an almost 5.5 acres building lot, nestled at the end of a serene cul-de-sac in Peru, MA waiting for your dream home. Owned for over 50 years, it's a piece of Berkshire Country escape now available for the first time. The southern and western property lines are adorned with old stone walls, adding character and charm to your future abode. The land gently slopes upwards, revealing a delightful mix of evergreens and deciduous forest. With hundreds of acres of adjacent stateland, explore the beauty of nature right at your doorstep. Imagine the possibilities for outdoor activities and a lifestyle of tranquility. Just 5 minutes from the picturesque Lake Ashmere, rated one of the most beautiful lakes in Massachusetts and Camp Danbee, a short 10-minute drive to Hinsdale, convenience meets nature seamlessly. Plus, only 12 miles from downtown Pittsfield, you'll have the best of both worlds: serenity and city life.

THIS is the contemporary home on the water that you have been looking for! This hip 3-bedroom, 2-bath gem on Long Bow Lake offers the perfect blend of modern living and natural beauty. As you step inside, wood floors and an airy open layout greet you, with sliders and expansive windows framing breathtaking all season lake views. The open living, kitchen, and dining areas create an inviting space for entertaining, while a cozy wood-burning fireplace promises warmth on chilly winter nights. There are two spacious bedrooms and a full bath on the main floor and the second floor boasts a large primary bedroom with an en-suite bath. Need extra space? An open loft awaits for game nights or a cozy reading nook. The lower level is partially finished, set up as a game room with a separate laundry room. The large storage room provides ample space for firewood, holiday decor and all your extra things. Outside, enjoy a fantastic flat yard, perfect for lounging by the water in your Adirondack chairs while roasting marshmallows by the solo stove. The large wrap around deck is the ultimate set up for outdoor dining and lounging during the warmer months. With a private dock for kayaking and canoeing, this home offers beautiful views year-round and fantastic rental income potential. Fully furnished and ready for you to move in, don't miss your chance to make this waterfront paradise your own!

Begin your Berkshire story here! If you've ever wanted to build your own home this is the perfect spot. Jacobs Hollow is a small, private community with larger lots and close to Jacobs Pillow Dance Center. The town of Lee, Lenox, Otis Reservoir, skiing and the best of the Berkshires recreation and culture are all within a short drive.

Classic elegance and charm, timeless Brick, Mountain Views. Revel in privacy with stunning views all the way to Mt.Snow from the expansive decks, perfect for relaxation and entertaining. The sunlit living room with a fireplace flows into an office space with deck access with mature landscaping and beautiful birch trees. The first-floor owner's suite is a retreat, featuring a jacuzzi, walk-in closet, and a double-sided fireplace. Enjoy the additional deck off of the kitchen for those quiet moments among the trees. The home boasts of a formal dining room and a spectacular grand family room with cathedral ceilings. This property is more than a home; it's a statement of luxury and tranquility, all within reach of the cultural vibrancy of Northampton and the esteemed Seven Colleges. Come See!

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.

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.

Executive colonial sited on over 1.3 acres bordering 17 acres of conservation lands. Hike off your property on Parsons Brook Conservation area or relax in your professionally landscaped backyard with fire pit, waterfalls, 35/70 yd tee boxes w/ synthetic putting greens and 18x36 inground saltwater pool and pool house w/ kitchen. The expansive main residence offers a balance between open concept entertaining, yet offering quiet, cozy areas when needed. Bonus spaces include a 4-season sunroom, home gym, media room and for the ultimate in game day gatherings, the third floor has an expansive entertainment room with custom 8-person wet bar, three tv's, and pool table. High level technology with Solar, 17kw backup generator, 52 speakers in/out Sonos system and whole property security system

Build your own unique Berkshire dream home in one of the most desirable communities in Berkshire county. Enjoy all that Otis Woodlands has to offer all within a stroll or short drive: a private lake, exquisite clubhouse, a pool and two tennis courts. And just beyond OWL enjoy one of the largest recreational lakes in Mass, Otis Reservoir as well as gorgeous Big Pond lake.Otis Ski Ridge is minutes away as is Jacobs Pillow Dance Center along with miles of hiking trails that abound throughout Berkshire county. The property Includes two contiguous lots in Otis and Sandisfield (.73 acres in Otis and .33 acres in Sandisfield) for a total of 1.06 acres. BUYER PAYS A ONE-TIME BUY IN FEE TO OWL 0F $4,000

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.

Welcome to the highly coveted Leisure Lee community! For the first time in half a century, this rare opportunity presents itself to become part of this exclusive enclave. Nestled within the serene landscapes of the Berkshires, Leisure Lee offers its residents a lifestyle of unparalleled tranquility & leisure. At the heart of this community lies Goose Pond, a pristine 225-acre mountain lake renowned for its cool, crystal-clear waters. Residents have exclusive access to a private beach, providing the perfect setting for swimming, sunbathing, or simply unwinding amidst the natural beauty of the surroundings. Boating enthusiasts will delight in the opportunity to explore the vast expanse of Goose Pond, regarded as one of the finest lakes in the Berkshires for water-based recreation. Whether it's sailing, kayaking, or paddleboarding, there's no shortage of ways to immerse oneself in the splendor of the lake. Additionally members can indulge in a friendly game of tennis on the community's courts, all just moments away from the comfort of your new home. Situated on a gently sloping 2.4-acre lot, this property offers seasonal views amidst lightly wooded surroundings, providing both convenience and a connection to nature. Leisure Lee comprises 85 homes spread across 265 acres of picturesque hills and mature pine forests, ensuring a sense of exclusivity and serenity for all who call it home. In summary, Leisure Lee represents more than just a place to live; it embodies a lifestyle of relaxation, recreation, and natural beauty all within minutes to downtown Lee and Lenox. With its idyllic setting, private amenities, and close-knit community atmosphere, this is an opportunity not to be missed for those seeking the quintessential Berkshires experience.

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.

Situated on sought-after Mountain Drive, one of the most desirable streets in Pittsfield, this expansive cape is ready for you to move right in just in time for the Holidays! Enter through the dreamy front porch addition which adds curb appeal and practicality perfect for enjoying a morning cup of coffee or entertaining with evening cocktails. The first floor includes a large living room with gorgeous built-ins surrounding the wood burning fireplace; a formal dining room; remodeled kitchen; full bathroom; spacious bedroom; laundry space and den with a gas fireplace and slider to the deck and backyard. Off the dining room includes a heated sunroom overlooking the private backyard which backs up to Sackett Brook. The second floor includes a large primary bedroom with a walk-in closet, a second spacious bedroom and a renovated bathroom. The lower level features a heated family/game room and workout area as well as a great unfinished work/storage space. A two-car garage, custom made storage shed, new roof, and new hot water heater finish this spectacular home.

Situated on one of the finest lots on the street, offering backyard privacy and distant mountain views, is this thoughtfully renovated Colonial-style home with an in-law suite. From the properties landscape and pool to the in-law suite addition, this owner has thought through every detail updating and making a more sustainable home for someone to enjoy for many years to come! The first floor of this center hall colonial includes a formal living room; formal dining room; eat-in kitchen with breakfast nook; and cozy den with new wood floors and slider to the screened porch. Off the kitchen, a new mudroom expansion with a laundry room connects to the in-law suite addition. The in-law suite with expansive views of the backyard boasts a large vaulted open room with a walk-in closet, full bathroom, radiant heated floors and mini-split air conditioning. The second floor features a large primary suite with walk-in closet and renovated bathroom with soaking tub and separate glass shower. Finishing out the second floor are three spacious bedrooms and a full bathroom. The lower-level accessible through the house or the garage, has been recently remodeled with a full bathroom added. Ample storage and space allows for a family room and separate storage/work space. Outside, an inground salt water pool is surrounded by sustainable landscaping perfect for pollinators and bird watching. Recent updates on this 5-bedroom, 5 bathroom home include a new roof and windows (2021), in-law addition (2022), heating system (2022), exterior painted (2022), screen porch addition (2022), owned solar system (2023), pool salt water filtration system (2023), A/C split system (2024), remodeled basement with full bathroom (2023), and new garage doors (2022). Do not miss out on this spectacular home!

This Mid Century brick home on almost an acre has been completely renovated and updated top to bottom less than two years ago. The renovation includes replacement of roof, plumbing, electrical wiring and panel, windows, insulation, drywall, paint, flooring, kitchen, bathrooms, appliances, boiler and hot water heater, making this a truly turn key home.Step into this fresh,bright home w/4 bedrooms, two baths, open plan kitchen/living room and large family room. An expansive rear deck, impressively large and private back yard and oversized two car garage complete this beautiful move in ready property. If you need more living space, the large, dry, partially finished basement awaits your vision. Schedule your showing now.

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.