The 30 Best Massachusetts luxury properties in Lenox, Massachusetts

Lenox Schoolhouse Apartments is a historic and charming residential community located at 109 Housatonic Street in Lenox, Massachusetts. Housed in a beautifully restored schoolhouse building, this unique property offers modern amenities while preserving its original character. The apartments feature spacious layouts, high ceilings, and large windows that allow for plenty of natural light. Residents can enjoy the convenience of on-site laundry facilities, a fitness center, and a community room. The location is ideal, with easy access to shopping, dining, and cultural attractions in Lenox. Experience a blend of history and modern living at Lenox Schoolhouse Apartments.

Welcome to Alexis J. Prisendorf | Find Berkshire Properties Today With Berkshire County's Best Realtor, located at 271 Main Street, Great Barrington, Massachusetts. With over three decades of expertise in customer service and marketing, Alexis J. Prisendorf stands as a beacon of reliability and excellence in the Berkshire County real estate market. Whether you're seeking your dream home or planning to sell your property, Alexis offers unparalleled service and insight. Explore stunning properties like 26 Pine Crest Hill Road in Egremont, a luxurious 4-bedroom estate set on 4.3 acres, or the sophisticated 165 Kemble Street in Lenox, a refined 1-bedroom residence at Canyon Ranch Living. Discover the charm of North Egremont with the beautifully maintained home at 11 Hickory Hill Road, offering 3 bedrooms and 3 baths on 3.3 acres.

Welcome to ValleyHead Property Gallery, your premier real estate agency located in the heart of the Berkshires at 79 Reservoir Road, Lenox, Massachusetts. At ValleyHead, we pride ourselves on providing personalized and professional real estate services to the Lenox community and beyond. Whether you’re looking to buy, sell, or invest in property, our dedicated team of experienced realtors is here to guide you through every step of the process. Our extensive knowledge of the local market, coupled with our commitment to client satisfaction, ensures that you receive the best possible service tailored to your unique needs. At ValleyHead Property Gallery, we offer a diverse portfolio of properties, from charming homes and luxurious estates to scenic land and commercial spaces. Our mission is to help you find the perfect property that meets your lifestyle and investment goals.

Welcome to Jennifer Capala, William Pitt Sotheby's International Realty in Lenox, Massachusetts! Located at 34 Church Street, our office is your gateway to exceptional real estate services in the Berkshires and beyond. With over 15 years of experience, Jennifer Capala stands out for her unwavering commitment to superior professional standards and her creative approach to overcoming challenges. Her clients describe her as enthusiastic, knowledgeable, responsive, ethical, and extremely helpful. Jennifer's passion for real estate ignited over 20 years ago when she transformed a Brooklyn firehouse into a livable, multi-use space, earning features in New York Magazine and The NY Times. Her background as a commercial photographer in New York City, documenting architecture and interiors, has honed her ability to assess the true potential of any property with a keen eye for design and construction.

Stonover Farm is a charming lodging institution located at 169 Under Mountain Road in Lenox, Massachusetts, United States. Surrounded by picturesque countryside, this tranquil farm offers a peaceful retreat for guests looking to escape the hustle and bustle of city life. The property features beautifully appointed rooms, a cozy fireplace, and stunning views of the rolling hills. Guests can enjoy a relaxing stay in this idyllic setting, with opportunities for hiking, biking, and exploring the nearby attractions. Whether you're seeking a romantic getaway or a peaceful weekend retreat, Stonover Farm provides a warm and welcoming atmosphere for a memorable stay.

The Kemble Berkshires is a historic lodging institution located at 2 Kemble Street in Lenox, Massachusetts, United States. Originally built in the 1880s for a U.S. Secretary of State and New Jersey State Senator, the property has been newly renovated by Shared Estates with modern finishes and luxurious amenities. The estate features manicured landscaping with stunning views of the Stockbridge Bowl. Guests can enjoy various spaces within the property, including a library room, music room, private bar, and seven fireplaces. The Kemble is 100% carbon neutral and can accommodate events for up to 175 guests. The property offers a dining room, professional kitchen, herb and vegetable garden, fire pit, and multi-level stone patios and decks. Guests can enjoy a wide range of amenities, including a virtual reality gaming room, retro arcade, outdoor sports equipment, and more. The Kemble Berkshires is owned by 143 investors through Shared Estates' equity crowdfunding model, making it a unique social equity vehicle in the real estate industry.

Located at 91 Walker Street in Lenox, Massachusetts, the Hampton Terrace Inn is a historic bed and breakfast that has been rated the #1 place to stay in Lenox on Tripadvisor. Originally built in 1897, this inn was once owned by some of the wealthiest families in the country and was among the first of the "Berkshire cottages" to welcome guests. Today, the inn offers romantic cottages and suites that have been updated with modern amenities while still preserving the property's rich history. Just a 5-minute walk from downtown Lenox, Hampton Terrace Inn is the perfect location for a Berkshires getaway. Guests can enjoy private baths, air conditioning, HDTVs, free Wi-Fi, complimentary cognac and liqueurs, and a full breakfast buffet included in their room rate. The inn also features a heated pool, jetted tubs, and fireplaces for guests to relax and unwind after a day of exploring the Berkshires.

The Ponds at Foxhollow is a secluded resort located in the heart of the Berkshire Mountains at 3 Fox Hollow Drive, Lenox, Massachusetts. The resort offers one and two bedroom condominiums for timesharing or rental purposes, each with a master bedroom, fully equipped kitchen, living area with a double sleeper sofa, and a deck overlooking a picturesque pond. The property spans 223 acres, perfect for hiking in the warmer months and cross country skiing in the winter. The resort also offers outdoor activity equipment and canoes for guests to use. With breathtaking mountain views and a variety of recreational and cultural activities nearby, The Ponds at Foxhollow is the perfect destination for a relaxing getaway. Please note that the hot tub is temporarily out of service, but a new one is on the way.

Blantyre is a luxurious lodging institution located at 16 Blantyre Road in the picturesque town of Lenox, Massachusetts, United States. This historic property offers elegant accommodations, impeccable service, and stunning views of the surrounding Berkshire Mountains. Guests can enjoy fine dining, relaxing spa treatments, and a variety of outdoor activities on the expansive grounds. Blantyre is the perfect destination for a romantic getaway, a special occasion, or a relaxing retreat in a beautiful New England setting.

Garden Gables Inn is a charming lodging establishment located at 135 Main Street in Lenox, Massachusetts, United States. Nestled in the heart of the picturesque town, this historic inn offers a tranquil escape for guests looking to relax and unwind. The beautifully landscaped gardens surrounding the property provide a peaceful setting for guests to enjoy. The inn features elegantly appointed rooms and suites, each uniquely decorated with a blend of modern amenities and classic charm. Guests can start their day with a delicious breakfast served in the cozy dining room or out on the sunny terrace. With its convenient location near local attractions, shops, and restaurants, Garden Gables Inn is the perfect choice for a memorable stay in Lenox.

The Dewey is a charming lodging establishment located at 7 Hubbard Street in Lenox, Massachusetts. This cozy inn offers comfortable accommodations in a picturesque setting, perfect for those looking to relax and unwind in the heart of the Berkshires. The Dewey's convenient location allows guests to easily explore the many attractions and activities in the area, including historic sites, art galleries, and outdoor adventures. With its warm hospitality and inviting atmosphere, The Dewey is the ideal destination for a peaceful getaway in the beautiful New England countryside.

Berkshire Homes and Condos is a reputable real estate agency located at 48 Saint Ann's Avenue in Lenox, Massachusetts, United States. Specializing in luxury homes and vacation condos in the picturesque Berkshire region, this agency offers exclusive listings and full property details for interested buyers and renters. With prices and inventory updated as of April 5, 2024, Berkshire Homes and Condos provides unparalleled service and expertise in the local real estate market. To access their full range of properties and continue your search, simply agree to their Terms of Use.

White Pines Condominiums, located at 19 Hawthorne Road in Stockbridge, Massachusetts, offers a picture-perfect Carriage Barn unit with all the benefits of condo living. This home features an open common space with a wall of windows for natural light, a pretty setting, large great room, galley kitchen, separate dining area, bonus dining room/office, three bedrooms, two and a half baths, sunroom, and private deck. Residents can enjoy common amenities such as an indoor pool, exercise room, tennis courts, association beach, and walking trails. Conveniently located near Tanglewood and Lenox Village, this home is a must-see for those seeking a comfortable and luxurious living space. White Pines Condominiums serves real estate buyers and sellers in Massachusetts and New York, with a location at 47 Church Street PO Box 1650 in Lenox, Massachusetts 01240.

Piretti Real Estate is a reputable real estate agency located at 22 Walker Street in Lenox, Massachusetts, United States. With a team of experienced and dedicated professionals, Piretti Real Estate is committed to helping clients buy, sell, and rent properties in the Lenox area and beyond. Whether you are looking for a cozy cottage, a luxury estate, or a commercial property, Piretti Real Estate can assist you in finding the perfect property to meet your needs. Contact them today to start your real estate journey!

Welcome to Karen Climo Real Estate, your trusted partner in navigating the vibrant real estate market of the Berkshires. Conveniently located at 292 Main Street, Great Barrington, Massachusetts, our agency is dedicated to providing exceptional service to both buyers and sellers. Led by Karen Climo, a founding agent with William Pitt Sotheby's International Realty's Berkshire Brokerage, we bring unparalleled expertise and commitment to every real estate transaction. Karen Climo's journey into real estate began in 2007, following her successful tenure as Development Director at Shakespeare & Company in Lenox. With a background in new construction homes since 1996, Karen combines her passion for real estate with a deep understanding of the local market. Her high-energy approach, attention to detail, and integrity ensure that clients receive personalized and efficient service tailored to their unique needs.

Welcome to Wheeler & Taylor Realty, your trusted partner in real estate since 1871. Conveniently located at 10 Elm Street in the charming town of Stockbridge, Massachusetts, we are proud to serve the vibrant communities of Southern Berkshire County. Our experienced team is dedicated to helping you find the perfect property, whether you're searching for a single-family home, a vacation retreat, or a commercial investment. At Wheeler & Taylor Realty, we specialize in a diverse range of real estate options to meet your needs. From single-family homes priced up to $750,000 to luxurious estates over $1,000,000, we cover the entire spectrum from Lenox/Richmond south to the Connecticut border. Explore beautiful homes located on or near the water, or find the perfect condo in any price range. We also offer parcels of land and commercial listings for those looking to build or invest.

Welcome to Mark Parsons, ROBERTS & ASSOC. REALTY, INC., your trusted partner in real estate located in the heart of Lenox, Massachusetts. Situated at 48 Housatonic Street, our office is dedicated to providing exceptional real estate services to the Berkshire community and beyond. Whether you are buying, selling, or renting, our experienced team is committed to delivering personalized service tailored to meet your unique needs. At Mark Parsons, ROBERTS & ASSOC. REALTY, INC., we pride ourselves on our deep local knowledge and extensive expertise in the real estate market. Our team of professional agents is here to guide you through every step of your real estate journey, ensuring a seamless and stress-free experience. We offer a comprehensive range of services, including residential and commercial property sales, property management, and rental services.

Welcome to Paula McLean Realtors Located at 54 King William Road, Lenox, Massachusetts, Paula McLean Realtors is your trusted partner in navigating the dynamic real estate market of Berkshire County. With over four decades of experience since 1981, Paula McLean has established herself as a prominent figure in the real estate industry, proudly holding four prestigious national designations: Accredited Buyers Representative, Certified Residential Specialist, Accredited Staging Professional, and Resort and Second Home Property Specialist.

Welcome to Dani Giulian Real Estate, where your real estate dreams become a reality. Located at 24 Donna Avenue, Pittsfield, Massachusetts, Dani Giulian is a licensed Realtor who brings years of experience and a deep passion for real estate to the beautiful Berkshires. With a background in sales, finance, and a commitment to excellence, Dani provides a seamless experience for home buyers and sellers alike. Dani is not just a Realtor; she is a dedicated partner in your real estate journey. Known for her honesty, integrity, and innovative problem-solving skills, she excels in helping clients navigate the complexities of buying and selling homes. Her strong referral business is a testament to the trust and satisfaction of her past clients, who frequently describe her as highly responsive, dependable, knowledgeable, and caring.