Lee, MA Classified Ad Listings

10 Berkshire Heights Rd. Luxurious, fully-modernized 1850s Victorian in the heart of Great Barrington. Elegant, four-story 3600 sq. ft. newly renovated clapboard and shingle house with covered porch. Meticulous renovation features chef's kitchen, 4+ bedrooms, 4.5 bath, second floor and basement laundry, walk-out finished basement with private entrance and bathroom, perfect for guest suite or pr...

201 Chanterwood Rd. Set in the heart of the Berkshires of Lee, Mass, this beautifully maintained 4-bedroom home captures the essence of Berkshire living with panoramic, elevated views for all 4 seasons that will leave you speechless; particularly in Autumn, when views in the Berkshires explode with color. A 4th oversized garage below the house is the perfect place for all of your toys. Inside, ...

3664 Jacobs Ladder Rd. Enjoy life on Greenwater Pond in the Berkshires! The views, boating, fishing or just relax and at the end of the day watch the beautiful sunsets all from your little piece of lakefront heaven. I'll let the pictures speak for themselves. This property features a cottage with 3 Bedrooms,eat-in Kitchen and 1 full bath, a large barn and storage shed. Just about a 4 mile trip ...

14 Stockbridge Ave. **NEW ROOF TO BE INSTALLED ON HOUSE and GARAGE PRIOR TO CLOSING*** Set on a quaint, centrally located side street, this inviting 1,593 sq. ft. Cape offers the perfect blend of timeless character and flexible living space. The layout features 2 to 3 bedrooms, including a main-floor bedroom or home office alongside a convenient full bath on the main level. Upstairs, you will f...

554 Main St. 3.21 Acres - Two Garages plus a Full Walkout Basement! This beautifully maintained 1,900 sq. ft. ranch offers comfortable single-level living with a bright, open floor plan and plenty of natural light. An inviting kitchen features marble countertops, while beautiful hardwood floors and a custom fireplace add warmth and character throughout. The spacious walkout basement includes a ...

53 Orchard Road. Single Family Home for sale in North Canaan, CT for $499,000 with 3 bedrooms and 2 full baths. This 1,937 square foot home was built in 1955 on a lot size of 0.57.. Welcome to this beautifully renovated and professionally decorated 3-bedroom, 2-full-bath ranch, offering the perfect combination of style, comfort, and easy one-level living! Thoughtfully updated throughout, this h...

181 New Lenox Rd. Enchanting Lenox Cottage minutes to Tanglewood- 2 Bedroom / 2 Full Bath Retreat The bright, airy living room features warm wood floors that lead into a cozy eat-in kitchen. With a heated sunporch and 1st floor full bath, the home offers multiple inviting spaces to relax or entertain. Step outside to a brand-new back deck, an ideal setting for summer evenings. 2 Bedrooms on sec...

L45 Jacobs Ladder Rd. Discover the serene beauty of the Berkshires with this 10.1-acre property, complete with a babbling stream and old stone walls, providing plenty of privacy for your retreat. This ideal location offers easy access to the best of Becket and the Berkshires, including the renowned Jacob's Pillow Dance Festival and the scenic trails of October Mountain State Forest. Whether you...

Seneca Dr. Enjoy lake living on your own two acres as part of the Indian Lake association! This private resort community was established in 1980. Within the boundaries of the 676 acre paradise you'll find a private lake with swimming beaches, canoe/kayak storage, a nature pond, tennis courts, and quiet, unpaved country roads.

229 Hamilton Rd. Tucked well back from the road on 3.5 private acres, this modern, lightly used home offers an effortless blend of low-maintenance living, single-story convenience, and quintessential Berkshires charm. Designed with an open, light-filled layout, the main level features gleaming hardwood floors and an seamless flow throughout the common living areas. At the heart of the main floo...

293 New Marlborough-Sandisfield Rd. Just beyond New Marlborough Village this architectural gem showcases 5,653 square feet of superior craftsmanship along the Umpachene River. Built in 1989, this 5-bedroom home was designed by internationally renowned architect Paul Bierman-Lytle, a pioneer in sustainable development and healthy home design known for championing non-toxic climate adaptive build...

19 Hawthorne Rd Unit GH8. Make this fabulous White Pines Garden Unit your next home in the Berkshires in this sought after community. Cathedral ceiling Great Room open to dining and updated kitchen w/beautiful natural light and two story wall of glass with primary en suite and guest bedroom w/full bath, bonus room on lower level all leading to your private deck with amazing privacy. Amenities i...

54 New Hartford Rd. Brand new, never occupied, pristine new build on over 4 acres in beautiful Sandisfield. This home was built with a keen eye for detail and a focus on beautiful finishes and materials that harmonize with the landscape. Bright, airy, and filled with positive energy, the space invites you in and makes you feel right at home. There are soaring ceilings in the great room and a co...

Color: Black. Coat: Bicolor. Born: 03/25/26 - 6 months. Rosie Von BridleWoof Rosie was withheld from this March 25, 2026 exceptional litter for foundational training. She is crate trained, house trained and well socialized! A silent phantom, her copper markings will continue to emerge over time, gradually revealing a beautifully understated phantom pattern. She has a gentle, deeply connected na...

162 Alford Rd. BEAUTIFUL, PRIVATE LOT! Gently sloped and lightly wooded parcel awaits your thoughtful build. Bring your design to life at this private and convenient location. Electric has been brought to the site, perc test available. Seasonal views. Wonderful location with easy access to Great Barrington town center, shops, restaurants, hiking and skiing!

Quarry Rd. Quarry Rd Paradise on 5+ Acres. Several prime House locations with possible views. Existing Logging Roads make access easy and the Property has been perc'ed (ready for Septic). Close to Jacobs Pillow and many Berkshire Attractions. The time to build that dream house is now !

11 Hawthorne Rd. The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody and Stearns, this 16th-century Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur...

80 Taconic Ave Apt 12. ''ON THE HILL'' Condo at The Oakwoood! Town-House style unit in a prime location. Located in a highly desirable setting, this property offers easy access to town, putting Shops, Dining, and local amenities just minutes away. 3-Bedrooms, 2-Baths,a large Living Room with vaulted ceiling and fireplace, Enjoy the community pool and beautifully landscaped property. Have coffee...

4 Gilmore Ave. Set on two-thirds of an acre in a residential area, walkable to all Great Barrington has to offer, this versatile home offers 4+ bedrooms and 3 bathrooms. The main floor boasts two bedrooms, a dedicated office or guest space, one and a half baths, laundry, as well as the main living, dining, and kitchen areas. Upstairs you will find 2 additional bedrooms and another half bath. Wo...

77 Vandenburg Rd. Be Entralled this Summer.. Among this immaculate 2800sqft Hudson Valley home's features are living room w/ FIREPLACE - 3 bedrooms, 3.5 baths, wrap-deck, walls of windows and 15 acres of absolute serenity overlooking STUNNING VALLEY and LAKE VIEWS at Berkshire's foothills. Each BR features its own bathroom, including a bedroom suite with PRIVATE SAUNA over the attached 2-car ga...