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$1,795,000
4 Beds ⋅ 6 Baths ⋅ 24193129 MLS
MAGNIFICENT circa 1913 ESTATE with CARRIAGE HOUSE Rare opportunity to own a distinguished estate featuring two residences on more than six private acres. The stately main home at 1 Park Avenue showcases exceptional craftsmanship, a grand foyer with sweeping staircase, expansive kitchen with butler's pantry, formal living spaces, sun porch, and multiple covered porches. The luxurious primary suite offers a sitting room, balcony, sun porch, and spa-like bath. Three additional bedrooms, office, and finished third floor provide ample living space. The charming carriage house at 5 Park Avenue features 4 bedrooms and flexible accommodations for guests, extended family, caretakers, home office, or income potential. Attached 2-car garage, mature grounds, and exceptional privacy complete this remarkable estate.

1 And 5 Park Ave, Dalton
$1,795,000
4 Beds ⋅ 8 Baths ⋅ 73552517 MLS
MAGNIFICENT circa 1913 ESTATE with CARRIAGE HOUSE. Rare opportunity to own a distinguished Berkshire estate featuring two residences on more than six private acres. The stately main home at 1 Park Avenue showcases exceptional craftsmanship, a grand foyer with sweeping staircase, expansive kitchen with butler's pantry, formal living spaces, sun porch, and multiple covered porches. The luxurious primary suite offers a sitting room, balcony, sun porch, and spa-like bath. Three additional bedrooms, office, and finished third floor provide ample living space. The charming carriage house at 5 Park Avenue features 4 bedrooms and flexible accommodations for guests, extended family, caretakers, home office, or income potential. Attached 2-car garage, mature grounds, and exceptional privacy complete this remarkable estate. See the Stone House Properties web site for further details.

1 and 5 Park Ave, Dalton
$14,500,000
25 Baths ⋅ 73544528 MLS
The Wheatleigh: Former 5 Star Forbes Travel Property and 'Leading Hotel of the World', this Gilded Age masterpiece sits on over 21 acres overlooking Stockbridge Bowl. Designed in 1893 by Peabody & Stearns, this 16th-century Florentine palazzo features stunning grounds by Frederick Law Olmsted. At Tanglewood's doorstep, this 25,000+SF architectural sanctuary marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, Parlors, 3 formal Dining Rooms, Wine Cellar (6,500-bottle capacity), meeting rooms, massage room, Gym, and 19 Guest suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the Pool and Tennis Court. This iconic Inn offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.

11 Hawthorne, Stockbridge
$14,500,000
19 Beds ⋅ 25 Baths ⋅ 73544510 MLS
The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody & 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 with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.

11 Hawthorne, Stockbridge
$1,450,000
20 Beds ⋅ 18 Baths ⋅ 73536485 MLS
162 Woodlawn Ave is comprised of two (2) 2-Bedroom/1-Bathroom units, eleven (11) 1-Bedroom/1-Bathroom units, and five (5) Studio units with 8,653 square feet of gross living area in 11,653 square feet of gross area. The Property is situated upon a 0.47-acre parcel and offers twenty (20) off-street parking spaces. The Property is well-positioned within Pittsfield’s established Morningside neighborhood, offering convenient access to downtown amenities while maintaining a residential setting. The Property is separately metered for electricity, while the Landlord is responsible for gas powered heat & hot water, as well as domestic water & sewer. The Property benefits from quick access to U.S. Routes 7 and 20, which link the city to the Massachusetts Turnpike (I90) at Exit 10 in Lee, creating efficient regional highway connectivity toward Springfield, Worcester, Boston, Albany, and New York State. The opportunity exists to acquire a well maintained asset in the beautiful Berkshires area.

162 Woodlawn Ave, Pittsfield
$3,750,000
34 Beds ⋅ 31 Baths ⋅ 73518284 MLS
Rare 16.76± acre contiguous institutional campus and redevelopment opportunity in Lenox, MA, in the heart of the Berkshires. Anchored by Overlee, a historic 1903 estate, the property includes multiple buildings with 32 dormitory-style bedrooms, classroom and administrative space, dining facilities, shared common areas, and a large gymnasium. Existing infrastructure includes internal roadways, parking, public water, sprinkler systems, mixed heating, and up to 600 amp electrical service. Also included is a 1,826 SF residence on 4.74± acres across three contiguous parcels offering additional flexibility. Currently operated as an educational campus, the property offers compelling long-term potential for institutional, residential, wellness, medical, hospitality, or mixed-use concepts. Buyers to conduct due diligence.

349 Old Stockbridge Rd, Lenox
$3,750,000
31 Baths ⋅ 73518283 MLS
Rare 16.76± acre contiguous institutional campus and redevelopment opportunity in Lenox, MA, in the heart of the Berkshires. Anchored by Overlee, a historic 1903 estate, the property includes multiple buildings with 32 dormitory-style bedrooms, classroom and administrative space, dining facilities, shared common areas, and a large gymnasium. Existing infrastructure includes internal roadways, parking, public water, sprinkler systems, mixed heating, and up to 600 amp electrical service. Also included is a 1,826 SF residence on 4.74± acres across three contiguous parcels offering additional flexibility. Currently operated as an educational campus, the property offers compelling long-term potential for institutional, residential, wellness, medical, hospitality, or mixed-use concepts. Buyers to conduct due diligence.

349 Old Stockbridge Rd, Lenox
$2,950,000
7 Beds ⋅ 8 Baths ⋅ 24171893 MLS
Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare blend of colonial charm and equestrian excellence. Spanning 27.3+ bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence/Inn, three enchanting cottages, and the potential to include the region's premier full-service equestrian facility. The main residence, a testament to time-honored craftsmanship, features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. The main house/inn's dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that cater to both intimate family gatherings and grand celebrations. For the serious equestrian, the estate offers multiple barns and paddocks. Training is a year-round luxury thanks to the 6,000 sqft heated indoor arena, which includes an owner's apartment and viewing area - and a professional grade outdoor ring. Enjoy all the area attractions including Tanglewood, the Mount, MASS MoCa and breathtaking hiking trails.

802 State Rd, Richmond
$4,850,000
13 Beds ⋅ 14 Baths ⋅ 73496031 MLS
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.

2 Kemble, Lenox
$7,250,000
6 Beds ⋅ 7 Baths ⋅ 24151033 MLS
A rare French Manor estate on one of the most scenic and sought-after country roads, this extraordinary 45+/- acre sanctuary offers unmatched privacy, panoramic mountain views, and a setting of timeless beauty. Bordering protected state forest, the property unfolds across rolling meadows, tranquil ponds, and a gently flowing brook-creating a secluded retreat that feels worlds away, yet remains moments from the cultural heart of the Berkshires. It is awaiting buyers final finishes. At the center of the estate stands a newly built main residence inspired by the grand proportions of the Gilded Age, featuring soaring 19-foot ceilings and impeccable architectural presence. Thoughtfully constructed by a highly regarded local craftsman, the home showcases state-of-the-art mechanical systems, including geothermal heating and cooling, blending classic elegance with modern efficiency. Approaching completion, the residence presents a rare opportunity for the next owner to personalize select finishes and make this remarkable home truly their own. A short stroll west leads to a beautifully converted barn guest house, carefully relocated to the property and transformed into a dramatic open-concept retreat. Soaring ceilings, antique beams, and expansive windows frame the estate's sweeping mountain and pond views, creating an inviting space for guests, artists, or quiet reflection.

209 Blue Hill Rd, Great Barrington
$3,998,000
5 Beds ⋅ 6 Baths ⋅ 24142076 MLS
WHERE THE WORLD FALLS AWAY 227 acres. 227 years. At East Hill Road's summit, East Hill Farm is a fully realized estate where infrastructure, land, and possibility are complete and in place. The 1798 Thomas Shepard House-museum-quality restoration featuring 5 bedrooms, 5.5 baths, 5 fireplaces, original King's board floors, hand-blown glass windows-awaits your vision for kitchens and baths. Modern additions: radiant heat, elevator, sun-filled library, luminous sunroom overlooking formal gardens and 4-acre spring-fed pond. The 227 acres aren't just land-they're composition. Meadow unfolding to pond positioned where morning & evening light catch it. Mature forest giving way to unbroken views. Trails looping you gently home by blue hour. Stone walls, pool, tennis court, greenhouse. Magnificent 3,550sf hand-hewn barn moved here. Northern land borders State Forest; southern abuts conservation land-permanent privacy. Guest house (6,668sf): 4 residences replete with possibilities-multigenerational living, art studios, writing spaces, media rooms, yoga, creative sanctuary. Cathedral ceilings, fireplaces, soaring light. The quiet money cannot buy: depth of silence settling at dusk, Milky Way stretching clear across valley, no light pollution. Architecture, land, and sky speaking the same language. Where hosting feels like breathing, completely natural. 5 families in 227 years. You'll be 5th. 5 min to dining, 20 min to Great Barrington, 2.5 hrs to Boston/NYC. Complete and irrepla

764 E Hill Rd, New Marlborough
$3,998,000
5 Beds ⋅ 6 Baths ⋅ 73451336 MLS
East Hill Farm offers 227 acres of protected quiet, anchored by the elegant 1798 Thomas Shepard House. A private hilltop world.Main house: Georgian-Federal; 5 BR, 5.5 BA, ~5,000 SF; 5 fireplaces; unusually high ceilings, wide-board floors, antique glass, rooms that hold the light, views that connect. Graceful, welcoming.A complete estate that also can be a working-farm or equine property: barns + outbuildings, pastures, private trails + roads, 4+ acre pond, gardens + orchard, pool, pool house, greenhouse, tennis.A vast former Arabian horse barn, now guest compound, or for you to reimagine. Preserved with rigor, lived in with joy, and rooted in the land and history that defines the Berkshires. One of the most complete and intact agricultural landscapes remaining in Southern Berkshire County, has no true comparable. Read the history. Experience East Hill Farm. Reach out.

764 East Hill Road, New Marlboro
$9,500,000
7 Beds ⋅ 9 Baths ⋅ 73445189 MLS
Offered with Seller Financing, this Majestic Tudor Berkshire Estate sits on 71 Acres atop Tom Ball Mountain in quaint Alford, MA. Privacy and Breathtaking views. Formal Entry and Foyer. Stately Living Room and Dining Room. Great Room with Gourmet Kitchen. Den, Family Room, Gym and Massage Room. 5 en-suite Bedrooms in the Main House. 2 Bedroom Tudor Guest House w beamed ceilings and full amenities. Manicured grounds, infinity Pool and Hot Tub, Pool House with full Bath, Tennis Court and Pickleball Court. 7 Garages and additional Barn. Exquisite architectural touches, state-of-the-art home technology and security, in the most peaceful of surroundings. Easy access by road, rail and private Airport. Close to Tanglewood and Berkshire attractions. *Fully Furnished and ready to enjoy.

30 East Rd, Alford
$5,650,000
11 Beds ⋅ 10 Baths ⋅ 24013888 MLS
Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of the future for generations to come. Set on 67 +/- park-like acres this property offers 3 unique residences, a mature specimen tree farm, a spring-fed pond, wooded walking trails, and captivating views of the distant mountains all just a stone's throw away to restaurants and shops. At the heart of the estate stands The Tullar House; a well-preserved and substantial 6-bedroom 5,000+ sq ft antique Dutch Gambrel dating back to 1761, reported to be the 2nd oldest house in Egremont. Retaining much of its original charm and detail, this historic jewel boasts ample-sized rooms for gatherings and entertaining, a renovated chef's kitchen, a formal dining room, 3 grand fireplaces, 2 primary suites, and plenty of room for guests. Enjoy sweeping views of the grounds from the porch laid with locally sourced marble or relish in the shade of 'The Champion', a 250+-year-old Black Walnut Tree standing as the oldest in the state and serving as a living testament to Tullar Farms' rich past. The exterior is a sight to behold with ornate and symbolic details that capture the attention of all who pass by.

25 Sheffield Rd, Egremont
$3,490,000
10 Beds ⋅ 6 Baths ⋅ 73431481 MLS
Welcome home to NEWGRANGE. 1920's era Manor House with lake frontage on Lake Garfield. Over 10,000 square feet of living on 7.7 Acres. Complete the restoration and enjoy original Stone Fireplaces, comfortable Living spaces, formal Dining and 10 Bedrooms. Write that novel in the paneled Office, Library or Sunroom, create delicacies in the Country Kitchen, or shoot a round of pool in the Billiard Room. When you are done, meander to your private Dock on 165 feet of glorious private lakefront. Guest House, Pond, and Gardens originally designed by Frederick Law Olmstead. Close to town, Skiing, Shopping, Dining and Tanglewood. Low, low Monterey taxes. This one-of-a-kind property is meant for enjoying all that the Berkshires has to offer.

535 Main Rd, Monterey
$1,750,000
22 Beds ⋅ 21 Baths ⋅ 73245373 MLS
The Possibilities are endless! Family Compound & Retreat ! Hotel, Wedding Venue, Campgrounds, Cross Country Skiing Trails or Family Compound, bring your imagination and bring Buck Steep Manor back to Life! Five Buildings and many Cabins amid this 350-acre Estate. The Manor House 25 rooms the Lodge 19 rooms the Dutch Colonial Barn 5 rooms the Cottage 10 rooms The Antique Carriage Barn Hall 99pl capacity, and the Post and Beam Utility Barn two levels. Photos are from the past when it was running as a venue. It has frontage on Washington Mt Rd, Frost Rd and Lovers Lane Rd. Come view this unique property you won't be disappointed. All Information to be confirmed by Buyer. See Also MLS Listing 73240084 in Commercial.

885 Washington Mt. Rd., Washington
$1,750,000
21 Baths ⋅ 73240084 MLS
The Possibilities are endless Hotel, Wedding Venue, Campgrounds, Cross Country Skiing Trails or Family Compound, bring your imagination and bring Buck Steep Manor back to Life! Five Buildings and many Cabins amid this 350-acre Estate. The Manor House 25 rooms the Lodge 19 rooms the Dutch Colonial Barn 5 rooms the Cottage 10 rooms The Antique Carriage Barn Hall 99pl capacity, and the Post and Beam Utility Barn two levels. Photos are from the past when it was running as a venue. It has frontage on Washington Mt Rd, Frost Rd and Lovers Lane Rd. Come view this unique property you won't be disappointed. See Also MLS # 73245373

885 Washington Mt. Rd., Washington

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