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$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

$35,000
73544439 MLS
Welcome to 26 Deer Run in Becket, MA. This beautiful, buildable lot offers the perfect blend of privacy and natural surroundings. The property previously received a passing perc test, which has since expired, providing a strong starting point for future development plans. Nestled among mature trees and scenic landscapes, the lot offers a peaceful setting to enjoy throughout the year. Conveniently located near local lakes, hiking trails, and a variety of outdoor recreational opportunities, 26 Deer Run provides easy access to everything Becket and the surrounding Berkshire region have to offer. Enjoy the charm of small-town living while remaining within reach of shopping, dining, cultural attractions, and major routes. Whether you're looking to build a year-round residence or a seasonal retreat, this property presents an excellent opportunity to create your vision in the heart of the Berkshires.

26 Deer Run, Becket

$35,000
73544436 MLS
Welcome to 25 Deer Run in Becket, MA. This beautiful, buildable lot offers the perfect blend of privacy and natural surroundings. The property previously received a passing perc test, which has since expired, providing a strong starting point for future development plans. Nestled among mature trees and scenic landscapes, the lot offers a peaceful setting to enjoy throughout the year. Conveniently located near local lakes, hiking trails, and a variety of outdoor recreational opportunities, 25 Deer Run provides easy access to everything Becket and the surrounding Berkshire region have to offer. Enjoy the charm of small-town living while remaining within reach of shopping, dining, cultural attractions, and major routes. Whether you're looking to build a year-round residence or a seasonal retreat, this property presents an excellent opportunity to create your vision in the heart of the Berkshires.

25 Deer Run, Becket

$235,000
3 Beds 2 Baths 73540567 MLS
Welcome to this spacious 3-bedroom, 2-bath home offering 1,920 square feet of living space in Pittsfield's desirable Morningside neighborhood. This home blends classic character with several major updates already completed, including a newer roof (2025), replacement windows, oil tank (2024), boiler (2019), and sewer line (2019). The flexible floor plan provides plenty of room for everyday living, entertaining, or multi-generational needs. Enjoy an eat-in kitchen, full basement with interior and exterior access, a detached one-car garage, and a generous lot with mature landscaping. Conveniently located near parks, schools, restaurants, shopping, and downtown Pittsfield. Located in an RM-zoned district, this property may offer future multi-family or investment potential, subject to buyer due diligence. Property is being sold AS IS. A great opportunity for investors, cash buyers, or conventional financing buyers looking to add value while building equity through cosmetic improvements.

20 Curtis Ter, Pittsfield

$125,900
1 Beds 1 Baths 73539589 MLS
Rare summer home opportunity at Klondike Campground Resort in turn-key condition! Nestled away from the road with a circular driveway, this 1996 model has a cheery eat-in kitchen, well appointed bedroom, big sunny Berkshire room & sleeper sofa for guests. The pretty deck leads to a tranquil side yard w/fire pit and wooded view. It also boasts an open floorplan plus 2 sheds! Klondike Campground Resort is a unique deeded community that features a giant clubhouse w/lots of amenities, a large solar-heated pool w/poolside cafe, community fire pit, updated playground, picnic area, exercise room, basketball, tennis & pickleball courts, onsite pond for kayaking or fishing, trails, and more! Many organized events also give this gated campground a true sense of community! Klondike certainly is “the Berkshires’ Best Kept Secret”! It’s a wonderful, and affordable, place as your home from 5/1 to 10/15, and a great place to visit year-round to enjoy local trails, skiing, fishing, and the nearby outlet mall! Other wonderful nearby attractions include Tanglewood, Jacob’s Ladder, Otis Ridge Skiing, Tolland State Forest, and the famous Otis Reservoir. Local country stores, eateries, and theatre and arts destinations all give additional charm to the area, as well as the summer concert series in Lenox. So much to do… or just stay within Klondike for relaxation or organized activities as well! This special seasonal home has something for everyone!

759 North Main Road Unit V7-12, Otis

$179,999
73538817 MLS
Discover the potential of this beautiful 17 Acre piece of land located in the Berkshires! This parcel offers a great opportunity for your next home site, small farm, or investment property. The area is known for its quiet rural setting while still being within a short drive to local amenities and schools. This property offers a peaceful atmosphere while maintaining plenty of room to spread out and enjoy country living. Mature trees create a natural buffer, enhancing privacy and providing a picturesque backdrop for your future home. Whether you envision a custom-built estate, outdoor recreation areas, or simply a tranquil retreat from the hustle and bustle, this property offers endless possibilities. Don't miss your chance to own land in the Berkshires bring your plans and make it yours!

Frost Rd, Washington

$220,000
7 Beds 3 Baths 73538546 MLS
Bring your vision and creativity to this spacious side-by-side duplex that's been stripped down and prepped for its next chapter. Much of the heavy lifting has already been completed, including extensive demolition work and rough electrical installation. The exterior has also received a 1st of coat of paint. Originally intended to be converted into townhouses and sold separately, the owner's plans have changed, creating an exciting opportunity to customize a property to their needs. One unit offers 4 bedrooms and 1.5 baths, while the second features 3 bedrooms and 1.5 baths. Both units include private enclosed front porches, open rear porches, and spacious layouts ready to be transformed. The walkout basement opens to the backyard and offers additional possibilities. Whether you're looking to create income-producing rentals, pursue a townhouse conversion, or design your dream multi-generational property, this diamond in the rough is packed with potential.

27 Daniels Ave, Pittsfield

$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

$799,000
73534596 MLS
Rare opportunity to acquire a unique five-parcel package totaling approximately 33.37 acres in scenic Williamstown. Offered as one sale, the package includes 95 & 97 Luce Road, each with an existing residence situated on 5.50 and 5.90 acres respectively, plus three additional raw land parcels totaling approximately 21.97 acres. The existing homes are in significant disrepair and are best suited for redevelopment, renovation, or replacement. This offering presents a variety of possibilities including an estate property, recreational retreat, investment opportunity, or potential future development. Set amidst the natural beauty of the Berkshires, the property enjoys a peaceful setting with potential mountain and countryside views, while remaining convenient to Williams College, downtown Williamstown, and Mount Greylock. Existing road frontage, access, and utility infrastructure add value beyond raw land alone. Buyer to independently verify all information, including zoning and land use.

97 Luce Rd, Williamstown

$799,000
2 Beds 1 Baths 73534578 MLS
Rare opportunity to acquire a unique five-parcel package totaling approximately 33.37 acres in scenic Williamstown. Offered as one sale, the package includes 95 & 97 Luce Road, each with an existing residence situated on 5.50 and 5.90 acres respectively, plus three additional raw land parcels totaling approximately 21.97 acres. The existing homes are in significant disrepair and are best suited for redevelopment, renovation, or replacement. This offering presents a variety of possibilities including an estate property, recreational retreat, investment opportunity, or potential future development. Set amidst the natural beauty of the Berkshires, the property enjoys a peaceful setting with potential mountain and countryside views, while remaining convenient to Williams College, downtown Williamstown, and Mount Greylock. Existing road frontage, access, and utility infrastructure add value beyond raw land alone. Buyer to independently verify all information, including zoning and land use.

97 Luce Rd, Williamstown

$810,000
73531653 MLS
Don’t be late for this redevelopment opportunity! 18,000 Sqft on 1.1 Acres. Structurally sound property offers a rare opportunity to transform a historic space into a vibrant new community. Preliminary estimates suggest the potential for 12 residential units, with ample room for parking and green space. Featuring solid brick construction. Expansive windows, high ceilings, and open floor plans, this property is ideal for adaptive reuse into loft-style apartments, townhomes, or mixed-use development. Conveniently located in a growing area with access to local amenities, schools, and transportation. this site is primed for investors and developers seeking their next project. Don’t miss this A+ Investment. schedule your private tour today! This Property can be bundled with 48 Brown & 242 Wahconah st

40 Pecks Rd, Pittsfield

$375,000
6 Beds 2 Baths 73531392 MLS
Escape to the Berkshires in this stunning Victorian gem — designed for those who appreciate space, style, and character. Whether you're planting roots in North Adams or seeking a weekend retreat. Fully renovated 5-bed, 2-bath home with 2,551 sq ft in the heart of North Adams. Slate roof, repainted front porch, chimney repairs, and updated plumbing and electrical throughout. Inside features refinished black India ink hardwood floors, new lighting fixtures, popcorn ceiling removal, washer/dryer hookups, and designer finishes including Revere Pewter and Gentlemen's Grey. Both bathrooms fully refreshed with new tile, fixtures, and flooring. Furniture included.Minutes from Mass MoCA and the Mohawk Trail. Proven short-term rental with 4 years of documented Airbnb performance, consistent 5-star guest reviews. Professional management on 24/7 - completely turnkey. Active Airbnb listing available upon request to verify income history. Showings available between guest stays.

71 North Holden St, North Adams

$1,100,000
4 Beds 3 Baths 73531374 MLS
EXCEPTIONAL WATERFRONT RETREAT ON TRANQUIL HAYES POND!Nestled on over 3 private acres w/an extraordinary 650 feet of frontage on Hayes Pond,this exceptional waterfront retreat offers sweeping elevated views,a private dock, sandy beach, & direct access to swimming, kayaking, & fishing.Designed to embrace its stunning natural setting,the home features expansive windows & multiple outdoor living spaces, including a wraparound deck, waterside gazebo, & screened porch w/hot tub connection--perfect for entertaining or relaxing in every season.The bright open-concept interior includes 4 bedrooms & 3 full baths,highlighted by a dramatic great room w/ knotty pine ceilings,a wood-burning stove w/stone hearth, & direct deck access overlooking the water.The spacious primary suite also opens to the deck & features its own and features its own wood-burning stove & en suite bath.The walkout lower level offers additional living space w/ a family room,full bath,& two and two bedrooms ideal for guests.

13 Hayes Pond Rd, Otis

$550,000
73531162 MLS
Impeccable mixed use commercial with residential located on one of Berkshire Counties busiest corridors. Two storefronts located near local restaurants in the center of Adams business district. Once occupied by real estate firms, gift shops and bakery sales, bring your business or vision to write its next chapter. Great corner location with deeded parking and in very close proximity to grocery stores, restaurants, doctors offices and shopping. The 4 residential units are currently mixed with a short and long term model that has afforded nice returns. Live, work and play or just add this to your investment portfolio.Recent updates include electrical, roof, exterior paint and residential unit remodels.Under 3 hours to Boston and less than 3.5 hours to NYC. You can even take the Amtrak Train from the Berkshires to Penn Station if easier.

57-63 Park Street, Adams

$239,900
2 Beds 1 Baths 73530997 MLS
Charming bungalow in the heart of North Adams w/ beautiful mountain views! Conveniently located near downtown, offering easy access to restaurants, shopping, MASS MoCA, Hospital, and a vibrant art & cultural scene. Designed for comfortable one-level living, the home features beautiful hardwood floors throughout, vinyl windows, 2 bedrooms, and a spacious living/dining combination w/ a pellet stove. The kitchen features tile countertops, S/S appliances, and ample cabinetry. The front porch includes 1st floor laundry & built-in shelving. There is a full basement & a Walk-up attic. Outside, you'll appreciate the low-maintenance stone exterior, mature landscaping, a large paved driveway, and a 2 car garage. The property is just 30 minutes from Jiminy Peak Mountain Resort & Mount Greylock, & only 10 minutes from Williamstown & Vermont. Whether looking for a primary residence or a Berkshire getaway, this home offers comfort, convenience, & easy access to the region's most popular attractions.

21 River St, North Adams

$1,450,000
3 Beds 3 Baths 73527324 MLS
Discover an extraordinary lakefront opportunity on Otis Reservoir featuring a combination of amenities rarely found in a single package. Combined with the lower lot, enjoy 62 feet of direct waterfront, a super rare grandfathered boathouse dock with electricity and electric lift, a waterfront bathhouse with living room, heated garage, dedicated hot tub room with fireplace, and a floor plan designed to capture stunning lake views from nearly every room. Perfect for entertaining, the home offers a spacious updated kitchen, multiple living areas, separate driveways with ample off-street parking, and two storage sheds for all your lake and seasonal gear. Extensively remodeled in 2021 with new heating and cooling systems, on-demand hot water, and a beautiful kitchen featuring stacked cabinetry, full-slab quartz countertop island, stainless steel appliances, and a gas range. The walk out basement provides easy access to the outside as well. Sold fully furnished and ready to enjoy from day one

347 Pine Rd, Otis

$660,000
5 Beds 3 Baths 73522628 MLS
Tucked away on a serene & private lot just minutes from the sparkling waters of Otis Reservoir, this stunningly renovated 5-bedroom, 3-bath Colonial offers the perfect blend of luxury, comfort, and natural beauty. Designed for both elegant entertaining and everyday living, the heart of the home is the spectacular chef’s kitchen featuring quartz countertops, abundant cabinetry, and refined finishes throughout. The thoughtfully designed 1st flr offers a formal living room, sophisticated dining area, two spacious bedrooms, and a beautifully updated full bath — ideal for guests or flexible living arrangements. Upstairs, retreat to the luxurious primary suite complete with a private ensuite bath, along with two additional generously sized bedrooms and a third full bath. Surrounded by peaceful nature views, trails and exceptional privacy, this remarkable property is a rare opportunity to enjoy upscale living in a tranquil setting to enjoy all the beauty the Berkshires have to offer.

23 Old Blandford Road, Otis

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