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68 Photos
STONE HOUSE PROPERTIES, LLC
$939,000
13 BD | 7 BA
Multi-Family

Well-maintained seven-unit investment property in a convenient Southeast Pittsfield location. This handsome brick building features spacious apartments, classic architectural character and practical layouts. Six units offer two bedrooms and one bathroom, while the additional basement-level apartment includes one bedroom and one bathroom that needs remodeling. Each unit features a fireplace mantel, rear porch with both interior and exterior access, along with a flexible front room that can be opened to the dining room. Additional improvements and amenities include replacement windows, on-site laundry, private off-street parking, individual basement storage areas for each apartment and a rear interior egress staircase serving all units. Heat and hot water are included in the rents.


70 Photos
TIFFANY ROBERTS PROPERTIES LLC
$949,000
3 BD | 3 BA
Residential - Single Family

Offered for the first time by its original owner, this is a rare opportunity to own an exceptional Pontoosuc Lake property and make it entirely your own. With 115 feet of direct water frontage, the property offers a generous setting to enjoy life on the lake. Designed for gathering and entertaining, this spacious lakefront home features a fireplaced living area, original walnut woodwork, stone countertop kitchen, first-floor primary suite, generously sized upstairs bedrooms, large second-floor bath, and covered porch overlooking the water. Wake up to incredible sunrises over the hills reflecting across the water. Spend your days swimming and boating right from your shoreline, head out onto the open lake to take in views of Mount Greylock, and cruise the water for the evening sunse


56 Photos
KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$975,000
4 BD | 5 BA
Residential - Condo/Townhouse

Rare opportunity to own a spacious four-bedroom, four-and-a-half-bath end-unit town home with three finished levels, a two-car garage, and multiple outdoor, screened in living spaces. Tucked into a quiet cul-de-sac and set back from the road, this inviting home enjoys a peaceful, wooded backdrop, abundant natural light, and convenient access to the community pool--an ideal setting for relaxed everyday living and entertaining. The main level centers around a sun-filled living room with vaulted ceilings, transom windows, and a gas fireplace. A french- door opens to an enclosed screened deck overlooking the woods, creating an easy connection between indoor and outdoor living. The kitchen features granite countertops, stainless


60 Photos
ROBERTS & ASSOC. REALTY, INC
$995,000
5 BD | 4 BA
Residential - Single Family

Gracious, elegant, and designed for living well, this exceptional center hall Colonial offers timeless character, beautiful mountain views, and an abundance of space. The welcoming entrance is accented by exquisite English stained glass, with wood floors flowing throughout the home. Five bedrooms and 3.5 baths provide room for family and guests, while grand living and dining rooms are perfect for entertaining. A spacious family room offers a more relaxed gathering space. The primary suite features cathedral ceilings and beautiful mountain views. Outside, covered patios and decks overlook a spectacular in-ground pool, gazebo, and bathhouse--creating a private setting for summer entertaining and relaxation. Thoughtful updates include a 2016 roof, 2023 driveway, and appliances updated 2023-26


42 Photos
Lamacchia Realty, Inc. - Dalton
$1,050,000
4 BD | 3 BA
Residential - Single Family

Wake up each morning to breathtaking sunrises over beautiful Pontoosuc Lake from this exceptional waterfront retreat. Perfectly positioned to capture panoramic water views, this stunning 4 bedroom, 3 bath home offers the ideal blend of comfort and style. An inviting open-concept floor plan is designed to maximize the spectacular views, seamlessly connecting the spacious living, dining, and kitchen areas to create the perfect setting for entertaining or simply relaxing by the water. Outside, enjoy the the expansive Trex decking overlooking the lake, a large private dock, gazebo and an outdoor shower. Whether your are searching for a year round lakefront home or the ultimate vacation getaway, this home delivers lake life at its best!


73 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$1,099,900
5 BD | 6 BA
Residential - Single Family

Live, Love, & Play in Blythewood Estates priced favorable $250,000 less than assessed value for a quick sale to allow you enjoyment this beautiful Berkshire season. A private enclave near premier Lake Onota to experience idyllic living in the Berkshire hills while creating lasting memories. This stunning 6000+ sf, 5 Bedroom, 5.5 bath colonial is thoughtfully designed and beautifully set on 3.42 manageable acres with sweeping meadow views nestled perfectly to create peace in nature while centrally located minutes to the culture, arts, museums, eclectic dining and central to Tanglewood and The Clark Art. Three levels of living create a blend of fun and entertainment with a degree of separation on levels. First floor offers one level easy living with a dramatic two story primary bedroom suit


11 Photos
BISHOP WEST REAL ESTATE
$1,101,800
4 BD | 4 BA
Residential - Single Family

To Be Built Home - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 8.94-acre lot (MLS #248342), featuring a private well, installed septic system, underground electric, and a 1,000-gallon underground propane tank. A proposed septic easement accommodates an abutting lot. Lots may be purchased separately. HOA maintains driveway and common land. Covenants require a minimum 2,000 sq. ft. home with two-car garage. Taxes shown are for land only.


36 Photos
NOCHER REALTY
$1,150,000
14 BD | 14 BA
Multi-Family

14 Unit investment opportunity! Located just outside of downtown Pittsfield and within walking distance to shops, restaurants, and the Colonial Theater. Classic brick exterior and excellent off street parking. All units feature one bedroom and separate utilities. Coin-op laundry located on site for additional income.


77 Photos
STONE HOUSE PROPERTIES, LLC
$1,200,000

Commercial

Historic 9-Unit Bed & Breakfast | ±10,560 SF on ±0.33 Acres Exceptional opportunity to own a beautifully maintained three-story historic bed & breakfast offering approximately 10,560 square feet on a ±⅓-acre lot. Within walking distance to the downtown theater/business district. This well-appointed property features nine unique guest suites, each with private baths and kitchenettes, blending classic charm with modern amenities. Large parking lot in the rear of the property also offers a separate right of way directly onto East Housatonic St. Guests are welcomed through an elegant entry foyer, leading to inviting common spaces including a parlor, formal dining room, and fully equipped common kitchen. The first floor also includes two spacious guest suites.


19 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$1,299,900

Commercial

Professional Light Industrial Office Park located in Central Berkshire County for ease and 7 mnute access to Major Routes 7 & 20 and Routes 8 & 9. Heavy Trucking Hauling, Ideal for Mail Distribution, Customer Service Offices & Entrance, Warehouse Space, Two Loading Docks, Room for Expansion on the Second Level. 23' -26' Ceiling Height. Refurbished Front End Office Space, Conference Room, Lunch Room, Private Offices, Conference Room, Employee Break Room, Mechanic Room in Warehouse. Redesign Options available for Individual Use upon Request. City Water,Sewer, Natural Gas. Rear Loading Docks, Reception Area, Bus Line and close to Major Routes for Ease of Transportation to Albany or Northhamptom 40 miles Pittsfield Amtrak Station 3.5 Miles.


14 Photos
STONE HOUSE PROPERTIES, LLC
$1,347,500
16 BD | 12 BA
Multi-Family

Excellent 8-Unit Investment Opportunity-5 minute walk to the Lake! Clean, well-maintained multifamily property featuring 8 total units with separate utilities. Each unit includes central A/C. Property offers private, dedicated parking for tenants. Prime location—just minutes from major hospitals, large employers, shopping, and public transit. High-demand rental area with strong occupancy history. Ideal for investors seeking turnkey income with upside potential. Great long-term hold in a desirable neighborhood.


58 Photos
BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
$1,500,000
6 BD | 5 BA
Residential - Single Family

A remarkable turn-of-the-century Colonial where timeless architecture, meticulous care, and gracious proportions come together beautifully. Set against a backdrop of sweeping Berkshire views, the home captures a sense of elegance and permanence rarely found today. Rich in character yet beautifully suited to modern living, this is a home that feels as extraordinary as its setting. and cutting-edge modern comfort. Designed for both entertaining and intimate family life, this c1930, 6800 sq. ft., Colonial Revival offers 6-bdrms & 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal dining room with its magnificent shell-carved cove, to original cabinetry with rare wood inlays, hand-carved bookshelves, a classic butler's pantry, multiple stately


73 Photos
STONE HOUSE PROPERTIES, LLC
$1,525,000
5 BD | 5 BA
Residential - Single Family

Nestled on 7.79 private mountaintop acres, this distinguished 1916 Italianate Berkshire Cottage sparkles with original architectural details, beautiful fireplaces throughout, and a stunning reflection pool surrounded by mature gardens. Four spacious bedrooms include a luxurious primary suite with sitting room, while the grand great hall creates perfect spaces for both intimate gatherings and gracious entertaining. The lower level features an elegant one-bedroom guest apartment plus a separate catering kitchen, utility rooms and two one car garages, while the main house enjoys lovely terraces facing south, east and west. Surrounded by 200 protected acres near world-class Tanglewood - your own slice of paradise where old-world charm meets mountain-top serenity!


8 Photos
SKYTOP ASSET MANAGEMENT
$1,725,000
15 BD | 15 BA
Multi-Family

68-80 Union Street presents a rare opportunity to acquire a stabilized, fully renovated 15-unit multifamily property in the heart of Pittsfield, Massachusetts. The property delivers strong in-place cash flow at a 7.52 cap rate with meaningful embedded upside through below-market rents and two ready-to-lease vacant units. Every unit has been comprehensively renovated: kitchens include new cabinetry, countertops, and stainless steel appliances; updated bathrooms with modern vanities and new flooring; refinished hardwood floors; and fresh paint throughout. The property is turn-key. The unit mix consists of 10 two-bedroom/one-bath and 5 one-bedroom/one-bath units on a 0.39-acre parcel with on-site paved, striped parking. The property is not located in a FEMA 100-year flood hazard zone.


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SKYTOP ASSET MANAGEMENT
$1,900,000

Commercial


48 Photos
Lamacchia Realty, Inc. - Dalton
$1,950,000

Commercial

Welcome to the historic Wyandotte Woolen Mills in Pittsfield, MA. This woolen mill operated from 1824 to 1963 in the Berkshires and was one of the oldest woolen manufacturing mills in Western Massachusetts. Currently, the complex is home to 14 businesses engaged in production, distribution, flex, & storage space. The property spans 14.79 acres, including both sides of the river, and comprises 15 buildings with a total of 228,611 sq. ft. of space. 14 overhead doors, 11 loading docks, 3 freight elevators & 10' to 16' high ceilings. The area adjacent to the property is zoned for multifamily housing, making it ideal for residential development with the necessary permits and approvals. The turn-of-the-century construction features chestnut beams and maple and concrete flooring throughout.


8 Photos
BERKSHIRE BUSINESS PROPERTIES
$1,990,000

Commercial

44.43 acre parcel adjacent to BJs Club on busy Hubbard Ave. High traffic in this commercial/industrial area. Property is zoned for most any use, as it is IG zone, General Industrial. This would be an excellent place to locate a large cannabis operation, commercial store, business, or multiple smaller shops. Property also is adjacent to Downing III within the Downing Industrial Park.


11 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$2,100,000

Commercial

The subject property is a single story office use building that contains 14,440 square feet. Built in 1998, the property is on a slab on grade founda-tion with a decorative block and metal sided exte-rior; there are fixed framed windows and a pitched metal roof. The building has three 10 foot by 10 foot overhead doors and one, 14 foot by 10 foot overhead doors at ground level. The over-head doors are located at the rear of the building; this area is accessible through a fenced in portion of the site that is utilized by the anchor tenant for vehicle and equipment storage ,Spectrum. The interior is divided into two tenant occupied units. Pittsfield Community Television occupies 4,608 square feet of updated office type space and utilizes it as a television studio and office space. This unit


67 Photos
KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$2,800,000
8 BD | 6 BA
Residential - Single Family

A Landmark Berkshire Estate of Extraordinary Provenance, the Oliver Wendell Holmes summer cottage. Set on 15 private acres in the heart of the Berkshires, a rare American legacy estate commissioned in 1847 as the summer residence of renowned physician, poet, & author Oliver Wendell Holmes Sr. Two centuries later, this extraordinary property remains a testament to architectural elegance, literary heritage, & timeless craftsmanship. The offering preserves original hardwood floors, intricate millwork, & the grandeur of a distinguished era. Its storied halls welcomed literary icons including Longfellow, Melville, & Hawthorne. Surrounded by exceptional privacy, Holmesdale is more than a residence, it is an irreplaceable American landmark


69 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$2,850,000

Commercial

Rare opportunity to acquire a four-building industrial complex totaling approximately 193,037 SF in a centrally located Pittsfield industrial corridor. The property consists of Building A (57,755 SF), Building B (18,125 SF), Building C (59,313 SF), and Building D (57,844 SF), offering a variety of configurations suitable for manufacturing, warehousing, distribution, and industrial users. The main building has 32 offices and conference spaces, plus at least 15 additional spaces throughout the warehouse. Buildings are fully sprinklered and feature clear heights ranging from 8'-30'. The site benefits from two truck-access entrances, providing efficient circulation and logistics capabilities. Building D offers potential for a separate parking area.

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