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Currently listing 1283 sales properties. |
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40 Photos BISHOP WEST REAL ESTATE |
$429,900
3 BD |
1 BA
Residential - Single Family Well-maintained & move-in ready with historic charm, exceptional acreage, and endless possibilities. Set on approximately 5.2 acres in West Pittsfield's scenic farm country, this 1820s home offers a rare opportunity to enjoy the space & privacy that's increasingly difficult to find at this price point. Inside, you'll find spacious rooms, beautiful hardwood floors, a wide central staircase, fireplace, and a flexible floor plan. Enjoy morning coffee in the bright enclosed porch. Explore the expansive basement showcasing impressive original stonework and abundant storage. Located less than a quarter mile from Fort Hill Farm and just minutes from shopping, restaurants, and schools. The perfect balance of convenience, character, and privacy. |
38 Photos NON-MEMBER / RECIPROCAL |
$419,000
8 BD |
4 BA
Multi-Family Presenting a distinguished multi-family property located at 53 Orchard St, Pittsfield, MA.. This expansive 4 unit spans 2688 square feet of living area, offering a rare opportunity for sophisticated urban living or a strategic investment. This property includes six generously proportioned bedrooms, providing ample private accommodations across its two stories. The property's substantial lot size of 4160 square feet provides a significant footprint within the urban landscape. We invite you to discover the potential and unique character of this Pittsfield address. Three Units are vacant and recently remodeled with market rents averaging about 1395.00 in the area. One Unit is rented month to month at 950.00. All units are lead certified. |
41 Photos Lamacchia Realty, Inc. - Dalton |
$309,000
3 BD |
2 BA
Residential - Single Family Welcome to this 3-bedroom, 1.5-bath Colonial on Somerset Street in Pittsfield. With 1,200 square feet of living space, this well-loved home has been in the same family for many years and is ready for new owners to make it their own. Inside, you'll find a classic floor plan with warm, inviting spaces perfect for everyday living. Step outside to a generous backyard featuring beautiful mature landscaping--ideal for gardening, relaxing, or entertaining. A two-car garage offers added storage and convenience. Located in a desirable neighborhood close to parks, schools, and downtown amenities, this home is a wonderful opportunity not to be missed. |
37 Photos WILLIAM PITT SOTHEBY'S - GT BARRINGTON |
$549,000
3 BD |
1 BA
Residential - Single Family Have you been dreaming of fun on Stockbridge Bowl? The time is now! Built in 2011, this lovely home is directly across the street from the beloved town beach and affords water views from most windows. Offering 4 seasons of single-level living, 3 BR, 1 full BA, a well appointed kitchen and gracious living spaces. The unfinished walk-out lower level is the perfect place to store your kayaks, and could be finished to offer more living space. There is plenty of off-street parking above and below the home. You are mere moments to Tanglewood's Lions Gate and the very best of the Berkshires. Would make a great rental, or a wonderful family retreat to make memories for years to come. Town sewer, private well, radiant heat, and energy efficient construction, all in a location that can't be be beat! |
68 Photos COMPASS MASSACHUSETTS , LLC GB |
$735,000
4 BD |
3 BA
Residential - Single Family Spacious 4-bedroom, 2.5-bath Southeast Pittsfield Colonial on over half an acre blends classic charm with thoughtful updates and is truly move-in ready. The kitchen opens to a screened-in porch and flows into a generous dining room with built-in shelving. The light-filled living room centers around a wood-burning fireplace creating a warm gathering space. The second floor offers four bedrooms, two full bathrooms, a large cedar closet, and ample storage throughout. The large fenced backyard with professional landscaping offers exceptional outdoor living. Major updates include a new roof, central air, furnace, replaced sewer line, newer appliances, and freshly painted exterior. A two-car garage and partially finished basement round out the package. |
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54 Photos BISHOP WEST REAL ESTATE |
$565,000
3 BD |
3 BA
Residential - Single Family Set on an expansive 21.6-acre private landscape, This 3bed, 2.5-bath home blends comfort, space & versatility. The main level offers a warm, open layout with a bright living area, a functional kitchen, and easy flow to the outdoor spaces, perfect for everyday living or entertaining. The 3 bedrooms, including a comfortable primary suite, provide plenty of room to unwind. A standout feature of this property is the walk-out basement, offering exceptional flexibility. Downstairs you'll find 3 bonus rooms ideal for home office, guest space, or hobby rooms, along with a full bath, creating a great setup for multi-generational living or expanded recreational use. Outside, the acreage delivers privacy, wooded surroundings, whether you envision trails, gardens, or simply enjoying peaceful setting! |
46 Photos COHEN & WHITE ASSOCIATES |
$1,550,000
3 BD |
3 BA
Residential - Single Family This Stockbridge home has it all...privacy, protected view, river frontage, plenty of room for all washed with natural light and location, location, location!! Down a town maintained country lane, this special property welcomes you to this spacious home with living rm, great room w/fp, den/office, open kitchen/dining w/wall of glass leading to the wonderful screened porch & spacious decking, mud room off 2 car garage, laundry & half bath complete the main level. Upper level has generous primary en suite with balcony overlooking the serene yard and two guest bedrooms and bath. Centrally located for easy access to restaurants, theater, shopping, museums, skiing, cultural venues and only ,minutes to the Village of Stockbridge! |
31 Photos COMPASS MASSACHUSETTS , LLC GB |
$2,690,000
4 BD |
3 BA
Residential - Single Family Welcome to 19 Buckingham Lane, a completely turnkey, beautifully curated waterfront retreat designed by internationally acclaimed interior designer Jess Cooney of Jess Cooney Interiors. Offered fully furnished, this newly renovated home sits directly on the shores of Lake Garfield and features four bedrooms and three baths across three levels. Soft earth tones, richly textured wood finishes on floors, walls and ceilings, and elegant stone surfaces create a relaxed yet sophisticated atmosphere for lakefront living. Tucked into a private cove, it offers exceptional peace and seclusion while the expansive deck provides the perfect setting for entertaining with sweeping water views. And if you don't own a boat, you're in luck--one is included with the sale. |
36 Photos THE KINDERHOOK GROUP |
$430,000
4 BD |
2 BA
Residential - Single Family Move in ready! New roof and gutters in 2026, maintains original details but has been thoroughly updated. Located on a quiet, tree lined street, 81 Northumberland offers the kind of lifestyle one dreams about. Imagine walking your children to the nearby elementary school, stopping in for fresh pastries at the local bakery, grabbing a coffee on the way home, or enjoying an evening stroll through the established Southeast neighborhood. With a warm, inviting home and everyday conveniences just minutes away, this is more than a place to live - it's a place to build lasting memories. |
50 Photos COMPASS MASSACHUSETTS , LLC GB |
$1,350,000
4 BD |
4 BA
Residential - Single Family Set on 22 private acres, this Monterey retreat offers a peaceful escape from city and suburban life. Freshly painted this spring, it's near Lake Garfield and Monterey Town Beach, and across from Beartown State Forest. The bright, expansive home features four ensuite bedrooms, including a spacious primary suite, large entertaining areas, and cathedral & vaulted ceilings. Outdoors, enjoy a 16' x 40' heated gunite pool, an outdoor enclosed shower, a large stone patio, and the year-round Loom Brook flowing through the woods. The lower level includes a sauna, exercise pool, and utilities. A two-car garage connects to a mudroom with laundry, half bath, and outdoor shower, plus a large bonus room above. A rare opportunity at this price in scenic, convenient Monterey, with fiber internet. |
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25 Photos REAL BROKER |
$399,000
3 BD |
2 BA
Residential - Single Family Welcome home to this move-in ready Becket ranch, set back from the road on nearly an acre and surrounded by a park-like, fully fenced setting. Designed for easy one-level living, this inviting home offers 3 bedrooms, 2 full baths, gleaming wood floors, and an updated eat-in kitchen with direct access to the back deck, perfect for everyday living and entertaining. Relax on the covered front porch, enjoy the spacious yard, or take advantage of the oversized attached 2-car garage with plenty of room for storage. Conveniently located just minutes from Jacob's Pillow, the Mass Pike, Lee Premium Outlets, and all the Berkshires have to offer. Whether you're looking for a year-round home or a Berkshires getaway, 2305 Jacobs Ladder Road is ready to welcome you home! |
27 Photos STONE HOUSE PROPERTIES, LLC |
$664,500
4 BD |
4 BA
Residential - Condo/Townhouse Fantastic Offer for a Custom-designed & beautifully maintained one-owner residence offers 4 bedrooms, 3.5 baths, in the most desirable location in the verdant Berkshires. Calm & Quiet with direct access to Kennedy Park - you'll enjoy the perfect balance of nature, community & the Arts. Lenox offers quality shops, farmers markets, Botanic Gardens & music. A beautiful open floor plan features a totally upgraded kitchen with gas stone fireplace overlooking the woods. Adjacent screened porch opens to a private paver patio surrounded by native gardens. 1st floor en-suite bedroom provides an ideal 1-level living. Upstairs the spacious primary suite offers double closets, a beautifully appointed bath with quartz countertops, double sinks, generous linen closet, tile tub & shower. |
35 Photos MACCARO REAL ESTATE |
$379,000
3 BD |
1 BA
Residential - Single Family Charming three-bedroom, one full bath ranch offering the ease and convenience of one level living in a highly desirable neighborhood. Situated on a spacious lot, just shy of a half-acre, this home features a large, fenced backyard perfect for entertaining, gardening or simply enjoying the outdoors. Wrap around deck overlooking above ground pool, creating the ideal summer setting. Inside you will find a comfortable eat-in kitchen, front living room, updated bathroom and 3 bedrooms. Partially finished basement that provides additional room for a family room, home office, gym and laundry. Conveniently located close to schools and downtown Lee, ''Gateway to the Berkshires''. |
38 Photos CENTURY 21 NORTHEAST |
$289,000
3 BD |
2 BA
Residential - Single Family Set on private acres in the Berkshires, this one-owner manufactured home, built in 2005, offers the perfect combination of privacy, space, and opportunity. The home features 3 bedrooms and 2 full bathrooms, including a spacious primary suite with a private bath complete with a soaking tub and separate walk-in shower. The functional layout offers comfortable living spaces, while a walk-up attic provides valuable storage. Served by a 420ft drilled well and with a passed Title 5 inspection, this property offers added value and peace of mind. Situated on a slab foundation, enjoy your morning coffee or unwind in the evening from the front porch overlooking the property. Outside, you'll also find an exterior storage shed and a concrete pad with electricity already in place! |
36 Photos WILLIAM PITT SOTHEBY'S - GT BARRINGTON |
$4,150,000
3 BD |
4 BA
Residential - Condo/Townhouse Experience elevated wellness living in this exceptional Canyon Ranch penthouse in Lenox. This 3,300+ sq. ft. residence offers three spacious ensuite bedrooms, a powder room, an expansive great room, a chef's kitchen and three fireplaces that create a warm, inviting atmosphere. A private patio provides the perfect retreat to relax and enjoy the natural beauty of the Berkshires. Ownership includes a requisite annual resort membership with full access to Canyon Ranch's world-renowned wellness amenities. Just minutes from the Berkshires' acclaimed cultural attractions, fine dining and outdoor recreation, this is a rare opportunity to enjoy luxury, wellness and timeless design in one extraordinary home. |
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