South Lee, MA Homes for Sale

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  /41

  $4,850,000

  • 13 Beds
  • 13.5 Baths
  • 9,510 Sq Ft

  2 Kemble St, Lenox, MA 01240

  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

  Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX

  2 Kemble St, Lenox, MA 01240
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  /2

  $211,000

  • 3 Beds
  • 2 Baths
  • 1,923 Sq Ft

  47 Lake St, Pittsfield, MA 01201

  Duplex Investment Property!

  Lisa Kelley MACCARO REAL ESTATE

  47 Lake St, Pittsfield, MA 01201
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  /27

  $215,900

  $9K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,532 Sq Ft

  132 Daniels Ave, Pittsfield, MA 01201

  This 3-bedroom, 2-bath home is a great starter opportunity. The flexible layout includes a convenient first-floor bedroom with two additional bedrooms upstairs. The living room and dining room have been freshly painted and feature new vinyl flooring. A spacious kitchen offers plenty of room for cooking and gathering. Outside, enjoy a fenced-in backyard and a detached one-car garage for added

  Jim Thurston Lamacchia Realty, Inc. - Dalton

  132 Daniels Ave, Pittsfield, MA 01201
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  /30

  $795,000

  • 3 Beds
  • 3 Baths
  • 2,218 Sq Ft

  200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262

  Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. The sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms

  Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

  200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262
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  /13

  $259,900

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,672 Sq Ft

  29 Westminster St, Pittsfield, MA 01201

  Income-producing two-family ranch with one vacant unit and one occupied unit, offering an excellent opportunity for both owner-occupants and investors looking to expand their portfolio. The occupied unit is supported by Section 8 assistance, providing reliable rental income. Each mirrored unit features 2 bedrooms and 1 full bathroom with functional, well-designed layouts. The vacant unit has been

  Matthew Keller KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  29 Westminster St, Pittsfield, MA 01201
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  /48

  $294,900

  • 3 Beds
  • 1 Bath
  • 1,282 Sq Ft

  61 Harding St, Pittsfield, MA 01201

  Charming, Move-In Ready Side Hall Colonial - A True ''Dollhouse!''Welcome home to this absolutely stunning, meticulously maintained side hall colonial nestled in a super quiet, peaceful neighborhood. Combining classic charm with a long list of modern, high-ticket upgrades, this home is the definition of a turnkey property and is ready for its next chapter. Step inside to find a warm and

  Stacy Chojnowski WILLIAM PITT SOTHEBY'S - LENOX

  61 Harding St, Pittsfield, MA 01201
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  /28

  $279,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,140 Sq Ft

  74 Holmes Rd, Lenox, MA 01240

  Charming Cape in Lenox! Spacious eat in kitchen with access to a screened porch and large deck overlooking the private backyard, living room with wood flooring, quaint dining area, mudroom that connects to the garage, first floor bedroom and full bath. Second level has two bedrooms and finished family room in lower level walkout. Property has had several improvements made within the last 15 years

  Cortney Dupont COHEN & WHITE ASSOCIATES

  74 Holmes Rd, Lenox, MA 01240
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  /40

  $399,900

  • 4 Beds
  • 3 Baths
  • 2,170 Sq Ft

  118 Winesap Rd, Pittsfield, MA 01201

  Opportunity awaits in this spacious 4-bedroom, 3-bath Colonial located in the highly sought-after Orchard neighborhood. Offering generous room sizes throughout, this home features a welcoming family room with a fireplace and skylights that fill the space with natural light. The convenient first-floor laundry enhances everyday living. The partially finished basement provides additional flexible

  Robin Moore 413 REAL ESTATE

  118 Winesap Rd, Pittsfield, MA 01201
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  /50

  $2,100,000

  $290K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 7,894 Sq Ft

  500 Williams St, Pittsfield, MA 01201

  Own a Living Masterpiece. Meticulously curated by the current stewards since 2006. This Colonial Revival offers rare fusion of 18th-century authenticity and cutting-edge modern comfort. Designed for both grand-scale entertaining and intimate family life, this c1930, 7,894 sq. ft., Colonial Revival offers 6-bdrms & 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  500 Williams St, Pittsfield, MA 01201
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  /25

  $1,450,000

  • 20 Beds
  • 18 Baths
  • 8,653 Sq Ft

  162 Woodlawn Ave, Pittsfield, MA 01201

  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

  Michael Bradley Horvath & Tremblay

  162 Woodlawn Ave, Pittsfield, MA 01201
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  /26

  $1,400,000

  • Land
  • 14.6 Acres
  • $95,890 per Acre

  286 Lee Rd, Lenox, MA 01240

  A once-in-a-lifetime opportunity to build your dream home on a large waterfront parcel in Lenox. This spectacular 14-acre property offers privacy, tranquility, and direct frontage on beautiful Laurel Lake while remaining just minutes from downtown Lenox, Tanglewood, shopping, dining, and all the Berkshires has to offer. Enter through the stone and metal electric gate, cross the stone bridge, and

  Katie Soules WILLIAM RAVEIS - BERKSHIRE

  286 Lee Rd, Lenox, MA 01240
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  /29

  $299,000

  • 2 Beds
  • 3 Baths
  • 1,552 Sq Ft

  5 Rolling Hills Unit 4, Lenox, MA 01240

  Move right into this beautifully updated, light-filled condo offering the perfect blend of comfort and elevated style. Featuring an open floor plan, tall ceilings, and a beautiful renovated kitchen with newer appliances, this home is designed for effortless living and entertaining. Enjoy flexible bonus space in the finished lower level--ideal for a cozy lounge, home office, or guest retreat, plus

  Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

  5 Rolling Hills Unit 4, Lenox, MA 01240
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  /5

  $385,900

  • Land
  • 15.91 Acres
  • $24,255 per Acre

  2 New Lenox Rd, Lenox, MA 01240

  Opportunity Knocks! Expansive Lenox parcel - currently 2 approved building lots (1.0 acre and 14.91 acres) w/ frontage on East Street and New Lenox Road. Seller has a proposed subdivision that would make it 4 lots (1.0 acre, 3.5 acres, 7.59 acres & 2.98 acres). Build your dream home or take advantage of this unbeatable development opportunity in highly sought after location! Water, sewer & gas on

  Sean Taylor MORESI REAL ESTATE PARTNERS

  2 New Lenox Rd, Lenox, MA 01240
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  /24

  $12,000

  • 2 Beds
  • 1 Bath
  • 1,032 Sq Ft

  33 Saint Anns Ave, Lenox, MA 01240

  Experience the ultimate August in Lenox! This lovely cottage is available to rent from August 1 - September 2, offering a prime location just steps from Main Street and minutes to Tanglewood. Inside, enjoy a light-filled spaces and cozy proportions. This 2-bed, 1-bath retreat features a first-floor bedroom, bathroom, and washer/dryer. The second bedroom is a loft space. Relax on the deck, grill,

  John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  33 Saint Anns Ave, Lenox, MA 01240
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  /42

  $158,000

  • 3 Beds
  • 1.5 Baths
  • 3,450 Sq Ft

  334 Columbus Ave, Pittsfield, MA 01201

  A unique opportunity to own a work/live space. The building consists of an updated 3 bedroom house with kitchen, dining, and living room. The ''shop'' space has heat and a separate bathroom. It also boasts a detached two car garage with power. There are endless possibilities with this property. Bring your ideas and let them flow!

  Michele Purcell Lamacchia Realty, Inc.

  334 Columbus Ave, Pittsfield, MA 01201
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  /28

  $270,000

  • 3 Beds
  • 1 Bath
  • 1,188 Sq Ft

  580 Elm St, Pittsfield, MA 01201

  Welcome home to this three-bedroom, one-bath ranch conveniently located in Pittsfield offering the perfect blend of comfort and convenience. Separate dining area, open to living room with a cozy fireplace and a large picture window. This home offers one-level living and a functional layout perfect for everyday easy living. With a little cosmetic updating, this property presents a fantastic

  Darcy Reid MOCKINGBIRD REAL ESTATE

  580 Elm St, Pittsfield, MA 01201
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  /23

  $89,500

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  405 Pittsfield Rd Unit Lot F2, Lenox, MA 01240

  Totally renovated and move-in ready mobile home in Lenox! This 2-bedroom home is located on a quiet dead-end street in the Berkshire Mobile Park and offers a nice deck along with an ample side yard to enjoy. Shed in the back needs some repairs to the roof.

  Tanya Shepardson Lamacchia Realty, Inc. - Dalton

  405 Pittsfield Rd Unit Lot F2, Lenox, MA 01240
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  /6

  $65,000

  • 12 Beds
  • 5 Baths
  • 4,032 Sq Ft

  48 Brown St, Pittsfield, MA 01201

  Opportunity knocks! This 4-family property has suffered significant fire damage and is being sold as-is for land value. Ideal tear down project with endless redevelopment potential. The lot includes a detached garage and offers ample space for new construction. Bring your vision and rebuild in a growing area with strong rental demand. Cash or construction financing only. All offers considered.

  Xavier Cruz Fathom Realty

  48 Brown St, Pittsfield, MA 01201
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  /48

  $269,000

  • 3 Beds
  • 2 Baths
  • 1,628 Sq Ft

  34 Holmes Rd, Pittsfield, MA 01201

  Move right into this charming and spacious Colonial located in desirable Southeast Pittsfield. This well-maintained home features beautiful hardwood floors, high ceilings, original moldings, and generously sized rooms throughout.The first floor offers a bright and inviting living room, formal dining room, a large kitchen with a spacious pantry, main-level laundry, a full bathroom, and two

  Jose Larios Lamacchia Realty, Inc. - Dalton

  34 Holmes Rd, Pittsfield, MA 01201
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  /33

  $365,000

  $14K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,727 Sq Ft

  39 Bartlett Ave, Pittsfield, MA 01201

  Introducing 39-41 Bartlett Avenue, a classic three-family Victorian in the heart of Pittsfield, offering a fantastic investment opportunity. This fully occupied property provides immediate income potential and features separate natural gas utilities for each unit. The home boasts vinyl siding and replacement windows, combining classic charm with practical updates. Ideally situated just moments

  Jessica Rizzo Lamacchia Realty, Inc. - Dalton

  39 Bartlett Ave, Pittsfield, MA 01201
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  /45

  $329,000

  • 6 Beds
  • 2 Baths
  • 2,592 Sq Ft

  78 Harvard St, Pittsfield, MA 01201

  Enjoy this move-in ready and meticulously maintained two-family home in the heart of Pittsfield. Featuring two spacious side-by-side units, this property offers an excellent opportunity for both owner-occupants and investors alike. Enjoy efficient natural gas heating systems, updated hot water heaters, and a beautifully rebuilt front porch that adds timeless curb appeal.Inside, you'll find

  Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

  78 Harvard St, Pittsfield, MA 01201
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  /21

  $350,000

  • 3 Beds
  • 2 Baths
  • 3,038 Sq Ft

  137 Housatonic St, Lenox, MA 01240

  HOME BEING SOLD AS IS NO NEGOTIATION ON INSPECTION ISSUES. THE PRICE IS NOT NEGOTIABLE. Two family minutes from downtown Lenox. First floor unit has 2 bedrooms with spacious living area and kitchen. Upstairs unit is a 1 bedroom, 1 bath with fireplace and back deck. Roof replaced in 2021, natural gas, town water and sewer.

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  137 Housatonic St, Lenox, MA 01240
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  /27

  $674,000

  • 4 Beds
  • 4 Baths
  • 1,843 Sq Ft

  28 Evergreen Trail Unit 28, Lenox, MA 01240

  Custom-designed Lenox Woods townhome with direct access to Kennedy Park! This beautifully maintained, one-owner residence offers 4 bedrooms, 3.5 baths, and an exceptional blend of comfort, quality, and convenience.Thoughtfully upgraded throughout, the open-concept main level features a stunning kitchen with custom cabinetry, granite countertops, tile flooring, stainless steel appliances, a

  Heather Gallagher STONE HOUSE PROPERTIES, LLC

  28 Evergreen Trail Unit 28, Lenox, MA 01240
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  /27

  $309,000

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft

  34 Hungerford St, Pittsfield, MA 01201

  Welcome to this beautifully built new construction home offering the perfect blend of style, efficiency, and comfort. Featuring 2 spacious bedrooms and 1.5 bathrooms, this thoughtfully designed home boasts an open-concept layout with bright natural light, modern finishes, and quality craftsmanship throughout. The main living area flows seamlessly into the kitchen and dining space, creating an

  Ahliya Phillips KELLER WILLIAMS REALTY

  34 Hungerford St, Pittsfield, MA 01201
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  /42

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,720 Sq Ft

  100 Essex St, Pittsfield, MA 01201

  *Video tour and floor plans availableThis lovely colonial home features two separate units, as it has been designed to offer an in-law apartment. The property has been tastefully renovated with new kitchens with quartz countertops, gorgeous updated bathrooms, fresh interior and interior paint, refinished gleaming hardwood floors, and other improvements, that include new roof, updated electrical

  Maria Liccardi Kempf-Vanderburgh Realty Consultants, Inc.

  100 Essex St, Pittsfield, MA 01201
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  /28

  $1,150,000

  $100K PRICE DROP

  • 14 Beds
  • 14 Baths
  • 9,928 Sq Ft

  40 Reed St, Pittsfield, MA 01201

  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.

  Cory Evangelisto NOCHER REALTY

  40 Reed St, Pittsfield, MA 01201
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  /45

  $489,900

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  359 New Lenox Rd, Lenox, MA 01240

  Lenox! Don't miss this move-in ready three-bedroom cape. Outdoor enthusiasts will enjoy proximity to October Mt state forest - miles of trails for hiking, mountain biking, x-country skiing! Canoe or kayak up the road at the Decker boat launch! Inside this meticulously maintained charmer you'll find open floor plan with fireplaced living room, dining, updated kitchen, two first-floor bedrooms and

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  359 New Lenox Rd, Lenox, MA 01240
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  /21

  $399,900

  $50K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  18 Lawton St, Lenox, MA 01240

  A rare and unique opportunity awaits just minutes from downtown Lenox! This charming Cape style home offers the perfect blend of country privacy and town convenience. Enjoy picturesque views and the tranquil sounds of a seasonal brook right from your back deck. The home features new windows, an oversized two car garage currently being used as a workshop, and is a fantastic canvas for your vision.

  Tiffany Roberts TIFFANY ROBERTS PROPERTIES LLC

  18 Lawton St, Lenox, MA 01240
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  /30

  $299,000

  • 2 Beds
  • 2 Baths
  • 1,624 Sq Ft

  3 Rolling Hills Unit 2, Lenox, MA 01240

  Beautifully maintained 2 bedroom, 2 bath condo, both bedrooms/ baths on main level with covered deck & beautiful views, finished lower level w/ laundry offers whole other level of space for office, hobbies, etc. Enjoy the clubhouse (gym, pool table, hot tub, sauna, kitchen/entertainment rm, local art hangings) out door POOL, TENNIS COURTS, walking TRAILS, community GARDENS, kayak storage, fenced

  Donna DiGrigoli DIGRIGOLI REAL ESTATE

  3 Rolling Hills Unit 2, Lenox, MA 01240
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  /31

  $274,900

  $25K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,184 Sq Ft

  142 Benedict Rd, Pittsfield, MA 01201

  Well-maintained 1930 Colonial that has been cared for by its longtime owners for decades. This home features three spacious bedrooms, hardwood floors, abundant natural sunlight, and a functional layout with comfortable living spaces throughout, including a formal dining room. The front entrance offers a spacious enclosed porch, providing additional living or sitting space. The kitchen includes a

  Tracy Munger KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  142 Benedict Rd, Pittsfield, MA 01201
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  /40

  $214,900

  • 2 Beds
  • 1 Bath
  • 1,028 Sq Ft

  33 Maplewood Ave Unit 103, Pittsfield, MA 01201

  If you are looking for easy one-level living - don't miss this opportunity! The Maplewood is an elegant condo conversion consisting of eighteen units centrally located in downtown Pittsfield. You'll enjoy this light-filled corner/end unit on the first floor. High ceilings and an open-living plan give a very spacious feel to this two-bedroom unit. Kitchen with granite and stainless, hardwood

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  33 Maplewood Ave Unit 103, Pittsfield, MA 01201
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  /15

  $49,500

  • Land
  • 10,890 Sq Ft
  • $198,000 per Acre

  0 Parker St, Pittsfield, MA 01201

  Well-located and cleared corner lot with existing curb cuts on both Parker Street and Kellogg Street. The +/-0.25-acre parcel is zoned RM, with water, sewer, and natural gas available at the street. Its proximity to Berkshire Health Systems--the region's largest employer - along with walkability to Tyler Street businesses and public transportation, makes this an excellent opportunity for

  Conor Meehan STONE HOUSE PROPERTIES, LLC

  0 Parker St, Pittsfield, MA 01201
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  /35

  $254,900

  $15K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,360 Sq Ft

  85 Edward Ave, Pittsfield, MA 01201

  This cherished family home is ready for it's next chapter. A welcoming front foyer opens to a spacious living room filled with natural light and featuring a classic wood-burning fireplace, seamlessly connected to a formal dining room ideal for entertaining. Beautiful hardwood floors, along with original wood molding and trim throughout add timeless character and warmth. The second floor offers

  Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

  85 Edward Ave, Pittsfield, MA 01201
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  /11

  $245,000

  • Land
  • 9.13 Acres
  • $26,835 per Acre

  1570 B Washington Mountain Rd, Washington, MA 01223

  Outlook at October Mountain - This special parcel with exceptional views is located in a private enclave of well crafted homes planned for privacy. Live the rural life but still have the option to be only a short distance from everything that makes the Berkshires special; theatre, film, music, boutiques and shopping. With completed septic design in place, electric and telephone available all you

  Mary Jane White COHEN & WHITE ASSOCIATES

  1570 B Washington Mountain Rd, Washington, MA 01223
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  /35

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  15 Lillian St, Pittsfield, MA 01201

  Welcome home to this sweet split-level in desirable Southeast Pittsfield neighborhood. Offering 3 bedrooms and 1.5 baths, this well-maintained home features a spacious, well-appointed kitchen with granite countertops, abundant cabinetry, and great functionality for everyday living. Cozy up by the wood-burning fireplace or unwind in the inviting four-season room overlooking the deck and backyard.

  Victoria Standring Lamacchia Realty, Inc. - Dalton

  15 Lillian St, Pittsfield, MA 01201
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  /37

  $630,000

  $50K PRICE DROP

  • 8 Beds
  • 8 Baths
  • 6,120 Sq Ft

  301 Fenn St, Pittsfield, MA 01201

  8 Unit investment opportunity! Located just outside of downtown Pittsfield and within walking distance to shops, restaurants, schools, and parks. Low maintenance exterior with loads of off street parking. All units feature one bedroom/studio setups with separate heat and electricity. Coin-op laundry located on site for additional income.

  Cory Evangelisto NOCHER REALTY

  301 Fenn St, Pittsfield, MA 01201
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  /7

  $219,900

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  233 Cadwell Rd, Pittsfield, MA 01201

  Two-family home set on just under 1.5 acres offering the perfect blend of country living and city convenience. Each unit features decks overlooking a spacious backyard, ideal for relaxing or entertaining. Enjoy the privacy and open space while still being just minutes from city amenities, shopping, and dining. A great opportunity for owner-occupants or investors--live in one unit and rent the

  Denise DeSellier Berkshire Hathaway HomeServices Realty Professionals

  233 Cadwell Rd, Pittsfield, MA 01201
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  /35

  $179,900

  • 3 Beds
  • 1 Bath
  • 890 Sq Ft

  22 S Atlantic Ave, Pittsfield, MA 01201

  Welcome to this updated & affordable home in the heart of Pittsfield. Offering 3 bedrooms, including a convenient first-floor bedroom; a renovated bathroom, & an updated eat-in kitchen, this home blends comfort, flexibility, and everyday functionality. First-floor laundry adds to the ease of living, & with the updates already completed, you can move right in with confidence. Outside, you'll

  Jessie Downer Lamacchia Realty, Inc. - Dalton

  22 S Atlantic Ave, Pittsfield, MA 01201
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  /88

  $3,250,000

  • 4 Beds
  • 4 Baths
  • 5,696 Sq Ft

  7 Wheatley Dr, Stockbridge, MA 01262

  A house that stops people mid-sentence! At the Lenox/Stockbridge line on the western shore of Lily Pond, discover this one-of-a-kind home. A rare architectural sanctuary where nature, privacy, and imagination quietly redefine Berkshire living. Embraced by woods and water, this 4br, 4ba contemporary is bathed in extraordinary light. Enter and you'll find over 5000 sf. living space. Bedrooms are

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  7 Wheatley Dr, Stockbridge, MA 01262
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  /62

  $1,279,000

  • 4 Beds
  • 4.5 Baths
  • 2,691 Sq Ft

  18 Highcrest Rd, Lenox, MA 01240

  Condo at Twelve Oaks Village. End of Cul-de-sac with Mountain views. This unit offers lots of Privacy being an end unit. Come enjoy Tennis Swimming pool and Fitness center all on property. 3 Full floors of living space with Primary Suite/Walk in Closet on 1st floor. Spacious open floor plan to enjoy entertaining with plenty of outdoor space with screened in porch and private deck. Enjoy Easterly

  Suzann Ward HOUSATONIC REAL ESTATE

  18 Highcrest Rd, Lenox, MA 01240

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