Lanesboro, MA Homes for Sale

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  $1,900

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft

  55 Crystal St Unit 4, Lenox, MA 01240

  Spacious first-floor one-bedroom, one-bath apartment at 55 Crystal St in Lenoxdale. This unit features a large open-concept living, dining, and kitchen area with plenty of natural light and stainless steel appliances. The generously sized bedroom offers ample closet space, and the full bathroom includes a tub/shower. Heat is included in the rent, helping keep monthly expenses predictable. The

  Christian Garner NOCHER REALTY

  55 Crystal St Unit 4, Lenox, MA 01240
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  /49

  $365,000

  Open Sat 1PM - 2:30PM

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft

  136 Cadwell Rd, Pittsfield, MA 01201

  Well-updated split-level ranch offering plenty of space inside and out! Updated kitchen features granite countertops, newer cabinetry, tile flooring and stainless appliances. Hardwood floors flow through much of the main level. The primary bedroom offers a slider to the elevated 10x42 wood deck overlooking the fenced backyard. Main-level full bath features a double vanity and tiled tub/shower.

  Aimee Kelly eXp REALTY

  136 Cadwell Rd, Pittsfield, MA 01201
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  $685,000

  • 3 Beds
  • 2.5 Baths
  • 1,620 Sq Ft

  200 Old Stockbridge Rd Unit VA-6, Stockbridge, MA 01262

  STUNNING VIEWS for as far as you can see from this modern unit located in Winden Hills Vanna building. Open common spaces washed in natural light; Great room with scenic views, fireplace and built ins, kitchen with charm and character open to dining. Primary w/en suite full bath, two guest bedrooms and additional one and half baths. This unit comes with access to the elevator for convenience, a

  Cortney Dupont COHEN & WHITE ASSOCIATES

  200 Old Stockbridge Rd Unit VA-6, Stockbridge, MA 01262
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  $449,000

  $40K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,457 Sq Ft

  181 New Lenox Rd, Lenox, MA 01240

  Enchanting Lenox Cottage minutes to Tanglewood- 2 Bedroom / 2 Full Bath RetreatThe bright, airy living room features warm wood floors that lead into a cozy eat-in kitchen. With a heated sunporch & 1st floor full bath, the home offers multiple inviting spaces to relax or entertain. Step outside to a brand-new back deck, an ideal setting for summer evenings. 2 Bedrooms on second floor, with

  Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  181 New Lenox Rd, Lenox, MA 01240
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  $2,800,000

  • 8 Beds
  • 5.5 Baths
  • 6,761 Sq Ft

  497 Holmes Rd, Pittsfield, MA 01201

  A Landmark Berkshire Estate of Extraordinary Provenance. 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

  Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  497 Holmes Rd, Pittsfield, MA 01201
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  $334,900

  $15K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,088 Sq Ft

  112 Gamwell Ave, Pittsfield, MA 01201

  First time ever offered! Single Level Living Surrounded by Gardens You'll Fall in Love With Lovingly maintained by the original builder's family, this cherished ranch is ready for it's next chapter. Recently refinished hardwood floors, a fireplace, and a sun filled four season room with French doors overlooking established perennial gardens create a warm and inviting atmosphere. Years of

  Stacy Hebb NOCHER REALTY

  112 Gamwell Ave, Pittsfield, MA 01201
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  /49

  $479,000

  $16K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,855 Sq Ft

  70 Rockland Dr, Pittsfield, MA 01201

  Beautifully maintained 4-bedroom, 2.5-bath Colonial set on a quarter acre lot with privacy and curb appeal. Enjoy a spacious floor plan featurning a wood-burning fireplace, natural gas heat & hot water and newer replacement windows throughout, including new living room windows in 6/2026. The primary suite offers his-and-hers closets and a private bath. The finished lower level adds valuable

  Darcy Reid MOCKINGBIRD REAL ESTATE

  70 Rockland Dr, Pittsfield, MA 01201
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  /23

  $209,900

  $10K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 866 Sq Ft

  139 2nd St, Pittsfield, MA 01201

  The home just passed an FHA appraisal and appraised over the asking price! This renovated home offers two bedrooms and two bathrooms. The first floor features an enclosed front porch, living room, foyer, full bathroom, laundry room and updated kitchen with new quartz countertops and stainless appliances. Upstairs you will find two bedrooms and half bathroom. Both of the bathrooms have been

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  139 2nd St, Pittsfield, MA 01201
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  /53

  $679,900

  • 4 Beds
  • 3.5 Baths
  • 2,682 Sq Ft

  16 Juliana Dr, Pittsfield, MA 01201

  Welcome to this spacious and beautifully renovated 4 bedroom home in desirable Southeast neighborhood. With 3 full bathrooms and 1 half bath, this home provides plenty of room for family and guests. The open floor plan creates an inviting flow between the generously sized living spaces, while the renovated interior offers a fresh, modern feel. The impressive primary suite features a walk-in

  Robin Moore 413 REAL ESTATE

  16 Juliana Dr, Pittsfield, MA 01201
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  /19

  $649,900

  • Land
  • 3.67 Acres
  • $177,084 per Acre

  37 Elm St, Pittsfield, MA 01201

  Prime downtown opportunity! Almost 4 acres ready for your development ideas. One of Pittsfield's last remaining sites large enough for drive thru permit.Ther front of the property is BG, the back is CWS. Very versatile site on one of Pittsfield's finest streets.

  Steve Ray 413 REAL ESTATE

  37 Elm St, Pittsfield, MA 01201
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  /5

  $235,000

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,947 Sq Ft

  15 Noble Ave, Pittsfield, MA 01201

  Two family duplex just outside of downtown. Featuring two bedrooms and one bathroom in each unit with hardwood floors. Off Street parking and separate utilities. Please reach out for interior photos.

  Cory Evangelisto NOCHER REALTY

  15 Noble Ave, Pittsfield, MA 01201
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  $595,000

  • 3 Beds
  • 2 Baths
  • 2,217 Sq Ft

  139 Mountain Dr, Pittsfield, MA 01201

  Situated on highly desirable Mountain Drive, this expanded 3-bedroom, 2-bath Cape delivers classic Berkshire charm, thoughtful updates, and flexible living spaces. Step inside from the welcoming front porch into an inviting layout featuring hardwood floors and abundant natural light. The spacious living room is anchored by a wood-burning fireplace flanked by custom built-ins, flowing into the

  Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  139 Mountain Dr, Pittsfield, MA 01201
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  $419,900

  • 3 Beds
  • 4 Baths
  • 2,269 Sq Ft

  1112 South St, Dalton, MA 01226

  If space, flexibility, & a great backyard are on your wish list, this home is one to see! Thoughtfully expanded over the years, the home offers a versatile layout with generously sized bedrooms on both the first and second floors, four bathrooms, and plenty of bonus space. The back addition is especially inviting, featuring a large living room and dining room with plenty of space to gather.

  Jessie Downer Lamacchia Realty, Inc. - Dalton

  1112 South St, Dalton, MA 01226
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  $289,900

  Open Sat 10AM - 11:30AM $30K PRICE DROP Pre-Foreclosure

  • 3 Beds
  • 1.5 Baths
  • 1,566 Sq Ft

  73 Plymouth St, Pittsfield, MA 01201

  OPEN HOUSE Saturday, the 29th, from 10:00am - 11:30am. Recently off market for needed maintenance on the exterior siding and landscaping, this home is now a must-see! Colonial style home is bright and airy featuring windows that invite abundant natural sunlight into every room. The main level offers a easy flow between the inviting living spaces and a convenient half-bath, while the second floor

  Jason Nocher NOCHER REALTY

  73 Plymouth St, Pittsfield, MA 01201
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  /20

  $185,000

  • 2 Beds
  • 1.5 Baths
  • 1,506 Sq Ft

  7 Lincoln St, Pittsfield, MA 01201

  ''The Castle'' on Lincoln! Distinctive architecture and generous living spaces give this home incredible potential. The striking stone exterior, curved bay windows, second-floor balcony, hardwood floors, and vintage details create character that's hard to find. The spacious interior offers a flexible layout with an open connection between the living, dining, and kitchen areas. The second bedroom

  Jonathan Vella Lamacchia Realty, Inc. - Dalton

  7 Lincoln St, Pittsfield, MA 01201
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  $3,925,000

  • 8 Beds
  • 8.5 Baths
  • 6,000 Sq Ft

  17 Main St, Lenox, MA 01240

  Extraordinary opportunity to own a showcase of New England history and hospitality--17 Main Street, a masterfully restored Berkshire cottage in the vibrant heart of downtown Lenox. Originally built in 1883 and once owned by Gilded Age shipping magnate John Schermerhorn, this landmark property blends historic grandeur with modern comfort. Between 2021 and 2025, the residence underwent a

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  17 Main St, Lenox, MA 01240
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  /21

  $339,900

  • 4 Beds
  • 1.5 Baths
  • 1,488 Sq Ft

  1981 East St, Pittsfield, MA 01201

  MOVE IN READY! Charming 4-bedroom, 1½-bath Cape in Southeast Pittsfield, located in Williams Elementary School district! This well-maintained home features beautiful hardwood floors, natural gas heat, a first-floor bedroom and walk-in shower, abundant storage, and a partially finished basement ideal for a family room, home office, or home gym. Enjoy the rare bonus of an included rear lot,

  Anthony Riello Lamacchia Realty, Inc. - Dalton

  1981 East St, Pittsfield, MA 01201
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  $207,000

  $22K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 902 Sq Ft

  1 Colt Rd Unit 1, Pittsfield, MA 01201

  Welcome to easy, in-town living at sought-after One Colt Road in a charming neighborhood. This first-floor condominium offers the perfect blend of convenience and comfort, just a short stroll to Berkshire Museum, Colonial Theatre, local restaurants, and boutique shops. Featuring 2 bedrooms and 1 bath, the layout is both functional and inviting. A rare screened porch extends your living space,

  Victoria Standring Lamacchia Realty, Inc. - Dalton

  1 Colt Rd Unit 1, Pittsfield, MA 01201
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  $575,000

  $25K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,600 Sq Ft

  24 Brunell Ave, Lenox, MA 01240

  Location, location, location! Ideally situated within easy walking distance of the village, elementary school, and Tanglewood, this charming ranch offers comfortable single-level living in a quiet, desirable neighborhood. The large, level and semi-private backyard provides plenty of room to relax, entertain, garden, or enjoy the above-ground pool. Inside, the home features a spacious open living

  Melissa Dimassimo STONE HOUSE PROPERTIES, LLC

  24 Brunell Ave, Lenox, MA 01240
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  /21

  $79,900

  • 3 Beds
  • 2 Baths
  • 1,463 Sq Ft

  79 Dewey Ave, Pittsfield, MA 01201

  Opportunity awaits! A mature apple tree greets you at the entrance, setting the tone for this spacious older home full of untapped potential. The property offers generous living space with room to reimagine the layout to suit your vision. Set on an approximate quarter acre lot, the yard provides plenty of room to garden, expand, or simply enjoy some outdoor space of your own. This home requires

  Renee Lander BISHOP WEST REAL ESTATE

  79 Dewey Ave, Pittsfield, MA 01201
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  /28

  $299,900

  • 3 Beds
  • 1 Bath
  • 942 Sq Ft

  21 Austin Ave, Pittsfield, MA 01201

  Welcome to this beautifully renovated 3-bedroom ranch, perfectly situated on a quiet dead-end street in Southeast. This move-in-ready home features a brand-new roof, new windows, new flooring throughout, and a completely updated kitchen and bathroom. The thoughtful renovations offer a fresh, modern feel while maintaining the comfortable layout and easy living of a classic ranch. Outside, enjoy a

  Robin Moore 413 REAL ESTATE

  21 Austin Ave, Pittsfield, MA 01201
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  /3

  $898,000

  • Land
  • 12.84 Acres
  • $69,938 per Acre

  21 Dan Fox Dr, Pittsfield, MA 01201

  12.84 Acres of Prime development Land. Ideal for possible Commercial and/or Residential projects. Close to Shopping and Transportation. Curb cut and some engineering done.

  Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  21 Dan Fox Dr, Pittsfield, MA 01201
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  /50

  $749,000

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  360 Housatonic St, Lenox, MA 01240

  Lenox MA Colonial on 0.92 acres with 4 bedrooms, 2.5 baths, and 2,184 sq ft of well maintained living space. This move in ready Berkshire home features a spacious eat-in kitchen, formal dining room, bright living room with wood floors, and a screened porch overlooking the yard. Enjoy outdoor living with two decks, a paver patio with BBQ area, and beautiful perennial gardens. Upstairs offers four

  Samantha Homeyer BIRCH PROPERTIES

  360 Housatonic St, Lenox, MA 01240
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  $645,000

  $30K PRICE DROP

  • 6 Beds
  • 3 Baths
  • 4,832 Sq Ft

  1 Eaton Ln, Pittsfield, MA 01201

  Elegance Meets History on 1 Eaton Lane!Tucked away on a quiet, sought-after street just minutes from the Country Club of Pittsfield & only 10 minutes to vibrant downtown Lenox, this remarkable Colonial seamlessly blends timeless character with extraordinary versatility. Offering just under 5,000 square feet of living space, this historic estate presents a rare opportunity for those seeking a

  Stacy Chojnowski WILLIAM PITT SOTHEBY'S - LENOX

  1 Eaton Ln, Pittsfield, MA 01201
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  /43

  $749,900

  • 3 Beds
  • 3 Baths
  • 3,159 Sq Ft

  208 Karen Dr, Pittsfield, MA 01201

  Charming open-concept Ranch INCLUDES A SEPARATE ABUTTING BUILDING LOT in the heart of the Berkshires on a quiet non-through street! This beautiful, move-in ready Ranch offers 1,959 sq ft of bright, inviting living space on the main level. Finished 1200 sq ft basement with a full bath adds extra space, perfect for a game room or holiday gatherings. The dining area connects to a large kitchen with

  Susan Calkins STONE HOUSE PROPERTIES, LLC

  208 Karen Dr, Pittsfield, MA 01201
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  /10

  $320,000

  $5K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,378 Sq Ft

  89 Robbins Ave, Pittsfield, MA 01201

  Great Two family with some updates. Hardwood floor in dining room and bedrooms. Kitchen and bathroom with Ceramic floor. Newer Roof. Parking off street for 4 cars

  Al DeSouza First Option Properties Inc.

  89 Robbins Ave, Pittsfield, MA 01201
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  $239,900

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  78 Ontario St, Pittsfield, MA 01201

  Cape-style 3-bedroom, 1-bath home in a coveted Southeast Pittsfield location directly across from Deming Park and close to coffee shops, restaurants, a pharmacy, convenience stores, and other Elm Street amenities. Features include newer windows, a newer roof, new carpeting upstairs, and a recently renovated bath. The interior offers an opportunity for additional cosmetic updates and

  Marc Bellora Lamacchia Realty, Inc. - Dalton

  78 Ontario St, Pittsfield, MA 01201
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  /2

  $69,000

  • Land
  • 3.3 Acres
  • $20,909 per Acre

  75 Woodland Rd, Lee, MA 01238

  Over 3 acres of wooded land on Woodland Road in Lee near October Mountain State Forest. Previously used for logging, this parcel features a wooded, sloping landscape. Convenient to downtown Lee & Lenox and easy access to the Massachusetts Turnpike. Additional pastoral 1 acre parcel available at 60 Woodland Rd., may be purchased together or separately. Buyers and buyer's agents to perform their

  Lisa Kelley MACCARO REAL ESTATE

  75 Woodland Rd, Lee, MA 01238
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  /20

  $259,900

  $30K PRICE DROP

  • 8 Beds
  • 2 Baths
  • 2,016 Sq Ft

  42 John St, Pittsfield, MA 01201

  Investment Opportunity with Owner-Occupant Potential! This well-maintained two-family home offers spacious 3-4 bedroom apartments in each unit, making it an excellent opportunity for investors or buyers looking to offset their mortgage with rental income. One unit is currently vacant, allowing for immediate occupancy or the ability to secure a new tenant at current market rents. The occupied unit

  Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  42 John St, Pittsfield, MA 01201
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  $625,000

  $25K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 3,524 Sq Ft

  15 Kenilworth St, Pittsfield, MA 01201

  Beautifully tucked away in one of Pittsfield's most established neighborhoods, this stately 5-bedroom, 5-bath home is a rare offering filled with warmth, character, and endless potential. From its gracious proportions to its timeless architectural details, this is a home that makes a lasting impression.Sun-filled living spaces, generously sized rooms, and a thoughtful layout provide the

  Heather Gallagher STONE HOUSE PROPERTIES, LLC

  15 Kenilworth St, Pittsfield, MA 01201
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  $269,900

  • 5 Beds
  • 2 Baths
  • 2,100 Sq Ft

  12 Lincoln St, Pittsfield, MA 01201

  Lovely five bedroom two bath Colonial on 5500+ sq.ft. of land.Lots of space, front porch for relaxing on beautiful summer evenings. Two bedrooms on the first floor and three bedrooms on the second floor with a deck off the bedroom and off the kitchen on the first floor. Two driveways for plenty of parking!!!Three sheds on property for storage will stay. Or not.

  Theresa Adams Dacey Realty, LLC

  12 Lincoln St, Pittsfield, MA 01201
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  /25

  $284,900

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,327 Sq Ft

  48 Plastics Ave, Pittsfield, MA 01201

  Renovated 3-Bedroom Cape in a Central Location. Welcome home to this newly renovated 3-bedroom Cape-style house, ideally situated in a convenient central location close to everyday amenities, local services, shopping, dining, and commuter routes. Combining classic Cape charm with fresh modern updates, this inviting home offers comfort, functionality, and move-in-ready appeal. Property highlights

  Dawn Vadnais MORESI REAL ESTATE PARTNERS

  48 Plastics Ave, Pittsfield, MA 01201
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  /21

  $249,000

  • 2 Beds
  • 1 Bath
  • 1,144 Sq Ft

  21 Terrace Ave, Pittsfield, MA 01201

  Welcome to this cozy and well-maintained 2-bedroom, 1-bath Colonial, offering classic charm and a warm, inviting feel. A welcoming front porch, cute backyard, and meticulously landscaped grounds add to the home's wonderful curb appeal.Inside, the home has been lovingly cared for and is in very good condition, with a few cosmetic updates offering an opportunity to bring it into your preferred

  Tracy Munger KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  21 Terrace Ave, Pittsfield, MA 01201
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  /30

  $279,900

  Open Sat 11AM - 1PM

  • 5 Beds
  • 2 Baths
  • 1,933 Sq Ft

  77 Onota St, Pittsfield, MA 01201

  Step into the timeless elegance of this turn-of-the-century Victorian, where historic charm and modern comfort come together beautifully. Original architectural details create a warm and inviting atmosphere throughout, including soaring 9-foot ceilings, intricate crown molding, gleaming hardwood floors, and beautifully crafted built-ins. Spacious, light-filled rooms offer plenty of room to

  Audrey Matys BERKSHIRE LISTINGS

  77 Onota St, Pittsfield, MA 01201
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  $249,900

  $15K PRICE DROP

  • 6 Beds
  • 3 Baths
  • 3,510 Sq Ft

  32 Westminister St, Pittsfield, MA 01201

  Calling all investors and hands-on owner-occupants! This 3-unit multi-family offers 15 rooms, 6 bedrooms, and 3 full baths across 3,510 sq ft on a 0.17-acre lot. The owner has already made key updates, including some new flooring, fresh paint, updated electric, and a new bulkhead, giving you a head start on renovations. Still needed: updated heating systems, roof work, wall patching, and final

  The Ponte Group Keller Williams South Watuppa

  32 Westminister St, Pittsfield, MA 01201
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  $485,000

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

  500 Walker St, Lenox, MA 01242

  Envision waking up in this beautifully renovated New England farmhouse in quaint Lenoxdale Village. Enjoy morning sunrises on the front patio and quiet evening dinners on the terrace, all just minutes from the world-class culture of Tanglewood and the iconic downtowns of Lenox and Stockbridge. Inside, original hardwood floors flow throughout a versatile layout featuring 3-4 bedrooms, a cozy

  Tony Segalla WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  500 Walker St, Lenox, MA 01242
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  /32

  $369,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  880 East St Unit 10C, Lee, MA 01238

  Immaculate unit in move-in condition. 1st floor bedroom and a 1st floor stall shower with glass door. Hugh 3 season room with glass and screens to enjoy the Berkshire air. Hardwood floors in living and dining area. Upscale stainless steel refrigerator and Bosch Dishwasher. Two bedrooms and full bath with tub/shower upstairs. Unfinished lower level with work bench, brand new washer and (older)

  Susan Baum BERKSHIRE HOMES AND CONDOS

  880 East St Unit 10C, Lee, MA 01238
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  /27

  $269,900

  $25K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,386 Sq Ft

  141 Dewey Ave, Pittsfield, MA 01201

  This 2 family flat is ready for it's new owner or someone looking for rental income. Both units have been remodeled with new kitchens, baths, flooring and fresh paint. Both units have enclosed porches. There is a large oversized commercial garage in the back that's perfect for storage, additional rental income. Easy walk up to the downtown area.

  Janet Benoit MOCKINGBIRD REAL ESTATE

  141 Dewey Ave, Pittsfield, MA 01201

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