Homes for Sale near Hillcrest Academy

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  /27

  $255,000

  • 3 Beds
  • 1 Bath
  • 888 Sq Ft

  157 Maple Grove Dr, Pittsfield, MA 01201

  Welcome to easy, one-level living in this 3-bedroom ranch, nestled in the sought-after southeast section of Pittsfield. The property features vinyl siding, modern appliances, and on-demand hot water. Outside you will find a fully fenced-in yard ideal for relaxing or entertaining. Enjoy summer days on the expansive deck or take a dip in the above-ground pool. Two storage sheds provide space for

  Jessica Rizzo LAMACCHIA REALTY, INC

  157 Maple Grove Dr, Pittsfield, MA 01201
• 

  

  

  /30

  $339,900

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

  185 Lenox Ave, Pittsfield, MA 01201

  OPEN HOUSE Sat 05/31/25 10:00am - 11:30am. Welcome home to this immaculate and beautifully maintained 3-bedroom, 1.5-bath Colonial, located less than one mile from Berkshire Medical Center. This move-in ready gem offers a perfect blend of classic charm and modern updates throughout. Step inside through the inviting tiled foyer and discover a spacious layout featuring hardwood floors and a large

  Cindy Carrigan LAMACCHIA REALTY, INC

  185 Lenox Ave, Pittsfield, MA 01201
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  /55

  $5,499,500

  • 8 Beds
  • 6.5 Baths
  • 6,986 Sq Ft

  140 Hancock Rd, Pittsfield, MA 01201

  Welcome to an extraordinary opportunity on the shores of Pontoosuc Lake. This remarkable estate sets a new standard for lakefront living in Pittsfield and beyond, offering a rare combination of luxury, scale, and setting.With over 18,700 square feet of total space, including an impressive amount of garage space suitable for car collectors or hobbyists, this home provides room to live, relax, and

  Cameron Volastro STONE HOUSE PROPERTIES, LLC

  140 Hancock Rd, Pittsfield, MA 01201
• 

  

  

  /45

  $569,777

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft

  31 Saint Ann's Ave, Lenox, MA 01240

  Beautifully located near downtown Lenox!The Claude and Louise Delahaye House is tucked away on peaceful St. Ann's Ave, just steps from the iconic St. Ann's Church!Lenox's shops, dining, and cultural attractions are just a stroll away!Inside, 1,700 sq ft of tastefully updated living space blends preserved period details with modern touches. OWN - Instead of Renting - this Tanglewood Season! A

  Audrey Matys BERKSHIRE LISTINGS

  31 Saint Ann's Ave, Lenox, MA 01240
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  /22

  $349,000

  • 3 Beds
  • 1 Bath
  • 1,986 Sq Ft

  349 New Lenox Rd, Lenox, MA 01240

  Spacious 3 Bed/1 Bath Colonial located in a quiet Lenox neighborhood. This charming home offers: gleaming hardwood floors, an oversized family room which could be used as a 1st floor primary, a new Refrigerator & Stove, Washer & Dryer hook ups on the 1st floor, attached garage, steam heat and plenty of light throughout! Savor the beautiful Berkshires, while you lounge in your expansive flat

  Timothy Johnson NOCHER REALTY

  349 New Lenox Rd, Lenox, MA 01240
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  /52

  $730,000

  • 5 Beds
  • 4.5 Baths
  • 3,381 Sq Ft

  33 Alpine Trail, Pittsfield, MA 01201

  Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The main level boasts vaulted ceilings with open bright common areas, great room with wood flooring and gas fireplace, updated kitchen, dining room with views, primary bedroom with newly renovated en suite bath, oversized garage, half bathroom and private screened porch and deck to take in the fresh air and

  Cortney Dupont COHEN & WHITE ASSOCIATES

  33 Alpine Trail, Pittsfield, MA 01201
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  /12

  $12,900

  • Land
  • 0.46 Acre
  • $28,096 per Acre

  0 Longview Terrace, Pittsfield, MA 01201

  Waterfront Lot! This lightly wooded untouched lot in a quiet well established neighborhood has frontage on Goodrich Pond. Electric, water, sewer and cable are all availible at road. Seller's have no knowledge if this lot is buildable.

  Timothy Johnson NOCHER REALTY

  0 Longview Terrace, Pittsfield, MA 01201
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  /6

  $290,000

  • 4 Beds
  • 2 Baths
  • 1,986 Sq Ft

  249 Pittsfield Rd, Lenox, MA 01240

  Opportunity knocks in the Berkshires! COMMERCIALLY & RESIDENTIALLY ZONED. This 3-acre gem on scenic Route 7 in Lenox offers a rare blend of space, potential, and prime location. Nestled among mature trees and open land, the property features a 1,986 sq ft farmhouse-style home waiting to be restored to its former glory. With residential and commercial zoning, two curb cuts, and access to natural

  Reciprocal Reciprocal Berkshire Reciprocal

  249 Pittsfield Rd, Lenox, MA 01240
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  /29

  $625,000

  • 4 Beds
  • 3.5 Baths
  • 3,296 Sq Ft

  14 Alpine Trail Unit 14, Pittsfield, MA 01201

  Welcome to your dream mountain retreat! This stunning end unit in a community of 96 units offers an unparalleled lifestyle for outdoor enthusiasts. With effortless access to ski trails right from your back screened-in porch, you can hit the slopes at Bousquet Mountain anytime you desire.Spanning over 3,200 square feet, this 4-bedroom, 3.5-bath condo has a spacious three-level layout. Step inside

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  14 Alpine Trail Unit 14, Pittsfield, MA 01201
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  /5

  $179,900

  • 6 Beds
  • 2 Baths
  • 2,376 Sq Ft

  24 Glenwood Ave, Pittsfield, MA 01201

  For sale an approximately 2,376 SF two-family home with a 2-car garage on approximately 0.227 acres of land. The Property is located in close proximity to the center of Pittsfield with easy access to Rts. 7, 8, 8A, 9 & 20.

  John Dill Colebrook Realty Services, Inc.

  24 Glenwood Ave, Pittsfield, MA 01201
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  /30

  $380,000

  • 5 Beds
  • 2.5 Baths
  • 3,030 Sq Ft

  145 Bartlett Ave, Pittsfield, MA 01201

  Welcome to this stunning Colonial home, perfectly situated near the vibrant heart of downtown Pittsfield. With 5 spacious bedrooms and 3 bathrooms, this 3030 square foot detached home offers ample space for both relaxation and entertaining. The hardwood flooring throughout the house adds a touch of elegance and warmth. Enjoy hosting gatherings on the large deck, or take a short stroll to the

  Jarrett Hernandez 360BERKSHIRE REALTY GROUP

  145 Bartlett Ave, Pittsfield, MA 01201
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  /50

  $4,985,000

  • 13 Beds
  • 13.5 Baths
  • 9,556 Sq Ft

  2 Kemble St, Lenox, MA 01240

  The Kemble, a registered ''Great Estate'' built in 1881 is located in the heart of the thriving downtown Lenox business district. This classic Colonial Revival building has recently been refreshed with modern furnishings and decor, repurposed as a luxury rental property, and is being offered as a turn key operation. With grand gathering spaces, a well equipped kitchen, handsome mahogany bar, and

  Cameron Volastro STONE HOUSE PROPERTIES, LLC

  2 Kemble St, Lenox, MA 01240
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  /33

  $1,500,000

  • 7 Beds
  • 7.5 Baths
  • 4,000 Sq Ft

  802 State Rd, Richmond, MA 01254

  Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare blend of colonial charm and modern equestrian excellence. Spanning 11+ bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence, three enchanting cottages, and the potential to include the region's premier full-service equestrian facility (see

  Diana Bisselle William Pitt Sotheby's Int'l

  802 State Rd, Richmond, MA 01254
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  /33

  $337,000

  • 3 Beds
  • 1 Bath
  • 1,575 Sq Ft

  4 Paula Ave, Pittsfield, MA 01201

  Adorable Southeast Ranch Located in a Desirable Neighborhood! This Charming 3-Bedroom, 1-Bath Home sits on a Sunny Corner Lot w/Southern Exposure. Features Include a 1-Car Garage & Close Proximity to Williams Elem. School. Enjoy Outdoor Living with Newer Front & Side Decks, Stone Patio & Firepit, 3 year old Storage Shed 10x12, Addt'l Updates Include Newer Gutters, Roof Approx. 16 yrs old, Vinyl

  Kim Gordnier RE/MAX COMPASS

  4 Paula Ave, Pittsfield, MA 01201
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  /2

  $30,000

  • Land
  • 1.08 Acres
  • $27,778 per Acre

  36 Old Farm Ln, Pittsfield, MA 01201

  Located at 36 Old Farm Lane in Pittsfield, MA, this land investment offers a prime opportunity for development or a place to build your dream HOME. Situated in a quiet residential area, the property provides easy access to local amenities, schools, and major roads. With generous acreage, it presents various possibilities for residential or recreational use. Pittsfield’s real estate market is on

  Mg Group Century 21 North East

  36 Old Farm Ln, Pittsfield, MA 01201
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  /54

  $939,000

  • 5 Beds
  • 4.5 Baths
  • 3,700 Sq Ft

  127 Alpine Trail, Pittsfield, MA 01201

  This unit is absolutely stunning! It has breathtaking views of the mountains and spacious open common areas filled with natural light. The main Great room has soaring ceilings, a cozy gas fireplace, wood floors, and direct access to your private screened porch and deck. The kitchen, dining area, and first-floor primary en-suite are all open and inviting. Additionally, there is a main level

  Cortney Dupont COHEN & WHITE ASSOCIATES

  127 Alpine Trail, Pittsfield, MA 01201
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  /16

  $200,000

  • 6 Beds
  • 2 Baths
  • 1,680 Sq Ft

  138 Robbins Ave, Pittsfield, MA 01201

  One unit is vacant & the other unit rented for $1,800/month, presenting a great opportunity for investors and owner-occupants! This income producing multifamily home is set back from the street and offers two apartments, each one with 3 bedrooms /1 Bath, laundry hookups and its own Lead Paint Compliance Certificate. The first floor unit has a beautifully renovated bathroom. The apartment was

  Maria Liccardi LAMACCHIA REALTY, INC

  138 Robbins Ave, Pittsfield, MA 01201
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  /7

  $49,900

  • Land
  • 0.25 Acre
  • $199,600 per Acre

  0 Onota St, Pittsfield, MA 01201

  Parcel ID: G100018202This 0.251 acre buildable lot is located just minutes to Onota and Pontoosuc lake! It is located next to two family home. The street consists of a mix of single family and multifamily homes. City water and sewer and natural gas at the street.*Additional adjacent lot also available, MLS 73357620

  Maria Liccardi Lamacchia Realty, Inc.

  0 Onota St, Pittsfield, MA 01201
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  /33

  $379,000

  • 4 Beds
  • 1.5 Baths
  • 2,926 Sq Ft

  92 Elm St, Pittsfield, MA 01201

  This significantly improved building is located in a highly desirable, high-traffic area, offering both visibility and convenience. Featuring low-maintenance vinyl siding and ramp access, this property is fully equipped to meet a variety of business needs. The building is heated with natural gas, offering efficiency and comfort. The third-floor finished attic provides additional flexible space

  Katie Soules WILLIAM RAVEIS REAL ESTATE

  92 Elm St, Pittsfield, MA 01201
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  /53

  $359,000

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  659 Pecks Rd, Pittsfield, MA 01201

  Charming 3-Bedroom Cape Near the LakeWelcome to your perfect summer retreat! This lovely 3-bedroom Cape-style home is nestled just a short stroll from the lake, offering the ideal blend of comfort, charm, and convenience. Step inside to find a cozy, light-filled interior with classic Cape character and modern updates throughout.Outside, a beautiful stone patio invites you to relax and unwind.

  Michele Purcell LAMACCHIA REALTY, INC

  659 Pecks Rd, Pittsfield, MA 01201
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  /10

  $59,900

  • Land
  • 3.10 Acres
  • $19,323 per Acre

  0 Eastbrook Ln, Pittsfield, MA 01201

  **Build Your Dream Home in the Exclusive Woodmonte Community!**Welcome to this DOUBLE Lot # 148-9 Eastbrook Lane, located in the prestigious and private Woodmonte neighborhood in Pittsfield, MA. This secluded double lot, listed at $59,900, is a rare find--completely prepped, fully serviced, and ideal for building your dream home!Enjoy the convenience of immediate ''Plug & Play'' construction,

  Nathan Girard ROYAL PROPERTY GROUP

  0 Eastbrook Ln, Pittsfield, MA 01201
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  /6

  $71,500

  • Land
  • 0.29 Acre
  • $246,560 per Acre

  0 Faucett Ln, Pittsfield, MA 01201

  Build your dream home in one of Pittsfield's most desirable neighborhoods. This .29-acre lot offers a rare combination of privacy and community, backing up to Association Land--so you'll never have neighbors behind you. Enjoy a quiet, residential setting with nearby access to parks, golf courses, and the country club. This is a great opportunity to build in a well-established area that offers

  Cameron Volastro STONE HOUSE PROPERTIES, LLC

  0 Faucett Ln, Pittsfield, MA 01201
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  /5

  $385,900

  • Land
  • 16 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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  /80

  $1,189,900

  • 5 Beds
  • 2.5 Baths
  • 3,087 Sq Ft

  18 Old Farm Ln, Pittsfield, MA 01201

  New Incredible Offer: Seller to pay HOA Fees for 3 Years at closing! Seller offers extra lot for a total of 3 Lots (buyers choice) & Paint Concession $50,000 for Finishing touches! See this Like New -New England Farmhouse ready for you! Over the bridge into the woods escape to a magical setting amidst a woodland preserve of 3+ acres. Build a family compound of your own with 2 extra

  Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

  18 Old Farm Ln, Pittsfield, MA 01201
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  /30

  $559,900

  • 4 Beds
  • 2 Baths
  • 1,858 Sq Ft

  178 New Lenox Rd, Lenox, MA 01240

  Move-in ready Lenox 4 bed 2 full bath with mountain views on 1 acre. 3 full bedrooms upstairs, 1st floor study/ 4th bedroom. Large screened back porch and front 3- season room. Town water and sewer, natural gas heat and see-through wild-life fence protects huge backyard. Recent updates - new roof, gutters, exterior paint, new front porch entrance and back stairs, refurbished 3 season room, sealed

  Sean Taylor MORESI REAL ESTATE PARTNERS

  178 New Lenox Rd, Lenox, MA 01240
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  /9

  $589,000

  • Land
  • 21 Acres
  • $28,222 per Acre

  0 East St, Lenox, MA 01240

  This stunning 20+ acre building lot in Lenox, with frontage on East and Housatonic St. is the perfect place to build your dream home. The gently sloping land leads up towards westerly sunsets, while offering distant views of October Mountain to the east. With its peaceful and private setting, imagine waking up every day to the stunning views from your new home, surrounded by the serene natural

  Gary Johnston STONE HOUSE PROPERTIES, LLC

  0 East St, Lenox, MA 01240
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  /31

  $619,900

  • 4 Beds
  • 2.5 Baths
  • 2,464 Sq Ft

  4 Filomena Dr, Pittsfield, MA 01201

  Beautifully updated 4 bed, 3 bath Colonial in southeast Pittsfield. Inside boasts a bright, open floor plan with new stainless steel appliances and a fully finished basement offering additional square footage.Outside offers a serene wooded vista, with a year round brook, enjoyed from the updated composite deck and stone patio. Abutted by an expansive network of walking/biking trails, the natural

  Joseph Jennings SIGNATURE ASSOCIATES

  4 Filomena Dr, Pittsfield, MA 01201
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  /24

  $265,000

  • 3 Beds
  • 1 Bath
  • 1,224 Sq Ft

  326 Dalton Ave, Pittsfield, MA 01201

  PRICE PERFECTED @ $265,000 Affordable and Adorable! 3-bedroom, 1-bathroom cape-style home with a detached one-car garage, perfectly situated on Dalton Ave. This charming property features a convenient first-floor bedroom, full bathroom, and laundry. Enjoy spacious bedrooms, a formal dining room, a cozy fireplace, and a mudroom with pantry and laundry. Beautiful hardwood floors throughout most of

  Jessie Downer LAMACCHIA REALTY, INC

  326 Dalton Ave, Pittsfield, MA 01201
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  /26

  $229,500

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft

  26 Crosier Ave, Pittsfield, MA 01201

  Welcome to 26 Crosier Ave--charming character meets creative opportunity!Nestled in the heart of Pittsfield, this delightful colonial-style home offers a bright, spacious layout that's brimming with classic charm! With 3 bedrooms and 2 baths, cozy living room, a functional kitchen, and generously sized rooms filled with natural light. The unfinished third-level space whispers ''potential,'' while

  Marci Levesque BISHOP WEST REAL ESTATE

  26 Crosier Ave, Pittsfield, MA 01201
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  /18

  $799,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  15 Cherry Hill Dr Unit Lot 12, Pittsfield, MA 01201

  Looking to have your new home in the new year? This Berkshire Country Meadows single-level living condo will be ready for summer 2025 occupancy! Construction is well underway for this 2000sf, 3 bedroom, 2 bath stand-alone condo, but there is still time to make your own personalized selections! Central a/c, natural gas heat, gas fireplace, hardwood floors, two car garage. The condo

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  15 Cherry Hill Dr Unit Lot 12, Pittsfield, MA 01201
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  /20

  $799,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  5 Aspen Way, Pittsfield, MA 01201

  Great opportunity to custom design your 2000 square foot free-standing condo home at Berkshire Country Meadows! This is one of only a few remaining sites in this established community. Close to Pontoosuc Lake and centrally located for all Berkshire attractions. Association has a club house with fitness equipment, pool and tennis. Select from several floor plans which feature a contemporary

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  5 Aspen Way, Pittsfield, MA 01201
• 

  

  /20

  $799,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  5 Aspen Way Unit 17, Pittsfield, MA 01201

  Great opportunity to custom design your 2000 square foot free-standing condo home at Berkshire Country Meadows! This is one of only a few remaining sites in this established community. Close to Pontoosuc Lake and centrally located for all Berkshire attractions. Association has a club house with fitness equipment, pool and tennis. Select from several floor plans which feature a contemporary

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  5 Aspen Way Unit 17, Pittsfield, MA 01201
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  /73

  $2,895,000

  • 7 Beds
  • 9 Baths
  • 6,578 Sq Ft

  813 East St, Lenox, MA 01240

  Don't miss seeing the beautiful renovation just completed on this lovely Lenox Contemporary on almost 5A of privacy...enjoy incredible outdoor living spaces including an in-ground Gunite pool, Pavilion with outdoor kitchen and pool house with living space, kitchen, outdoor and indoor showers and even an outdoor TV! A real STAYCATION! The main house boasts lovely common spaces in the open floor

  Mary Jo Piretti PIRETTI REAL ESTATE

  813 East St, Lenox, MA 01240
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  /20

  $499,000

  • Land
  • 16 Acres
  • $31,188 per Acre

  407 Churchill St, Pittsfield, MA 01201

  Imagine building your dream home or family compound on this stunning estate parcel in the heart of the Berkshires. This very rare gated land package includes a total of three parcels, each with power and wells in place. The main building site is at the top of the property and includes a four bedroom septic and buried propane tank. Conveniently located just minutes from Pittsfield State Forest

  Victoria Standring LAMACCHIA REALTY, INC

  407 Churchill St, Pittsfield, MA 01201
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  /33

  $199,900

  • 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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  /13

  $119,900

  • Land
  • 6 Acres
  • $21,800 per Acre

  Lot 3,4,5 Lynda Ct, Pittsfield, MA 01201

  Step onto this land that has a country feel but is located within the city of Pittsfield. Onota lake is walking distance. The lot is 3 lots being sold as 1. It is lot #3, #4 and #5. Electric and water at the end of lot #3.

  Janet Benoit MOCKINGBIRD REAL ESTATE

  Lot 3,4,5 Lynda Ct, Pittsfield, MA 01201
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  /18

  $199,900

  • 4 Beds
  • 2 Baths
  • 1,480 Sq Ft

  51 Adam St, Pittsfield, MA 01201

  2 family flat featuring 2br, 1 bth each apartment, enclosed front porch on downstairs and off street parking.One apartment vacant for easy showing and move in ready. new Flooring being updated for upstairs unit.

  Scott Higuera 413 REAL ESTATE

  51 Adam St, Pittsfield, MA 01201
• 

  

  /4

  $279,900

  • 6 Beds
  • 2 Baths
  • 2,736 Sq Ft

  29 Glenwood Ave, Pittsfield, MA 01201

  Spacious duplex with 3bed 1 bath on each side. Each side has a walk up attic and laundry hook ups.Plenty of off street parking.

  Scott Higuera 413 REAL ESTATE

  29 Glenwood Ave, Pittsfield, MA 01201
• 

  

  /92

  $724,000

  • 4 Beds
  • 5 Baths
  • 2,748 Sq Ft

  10 Lillybrook Rd, Pittsfield, MA 01201

  Beautiful 4 bedroom contemporary on Lilybrook Road. Vaulted entry way leads to living (sitting) room flanked by formal dining room. Also on the first floor is oversized great (family) room with fireplace, large eat-in kitchen and private master (in-law) suite with full bath and jet tub. The second floor has another master suite with full private bath, two additional bedrooms, and a second full

  Paul Clark CLARK REALTY GROUP LLC

  10 Lillybrook Rd, Pittsfield, MA 01201
• 

  

  /27

  $154,900

  • Land
  • 9 Acres
  • $16,438 per Acre

  LOT 301 Cascade St, Pittsfield, MA 01201

  Here is the lot you have been waiting for! Located in a private and bucolic setting of West Pittsfield. A rare opportunity to have the privacy and benefits of living in nature but access to city amenities. This parcel is only a six minute drive to Onota Lake; one of the premier lakes in the county for boating and fishing. There has been a clearing made for a home site and a drilled well. ~3 hours

  Derek Strzepa NOCHER REALTY

  LOT 301 Cascade St, Pittsfield, MA 01201

Showing Results 121 - 160, Page 4 of 5