Berkshire, MA Homes

/31
$392,000 Sold Jul 23, 2025
- 8,048 Sq Ft
- $49/SF
- 13 Days On Market
- 8 Beds
- 4 Baths
- Built 1990
14 Westminster St, Pittsfield, MA 01201

Here is your opportunity to own this conveniently located, 4-family investment property in Pittsfield! Each spacious apartment consists of 2 bedrooms and 1 bathroom. The property features front and back porch/decks, a large back yard that is partially fenced, natural gas heating and plenty of off-street paved parking. Schedule a viewing today to explore this investment opportunity firsthand and

Nancy Bush Brooks SIGNATURE ASSOCIATES

14 Westminster St, Pittsfield, MA 01201

/30
Est $199,517 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,568 Sq Ft
12 Leidhold Place, Pittsfield, MA 01201

12 Leidhold Place, Pittsfield, MA 01201

/40
$859,000 Under Contract
- 4 Beds
- 3.5 Baths
- 3,800 Sq Ft
1 Pheasant Way, Pittsfield, MA 01201

Luxe Mediterranean-inspired Home in Private Woodmonte EstatesNestled within the exclusive enclave of Woodmonte Estates, this lovely Mediterranean-inspired home (1995) offers a seamless blend of elegance, warmth, and modern convenience. Set against the picturesque backdrop of Pittsfield State Forest, outdoor enthusiasts will delight in direct access to hiking, skiing, and nature trails, making

Selina Lamb

BIRCH PROPERTIES

(413) 848-7907

1 Pheasant Way, Pittsfield, MA 01201
/30
$300,000 Sold Jul 23, 2025
- 1,354 Sq Ft
- $222/SF
- 22 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1957
86 Asci Dr, Pittsfield, MA 01201

Pittsfield - Location, Location, Location!Enjoy the ease of true one-level living in this charming, well-maintained home featuring a one-car attached garage and inviting living room with hardwood floors and a cozy fireplace. With two generously sized bedrooms and a full bath, this home offers comfortable space and functionality. The galley kitchen flows seamlessly into the dining area and

Colleen Zajac MONARCH REALTY, INC.

86 Asci Dr, Pittsfield, MA 01201

/23
Est $257,658 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 2,511 Sq Ft
18 Broad St, Pittsfield, MA 01201

18 Broad St, Pittsfield, MA 01201

/13
$1,399,900 New Construction
- 4 Beds
- 3 Baths
- 3,100 Sq Ft
144 Eastbrook Ln, Pittsfield, MA 01201

Experience the rare chance to bring your ideal living space to life within the prestigious gated community of Woodmonte Estates in Pittsfield, MA. This to-be-built luxury home offers a range of customizable, high-end features, including soaring 9'-18' ceilings, red oak hardwood flooring, gas fireplaces, custom kitchen cabinetry, and a spacious primary suite with a spa-inspired bath. Crafted with

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 666-1014

144 Eastbrook Ln, Pittsfield, MA 01201
/37
$365,000 Sold Jul 23, 2025
- 2,912 Sq Ft
- $125/SF
- 6 Days On Market
- 5 Beds
- 6 Baths
- Built 1924
303 Springside Ave, Pittsfield, MA 01201

If your an investor or looking to owner occupy and have your tenants help pay your mortgage don't look any further. This 3 family and its 5 Garages is in excellent condition. Newer roof and windows, All separate utilities, Newer hot water heaters, laundry hook ups for all units. All tenants have been informed of probable rent increases after sale.

James Gelinas GELINAS REAL ESTATE

303 Springside Ave, Pittsfield, MA 01201

/26
Est $256,422 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,050 Sq Ft
134 Doreen St, Pittsfield, MA 01201

134 Doreen St, Pittsfield, MA 01201

/30
$1,399,900 New Construction
- 4 Beds
- 3 Baths
- 3,100 Sq Ft
8 Northbrook Ln, Pittsfield, MA 01201

Now under rapid construction, this stunning contemporary two-story home sits on a private 2.79-acre cul-de-sac lot. Spanning over 3,100 sq ft, it features soaring 9' ceilings, a dramatic two-story foyer and living room, and a walkout basement with finishing potential. Designed for both comfort and style, the home offers a cozy fireplace in the living room and a second fireplace in the luxurious

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 266-5435

8 Northbrook Ln, Pittsfield, MA 01201
/32
$300,000 Sold Jul 22, 2025
- 1,365 Sq Ft
- $220/SF
- 29 Days On Market
- 3 Beds
- 1 Bath
- Built 1955
35 Deborah Ave, Pittsfield, MA 01201

Your new home awaits! Enjoy this charming ranch style home in the heart of Southeast Pittsfield, situated between Williams Street and Elm Street. Featuring 3 bedrooms, spacious living room with fireplace, an abundance of natural lighting, and original hardwood floors throughout. The home has a new roof, central air conditioning, updated appliances, partially finished basement, & new hot water

Laiken Rapisarda LAMACCHIA REALTY, INC

35 Deborah Ave, Pittsfield, MA 01201

/62
Est $965,769 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,416 Sq Ft
4 Southbrook Ln, Pittsfield, MA 01201

4 Southbrook Ln, Pittsfield, MA 01201

/69
$565,900
- 8 Beds
- 3 Baths
- 4,034 Sq Ft
144 Brombach St, Pittsfield, MA 01201

Beautiful, spacious 8 bedroom, 3 updated bath, 4000+sf home, custom built and nestled between two lakes with incredible views in the heart of the picturesque Berkshire Mountains! Walk to Onota Lake in approximately 9 minutes and enjoy a 5 minute drive to Pontoosuc Lake both suitable for kayaking, fishing, swimming, picnicking and more. Enjoy the convenience of 2 laundry rooms and two updated

Darcy Reid MOCKINGBIRD REAL ESTATE

144 Brombach St, Pittsfield, MA 01201
/40
$325,000 Sold Jul 22, 2025
- 2,008 Sq Ft
- $162/SF
- 59 Days On Market
- 4 Beds
- 2 Baths
- Built 1927
41 New Hampshire Ave, Pittsfield, MA 01201

Virtual tour available!Beautiful 2-family flat with detached two-car garage plus 5 off-street spaces. Each unit offers 2 bedrooms, 1 bath, kitchen, living room, dining room and enclosed back porch. The 1st floor unit was recently renovated! There are separate electric meters, and natural gas heat & hot water for each apartment. The home is on city water and sewer. The basement has exterior

Maria Liccardi LAMACCHIA REALTY, INC

41 New Hampshire Ave, Pittsfield, MA 01201

/11
Est $179,411 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,547 Sq Ft
105 Madison Ave, Pittsfield, MA 01201

105 Madison Ave, Pittsfield, MA 01201

/36
$610,000
- 4 Beds
- 2.5 Baths
- 2,464 Sq Ft
304 Dalton Division Rd, Pittsfield, MA 01201

Welcome to 304 Dalton Division Road in Pittsfield! This charming property blends country living with city access, set on over 6 acres of land offering privacy, outdoor space, and beautifully landscaped grounds. It includes three sheds, one a wood shed, for ample storage. The home features a mudroom, first-floor laundry, and a kitchen with quartz countertops and sliding doors to the backyard. The

Patrick Cathro NON-MEMBER / RECIPROCAL

304 Dalton Division Rd, Pittsfield, MA 01201
/25
$297,900 Sold Jul 21, 2025
- 1,244 Sq Ft
- $239/SF
- 6 Days On Market
- 3 Beds
- 3 Baths
- Built 1927
224 Jason St, Pittsfield, MA 01201

This well-cared-for home offers a total of three bedrooms and three bathrooms, including a private in-law suite in the lower level.The in-law suite features its own bedroom, bathroom, kitchen and living area--ideal for extended family, guests, or potential rental opportunities. The basement also features a dedicated workshop space, great for tinkering, crafts, or additional storage.The home has

Jesse Dimitropolis RE/MAX COMPASS

224 Jason St, Pittsfield, MA 01201

/33
Est $337,150 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,269 Sq Ft
6 Mountain Dr, Pittsfield, MA 01201

6 Mountain Dr, Pittsfield, MA 01201

/12
$59,000
- Land
- 1.00 Acre
- $59,000 per Acre
0 Westbrook Terrace, Pittsfield, MA 01201

Build your dream home in the prestigious gated enclave of Woodmonte Estates, located in the heart of Berkshire County, Massachusetts. This cleared 1-acre corner lot offers a rare opportunity to create a custom residence in one of the regions most desirable communities, surrounded by privacy, beauty, and high-end homes.With access to public utilities and underground electricity already in

Community Lands

0 Westbrook Terrace, Pittsfield, MA 01201
/31
$310,000 Sold Jul 21, 2025
- 1,050 Sq Ft
- $295/SF
- 3 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1958
110 Maple Grove Dr, Pittsfield, MA 01201

Charming 3-Bedroom Ranch in a desirable southeast neighborhood. This cozy and efficient single level home is ready for your finishing touches. Enjoy the outdoors in your private backyard. Ideal for entertaining, pets or relaxing on the back patio. Attached garage. New oil burner installed 05-2025. Bonus room in the basement for your imagination. Concrete driveway. Front porch for afternoon sun.

Anthony Riello LAMACCHIA REALTY, INC

110 Maple Grove Dr, Pittsfield, MA 01201

/24
Est $221,415 Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,502 Sq Ft
21 George St, Pittsfield, MA 01201

21 George St, Pittsfield, MA 01201

/50
$469,900
- 4 Beds
- 2 Baths
- 1,984 Sq Ft
225 Williams St, Pittsfield, MA 01201

Meticulously maintained Berkshire brick beauty. This timeless home sets the stage with elegance and charm, subtlety wrapping you in quiet comfort and peace within the brick walls. Impeccably improved and maintained to captivate you as you enter each room. Relax and share time in the light filled living room with full length picture window. Feel the glow of the glimmering gas fired fireplaced

Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

225 Williams St, Pittsfield, MA 01201
/37
$350,000 Sold Jul 18, 2025
- 1,919 Sq Ft
- $182/SF
- 37 Days On Market
- 4 Beds
- 2 Baths
- Built 1979
881 Holmes Rd, Pittsfield, MA 01201

Enjoy beautiful mountain views from this spacious 4-bedroom, 2-bath Pittsfield split-level on Holmes Road. Featuring a bright open layout, large picture windows, and fresh interior updates, this home offers a flexible floor plan with generous living space. The lower level includes space ideal for a home office or family room. Enjoy outdoor living on the rear deck and a large private yard. With a

Ed Rich BISHOP WEST REAL ESTATE

881 Holmes Rd, Pittsfield, MA 01201

/25
Est $377,015 Not Listed For Sale
- 6 Beds
- 2 Baths
- 2,592 Sq Ft
72 Stratford Ave, Pittsfield, MA 01201

72 Stratford Ave, Pittsfield, MA 01201

/38
$375,000
- 3 Beds
- 2 Baths
- 2,024 Sq Ft
39 Velma Ave, Pittsfield, MA 01201

Enjoy this move in ready, 3 bedroom home with a finished basement! This property offers a beautiful remodeled kitchen, with open floor plan to the dining room, making entertaining a breeze. The home features charming original hardwood flooring throughout the first level. The main bathroom is tastefully updated with a whirlpool tub. Natural light fills the first floor living room & bedroom.

Laiken Rapisarda LAMACCHIA REALTY, INC

39 Velma Ave, Pittsfield, MA 01201
/38
$325,000 Sold Jul 18, 2025
- 1,512 Sq Ft
- $215/SF
- 7 Days On Market
- 4 Beds
- 2 Baths
- Built 2005
97 Dorchester Ave, Pittsfield, MA 01201

Welcome to this well-maintained Cape-style home, built in 2005. With four spacious bedrooms and two full bathrooms, there's room for everyone. Enjoy the ease of first-floor living with two bedrooms, ideal for guests, a home office, or multigenerational needs. The kitchen features newer stainless-steel appliances. Outside you will find a manageable yard, perfect for low-maintenance living. Enjoy

Jessica Rizzo LAMACCHIA REALTY, INC

97 Dorchester Ave, Pittsfield, MA 01201

/35
Est $333,460 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,167 Sq Ft
40 Plinn St, Pittsfield, MA 01201

40 Plinn St, Pittsfield, MA 01201

/25
$619,900
- 4 Beds
- 2.5 Baths
- 2,646 Sq Ft
68 Brookside Dr, Pittsfield, MA 01201

This terrific side hall Colonial offers a spacious, family-friendly layout with timeless appeal and effortless flow. The heart of the home is the large, updated kitchen featuring stone countertops and a sunny dining area, ideal for everyday living and entertaining.Gracious first-floor spaces include a step-down family room with a wood-burning fireplace, built-ins, and gleaming hardwood floors, as

Kathleen Quinn WILLIAM PITT SOTHEBY'S - LENOX

68 Brookside Dr, Pittsfield, MA 01201
/35
$397,500 Sold Jul 18, 2025
- 1,941 Sq Ft
- $205/SF
- 5 Days On Market
- 3 Beds
- 1 Bath
- Built 1902
955 Barker Rd, Pittsfield, MA 01201

Quintessential New England farmhouse nestled on over an acre in the heart of the Berkshires! This inviting 3-bedroom home blends timeless charm with modern updates--just minutes from Tanglewood and downtown Lenox. Enjoy serene country living with a sweet front porch, a 2-car garage, and a spacious bonus room ready for your finishing touches to become your ideal outdoor entertainment space. Step

Victoria Standring LAMACCHIA REALTY, INC

955 Barker Rd, Pittsfield, MA 01201

/57
Est $373,512 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,238 Sq Ft
49 Yorkshire Ave, Pittsfield, MA 01201

49 Yorkshire Ave, Pittsfield, MA 01201

/33
$489,900
- 4 Beds
- 2.5 Baths
- 2,300 Sq Ft
59 Joan Dr, Pittsfield, MA 01201

Welcome to 59 Joan Drive, a stunning 4-bedroom, 2.5-bath raised ranch located in one of Pittsfield's premier neighborhoods. This inviting home features a spacious open floor plan, perfect for both relaxation and entertainment. The main level boasts a bright living room, a modern kitchen with ample storage, and a dining area that opens to a spacious wrap around deck, ideal for outdoor gatherings.

Doug Collins LAMACCHIA REALTY, INC

59 Joan Dr, Pittsfield, MA 01201
/33
$227,000 Sold Jul 16, 2025
- 1,224 Sq Ft
- $185/SF
- 9 Days On Market
- 3 Beds
- 1 Bath
- Built 1933
13 Oswald Ave, Pittsfield, MA 01201

Delightful three-bedroom, one-bathroom bungalow located off West Housatonic Street in Pittsfield. This charming home features hardwood floors throughout. Enjoy the open concept layout with a dining room flowing into the livingroom. The main floor has two cozy bedrooms and a conveniently located bathroom. Ascend through one of the bedrooms to discover a unique third-floor open bedroom. Outside,

Mariah Worth LAMACCHIA REALTY, INC

13 Oswald Ave, Pittsfield, MA 01201

/17
Est $210,911 Not Listed For Sale
- 5 Beds
- 2 Baths
- 2,014 Sq Ft
32 Madison Ave, Pittsfield, MA 01201

32 Madison Ave, Pittsfield, MA 01201

/37
$369,900
- 3 Beds
- 1 Bath
- 1,040 Sq Ft
165 Harryel St, Pittsfield, MA 01201

Located in a highly desirable Southeast Pittsfield neighborhood, this meticulously maintained, three bedroom, one bath ranch home offers a winning combination of location, condition, and value. Built with solid brick construction and set on a beautifully broad lot with mature landscaping and a fully fenced-in backyard, this property is a true Berkshire gem.Step inside to discover hardwood floors

Nick Geranios WILLIAM PITT SOTHEBY'S - LENOX

165 Harryel St, Pittsfield, MA 01201
/26
$222,000 Sold Jul 15, 2025
- 1,366 Sq Ft
- $163/SF
- 13 Days On Market
- 3 Beds
- 1 Bath
- Built 1954
26 Highlawn Dr, Pittsfield, MA 01201

Needs Paint! This adorable and affordable ranch-style home features vinyl siding, replacement windows, NEW heating system, New hot water and SO MUCH POTENTIAL! Enjoy this lovely flat yard just in time for summer! This home had an operational second bath in the basement that offers the possibility of renovating it back to life! A rare find in a FANTASTIC area! Call your friends, order the

Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

26 Highlawn Dr, Pittsfield, MA 01201

/25
Est $256,303 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,216 Sq Ft
184 Woodlawn Ave, Pittsfield, MA 01201

184 Woodlawn Ave, Pittsfield, MA 01201

/49
$369,900
- 2 Beds
- 2 Baths
- 1,557 Sq Ft
55 Revilla Terrace, Pittsfield, MA 01201

Move-in ready New Construction in Southeast Pittsfield! This lovely home blends style, sophistication, function, efficiency & LOCATION! Enjoy an amazing kitchen, boasting an oversized quartz island, 2 stunning full bathrooms with high-end finishes, gleaming wood floors, large deck and FULLY Finished lower level with full walkout. This multi functional lower level space offers so many

Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

55 Revilla Terrace, Pittsfield, MA 01201
/45
$247,000 Sold Jul 15, 2025
- 2,856 Sq Ft
- $86/SF
- 5 Days On Market
- 8 Beds
- 2 Baths
- Built 1900
43 Grove St, Pittsfield, MA 01201

First time to market in decades ~ Large Centrally Located True Duplex! This property has been cherished by the same owner since 1987! It's a fantastic opportunity to own your home while generating rental income or to use as an investment property. Each unit features 4 bedrooms, 1 bathroom, a spacious kitchen with a pantry, dining room, and living room. The duplex boasts separate utilities,

Maureen Kirby NOCHER REALTY

43 Grove St, Pittsfield, MA 01201

/4
Est $199,392 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,016 Sq Ft
287 Columbus Ave, Pittsfield, MA 01201

287 Columbus Ave, Pittsfield, MA 01201

/44
$396,500
- 3 Beds
- 2.5 Baths
- 1,951 Sq Ft
7 Cynthia Ln, Pittsfield, MA 01201

A great opportunity to own in Southview. With only 24 units, turnover is unusual in this Khoury-built established condo community! Tri-level townhouse unit offers great space for year-round or vacation living. First floor boasts a spacious great room/living w hardwood flooring, fireplace, dining and entrance to large and private rear deck. Kitchen with eat-in area. Upper level includes

Pamela Roberts ROBERTS & ASSOC. REALTY, INC

7 Cynthia Ln, Pittsfield, MA 01201
/32
$405,000 Sold Jul 14, 2025
- 3,656 Sq Ft
- $111/SF
- 4 Days On Market
- 8 Beds
- 4 Baths
- Built 1880
33 Plunkett St, Pittsfield, MA 01201

This well-maintained four-family property, renovated in 2017, offers excellent cash flow potential and is ideal for both investors and owner-occupants. Recent upgrades include a new roof, windows, complete electrical and plumbing systems, all certified lead-safe for every unit.Each spacious 2-bedroom apartment has been thoughtfully updated and is separately metered for utilities, ensuring

Marc Bellora LAMACCHIA REALTY, INC

33 Plunkett St, Pittsfield, MA 01201

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