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46 Photos
LAMACCHIA REALTY, INC
$390,000
6 BD | 3 BA
Multi-Family

Charming Duplex in Southeast Pittsfield - Great Investment Opportunity!Welcome to this well-maintained duplex nestled in a desirable Southeast Pittsfield neighborhood! The layout on both sides includes a living room, dining room, large kitchen, and three comfortably sized bedrooms. Unit #38 has one bath and laundry hook-ups in the basement, while Unit #36 has 1.5 baths and laundry hook-ups on the first floor. Each unit also features its own basement and attic access, and separate utilities. Outside, a private backyard is perfect for gardening, relaxing, or entertaining, along with off-street parking. This duplex is located on a quiet, tree-lined street just minutes from schools, shopping, parks, and downtown Pittsfield.


41 Photos
MOCKINGBIRD REAL ESTATE
$392,000
3 BD | 2 BA
Residential - Single Family

JUST REDUCED.....Step into this bright and sunny newly renovated 3 bedroom 1 1/2 bath home. From the moment you walk in, you will notice the new kitchen, bathroom and fresh paint. There is a large finished basement ideal for family room, workout room, or playroom. Add 2 other rooms in the lower level complete with laundry and 1/2 bath. Walk onto the deck from the dining area and enjoy the privacy with a fenced in backyard.There is a large 2 car attached garage. All situated close to shopping, parks, walking trails and more


17 Photos
BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
$399,000
3 BD | 1 BA
Residential - Single Family

Enjoy easy one-level living in this well-kept ranch home, lovingly owned and updated by a single family since it was built. A welcoming porched entry opens to a bright living room featuring a large picture window and a beautiful stone-faced wood-burning fireplace.This 3-bedroom, 1-bath home features hardwood floors throughout and a functional layout. The family room off the garage leads into a spacious kitchen with solid oak cabinets and a cozy eating area. Relax in the added sunporch or on the deck with an awning, perfect for enjoying peaceful views year-round.The full, clean concrete basement offers versatile space for extra living, storage, or hobbies. Outside, the 1.49-acre yard is a true highlight, opening to a wide field of green for privacy, play, or gardening


45 Photos
ASHMERE REALTY, INC.
$399,900
3 BD | 2 BA
Residential - Single Family

Step into this beautifully renovated home, where natural sunlight fills spacious, oversized rooms, creating a warm and inviting atmosphere. Every detail has been thoughtfully updated, showcasing a fresh, modern aesthetic complemented by brand-new appliances. The expansive primary bedroom features two closets, with one large enough to serve as a nursery or home office, complete with two windows for abundant light. Perfectly positioned in a prime location--just minutes from Jiminy Peak Mountain Resort, tranquil lakes, and convenient shopping--this home seamlessly blends comfort, style, and accessibility.


45 Photos
KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$399,999
4 BD | 2 BA
Residential - Single Family

Welcome to this beautifully maintained ranch offering the perfect blend of comfort, style and functionality. This move in ready home features 4 bedrooms , 2 full baths and a finished basement. Step inside to find wood floors, a warm and inviting layout with plenty of natural lightening. The kitchen opens to the dinning area. Outside enjoy a lovely front porch for morning coffee, in the backyard enjoy a private oasis with a deck and built in pool ideal for relaxing and hosting summer gatherings. The attached garage provides convince and extra storage, completing this picture perfect property. If you're looking for a well cared for home with great outdoor living this one checks all the boxes.


24 Photos
HART REALTY
$419,900
4 BD | 3 BA
Residential - Single Family

Beautiful views and move-in condition! This home has a new kitchen with SS appliances, stone countertops, tile back splashes and slider to the 2 tiered deck overlooking Noble farm fields. Relax and take in nature's beauty! There are all new floors, interior and exterior paint, and extreme low temp high efficiency heat pump/Air conditioning. Updated 2.5 bathrooms and a 2 car garage make this home everything that you need.


24 Photos
HARSCH ASSOCIATES
$419,900
3 BD | 2 BA
Residential - Condo/Townhouse

Country Village furnished end unit condo with 3 bedrooms, 2.5 baths walkable to pool, slopes, main lodge and country store. Living room has wood burning fireplace with upstairs open seating area/loft overlooking lower level. nice rear deck with distant mountain views over back meadow. Good storage for skis and outdoor equipment. This unit has been extensively and tastefully renovated with over 120K in upgrades including two mini-split HVAC units resulting in lower heating/cooling costs, and kitchen and bath upgrades. The unit has never been in the rental pool resulting in less wear and tear.


26 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$425,000
2 BD | 2 BA
Residential - Condo/Townhouse

Imagine waking up in a sun-splashed home just steps from Great Barrington's lively Main Street--where every cafe, bookstore, and gallery feels like an extension of your neighborhood. This second-floor floor-through condo is more than a home; it's a canvas for your life.Over 1,800 sq. ft. of expansive living space unfolds with towering ceilings, oversized windows, and graceful arched doorways that evoke another era. Every detail--from the textured walls to the light pouring in at all hours--creates a sense of romance and possibility.The home is thoughtfully divided: one wing offers a spacious bedroom and lounge with guest alcove, while the other wing hosts a dining area, kitchen, and charming nook for work or rest.


51 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$426,900
4 BD | 2 BA
Residential - Single Family

New and Improved! Lovely finishing touches to make it sparkle and shine and move in ready! New roof, fresh exterior paint, new energy efficient mini splits for heating and cooling and Mass Save Insulated for low annual utility cost, new 200 amp electric service, updated baths, full-length front porch perfect for relaxing or socializing. Be welcomed onto the glorious front porch wonderfully inviting facing west for incredible sunsets and a sneak peak view of Bousquet Mountain. Inside, a gracious entry leads to a classic living room with built-in bookcases, window seats. Gleaming oak floors flow throughout. The formal dining room with a butler's pantry with a coffee bar and fridge nook. The kitchen features new hardwoods, a darling everyday dining nook with built-in for the cookbook


43 Photos
SIGNATURE ASSOCIATES
$429,400
4 BD | 2 BA
Residential - Single Family

Lovely, meticulously maintained home in southeast Pittsfield offers spacious living. Attractive kitchen with large dining area leading to deck. Generous yard with fenced area for pets or kids, a garden area, large shed. There is an ''in-law'' arrangement in the lower level that has living room, bedroom or dining room, a den or dining or bedroom, kitchenette, full bath and door to the garage.Three bedrooms on first floor with nice closets, and there is a full bath. 2 car garage with work area. Come and see this home! Open house 10/25 10:30-12:30


57 Photos
BURNHAM GOLD REAL ESTATE, LLC
$449,000
4 BD | 3 BA
Residential - Single Family

One-of-a-Kind 1893 Victorian in the Heart of Adams. Step back in time while enjoying every modern comfort in this turnkey 1893 Victorian, ideally located in-town in charming Adams, Massachusetts. This beautifully preserved 4-bedroom, 3-bath home is a rare gem -- blending rich history with thoughtful updates that honor its original craftsmanship. From the moment you enter, you'll be captivated by the home's ornate woodwork, original hardwood floors, and stained-glass windows that bathe each room in colorful light. Period details abound -- built-ins, decorative moldings, and a handsome fireplace anchor the living spaces with warmth and character. The bathrooms have been refreshed, offering modern convenience while preserving the home's timeless style.


42 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$449,900
6 BD | 2 BA
Residential - Single Family

Discover the charm of yesteryear with this enchanting 6-bedroom, 2-bathroom antique home nestled in the vibrant town of Lee. Accompanied by a large two-story stone barn, this residence offers a blend of historical elegance and modern potential. Original features such as wood floors, Dutch door, and classic stairway railing are complemented by a dining room with beamed ceilings, built-in china cabinets, and bay window with marble seat. Stained glass windows and pocket doors add to the home's unique character, while a marble fireplace graces the front parlor. The sizeable retro kitchen, complete with Geneva cabinets, awaits your personal touch. Set on a corner lot with mature plantings, the property boasts a beautiful backyard--


45 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$450,000
4 BD | 3 BA
Residential - Single Family

This well-cared-for colonial home has been cherished by the same owners for over seven decades and is ready to welcome its next chapter. The first floor offers a spacious layout with a large kitchen, dining room with access to a seasonal porch, a living room featuring a wood-burning fireplace, a family room with half bath, and a four-season sunroom surrounded by windows overlooking the backyard. Upstairs, the primary bedroom impresses with double closets and a vaulted ceiling, complemented by three additional bedrooms and a full bathroom. The fully finished basement provides valuable extra living space with a laundry room, 3/4 bath, and game room. Recent updates include a new roof (2021), heating system (2023), and refinished floors with fresh paint (2025).


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BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD
$459,900
4 BD | 2 BA
Residential - Single Family

Motivated Seller.! A home that is in move in condition Prestigious grand colonial located in the lovely Southeast area. This home has been meticulously maintained. Four large bedrooms, formal living room with fireplace, Glass doors leading out to a pergola, A family room, dining room, renovated kitchen , den or office could be a fifth bedroom. One upstairs bathroom renovated and one on the first level,The landscaping is a gardener's dream come true.A Berkshire County haven. Walking distance to theaters and great downtown eateries and coffee shops. Close to Rt 7 which leads to Lenox, Tanglewood Stockbridge Red Lion Inn.. Great Barrington. Skiers vacation spots. Words cannot describe all this property has to offer. A must see.


40 Photos
LAMACCHIA REALTY, INC
$465,000
5 BD | 3 BA
Residential - Single Family

OPEN HOUSE Sat 11/01/25 11am-12:30pm. This stunning 5-bedroom, 3-bath farmhouse was fully renovated from top to bottom in 2020, offering 2,800 SqFt of stylish, move-in-ready living space in one of Southeast Pittsfield's most desirable neighborhoods. Situated on a generous corner lot, the home makes a striking first impression with its inviting wraparound front porch. A circular driveway provides ample parking and is complimented by a detached one-car garage. Step through the front door into a spacious foyer with sleek hardwood floors throughout the open concept main level. The dining room has enough space for memorable meals and entertaining, while the chef's kitchen is outfitted with stainless steel appliances, a natural gas range, quartz & granite countertops, center island and French


48 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$469,000
4 BD | 4 BA
Residential - Single Family

Step into a world where historic charm meets contemporary living in this unique 4-bedroom, 4-bath Arts & Crafts home located in the heart of Southeast Pittsfield. This one-of-a-kind residence is brimming with character and has been lovingly maintained to showcase its original features while providing all the comforts of Berkshire living. This majestic home has a fascinating origin story. Built in the late 1800s, it was once the east wing of the summer residence of the Pillsbury family. Originally adjoined with the house behind it on Wendell Avenue and situated a half block away, the sprawling grand estate was divided into two separate homes, and carefully moved by horse in the early 1900s, establishing the neighborhood that would grow around them.


48 Photos
BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
$469,900
3 BD | 2 BA
Residential - Single Family

Welcome to 93 Roselyn Drive, a beautifully maintained, move-in-ready, light-filled mid-century gem with style, function, and effortless upkeep, ideally situated in Pittsfield's desirable west-side neighborhood.This home offers big-sky views and a private 0.75-acre yard - perfect for morning coffee, stargazing, or weekend gatherings on the expansive two-level deck overlooking mature, easy-to-care-for gardens.Inside are sun-filled rooms, a classic stone gas fireplace with remote control, a fabulous bonus room with large windows facing the backyard - ideal for a home office, family room, or yoga studio - plus a newly finished lower level adding more versatility with a full bath, cedar closet, laundry area, and plenty of room for a guest suite, media room, or private gym.


33 Photos
LAMACCHIA REALTY, INC
$469,900
4 BD | 3 BA
Residential - Single Family

Welcome to 59 Joan Drive, a well appointed 4-bedroom, 2.5-bath raised ranch located in one of Pittsfield's premier neighborhoods. 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. The master suite offers a private full bath, while three additional bedrooms provide plenty of space for family or guests. The finished lower level includes a versatile family room, 1/2 bath, laundry room and access to the 2 car garage. Perfectly set on approx .42 acres of land this property offers mountain views, yet in a neighborhood setting. This home comes with a one year transferable home warranty, whole house water filter and additional insulation was just added to increase efficiency.


59 Photos
LAMACCHIA REALTY, INC
$519,900
4 BD | 3 BA
Residential - Single Family

Welcome to this beautifully appointed & pristinely maintained residence that combines timeless character with modern upgrades. Situated on a desirable corner lot, offering a fully fenced-in yard. This spacious home features generously sized rooms throughout, offering comfort & elegance at every turn. The stunning kitchen is equipped with stainless steel appliances, soapstone countertop, quartz island and classic backsplash. A formal dining room flows seamlessly into the side porch, overlooking the serene side yard, perfect for entertaining. The expansive living room boasts a stacked stone wood-burning fireplace and built-ins. Just off the living room, a cozy sitting area with an electric fireplace provides a perfect spot for an office or a reading nook.


48 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$525,000
4 BD | 3 BA
Residential - Single Family

This well-cared-for colonial home has been cherished by the same owners for over seven decades and is ready to welcome its next chapter. The first floor offers a spacious layout with a large kitchen, dining room with access to a seasonal porch, a living room featuring a wood-burning fireplace, a family room with half bath, and a four-season sunroom surrounded by windows overlooking the backyard.Upstairs, the primary bedroom impresses with double closets and a vaulted ceiling, complemented by three additional bedrooms and a full bathroom. The fully finished basement provides valuable extra living space with a laundry room, 3/4 bath, and game room.Recent updates include a new roof (2021), heating system (2023), and refinished floors with fresh paint.

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