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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


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THE KINDERHOOK GROUP - PITTSFIELD
$399,000
3 BD | 2 BA
Residential - Single Family

A rare find: 3 Bedroom colonial home with a picturesque pond for endless enjoyment. Dining under the stars in your private backyard oasis and waking up to breathtaking views and gentle melodies of nature. Discover the magic where memories are waiting to be made. Anderson windows and doors. A brick chimney with a wood stove adds seasonal warmth to the living room. The back porch entices you to come relax or entertain while listening to the babbling brook and a serene view of the pond. The rolling field across the paved street provides plenty or privacy. The convenience to work from home is made easy with fast fiber optics and Windsors low taxes. 39 minutes to Northampton and


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HOUSATONIC REAL ESTATE
$399,000
3 BD | 2 BA
Residential - Single Family

Mid-1960s ranch on a quiet street with nearly 1/2 acre! A perfect family home to settle down in Southern Berkshire County. Semi-finished basement is a huge bonus, plus garage and additional detached barn/workshop. Sunny, spacious and ripe with potential. Some thoughtful updates will be needed -- or move in today and make it yours!


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ALTON & WESTALL REAL ESTATE AGENCY, LLC
$399,900
3 BD | 2 BA
Residential - Single Family

Nestled in the heart of downtown Cheshire, this beautifully updated New England farmhouse blends classic charm with modern comforts. Featuring a convenient first-floor bedroom and full bath, plus two additional bedrooms and a second full bath upstairs. The recently renovated kitchen boasts granite countertops, abundant cabinet space, stainless steel appliances, and an abundance of natural light. Enjoy Berkshire summers relaxing on the spacious back decks or lounging on the shaded front porch, all with new composite decking and railings. Located within walking distance to the scenic Ashuwillticook Rail Trail and less than a mile from Cheshire Lake. New septic system installed in 2022. Current owner has done extensive upgrades and improvements. See full list under Documents.


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.


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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.


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COMPASS MASSACHUSETTS , LLC GB
$419,000
3 BD | 1 BA
Residential - Single Family

1900's cottage set above the village of West Stockbridge. Open plan living with updated kitchen and bath, with laundry tucked in below the stairs and second floor has three bedrooms. Fenced yard creating a nice private space with wraparound deck. Shed at the back of the property providing a lovely additional space.


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COLDWELL BANKER COMMUNITY REALTORS
$425,000
3 BD | 2 BA
Residential - Single Family

Nestled in a peaceful 4.3 wooded setting, this spacious home captures the warmth and charm of log home living. The open concept design offers a warm and inviting atmosphere, highlighted by cathedral ceiling and rich wood interiors. The kitchen connects to the dining and living areas, where a pellet stove adds cozy comfort, and patio doors lead to a large front andback decks, the perfect place to gather with friends or simply relax and enjoy nature. The main bedroom suite features patio door to the back deck, a full bath, and a custom built laundry closet, Two additional bedrooms and another full bath complete the main level. The finished lower level is designed for fun and entertainment, featuring a generousfamily/recreation room with a projector for movie nights


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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


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WILLIAM PITT SOTHEBY'S - LENOX
$439,900
3 BD | 2 BA
Residential - Single Family

Discover the charm of Rowe with this exceptional Cape home, set on 6.08 acres of serene beauty. The open floor plan and large windows create a bright and inviting atmosphere, featuring two spacious bedrooms on the first floor and a luxurious primary suite above. Step out onto the wraparound deck, perfect for peaceful mornings or lively gatherings. The loft office, equipped with high-speed fiber internet, makes remote work a delight. Enjoy easy access to hiking trails, gardens, and winter activities--ideal for those seeking a tranquil escape. With a low-maintenance design, the large basement provides space for hobbies and offers yard access. Rowe offers low taxes and the lovely Pelham Park. With a newer roof and ready-to-be-reinstalled solar systems, this is a must-see in a beautiful town!


43 Photos
HOUSATONIC REAL ESTATE
$449,000
3 BD | 2 BA
Residential - Single Family

Nestled in Sheffield Village on 8+ acres, this charming New England farmhouse blends rustic character with modern comfort. Featuring 3 bedrooms, 2 baths, wood floors, beams, Great Room with a gas stove offers a warm inviting space Enjoy a country kitchen with a pantry. Screened in porch with outdoor patio, gardens, and two sheds for storage or hobbies. Perfect as a private sanctuary or Airbnb, this property combines timeless charm, tranquil surroundings, and great potential.


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--


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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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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$469,000
3 BD | 2 BA
Residential - Single Family

Tucked away in the desirable, low-tax community of Richmond, Massachusetts, this 3-bedroom, 2-bathroom ranch, surrounded by higher-priced properties, offers comfortable single-floor living. The open-concept living area, filled with natural light, includes a recently updated kitchen and features quartz countertops, quality stainless appliances, and ample counter space. The master suite includes a newly updated bathroom. Two additional spacious bedrooms offer flexibility for guests or a home office. A privately owned solar array provides net-zero energy, combining eco-conscious living with cost savings. Located just 4 miles from Tanglewood, the Berkshires' premier cultural attraction, 5 miles from Lenox, the region's culinary hub, 4 miles from West Stockbridge, and 5 miles from Balderdash C


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WILLIAM PITT SOTHEBY'S - LENOX
$469,000
3 BD | 3 BA
Residential - Single Family

Located in the Historic District of the picturesque town of Heath, this former Artist loft has been thoughtfully maintained and expanded over the years. Large, expansive spaces greet you as you walk into the 3304 sqft. home with three bedrooms and three bathrooms. There is a separate sizeable bright kitchen wing with a great view of the large private yard, or you can enjoy the yard on the 2nd-floor deck. The home also has a 2-plus acre meadow with a small barn perfect for a hobby farmer or a horse enthusiast. This unique, comfortable house is set in a very private, peaceful setting, offering a tranquil escape from the hustle and bustle of everyday life.


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GELINAS REAL ESTATE
$469,000
3 BD | 3 BA
Residential - Single Family

Welcome home to this warm and inviting property set in a quiet and desirable Pittsfield neighborhood. With a comfortable flow and plenty of space for gathering, this home is ideal for entertaining and spending time with loved ones, especially as we head into the winter months. Inside, you'll find 3 bedrooms, 2 full baths, and 1,890 sq. ft. of well-designed living space. The cozy downstairs living room features a gas fireplace insert, perfect for chilly evenings, while the open kitchen/dining area, as well as a wet bar make this home an entertainers dream. The heated sun porch off the kitchen offers a bright, relaxing spot to enjoy year-round.


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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.


39 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$475,000
3 BD | 3 BA
Residential - Single Family

Experience the charm of country living in this comfortable home, situated in the peaceful town of Charlemont, on Wilder Brook. The property includes a spacious barn, formerly a cabinet workshop, and an additional outbuilding for gardening tools or chickens. Enjoy hosting gatherings in the large kitchen and dining room, or relax in the expansive open living area. Upstairs, you'll find three roomy bedrooms and two bathrooms, providing plenty of space for everyone. Perfect for outdoor enthusiasts, this home is just minutes from mountain biking, ziplining, the mountain coaster, and downhill skiing at Berkshire East, as well as world-class fishing and tubing on the beautiful Deerfield River. Seize this opportunity to make this remarkable property yours!


39 Photos
HOUSATONIC REAL ESTATE
$475,000
4 BD | 3 BA
Residential - Single Family

Step into history with this captivating 4-bedroom, 3-bathroom single-family home, offering 2,288 sq. ft. of living space. Built in the 1860s, this residence exudes charm while incorporating numerous modern updates for contemporary comfort. Nestled on a quarter-acre lot in a quiet town, this home boasts a lush yard and a fully screened-in porch, perfect for enjoying serene mornings and tranquil evenings. The spacious rooms provide versatility and ample living space, while abundant storage. A standout feature is the standalone two-car garage. Experience a unique blend of historic elegance and modern luxury in this remarkable property--an ideal sanctuary for those seeking a peaceful, yet connected lifestyle

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