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51 Photos
ROBERTS & ASSOC. REALTY, INC
$424,900
4 BD | 2 BA
Residential - Single Family

Step into style and comfort in this beautifully maintained move-in ready four bedroom, two-bath home in Southeast Pittsfield Conveniently located and perfectly positioned on a landscaped, fenced, corner lot. From the moment you enter the spacious hallway, you'll see gleaming hardwood floors that add warmth and character to every room. First floor includes timeless charm of a fireplaced living room, formal dining open kitchen and a family room with skylights. First floor bath w shower and bonus is a year-round heated sunroom on its own heat zone. Second floor features four generously proportioned light-filled bedrooms, updated full bath. Private rear patio, attached garage, Natural gas heat - four zones! Minutes to theater, restaurants and all of the Berkshire attractions.


32 Photos
JIMINY REALTY
$425,000
2 BD | 2 BA
Residential - Condo/Townhouse

Top Floor unit with views of the slopes! This totally renovated 2-bedroom 1.5 bath unit with brand new everything. New floors. New appliances. New furniture. New Paint. New exposed beams. Private parking spot right out front. Private ski locker for your skis and boots. This unit also comes with a private owners closet that holds all the extras like bikes and rackets. Let's not forget this unit has a wood burning fireplace for the cold winter nights. Tennis courts and summer swimming pool are steps away from this unit. Park your car and walk to everything. Ski right up to the back of the building. Turnkey unit already for the winter snow.


43 Photos
PAULA MCLEAN REALTORS INC.
$425,000
2 BD | 3 BA
Residential - Single Family

Classic New England farmhouse featuring a charming kitchen with beautiful Berkshire views and an open, inviting layout perfect for entertaining. The 1st floor offers, full bath and convenient laundry hookups, along with 2 living rooms. One ideal for relaxation and the other a perfect home office, playroom, game room. Upstairs, you'll find 2 good sized bedrooms each with their own full bathroom for ultimate comfort and privacy. Outside a 2 car garage great for snow days or storing an old vintage car! Ideally located close to Tanglewood, Ventfort Hall, Bousquet Mountain & Sport, The Colonial Theatre as well as wonderful restaurants, cafes, and shopping. A little something for everyone.


15 Photos
DALTON TOWN & COUNTRY ASSOC, INC
$425,000
4 BD | 2 BA
Residential - Single Family

4 Bedroom 1.5 bath brick cape on over half acre lot, wood floors throughout, fireplace, newly painted, dining room, eat in kitchen, one car attached garage, breezeway, family room in basement.Includes separate 720 square foot ranch with 2 bedrooms, 1 bathroom on property, front porch, vinyl siding, separate utilities


38 Photos
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


59 Photos
KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$425,000
5 BD | 3 BA
Multi-Family

This exceptionally well-maintained Civil War-era farmhouse presents a rare opportunity to own a property rich in character while offering remarkable versatility. Thoughtfully preserved and updated, the home accommodates a variety of living arrangements, functioning seamlessly as a spacious single-family residence, a multi-generational home, or a duplex-style property with income potential for both long- and short-term rentals. Set within a charming, low-tax community, the property offers an appealing balance of tranquility and accessibility. Its proximity to Jiminy Peak places year-round recreation just moments away, including skiing, hiking, mountain biking, and outdoor adventure parks. The surrounding area is equally known for its vibrant cultural scene, with nearby venues offering arts,


21 Photos
BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
$425,000
3 BD | 2 BA
Multi-Family

Two family minutes from downtown Lenox. First floor unit has 2 bedrooms with spacious living area and kitchen. Upstairs unit is a 1 bedroom 1 bath with fireplace and back deck. Roof replaced in 2021, natural gas, town water and sewer.


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.


47 Photos
STONE HOUSE PROPERTIES, LLC
$425,000
2 BD | 1 BA
Residential - Single Family

Charming home in a private setting, close to all area attractions. The oversized front porch leads you inside to a light filled first floor, with newly finished hardwood floors and high ceilings. The living and dining rooms offer flexible space for relaxing or entertaining. The kitchen has lovely southern light, as well as access to the back deck for summer dining. Upstairs are two generously sized bedrooms, and a full bathroom w/ laundry. The third floor has a finished bonus space as well as an unfinished storage area. Outdoor amenities include a nice size yard, storage shed, and an in-ground pool.The property has a new 3 bedroom septic system, and a full de-leading compliance certificate. Minutes to downtown W. Stockbridge, 10 minutes to Tanglewood, and 35 minutes to Albany.


4 Photos
COHEN & WHITE ASSOCIATES

NORTH EGREMONT - Almost 18 elevated acres with sweeping views of the Berkshire Hills that has been surveyed, flagged with enough road frontage to subdivide once. An open meadow with woodlands as a backdrop make this parcel most desirable....a must see!


19 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$429,000

Commercial

*NEW PRICE* HISTORIC RAILROAD STATION WITH CABOOSE. Built in 1893. Renovated in 2018, 2,134 sf. Unique opportunity to own a piece of Lee History. Restored and converted for Bar/Restaurant use. Centrally located in downtown. Seating for 65 plus Outdoor Deck. Parking for 30 cars. Property also available for Lease (MLS# 243435).


43 Photos
HOUSATONIC REAL ESTATE
$429,000
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.


22 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$429,000
3 BD | 2 BA
Residential - Single Family

Welcome to 13149 NY 22, Canaan, NY 12029 a beautifully updated 3 bedroom, 1.5 bath ranch set on two open, usable acres. This home has been thoughtfully refreshed from top to bottom, offering true ease of living in a peaceful countryside setting. Step inside to find gleaming wood floors throughout, freshly painted interiors, and renovated bathrooms with crisp, modern finishes. The efficient single level layout provides comfortable flow between the bright living spaces and the three well sized bedrooms. Recent improvements include a brand new roof, ensuring years of worry free ownership. An attached heated two car garage adds convenience and storage, while the expansive yard gives you plenty of room to garden, relax, or simply enjoy the quiet surroundings.


44 Photos
ROBERTS & ASSOC. REALTY, INC
$429,900
3 BD | 3 BA
Residential - Condo/Townhouse

Situated on an elevated lot in desirable Walden Village, this meticulously maintained home offers a private backyard perfect for outdoor entertaining. The main level features a convenient primary suite with a full ensuite bath, a guest powder room, and the convenience of first-floor laundry. An elegant, open floor plan provides excellent flow for both entertaining and everyday living, and a bonus family room adds flexible living space. Upstairs are two additional bedrooms and a full bath. All bathrooms have been updated, and the home has been carefully maintained, making it move-in ready. Enjoy close proximity to community amenities, including the tennis courts and pool.


46 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$429,900
3 BD | 3 BA
Residential - Single Family

Welcome to 42 Lexington Parkway, a beautifully maintained Colonial tucked into one of Southeast Pittsfield's most desirable neighborhoods. Offering over 1,800 square feet of living space, this home is larger than it appears and filled with thoughtful updates throughout. A freshly painted exterior and exceptional curb appeal make this a home you'll love coming back to.A beautiful, wide, and gracious foyer sets the tone as you enter. Inside, the main living area is spacious and inviting, centered around a classic wood-burning fireplace, perfect for cozy evenings. Sun-filled rooms, a flexible den/sunroom, and a generous layout create an ideal setting for both everyday living and memorable gatherings.


63 Photos
413 REAL ESTATE
$429,900
3 BD | 2 BA
Residential - Single Family

Welcome home to this charming and thoughtfully updated 3-bedroom, 1.5-bath property that blends classic character with modern comfort. Gleaming hardwood floors flow throughout, leading you into a living room featuring a cozy fireplace. The dining room exudes charm with beautiful built ins and the kitchen impresses with rich cherry cabinets, granite countertops, and a distinctive tin ceiling that adds a touch of unique craftsmanship. Quality finishes adorn the updated full bath and the finished lower level adds additional flexible living space and half bath. A heated sunroom offers year-round enjoyment and overlooks a patio, fenced area and shed in the spacious backyard. This home reflects pride of ownership and attention to detail throughout--ready for you to move in and enjoy.


27 Photos
BIRCH PROPERTIES
$433,000
3 BD | 2 BA
Residential - Single Family

Located in the desirable Clayton section of New Marlborough, this 3-bedroom, 2-bath home offers a rare opportunity to own 7.2 acres with 383 feet of frontage on the Konkapot River. The property features a natural setting with direct river access and plenty of room to make it your own.The home has a functional layout with three bedrooms and two full baths. While move-in ready, it would benefit from updating and general maintenance. Being sold as-is.Conveniently located near the Connecticut border--just minutes to Canaan, CT, and a short drive to downtown Sheffield and other Southern Berkshire attractions.Enjoy the natural beauty and quiet charm of the Berkshires with the potential to customize and enhance this well-located property.


36 Photos
THE KINDERHOOK GROUP
$433,700
2 BD | 1 BA
Residential - Single Family

Imagine starting your mornings with coffee on the deck and ending your evenings under the open sky. This charming 2 bedroom, 1 bathroom home offers the perfect balance of comfort and simplicity, with inviting indoor spaces and Excalibur Lake front views. Whether you're looking for a peaceful retreat or a place to gather with loved ones, this home is designed for entertaining and making memories. With a history of short-term rental use, this home presents a unique opportunity for those seeking both a personal retreat and income potential. 10 minutes from Jacobs Pillow Dance Festival. Boat, Swim, Relax-Repeat! Everyday feels like a vacation in this ranch home.


60 Photos
KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$434,900
3 BD | 5 BA
Residential - Single Family

Step inside to find an inviting ranch-style home set on 15 acres of peaceful, private land, offering the perfect blend of comfort and tranquility. This home offers an EXCEPTIONAL layout, centered around a well appointed kitchen with stone countertops, ample cabinetry, stainless appliances & a kitchen island-blending seamlessly into an oversized family room showcasing a beautiful gas fireplace. Complemented by a formal dinning room and family friendly living room with sliders leading to the new composite deck over looking a fully fenced area for kids and pets to play and enjoy! Featuring three bedrooms, including a lovely primary en-suite complete with a custom shower, jetted tub & walk-in-closet. First floor laundry room, half bath with entry/mudroom area complete the main level


42 Photos
BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
$435,000
3 BD | 2 BA
Residential - Single Family

Welcome to 184 Washington Mountain Rd -- an inviting three-bedroom, one-and-a-half bath raised ranch ideally situated in a quiet, highly desirable location. This thoughtfully updated home features a stylish eat-in kitchen that flows seamlessly into a bright, open living area with direct access to a sunroom, creating the perfect space for relaxing or entertaining year-round. Beautiful hardwood floors add warmth & timeless appeal throughout the main level. The primary suite offers the convenience of a private ensuite half bath, while the finished lower level provides versatility with a spacious family room & dedicated office area. Outside, a generously sized backyard offers ample space for outdoor enjoyment. A rare opportunity to enjoy comfort, space, and location in one exceptional home.

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