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34 Photos
HARSCH ASSOCIATES

This remarkable investment opportunity in the heart of the historic town of Bennington offers the future owner two beautifully and totally updated and restored historic 19th century buildings with plenty of style, character, and multiple options. The prominent North St. location stands out to the 8,000-12,000 daily traffic count passing by assuring outstanding visibility. Continue leasing to the existing business or locate a new business or professional office here while also receiving the income from the leased building next door housing a locally famous deli. 125 North St. contains 2,225 SF on two floors plus attic and full basement, all renovated in 2001. Also completely renovated in 2001, 100 Pleasant St. contains 1,500 SF on two floors.


55 Photos
COHEN & WHITE ASSOCIATES
$599,000
3 BD | 3 BA
Residential - Single Family

Prime location just a short distance to Stockbridge Village, Tangelwood, Berkshire Theatre Group and many more cultural attractions here in the beautiful Berkshires. Sprawling backyard with Housatonic River views. Open common spaces with ample space, exposed beams, character and wood flooring. The second level offers two bedrooms, full bath, large landing flex space and office/sitting area. Additionally there is an attached first floor In-law apartment with living room, kitchen, bedroom and full bath. Included with the house is a multi level barn with electricity. Lovely setting to relax on the back deck and take in the views or stroll into town to enjoy the cultural amenities This gem has great potential and is ready for the new owners vision


11 Photos
STEEPLEVIEW REALTY - N. ADAMS
$599,000

Commercial

Property on corner of busy 4 way stoplight in the heart of town with 256 ft of frontage. High visibility and high traffic count: 11,777 on average. Multi-zoned for multiple different uses & possibilities. The source of all representations are from the seller or a public source; broker has not verified same. It is recommended that buyer independently verify all information.


50 Photos
LAMACCHIA REALTY, INC
$599,000
3 BD | 3 BA
Residential - Single Family

Welcome to this spacious and light-filled home just moments from scenic Pontoosuc Lake! Enjoy breathtaking sunrises and sunsets from your open-concept upper level, featuring soaring ceilings and expansive windows that fill the space with natural light. The beautifully updated kitchen offers ample room for dining and entertaining, complete with a breakfast bar and generous seating options--all perfectly positioned to enjoy the peaceful surroundings. The oversized primary bedroom boasts a flowing layout and a large walk-in closet, creating a serene retreat. Downstairs, the expansive lower level offers endless potential--ready to be finished to suit your style and needs.


67 Photos
RED HORSE REAL ESTATE
$599,000
3 BD | 2 BA
Residential - Single Family

Country Farm: Sixty Acre cattle Farm. Remodeled country Home with beautiful open fields and Yokum Brook running through the back lot were the cows use to sip cool water and graze. The farm consists of 5 different parcels of land with the barn across from the main house. You'll find a modern Kitchen and bath. The main Bedroom has a low deck and full-length windows looking out to the pastures and Apple trees were deer frolic and feed. A rock count yard with a fireplace and trellises holding grapevines makes a lovely entertainment area Most of the land is open fields.The barn has two garages, and the lower level has a feeding station. A shop and 2 hay lofts Although the cows are gone the farmer remains in the home, please respect his privacy. Showing by request only.


9 Photos
ASHMERE REALTY, INC.

Discover the ultimate blend of privacy, natural beauty, and waterfront living with this exceptional offering of three lots totaling over 60 acres. Included is an 11-acre waterfront parcel on the serene shores of Ashmere Lake--perfect for boating, fishing, or simply soaking in the views. Whether you're envisioning a private estate, family compound, or future development, this expansive property offers endless possibilities. All three lots are being sold together as one parcel, ensuring unmatched scale and potential in a coveted location. There is a deeded right of way through Lot #14. There is a sewer betterment fee for Lot#15.


51 Photos
MACCARO REAL ESTATE
$599,000
4 BD | 2 BA
Residential - Single Family

Introducing the Beautiful Spacious Ranch in a Great Neighborhood! Easy Living at Its Finest! Key Features:- Prime Location: Close to Main St.- Impeccably Maintained & Beautifully Updated- Stylish Granite Countertops for a Touch of Elegance- Lower Level Living Area/In-Law Unit, Extra Space for Guests or Rental Income Opportunity, Second Kitchen with Cozy Eat-In Area, Spacious Living Room for Entertaining, Large Bedroom & Full Updated Bathroom with Walkout Access.


1 Photos
STEEPLEVIEW REALTY - N. ADAMS

Property on corner of busy 4 way stoplight in the heart of town with 256 ft of frontage. High visibility and high traffic count: 11,777 on average. Multi-zoned for multiple different uses & possibilities. The source of all representations are from the seller or a public source; broker has not verified same. It is recommended that buyer independently verify all information.


31 Photos
SIGNATURE ASSOCIATES
$599,000
4 BD | 3 BA
Residential - Single Family

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 beauty of the Berkshires awaits, just beyond your backyard.


17 Photos
413 REAL ESTATE
$599,900
12 BD | 12 BA
Multi-Family

Rare opportunity to purchase three duplexes (six total units) in a package deal. All units have separate utilities paid by tenants,. Low-maintenance property with ample off-street parking, conveniently located near downtown shops, restaurants, and schools. A solid turnkey investment--call today to schedule a showing!


45 Photos
PAULA MCLEAN REALTORS INC.
$599,900
3 BD | 2 BA
Residential - Condo/Townhouse

Welcome to South Pond Farm Condominiums, a serene waterfront community nestled on the shores of Richmond Pond. This beautifully maintained residence offers effortless living with the perfect blend of privacy, comfort, and natural beauty.Enjoy woodland views, an inviting interior, and access to exclusive community amenities -- including a private beach, tennis, pool, and walking trails. Whether you're seeking a peaceful year-round home or a Berkshire getaway, South Pond Farm is your invitation to relax, unwind, and live surrounded by nature's finest.Experience lakeside living at its best -- just minutes from Tanglewood, Lenox, and the cultural heart of the Berkshires.


7 Photos
GILCREST PROPERTIES
$599,900

Commercial

A river runs through it. Incredible opportunity awaits its new owner! Fortune favors the brave. So much is happening in the Hudson Valley of NY! It an exciting time! Do you have the vision for this 1.9 acre industrially zoned parcel located within the Village of Chatham? Water and sewer available. Gorgeous location for a brewery, distillery, cidery adjacent to the babbling brook. The dam is also included in this sale. Self storage facility, warehouse facility and so many more options. Call today for your private showing.


38 Photos
LANCE VERMEULEN RE, INC
$600,000
6 BD | 5 BA
Multi-Family

A prime investment opportunity in the heart of downtown Great Barrington. This 5-unit residential property features a desirable mix of four one-bedroom apartments and one two-bedroom unit. A significant advantage for this building is that all units are serviced by their own separate heating and electrical systems. Its convenient downtown location ensures high demand due to walking proximity to grocery stores and the hospital, while ample on-site parking provides a crucial amenity for all residents. Adding to its value, a detached garage/workshop offers the flexibility to be rented separately for additional income or used as a storage amenity for tenants.


30 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$600,000
3 BD | 4 BA
Residential - Single Family

Waterfront living at it's finest at desirable Long Lake. The main reason owners love Long Lake is because it is truly the only waterfront community in Columbia County which offers maintenance free living. The HOA takes care of all exterior maintenance such as snow plowing, landscaping, pool and amenities upkeep which leaves you with the job of enjoying your free time on the screen porch, kayaking, swimming, or enjoying the Hudson Valley and the Berkshires. This 3 bedroom 3 bath property is also quite special because it is an end unit and it is close to all of the amenities such as swimming, tennis, and the community beach. Beautifully designed by architect Steve Haas, this home features two levels of floor to ceiling windows, a sublime screened porch with cathedral ceiling, and large


48 Photos
PAULA MCLEAN REALTORS INC.
$600,000
3 BD | 3 BA
Residential - Condo/Townhouse

Welcome to 5D Lakeside at Foxhollow - a beautifully updated 3-bedroom, 3-full-bath condo offering the perfect blend of modern comfort and classic Berkshire charm.Enjoy seasonal views of sparkling Laurel Lake from your enclosed summer porch, the ideal spot for morning coffee or evening gatherings. Inside, you'll find a thoughtfully updated kitchen and baths, a cozy wood-burning fireplace, and generous living space designed for both relaxation and entertaining. This sought-after community offers a wealth of amenities including an outdoor pool, Har-Tru tennis courts, and private water frontage on Laurel Lake -- complete with kayak and canoe storage for easy days on the water. Perfectly situated just minutes from Lenox, Stockbridge, Tanglewood &, Jacob's Pillow.


26 Photos
STONE HOUSE PROPERTIES, LLC
$609,000
4 BD | 3 BA
Residential - Single Family

New England farmhouse with distant views. Large common rooms & kitchen great room are bathed in sunlight. Beautiful pine floors & exposed beams throughout the 1st floor. Extra room on the first floor can be used as a bedroom or an office (not pictured.) Many structural renovations in 2004, central air, in line generator, in ground pool, screened porch & so much charm. The flat 3.89 acres allows for accessory buildings, pickleball court, etc. Easy bike ride to town. This is the home you've been looking for.


19 Photos
BIRCH PROPERTIES
$610,000
1 BD | 2 BA
Residential - Condo/Townhouse

Loft 208 at Greylock WORKS is a beautifully proportioned 1BR | 1.5BA + Study Berkshires residence set within the region's most celebrated mill conversion, offering 1,150 SF of refined, light-filled living. With 12.5-foot ceilings, expansive volume, and an elegant L-shaped living and dining area, the home blends the character of the original mill with elevated contemporary detailing to create a warm and versatile modern loft.The open kitchen and main living space feature restored hardwood floors, hand-burnished structural elements, and regionally sourced schist countertops selected to heighten the building's material richness.


23 Photos
HOUSATONIC REAL ESTATE
$610,000
3 BD | 1 BA
Residential - Single Family

OPEN HOUSE SAT 13TH 12-2:00. A beautifully renovated one-level ranch offers the perfect blend of modern convenience and cozy charm. With 3 spacious bedrooms and a well-appointed bathroom, this home is designed for comfort and easy living. Step inside to discover a sunlit living space showcasing modern upgrades throughout, including energy-efficient fixtures and a sleek, new kitchen equipped with top-of-the-line appliances. The open floor plan is perfect for entertaining, seamlessly connecting the living, dining, and kitchen areas.One of the highlights of this home is its commitment to sustainability, featuring solar panels that significantly reduce energy costs. Lots of outdoor space and 2 separate outbuildings with car port. Additional plans available. Separate Screened in porch


51 Photos
LAMACCHIA REALTY, INC
$619,900
3 BD | 2 BA
Residential - Single Family

Welcome to 106 Stoney Brook Road in the hills of Becket Massachusetts. This 3 bedroom 2 bath ranch offers an open concept living area including a spacious living room with pellet stove, eat in kitchen, and den just filled with natural light. The main floor offers a generously sized primary en suite complete with custom shower and walk-in closet. An additional 2 bedrooms and a full bath nicely round out the first floor. A partially finished basement adds to the charm and space within this beautiful home. On the exterior you will find a large deck off of the kitchen that overlooks the private and peaceful yard complete with fire pit that is perfect for anyone looking for a serene retreat that is minutes from many local attractions. You won't want to miss this beautiful home!


47 Photos
ASHMERE REALTY, INC.
$625,000
3 BD | 2 BA
Residential - Single Family

Escape to nearly 40 acres of serene privacy with this inviting log cabin retreat nestled just minutes from Ashmere Lake. This home offers the perfect blend of cozy living and future potential: Three bedrooms and two full baths provide ample room for family or guests. The unfinished second-floor primary suite is ready for your personal touch--create the ultimate sanctuary with views of the surrounding forest. Warm wood tones, rustic beams, and timeless craftsmanship make this home a true Berkshire gem. Whether you're seeking a year-round residence, a weekend getaway, or a homestead with room to grow, this property delivers privacy, character, and potential in one unforgettable package.

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