Stone House Properties

Stone House Properties Celebrating 40 years, Stone House Properties is committed to our clients and local community. Every transaction is treated as if it were our own.

The sale or purchase of real estate is one of the most significant financial decisions that we make in our lives. As Realtors, our knowledge, diligence, integrity and attention to detail must be extraordinary. From our dedication to that simple principal, Stone House Properties has become a premier real estate company in the Berkshires. We enjoy the respect of not only of our buyer and seller clie

nts, but the lawyers, bankers, land planners and other professionals in the real estate industry as well as our colleagues in other real estate companies. Our family of Associates includes the highest percentage of licensed Brokers, not just licensed Agents, of any company in the Berkshires and all are dedicated to our tradition of excellence.

Investment opportunity near downtown Pittsfield. This renovated 7,904-square-foot commercial building is situated on app...
09/03/2026

Investment opportunity near downtown Pittsfield. This renovated 7,904-square-foot commercial building is situated on approximately 0.72 acres in the Downtown Creative District and is currently leased to an established daycare/school operator through August 2031.

https://stonehouseproperties.com/properties/41-wendell-ave-pittsfield-ma-us-01201-20260902121839836576000000

The property generates an annual base rent, plus documented reimbursements for real estate taxes, insurance, and water/sewer expenses.The building offers approximately 3,952 square feet on each of two levels, with an open, adaptable layout suitable for educational, nonprofit, institutional, professional, or community-oriented uses. Improvements include central HVAC, replacement windows, sprinkler and fire-alarm upgrades, and extensive interior renovations. An elevator provides convenient access between floors. With long-term tenancy, immediate income, and a flexible commercial configuration, 41 Wendell Avenue presents an attractive opportunity for investors, including those completing a 1031 exchange. Its central Pittsfield location and Downtown Creative District zoning further enhance the property's long-term investment potential. Property for sale only, business is not for sale.

๐Ÿ“ 41 Wendell Ave, Pittsfield MA
Offered at $890,000 by Tim Gallagher

Take a fresh look at this vintage Queechy Lake cottage. Built in 1920, this home has been carefully updated and winteriz...
09/02/2026

Take a fresh look at this vintage Queechy Lake cottage. Built in 1920, this home has been carefully updated and winterized, while retaining its original charm.

https://stonehouseproperties.com/properties/13-tremper-association-road-east-chatham-ny-us-12060-20260525170454592019000000

The one-acre setting offers rare peace and privacy with room to grow. Sitting on the cozy front porch feels like being in a tree house. This 4-season home features hardwood floors, a great room with cathedral ceiling, kitchen with dishwasher and washer & dryer, two bedrooms, and one bath. A sweet shed stores your kayak and bike. Located just a short walk from the water's edge, the property includes deeded access to the waterfront for fishing and boating. Join the Adams Point Beach Club for a lifeguard-protected beach and swim lessons for the kids. The cottage is ideally located 15 minutes from Tanglewood Music Festival, and an easy drive to Berkshire attractions including hiking trails, Mass MOCA, Clark Art Institute, Jacob's Pillow, fine dining, regional theater and two ski resorts.

๐Ÿ“ 13 Tremper Association Road, Canaan NY
Offered at $459,000 by Nancy Cuddihy

Nestled on 7.79 private mountaintop acres, this distinguished 1916 Italianate Berkshire Cottage sparkles with original a...
09/01/2026

Nestled on 7.79 private mountaintop acres, this distinguished 1916 Italianate Berkshire Cottage sparkles with original architectural details, beautiful fireplaces throughout, and a stunning reflection pool surrounded by mature gardens.

https://stonehouseproperties.com/properties/720-south-st-pittsfield-ma-us-01201-20250503215358499020000000

Four spacious bedrooms include a luxurious primary suite with sitting room, while the grand great hall creates perfect spaces for both intimate gatherings and gracious entertaining. The lower level features an elegant one-bedroom guest apartment plus a separate catering kitchen, utility rooms and two one car garages, while the main house enjoys lovely terraces facing south, east and west. Surrounded by 200 protected acres near world-class Tanglewood - your own slice of paradise where old-world charm meets mountain-top serenity! In 1916, renowned patron of the arts Elizabeth Sprague Coolidge commissioned this magnificent 4-bedroom mountain house atop South Mountain in Pittsfield as a gift for her son Albert. This stunning stucco Italianate Berkshire cottage sits gracefully on 7.79 acres of pristine woodland, offering both grandeur and intimate charm.

The heart of the home features a dramatic great hall with soaring spiral stairs that create an impressive architectural centerpiece. Multiple fireplaces throughout provide warmth and ambiance, while the library boasts a wet bar perfect for entertaining. A dedicated game room offers space for leisure and recreation, complemented by a thoughtfully designed guest wing that ensures privacy for visitors.

The lower level houses a completely self-contained one-bedroom apartment, while a separate catering kitchen provides professional-grade culinary facilities. Two single-car garages offer practical storage alongside multiple utility and storage rooms that provide ample space for estate maintenance and organization. A lower level parking area provides additional vehicle accommodation beyond the garages. Above, a large attic provides generous additional storage space.

The mature woodland gardens showcase spectacular rhododendrons and hydrangeas that bloom in seasonal splendor. A serene reflection pool anchored by carefully manicured boxwood gardens creates a peaceful focal point for contemplation and outdoor entertaining.

The property enjoys a unique position adjacent to 200 protected acres managed by the South Mountain Concert Society, ensuring perpetual privacy and natural beauty. Following the Coolidge era, the estate became home to Willem Willike and his wife Sally, who cherished its artistic heritage. In 1992, the Miller family acquired this remarkable property, continuing its legacy as a treasured Berkshire retreat.

This extraordinary estate represents more than a century of careful stewardship, combining Elizabeth Sprague Coolidge's vision for artistic patronage with the timeless appeal of Berkshire mountain living.

๐Ÿ“720 South St, Pittsfield
Offered at $1,525,000 by Scott Sawyer and Mandy Victor-Pieczarka

This breathtaking timber-frame home was listed by Randy Thunfors & Susan Calkins of Stone House Properties LLC, and sold...
08/29/2026

This breathtaking timber-frame home was listed by Randy Thunfors & Susan Calkins of Stone House Properties LLC, and sold by Melissa DiMassimo of Stone House Properties, LLC! Thanks to all of our team for always doing the best for your clients.

There's only one day left in the nomination period for Best of the Berkshires! If you'd like to cast a vote for Stone House, or one of our agents/brokers, you can do so by clicking here: https://berkshire-eagle.votebestof.com/b/berkshires-readers-pick-2026/c/realty-company?ref=share&via=voter

Check out the property of the week, listed by Nikki Carchedi Of Stone House Properties!
08/28/2026

Check out the property of the week, listed by Nikki Carchedi Of Stone House Properties!

Nikki Carchedi of Stone House Properties offers the kind of country home that invites you to settle in and stay awhile. If you are ready to consider selling the family home and moving into smallerโ€ฆ

08/27/2026
Open House! Come see 19 Terrace Dr  on Saturday, 8/29 from 11AM-12:30PM.https://stonehouseproperties.com/properties/19-t...
08/27/2026

Open House! Come see 19 Terrace Dr on Saturday, 8/29 from 11AM-12:30PM.

https://stonehouseproperties.com/properties/19-terrace-dr-new-lebanon-ny-us-12125-20260825125109826627000000

Colonial with a View! This beautifully situated four-bedroom, 2.5-bath Colonial offers a bright, open-concept floor plan and peaceful country setting. The spacious primary suite features a walk-in closet and private bath, with three additional bedrooms providing plenty of room for family and guests. Enjoy seamless indoor-outdoor living with a large deck overlooking the above-ground pool and surrounding views. The walkout lower level offers additional flexible space. Two garages, one attached and one detached, provide ample parking and storage. A whole-house generator adds peace of mind. Ideally located just 10 minutes from downtown Pittsfield and approximately 25 minutes to Albany, this home offers the perfect balance of privacy and convenience.

๐Ÿ“ 19 Terrace Dr, New Lebanon, NY
Offered at $519,999 by Elisha Poirier with Stone House Properties LLC

Charming, move-in ready, and full of possibilities, this 3-bedroom, 1-bath home offers 1,428 square feet of comfortable ...
08/23/2026

Charming, move-in ready, and full of possibilities, this 3-bedroom, 1-bath home offers 1,428 square feet of comfortable living space.

https://stonehouseproperties.com/properties/1303-north-st-pittsfield-ma-us-01201-20260727175756768450000000

Inside, you'll find a bright and inviting layout with beautiful hardwood floors, an updated kitchen with plenty of cabinet and counter space, and a spacious upstairs that offers flexibility for bedrooms, a home office, or additional living space. Set on a manageable 0.18-acre lot, the property also offers a nice yard with room to relax, garden, or entertain. A great option for first-time buyers, those looking to downsize, or anyone searching for a home that's ready to enjoy from day one. Come see all this sweet property has to offer!

๐Ÿ“1303 North St, Pittsfield
Offered at $219,000 by Heather Gallagher, Berkshire Realtor and Tim Gallagher/Berkshire Realtor

Prime Downtown Lenox Retail Opportunity.https://stonehouseproperties.com/properties/27-church-st-lenox-ma-us-01240-20260...
08/22/2026

Prime Downtown Lenox Retail Opportunity.

https://stonehouseproperties.com/properties/27-church-st-lenox-ma-us-01240-20260817183901895753000000

Position your business in the heart of downtown Lenox, one of the Berkshires' most desirable shopping and cultural destinations. This street-level retail space enjoys excellent visibility in a high-traffic area, with oversized display windows that provide abundant natural light and outstanding merchandising and branding opportunities. The flexible, open layout can accommodate a boutique, gallery, showroom, wellness studio, specialty retailer, or service-oriented business, subject to local approvals. Dedicated storage areas add practical functionality while preserving valuable customer-facing space. Surrounded by popular shops, restaurants, lodging, and cultural attractions, this location benefits from strong pedestrian and vehicle traffic generate by year-round residents and seasonal visitors. A rare opportunity to establish or expand your business in the vibrant center of Lenox, Massachusetts.

๐Ÿ“ 27 Church St, Lenox
Offered at $3,800/month by Tim Gallagher/Berkshire Realtor

Address

38 Main Street
West Stockbridge, MA
01266

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