Stone House Properties

06/04/2026

Classic lakefront cottage with frontage on quiet Benton Pond plus deeded rights to Big Pond.

https://stonehouseproperties.com/properties/98-loop-dr-otis-ma-01253-20260421155032865884000000

Four season contemporary Cape with an open plan featuring a window wall facing the lake and a brick fireplace. There are three bedrooms and two full baths plus a small loft. The screened porch is next to the kitchen, convenient for al fresco dining. Exterior access to the basement is perfect for storage of your canoes and kayaks. The home is located on over an acre and is the 2nd to the last on the road so very quiet. Less than 3 hours to NYC and 2 1/2 to Boston, near Tanglewood, Jacobs Pillow and most other Berkshire cultural attractions, as well as several state forests. If you have been looking for a reasonably priced lake home, this is your chance.

📍 98 Loop Dr, Otis
Offered at $698,500 by Jeff Wilkinson

06/02/2026

We’re proud to have supported the Red Tee Tournament this week! Thanks .realestate for the photo ⛳️

05/28/2026

Welcome to this thoughtfully designed home with south facing views on 3 serene acres.

https://stonehouseproperties.com/properties/21-stone-house-road-canaan-ny-12029-20250916150230165660000000

The home was constructed by a local builder and offers a perfect blend of luxury and privacy. Situated on the Canaan/New Lebanon line, it boasts breathtaking views and an in-ground pool ideal for relaxation and entertainment on the blue stone patio. The spacious first-floor primary suite provides a peaceful retreat, complete with large windows that frame the stunning surroundings, and a freshly updated en-suite bath. Enjoy cooking in the large EIK that's open to the dining area. Relax after a meal by the fireplace in the living room. First floor half bath and laundry along with a gracious, welcoming mud room complete the first floor. Upstairs you'll find a another bedroom, full bath, and large landing which is currently an office. Over the garage (which you can access from the landing) is a guest suite with a kitchenette, bedroom, living area, and bathroom with it's own exterior entrance. A new engineered slate roof with a @ 50 year life span offers a peace of mind. Whether you're looking for a tranquil escape or a home that blends comfort with style, this property offers both privacy and a high standard of living in a desirable area near restaurants, shops, farms for amazing fresh food, 20 minutes to Jiminy Peak, 25 minutes to Tanglewood, close to museums, and so much more!

📍 21 Stone House Road, Canaan NY
Offered at $1,200,000 by Melissa DiMassimo of Stone House Properties, LLC

05/26/2026

Uniquely and tastefully renovated one-bedroom end unit condo with open living concept, and fully furnished! (some artwork excluded)

https://stonehouseproperties.com/properties/64-churchill-crest-pittsfield-ma-us-01201-20260510145516245747000000

Great room with fireplace, recessed lighting, ceiling fans, quartz counters, stainless appliances, programmable under cabinet multi color lighting, microwave with expandable exhaust vent, modern bathroom with double shower, swanstone vanity sink, built in cabinet.... Simply move in and live! New central air conditioner in 2012 and new hot water heater in 2015. Pretty laminate floating floor throughout, recessed lighting throughout all with dimmer controls, 7-day programmable thermostats in each room, extra quiet Kitchenaid dishwasher, all soft close upper and lower kitchen and bathroom cabinets, kitchen pullouts, 5-burner Kenmore stove, GE refrigerator with inside water dispenser, detached garage with automatic opener and keypad entry, extra storage unit, big entertaining pavilion and heated inground pool, and low, low HOA fees!

📍 64 Churchill Crest, Pittsfield
Offered at $260,000 by Susan Calkins of Stone House Properties LLC

05/25/2026

This is an exceptional opportunity to own a fully occupied, income-producing Victorian multifamily property set on 2.5 beautifully landscaped acres in a highly desirable South County location.

https://stonehouseproperties.com/properties/465-chapel-st-lee-ma-us-01238-20260519111219623375000000

Combining classic charm with strong rental performance, this property is ideal for investors seeking both stability and long-term potential. The building features a total of nine residential units, thoughtfully configured to attract a diverse tenant base. There are two efficiency one-bedroom units, one spacious two-bedroom unit, and six standard one-bedroom units, each offering a comfortable layout with a living room and full kitchen.

The property is currently fully occupied, providing immediate and consistent rental inco Its strong occupancy history and appealing unit mix contribute to long-term tenant retention and investment reliability.

The grounds are beautifully landscaped, enhancing curb appeal while offering a pleasant environment for residents. The expansive 2.5-acre lot provides a sense of privacy and space that is rarely found in multifamily properties of this size.
Additional amenities include private parking for up to 16 vehicles, ensuring convenience for tenants, as well as a coin-operated washer and dryer that generates supplemental income. A storage shed is also located on the property, offering space for maintenance equipment or tenant use.

📍 465 Chapel St, Lee
Offered at $995,000 by Tim Gallagher/Berkshire Realtor

05/23/2026

Step into a piece of living history with this beautifully preserved 1915 home, perfectly situated on a private 12.5-acre parcel.

https://stonehouseproperties.com/properties/2999-new-york-23-hillsdale-ny-us-12529-20260512122746843777000000

Offering four generous bedrooms and three baths (2 full, 1 Half), this classic residence blends timeless charm with everyday comfort, creating an ideal setting for family living, weekend escapes, or peaceful country entertaining.

Outside, the grounds are nothing short of spectacular with flower beds are scattered around the house and front yard. Cool off in the sparkling in-ground pool, relax by the tranquil pond, or follow the gentle sounds of the year-round stream that flows along the property. The magnificent 1800s post-and-beam barn stands ready for your vision, whether as a workshop, artist studio, equestrian space, or rustic gathering spot.

Located just a stone's throw from Catamount Ski Mountain, this property minutes away from skiing, snowboarding, and year-round mountain recreation right at your doorstep. In warmer months, enjoy hiking trails, scenic drives, and the vibrant cultural scene of nearby Hudson and Great Barrington.

📍 2999 Route 23, Hillsdale, New York
Offered at $725,000 by Tyler Bervy and Nikki Carchedi Of Stone House Properties

05/22/2026

Open House! See 1963 County Route 5 in Canaan, NY tomorrow (5/23) from 11AM-1PM.

Set in the foothills of the Berkshires, this beautifully restored 1930s cottage blends timeless character with thoughtful modern updates. The sleek, updated kitchen and baths complement the home’s original warmth and charm, creating an inviting balance of old and new.

Surrounded by five picturesque acres of mature trees and established gardens, the property feels both peaceful and deeply rooted in its setting. A classic rocking-chair front porch welcomes you home, while the screened porch overlooks the backyard — the perfect spot for quiet mornings, summer evenings, or gathering with friends after a day in the garden.

Inside, the home offers three bedrooms and two baths, office/den along with rich details that make farmhouse living so enduringly appealing: a wood-burning fireplace, a cozy wood stove in the kitchen, and a charming pantry that feels pulled from another era. Warm, comfortable, and full of personality, this is a home that invites you to slow down and stay awhile.

Offered at $699,000 by Nikki Carchedi Of Stone House Properties: (413) 822-0200

05/22/2026

05/21/2026

Welcome to Peggy's Cottage. The owner, a cellist, originally chose this Queechy Lake home for its proximity to Tanglewood and the cathedral ceilings in the family room, which served as her music room. She quickly grew to love the lake community's friendly neighbors, walking trails, and private beach.

https://stonehouseproperties.com/properties/34-queechy-shore-beach-road-east-chatham-ny-us-12060-20260517110557664693000000

This cozy log cabin sits on a level .36 acre lot, offering rare privacy with lovely gardens, a latticed entertainment deck, and two sheds. Relax in the living room in front of the stone fireplace, perfect for a quiet conversation or reading. Step into the spacious family/music room and enjoy movie night and the view of the gardens. The open kitchen and dining area connect to a first-floor bedroom with laundry and a full bath. Upstairs, you will find two large bedrooms with skylights and generous closets, including a primary bedroom with ensuite bath and a Juliette balcony. The second bedroom accesses the bath via a hall entry. Key updates include a new roof and boiler, both replaced in 2025.

The Queechy Shores Beach Association provides members with access to a boat launch, a dock, a private beach, and a recreation pavilion. Association rules restrict rentals to a minimum of 30 days.

📍 34 Queechy Shore Beach Road, East Chatham NY
Offered at $529,000 by Nancy Cuddihy