Otis Classified Ad Listings

11 Prospect Hill Rd Apt 8. Some Berkshire homes are simply places to live. Others become part of the way you want to live. The Oronoque Villas are among those rare places. Built in the mid-1990s on the historic grounds of Oronoque--one of Stockbridge's great Berkshire cottages--just eight freestanding villas were thoughtfully sited within the estate landscape, complementing the original mansion...

Deer Run Lot 35. Very private wooded lot at the end of the cul de sac in the Deer Haven community (HOA). Bargain priced estate sale, being sold as is. Buyers to do their own due diligence. No camping or RV use per town bylaws.

2 Goodrich St. Contemporary home built in 2012 on over 11 acres walking distance to Stockbridge center. Original house was taken down and this sun-drenched home was built on the saved footprint. Main floor has a small living area off the entry open to large kitchen and dining with sliders to the deck, primary suite with walk-in closet and deck access, 1/2 bath and access to the oversized garage...

70 Riverton Rd. Escape the hustle and discover your own private retreat at 70 Riverton Road. Nestled on a hillside in the quiet and picturesque town of Riverton, this beautifully renovated raised ranch offers the perfect blend of tranquility, comfort, and modern living. Featuring 3 bedrooms and 3 full bathrooms, the home has been completely updated from top to bottom with stunning new finishes ...

Summit Hill Rd Lot 3. Opportunity awaits on this stunning approximately 15-acre parcel nestled in the scenic hills of Washington. Tucked away along Summit Hill Road, this property offers a rare blend of privacy, natural beauty, and future potential. Surrounded by mature woods and peaceful landscapes, this expansive lot is ideal for building your dream home, private retreat, or long-term investm...

2336 W Center Rd. 9 PRIVATE ACRES, 2,700 SQ. FT. OF LIVING SPACE and EVEN MORE POTENTIAL!If you've been searching for a home that offers space, privacy, beautiful scenery, and room to grow, this is one you won't want to miss! Nestled on 9 breathtaking acres, this beautifully maintained home features 3 spacious bedrooms, each with its own private en-suite bathroom, offering the perfect combinati...

153 Hurlburt Rd. Nestled on a highly desirable road in Great Barrington, this unique acre-plus property offers a rare opportunity to create your Berkshire retreat. The land features two existing structures with endless possibilities. A detached two-car garage includes a rear room, ideal for a workshop, studio, or flex space, plus a second level for additional storage. The property's historic fo...

453 Elm St. A Little Whimsy, A Lot of Wow! Step into a bungalow bursting with personality, where timeless Craftsman charm meets thoughtfully curated updates, playful color, and extraordinary style! Beautifully reimagined while preserving its solid bones and original character, this home is anything but ordinary. A gorgeous new kitchen with stainless steel appliances and an island flows into a d...

1415 Canaan Southfield Rd. 3 BR 2 Bath Home with tons of storage and lots of space. Great opportunity for a small homestead or someone looking for a home with shope space and outbuilding. BEING SOLD AS IS. 3 Bedrooms. 2 Bathroom. 1564 ft

1427 Canaan Southfield Rd. Charming cottage-style home that offers far more space than meets the eye! The first floor features a spacious kitchen with abundant cabinet storage, pantry space, and a newer gas range, along with a cozy office nook, dining room, living room, full bath, two bedrooms, laundry room, and an inviting den. Upstairs offers three additional rooms, including two bedrooms, pr...

752 State Rd. 37-acre, ROCK RIDGE FARM, with early mid 20th century roots. Built in 1785, steeped in local history, Property has remained a working and residential farmstead today and reflects the regions long tradition of working farms. Offering a blend of local heritage and timeless New England character. Along with the main house there are several outbuildings that could be renovated, repurp...

48 Brown St. Opportunity knocks! This 4-family property has suffered significant fire damage and is being sold as-is for land value. Ideal tear down project with endless redevelopment potential. The lot includes a detached garage and offers ample space for new construction. Bring your vision and rebuild in a growing area with strong rental demand. Cash or construction financing only.. 12 Bedroo...

9 October Hill Dr. Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fi...

1 Devon Rd. A significant price reduction has just been made on this terrific revenue opportunity property in Stockbridge. The historic General Williams House (circa 1795) has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. THIS PROPERTY HAS AN EXCELLENT HISTORY OF RENTAL INCOME. The ''Ice House'...

500 Williams St. A remarkable turn-of-the-century Colonial where timeless architecture, meticulous care, and gracious proportions come together beautifully. Set against a backdrop of sweeping Berkshire views, the home captures a sense of elegance and permanence rarely found today. Rich in character yet beautifully suited to modern living, this is a home that feels as extraordinary as its settin...

66 Access Rd. Opportunities are right outside your door: Cool off in the community swimming pond after playing a few games of tennis on the two clay courts or after taking a hike within the community. Come back to the tastefully designed main home perfect for friends with an open plan kitchen/living space with 3 bedrooms. The stunning attached conditioned barn with grand vaulted ceiling and rus...

110-112 Lenox Ave. Unlock the potential in this spacious two-family property ideally located near Berkshire Medical Center, local schools, and downtown Pittsfield amenities. Perfect for experienced renovators and investors, this property offers tremendous opportunity to restore and build equity. The lower unit features two bedrooms and a well-designed kitchen with a functional layout, though th...

4 Stockbridge Rd. Nestled in the heart of West Stockbridge, this stunning 5-bedroom, 5.5-bath Federal/Greek Revival style home at 4 Stockbridge Road combines historic charm with modern luxury. Built in 1825, the residence has been beautifully renovated, maintaining its classic character while offering contemporary amenities. The spacious interior features generous living areas, perfect for fami...

8 Phelps Rd. 1988 Reproduction Garrison Colonial privately set on 2.3 acres in Colebrook. 2,592 square feet; high ceilings; 3 bedrooms; 2 1/2 baths; large, sunny and open living and dining rooms with decks; primary BR suite with vaulted and beamed ceiling, walk-in closet, full bath; decks off dining room and the living room with southerly views and surrounded by a tranquil landscape. 2 car atta...

17 Main St. Rare opportunity to own a beautifully restored Berkshire cottage at 17 Main Street, perfectly situated in the vibrant heart of downtown Lenox. This remarkable property, originally built in 1883 and once the residence of Gilded Age shipping magnate John Schermerhorn, combines historic elegance with modern comfort. The home underwent a comprehensive renovation between 2021 and 2025, i...