Header photo courtesy 1 and 5 Park Avenue, Dalton MA
It’s that time of year in the Northeast when the days subtly shorten, golden-hour light lingers a little longer, and back-to-school is right around the corner. Fortunately, life across the Massachusetts–New York border offers distinct charm in every season.
To celebrate the turn of the season, we’ve selected 10 exclusive Stone House Properties listings across Columbia County, NY, and Berkshire County, MA, designed for seamless indoor-outdoor living. Whether you’re seeking expansive screened porches, mountain-view pools, or stone hearths built for crisp twilight, these homes showcase the very best of late-summer country living.
1. 58 Round Hill Rd, Great Barrington, MA
Price: $4,250,000
Listing Agents: Sheila Thunfors & Nikki Carchedi
Highlight: Infinity Pool & Fireplace Screened Porch
The screened porch at 58 Round Hill Rd features a dedicated stone fireplace, making it the ultimate spot to gather as evening temperatures cool down. Overlooking an extraordinary infinity pool with panoramic mountain vistas, this private luxury estate delivers complete tranquility—all within three miles of vibrant downtown Great Barrington.
2. 32 Crooked Hill Rd, Alford, MA
Price: $3,495,000
Listing Agent: Nikki Carchedi
Highlight: Resort-Style Grounds & Soaring Great Room
A private swimming pool and tennis court offer endless motivation to spend warm afternoons outdoors. Step inside to an impressive great room defined by soaring ceilings, a central fireplace, and a full wall of glass doors filling the space with natural light. It’s an unmatched front-row seat for watching the Berkshire foliage begin its seasonal shift.
3. 36 Yale Hill Rd, Stockbridge, MA
Price: $2,950,000
Listing Agents: Mandy Victor-Pieczarka & Scott Sawyer
Highlight: Screened Porch & Expansive Entertaining Patio
Masterfully crafted with timeless architectural details, this contemporary Cape seamlessly connects its interior living spaces with nature. Just off the main hall sits both an expansive stone patio and an airy screened porch—ideal vantage points for taking in the serene acreage and wooded privacy of this 9+ acre retreat.
4. 311 Co Rd 13, Old Chatham, NY
Price: $2,600,000
Listing Agent: Nikki Carchedi
Highlight: Dual Stone Fireplaces & 101 Acre Views
Set across 101 rolling acres in scenic Columbia County, this estate offers postcard-worthy views in all four seasons. Choose your favorite gathering spot: the indoor stone fireplace for chillier nights, or outdoor fireplace on the stone patio designed for starlit conversations.
5. 39 Pine Crest Cross Rd, Egremont, MA
Price: $2,400,000
Listing Agent: Sheila Thunfors
Highlight: Wraparound Porch & Designer Gardens
Designed for relaxed, effortless indoor-outdoor flow, 39 Pine Crest Cross Rd boasts multi-level decks and a deeply welcoming front porch. Unwind after dinner with a warm drink while admiring expertly curated gardens just steps away.
Explore 39 Pine Crest Cross Rd →
6. 1 & 5 Park Ave, Dalton, MA
Price: $1,795,000
Listing Agents: Elisha Poirier & Sheila Thunfors
Highlight: Dual-Residence Compound with Multiple Sun Porches
Between the stately main home of 1 Park Avenue and the charming carriage house at 5 Park Avenue, there are countless little sanctuaries that lend perfectly to indoor-outdoor life in the summer season. From the multiple sun porches, covered porches, and balcony off the primary suite, it’s easy to soak up the last bits of sun.
7. 699 Hartsville New Marlboro Rd, New Marlborough, MA
Price: $1,295,000
Listing Agents: Sheila Thunfors & Allison Rada
Highlight: Mid-Century Design & Screened Gazebo
This architect-designed mid-century modern home effortlessly blends retro flair with surrounding natural beauty. The screened gazebo offers that little bit of protection from the elements you might wish for as the season changes. Or, stay inside and take in floor-to-ceiling forest vistas from the main living area.
Explore 699 Hartsville New Marlboro Rd →
8. 6 Manitauk Heights, Stockbridge, MA
Price: $1,060,200
Listing Agent: Patricia Andrew
Highlight: Sunroom with Built-in Library Wall
Located just two miles from historic downtown Stockbridge, this light-filled home is tailored for quiet relaxation. The sunroom features a full floor-to-ceiling bookcase, creating an inviting reading nook to unplug and enjoy a slower pace of country life.
9. 34 Queechy Shore Beach Rd, Canaan, NY
Price: $529,000
Listing Agent: Nancy Cuddihy
Highlight: Queechy Lake Rights & Stone Hearth
Maximize late-summer lake days without spending hours in the car. As part of the Queechy Shores Beach Association, this property offers access to a members-only boat launch nearby. After an afternoon on the water, return home to relax around the living room’s stone fireplace.
Explore 34 Queechy Shore Beach Rd →
10. 83 Beech Tree Ln, Becket, MA
Price: $435,000
Listing Agent: Jeff Wilkinson
Highlight: Becket Woods Amenities & Cozy Wood Stove
Situated in the sought-after Becket Woods community, this turnkey home offers instant access to a local swimming pond, hiking trails, and tennis courts. After a day outdoors, enjoy dinner on the dining deck or curl up inside by the wood stove. Plus, a covered carport guarantees dry entry through every Berkshire season.
Finding Your Dream Home in the Berkshires & Hudson Valley
Whether you are searching for an estate with an infinity pool, a waterfront sanctuary, or a cozy historic getaway, our expert agents at Stone House Properties are here to help you navigate the local market.
Contact Stone House Properties Today to schedule a private tour of these featured listings or explore more properties across Columbia County and the Berkshires.
