Berkshire MA Real Estate | William Pitt Sotheby's International Realty

10/26/2026

A private 53.65-acre estate in the Hudson Highlands, Evarts Hill is a restored 1929 French Normandy chateau surrounded by formal gardens and protected landscapes, just 50 miles from New York City.

Comment “Link” and we will send you this listing.⁠
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61 Evarts Hill #41, Garrison, NY
Offered at $8,950,000
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Represented with Anthony Cutugno. Learn more via the link in bio.⁠
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10/24/2026

Designed with a world-class art collection in mind, this contemporary residence treats the home as a gallery. Expansive, UV-protected walls provide space for fine art, while carefully framed vistas bring the surrounding landscape into view. Board-formed concrete and Vermont slate define its architectural character.

Explore a home where art, architecture, and landscape share the spotlight.

5 Deer Hill Road, West Stockbridge, MA⁠
Offered at $4,975,000⁠
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Represented with Leslie Glenn Chesloff. Learn more via the link in this post.
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10/24/2026

A Contemporary Colonial in the coveted gated community of The Springs, featuring cathedral ceilings and walls of glass opening to a private waterfront patio. ⁠
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3 Pondview W, Purchase, NY⁠
Offered at $1,850,000⁠
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Represented with Andrea Markowitz. Learn more via the link below.

https://wpsir.co/3PondviewW
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10/23/2026

Once a 19th-century sawmill, this Branford stone residence features a private waterfall, a tidal creek, and scenic water views in a remarkable shoreline setting.

Comment “Link” and we will send you this listing. ⁠
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55-69 Sawmill Road, Branford, CT
Offered at $1,625,000
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Represented with Michelle Wininger & Mark McElrath. Learn more via the link below.

https://wpsir.co/55-69SawmillRoad
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10/23/2026

Escape the Hamptons traffic and indulge in effortless sophistication at this commanding 1.47-acre Westchester resort-style estate, offering unparalleled privacy, a private saltwater pool oasis, and a 21-foot double-height living room just under an hour from Manhattan.⁠

23 Pheasant Drive, Rye, NY⁠
Offered at $4,480,000⁠
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Represented by Annalise Stack. Learn more via the link below.
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10/23/2026

Discover these properties selected for the New York Times’ On The Market column, including this three-bedroom, 2,360-square-foot home in Fairfield, CT. Click the link below to read the full story.

This week’s properties are a four-bedroom in Katonah, N.Y., and a three-bedroom in Fairfield, Conn.

10/22/2026

Custom crafted by Fox Hill Builders, this five-bedroom Seagate home offers light-filled interiors, sweeping water views, generous entertaining spaces, and a private mooring in one of Darien’s most desirable coastal settings.
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12 Seagate Road, Darien, CT
Offered at $4,725,000
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Represented with Amy Barsanti. Learn more via the link below.

https://wpsir.co/12SeagateRoad
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10/21/2026

This nearly 11 acre Briarcliff Manor estate offers a skyline view terrace, tennis court, resort pool, and renovated entertainment lounge.⁠
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Comment "Link" and we will send you this listing.⁠
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778 Sleepy Hollow Road, Briarcliff Manor, NY⁠
Offered at $8,500,000⁠
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Represented with JoAnn Reilly & Beth Hargraves. Learn more via the link below.

https://wpsir.co/778SleepyHollowRoad
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10/21/2026

A former dairy barn with a story to tell, now a welcoming Kent home with 14 acres to explore, a heated pool, river frontage, and a silo turned into an office, art studio, and gym.
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391 Kent Cornwall Road, Kent, CT
Offered at $1,200,000⁠
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Represented with Vanessa Henderson & Steve Pener. Learn more via the link below.

https://wpsir.co/391KentCornwallRd

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10/21/2026

Stop in the Berkshires for some Halloween spirit at The Incredible Naumkeag Pumpkin Show!

Running Wednesdays through Sundays from 5 to 9 PM this October, Naumkeag transforms into a magical fall destination featuring thousands of carved pumpkins, gourds, and mums, alongside playful displays of cauldrons, volcanoes, and fairy houses. Each year brings fresh, family-friendly exhibits that celebrate the enchanting spirit of October.

While you’re enjoying the magical autumn season in the Berkshires, remember that our local William Pitt Sotheby’s International Realty team is right here to help you find your perfect home in the area!

10/20/2026

As featured in CT Insider, Vin Socci shares his expert insight on when to integrate AI in the home buying process. Click the link below to read the full story.

A Zillow survey found 6 in 10 homebuyers use AI to find listings, do market research, get offer guidance and other information.

10/19/2026

From colonial’s to turnkey single-level living, explore our curated selection of exceptional homes across the Berkshires.Click the link in our bio to browse our newest listings.


Turnkey living meets the ultimate workspace in this beautifully updated Pittsfield gem!

Welcome to 44 Melbourne Road! This completely move-in-ready 3-bed, 2-bath raised ranch offers 1,789 sq. ft. of beautifully updated living space. Highlights include a bright, open kitchen with quartz countertops, a finished walkout lower level with a bonus room, and a screened-in porch perfect for outdoor dining. But the real showstopper? The garage space! In addition to an attached 2-car garage, this property features a massive detached 40x30-foot, 3-bay heated and insulated garage with 12-foot ceilings and its own 200-amp service! Complete with brand-new exterior siding and a new roof, this property is the perfect combination of turnkey living and exceptional workspace.

44 Melbourne Rd, Pittsfield, MA
Offered At: $469,000
Listed By: Danielle Giulian & Maggie Barry Gavin

Enjoy quaint, cozy, and completely turnkey single-level living in Pittsfield!

Located on a highly sought-after, tree-lined street in southeast Pittsfield, this sweet 2-bed, 1-bath home offers effortless living. Highlights include a beautifully updated kitchen with stainless steel appliances and cherry cabinetry, a handsome stone fireplace in the living room, and an oversized sunroom with flagstone flooring. Outside, relax in a surprisingly large, fully fenced-in backyard complete with a stone patio, fire pit, and raised garden beds. With central air, a remodeled bath, and an unfinished attic ready for your future vision, this picture-perfect home is ready for you to move in just in time for the holidays!

34 Sampson Pkwy, Pittsfield, MA
Offered At: $339,900
Listed By: Tonia L. Scalise

Tradition meets Berkshire country style in this special in-town colonial!

This 3-bed, 1-bath 1920s home offers the ultimate blend of city convenience and peaceful country living. Set on a private 0.76-acre lot surrounded by over 80 acres of state-protected land, this property features gleaming hardwood floors, an inviting screened-in front sleeping porch, a vintage-style kitchen, and a partially finished basement. Outside, you'll find an oversized 2-car detached garage that is an auto lover's dream! Enjoy incredible privacy while being just a short walk to the Upstreet Cultural District, local dining, and all city conveniences.

Address: 92 Noblehurst Ave, Pittsfield, MA
Offered At: $372,900
Listed By: Tonia L. Scalise

10/16/2026

6 closings in one incredible week within the Berkshires!

Swipe through to see the beautiful properties we officially took off the market this week. From Stockbridge to Dalton, MA, it was a busy week matching amazing clients with their next chapters. Congratulations to our new buyers and our fabulous sellers.

The Berkshire market is still moving. Whether you are looking to buy or sell, let’s get to work on your real estate goals! Check out the link in our bio for more amazing properties like these!


MassachusettsRealEstate

10/15/2026

From colonial’s to private compounds, explore our curated selection of exceptional homes across the Berkshires. Click the link in our bio to browse our newest listings.

Discover incredible charm and surprising space in this beautifully maintained Lee home!

Welcome to 130 Laurel St, a character-filled 3-bed, 2-bath Colonial offering 1,716 sq. ft. of comfortable living space. Step up to the lovely mahogany front porch and enter to find gleaming wood floors, a stately fireplaced living room, and a beautifully updated kitchen featuring cherry cabinetry. The main floor also boasts a dedicated office addition and den, while upstairs features three ample bedrooms and an updated bath with a walk-in shower. Outside, enjoy a large deck and a great fenced-in backyard. With sidewalks straight to town and Laurel Lake just minutes away, this lovingly cared-for home is ready for its next chapter!

130 Laurel Street, Lee, MA
Offered At: $474,900
Listed By: John Burns

Welcome to your own private sports compound and sanctuary in Great Barrington!

Tucked away on a quiet road, this incredible 4-acre retreat at 20 Cooper Rd centers around an in-ground heated swimming pool and a dedicated tennis/pickleball court! Inside, this beautifully designed 4-bed, 3-bath Mid-Century Modern home offers 2,631 sq. ft. of space with clean architectural lines and remarkable flow. Highlights include two cozy fireplaces, dedicated work-from-home space, and a stunning sunroom overlooking the grounds. With major energy upgrades like a high-output solar array keeping operational costs low, this turnkey private playground is just minutes from downtown dining, skiing, and cultural landmarks!

20 Cooper Road, Great Barrington, MA
Offered At: $899,000
Listed By: Tony Segalla & Karen Climo

10/14/2026

Sneak peek! Over 36 acres of private Berkshire luxury just moments from the heart of Lenox!

Welcome to 20 E Dugway Rd! This incredible 36+ acre estate features a beautifully configured multi-generational main residence and a complete, independent guest house that feels like a second home entirely. With an oversized stone fireplace, a heated sunroom, multiple kitchens, and endless outdoor space bordered by state forest, this is the ultimate Berkshire compound. Check out this quick sneak peek and imagine the possibilities!

20 E Dugway Rd, Lenox, MA
Offered At: $1,650,000
Listed By: Nick Geranios & Carrie Lobovits Wright

10/13/2026

Incredible opportunity or perfect live/rent setup in Great Barrington!

Located at 392-394 Park St, this fantastic multi-unit property offers endless potential! Whether you are an investor looking to add to your Berkshire portfolio or a buyer searching for a home with income-generating potential, this is a must-see. Don’t miss out on this rare Berkshire find!

392-394 Park St, Great Barrington,MA
Offered At: $949,000
Listed By: Tony Segalla

10/12/2026

From historic colonial’s to private Berkshire escapes, explore our curated selection of exceptional homes across the Berkshires.Click the link in our bio to browse our newest listings.


Step back in time without sacrificing modern luxury in this pristine 1782 Colonial retreat!

Located at the end of a quiet country road and bordering protected wildlife land, this meticulously preserved 4-bed, 3-bath center chimney colonial offers ultimate privacy and breathtaking, masterfully cultivated gardens. Inside, you'll find the perfect blend of historic charm and modern comfort, featuring wide board floors, original exposed beams, two fireplaces, and a stunningly updated kitchen with quartz counters that flows right into a sunlit family room. Enjoy complete silence and extraordinary night skies, all just 20 minutes from Lee and 30 minutes from Great Barrington!

802 Stebbins Rd, Otis, MA
Offered At: $875,000
Listed By: Chapin Fish and Shannon Margraf

Incredible potential awaits on 10 private acres in Alford!

Looking for a private Berkshire escape to make your own? This 10.69-acre property at 85 West Rd features beautiful seasonal views and includes two structures ready for your vision. The main 3-bed, 1-bath chalet-style home offers 1,512 sq. ft. with an open living/dining room, kitchen, and deck for relaxing. A separate studio building with two rooms and a half bath provides endless possibilities for an office, guest space, or creative retreat.

85 West Rd, Alford, MA
Offered At: $775,000
Listed By: Pat Melluzzo, Real Estate in the Berkshires

10/09/2026

5 closings in one incredible week!

Swipe through to see the beautiful properties we officially took off the market this week. From Coulmbia County to the Berkshires, it was a busy week matching amazing clients with their next chapters. Congratulations to our new buyers and our fabulous sellers.

The market is still moving. Whether you are looking to buy or sell, let’s get to work on your real estate goals! Check out the link in our bio for more amazing properties like these!

10/08/2026

From colonial’s to multi-level condo’s explore our curated selection of exceptional homes across the Berkshires.Click the link in our bio to browse our newest listings.


Your ultimate year-round mountain sanctuary awaits at Jiminy Peak!

Welcome to 9102 Mountainside Dr, a stunning 3-bed, 3-bath multi-level condo offering nearly 2,000 sq. ft. of luxury living! Step inside to find a beautifully updated space featuring vaulted ceilings, a cozy fireplace, and an interior balcony leading to a spacious upstairs loft. Outside, relax on your private, meticulously landscaped patio that's perfect for al fresco dining.

9102 Mountainside Dr, Hancock, MA
Offered At: $614,999
Listed By : Carrie Lobovits Wright and Stephen R. Schoenfeld

Historic warmth meets vibrant, bright spaces in this captivating Berkshire colonial!

Open the classic wooden Dutch door of 41 Quincy St to find a 5-bed, 2.5-bath home full of character and colorful impact. Featuring 2,808 sq. ft. of space, this beautifully updated 1850s property greets you with a stunning stone fireplace, grand staircase, and gorgeous wood floors. A spacious layout provides total flexibility, including a convenient first-floor bedroom.

41 Quincy St, North Adams, MA
Offered At: $295,000
Listed By: Diane Thorson - Realtor

10/08/2026

The Third Quarter 2026 Market Watch has arrived.
Take a closer look at where the market stands and where it’s headed.

Read more at williampitt.com